JPH08231807A - Primer composition and plastic lens - Google Patents

Abstract

PURPOSE: To obtain a primer compsn. which can form a highly transparent primer layer between a substrate and a hard coating layer by compounding a specific polyvinyl acetal, a specific cross-linker, a finely particulate inorg. substance, an org. solvent, and water. CONSTITUTION: This primer compsn. comprises polyvinyl acetal represented by formula I (wherein R<1> is H or a 1-20C satd. hydrocarbon group; a and b are each 10-90; and c is 0-10 provided a+b+c is 100), a cross-linker such as a hydrolyzable organosilane compd. represented by formula II (wherein R<2> and R<3> are each an optionally substd. hydrocarbon group; X<1> is a hydrolyzable group; and d and e are each 0-3) or formula III (wherein R<4> is a 2-8C org. group; R<5> and R<6> are each an optionally substd. 1-8C hydrocarbon group; X<2> is a hydrolyzable group; and f and g are each 0-2) or its hydrolyzate, a finely particulate inorg. substance, an org. solvent, and water and enables the production of a plastic lens excellent in resistances to impact, heat, scratch, and abrasion.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a base material and a scratch resistant film (hereinafter referred to as a hard coat layer) in a plastic lens or the like having excellent impact resistance, heat resistance, scratch resistance and abrasion resistance. The present invention relates to a coating layer (referred to as a primer layer) having excellent transparency, which is provided between the primer layer and the primer composition.

[0002]

2. Description of the Related Art Plastic lenses are lightweight, shock resistant,
It has advantages such as easy workability and easy dyeing.
In particular, it is rapidly spreading in the field of spectacle lenses. However, plastic lenses generally have the drawback of being extremely vulnerable. Therefore, the surface of the plastic lens substrate is usually treated with an organosilane-based hard coat for the purpose of improving the surface hardness. Further, by forming an optical thin layer mainly made of an inorganic material having a refractive index different from that of the plastic substrate on the surface of the hard coat layer, it is possible to reduce the light reflectance and improve the light transmittance, thereby superimposing images (flare). 2) suppresses the surface reflection of light which causes a decrease in contrast or double image formation (ghost).

However, although plastic lenses for eyeglasses are much stronger than glass lenses against impacts from the direction perpendicular to the lenses, the lens surface cracks or breaks against impacts above a certain level. There is a possibility that the lens base material may scatter if it gets stuck. This tendency is more remarkable in the case of the same material having a thinner lens center thickness, and is more remarkable in a lens provided with a hard coat layer and an antireflection film. This is because it is conceptually certain that the impact resistance of the lens itself decreases as the lens thickness decreases, and the flexibility of the lens, that is, shock absorption, is sharply increased by providing a hard coat layer and an antireflection layer. As a result, the impact resistance decreases.

The demand for spectacle lenses is shifting to thinner and lighter ones, which are excellent in scratch resistance, have no flare or ghost, and are easy to see and free from eye strain. Therefore, impact resistance is required for eyeglass lenses used for vision correction, fashion, or both. In the United States, safety standards have been established for medical devices and pharmaceuticals including eyeglasses. For eyeglass lenses that are vision correction devices, Food and Drag Administration (hereinafter,
There is a safety standard called "FDA". According to FDA standards, 50 inches above the plastic lens (127c
m), diameter 5/8 inch (16.3mm), weight 0.56
It is required that an ounce (15.9g) iron ball be dropped so that no debris is scattered.

[0005]

DISCLOSURE OF THE INVENTION In order to provide a plastic lens that passes the FDA standard, the inventor has solved the problems described in Japanese Patent Application Nos. 7-002288 and 7-000903, Not to mention shock resistance,
A practical primer that does not dissolve in the solvent used for the hard coat solution, the usable time of the primer solution (called pot life) is within the practical range, and does not cause problems such as discoloration or discoloration when dyeing plastic lenses. A plastic lens was found using the composition and the primer composition.

This primer composition can be used not only for plastic lenses for spectacles but also for plastic lenses for optical devices and plastic panels, and is effective in achieving both impact resistance and scratch resistance. Plastic lenses are used in various environments, and in the case of eyeglass lenses, it is often the case that they are left inside the car in the hot sun. Considering the environment in which they are used, heat resistance of about 100 ° C is necessary, and the primer layer Improving the heat resistance of plastic lenses coated with has become an issue.

Further, these primer layers also have a refractive index of about 1.50, and a plastic layer for low refractive index (refractive index of about 1.50) has a primer layer or a primer layer / hard coat layer or a primer layer / hard coat. When the layer / antireflection layer is applied and used as a spectacle lens, no problem occurs. However, when a plastic lens for medium refractive index (refractive index of about 1.55) or a plastic lens for high refractive index (refractive index of about 1.60) is provided with the same layer as above, interference fringes are generated on the lens. If it is used as a spectacle lens, it becomes difficult to see a transmitted image and eyes are tired, which is not preferable. This is because the difference in the refractive index between the base material and the primer layer became too large, and when it is used as an optical lens as well as an eyeglass lens, it is necessary to devise a method for suppressing interference fringes on the lens as much as possible. Becomes
In the structure having a primer layer made of an organic resin composition between the plastic lens substrate and the hard coat layer, interference color can be obtained by suppressing the difference in refractive index between the plastic lens substrate, the primer layer and the hard coat layer. Can be suppressed.

In order to obtain thinner and lighter plastic lenses, it is necessary to use an aspherical shape or to use a plastic substrate having a higher refractive index. To maximize the thinness and lightness, it is effective to use a high refractive index plastic material. In that case, in order to suppress the interference fringes, it is necessary to make the respective refractive indexes of the primer layer and the hard coat layer substantially the same as those of the plastic lens substrate for high refractive index.

As described above, there is a need for a primer layer which is excellent in impact resistance and heat resistance and whose refractive index can be adjusted.

[0010]

The present inventor has conducted extensive studies in order to solve the above problems, and as a result, the present invention is as follows. Firstly, the present invention is "at least (A) general formula (I)".

[0011]

[Chemical 6]

(In the formula, R ¹ is a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms, a is a fraction of a constitutional unit having an acetal group, 10 to 90, and b is OH.
The ratio of the structural unit having a group is 10 to 90, c is the ratio of the structural unit having an acetyl group, 0 to 10, and a
+ B + c = 100. ) And a polyvinyl acetal represented by the formula (B) and a general formula (II)

[0013]

[Chemical 7]

(In the formula, R ² and R ³ are substituted or unsubstituted hydrocarbon groups having 1 to 8 carbon atoms, X ¹ is a hydrolyzable group, and d and e are 0 to 3). It is an integer.)
A hydrolyzable organosilane compound represented by or a hydrolyzate thereof, or a general formula (III)

[0015]

Embedded image

(Wherein, R ⁴ is an organic group having 2 to 8 carbon atoms, R ⁵ and R ⁶ are substituted or unsubstituted hydrocarbon groups having 1 to 8 carbon atoms, and X ² is Is a hydrolyzable group,
f and g are integers from 0 to 2. ) A hydrolyzable organosilane compound represented by or a hydrolyzate thereof,
Or general formula (IV)

[0017]

[Chemical 9]

(Wherein R ⁷ is a substituted or unsubstituted hydrocarbon group having 1 to 6 carbon atoms), a dialdehyde compound or glyoxal, or a general formula (V)

[0019]

[Chemical 10]

(In the formula, R ⁸ is a substituted or unsubstituted hydrocarbon group having 1 to 6 carbon atoms, and R ⁹ is 1 to 4 carbon atoms.
Is a saturated hydrocarbon group. ) A dialdehyde acetal compound represented by the formula (1), a primer composition comprising at least one cross-linking agent selected from the group consisting of: (C) a particulate inorganic material; and (D) an organic solvent and water, The content of the polyvinyl acetal as the component (A) is 1 to
30% by weight, the content of the cross-linking agent that is the component (B) is 0.01 to 30% by weight, and the content of the fine particulate inorganic material that is the component (C) is 10 to 80% by weight. A primer composition (claim 1) "is provided.

The second aspect of the present invention is that, in the primer composition, 0.002 to 20% by weight of a curing catalyst is dispersed and contained in the primer composition. 2) ”is provided. Further, the present invention thirdly provides the "primer composition (claim 3) according to any one of claims 1 to 2, wherein the polyvinyl acetal is polyvinyl butyral".

A fourth aspect of the present invention is that the hydrolyzable organosilane is an alkoxysilane compound whose hydrolyzable group is an alkoxy group having 1 to 4 carbon atoms.
The primer composition according to any one of (1) to (4) is provided. In the fifth aspect of the present invention, "the fine-particle inorganic material has an average particle size of 1 to 300 nm of aluminum oxide, iron oxide, silicon dioxide, cerium oxide, tungsten oxide, molybdenum oxide, titanium oxide, zirconium oxide, tin oxide, A primer composition (claim 5) according to claim 1, which is at least one kind or a combination of two or more kinds selected from antimony oxide, zinc oxide and beryllium oxide.

The sixth aspect of the present invention is, "In a plastic lens having a hard coat layer on both surfaces of a plastic lens substrate, between at least one of the plastic lens substrate surface and the hard coat layer, There is provided a plastic lens (claim 6) having a primer layer made of a crosslinked polyvinyl acetal resin in which a fine particle inorganic substance is dispersedly contained.

Further, the present invention seventhly provides "a plastic lens (claim 7) according to claim 6, wherein an antireflection film is provided on the hard coat layer". In the eighth aspect of the present invention, "the fine particle inorganic material has an average particle diameter of 1 to 300 nm, such as aluminum oxide, iron oxide, silicon dioxide, cerium oxide, tungsten oxide, molybdenum oxide, titanium oxide, zirconium oxide, and tin oxide. The plastic lens (claim 8) according to claim 6 or claim 7, characterized in that it is at least one kind or a combination of two or more kinds selected from antimony oxide, zinc oxide and beryllium oxide. .

The present invention will be described in more detail below. As the polyvinyl acetal resin, those having 0 to 20 carbon atoms in the alkyl group of the acetal portion can be used, and those having 0 to 10 carbon atoms are preferable, and the carbon chain of the alkyl group portion may be branched even if it does not have a linear structure. There may be. Particularly preferred is polyvinyl butyral in which the alkyl group has 3 carbon atoms. A polyvinyl acetal having an acetalization degree of 10 to 90% can be used, and preferably 20 to 80%. If the degree of acetalization of the polyvinyl acetal is less than 10%, the weather resistance is lowered and the impact strength is insufficiently improved. Moreover, the acetalization degree is 9
0% or more of polyvinyl acetal is difficult to synthesize,
Even if it can be synthesized, it is expected that the adhesiveness to the plastic substrate will decrease.

The average degree of polymerization of the polyvinyl acetal is preferably 5,000 or less, more preferably 100 to 3,000. When the average degree of polymerization of polyvinyl acetal is more than 5,000, it becomes difficult to dissolve in a solvent and it is difficult to synthesize polyvinyl acetal having an optimum degree of acetalization. If the average degree of polymerization of polyvinyl aceal is less than 100,
The impact resistance is insufficiently improved. The content of polyvinyl acetal in the primer composition is preferably 1 to 30% by weight, more preferably 2 to 20% by weight. When the content of polyvinyl acetal is more than 30% by weight, the viscosity of the primer composition becomes too high, which makes it difficult to apply it to a plastic lens, the applied primer layer becomes thick, and the uniformity of the applied surface is lost. I will be broken. If the content of polyvinyl acetal is less than 1% by weight, the impact resistance becomes insufficient because the applied primer layer is thin.

In the present invention, the residual hydroxyl group in the polyvinyl acetal resin can be used for crosslinking, and the acetal bond in the polyacetal resin is an equilibrium reaction under acidic conditions, and the resulting hydroxyl group is used for crosslinking reaction. be able to. Therefore, as a cross-linking agent for forming a cross-linked structure, a molecule having two or more functional groups that react with a hydroxyl group in one molecule can be used.

As the crosslinking agent, (1) dialdehyde compound or acetal compound of dialdehyde (2) hydrolyzable organosilane compound (3) mixed system of hydrolyzable organosilane compound and dialdehyde compound, or hydrolyzable organo A mixed system of a silane compound and an acetal compound of dialdehyde is used. In the case of a dialdehyde compound, the aldehyde group reacts with the hydroxyl group in the polyvinyl acetal by the action of the catalyst, or an acetal bond is newly formed by the acetal exchange reaction with the alkyl acetal group. Since the dialdehyde compound has two aldehyde groups in the molecule, the polyvinyl acetal is cross-linked between or in the molecule. That is, it is possible to three-dimensionally crosslink. Since the acetal compound of dialdehyde has an equilibrium relationship with the corresponding dialdehyde in the presence of water and an acidic catalyst, it is considered that the crosslinking reaction mechanism is exactly the same as that of dialdehyde. The dialdehyde compound or the dialdehyde acetal compound may be used alone, or two or more kinds of dialdehyde compounds may be mixed and used. Examples of the compound include glyoxal, glutaraldehyde, hexanediar, 2-hydroxyhexanedial, malonaldehyde tetramethylacetal, malonaldehyde tetraethylacetal, glutaraldehyde tetramethylacetal, glutaraldehyde tetraethylacetal and the like.

The addition amount of the dialdehyde compound or the dialdehyde acetal compound in the polyacetal resin solution is preferably 0.01 to 30% by weight, and preferably 0.1 to 20% by weight.
Is particularly preferable. In the case of a hydrolyzable organosilane compound, the hydrolyzable group in the organosilane compound is hydrolyzed to form a silanol group, which is intermolecular or molecular by dehydration condensation with the hydroxyl group in the polyvinyl acetal by the action of the catalyst and heat. The cross-linking takes place within. That is, three-dimensional crosslinking is possible.

The molecule that participates in crosslinking is a hydrolyzate of an organosilane compound or a condensate thereof. The organosilane compound may be added as it is, or may be previously hydrolyzed. Further, one kind of organosilane compound may be used alone, or two or more kinds of organosilane compound may be mixed and used. As the organosilane compound, a halosilane compound whose hydrolyzable group is a halogen atom, a carboxysilane compound whose hydrolyzable group is a carboxy group, and a ketoxime silane compound whose hydrolyzable group is a ketoxime group,
Alternatively, alkoxysilane compounds whose hydrolyzable group is an alkoxy group are preferable, and alkoxysilane compounds are more preferable. Examples of the compound include dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, phenylmethyldimethoxysilane, phenylmethyldiethoxysilane, γ-chloropropylmethyldimethoxysilane, γ-chloropropylmethyldiethoxy. Silane, γ-
Methacryloxypropylmethyldimethoxysilane, γ-
Methacryloxypropylmethyldiethoxysilane, γ-
Mercaptopropylmethyldimethoxysilane, γ-mercaptopropylmethyldiethoxysilane, γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethyldiethoxysilane, methylvinyldimethoxysilane, methylvinyldiethoxysilane, γ-glycidoxypropylmethyl Dimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltributoxysilane, methyltris (2-methoxyethoxy) silane, ethyltrimethoxysilane, ethyltrimethoxysilane Ethoxysilane, ethyltripropoxysilane, ethyltributoxysilane, ethyltris (2-methoxyethoxy) silane, propyltrimethoxysilane, propyltriene Toxysilane, butyltrimethoxysilane, butyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, phenyltrimethoxysilane, phenyltriethoxysilane , Γ
-Chloropropyltrimethoxysilane, γ-chloropropyltriethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, 3,3,3-trifluoropropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltrimethoxysilane, γ-
Mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, chloromethyltrimethoxysilane, chloromethyltriethoxysilane, N-
(Β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxy Silane, (3,4-epoxycyclohexylmethyl) trimethoxysilane, (3,4-epoxycyclohexylmethyl) triethoxysilane, β- (3,4-epoxycyclohexylethyl) trimethoxysilane, β
-(3,4-epoxycyclohexylethyl) triethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, 1,1-bis (trimethoxysilyl) ethane, 1,
1-bis (triethoxysilyl) ethane, 1,2-bis (trimethoxysilyl) ethane, 1,2-bis (triethoxysilyl) ethane, 1,3-bis (trimethoxysilyl) propane, 1,3- Bis (triethoxysilyl)
Examples thereof include propane, 2,2-bis (trimethoxysilyl) propane and 2,2-bis (triethoxysilyl) propane. The addition amount of the organosilane compound in the primer composition is preferably 0.01 to 30% by weight,
0.1 to 20% by weight is more preferable.

In the case of a mixed system of a hydrolyzable organosilane compound and a dialdehyde compound, or a mixed system of a hydrolyzable organosilane compound and an acetal compound of a dialdehyde, a dialdehyde compound or an acetal compound of a dialdehyde as described above is used. The reaction and the reaction similar to the reaction of the hydrolyzable organosilane occur in the mixed system. The addition amount of the dialdehyde compound or the dialdehyde acetal compound in the primer composition is 0.01 to 30% by weight.
However, 50 mol% or less of the organosilane compound is preferable. If the addition amount of the dialdehyde compound or the acetal compound of dialdehyde exceeds 50 mol% of the addition amount of the organosilane compound, impact resistance decreases.

As the curing catalyst, (1) particularly in a system using a dialdehyde compound or an acetal compound of dialdehyde as a crosslinking agent, as long as it promotes an acetalization reaction between an aldehyde group and a hydroxyl group in polyvinyl acetal. There is no limit. (2) The system using a hydrolyzable organosilane compound as a crosslinking agent is not particularly limited as long as it promotes dehydration condensation between the silanol groups produced by hydrolysis and the hydroxyl groups in the polyvinyl acetal.

(3) In a mixed system of a hydrolyzable organosilane compound and a dialdehyde compound or a mixed system of a hydrolyzable organosilane compound and an acetal compound of dialdehyde, the hydrolyzable organosilane compound is hydrolyzed. There is no particular limitation as long as it promotes dehydration condensation between the silanol groups thus formed and the hydroxyl groups in the polyvinyl acetal and the acetalization reaction between the dialdehyde compound or the acetal compound of the dialdehyde and the hydroxyl groups in the polyvinyl acetal.

An acidic catalyst is effective in any of the crosslinking agents (1), (2) and (3). For example, inorganic acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, organic acids such as formic acid, acetic acid, benzoic acid, phthalic acid, methanesulfonic acid, benzenesulfonic acid, and alkylbenzenesulfonic acid having 1 to 18 carbon atoms in the alkyl group. An organic tin compound such as dibutyltin dilaurate, dibutyltin dioctate, or dibutyltin diacetate can be used. Particularly preferred is
Inorganic acids such as hydrochloric acid and nitric acid, organic acids such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, and organic tin compounds. These may be used alone or in combination of two or more kinds of catalysts. The content of the curing catalyst in the primer composition is 0.0
02 to 10% by weight is preferable, and 0.005 to 2% by weight is more preferable.

In addition, a metal complex catalyst having acetylacetone or ethylenediamine as a ligand, a metal salt of perchloric acid,
Alternatively, it is also effective to use a solid catalyst. The solid catalyst includes metals, metal oxides, metal sulfides, sulfates, carbonates and the like, but any solid catalyst having the above-mentioned catalytic ability may be used. The catalyst may be used alone, or two or more kinds of catalysts may be mixed and used. Moreover, you may use it, mixing with an acidic catalyst. The amount of the metal catalyst added to the primer composition is preferably 0.001 to 10% by weight, more preferably 0.005 to 5% by weight.

The solvent used in the primer composition includes
There are hydrocarbons, halogenated hydrocarbons, alcohols, ketones, esters, ethers, and other well-known solvents that can dissolve polyvinyl acetal well are preferable. In particular, methanol, ethanol, propanol, butanol, hexanol, methyl cellosolve, ethyl cellosolve, propyl cellosolve, butyl cellosolve, acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, tetrahydrofuran, dioxane, acetic acid, methyl acetate, ethyl acetate are preferable, and these are alone. Or a mixed solvent of two or more kinds.

When the crosslinking agent contains an organosilane compound, the water content of the primer composition is 0.1 to 20% by weight as the amount required for the hydrolysis of the organosilane compound. Further, even when the cross-linking agent is a dialdehyde compound or a dialdehyde acetal compound, water may be added. If the water content is greater than 20% by weight,
Depending on the type of organic solvent in the primer composition, the smoothness of the applied primer surface is lost. If the water content is less than 0.1% by weight, the pot life of the primer composition will be shortened. Examples of the fine particle inorganic substance include fine particles of metal oxide such as zinc oxide, aluminum oxide, titanium oxide, zirconium oxide, tin oxide, antimony oxide, silicon dioxide, beryllium oxide, and tungsten oxide, which may be used alone or 2 You may use as a composite fine particle of more than 1 type. When a primer composition containing these finely divided inorganic substances dispersed therein is formed as a primer layer on the surface of a plastic lens substrate, the primer composition is excellent in transparency and surface hardness.

In particular, aluminum oxide, titanium oxide, zirconium oxide, and antimony oxide are excellent in increasing the refractive index of the primer layer. When a primer layer having a refractive index adjusted by dispersing and containing a fine particle inorganic substance on the surface of a high refractive index plastic lens substrate, interference fringes do not occur. The method for dispersing the fine particle inorganic material is to mix the dispersion (fine particle inorganic material) and the vehicle component (a substance serving as a substrate, here polyvinyl acetal, a cross-linking agent, an acid catalyst, etc.) in a volatile dispersion solvent, The most preferred method is to evaporate the volatile dispersion medium. What is important in this method is to note the compatibility of the dispersion and vehicle components. The finely divided inorganic material that is a dispersion is generally sensitive to acids, alkalis, surfactants, etc., and if it is not compatible with these environments, the finely divided inorganic material is solidified or the dispersion-vehicle component mixed solution is It causes problems such as thickening. The cause of solidification or thickening is a method of mixing the dispersion and the vehicle component.
If the stirring is insufficient, the dispersion is not uniformly dispersed in the solution, and a phenomenon such as partial coagulation or thickening is likely to occur.
It is desirable to gradually add the dispersion while stirring using a rotor and a magnetic stirrer.

When the primer composition according to the present invention is prepared, the fine particle inorganic material exhibits good dispersion characteristics, solidification,
The problem of thickening did not occur. Particulate inorganic matter is
Although a fine powder may be used, a commercially available fine particle inorganic sol dispersed in water or an organic solvent is used. The average particle size of the fine particles is desirably about 1 to 300 nm, preferably 1 to 50 nm. 1 nm
If it is less than 3, it is difficult to expect an improvement in the refractive index of the primer layer.
If the thickness exceeds 00 nm, the primer layer is likely to diffusely reflect and the intensity of scattered light increases, so that a clouding phenomenon occurs.

In the present invention, the addition amount of the finely divided inorganic material comprising the metal oxide contained in the primer composition is
It is 5 to 200% by weight based on the solid content of the polyvinyl acetal resin. This addition amount is determined in consideration of the thermal expansion coefficient and refractive index of the plastic substrate used and the thermal expansion coefficient and refractive index of the hard coat layer. The amount of addition may be adjusted so that the coefficient of thermal expansion of the cured primer layer is approximately in the middle of the plastic lens substrate and the hard coat layer, and the refractive index is approximately the same as both.

As the volatile dispersion medium, hydrocarbons, halogenated hydrocarbons, alcohols, ketones, esters, ethers and other known solvents can be used, and these solvents can also be used. May be used alone or as a mixture of two or more kinds. When preparing the primer composition, an organic solvent is used to dissolve the polyvinyl acetal, and the solvent for dissolving the polyvinyl acetal resin and the dispersion medium of the particulate inorganic material are the same, or at least those contained in the solvent for dissolving the resin. One kind is more preferable.

In addition to containing pure water in the primer composition, various leveling agents for the purpose of improving the surface condition at the time of applying the primer, or ultraviolet absorbers and antioxidants for improving the weather resistance, and dyes It is also possible to add a pigment, a photochromic dye or the same pigment, and other additives for enhancing an additional function or adding a new function. For details of adding pure water and a leveling agent, Japanese Patent Application No. 7-002288 and Japanese Patent Application No. 7-0009.
03 disclosed.

The primer composition prepared under the above conditions is formed on the surface of the plastic lens substrate by spin coating or dipping. The film thickness is 0.5-3μ
m is preferable, and 1 to 2 μm is more preferable. When forming the primer layer, the plastic lens substrate is surface-treated in order to improve the adhesion between the plastic lens substrate and the primer layer. Surface treatment methods generally include “saponification treatment” and “plasma treatment”. Saponification is a plastic lens from which large dust has been removed (known as shaving), and an approximately 10 wt% sodium hydroxide solution,
Immerse for about 5 minutes under the condition of about 60 ° C., then pre-wash with water, and further wash in a washing process composed of a surfactant, pure water and the like.

On the other hand, the plasma treatment is a method in which the surface of a plastic lens substrate is placed in contact with oxygen plasma, and the plastic surface is reacted with oxygen ions or oxygen radicals in the plasma to modify the surface. In addition to the surface treatment method, there is also a method in which a substance having an effect of improving adhesion is formed on the surface of the substrate. This material includes silane coupling agents and titanium coupling agents.

A hard coat layer can be provided on the primer layer as a scratch resistant film. As a method for forming the hard coat film, a wet method in which a hydrolyzate of organoalkoxysilane, metal oxide fine particles, and a hard coat solution in which a metal complex catalyst is dissolved are applied by a dipping method or a spin coat method and then heat-cured Alternatively, a known method such as a dry method such as a chemical vapor deposition method (also referred to as a CVD method) can be used.

The dry method is particularly excellent in scratch resistance because the surface hardness thereof is higher than that of the wet method film, and it is not necessary to consider the erosion of the lower layer substance unlike the wet method, and the dry method has a wider range of materials. Can be multi-layered. This film forming method is a technology that has rapidly developed with the progress of semiconductor manufacturing technology, and has been actively developed in recent years for application to other fields. The dry method uses a vapor deposition method, a sputtering method, a chemical vapor deposition method (also referred to as a CVD method), or the like, and a low temperature plasma CVD method seems to be suitable among them. A silane-based gas (monosilane, dichlorosilane, etc.) and hydrogen gas, nitrogen gas, ammonia gas, etc. are mixed as a material gas in a sample chamber at a constant flow rate ratio to form a film of SiOx, SiNx or the like. The gas reaction temperature is 80 to 1 considering the influence on the plastic substrate.
The film was formed at about 00 ° C. As explained above,
The hard coat layer formed by the low temperature plasma CVD method is characterized in that it is denser and harder than the organic hard coat layer. Therefore, the residual film stress of the CVD film is extremely large, and the linear thermal expansion coefficient is an order of magnitude smaller than that of the plastic substrate or the primer layer. These film residual stress and thermal stress (linear thermal expansion coefficient) greatly depend on the film structure. Since the film formation conditions have a great influence on the film structure, it is very important to set the film formation conditions. This is because the film residual stress and thermal stress of the hard coat layer greatly affect the heat resistance and impact resistance of the plastic lens.

The antireflection film is a single layer based on optical theory.
A multi-layered film is adopted. As the material, Si
O, SiO₂, Al₂O₃, Y₂O₃, Yb₂O₃, CeO₃,
Ta ₂O₃, TiO₂, MgF₂, ZrO₂Inorganic dielectric such as
Body is used, vacuum deposition method, sputtering method, ion
A film is formed by a plating method or the like. If necessary,
The purpose is to prevent dirt from adhering to the upper layer of the anti-reflection film layer and to prevent water stains.
As a side chain, alkyl group, phenyl group, polyfluoro
Organosilicon compounds with hydrophobic groups such as alkyl groups
Forming ultra thin films of fluorinated hydrocarbon compounds
Is also possible.

[0048]

The primer composition according to the present invention has a long usable time (pot life) and can be cured by heating at a relatively low temperature for a short time to form a film having excellent adhesion and smoothness. it can. Since the primer layer in the present invention has a high degree of elasticity and a high degree of flexibility, it plays a role of absorbing the energy of the plastic lens when it is impacted by some kind.

Further, since the primer layer in the present invention has a three-dimensional crosslinked structure, when the hard coat layer is formed by the wet method, polyvinyl acetal and other substances are dissolved in the hard coat liquid to form the hard coat liquid. It does not pollute. Further, a suitable hydroxyl group of polyvinyl acetal, which is the main component of the primer composition in the present invention, achieves sufficient adhesion between the primer layer and the plastic lens by hydrogen bonding with the polar group on the surface of the plastic lens, and thus the polyvinyl acetal has an appropriate level of adhesion. It is considered that sufficient adhesion between the primer layer and the hard coat layer is achieved by the reaction between the hydroxyl group and the silanol group in the hard coat layer.

Since the primer composition according to the present invention disperses and contains the fine-particle inorganic material responsible for adjusting the refractive index, interference fringes do not occur even if it is provided between the plastic lens substrate and the hard coat layer. Even when the primer layer according to the present invention is provided on the surface of a low refractive index plastic lens substrate, not only impact resistance and scratch resistance but also heat resistance is remarkably improved. This is because the thermal characteristics of the primer layer are almost intermediate between the thermal characteristics of the plastic lens substrate and the hard coat layer, so that the thermal stress of the plastic lens substrate can be suppressed to a minimum.

[0051]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited to these examples. Example 1 (1-1) Preparation of Primer Composition Commercially available degree of butyralization is about 25%, average degree of polymerization is 2,400.
Polyvinyl butyral resin (manufactured by Wako Pure Chemical Industries, Ltd.) 70 parts by weight is dissolved in 630 parts by weight of n-butanol to prepare a dispersion of antimony pentoxide fine particles in a methanol solvent (Nissan Chemical Co., Ltd.).
150 parts by weight) are gradually added. A rotor and a magnetic stirrer were used for stirring. Further, 100 parts by weight of water, 8.5 parts by weight of methyltrimethoxylane as a cross-linking agent, 1.2 parts by weight of p-toluenesulfonic acid as a curing catalyst, and 1 part by weight of Florard FC430 as a leveling agent were sequentially added. The mixture was sufficiently stirred until it became uniform and then filtered through a 0.2 μm membrane filter to prepare a coating primer composition. The refractive index of the prepared primer composition was about 1.48.

(1-2) Application and curing of primer composition NLIII (Nikon product name) plastic lens for eyeglasses having a diopter of -4.25 diopters, a center thickness of 1.0 mm and a refractive index of 1.61. First, plasma treatment was performed for the purpose of enhancing the adhesion of the primer layer. For processing, Yamato Scientific Co., Ltd. "Plasma Reactor PR501A" is used.
The conditions are oxygen gas pressure of about 0.2Toor and RF output.
The processing time was 200 W and the processing time was 30 seconds. Then, the primer composition prepared in (1-1) was applied on the concave surface of the high refractive index plastic lens by spin coating. The spin coating conditions were a primary rotation speed of 500 rpm for 5 seconds, a secondary rotation speed of 2,000 rpm for 10 seconds, and a primer layer thickness of about 1 μm. Then, the high-refractive-index plastic lens coated with the primer is put into a heating furnace and heated to 90 ° C.
And heat-treated for 30 minutes to cure the primer composition. The refractive index of the cured primer layer was about 1.60.

(1-3) Preparation of organosilane-based high-refractive-index hard coat liquid 180 parts by weight of γ-glycidoxypropyltrimethoxysilane were charged into a reaction vessel equipped with a rotor, and a magnetic stirrer was used. While stirring thoroughly, 0.0
40 parts by weight of 1N aqueous hydrochloric acid solution was added at once. Although it was a heterogeneous solution immediately after the addition, it became a homogeneous and transparent solution while generating heat in a few minutes. The mixture was further stirred for 1 hour for hydrolysis to obtain a partially condensed hydrolyzate.

To the above hydrolyzate, commercially available tin oxide sol (methanol dispersion system, average particle size 10 to 15 nm) was added.
30 parts by weight, 4 parts by weight of ethylenediaminetetraacetic acid aluminum as a curing catalyst, and 0.45 parts by weight of Florard FC430 which is a silicon-based surfactant as a leveling agent were added, and after sufficiently stirring, filtered with a 3 μm membrane filter. Then, a hard coat solution was prepared. The prepared hard coat liquid had a refractive index of about 1.49.

(1-4) Application and Curing of Hard Coat Liquid The organosilane-based hard coat liquid obtained in (1-3) is applied to both sides of the plastic lens having the primer layer obtained in (1-2). Dipping method (Pulling speed 1
(00 cm / min). 8 coated lenses
The hard coat layer was cured by heat treatment at 0 ° C. for 4 hours. The cured hard coat layer had a refractive index of about 1.60.

(1-5) Formation of Antireflection Film A five-layer antireflection film composed of silicon dioxide and zirconium oxide was formed on both surfaces of the plastic lens having the primer layer and the hard coat layer obtained in (1-4). It was formed by a vacuum evaporation method. (1-6) Performance evaluation of the plastic lens having the above-mentioned composite film Having the obtained primer layer, further having both a hard coat layer and an antireflection layer (hereinafter referred to as "composite film")
The following is the evaluation of the performance of the plastic lens

The method was used. The evaluation results are shown in Table 1. 1) Adhesion of the primer layer to the substrate In order to evaluate the adhesion of the film, a crosshatch tape test was carried out according to the JIS standard as follows. A 1 mm square grid pattern (10 mm) on the surface of the coating layer with a cutter knife.
After making 0 squares, and then strongly sticking cellophane adhesive tape (product name “Cellotape” Nichiban Co., Ltd.),
Holding one end of the tape and peeling off the tape vigorously in the 90 ° direction was repeated 10 times. After that, the number of grid-shaped cellophane tapes on the surface of the coating layer that remained without being peeled off from the lens surface was counted, and the number of grid-shaped tapes that were not peeled off was expressed as "X". In this case, the larger X is, the better the adhesion is. That is, if the result of the crosshatch tape test is "100", it means that the primer layer was not peeled at all.

2) Scratch resistance A plastic lens surface having a primer layer, a hard coat layer and an antireflection film in that order from the substrate side was rubbed with steel wool (# 0000) under a load of 600 g for 30 times. The condition of scratches was evaluated according to the following criteria. A: The scratched area is within 10%.

B: The scratched area exceeds 10% and within 30%. C: The scratched area is 30% or more. 3) Impact resistance The impact resistance of the plastic lens having the primer layer, the hard coat layer, and the antireflection film in order from the base material side was evaluated by the hard-ball drop test. 127 cm using a 20.0 g hard sphere, which is about 26% heavier than the conditions specified by the FDA.
From the height of the lens toward the center of the plastic lens, and the number of times before the plastic lens cracks or cracks is used as a guide for the impact resistance of the lens.
Dropped up to 5 times.

4) Heat resistance The heat resistance of a plastic lens having a composite film consisting of a primer layer, a hard coat layer and an antireflection film in order from the base material side was evaluated by the crack generation temperature in a high temperature environment and its appearance and its change with time. It evaluated from. Specifically, a plastic lens with a composite film is placed in a constant temperature oven.
After leaving it for 0 minutes, it was taken out in a room temperature environment, and the presence or absence of cracks at that time, the thickness of the cracks and the change with time were examined. The evaluation was performed according to the following criteria. The fine cracks are those that can be confirmed to be cracked but disappear after standing for 15 minutes, and the medium-sized cracks are those that do not disappear even after standing for 15 minutes after confirming the occurrence of cracks.

A: No crack was generated in the environment at 100 ° C. for 10 minutes. B: Fine cracks were generated in an environment of 100 ° C. for 10 minutes. C: Medium-sized cracks were generated at 100 ° C. for 10 minutes. 5) Weather resistance The weather resistance of the plastic lens having the primer layer, the hard coat layer, and the antireflection film in order from the base material side is 300 hours using a UV long life fade meter (manufactured by Suga Test Instruments Co., Ltd.). A test was conducted and the degree of yellowing of the lens was measured thereafter. The evaluation was performed according to the following criteria.

A: Yellowing degree after 300 hours is less than 2.0 B: Yellowing degree after 300 hours is 2.0 or more and less than 2.5 C: Yellowing degree after 300 hours is 2.5 or more 6) Chemical resistance The chemical resistance of a plastic lens having a primer layer, a hard coat layer, and an antireflection film in order from the base material side is pH 1
Of the hydrochloric acid aqueous solution and the sodium hydroxide aqueous solution of pH 12 were immersed in each solution for 8 hours, and then the state change of the surface of the plastic lens was examined. The evaluation was performed according to the following criteria.

A: Not affected by both acidity and alkalinity. B: Corroded by either acidity or alkalinity. C: Attacked by both acidity and alkalinity. 7) Appearance Regarding the appearance of the plastic lens having the primer layer, the hard coat layer, and the antireflection film in order from the base material side, the transparency was visually observed by shining light of a fluorescent lamp in a dark room. The evaluation was performed according to the following criteria.

A: No cloudiness B: Some cloudiness is noticeable C: Cloudiness is clearly noticeable [Example 2] (2-1) Preparation of primer composition Commercially available butyralization degree about 70%, average polymerization degree 700 polyvinyl butyral resin (Wako Pure Chemical Industries, Ltd.) 70 parts by weight dissolved in n-butanol 630 parts by weight, and 300 parts by weight of a methanol-solvent dispersion product (manufactured by Nissan Chemical Co., Ltd.) of a composite sol composed of fine particles of tin oxide and fine particles of tungsten oxide. Is gradually added. A rotor and a magnetic stirrer were used for stirring. Further, 100 parts by weight of water, 8.5 parts by weight of methyltrimethoxylane as a cross-linking agent, and p as a curing catalyst.
-Toluenesulfonic acid (1.2 parts by weight) and Florard FC430 (1 part by weight) as a leveling agent were sequentially added, and the mixture was sufficiently stirred until it became 0.2 μm.
The membrane was filtered with a membrane filter of No. 1 to prepare a coating primer composition. The refractive index of the prepared primer composition was about 1.46.

(2-2) Coating and curing of primer composition NLIII (Nikon product name) GLIII eyeglass plastic lens having a diopter of -3.25 diopters, a center thickness of 1.0 mm and a refractive index of 1.61. First, similarly to (1-1), a plasma treatment was performed for the purpose of enhancing the adhesion of the primer layer. Then, the primer composition prepared in (2-1) was applied on the concave surface of the treated high refractive index plastic lens by spin coating. Spin coating condition is primary rotation speed 500
The rpm was 5 seconds, the secondary rotation speed was 2,000 rpm for 10 seconds, and the primer layer thickness was approximately 1 μm. afterwards,
The high refractive index plastic lens coated with the primer was placed in a heating furnace and heat-treated at 90 ° C. for 30 minutes to cure the primer composition. The refractive index of the cured primer layer was about 1.59.

(2-3) Preparation of organosilane-based high-refractive-index hard coat liquid (1-3) A high-refractive-index hard coat liquid was prepared with the same composition and method. (2-4) Application and curing of hard coat liquid (1-4) The hard coat liquid was applied and cured under the same method and conditions. (2-5) Formation of Antireflection Film An antireflection film was formed by the same method and conditions as in (1-5).

(2-6) Performance evaluation of plastic lens having composite film

The same performance evaluation as in (1-6) was performed. The evaluation results are shown in Table 1. Example 3 (3-1) Preparation of Primer Composition 70 parts by weight of a commercially available polyvinyl butyral resin having a degree of butyralization of about 70% and an average degree of polymerization of 700 (manufactured by Wako Pure Chemical Industries, Ltd.) was added with 630 parts by weight of n-butanol. Dissolved in the solvent, silicon dioxide particles methanol solvent dispersion product (manufactured by Nissan Chemical Co., Ltd.) 50
Add parts by weight slowly. At this time, the mixture was added with thorough stirring using a rotor and a magnetic stirrer. Furthermore, 100 parts by weight of water, 8.5 parts by weight of methyltrimethoxysilane as a cross-linking agent, 1 part by weight of glutaraldehyde, 1.2 parts by weight of p-toluenesulfonic acid as a curing catalyst, and 1 part by weight of Florard FC430 as a leveling agent are sequentially added. In addition, the mixture was sufficiently stirred until it became homogeneous, and then filtered through a 0.2 μm membrane filter to prepare a coating primer composition. The refractive index of the prepared primer composition was about 1.41.

(3-2) Application and Curing of Primer Composition DXII (Nikon product name) DXII plastic lens with a diopter of -4.00 diopters, a center thickness of 1.0 mm and a refractive index of 1.56. First, plasma treatment was performed to enhance the adhesion of the primer layer. The conditions of plasma treatment are as follows: Argon gas pressure about 0.2Toor, RF output 200
W, processing time was 30 seconds.

Then, hexamethyldisilazane, which is a silane coupling agent, was formed on the plastic lens substrate for the purpose of reinforcing the adhesion of the primer to the substrate. For film formation, the plastic lens substrate was placed for 3 minutes in an atmosphere of hexamethyldisilazane at 110 ° C. at about 1 Torr. The primer composition prepared in (3-1) was applied onto the concave surface of the surface-treated medium refractive index plastic lens by spin coating. The spin coating conditions are: a primary rotation speed of 500 rpm for 5 seconds, a secondary rotation speed of 2,
The primer layer thickness was set to about 1.5 μm at 000 rpm for 10 seconds. Then, the medium refractive index plastic lens coated with the primer composition is put in a heating furnace,
The primer composition was cured by heat treatment at 30 ° C. for 30 minutes.

The refractive index of the cured primer layer was about 1.54. (3-3) Preparation of organosilane-based low-medium refractive index hard coat liquid 180 parts by weight of γ-glycidoxypropyltrimethoxysilane was charged into a reaction vessel equipped with a rotor, and the mixture was thoroughly stirred using a magnetic stirrer. While 0.0
40 parts by weight of 1N aqueous hydrochloric acid solution was added at once. Although it was a heterogeneous solution immediately after the addition, it became a homogeneous and transparent solution while generating heat in a few minutes. The mixture was stirred for 1 hour for hydrolysis to obtain a partially condensed hydrolyzate.

Commercially available silica sol (manufactured by Nissan Kagaku Co., Ltd., methanol dispersion, average particle diameter 10 to 10) is used as the above hydrolyzate.
20 nm) and 630 parts by weight, 4 parts by weight of acetylacetone aluminum as a curing catalyst, and 0.45 parts by weight of Florard FC430, which is a silicon-based surfactant as a leveling agent, are added and sufficiently stirred, and then a 3 μm membrane filter is used. It filtered and prepared the hard-coat liquid. The prepared hard coat liquid had a refractive index of about 1.44.

(3-4) Application and Curing of Hard Coat Liquid The organosilane-based hard coat liquid obtained in (3-3) is applied to both sides of the plastic lens having the primer layer obtained in (3-2). Spin coating method (Primary rotation speed 50
5 seconds at 0 rpm, 10 seconds at 1,000 rpm
The coating was applied to one side for 2 seconds, and then cured, and then applied to the other side and cured again. The curing conditions were heat treatment at 80 ° C. for 4 hours. The cured hard coat layer had a refractive index of about 1.53.

(3-5) Formation of Antireflection Film An antireflection film was formed by the same method and conditions as in (1-5). (3-6) Performance evaluation of plastic lens having composite film

The same performance evaluation as in (1-6) was performed. The evaluation results are shown in Table 1. [Comparative Example 1] (Comparative 1-1) Preparation of Primer Composition 70 parts by weight of a commercially available polyvinyl butyral resin having a degree of butyralization of about 25% and an average degree of polymerization of 700 (manufactured by Wako Pure Chemical Industries, Ltd.) was n-butanol 630. It was dissolved in 1 part by weight and stirred thoroughly. Further, 100 parts by weight of water, 8.5 parts by weight of γ-glycidoxypropyltrimethoxysilane as a crosslinking agent, 1 part by weight of glutaraldehyde, 1.2 parts by weight of p-toluenesulfonic acid as a curing catalyst, and Florard FC430 as a leveling agent. 1 part by weight was sequentially added, and the mixture was sufficiently stirred using a rotor and a magnetic stirrer until the mixture became uniform, and then filtered through a 0.2 μm membrane filter to prepare a coating primer composition. The refractive index of the prepared primer composition was about 1.38.

(Comparative 1-2) Application and curing of primer solution (3-2) Application and curing of the primer composition were carried out under the same method and conditions. (Comparative 1-3) Preparation of organosilane-based low refractive index hard coat liquid (3-3) A low refractive index hard coat liquid was prepared with the same composition and method. (Comparative 1-4) Application and curing of hard coat liquid (3-4) The hard coat liquid was applied and cured by the same method and conditions.

(Comparative 1-5) Formation of Antireflection Film (1-5) An antireflection film was formed by the same method and conditions. (Comparison 1-6) Performance evaluation of plastic lens with composite film

(1-6) The same performance evaluation was performed. The evaluation results are shown in Table 1.

[0079]

[Table 1]

[0080]

The plastic lens obtained by applying the primer layer obtained by the present invention by the predetermined method has the following effects. (1) Even a thin and light plastic lens such as an aspherical designed lens can pass the US FDA impact test and can be provided with a plastic lens that is less likely to break than conventional products and is less likely to crack even in a high temperature environment.

(2) Since not only impact resistance but also heat resistance is remarkably improved, it can withstand use in a considerably severe thermal environment. Therefore, it is possible to provide the market with a plastic lens and a panel that are not easily scratched and are thermally stable. (3) A primer composition having any refractive index can be prepared by adjusting the addition ratio of the fine particle inorganic material, and impact resistance is significantly improved. Therefore, there is no problem in appearance and heat resistance of the high refractive index plastic lens. We can provide thinner, lighter and more durable plastic lenses that pass US FDA impact test.

In recent years, the need for further improving the scratch resistance and abrasion resistance of the hard coat layer applied to the plastic lens has increased, and a hard coat layer having a new composition or a new structure has been developed. . This next-generation hard coat layer is being developed in the direction of further densification, and the thermal behavior of the plastic lens substrate and the hard coat layer will be far from each other, and the heat resistance will be further reduced. become. Even in such a case, by providing the primer layer according to the present invention, it is possible to provide a lens having improved heat resistance as well as impact resistance and scratch resistance.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display location G02C 7/02 G02B 1/10 A

Claims (8)

[Claims] 1. At least (A) the general formula (I): (However, in the formula, R ¹ is a hydrogen atom or a carbon number of 1 to 20.
Is a saturated hydrocarbon group, a is a fraction of a structural unit having an acetal group of 10 to 90, b is a fraction of a structural unit having an OH group of 10 to 90, and c is a structural unit having an acetyl group. Is a fraction of 0 to 10, and a + b + c = 1
00. ) Polyvinyl acetal represented by
(B) General formula (II) (However, in the formula, R ² and R ³ are substituted or unsubstituted hydrocarbon groups having 1 to 8 carbon atoms, X ¹ is a hydrolyzable group, and d and e are integers from 0 to 3. .) A hydrolyzable organosilane compound or a hydrolyzate thereof, or a compound represented by the general formula (III): (In the formula, R ⁴ is an organic group having 2 to 8 carbon atoms, R ⁵ and R ⁶ are substituted or unsubstituted hydrocarbon groups having 1 to 8 carbon atoms, and X ² is a hydrolyzable group. And f and g are 0
It is an integer from 1 to 2. ) A hydrolyzable organosilane compound or a hydrolyzate thereof, or a general formula (IV): (In the formula, R ⁷ is a substituted or unsubstituted C 1 to C 6
Is a hydrocarbon group. ) Or a dialdehyde compound or glyoxal represented by the general formula (V) (However, in the formula, R ⁸ is a substituted or unsubstituted C 1 to C 6
A hydrocarbon group, R ⁹ is a saturated hydrocarbon group having 1 to 4 carbon atoms. ) A dialdehyde acetal compound represented by the formula (1), a primer composition comprising at least one cross-linking agent selected from the group consisting of: (C) a particulate inorganic material; and (D) an organic solvent and water, The content of the polyvinyl acetal which is the component (A) is 1 to 30% by weight, the content of the crosslinking agent which is the component (B) is 0.01 to 30% by weight, and the fine particles which are the component (C). A primer composition comprising 10 to 80% by weight of a particulate inorganic substance. 2. The primer composition has 0.002-
The primer composition according to claim 1, which comprises 20% by weight of a curing catalyst dispersed therein. 3. The primer composition according to claim 1, wherein the polyvinyl acetal is polyvinyl butyral. 4. The primer composition according to claim 1, wherein the hydrolyzable organosilane is an alkoxysilane compound whose hydrolyzable group is an alkoxy group having 1 to 4 carbon atoms. 5. The fine-particle inorganic material has an average particle diameter of 1
~ 300 nm at least one or two kinds selected from aluminum oxide, iron oxide, silicon dioxide, cerium oxide, tungsten oxide, molybdenum oxide, titanium oxide, zirconium oxide, tin oxide, antimony oxide, zinc oxide, beryllium oxide. The primer composition according to claim 1, which is a combination of the above. 6. A plastic lens in which a hard coat layer is provided on both surfaces of a plastic lens substrate, wherein a particulate inorganic substance is dispersed and contained between at least one surface of the plastic lens substrate and the hard coat layer. And a plastic lens provided with a primer layer made of a cross-linked polyvinyl acetal resin. 7. The plastic lens according to claim 6, wherein an antireflection film is provided on the hard coat layer. 8. The average particle size of the fine particle inorganic material is 1
~ 300 nm aluminum oxide, iron oxide, silicon dioxide, cerium oxide, tungsten oxide, molybdenum oxide, titanium oxide, zirconium oxide, tin oxide, antimony oxide, zinc oxide, beryllium oxide selected from at least one or two kinds. The plastic lens according to claim 6 or 7, which is a combination of the above.