JPH08106001A - Plastic lens - Google Patents

Abstract

PURPOSE: To attain excellent transparency and adhesivity of a plastic lens base material to a hardened film of an organic silane resin by providing a hard coat layer composed of the organic silane resin directly on the surface of the specific plastic lens base material. CONSTITUTION: This plastic lens is formed by providing the hard coat layer composed of the organic silane resin directly on the plastic lens base material composed of a transparent resin obtained by polymerizing a monomer consisting of a monomer containing an alkylene oxide expressed by a formula, R1 -O-(R<2> O)n - R3 as an indispersable constituents. In the formula, R1 is a vinyl group, an allyl group, a methally group, an acryloyl group or a methacryloyl group, R2 is hydrogen, a vinyl group, an allyl group, a methallyl group, an acryloyl group, a methacryloyl group or the other 1-40C univalent hydrocarbon group, (n) is integers of 2-50. Then, the plastic lens is formed by applying the organic silane based hard coat layer directly on the lens base material without surface treating.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a plastic lens coated with an organic silane hard coat film.

[0002]

2. Description of the Related Art Conventionally, materials for optical lenses include acrylic resins having high transparency, diethylene glycol bisallyl carbonate resin (for example, CR-39), polystyrene, and the like.
Polycarbonate and the like are used, but among these, a lens that uses diethylene glycol bisallyl carbonate, which is a thermosetting resin, is widely used as a spectacle lens. The reason is that it is excellent in transparency, low dispersibility (high Abbe number), heat resistance and impact resistance.

However, the lens using diethylene glycol bisallyl carbonate has a problem that the refractive index is as low as 1.50 and the thickness of the lens is larger than that of the glass lens (particularly, it is remarkable when the lens power is large). . Further, it is inferior in scratch resistance like general plastics. For this reason, a method of coating the lens surface with an organic silane-based hard coat film has been proposed, but in the untreated state, uniform adhesion to the organic silane-based hard coat film is insufficient. Therefore, the surface of the plastic lens cannot be coated with the organic silane-based hard coat film unless the surface of the plastic lens is treated by any method.

Recently, there has been a strong demand for thinner and lighter spectacle lenses, and development of materials for spectacle lenses having a high refractive index has been actively pursued. For example, JP-A-56-166214 proposes a copolymer of dimethacrylate having a nuclear halogen-substituted aromatic ring and a monofunctional monomer having an aromatic ring. This material is
Although it has a high refractive index, it has a problem that the specific gravity becomes large because the halogen group is contained in the resin skeleton. Further, JP-A-63-46213 proposes a copolymer of polyisocyanate and polythiol. This material has high refraction, but has a problem of low heat resistance. Furthermore, these materials have insufficient uniform adhesion to the organic silane-based hard coat film, and therefore cannot be coated with the organic silane-based hard coat film unless surface-treated by any method.

On the other hand, examples of high-refraction thermoplastic resins include polystyrene (refractive index 1.58, Abbe number 31) and polycarbonate (refractive index 1.58, Abbe number 30). Although they have a high refractive index, they have a problem that the chromatic aberration is large due to a low Abbe number, the former has low heat resistance, and the latter has low surface hardness and is easily scratched. further,
Since these materials have strong water repellency, their adhesiveness to the organic silane-based hard coat film is particularly low. Therefore, it is necessary to coat the organic silane-based hard coat film after increasing adhesion to the hard coat film by forming a primer layer on the lens surface.

Further, as resins having improved heat resistance and Abbe's number, there are methyl methacrylate / styrene resin and tricyclomethacrylate [5.2.1.0 ^2,6 ] dec-8-yl / styrene resin ( (See JP-A-62-246001). However, they have a high haze value and low transparency. Moreover, the former has a problem of low heat resistance. Further, these are thermoplastic resins and have a problem in machinability. Furthermore, since these also have low adhesion to the organic silane-based hard coat film, it is possible to coat the organic silane-based hard coat film without increasing the hard coat adhesion on the lens surface by providing a primer layer or the like. Can not.

Further, JP-A-62-232414 proposes a copolymer of tricyclo [5.2.1.0 ^2,6 ] deca-8-yl / styrene / crosslinkable polyfunctional monomer. Has been done. This material has an insufficient haze and has a problem in transparency. Further, since the adhesiveness to the organic silane-based hard coat film is low, it is necessary to increase the adhesiveness to the organic silane-based hard coat film by providing a primer layer or the like.

Further, as a resin having improved adhesion to a hard coat film, a copolymer of aromatic ring-containing dimetha (acrylate) / aromatic ring-containing monomer / hydroxyl group-containing monomer (JP-A-58-58). No. 76410), and copolymers of aromatic ring-containing dimetha (acrylate) / aromatic ring-containing monomer / epoxy group-containing monomer (see JP-A-58-89606). However, although these materials improve the adhesiveness to the glass film when glass is vapor-deposited, the adhesiveness to the organic silane-based hard coat film is not yet satisfactory. Furthermore, the latter is not preferable from the viewpoint of moldability because the adhesiveness of the cast polymerization to the glass mold increases excessively as the copolymerization amount of the epoxy group-containing monomer in the resin increases.

Further, in JP-A-3-136002, a di (meth) acrylate containing a nuclear halogen-substituted aromatic ring and an alkylene glycol group / an aromatic ring-containing monomer /
A copolymer of a compound containing an aromatic ring and an epoxy group has been proposed. Although this material improves the adhesiveness to the organic silane-based hard coat film, the adhesiveness to the glass mold of the cast polymerization excessively increases as the copolymerization amount of the epoxy group-containing monomer in the resin increases. Therefore, it is not preferable in terms of moldability.

Further, in Japanese Patent Laid-Open No. 5-5011,
Copolymers of styrene derivatives / ethylene glycol dimethacrylate / specific diacrylate compounds / specific epoxy modified di (meth) acrylate have been proposed. Although this material improves the adhesiveness to the organic silane-based hard coat film when the primer is used, the adhesiveness to the organic silane-based hard coat film when the primer is not used is still unsatisfactory.

[0011]

As described above, the specific gravity has been low so far, the physical properties required for plastic lenses have been obtained, and the organosilane-based hard coat is directly applied to the lens substrate without surface treatment. There was no plastic lens coated.

An object of the present invention is, firstly, to provide a plastic lens in which an organic silane-based hard coat film is directly applied to a lens substrate without subjecting it to a surface treatment, and secondly, to the above-mentioned characteristics. In addition, the present invention provides a plastic lens having excellent machinability and high heat resistance. Thirdly, in addition to these characteristics, the specific gravity is further smaller, and the low dispersion (high Abbe number) and high refractive index are excellent. To provide plastic lenses.

[0013]

The plastic lens according to the present invention is represented by the chemical formula 2 [general formula (I)].

Embedded image R ₁ —O— (R ₂ O) n—R ₃ ... (I) (wherein R ₁ is a vinyl group, an allyl group, a methallyl group, an acryloyl group or a methacryloyl group, and R ₂ is a carbon number. 1 to 40 divalent hydrocarbon group, R ₃ is hydrogen, vinyl group, allyl group, methallyl group, acryloyl group, methacryloyl group, or 1 to 40 carbon atoms other than these.
Which is a valent hydrocarbon group and n is an integer of 2 to 50), and is a plastic made of a transparent resin obtained by polymerizing a monomer containing an alkylene oxide group-containing monomer as an essential component. A hard coat layer made of an organic silane resin is directly provided on the surface of the lens substrate.

As the above-mentioned monomer containing an alkylene oxide group represented by the general formula (I), R ₂ in the general formula (I) is a divalent hydrocarbon group having 1 to 5 carbon atoms. Monomers are preferred. Since the hydrophobicity becomes stronger as the carbon number of R ₂ increases, the adhesion between the transparent resin and the hard coat layer is likely to decrease, so that R in the general formula (I)
Divalent hydrocarbon group of ₂ is preferably a carbon number in the range of 1-5. For the same reason, R ₃ in the general formula (I) is
When is a monovalent hydrocarbon group, it has 1 to 5 carbon atoms.
It is preferred that

The monomer containing an alkylene oxide group represented by the above general formula (I) includes a monofunctional monomer and a polyfunctional monomer.

Among the monomers having an alkylene oxide group represented by the above general formula (I), monofunctional monomers include diethylene glycol monoacrylate, triethylene glycol monoacrylate, tetraethylene glycol monoacrylate, Polyethylene glycol monoacrylate such as nonaethylene glycol monoacrylate, tetradecaethylene glycol monoacrylate, diethylene glycol monomethacrylate, triethylene glycol monomethacrylate, tetraethylene glycol monomethacrylate, nonaethylene glycol monomethacrylate, tetradecaethylene glycol monomethacrylate, etc. polyethylene Glycol monomethacrylate, methoxydiethylene glycol acrylate, methoki Triethylene glycol acrylate, methoxy tetraethylene glycol acrylate,
Methoxynonaethylene glycol acrylate, methoxytetradecaethylene glycol acrylate, ethoxydiethylene glycol acrylate, ethoxytriethylene glycol acrylate, ethoxytetraethylene glycol acrylate, ethoxynonaethylene glycol acrylate, ethoxytetradecaethylene glycol acrylate and other alkoxy polyethylene glycol acrylate, methoxydiethylene glycol Methacrylate, methoxytriethylene glycol methacrylate, methoxytetraethylene glycol methacrylate, methoxynonaethylene glycol methacrylate, methoxytetradecaethylene glycol methacrylate, ethoxydiethylene glycol dimethacrylate, ethoxytriethyl Glycol methacrylate,
Alkoxy polyethylene glycol methacrylates such as ethoxytetraethylene glycol methacrylate, ethoxynonaethylene glycol methacrylate, ethoxytetradecaethylene glycol methacrylate, dipropylene glycol monoacrylate, tripropylene glycol monoacrylate, tetrapropylene glycol monoacrylate, nonapropylene glycol monoacrylate, tetra Polypropylene glycol monoacrylate such as decapropylene glycol monoacrylate, dipropylene glycol monomethacrylate, tripropylene glycol monomethacrylate, tetrapropylene glycol monomethacrylate, nonapropylene glycol monomethacrylate, tetradecapropylene glycol monomethacrylate Polypropylene glycol monomethacrylate such as tacrylate, methoxydipropylene glycol acrylate, methoxytripropylene glycol acrylate, methoxytetrapropylene glycol acrylate, methoxynonapropylene glycol monoacrylate, methoxytetradecapropylene glycol monoacrylate, ethoxydipropylene glycol acrylate, ethoxytripropylene Alkoxy polypropylene glycol acrylate such as glycol acrylate, ethoxytetrapropylene glycol acrylate, ethoxynonapropylene glycol acrylate, ethoxytetradecapropylene glycol acrylate, methoxydipropylene glycol methacrylate, methoxytripropylene glycol Methacrylate, methoxytetrapropylene glycol methacrylate, methoxynonapropylene glycol monomethacrylate, methoxytetradecapropylene glycol monomethacrylate, ethoxydipropylene glycol dimethacrylate, ethoxytripropylene glycol methacrylate, ethoxytetrapropylene glycol methacrylate, ethoxynonapropylene glycol monomethacrylate, Alkoxy polypropylene glycol methacrylate such as ethoxy tetradeca propylene glycol monomethacrylate, dibutylene glycol monoacrylate, tributylene glycol monoacrylate,
Tetrabutylene glycol monoacrylate, nonabutylene glycol monoacrylate, polybutylene glycol monoacrylate such as tetradecabutylene glycol monoacrylate, dibutylene glycol monomethacrylate, tributylene glycol monomethacrylate, tetrabutylene glycol monomethacrylate, nonabutylene glycol monomethacrylate, Polybutylene glycol monomethacrylate such as tetradecabutylene glycol monomethacrylate, methoxydibutylene glycol acrylate, methoxytributylene glycol acrylate, methoxytetrabutylene glycol acrylate, methoxynonabutylene glycol monoacrylate, methoxytetradecabutylene glycol monoacrylate, Carboxymethyl dibutylene glycol acrylate, ethoxylated tri butylene glycol acrylate, ethoxy tetrabutylene glycol acrylate,
Alkoxy polybutylene glycol acrylates such as ethoxynonabutylene glycol acrylate and ethoxytetradecabutylene glycol acrylate, methoxydibutylene glycol methacrylate, methoxytributylene glycol methacrylate, methoxytetrabutylene glycol methacrylate, methoxynonabutylene glycol monomethacrylate, methoxytetradecabutylene glycol Alkoxy polybutylene glycols such as monomethacrylate, ethoxydibutylene glycol dimethacrylate, ethoxytributylene glycol methacrylate, ethoxytetrabutylene glycol methacrylate, ethoxynonabutylene glycol monomethacrylate, ethoxytetradecabutylene glycol monomethacrylate Tacrylate, ethylene glycol propylene glycol monoacrylate, diethylene glycol propylene glycol monoacrylate, triethylene glycol propylene glycol monoacrylate, tetraethylene glycol propylene glycol monoacrylate, nonaethylene glycol propylene glycol monoacrylate, tetradeca ethylene glycol propylene glycol monoacrylate, ethylene glycol Dipropylene glycol monoacrylate, diethylene glycol dipropylene glycol monoacrylate, triethylene glycol dipropylene glycol monoacrylate, tetraethylene glycol dipropylene glycol monoacrylate, nonaethylene glycol dipropylene glycol Noacrylate, tetradecaethylene glycol dipropylene glycol monoacrylate, ethylene glycol tripropylene glycol monoacrylate, diethylene glycol tripropylene glycol monoacrylate, triethylene glycol tripropylene glycol monoacrylate, tetraethylene glycol tripropylene glycol monoacrylate, nonaethylene glycol triacrylate Polyethylene glycol polypropylene glycol monoacrylate such as propylene glycol monoacrylate, tetradeca ethylene glycol tripropylene glycol monoacrylate, ethylene glycol propylene glycol monomethacrylate, diethylene glycol propylene glycol monomethacrylate, triethylene Glycol Propylene glycol monomethacrylate, tetraethylene glycol propylene glycol monomethacrylate, nonaethylene glycol propylene glycol monomethacrylate, tetradeca ethylene glycol propylene glycol monomethacrylate, ethylene glycol dipropylene glycol monomethacrylate, diethylene glycol dipropylene glycol monomethacrylate, triethylene glycol dimethacrylate Propylene glycol monomethacrylate, tetraethylene glycol dipropylene glycol monomethacrylate,
Nonaethylene glycol dipropylene glycol monomethacrylate, tetradeca ethylene glycol dipropylene glycol monomethacrylate, ethylene glycol tripropylene glycol monomethacrylate, diethylene glycol tripropylene glycol monomethacrylate, triethylene glycol tripropylene glycol monomethacrylate, tetraethylene glycol tripropylene glycol monomethacrylate Examples thereof include polyethylene glycol polypropylene glycol monomethacrylate such as methacrylate, nonaethylene glycol tripropylene glycol monomethacrylate, and tetradecaethylene glycol tripropylene glycol monomethacrylate, and these are used alone or in combination of two or more.

Among the monomers having an alkylene oxide group represented by the general formula (I), polyfunctional monomers include diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, Polyethylene glycol diacrylate such as nonaethylene glycol diacrylate, tetradeca ethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, nonaethylene glycol dimethacrylate, tetradecaethylene glycol dimethacrylate, etc. polyethylene Glycol dimethacrylate, dipropylene glycol diacrylate, tripropylene glycol diacryle Polypropylene glycol diacrylate such as tetrapropylene glycol diacrylate, nonapropylene glycol diacrylate, tetradecapropylene glycol diacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, nonapropylene glycol dimethacrylate Polypropylene glycol dimethacrylate such as tetradecapropylene glycol dimethacrylate, dibutylene glycol diacrylate, tributylene glycol diacrylate, tetrabutylene glycol diacrylate, nonabutylene glycol diacrylate, polybutylene glycol diacrylate such as tetradecabutylene glycol diacrylate Krillet DOO, dibutylene glycol dimethacrylate, triethylene butylene glycol dimethacrylate, tetraethylene butylene glycol dimethacrylate, nona-butylene glycol dimethacrylate,
Polybutylene glycol dimethacrylate such as tetradecabutylene glycol dimethacrylate, diethylene glycol diallyl ether, triethylene glycol diallyl ether, tetraethylene glycol diallyl ether, polyethylene glycol diallyl ether such as pentaethylene glycol diallyl ether, dipropylene Examples include polypropylene glycol diallyl ethers such as glycol diallyl ether, tripropylene glycol diallyl ether, tetrapropylene glycol diallyl ether, and pentapropylene glycol diallyl ether, and these are used alone or in combination of two or more. .

Among the above examples of the alkylene oxide group-containing monomer represented by the general formula (I), among the above-mentioned examples, from the viewpoint of adhesiveness to the organic silane-based hard coat film, a monofunctional monomer is used. As the body, the number of ethylene oxide groups such as tetraethylene glycol monoacrylate, nonaethylene glycol monoacrylate, tetradecaethylene glycol monoacrylate, tetraethylene glycol monomethacrylate, nonaethylene glycol monomethacrylate, and tetradecaethylene glycol monomethacrylate is 4 ~ 14 polyethylene glycol mono (meth) acrylate, methoxytetraethylene glycol acrylate, methoxynonaethylene glycol acrylate, methoxytetradecaethylene glycol acrylate Ethylene oxide such as rate, ethoxynonaethylene glycol acrylate, ethoxytetradecaethylene glycol acrylate, methoxytetraethylene glycol methacrylate, methoxynonaethylene glycol methacrylate, methoxytetradecaethylene glycol methacrylate, ethoxynonaethylene glycol methacrylate, ethoxytetradecaethylene glycol methacrylate The number of carbon atoms in the group is 4 to
14 is an alkoxy polyethylene glycol (meth)
Acrylate and the like are preferable, and as the polyfunctional monomer,
The number of ethylene oxide groups such as tetraethylene glycol diacrylate, nonaethylene glycol diacrylate, tetradecaethylene glycol diacrylate, tetraethylene glycol dimethacrylate, nonaethylene glycol dimethacrylate, and tetradecaethylene glycol dimethacrylate is 4 to 14. Polyethylene glycol di (meth) acrylate and the like are preferable.

Among the above examples, heat resistance, impact resistance,
From the point of dyeability, nonaethylene glycol diacrylate, tetradecaethylene glycol diacrylate,
Polyfunctional monomers such as polyethylene glycol di (meth) acrylate having 9 to 14 ethylene oxide groups such as nonaethylene glycol dimethacrylate and tetradeca ethylene glycol dimethacrylate are particularly preferable.

The amount of the alkylene oxide group-containing monomer represented by the general formula (I) is preferably 1 to 100% by weight based on the total monomers. 1% by weight
If it is less than the above range, the adhesiveness to the organic silane-based hard coat film decreases.

The amount of the alkylene oxide group-containing monomer represented by the general formula (I) is 5% by weight or more based on the total amount of the monomers in order to sufficiently improve the adhesion to the organic silane-based hard coat film. It is preferable to use 30% by weight or less based on the total monomers so that the heat resistance is not lowered and the specific gravity is not increased. Similarly, it is preferable to use 5 to 25% by weight, particularly 5 to 20% by weight, based on all the monomers.

The alkylene oxide group-containing monomer represented by the general formula (I) may be used in combination with other monomers. Specific examples of monofunctional monomers among these other monomers include methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, i-butyl acrylate, t-butyl acrylate, Pentyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, dodecyl acrylate, butoxyethyl acrylate, octadecyl acrylate, phenyl acrylate, benzyl acrylate, naphthyl acrylate, glycidyl acrylate , 2-hydroxyethyl acrylate, acrylic acid esters having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion, acrylic acid esters such as glycerin monoacrylate, methyl methacrylate, ethyl methacrylate, methacrylic acid Propyl, methacrylate n-bu Le, i- butyl methacrylate, t- butyl methacrylate, pentyl methacrylate,
N-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, dodecyl methacrylate, butoxyethyl methacrylate, octadecyl methacrylate, phenyl methacrylate, benzyl methacrylate, naphthyl methacrylate, glycidyl methacrylate,
2-Hydroxyethyl methacrylate, methacrylic acid ester having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion, methacrylic acid ester such as glycerin monomethacrylate, styrene, α-methylstyrene, α-
Aromatic vinyl compounds such as ethylstyrene, α-fluorostyrene, α-chlorostyrene, α-bromostyrene, fluorostyrene, chlorostyrene, bromostyrene, methylstyrene and methoxystyrene, N-methylmaleimide, N-ethylmaleimide, N -N-substituted maleimides such as propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, N-phenylmaleimide, N-methylphenylmaleimide, N-chlorophenylmaleimide, N-methoxyphenylmaleimide, N-carboxyphenylmaleimide, etc., Acrylamide, methacrylamide, N dimethyl acrylamide, N-diethyl acrylamide, N-dimethyl methacrylamide,
(Meth) acrylamides such as N-diethylmethacrylamide, calcium acrylate, barium acrylate,
Unsaturation of (meth) acrylic acid metal salts such as lead acrylate, tin acrylate, zinc acrylate, calcium methacrylate, barium methacrylate, lead methacrylate, tin methacrylate, zinc methacrylate, etc., acrylic acid, methacrylic acid, etc. Examples thereof include carboxylic acids, vinyl cyanide compounds such as acrylonitrile and methacrylonitrile, and these are used alone or in combination of two or more.

Among the other monomers which may be used in combination with the alkylene oxide group-containing monomer represented by the general formula (I), specific examples of the polyfunctional monomer include ethylene glycol diacrylate. , Glycerin diacrylate, glycerin triacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, 1,9-nonanediol diacrylate , 1,10-decanediol diacrylate, 1,12-dodecanediol diacrylate, propylene glycol diacrylate, 1-acryloyl-2-hydroxy-3-acryloylpropane,
Pentaerythritol tetraacrylate, 1,1,1
-Trimethylolpropane triacrylate, dipentaerythritol hexaacrylate, hexamethylolmelamine hexaacrylate, N, N ', N "-tris (2-acryloyloxyethyl) isocyanurate,
2,2'-bis [4- (acryloxydiethoxy) phenyl] propane, 2,2'-bis [4- (acryloxydiethoxy) phenyl] methane, bis (acryloxymethyl) tricyclo [5.2.1. 0 ^2,6 ] decane, bis (acryloxymethyl) pentacyclo [6.5.
1 ^3,6 . 0 ^2,7 . 0 ^9,13] pentadecane, bis (acryloxymethyl) heptacyclo [10.5.1.1 ^{3, 10.} 1
^5,8 . 0 ^2,11 . 0 ^4,9 . 0 ^13,17 ] Acrylic esters such as eicosane, ethylene glycol dimethacrylate,
Glycerin dimethacrylate, glycerin trimethacrylate, 1,3-butylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,6
-Hexanediol dimethacrylate, neopentyl glycol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, 1,12-dodecanediol dimethacrylate, propylene glycol dimethacrylate, 1-methacryloyl-2- Hydroxy-3-acryloylpropane, 1-methacryloyl-2-hydroxy-3-methacryloylpropane, pentaerythritol tetramethacrylate, 1,1,1-trimethylolpropane trimethacrylate, dipentaerythritol hexamethacrylate, hexamethylolmelamine hexamethacrylate, N , N ', N "-tris (2-methacryloyloxyethyl) isocyanurate, 2,2'-bis [4- (methacryloxydietoxy) ) Phenyl] propane, 2,2'-
Bis [4- (methacryloxydiethoxy) phenyl]
Methane, bis (methacryloxymethyl) tricyclo [5.2.1.0 ^2,6 ] decane, bis (methacryloxymethyl) pentacyclo [6.5.1, ^3,6 . 0 ^2,7 .
0 ^9,13 ] Pentadecane, bis (methacryloxymethyl)
Heptacyclo [10.5.1.1 ^3,10. 1 ^5,8 .
0 ^2,11 . 0 ^4,9 . 0 ^13,17 ] Methacrylic acid ester such as eicosane, ethylene glycol bisallyl carbonate, diethylene glycol bisallyl carbonate, triethylene glycol bisallyl carbonate, tetraethylene glycol bisallyl carbonate, pentaethylene glycol bisallyl carbonate, polypropylene glycol bisallyl carbonate, Trimethylene glycol bisallyl carbonate, 3-hydroxypropoxy propanol bisallyl carbonate, glycerin bisallyl carbonate, triglycerine bisallyl carbonate, diallyl carbonate, diallylidene pentaerythritol, triallylidene sorbitol,
Diallylidene-2,2,6,6-tetramethylolcyclohexanone, triallylidene hexamethylolmelamine, diarylidene-D-glucose, bisphenol A
Diallyl ether, bisphenol S diallyl ether, ethylene glycol diallyl ether, 1,1,1
-Trimethylolpropane triallyl ether, neopentyl glycol triallyl ether, allyl acrylate, methallyl acrylate, vinyl acrylate, allyl methacrylate, methallyl methacrylate, vinyl methacrylate, diallyl phthalate (diallyl orthophthalate, diallyl isophthalate, diallyl terephthalate and these Examples thereof include a mixture of two or more kinds), an allyl compound such as triallyl isocyanurate and an arylidene compound, and divinylbenzene. These are used alone or in combination of two or more.

Among the above-mentioned other monomers, from the viewpoints of transparency, heat resistance and impact resistance, monofunctional monomers include methyl methacrylate, ethyl methacrylate, propyl methacrylate and n-methacrylate. -Butyl, i-butyl methacrylate, t-butyl methacrylate, pentyl methacrylate, n-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, butoxyethyl methacrylate, phenyl methacrylate, benzyl methacrylate, Methacrylic acid esters such as naphthyl methacrylate, glycidyl methacrylate, methallyl acid esters having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion, aromatic vinyl compounds such as styrene, acrylic acid, methacrylic acid, etc. Unsaturated carboxylic acid and the like are preferable, Examples include divinylbenzene, diallyl phthalate, allyl acrylate, methallyl acrylate, ethylene glycol diacrylate, propylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol. Alkylene glycol having 2 to 12 carbon atoms in the alkylene group such as diacrylate, neopentyl glycol diacrylate, 1,9-nonanediol diacrylate, 1,10-decanediol diacrylate, and 1,12-dodecanediol diacrylate. Diacrylate, allyl methacrylate, methallyl methacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate, 1,3-butylene glycol dimethacrylate Over door,
1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, neopentyl glycol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, 1,12-dodecanediol dimethacrylate Alkylene glycol dimethacrylate in which the number of carbon atoms of the alkylene group such as is 2 to 12 is preferable.

The above ester portion has 5 to 2 carbon atoms.
Specific examples of the methacrylic acid ester or acrylic acid ester having an alicyclic hydrocarbon group of 2 include cyclopentyl methacrylate, cyclohexyl methacrylate, methylcyclohexyl methacrylate, trimethylcyclohexyl methacrylate, norbornyl methacrylate, norbornyl methacrylate. Methyl, isobornyl methacrylate, bornyl methacrylate, menthyl methacrylate, fentyl methacrylate, adamantyl methacrylate, dimethyladamantyl methacrylate, tricyclo [5.2.1.0 ^2,6 ] deca-8-yl, methacrylic acid Methacrylic acid esters such as tricyclo [5.2.1.0 ^2,6 ] deca-4-methyl, cyclodecyl methacrylate, cyclopentyl acrylate, cyclohexyl acrylate, methyl acrylate L-cyclohexyl, trimethylcyclohexyl acrylate, norbornyl acrylate, norbornyl methyl acrylate, isobornyl acrylate, bornyl acrylate, menthyl acrylate, fentyl acrylate, adamantyl acrylate, dimethyl adamantyl acrylate, tricyclo acrylate [5.
Acrylic acid esters such as 2.1.0 ^2,6 ] deca-8-yl, tricyclo [5.2.1.0 ^2,6 ] deca-4-methyl acrylate, cyclodecyl acrylate, etc. are mentioned. Used alone or in combination of two or more. Among these, from the viewpoint of Abbe number, specific gravity and heat resistance, cyclohexyl methacrylate, norbornyl methacrylate, norbornyl methyl methacrylate, tricyclo [5.2.1.0 ^2,6 ] deca-8-yl methacrylate , Tricyclo [5.2.1.0 ^2,6 ] deca-4-methyl and the like are particularly preferable.

Among the above-mentioned polyfunctional monomers, the specific gravity,
From the viewpoint of transparency, heat resistance and impact resistance, divinylbenzene, diallyl phthalate, allyl acrylate, methallyl acrylate, ethylene glycol diacrylate, propylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butane. Diol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate,
The number of carbon atoms of the alkylene group such as 1,9-nonanediol diacrylate, 1,10-decanediol diacrylate and 1,12-dodecanediol diacrylate is 2 to
12 alkylene glycol diacrylate, allyl methacrylate, methallyl methacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate, 1,3-butylene glycol dimethacrylate, 1,4-butanediol dimethacrylate,
The number of carbon atoms of the alkylene group such as 1,6-hexanediol dimethacrylate, neopentyl glycol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, and 1,12-dodecanediol dimethacrylate is 2 Alkylene glycol dimethacrylates of -12 are preferred.

The composition of the monomer containing the alkylene oxide group-containing monomer represented by the general formula (I) as an essential component, that is, the composition of the monomer for producing the transparent resin described above. As, 1 to 30 parts by weight (particularly 5 to 20 parts by weight) of a monomer containing an alkylene oxide group represented by the general formula (I), 15 to 60 parts by weight of styrene (particularly 35 to 55 parts by weight), Methacrylic acid ester or acrylic acid ester having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion, 10 to 70 parts by weight (particularly 10 to 35 parts by weight) and other copolymerizable vinyl monomer 0 ~ 40 parts by weight (particularly 0-10 parts by weight) is 100
It is preferable that the composition is such that it is mixed in parts by weight.

When the amount of styrene used is small, it is difficult to increase the refractive index (particularly, to make the refractive index 1.54 or more), and when the amount is large, it becomes difficult to achieve an optically low dispersion.
In particular, it tends to be difficult to set the Abbe number to 35 or more, and the heat resistance tends to be low.

The above ester portion has 5 to 2 carbon atoms.
When the amount of the methacrylic acid ester or acrylic acid ester having an alicyclic hydrocarbon group of 2 is small, the effect of improving heat resistance is reduced, and when the amount is large, the amount of the methacrylic acid ester or acrylic acid ester having an alicyclic hydrocarbon group is decreased. Unreacted monomers tend to increase and impact resistance tends to decrease.

In the above, when the amount of the other copolymerizable vinyl-based monomer used is increased, it becomes difficult to keep the refractive index large (particularly to keep the refractive index of 1.54 or more), and Keep the specific gravity small (especially if the specific gravity is 1.
It is difficult to keep it below 15).

The use of 0.1 part by weight or more of the unsaturated carboxylic acid, which is one of the other copolymerizable vinyl-based monomers, per 100 parts by weight of the total monomers means that the organic silane-based hard coat film is used. It is preferable for obtaining the effect of improving the adhesiveness to

In the above, the range of use of the polyfunctional monomer is preferably 1 to 50 parts by weight based on 100 parts by weight of all the monomers. If it exceeds 50 parts by weight, the specific gravity tends to be large, and it tends to exceed 1.15. If it is less than 1 part by weight, problems such as heat resistance and machinability tend to occur. The range of use of the polyfunctional monomer is preferably 3 to 40 parts by weight, 7 to 35 parts by weight, and 10 to 30 parts by weight with respect to 100 parts by weight of all the monomers. .

The above-mentioned transparent resin has a low specific gravity, a high refractive index,
From the viewpoint of low dispersion, the specific gravity is preferably 1.15 or less, the refractive index is 1.54 or more and the Abbe number is 35 or more.

In the above-mentioned method for producing a transparent resin, a general chain transfer agent, mercaptans, dialkyl disulfides, chloroform, carbon tetrachloride, etc. can be used as a molecular weight regulator used at the time of polymerization. Considering the transparency, color, heat resistance, etc.,
The dimer of α-methylstyrene is preferred. The molecular weight modifier is used in an amount of 0.1 to 5% by weight based on the total monomers.
If it is less than 0.1% by weight, the haze value tends to be high, and coloring tends to occur, and if it exceeds 5% by weight, various physical properties such as heat resistance are deteriorated.

In the above-mentioned method for producing a transparent resin, as the polymerization initiator used in the polymerization, those used in ordinary radical polymerization can be used as they are. For example, 1,1-bis (t-butylperoxy) 3,3,5
-Trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, n-butyl-4,4 '
-Bis (t-butylperoxy) valerate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, m-toluoyl peroxide,
Diisopropyl peroxy dicarbonate, di-2-ethylhexyl peroxy dicarbonate, dinormal propyl peroxy dicarbonate, dimethoxy isopropyl peroxy dicarbonate, cumyl peroxy neodecanoate, t-butyl peroxy-2-ethyl hexano , T-butylperoxy-3,5,5-trimethylhexanoate, di-t-butyldiperoxyisophthalate, organic peroxides such as t-butylperoxyisopropyl carbonate, 2,2′-azobis ( Isobutyronitrile), 2,2'-azobis (4-methoxy-
2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), dimethyl-
2,2'-azobisisobutyrate, 2,2'-azobis (2-methylbutyronitrile), 1,1'-azobis (1-cyclohexanecarbonitrile), 2-phenylazo-2,4-dimethyl- Examples thereof include azo polymerization initiators such as 4-methoxyvaleronitrile and 2,2′-azobis (2-methylpropane). Two or more of these polymerization initiators may be used in combination.

The above-mentioned polymerization initiator is preferably used in the range of 0.001 to 10 parts by weight with respect to 100 parts by weight of all the monomers. Considering the condition of the surface of the obtained polymer, the polymerization time and the like. 0.01-5 with respect to 100 parts by weight of all monomers
It is particularly preferred to use parts by weight.

In the above-mentioned method for producing a transparent resin, the above-mentioned molecular weight modifier and polymerization initiator are dissolved in a monomer, and since the resin obtained is a cross-linked polymer, it is usually cured and molded by a cast polymerization method. It is preferable. The curing temperature varies depending on the polymerization initiator used, but is preferably 30 to 120 ° C. However, to obtain a cast plate with less distortion,
It is preferable to cure slowly at a relatively low temperature.

In the above-described method for producing a transparent resin, from the viewpoints of preventing coloration, shortening the polymerization induction period, etc., nitrogen bubbling reduces the oxygen in the mixed solution to 1.0 mg / l or less, and then a glass mold for casting polymerization. It is preferable to pour the mixed solution into and to cure and mold it by a cast polymerization method. Further, from the viewpoint of preventing coloration, it is preferable to perform the heat treatment in an inert gas atmosphere when the cured product is removed from the mold and heat-treated at 120 ° C. for 1 to 2 hours after the completion of the main polymerization step. A lens shape can be formed by this cast polymerization method.

In the use of the above-mentioned transparent resin, phosphite-based, phenol-based, thioether-based antioxidants, aliphatic alcohols, fatty acid esters, etc., from the viewpoints of prevention of deterioration, thermal stability, processability, etc. Phthalates, triglycerides, fluorochemical surfactants,
Release agents such as higher fatty acid metal salts, other lubricants, plasticizers,
You may add and use an antistatic agent, a ultraviolet absorber, a flame retardant, a heavy metal deactivator, etc. These are preferably added during polymerization.

An organic silane-based hard coat film and a cured film of an organic silane resin can be directly laminated on the surface of the plastic lens substrate made of the above-mentioned transparent resin to obtain the plastic lens of the present invention.

The above-mentioned organic silane resin is, for example, a compound of formula 3 [general formula (II)]

Embedded image R ⁴ R ⁵ _a Si (OR ⁶ ) _3-a (II) (wherein R ⁴ is an organic group containing an epoxy group having 2 to 8 carbon atoms, and R ⁵ is 1 to 1 carbon atoms). 6 alkyl group, alkenyl group, halogenated alkyl group or allyl group, R ⁶ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyalkyl group or an acyl group, and a is an integer of 0 to 2) Is an organosilane compound or a partial hydrolyzate thereof. Specifically, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltris (methoxyethoxy) silane, γ-glycidoxypropylmethyldimethoxysilane, γ- There are organic silane compounds such as glycidoxypropylmethyldiethoxysilane and partial hydrolysates thereof. Examples of commercially available products include KP64C (trade name of Shin-Etsu Chemical Co., Ltd.).

10 to 80 parts by weight of a colloidal solution prepared by dispersing the above organic silane resin and inorganic fine particles such as antimony oxide sol, silica sol, titania sol and alumina sol in water or alcohol such as methanol, ethanol, isobutanol and diacetone alcohol. % Added directly onto the surface of the plastic lens substrate to give 50-14
A hard coat layer can be formed by heating and curing at 0 ° C. At this time, if necessary, a primer layer may be provided between the surface of the plastic lens substrate and the hard coat layer, but the primer is not necessary for the plastic lens substrate.

The inorganic fine particles preferably have a particle size of 1 to 100 μm, and a commercially available colloidal solution dispersed in water or an organic solvent can also be used.

The organic silane resin may include, if necessary, aluminum chelate, perchlorate such as perchloric acid, ammonium perchlorate and aluminum perchlorate, and alkali metal such as sodium acetate and potassium propionate. Curing catalysts such as salts and quaternary ammonium salts such as tetramethylammonium hydroxide can also be used.

[0045]

EXAMPLES The present invention will be described below in greater detail by giving Examples, but the scope of the present invention is not limited thereto.

Examples 1 to 29 0.5 parts by weight of lauroyl peroxide was added as a radical polymerization initiator to a mixed solution having the composition shown in Table 1 or Table 5, and 1,1-bis (t-butylperoxy) was further added. Three
After 0.2 part by weight of 3,5-trimethylcyclohexane was added and sufficiently stirred, the mixture was poured into a mold composed of two glasses and a gasket and heated from 30 ° C to 90 ° C over 20 hours. Remove the cured lens from the mold, 120 ° C
After heat-treating for 1 hour at room temperature, cool to room temperature, dip-coat organic silane resin (KP64C, Shin-Etsu Chemical Co., Ltd.), and apply at room temperature for 30 minutes, 90 ° C for 30 minutes, 120 ° C for 1 minute.
Heat cured for hours.

Comparative Examples 1 to 19 0.5 parts by weight of lauroyl peroxide was added as a radical polymerization initiator to a mixed solution having the composition shown in Table 2 or Table 6, and 1,1-bis (t-butylperoxy) was further added. Three
After 0.2 part by weight of 3,5-trimethylcyclohexane was added and sufficiently stirred, the mixture was poured into a mold composed of two glasses and a gasket and heated from 30 ° C to 90 ° C over 20 hours. Remove the cured lens from the mold, 120 ° C
After heat-treating for 1 hour at room temperature, cool to room temperature, dip-coat organic silane resin (KP64C, Shin-Etsu Chemical Co., Ltd.), and apply at room temperature for 30 minutes, 90 ° C for 30 minutes, 120 ° C for 1 minute.
Heat cured for hours.

Refractive index, Abbe number, specific gravity, heat resistance, transparency, impact resistance, chemical resistance, machinability, hard coat adhesion of the lenses obtained in Examples 1 to 29 and Comparative Examples 1 to 19 The contact angles, etc. were investigated and shown in Table 3, Table 4, Table 7 and Table 8.

The characteristic evaluation was based on the following methods. Refractive index, Abbe number: Measured at 20 ° C. using an Abbe refractometer (manufactured by Atago). Table 1 shows the D line (58
9.3 nm). -Specific gravity: Measured by the water substitution method. -Heat resistance: TMA (Thermal Mechanical Anallyzer, manufactured by Seiko Denshi) was used to measure the softening temperature. Haze rate (transparency): according to ASTM D 1003
The haze ratio of a lens having a center thickness of 5 mm was measured. The smaller the haze value, the better the transparency. -Impact resistance: A lens having a center thickness of 2 mm was evaluated according to the FDA standard. (Evaluation) ◯: No cracking, ×: Cracking-Chemical resistance: Dipped in acetone or toluene at room temperature for 24 hours, and those having no cloudiness on the surface in any solvent were passed. (Evaluation) ○: No change in appearance, △: Slightly cloudy, ×:
Cloudy or meltable / Machining workability: Lens for eyeglass lens
Edger (renz edger)] to determine whether to cut the edge. (Evaluation) ○: It was possible to cut cleanly, ×: The edge was melted.・ Hard coat adhesion: 1m with a knife on the hard coat film
After inserting 11 crosswise grids, 11 each in length and width, and adhering cellophane tape (made by Nichiban), the cellophane tape was rapidly peeled off and the number of squares which were not peeled off was examined. Evaluation: ◯ is 100/100 to 80/100. X is 0/100 to 20/100. Contact angle: A contact angle meter (manufactured by Kyowa Interface Science Co., Ltd.) was used to measure the contact angle of the lens substrate surface with water.

In the following, ST is styrene, TCDM
A is tricyclo [5.2.1.0 ^2,6 ] deca-8-yl, MMA is methyl methacrylate, MA is methacrylic acid, EGDM is ethylene glycol dimethacrylate, NPDA is neopentyl glycol diacrylate, and 9EGDM. Is nonaethylene glycol dimethacrylate, 14 EGDM is tetradecaethylene glycol dimethacrylate, 9EGMM is nonaethylene glycol monomethacrylate, α-MSD is a dimer of α-methylstyrene, and NOM is n-octyl mercaptan. The amount of α-MSD used is shown in% by weight based on all monomers. CHMA means cyclohexyl methacrylate.

[0051]

[Table 1] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 1 Mixed liquid composition ━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Monomer composition (weight part) α-MSD ST TCDMA MMA MA EGDM NPDA 9EGDM 14EGDM 9EGMM (wt%) ──────────────────────────────────── Example 1 80-- ---20--1.0 〃 2-80----20--1.0 〃 3 50 30 10---10--1.0 〃 4 50 30--10-10--1.0 〃 5 40 30 10-10 -10--1.0 〃 6 50 30--10-10--NOM1.0 〃 7 40 30--10-20--1.0 〃 8 50 30--10--10-1.0 〃 9 50 30--10 ---10 1.0 〃 10 45 30-5 10-10--1.0 〃 11 50 30---10 10--1.0 〃 12 40 30---20 10--1.0 〃 13 40 30---20- 10-1.0 〃 14 40 30---20--10 1.0 〃 15 40 25-5-20 10--1.0 ━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0052]

[Table 2] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 2 Mixed liquid composition ━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Monomer composition (weight part) α-MSD ST TCDMA MMA MA EGDM NPDA 9EGDM 14EGDM 9EGMM (wt%) ──────────────────────────────────── Comparative Example 1 100-- ------1.0 〃 2-100-------1.0 〃 3 60 30 10------1.0 〃 4 60 30--10----1.0 〃 5 20 30 10-40 ----1.0 〃 6 50-40-10----1.0 〃 7 50 30 10-10----1.0 〃 8 40 30 10--20---1.0 〃 9 50 30-10 10-- --1.0 〃 10 49.5 30 10-10-0.5--1.0 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━

[0053]

[Table 3] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 3 Evaluation results ━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Refractive index Abbe number Specific gravity Heat resistance Cloudiness ratio Impact resistance Chemical removal Cutting Heart coat contact Angle (-) (-) (g / cm ³ ) (℃) (%) Hammerability Product quality Workability Adhesion (°) ───────────────────── ──────────────── Example 1 1.57 33 1.08 95 0.6 ○ ○ ○ ○ 74 〃 2 1.53 57 1.11 148 0.5 ○ ○ ○ ○ 72 〃 3 1.55 41 1.07 108 0.5 ○ ○ ○ ○ 73 〃 4 1.55 41 1.09 113 0.5 ○ ○ ○ ○ 73 〃 5 1.54 42 1.09 116 0.5 ○ ○ ○ ○ 74 〃 6 1.55 41 1.09 113 0.5 * ○ ○ ○ ○ 73 〃 7 1.54 42 1.10 110 0.5 ○ ○ ○ ○ 70 〃 8 1.55 41 1.09 111 0.5 ○ ○ ○ ○ 76 〃 9 1.55 41 1.09 110 0.5 ○ ○ ○ ○ 77 〃 10 1.55 41 1.11 124 0.5 ○ ○ ○ ○ 71 〃 11 1.55 41 1.07 108 0.5 ○ ○ ○ ○ 73 〃 12 1.55 41 1.07 113 0.5 ○ ○ ○ ○ 75 〃 13 1.55 41 1.07 110 0.5 ○ ○ ○ ○ 76 〃 14 1.55 41 1.07 109 0.5 ○ ○ ○ ○ 77 〃 15 1.55 41 1.10 121 0.5 ○ ○ ○ ○ 71 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━━━━ * The lens is slightly yellow.

[0054]

[Table 4] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 4 Evaluation results ━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Refractive index Abbe number Specific gravity Heat resistance Cloudiness ratio Impact resistance Chemical removal Cutting Heart coat contact Angle (-) (-) (g / cm ³ ) (℃) (%) Hammerability Product quality Workability Adhesion (°) ───────────────────── ──────────────── Comparative Example 1 1.59 31 1.06 93 0.5 ○ × × × 81 〃 2 1.53 58 1.09 168 0.5 × × × × 86 〃 3 1.56 37 1.08 106 1.0 ○ × × × 78 〃 4 1.56 37 1.07 115 0.5 ○ ○ ○ × 79 〃 5 1.56 37 1.16 132 0.8 ○ ○ ○ × 78 〃 6 1.55 41 1.12 110 0.5 ○ ○ ○ × 78 〃 7 1.55 41 1.08 115 0.5 ○ ○ ○ × 79 〃 8 1.55 41 1.07 112 0.5 ○ ○ ○ × 80 〃 9 1.55 41 1.12 130 0.5 ○ ○ ○ × 78 〃 10 1.55 41 1.08 115 0.5 ○ ○ ○ × 79 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0055]

[Table 5] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 5 Mixed liquid composition ━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Monomer composition (weight part) α-MSD ST CHMA MMA MA EGDM NPDA 9EGDM 14EGDM 9EGMM (wt%) ──────────────────────────────────── Example 16-80- ---20--1.0 〃 17 50 30 10---10--1.0 〃 18 50 30--10-10--1.0 〃 19 40 30 10-10-10--1.0 〃 20 50 30--10 -10--NOM1.0 〃 21 40 30--10-20--1.0 〃 22 50 30--10--10-1.0 〃 23 50 30--10---10 1.0 〃 24 45 30-5 10 -10--1.0 〃 25 50 30---10 10--1.0 〃 26 40 30---20 10--1.0 〃 27 40 30---20-10-1.0 〃 28 40 30---20- -10 1.0 〃 29 40 25-5-20 10--1.0 ━━━━━━━━━━━━━━━━━━━━━━ ━━━━━━━━━━━━━

[0056]

[Table 6] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 6 Mixed liquid composition ━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Monomer composition (weight part) α-MSD ST CHMA MMA MA EGDM NPDA 9EGDM 14EGDM 9EGMM (wt%) ──────────────────────────────────── Comparative Example 11-100- ------1.0 12 60 30 10------1.0 〃 13 60 30--10----1.0 〃 14 20 30 10-40----1.0 〃 15 50-40-10- ---1.0 〃 16 50 30 10-10----1.0 〃 17 40 30 10--20---1.0 〃 18 50 30-10 10----1.0 〃 19 49.5 30 10-10-0.5- -1.0 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[0057]

[Table 7] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 7 Evaluation results ━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Refractive index Abbe number Specific gravity Heat resistance Cloudiness ratio Impact resistance Chemical resistance Cutting Heart coat Coat contact angle (−) (−) (G / cm ³ ) (℃) (%) Hammerability Product quality Workability Adhesion (°) ────────────────────── ─────────────── Example 16 1.53 57 1.11 95 0.5 ○ ○ ○ ○ 71 〃 17 1.55 41 1.07 96 0.5 ○ ○ ○ ○ 73 〃 18 1.55 41 1.09 111 0.5 ○ ○ ○ ○ 72 〃 19 1.54 42 1.09 115 0.5 ○ ○ ○ ○ 74 〃 20 1.55 41 1.09 111 0.5 * ○ ○ ○ ○ 74 〃 21 1.54 42 1.10 109 0.5 ○ ○ ○ ○ 70 〃 22 1.55 41 1.09 110 0.5 ○ ○ ○ ○ 74 〃 23 1.55 41 1.09 108 0.5 ○ ○ ○ ○ 77 〃 24 1.55 41 1.11 124 0.5 ○ ○ ○ ○ 70 〃 25 1.55 41 1.07 107 0. 5 ○ ○ ○ ○ 73 〃 26 1.55 41 1.07 111 0.5 ○ ○ ○ ○ 73 〃 27 1.55 41 1.07 109 0.5 ○ ○ ○ ○ 76 〃 28 1.55 41 1.07 108 0.5 ○ ○ ○ ○ 76 〃 29 1.55 41 1.10 121 0.5 ○ ○ ○ ○ 71 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ * The lens was colored slightly yellow.

[0058]

[Table 8] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Table 8 Evaluation results ━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Refractive index Abbe number Specific gravity Heat resistance Cloudiness ratio Impact resistance Chemical removal Cutting Heart coat contact Square (−) (−) (g / cm ³ ) (℃) (%) Hammerability Product quality Workability Adhesion (°) ───────────────────── ──────────────── Comparative example 11 1.53 58 1.09 95 0.5 × × × × 85 〃 12 1.56 37 1.08 97 1.0 ○ × × × 78 〃 13 1.56 37 1.07 113 0.5 ○ ○ ○ × 78 〃 14 1.56 37 1.16 132 0.8 ○ ○ ○ × 78 〃 15 1.55 41 1.13 108 0.5 ○ ○ ○ × 78 〃 16 1.55 41 1.08 113 0.5 ○ ○ ○ × 78 〃 17 1.55 41 1.07 112 0.5 ○ ○ ○ × 80 〃 18 1.55 41 1.12 130 0.5 ○ ○ ○ × 80 〃 19 1.55 41 1.08 113 0.5 ○ ○ ○ × 79 ━━━━━━━━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━━━

[0059]

The plastic lens according to the first aspect has excellent transparency and excellent adhesion between the plastic lens substrate and the cured film of the organic silane resin (organic silane-based hard coat film). The plastic lens according to a second aspect has the same effect as that of the plastic lens according to the first aspect, and further has a low specific gravity, high refractive index and low dispersion (high Abbe number), and excellent heat resistance. The plastic lens according to the third aspect has the same effect as the plastic lens according to the first aspect, and is particularly excellent in impact resistance and the like. The plastic lenses according to claims 4 to 5 have the effects of the plastic lenses according to claims 1 to 3, and are particularly excellent in transparency. The plastic lens according to claim 6 has the effect of the plastic lens according to claim 2, and is particularly excellent in heat resistance. The plastic lens according to claim 7 has the effect of the plastic lens according to claim 3, and is particularly excellent in impact resistance and the like. The plastic lens according to the eighth aspect has the effect of the plastic lens according to the first aspect, and is particularly excellent in the adhesiveness between the transparent resin and the hard coat layer.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Fumiaki Kanaga 14 Goi Minamikaigan, Ichihara City, Chiba Hitachi Chemical Co., Ltd. Goi Factory

Claims (8)

[Claims] 1. A compound represented by the general formula (I): R ₁ -O- (R ₂ O) n -R ₃ ... (I) (wherein R ₁ is a vinyl group, an allyl group or a methallyl group. , An acryloyl group or a methacryloyl group, R ₂ is a divalent hydrocarbon group having 1 to 40 carbon atoms, and R ₃ is hydrogen, a vinyl group, an allyl group, a methallyl group, an acryloyl group, a methacryloyl group, or other than these. 1 to 40 carbon atoms
Which is a valent hydrocarbon group, and n is an integer of 2 to 50) A plastic made of a transparent resin obtained by polymerizing a monomer containing an alkylene oxide group-containing monomer represented by the formula A plastic lens in which a hard coat layer made of an organic silane resin is directly provided on the surface of a lens substrate. 2. A monomer containing an alkylene oxide group represented by general formula (I) as an essential component is a monomer containing an alkylene oxide group represented by general formula (I). 1 to 30 parts by weight of styrene, 15 to 60 parts by weight of styrene, 10 to 70 parts by weight of methacrylic acid ester or acrylic acid ester having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion, and other copolymerizable The plastic lens according to claim 1, which is a monomer mixture obtained by blending 0 to 40 parts by weight of a vinyl monomer such that the total amount thereof is 100 parts by weight. 3. A monomer containing an alkylene oxide group-containing monomer represented by general formula (I) as an essential component contains 1 to 50% by weight of a polyfunctional monomer. The plastic lens according to claim 1, which is a mixture of monomers. 4. The plastic lens according to claim 1, wherein a molecular weight modifier is present during the polymerization. 5. The plastic lens according to claim 4, wherein the molecular weight modifier is a dimer of α-methylstyrene. 6. A methacrylic acid ester or acrylic acid ester having an alicyclic hydrocarbon group having 5 to 22 carbon atoms in the ester portion is cyclohexyl methacrylate, norbornyl methacrylate, norbornyl methyl methacrylate, tricyclomethacrylate [ 5.2.1.0 ^2,6 ] deca-8-yl and tricyclomethacrylate [5,2,1,
The plastic lens according to claim 2, which is at least one compound selected from the group consisting of 0 ^2,6 ] deca-4-methyl. 7. The polyfunctional monomer is a polyfunctional monomer among monomers having an alkylene oxide group, divinylbenzene, diallyl phthalate, allyl acrylate, allyl methacrylate, methallyl acrylate, methallyl. Methacrylate and alkylene groups have 2 to 1 carbon atoms
The plastic lens according to claim 3, which is one or more kinds of monomers selected from the group consisting of alkylene glycol diacrylate having 2 and alkylene glycol dimethacrylate having 2 to 12 carbon atoms in the alkylene group. 8. The monomer containing an alkylene oxide group represented by formula (I) according to claim 1, wherein R _{2 in} formula (I) is a divalent group having 1 to 5 carbon atoms. The plastic lens according to claim 1, which is a monomer having a hydrocarbon group.