JP2003131005A - Plastic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a thermoplastic eyeglass lens which has sufficient optical characteristics as an eyeglass lens for sight correction, and which has so excellent shock resistance as to meet the recent requirement for the safety of eyeglass lens. SOLUTION: A curing layer made of silicone resin is provided on the surface of a plastic lens base material comprised of aromatic-alphatic copolymerization polycarbonate resin. On the top of that, a monolayer or multilayer antireflection coating made of inorganics is provided.

Description

DETAILED DESCRIPTION OF THE INVENTION [0001] The present invention relates to a plastic lens
More specifically, the method of producing
Characteristics such as resistance, chemical resistance, and adhesion between the lens substrate and the cured layer.
Plastic lens with excellent impact resistance
Related. [0002] 2. Description of the Related Art Plastic lenses are lightweight,
It has excellent properties such as shock resistance and impact resistance.
Rapidly spread in optical materials, especially in the field of spectacle lenses
I am doing it. Has been a drawback of plastic materials
Problems such as low surface hardness and surface reflection
A hard coat film of inorganic material or use an inorganic substance on the lens surface.
Surface modification technology such as providing an anti-reflection film deposited on the surface
Significant improvement due to development
Increasingly, the market for plastic lenses is expanding
You. However, silicone hard coat and inorganic anti-reflection
When providing a stop film, the impact resistance of the plastic lens
There is a problem of drastic reduction. Allyl diglycol
Thermosetting plastic lens represented by carbonate
In the case of
By providing a primer layer between
Methods for obtaining improved impact resistance are disclosed. For example,
Provide a layer made of urethane resin as a primer layer
Method (Japanese Unexamined Patent Publication No. Hei 8-54501)
Clears US FDA standards even after anti-sun coat
It is disclosed that a spectacle lens having impact resistance can be obtained.
ing. However, after the primer layer is
Performing a coat increases costs. Meanwhile, thermoplastic
Mold transparent plastic material can be injection molded
To improve productivity, precision moldability,
It has excellent characteristics such as no problem of coloring over time.
Above all, polycarbonate has very good impact resistance
Sports that take advantage of the characteristics of
Demand for eyeglass lenses for children and children is growing. So
The excellent impact resistance of the surface of the above thermosetting materials
Almost no reduction is seen by the reforming. But
Further, polycarbonate has a low number (νD = 3).
0), having sufficient characteristics as a corrective spectacle lens
It is hard to say. Polycarbonate is silicone
Adhesion to the system hard coat is low,
Requires primer treatment to improve adhesion
To be widely used due to problems such as
Not. Akri, another representative of transparent thermoplastics
Resin is a lens material for eyeglasses in terms of heat resistance, impact resistance, etc.
It is hard to say that it has sufficient properties as a material. [0003] SUMMARY OF THE INVENTION The present invention
It is intended to solve problems associated with various conventional technologies.
In particular, it has sufficient optical characteristics as a corrective spectacle lens.
And meet recent safety requirements for spectacle lenses
Provide thermoplastic spectacle lenses with excellent impact resistance
It is in. [0004] Means for Solving the Problems The present inventors have proposed these methods.
As a result of intensive research to solve the issues,
And a polymer having the structural formula (1) and the structural formula (2).
Table of plastic lens substrates made of carbonate resin
A cured layer made of silicone resin is provided on the surface,
Provide a single-layer or multilayer anti-reflection film made of inorganic material in the part
Optical properties sufficient as corrective spectacle lenses
A thermoplastic eyeglass lens with excellent impact resistance is obtained.
And arrived at the present invention. [0005] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS A plastic according to the present invention will now be described.
The method for producing cleanse will be specifically described. The plastic lens substrate used in the present invention
Having the above structural formulas (1) and (2)
An aromatic monoaliphatic copolymer polycarbonate is used. The weight
Coalescing is random, block or alternating copolymer, or
Aromatic monoaliphatic having structural formulas (1) and (2)
Copolycarbonate and Polycarbonate Having Structural Formula (1)
-Including carbonate blends, etc.
The aliphatic dihydroxy represented by the above structural formula (2)
The mole fraction of the structural unit derived from the compound is 10 to 10.
90% is desirable, and if less than 10%,
The effect of improving optical characteristics such as the number of
If it is higher than 90%, heat resistance and impact resistance are poor.
Become. In addition, aliphatic-aromatic copolymer polycarbonate resin
Fat has a weight average molecular weight of 50,000 to 200,000
Preferably, it is more preferably 70,000 to
150,000. 50,000 weight average molecular weight
Lower values result in lower impact resistance, higher than 200,000
Melt viscosity becomes too high, making injection molding very difficult.
Is not preferred. [0007] Aromatic monoaliphatic copolymer polycarbonate resin
Fat is used as a general polycarbonate resin production method.
It can be manufactured by known methods, especially
I can do more. Ester exchange using carbonic diester
In the exchange reaction, polymerization is performed by a known melt polycondensation method.
Can be. That is, the aromatic di represented by the following formula (4)
Hydroxy compound, aliphatic dihydrogen represented by the following formula (5)
Addition using a hydroxy compound, a carbonic acid diester and a catalyst
Molten weight while removing by-products under normal pressure or reduced pressure under heat
The condensation is performed. Reactions generally involve more than one step.
It is performed in a step process. [0008] Embedded image (In the above formula, X is Embedded image Where R₃And R₄Is a hydrogen atom or carbon
An alkyl group or a phenyl group represented by the following formulas
And R4 may combine to form a ring. R_lAnd R₂
Represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a halogen atom
And R_lAnd R₂May be the same or different.
Further, m and n represent the number of substituents and are integers of 0 to 4.
You. ) [0009] Embedded image Specifically, the first-stage reaction is carried out at 120 to 2
60 ° C., preferably at a temperature of 180 to 240 ° C., 0 to 5 hours
The reaction is preferably performed for 0.5 to 3 hours. Then the reaction
Raise the reactivity while increasing the degree of decompression of the system.
Polycondensation at a temperature of 200 to 300 ° C under reduced pressure of mmHg or less
Perform the reaction. It is also used in conducting the above reaction.
The reaction device may be a tank type or an extruder type.
No. As the polymerization catalyst, a basic compound is used.
It is. As such a basic compound, in particular, alkali
Metal compounds, alkaline earth metal compounds, nitrogen-containing compounds
These compounds may be used alone or in combination.
Can be used. As such an alkali metal compound,
Organic acid salts, inorganic acid salts, oxides, and hydroxides of alkali metals
Products, hydrides, alcoholates, etc. are used.
Is sodium hydroxide, potassium hydroxide, cesium hydroxide
, Lithium hydroxide, sodium bicarbonate, hydrogen bicarbonate
Lium, lithium hydrogen carbonate, sodium carbonate, potassium carbonate
, Cesium carbonate, lithium carbonate, sodium acetate,
Potassium acetate, cesium acetate, lithium acetate, steari
Sodium phosphate, potassium stearate, stearic acid
Cesium, lithium stearate, sodium borohydride
, Lithium borohydride, sodium phenyl borohydride
Um, sodium benzoate, potassium benzoate, benzoate
Cesium acid, lithium benzoate, sodium hydrogen phosphate
System, 2 potassium hydrogen phosphate, 2 lithium lithium phosphate,
Disodium phenylphosphate, dipotassium phenylphosphate
System, dilithium phenylphosphate, bisphenol A 2
Sodium salt, 2 potassium salt, 2 cesium salt, 2 lithium
Salt, phenol sodium salt, potassium salt, cesium
And lithium salts and the like. Further, as the alkaline earth metal compound,
Organic acid salts, inorganic acid salts, oxides, and hydroxides of alkali class 10 metals
Chloride, hydride, alcoholate, etc.
Are calcium hydroxide, barium hydroxide, magnesium hydroxide
Cium, strontium hydroxide, calcium bicarbonate,
Barium bicarbonate, magnesium bicarbonate, hydrogen bicarbonate
Trontium, calcium carbonate, barium carbonate, ma carbonate
Gnesium, strontium carbonate, calcium acetate, vinegar
Barium acid, magnesium acetate, strontium acetate,
Calcium stearate, barium stearate,
Magnesium arate, strontium stearate,
Are used. As the nitrogen-containing compound, quaternary ammonium
Uses hydroxides, quaternary ammonium salts, amines, etc.
Specifically, tetramethyl ammonium hydroxide
Sid, tetraethylammonium hydroxide, tetra
Pyrammonium hydroxide, tetrabutylan
Monium hydroxide, trimethylbenzylammonium
Alkyl, aryl, alary
Ammonium hydroxides having
Tylamine, triethylamine, dimethylbenzylamido
And tertiary amines such as triphenylamine, dimethylamine
Secondary amines such as min, diethylamine, etc.
Primary amines such as butane and ethylamine, 2-methylimida
Imidazoles such as sol, 2-phenylimidazole, etc.
Or ammonia, tetramethylammonium
Rohydride, tetrabutylammonium borohydride
Ride, tetrabutylammonium tetraphenylbore
, Tetramethylammonium tetraphenyl volley
And basic salts such as These catalysts are represented by the above formula (3).
Aromatic dihydroxy compound and fat represented by formula (4)
10 moles per 1 mole of the total with the aliphatic dihydroxy compound^-9
-10^-3Molar amounts, preferably 10^-7-10^-FiveMole of
Use the amount. The aromatic dihydro used in the above formula (3)
As the xy compound, specifically, bis (4-hydroxy
Phenyl) methane, 1,1-bis (4-hydroxyphene)
Nyl) ethane, 2,2-bis (4-hydroxyphenyl)
L) propane, 2,2-bis (4-hydroxyphenyl)
Le) butane, 2,2-bis (4-hydroxyphenyl)
Octane, bis (4-hydroxyphenyl) phenylmeth
Tan, 2,2-bis (4-hydroxy-3-methylphen)
Nyl) propane, 1,1-bis (4-hydroxy-3-
t-butylphenyl) propane, 2,2-bis (4-h
Droxy-3-bromophenyl) propane, 1,1-bi
S (4-hydroxyphenyl) cyclopentane, 1,1
-Bis (4-hydroxyphenyl) cyclohexane,
4,4'-dihydroxydiphenyl ether, 4,45
-Dihydroxy-3,3'-dimethylphenylate
4,4'-dihydroxyphenyl sulfide, 4,
45-dihydroxy-3,35-dimethyldiphenyls
Sulfide, 4,45-dihydroxydiphenyl sulfoxy
Sid, 4,4'-dihydroxy-3,3'-dimethyldi
Phenylsulfoxide, 4,4'-dihydroxydife
Nyl sulfone, 4,4'-dihydroxy-3,3'-di
Methyl diphenyl sulfone and the like. Inside of these
And especially 2,2-bis (4-hydroxyphenyl) pro
Bread, ie bisphenol A or 1,1-bis
(4-hydroxyphenyl) cyclohexane is preferred
No. The aliphatic dihydrogen represented by the above formula (4)
As the droxy compound, specifically, tricyclodecane
Dimethanol or pentacyclopentadecanedimeta
Knoll is used. Further, as the carbonic acid diester, dife
Nil carbonate, ditolyl carbonate, bis (evening
Lolophenyl) carbonate, m-cresyl carbonate
G, dinaphthyl carbonate, bis (diphenyl) car
Bonate, diethyl carbonate, dimethyl carbonate
G, dibutyl carbonate, dicyclohexyl carbonate
Or the like is used. Of these, especially diphenyl
Carbonates are preferred. Diphenyl carbonate is
The above aromatic dihydroxy compound (3) and aliphatic dihydro
1.01 to 1.0 mol per 1 mol of the total of the xy compound (4)
It is preferably used in an amount of 1.30 mol. The polycarbonate resin of the present invention has
Catalyst to maintain qualitative and hydrolytic stability.
Removal or inactivation is preferred. Generally, public
Alkali metal or alkali by addition of known acidic substances
It is preferable to deactivate a transesterification catalyst such as an earth metal.
Appropriately implemented. As these substances, specifically,
aromatic sulfonic acids such as p-toluenesulfonic acid;
Aromatic sulfonates such as butyl toluenesulfonate
Ters, stearic acid chloride, butyric acid chloride, salt
Such as benzoyl chloride, toluenesulfonic acid chloride
Organic halides, alkyl sulfates such as dimethyl sulfate
Organic halides such as salts and benzyl chloride are preferably used.
Used. After deactivation of the catalyst, low boiling compounds in the polymer are removed.
At a pressure of 0.1 to 1 mmHg and a temperature of 200 to 300 ° C
A step for devolatilization and removal may be provided.
Horizontal kneader with wings, lattice wings, glasses wings, etc.
A membrane evaporator is preferably used. In the present invention, the above-mentioned heat stabilizer,
In addition to hydrolysis stabilizers, antioxidants, pigments, dyes,
Agents, fillers, UV absorbers, lubricants, release agents, crystal nuclei
Additives, plasticizers, flow improvers, antistatic agents, etc.
Can be. Also, with the aim of further improving the properties of the resin
Shake other polycarbonate resin or thermoplastic resin
Can also be used. These additives are prepared by a conventionally known method.
Each component can be mixed with polycarbonate resin
You. For example, mix each component with a turn bull mixer or Henschel
Representative of mixers, ribbon blenders and super mixers
After mixing with a high-speed mixer,
The method of melting and kneading with a lee mixer, roll, etc. is appropriately selected.
Is done. The silicone resin has the general formula Rl_aR2_bSi
(OR3)_4-abAnd / or its hydrolyzate
Drying and / or drying the organosilicon coating composition
A cured resin layer obtained by heating and curing (here,
R1 and R2 each represent an alkyl group, an alkenyl group,
Group, or halogen, epoxy group, glycidoxy
Group, amino group, mercapto group, methacryloxy group
Or a hydrocarbon group having a cyano group, and R3 has 1 to 1 carbon atoms.
10 alkyl groups, alkoxyalkyl groups, acyl groups,
Phenyl group, and a and b are 0 or 1).
These organosilicon compounds include methyl silicate
, Ethyl silicate, n-propyl silicate, is
o-Provyl silicate, n-butyl silicate, se
c-butyl silicate, tert-butyl silicate, etc.
Tetraalkoxysilanes and their hydrolysates,
, Methyltrimethoxysilane, methyltriethoxy
Run, methyltrimethoxyethoxysilane, methyltri
Acetoxysilane, methyltributoxysilane, ethyl
Trimethoxysilane, ethyltriethoxysilane, vinyl
Rutrimethoxysilane, vinyltriethoxysilane, vinyl
Nyltriacetoxysilane, vinyltrimethoxyethoxy
Sisilane, phenyltrimethoxysilane, phenyltri
Ethoxysilane, phenyltriacetoxysilane, γ-
Black mouth propyltrimethoxysilane, γ-black mouth propyl
Lutriethoxysilane, γ-chloropropyltriacet
Xysilane, 3,3,3-trifluoropropyl trime
Toxisilane, γ-methacryloxypropyl trimeth
Xysilane, γ-aminopropyltrimethoxysilane,
γ-aminopropyltriethoxysilane, γ-mercap
Topovir trimethoxysilane, γ-mercaptop
Lutriethoxysilane, N-β (aminoethyl) -γ-
Aminopropyltrimethoxysilane, β-cyanoethyl
Triethoxysilane, methyltriphenoxysilane,
Loromethyltrimethoxysilane, chloromethyltriet
Xysilane, glycidoxymethyltrimethoxysilane,
Glycidoxymethyltriethoxysilane, α-glycid
Xylethyltrimethoxysilane, α-glycidoxyethyl
Rutriethoxysilane, β-glycidoxyethyltrime
Toxisilane, β-glycidoxyethyltriethoxy
Orchid, α-glycidoxypropyl trimethoxysilane,
α-Glycidoxypip piltriethoxysilane, β-g
Lycidoxypipe pyrtrimethoxysilane, β-glycid
Xip mouth piltriethoxysilane, γ-glycidoxyp
Mouth pyrtrimethoxysilane, γ-glycidoxyprovir
Triethoxysilane, γ-glycidoxypip piltrip
Poxysilane, γ-glycidoxypip
Sisilane, γ-glycidoxypropyltrimethoxyeth
Xysilane, γ-glycidoxypropyl triphenoxy
Silane, α-glycidoxybutyltrimethoxysilane,
α-glycidoxybutyltriethoxysilane, β-gly
Sidoxybutyltrimethoxysilane, β-glycidoxy
Butyltriethoxysilane, γ-glycidoxybutyl
Limethoxysilane, γ-glycidoxybutyl triethoxy
Sisilane, δ-glycidoxybutyltrimethoxysila
Δ-glycidoxybutyltriethoxysilane,
(3,4-epoxycyclohexyl) methyltrimethoxy
Sisilane, (3,4-epoxycyclohexyl) methyl
Triethoxysilane, β- (3,4-epoxy
Xyl) ethyltrimethoxysilane, β- (3,4-
Epoxy hexyl) ethyltriethoxysilane,
β- (3,4-epoxycyclohexyl) ethyltri
Propoxysilane, β- (3,4-epoxy mouth opening)
Sil) ethyltributoxysilane, β- (3,4-e
Hexyl) ethyltrimethoxyethoxy
Orchid, β- (3,4-epoxycyclohexyl) ethyl
Rutriphenoxysilane, γ- (3,4-epoxycycline)
Hexyl) provyltrimethoxysilane, γ- (3,3)
4-epoxycyclohexyl) provyltriethoxy
Run, δ- (3,4-epoxycyclohexyl) petit
Trialkoxysilanes such as
Acylsilanes, triphenoxysilanes or their hydrolysates
Decomposition products and dimethyldimethoxysilane, phenylmethyl
Rudimethoxysilane, dimethyldiethoxysilane,
Nylmethyldiethoxysilane, γ-chloropropylmethyl
Rudimethoxysilane, dimethyldiacetoxysilane, γ
-Methacryloxypropyl methyldimethoxysilane,
γ-mercaptop porphylmethyldimethoxysilane, γ-
Aminopropylmethyldimethoxysilane, araminop
Propyl methyldiethoxysilane, methylvinyl dimethoxy
Sisilane, glycidoxymethylmethyldimethoxysila
Α-glycidoxyethylmethyldimethoxysilane,
β-glycidoxyethylmethyldimethoxysilane, α-
Glycidoxypipe pyrmethyldimethoxysilane, β-g
Lycidoxy lip mouth pyrmethyldimethoxysilane, γ-gly
Sidoxip mouth pillmethyldimethoxysilane, γ-glyci
Doxypip pillmethyldiethoxysilane, γ-glycid
Xip mouth pillmethyldiphenoxysilane, γ-glycid
Xiprovir ethyl dimethoxysilane, γ-glycidol
Sip mouth pill vinyl dimethoxysilane, γ-glycidoxy
Dialkoxysilanes such as provyldimethoxysilane or
Is diacyloxysilanes or their hydrolysates, etc.
Used. These organosilicon compounds can be used alone
Or a mixture of two or more. In particular, dyeing
Organosilicon compounds containing epoxy groups for the purpose of imparting color
Is preferred. These organosilicon compounds have a curing temperature
And use it to promote curing.
Is preferred. Hydrolysis is pure water or hydrochloric acid, vinegar
Add acidic aqueous solution of acid, sulfuric acid, etc. to the organosilicon compound,
It is performed by stirring. The degree of hydrolysis is pure
By adjusting the amount of water or acidic aqueous solution
It can be easily controlled. Upon hydrolysis,
Pure water equal to or more than 3 moles equivalent to the alkoxy group or
Addition of an acidic aqueous solution is preferred in terms of accelerating curing. The hydrolysis may be carried out without solvent,
A solvent may be used for the purpose of performing water splitting more uniformly.
When using a solvent, mix the organosilicon compound with the solvent
It is preferable to carry out hydrolysis after the reaction. Also, depending on the purpose,
Heat and / or reduce alcohol and the like after hydrolysis
An appropriate amount may be removed under pressure before use.
It is also possible to add a medium and use it. With these solvents
Alcohols, ethers, ketones, esters,
And aromatic hydrocarbons. Also these solvents are needed
Depending on the case, it may be used as a mixed solvent of two or more kinds. [0027] If necessary, the hydrolysis reaction is promoted.
Hydrolysis at room temperature or higher to advance the reaction such as precondensation
May be carried out under heating.
May be performed under cooling at room temperature or lower. In the present invention, the plastic lens base
Improved flow when applying the coating composition to materials
And improve the smoothness of the coating to improve the friction of the coating surface.
To reduce the number of surfactants on the coating composition.
It is preferable to use a surfactant added. Specifically,
Blocks of methyl siloxane and alkylene oxide
Or graft copolymer, or fluorine-based surfactant, etc.
Is valid. In addition, dyes and pigments and fillers can be dispersed
Dissolve the polymer to color the coating,
To improve the adhesion between the cured film and the substrate and the physical properties of the cured film
Is also possible. In addition, ultraviolet rays for improving the weather resistance of the cured film
Addition of wire absorber and addition of antioxidant to improve heat deterioration
It is preferably implemented. Further, the cured layer made of silicone resin
Surface hardness is further improved, and antistatic properties are improved.
Coating to improve the refractive index of the activated layer and weather resistance
Various inorganic substances are suitably added to the composition.
In particular, to improve the surface hardness, high molecular weight silicic anhydride
Colloidal form in organic solvents such as water and / or alcohol
Colloidal silica, which is a dispersion, is preferably used. Ko
Loidal silica is silica fine particles having a particle size of 1 to 10 μm.
More preferably, silica fine particles having a particle size of 5 to 40 μm are dispersed.
What has been used is preferably used. Also, colloidal force
Is in the range of 5 to 70% for improving the adhesion to the antireflection film.
Is preferably used. In the present invention, a hard resin comprising a silicone resin
Formation of the activated layer, i.e., of the organosilicon coating composition
When curing, the plastic lens substrate
After applying the coating composition, dry and / or
By applying heat, ultraviolet irradiation or electron beam irradiation
The aim is to achieve curing acceleration and low-temperature curing.
Various curing agents can be used in combination. As a curing agent,
Various epoxy resin curing agents or various organic silicon resin hardeners
An agent is preferably used. Specifically, various organic acids and
And their acid anhydrides, nitrogen-containing organic compounds, and various metals
Complex compounds, metal alkoxides, organic metals of alkali metals
Examples include borate and carbonate of alkali metal. this
These curing agents may be used alone, and if necessary, two types may be used.
A mixture of the above may be used. [0032] In the present invention, a silicone resin
The coating layer is formed by coating the plastic lens substrate.
After applying the coating composition, mainly by performing a heat treatment
Will be implemented. Spray method, dipping
Method, spinner method, etc.
No. The heating temperature is preferably 50 to 1200 ° C, more preferably 80 to
110 ° C. Heat is applied until the cured film has sufficient hardness.
The heating temperature is higher and the heating time is shorter.
  It is good to carry out over 3 to 5 hours. The plastic substrate and the silicone resin
To improve the adhesion to the hardened layer made of grease
Pretreatment of the substrate before applying the coating composition
New Specifically, corona discharge, DC under reduced pressure, low frequency
Wave, high frequency or microwave high voltage discharge etc.
Pre-processing is exemplified. Especially for high frequency discharge under reduced pressure
The resulting low-temperature plasma treatment provides reproducibility and production
It is preferably used from the viewpoint of properties. In the present invention, the cured silicone resin layer
After that, a single-layer or multilayer anti-reflection film is further formed.
Let it run. As a substance that forms an anti-reflection film,
Hard materials are used for metal, metal or semi
Metal oxides, fluorides, silicides, borides, carbonized
, Nitride, sulfide, etc. are selected. As metal oxide
Is silicon oxide, zirconium oxide, titanium oxide, oxide
Aluminum, antimony trioxide, antimony pentoxide,
Tantalum oxide, yttrium oxide, ytterbium oxide
Etc. are exemplified. Magnesium fluoride
Boron nitride, silicon nitride, etc.
It is. A single-layer or multi-layer formed from the above materials
Methods for forming an anti-reflection film include vacuum evaporation and spa
Tuttering method, ion plating method, ion beam
An assist method is exemplified. In addition, silicone resin curing
To further improve the adhesion between the film and the anti-reflection film
Is corona discharge, DC under reduced pressure, low frequency, high frequency
Or various surface treatments such as high voltage discharge by microwave
It is valid. Especially obtained by high frequency discharge under reduced pressure
Low-temperature plasma processing from the viewpoint of reproducibility and productivity
It is preferably used. These activated gases or ions
Vacuum deposition, ion plating
Is performed in the same chamber as
Effective above. [0036] According to the present invention, it is sufficient as a spectacle lens.
Surface properties, hardened layer and reflection
Produces a lens with excellent adhesion, appearance and impact resistance
Can be very useful. Hereinafter, the present invention will be described specifically with reference to examples.
However, the present invention is limited by the following examples.
Not something. Reference Example (1) Production of lens substrate 2,2-bis (4-hydroxyphenyl) cyclohexa
6060.7 g (22.585 mol) of tricyclode
4433.2 g of candimethanol (22.585
L), 100733.3 g of diphenyl carbonate (4
7.02 mol), 0.00162 g of sodium hydrogen carbonate
(1.025 × 10^-FourMol), a stirrer and a distilling device
Equipped with a 50-liter stirrer and a distilling device
And heated to 180 ° C under nitrogen atmosphere and kept for 2 hours
After that, the degree of reduced pressure was adjusted to 150 Torr. This state
And after 1 hour, reduce the degree of pressure to 0.2 Torr over 2 hours
And 240 ′ over one hour while maintaining this degree of reduced pressure.
C to a total of 4
The reaction was carried out with stirring for hours. After the reaction is completed, nitrogen is introduced into the reactor.
Into the reactor at normal pressure, and apply polycarbonate from the bottom of the reactor.
Was extracted by a gear pump. This resin is twin-screw extruded
Into the machine (barrel temperature 240'C) and used as catalyst deactivator
0.12 g of n-butyl p-toluenesulfonate
ADK STAB AO-50 (Kenka Co., Ltd.)
Adekastab 2112 (made by Asahi Denka Co., Ltd.)
3.70 g1 each, and SH556 as a release agent
(Toray Dow Corning Co., Ltd.) and knead 55.8 g.
After forming a uniform polymer and forming a strand through a die
The pellet was cut by a pelletizer. This port
The carbonate is bisphenol Z: tricyclodeca
Dimethanol molar ratio = 50 = 50, weight average molecular weight M
w = 56000. Cylinder temperature 2 of this resin
Injection molding is performed at 50 ° C and a mold temperature of 150 ° C.
After cooling slowly, a 75 mm diameter, 1.2 mm
Injection molded pieces were obtained. Physical properties of this molded piece
When measured, the refractive index was 1.585, Abpe number was 38,
The transition point was 124 ° C. (2) Silicone coating composition
Preparation and application, curing gamma-glycidoxy lip mouth pyrmethyldiethoxysilane 15
0 parts was cooled to 1000 and stirred with 0.05
18 parts of normal hydrochloric acid was added dropwise over 30 minutes. Followed by
And methanol-dispersed colloidal silica (average particle size 12
(± 1 μm, solid content 30%) Drops while stirring 350 parts
After the addition, the mixture was further stirred at 10'C overnight. This
60 parts of methylcellosolve, isopropyl alcohol
200 parts, n-butanol 100 parts, silicone field
Surfactant (L-7002 manufactured by Nippon Unicar Co., Ltd.) 2 parts
After mixing and stirring thoroughly, the silicone coating
The composition. Molding of the substrate obtained in the above (1)
The coating composition was dipped in a piece by a dipping method (with a lifting speed of 1
(00 m / min). 10 coated molded pieces
Heat and cure at 0 ° C for 4 hours.
A cured layer was formed. (3) Formation of antireflection film The plastic having the cured layer obtained by the above (2)
Zr02 / Si ○ which is an inorganic substance on the cured layer of cleanse
2, ZrO_Two, SiO_TwoThree types in this order
Set the optical film thickness to λ / 4 (λ is the visible wavelength)
Multi-layer coating was performed by an empty deposition method. This allows the cured layer and
And a plastic lens having an antireflection film. This
The total light transmittance of the plastic lens was 97%. Example 1 The cured layer obtained in the above Reference Example and
Performance evaluation of plastic lenses with anti-reflection coating
The method was performed as described in (1). The results are shown in Table 1. (A) Steel wool hardness Rub the painted surface with # 0000 steel wool and scratch
Is determined. The criterion is A: There is no damage even with strong friction. B: Slightly scratched when strongly rubbed. C: Scratches even with weak friction. D = easily scratched with nails. (B) Adhesion Cross cut table according to JIS D-0 202
The test was performed by the test method. That is, 1 mm
Using a steel knife, cut the squares reaching the corner substrate from above the coating surface.
After putting 00 pieces and pressing the cellophane adhesive tape strongly
To 90 degree direction and check for peeling of coating film
Was. (C) Appearance About the obtained plastic lens,
The transparency and the degree of coloring were observed. (D) Impact resistance A steel ball drop test was performed based on the FDA standard. That is, 1
6g steel ball in plastic lens from 127cm height
Drop naturally toward the heart,
The steel balls are allowed to fall naturally in sequence,
It was tested whether it was broken by a steel ball. Embodiment 2 In Example 1, the hard coat composition was changed to Toshiba Silicon
Co., Ltd. thermosetting silicone hard coat liquid PH0
Isoprovir alga 587 so that the active ingredient becomes 17%
Diluted by Kohl and filtered through 1μm filter
Perform the same operation except for changing the
A plastic lens with an anti-irradiation film was obtained. Evaluation results
It is shown in Table 1. Comparative Example 1 An anti-reflection film was prepared in the same manner as in Example 1.
The same operation was performed except that it was not attached.
A tic lens was obtained and evaluated. Table 1 shows the evaluation results.
You. Comparative Example 2 In Example 1, except that neither a cured layer nor an antireflection film was provided.
Obtained a plastic lens that performed exactly the same operation
Value. Table 1 shows the evaluation results. [0049] [Table 1] According to the present invention, it is sufficient as a spectacle lens.
Surface properties, hardened layer and anti-reflection
Manufacturing lenses with excellent film adhesion, appearance, and impact resistance
And can be very useful.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) G02C 7/02 G02B 1/10 A // C08L 69:00 Z F term (Reference) 2K009 AA06 AA15 CC03 CC09 CC34 CC42 CC47 DD02 DD03 DD06 4F006 AA36 AB39 AB73 AB74 BA02 BA03 BA14 CA05 DA04 EA03 EA05

Claims (1)

Claims 1. As a structural unit, a cured layer made of a silicone resin is provided on the surface of a plastic lens base made of a polycarbonate resin having the following structural formulas (1) and (2). And a plastic lens provided with an antireflection film made of an inorganic material on the cured layer. Embedded image (In the above structural formula (1), X is Wherein R ₃ and R ₄ are a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a phenyl group, and R ₃ and R ₄ may combine to form a ring. R ₁ and R ₂ are a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or halogen, and R ₁ and R ₂ may be the same or different. Also,
m and n represent the number of substituents and are integers from 0 to 4. )