JP2956887B2 - Manufacturing method of plastic lens - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [0001] BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to the production of plastic lenses.
For the construction method, more specifically, excellent impact resistance and abrasion resistance
Resistance, hot water resistance, chemical resistance, close contact between lens substrate and cured layer
It has properties such as performance and satisfies the US FDA standard
The present invention relates to a method for manufacturing a tic lens. [0002] 2. Description of the Related Art Plastic lenses are lightweight, shock-resistant,
It has advantages such as easy processability and dyeing properties.
In recent years, it has rapidly spread in the field of eyeglass lenses. Further
Said that it was easily damaged due to insufficient surface hardness.
Tables that may improve defects or cause flickering of images or objects
Adding high added value to lenses by suppressing surface reflection
Many surface modifications have already been proposed for the purpose of
More and more plastic lens markets are expanding
is there. For example, regarding the former improvement of surface hardness,
In addition, by providing a cured coating,
For improvement, an inorganic substance is deposited on the lens surface and an anti-reflection film is installed.
Plastics with high hardness or anti-reflection ability
Stick lenses are also available. However, silicon-based
When providing a cured film or inorganic anti-reflection film, use plastic
There is a drawback that reduces the impact resistance of the lens,
A plastic lens with these two films applied simultaneously
When the impact resistance declines more and more,
Have been. [0003] In addition, silicon is used as a plastic lens substrate.
Silicone cured film and plastic when applying a cured film
Improving adhesion to lens substrates has been a major challenge
Therefore, the plastic lens substrate
Apply etching treatment such as
Primer layer between cleanse substrate and silicon-based cured film
The surface of the plastic lens substrate
The surface has been modified, and the latter
Conventional techniques for surface modification include, for example,
A method using an epoxy compound as a product (Japanese Unexamined Patent Publication No.
214301), acrylic and / or methacrylic
Plastics containing a rill-based compound and an aromatic vinyl compound as main components
Method using an immersion composition (JP-A-60-214302)
Publication), acrylic polyols and polyfunctional organic isocyanes
Method using a primer composition comprising
No. 61-114203). [0004] SUMMARY OF THE INVENTION As described above, silicon
Surface hardness improvement and inorganic reflection by coating of system hardened film
Problems associated with improving surface reflection by coating the anti-reflective coating
One of the issues is the impact resistance of plastic lenses
This problem is a problem as in the prior art described above.
After providing the immer layer, apply a silicon-based cured film,
Even plastic lenses with inorganic anti-reflection coating
Not resolved. This point will be described in more detail.
No. 214302 discloses acrylic and
And / or methacrylic compound and aromatic vinyl compound
In a method using a primer composition as a main component,
Emulsion is used for forming the mer layer.
Since water is used in the margillon formulation, dry the primer.
Problems such as residual water during drying and a long drying time
is there. In addition, silicone-based curing for plastic lens substrates
When the film and inorganic anti-reflection film are applied, the adhesion is good.
However, when the center thickness of the lens is less than 2.0 mm,
Therefore, it is difficult to satisfy the US FDA standard. [0005] Japanese Patent Laid-Open Publication No. Sho 60-214301 discloses
In the method shown, the primer layer forming material is
Epoxy compound is used.
Heating in the presence of a xy curing catalyst will only
Because it will be a layer, it will take a long time to cure.
It costs. Also, after providing this primer layer,
Plus with system-based cured film and inorganic anti-reflection film
Tic lens is chemically resistant, silicone-based cured film and lens base
Although it has excellent properties such as improved adhesion to materials, it has impact resistance
Sex has not been improved. Further, Japanese Patent Application Laid-Open No. 61-114203 discloses
In the disclosed method, after applying a primer layer,
Recon-cured coating, inorganic anti-reflective coating
Plastic lens is abrasion resistant, chemical resistant, hot water resistant,
Although improvement in scratch resistance etc. is observed, impact resistance is not
Is not improved. As described in detail above, the conventional primer coat
Adhesion, chemical resistance, abrasion resistance
Although the effect is recognized in the impact resistance, the impact resistance is still
And the silicon-based cured film or silicon
Plastic with a cured film and an inorganic anti-reflective coating
Conforms to U.S. FDA standards when a primer layer is provided.
To pass the spectacle lens impact resistance test.
In the case of an inass lens, set the center thickness of the lens to 2.0 mm or more.
This increases the edge thickness of the lens.
May cause the lens to become heavy, resulting in poor appearance.
This is not preferable in practical use. Accordingly, an object of the present invention is to provide a plastic lens.
After a primer layer is provided on the
Layer, conventional plastic with inorganic anti-reflective coating
Eliminates the disadvantages of lenses, abrasion resistance, hot water resistance, chemical resistance
Properties such as adhesion and adhesion between the lens substrate and the cured layer
At the same time, plastics with excellent impact resistance
An object of the present invention is to provide a method for manufacturing a lens. [0009] Means for Solving the Problems The present inventors have set forth the above-mentioned eye.
As a result of repeated studies to achieve the target,
Coals, polyalkylene glycols, poly (alk
Lenadipate), poly-ε-caprolactone, poly
Butadiene glycols, poly (alkylene carbonate
G) or active hydrogen selected from silicone polyols
Obtained from a polyisocyanate-containing compound and a polyisocyanate
Primer made of urethane resin with a thickness of 0.01 to 30 μm
Layer on the surface of the plastic lens substrate,
Providing a hardened layer made of a fixed silicone resin,
On the surface, if necessary, a single layer or multiple layers by evaporation of an inorganic substance
Plastic obtained by forming a layer of anti-reflective coating
Lens, wear resistance, hot water resistance, chemical resistance, lens
Not only has excellent adhesion between the substrate and the cured layer,
It has been found that it has excellent impact properties. Accordingly, the present invention provides an alkylene glycol
, Polyalkylene glycols, poly (alkylene
Dipate), poly-ε-caprolactone, polybutadi
Englycols, poly (alkylene carbonates)
Or containing active hydrogen selected from silicone polyols
Obtained from the compound and polyisocyanate
A primer layer made of resin and having a thickness of 0.01 to 30 μm
Provided on the surface of the plastic lens substrate, followed by the general formula Embedded image (Where R¹, R²Represents an alkyl group, an alkenyl group,
Allyl group, or halogen group, epoxy group, amino group,
Mercapto, methacryloxy or cyano groups
A hydrocarbon group having³Is an alkyl having 1 to 8 carbon atoms
Kill group, alkoxyalkyl group, acyl group, phenyl group
N and m are 0 or 1)
Silicon compound and / or hydrolyzate thereofAnd grains
Consisting of colloidal silica having a diameter of 1 to 100 mμCoty
To cure the coating composition to form a silicon-based cured layer.
In addition, on the surface, a single layer by evaporation of an inorganic substance or
Plastic characterized by forming a multilayer antireflection film
In the manufacturing method of the lens. Hereinafter, the present invention will be described in more detail. In the present invention, a plastic lens substrate is used.
Any known plastic lens substrate is used.
Is the expression Embedded image Diallyl glycol bisallyl car
Those obtained by polymerizing the carbonate are preferred.
Commonly used. Necessary for the polymerization of the monomer of formula (I)
Known additives such as light stabilizers and antioxidants, and copolymerization
Other possible monomers may be added. Monomer of formula (I)
The polymerization method is disclosed in detail in JP-A-57-44686.
It is shown. [0013] In the present invention, the surface of the plastic lens substrate
A polyurethane resin layer is provided thereon as a primer layer. In the present invention, it is used as a primer composition.
Some polyurethane resins have active hydrogen at both ends.
Resin formed from the reaction of
You. Here, the active hydrogen-containing compound is ethylene glycol.
Coal, 1,2-propylene glycol, 1,3-buta
Diol, 1,4-butanediol, 1,6-hexa
Diol, neopentyl glycol, dipropylene
Alkylene glycols such as recall and diethylene glycol
Coals; polypropylene glycol, polyethylene glycol
Polyols such as recall and polytetramethylene glycol
Alkylene glycols; poly (diethylene adipate)
G), poly (tetramethylene adipate), poly (hex)
Samethylene adipate), poly (neopenthylene adipate)
Poly (alkylene adipates) such as
ε-caprolactone; poly (1,4-butanediene)
Recall, poly (1,2-butanediene) glycol
Any polybutadiene glycols; poly (hexamethylene)
Poly (alkylene carbonate) such as
G): two or more hydroxyl groups such as silicone polyols
And other known polyol compounds.
It is also possible to use active hydrogen-containing compounds of the formula (1). Polyisocy
Examples of anates include tolylene diisocyanate,
Silylene diisocyanate, 4,4'-diphenyl meta
Diisocyanate, 1,5-naphthalenediisocyane
3,3'-dimethyl-4,4'-diphenyldiyl
Aromatic diisoisocyanates such as socyanates;
1,6-hexamethylene diisocyanate, isophorone
Diisocyanate, 4,4'-dicyclohexylmethane
Diisocyanate, 1,3-bis (isocyanatomethy
Le) cyclohexane, trimethylhexamethylenediiso
Aliphatic diisocyanates such as cyanates
However, for example, Japanese Patent Application Laid-Open No. 61-114203 discloses
Hydrogenated xylylene diisocyanate, poly
Biuret conjugate of isocyanate or isocyanu
Rate conjugate, polyisocyanate and trimethylolp
Known polyisocyanes such as reaction adducts with lopan
The use of a seat is also possible. The polyurethane resin can be produced by a known method.
And amines and dibutyltin dilau
A metal compound such as a rate is used. The thickness of the primer layer is 0.01 to 30 μm
Significantly improved impact resistance, particularly preferably 1 to 21 μm
If it is less than 0.01 μm, the effect of improving impact resistance is not obtained.
Not too large, applied to lens over 30μm
Surface accuracy at the time decreases. As a solvent used in the primer composition
Are hydrocarbons, halogenated hydrocarbons, alcohols,
Ketones, esters, ethers, etc.
It is also possible to use known solvents. Particularly preferred
Means toluene, ethyl acetate, methyl ethyl ketone,
Lahydrofuran, which may be used alone
Alternatively, it may be used as a mixed solvent of two or more kinds. In addition,
Various leveling agents or weather resistance to improve fabricability
UV absorbers and antioxidants to improve
Dyes, pigments, and other known additives that enhance the performance and function of the film
Agents can be used in combination. How to apply primer composition
Methods include spinner method, dipping method and other known methods.
What is necessary is just to select from among them. Made of polyurethane resin
To form a primer layer, the primer composition
After applying to plastic lens substrate surface, 30 ℃ ~
200 ° C., preferably in the range of 60 ° C. to 150 ° C.
What is necessary is just to heat at temperature. Depending on the solvent used, 1
A desired primer layer is formed by heating for ６０60 minutes. In the present invention, the above-mentioned cured primer layer
Above, the general formula Embedded image (Where R¹, R^TwoRepresents an alkyl group, an alkenyl group,
Allyl group, or halogen group, epoxy group, amino group,
Mercapto, methacryloxy or cyano groups
A hydrocarbon group having^ThreeIs an alkyl having 1 to 8 carbon atoms
Kill group, alkoxyalkyl group, acyl group, phenyl group
And n and m are 0 or 1)
An organosilicon compound and / or a hydrolyzate thereof, and
Coated with colloidal silica (particle size 1-100 mμ)
After coating the coating composition with a silicone resin
A further cured layer is provided. Specific representative examples of these organosilicon compounds
As methyltrimethoxysilane, ethyltriet
Xysilane, methyltriethoxysilane, dimethyldimethyl
Toxysilane, phenyltrimethoxysilane, dimethyl
Dimethoxysilane, phenylmethyldimethoxysilane,
Vinyl triethoxysilane, vinyl tris (β-methoxy
Siethoxy) silane, vinyltriacetoxysilane, γ
-Glycidoxypropylmethyldiethoxysilane, γ-
Glycidoxypropyltrimethoxysilane, γ-merca
Ptopropyltrimethoxysilane, glycidoxymethyl
Trimethoxysilane, glycidoxymethyltriethoxy
Silane, glycidoxymethyltripropoxysilane,
Lisidoxymethyltributoxysilane or its water content
Disassembly, but other known compounds can be used.
Noh. These organosilicon compounds may be used alone or in combination.
These can be used in combination. The colloidal silica has a particle size of 1 to 100 mμ.
Silica fine particles, more preferably, a particle size of 5 to 40 mμ.
Silica fine particles of methanol, ethanol, n-pig
Dispersed in solvents such as alcohol and water
(See JP-A-60-214302). This
Curing of the iodine-based composition is achieved by heating only the composition and / or
Is reached by drying, UV irradiation or electron beam irradiation
Although it is possible to promote curing, low-temperature curing, etc.
A variety of curing agents may be used in combination. Specific representative examples of curing agents
As various organic acids and their acid anhydrides, nitrogen
Containing organic compounds, various metal complex compounds or metal alcohols
Various salts such as oxides and carbonates are exemplified. Especially preferred
Or metal complex salts, which may be used alone,
It is also possible to use two or more kinds in combination. The method of coating this is a primer
Spraying method, date method as well as coating method of composition
It is appropriately selected from known methods such as a ping method and a spinner method.
Just do it. This curing reaction proceeds by heating to form a cured film.
Formed, but hardened in hot air at 80 ° C to 150 ° C for 30 minutes to 240 minutes
It is good to make it. In the present invention, the organosilicon-based composition is
After coating and curing, further single- or multi-layer anti-reflective coating
Is provided. Materials used for forming the anti-reflection film include inorganic materials.
A substance that is a metal, metal or metalloid oxide,
, Silicide, boride, carbide, nitride, sulfide, etc.
Is raised. Specifically, SiO_Two, SiO, ZrO
_Two, Al_TwoO_Three, TiO_Two, Sb_TwoO_Three, Sb_TwoO_Five,
Metal oxides such as tantalum oxide, MgF_TwoSuch as
Things. A single-layer or multi-layer composed of the above substances
Methods for forming an anti-reflection film include a vacuum deposition method and a stainless steel.
Pattering method, ion plating method, ion bee
Mu assist method and the like. The plastic having an antireflection film obtained above
The lens has a hard surface that is durable in addition to anti-reflective properties.
The impact resistance has been improved by the primer layer.
Suitable for eyeglass lenses and other optical articles
Can be. [0025] EXAMPLES In order to clarify the present invention, the following examples are given.
It should be noted that the present invention is limited to these Examples.
There is no. The number of parts and% in the examples are by weight. [Example 1] (1) Production of plastic lens substrate Diethylene glycol bisallyl carbonate 150
Part, Parloyl IPP (manufactured by NOF Corporation)
5 parts of peroxydicarbonate)
The insolubles of this mixture were removed with a filter, and the filtrate was etched.
Molded gas of ren / ethyl acrylate copolymer resin
Injected into a mold made of a kettle and two glass molds
did. Next, linearly from 40 ° C to 65 ° C for 4 hours at 40 ° C
10 hours, linearly from 65 ° C to 85 ° C for 5 hours,
After heating at 85 ° C for 2 hours, gasket and glass
Field has been separated. Further, the obtained lens was heated at 130 ° C. for 2 hours.
Performs time annealing to remove distortion inside the lens
Was. The lens thus obtained is an optical lens without internal distortion
It was a good plastic lens for use. Less than
Below, use this as a plastic lens substrate
Was. (2) Preparation and application of primer composition
Hardening Commercially available polyurethane LQ3510 [manufactured by Sanyo Chemical Co., Ltd.
Solid concentration 30% (using polyalkylene adipate)]
To toluene / IPA (isopropyl alcohol) (mixed
Ratio 2/1) Dilute to 10% solids concentration with mixed solvent. Next
Then, slowly add 50 parts of this solution with stirring to the silicon-based interface.
Activator (L-7002 manufactured by Nippon Unicar Co., Ltd.) 0.03
To give a primer composition. This primer composition was used in (1) the obtained primer
Immersion method on a plastic lens substrate (pulling speed 10cm
/ Min). The applied base lens is 120 ° C
And heat-cured for 30 minutes to form a 8.0 μm thick film on the substrate.
A primer layer was formed. (3) Preparation of silicon-based coating composition
Production and application curing γ-glycidoxypropylmethyldiethoxysilane 15
0 parts was cooled to 10 ° C, and stirred while stirring.
18 parts of constant hydrochloric acid was added dropwise over 30 minutes. Followed by meta
Knoll-dispersed colloidal silica (average particle size 12 ± 1 m
(μ, solid content 30%)
After completion of the dropwise addition, the mixture was further stirred at 10 ° C. overnight. this
52 parts of methyl cellosolve, isopropyl alcohol
208 parts, n-butanol 104 parts, silicon-based surfactant
2 parts of a surfactant (L-7002 manufactured by Nippon Unicar Co., Ltd.)
After mixing and stirring well, set for silicon coating
It was an adult. The primer having a primer layer obtained in (2) above
The above coating is applied on the primer layer of the plastic lens substrate.
Coating composition as in the case of the primer composition.
Clothed. After application, heat and cure at 120 ° C for 3 hours to
After forming a cured layer made of resin, the primer layer
And a plastic lens having a cured layer was obtained. (4) Formation of antireflection film The primer layer and the cured layer obtained by the above (3)
Inorganic substance on the cured layer of plastic lens having
ZrO_Two/ SiO_TwoMixture (optical thickness nd = λ / 2)
 ), ZrO_Two(Nd = λ / 2), SiO_Two(Nd = λ /
4) is sequentially coated in multiple layers by vacuum evaporation
Plastic having a layer, a cured layer and an anti-reflection coating
Got. (5) Test and evaluation results The primer layer obtained in (3) and (4) above,
Plastic lens with primer layer and primer layer, cured
Performance evaluation of plastic lens with anti-reflection coating
This was performed in the following manner. (A) Appearance Good transparency and surface accuracy of the lens by visual observation
If there is no defect, pass (o).
Passed (x). (B) Steel wool hardness Rub the painted surface with # 0000 steel wool and scratch
Was evaluated. 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. (C) Adhesion: cured film and lens substrate or
The adhesion between the anti-irradiation film and the cured film conforms to JIS D-0202.
The test was performed according to the cross-cut tape test method. Immediately
Then, using a steel knife, place a 1 mm square on the coating surface of the base material.
00 are formed. Next, put cellophane adhesive tape on it
(Product name Cellotape, made by Nichiban Co., Ltd.)
After peeling, it is peeled off rapidly in the direction of 90 degrees,
I checked nothing. (D) Impact resistance: steel ball based on FDA standard
A drop test was performed. That is, about 16.4 g of steel balls are 127
Drop naturally from the height of cm to the center of the lens,
Those that did not break were considered acceptable. The lens used in this test
Were all 1.2 mm in center thickness. The primer layer and the cured layer obtained in this example
With plastic lens and primer layer, cured layer,
Table 1 shows the evaluation results of the plastic lens with an anti-reflection film.
Shown in The two types of plastic lenses with composite films are the same
Evaluation results, appearance, scratch resistance, impact resistance, adhesion
It was excellent. [Example 2] Preparation of a primer composition
On the basis of the solid content concentration of 5%, the solid content concentration of 5%
Polyurethane resin solution used as primer composition
Except for the above, a primer layer and curing were performed in the same manner as in Example 1.
Plastic lens with film and primer layer, cured
Example 1 A plastic lens with a layer and an antireflection film was obtained.
The same test was performed. The test results are shown in Table 1. Example 3 Preparation of a Primer Composition
In this case, a commercially available polyurethane was used in Example 1.
LQ3505 [Sanyo Chemical Co., Ltd.] in place of LQ3510
30% solid content (using polyalkylene adipate)
For toluene) / IPA (mixing ratio 2/1)
Polyurethane obtained by diluting with a solvent to a solid content of 5%
Except that a resin solution was used as the primer composition.
In the same manner as in Example 1
Stick lens and primer layer, hardened layer, anti-reflective
Obtained a plastic lens with a blocking film and tested it as in Example 1.
did. The test results are shown in Table 1. Example 4 Preparation of a Primer Composition
As a commercial polyurethane, E380 [Japan
Elastolan Co., Ltd. (Poly (alkylene carbonate)
G) Use)) and add tetrahydrofuran
The polyurethane resin solution obtained by adjusting the polymer concentration to 3%
Example 1 except that it was used as a primer composition
Similarly, plastic layer with primer layer and cured film
Plus primer layer, cured layer, anti-reflective coating plus
A tic lens was obtained and tested as in Example 1. Test result
The results are shown in Table 1. Example 5 Preparation of a Primer Composition
In connection with this, E580 [Japan
Elastollan Co., Ltd. (using poly ε-caprolactone)
Add tetrahydrofuran using
Polyurethane resin solution obtained by adjusting the degree to 3%
Except that it was used as a mer composition in the same manner as in Example 1.
Plastic lens with a primer layer and a hardened layer
And primer layer, cured layer, plastic with anti-reflective coating
A lens was obtained and tested as in Example 1. Table of test results
-1. Example 6 Preparation of a Primer Composition
As a commercially available polyurethane, SP-25 [3
Manufactured by Yo Chemical Co., Ltd., solid content concentration 30% (poly-ε-capro
Using lactone)] and adding methyl ethyl ketone
Polyurethane resin obtained by adjusting the primer concentration to 5%
Performed all except using the solution as a primer composition
In the same manner as in Example 1, a plastic having a primer layer and a hardened layer was used.
With cleanse and primer layer, hardened layer, anti-reflective coating
A plastic lens was obtained and tested as in Example 1.
The test results are shown in Table 1. Example 7 When the concentration of the primer composition was 7
%, And apply the primer composition
Not only once, but also after drying, apply the same
Repeat this series of operations to dry
Primers in exactly the same manner as in Example 4 except that
Layer, plastic lens with hardened layer and primer
Layer, cured layer, plastic lens with anti-reflective coating,
The test was performed in the same manner as in Example 1. The test results are shown in Table 1. Example 8 Preparation of a primer composition
In the case of the commercially available polyurethane used in Example 1,
Instead, use polyurethane obtained by the following method
So that this polyurethane has a solid concentration of 10%
Polyurethane solution obtained by diluting with tetrahydrolan
Example 1 except that was used as a primer composition
Plastic layer with primer layer and cured layer
Glass, primer layer, cured layer, anti-reflective coating
I got a stick lens. [0045]Polyurethane manufacturing method "Terratan 3000 (Polyol)
108 parts of Polyether Glycol manufactured by Co., Ltd.
38 parts of renglycol and isocyanate
Using xamethylene diisocyanate, these are NCO
/ OH ratio was adjusted to 1.0. Then the mixture
Was diluted with a toluene solvent to a solid content of 30%.
Then, the mixture was stirred at 90 ° C. overnight to complete the reaction.
This gave the desired polyurethane. ”
Plastic lenses and plastics with
Plastic lens with immersion layer, cured layer and anti-reflective coating
Was tested in the same manner as in Example 1, and the results shown in Table 1 were obtained. Example 9 Solid Concentration of Primer Composition
The degree of application is 1%.
The Gnar method was used. First, ply on the convex surface of the plastic lens.
0.5 μl of the mer composition was dropped, and the rotation speed was increased to 3000 rpm.
For 30 seconds. The coated lens substrate is at 50 ° C
It was dried by heating for 5 minutes. This primer dried
Apply the primer composition to the
Repeat the above series of operations, apply 5 coats
Subsequent drying was performed at 120 ° C. for 10 minutes. Otherwise
Plus with primer layer and cured layer exactly as in Example 1.
Tic lens and primer layer, cured layer, anti-reflective coating
A plastic lens was obtained and tested in the same manner as in Example 1.
Was. The test results are shown in Table 1. [Comparative Example 1] The commercially available polymer used in Example 1
Instead of urethane solution, use styrene / butyl acryle
Salt / hydroxyethyl methacrylate / acrylic acid
(100/100/2/5 mixing ratio) quaternary copolymer (acrylic
Polyol) and hexamethylene diisocyanate with N
Mix at a CO / OH ratio of 2/1 and add methyl isobutyl ketone
/ Solids obtained by dilution with ethyl acetate (50/50 mixing ratio)
A 0% solution was used as a primer composition and
Apply to the surface of a stick lens substrate, heat treat
Except that a urethane cured film was formed,
Similarly, a plastic layer with a primer layer and a cured layer
Plus primer layer, cured layer, anti-reflective coating plus
A tic lens was obtained and tested as in Example 1. Test result
The results are shown in Table 1. [Comparative Example 2] The plastic described in (2) of Example 1 was used.
Cured in the same manner as in Example 1 except that the immersion layer is not applied.
Example 1 A plastic lens with a layer and an antireflection film was obtained.
The same test was performed. The test results are shown in Table 1. Comparative Example 3 Preparation of Primer Composition
Or adjust the solids concentration to 0.1%
In applying the composition, use the spinner method instead of the dipping method
Was. First, 0.5 μl of the primer composition is dropped on the lens surface
Then, it was rotated at 3000 rpm for 30 seconds. Plastic
The base lens coated with the immersion composition was heated at 120 ° C. for 30 minutes.
Heat treatment for a primer layer with a thickness of 0.004 μm.
Formed. Otherwise, the procedure was the same as in Example 3.
Plastic lens and ply with immersion layer, cured layer
Plastic layer with a mer layer, cured layer and anti-reflective coating
And tested as in Example 1. The results are shown in Table 1. [Comparative Example 4] Primer in Example 1
When applying the composition, not only once, but also after drying
In addition, this series of coating and drying in the same way by dipping method
The operation was repeated, and the coating was repeated five times to obtain a film thickness of 4
Example 1 except that a primer layer of 1.0 μm was formed.
Plastic layer with primer layer and cured layer
With cleanse and primer layer, hardened layer, anti-reflective coating
A plastic lens was obtained and tested as in Example 1.
The results are shown in Table 1. [Embodiment 10] (1) Manufacturing plastic lenses Diethylene glycol bisallyl carbonate 150
Parts, methyl methacrylate 15 parts, Parloyl IPP
(Diisopropyl peroxycarbonate manufactured by NOF Corporation
5.5) Mix and stir 5.5 parts of the mixture.
Was removed with a filter, and the filtrate was treated with ethylene / ethyl acetate.
Gasket and two pieces of molded resin of rate copolymer resin
Injected into a mold made of smold. Then 30 ° C
6 hours linearly from 40 ° C to 50 ° C
4 hours linearly, 5 hours linearly from 50 ° C to 70 ° C,
2 hours linearly from 70 ° C to 85 ° C, 1 hour at 85 ° C
Gasket and glass mold are separated after heating
did. Further, the obtained lens is annealed at 120 ° C. for 2 hours.
To remove distortion inside the lens. Like this
The resulting lens is an optical plastic with no internal distortion
It was a good lens. The obtained plastic lens substrate was as follows:
The same treatment as in Example 7 was carried out, and the primer layer and the cured layer
Plastic lens and primer layer, hardened layer, anti-reflective
A plastic lens with a stop film was obtained, and a trial was performed in the same manner as in Example 1.
Tested. The test results are shown in Table 1. [Example 11] Production of plastic lens
Diethylene glycol bisallyl carbonate
150 parts, methyl methacrylate 40 parts, parloyl
IPP (Nippon Yushi Co., Ltd. diisopropyl peroxyka
6 parts) and then mixed and stirred.
The residue is removed with a filter and the filtrate is washed with ethylene / ethyl acetate.
A molded gasket of a related copolymer resin and two gas
Example except that it was injected into a mold made by lath mold
Plastic layer with primer layer and cured layer
With cleanse and primer layer, hardened layer, anti-reflective coating
A plastic lens was obtained and tested as in Example 1.
The results are shown in Table 1. Example 12 Production of Plastic Lens
Diethylene glycol bisallyl carbonate
150 parts, methyl methacrylate 15 parts, diethylene
Glycol diacrylate 3 parts, Parloyl IPP (JP
Diisopropyl peroxycarbonate manufactured by Hon Yushi Co., Ltd.
G) Mix and stir 6 parts, then remove the insolubles
And the filtrate is ethylene / ethyl acrylate
A molded gasket of copolymer resin and two glass
Same as Example 10 except that it was injected into a mold made of
Plastic layer with primer layer and cured layer
And plastic with primer layer, cured layer and anti-reflective coating
A lock lens was obtained and tested in the same manner as in Example 1. The result is a table
-1. [0055] [Table 1]As is clear from the above table, according to the present invention,
Appearance, abrasion resistance, scratch resistance, adhesion, as well as impact resistance
A plastic lens with extremely excellent properties was provided. [0057] According to the present invention, appearance, adhesion and abrasion resistance are obtained.
Not only excellent in resistance and scratch resistance, but also
Dramatically improved the impact resistance of plastic lenses
A good plastic lens can be obtained.

──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Mitsuo Sugimura 2-7-5 Nakaochiai, Shinjuku-ku, Tokyo Inside Hoya Corporation (56) References JP-A-63-141001 (JP, A) (58) ) Surveyed field (Int.Cl. ⁶ , DB name) G02B 1/00-1/12

Claims (1)

(57) [Claims] Polyurethane obtained from an active hydrogen-containing compound selected from alkylene glycols, polyalkylene glycols, poly (alkylene adipates), poly-ε-caprolactone, polybutadiene glycols, poly (alkylene carbonate) s and silicone polyols, and polyisocyanate Resin film thickness 0.01 to
A primer layer of 30 μm is provided on the surface of the plastic lens substrate, and then a general formula: (Where R ¹ and R ² each represent an alkyl group, an alkenyl group,
Allyl group, or halogen group, epoxy group, amino group,
R ³ is a hydrocarbon group having a mercapto group, a methacryloxy group or a cyano group; R ³ is an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group, an acyl group, or a phenyl group; n and m are 0 or 1 Organosilicon compound and / or hydrolyzate thereof , and particles
A silicon-based cured layer is provided by coating and curing a coating composition made of colloidal silica having a diameter of 1 to 100 μm, and a single-layer or multilayer antireflection film is formed on the surface thereof by vapor deposition of an inorganic substance. A plastic lens manufacturing method characterized by the above-mentioned.