JP3130555B2 - Plastic lens materials, plastic lenses and spectacle lenses - Google Patents
Plastic lens materials, plastic lenses and spectacle lensesInfo
- Publication number
- JP3130555B2 JP3130555B2 JP03097322A JP9732291A JP3130555B2 JP 3130555 B2 JP3130555 B2 JP 3130555B2 JP 03097322 A JP03097322 A JP 03097322A JP 9732291 A JP9732291 A JP 9732291A JP 3130555 B2 JP3130555 B2 JP 3130555B2
- Authority
- JP
- Japan
- Prior art keywords
- plastic lens
- plastic
- lenses
- refractive index
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
【0001】[0001]
【産業上の利用分野】本発明は、耐熱性、表面硬度、耐
薬品性及び透明性に優れ、かつ屈折率の高いプラスチッ
クレンズ、眼鏡用レンズ、これらに使用されるプラスチ
ックレンズ材料に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastic having a high refractive index and excellent heat resistance, surface hardness, chemical resistance and transparency .
The present invention relates to cleansing lenses, spectacle lenses, and plastic lens materials used for these lenses .
【0002】[0002]
【従来の技術】プラスチックレンズは成形が容易なこ
と、軽いことなどの特徴を生かし、光学製品に広く用い
られている。中でも眼鏡レンズとして用いられる透明プ
ラスチックは耐熱性、耐薬品性が要求されるため、ポリ
メチルメタクリレ−ト、ポリスチレン等の熱可塑性プラ
スチックではなくポリジエチレングリコールビスアリル
カーボネート(CR−39)等の熱硬化性プラスチック
が使用されていた。2. Description of the Related Art Plastic lenses are widely used in optical products because of their features such as easy molding and light weight. Among them, transparent plastics used as spectacle lenses are required to have heat resistance and chemical resistance. Therefore, instead of thermoplastics such as polymethyl methacrylate and polystyrene, thermosetting such as polydiethylene glycol bisallyl carbonate (CR-39) is used. Plastics were used.
【0003】しかし、近年、CR−39が低屈折率であ
ることから、高屈折率の新規な透明プラスチックを開発
する試みが多数なされている。However, in recent years, since CR-39 has a low refractive index, many attempts have been made to develop a new transparent plastic having a high refractive index.
【0004】高屈折率のプラスチックを得ようとする場
合、分子構造にフッ素を除くハロゲン原子の導入、芳香
族環の導入、イオウ原子の導入を行なうのが一般的であ
る。In order to obtain a plastic having a high refractive index, it is common to introduce a halogen atom other than fluorine, an aromatic ring, and a sulfur atom into the molecular structure.
【0005】[0005]
【発明が解決しようとする課題】しかし、これらの方法
では屈折率1.60程度の透明プラスチックは得られる
ものの、1.60以上、特に1.65以上のプラスチッ
クは得られなかった。However, with these methods, a transparent plastic having a refractive index of about 1.60 can be obtained, but a plastic having a refractive index of 1.60 or more, particularly 1.65 or more, cannot be obtained.
【0006】この発明は上述の背景になされたものであ
り、その目的とするところは、屈折率が1.60、特に
1.65以上の高屈折であり、耐熱性、表面硬度、耐薬
品性に優れたプラスチックレンズを得ることができる材
料を提供することである。The present invention has been made in view of the above background, and has as its object a high refractive index having a refractive index of 1.60, particularly 1.65 or more, heat resistance, surface hardness and chemical resistance. An object of the present invention is to provide a material capable of obtaining an excellent plastic lens.
【0007】[0007]
【課題を解決するための手段】本発明者らは上記の問題
点を解決するために鋭意検討した結果、特定の化合物を
主成分とするラジカル重合可能な組成物の共重合体をプ
ラスチックレンズに応用したところ、耐熱性、表面硬
度、耐薬品性及び透明性に優れ屈折率1.60以上、特
に1.65以上の高屈折なプラスチックレンズが得られ
ることを見出し本発明に至った。Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above problems, and as a result, have found that a copolymer of a radically polymerizable composition containing a specific compound as a main component is used as a plastic lens. When applied, they found that a high-refractive plastic lens excellent in heat resistance, surface hardness, chemical resistance and transparency and having a refractive index of 1.60 or more, particularly 1.65 or more was obtained.
【0008】すなわち、本発明のプラスチックレンズ材
料は、下記一般式(1)で示される化合物を主成分とす
るラジカル重合可能な組成物からなることを特徴とする
ものである。また、本発明のプラスチックレンズは、屈
折率が1.60以上であることを特徴とするものであ
る。さらに、本発明の眼鏡用レンズは、屈折率が1.6
0以上であるプラスチックレンズからなることを特徴と
するものである。 That is, the plastic lens material of the present invention is characterized by comprising a radically polymerizable composition containing a compound represented by the following general formula (1) as a main component. In addition, the plastic lens of the present invention
The folding ratio is 1.60 or more.
You. Further, the spectacle lens of the present invention has a refractive index of 1.6.
It is characterized by being made of a plastic lens that is 0 or more
Is what you do.
【0009】[0009]
【化3】 Embedded image
【0010】(式中、R1 ,R2 は水素又はメチル基
を、m、nは0〜5の整数を示す。)以下、本発明の詳
細な説明を行う。(In the formula, R 1 and R 2 each represent hydrogen or a methyl group, and m and n each represent an integer of 0 to 5.) Hereinafter, the present invention will be described in detail.
【0011】上記一般式(1)で示される化合物は、
9,9−ビス(4−ヒドロキシフェニル)−フルオレン
にメタクリル酸クロリド又はアクリル酸クロリドを反応
させた化合物や、9,9−ビス(4−ヒドロキシフェニ
ル)−フルオレンにエチレンオキシド又はプロピレンオ
キシドを平均で1〜10molの範囲で付加させた後に
メタクリル酸又はアクリル酸を反応させた化合物等が挙
げられる。これら化合物は、ラジカル重合可能な組成物
の主成分として使用され、好ましくは50〜90重量%
の範囲で使用される。 The compound represented by the general formula (1) is
9,9-bis (4-hydroxyphenyl) - fluorene and compounds obtained by reacting methacrylic acid chloride or acrylic acid chloride, 9,9-bis (4-hydroxyphenyl) - 1 fluorene ethylene oxide or propylene oxide with an average <br/> compounds obtained by reacting methacrylic acid or acrylic acid after by adding in the range of 10 mol. These compounds are radically polymerizable compositions
, Preferably 50 to 90% by weight
Used in the range.
【0012】上記したジ(メタ)アクリレートは、通
常、室温で固体であるため、眼鏡用レンズ等のプラスチ
ックレンズを製造する場合、これを溶解するモノマーが
必要となる。本発明のラジカル重合可能な組成物の具体
例としては、例えば、上記一般式(1)で示される化合
物(以下、(A)成分と示す)、(B)(A)成分及び
(C)成分以外のラジカル重合可能なビニル化合物から
選ばれる少なくとも1種のモノマー、(C)主鎖にアル
キレンオキシド鎖を有する(A)成分以外のビニル化合
物と、(D)熱重合開始剤及び/又は光重合開始剤とか
らなる組成物が挙げられる。以下、この(B)成分、
(C)成分、及び(D)成分について詳細に説明する。 Since the above-mentioned di (meth) acrylate is usually solid at room temperature, when a plastic lens such as an eyeglass lens is manufactured, a monomer for dissolving the same is required . Specific examples of the radically polymerizable composition of the present invention
As an example, for example, a compound represented by the above general formula (1)
(Hereinafter referred to as component (A)), component (B) and component (A), and
(C) From a radically polymerizable vinyl compound other than the component
At least one selected monomer, (C) an alkyl group
Vinyl compounds other than component (A) having a kylene oxide chain
And (D) thermal polymerization initiator and / or photopolymerization initiator
And a composition comprising: Hereinafter, this (B) component,
The component (C) and the component (D) will be described in detail.
【0013】(B)成分は、一般式(1)で示される化
合物(A)を溶解させるためのモノマーである。そこ
で、(A)成分及び(C)成分以外のラジカル重合可能
なビニル化合物から選ばれる少なくとも1種のモノマー
(B)であればどのようなものでもよい。具体的には、
例えば(A)成分及び(C)成分以外のメタクリレート
又はアクリレートや、スチレン、ジビニルベンゼン等の
ビニル化合物が使用可能である。 The component (B) is a compound represented by the general formula (1)
It is a monomer for dissolving the compound (A). There
And radical polymerizable other than component (A) and component (C)
At least one monomer selected from a variety of vinyl compounds
(B) Any type may be used. In particular,
For example, methacrylates other than the components (A) and (C)
Or acrylate, styrene, divinylbenzene, etc.
Vinyl compounds can be used.
【0014】溶解性の点から、フェニル(メタ)アクリ
レート、ベンジル(メタ)アクリレート、2−フェニル
フェニル(メタ)アクリレート、ナフチル(メタ)アク
リレート、スチレン、ジビニルベンゼン、ジブロモスチ
レン、クロルスチレン等が好ましい。From the viewpoint of solubility, phenyl (meth) acrylate, benzyl (meth) acrylate, 2-phenylphenyl (meth) acrylate, naphthyl (meth) acrylate, styrene, divinylbenzene, dibromostyrene, chlorostyrene and the like are preferred.
【0015】[0015]
【0016】また、プラスチックレンズの耐衝撃性、染
色性を向上させるために、(C)成分として主鎖にアル
キレンオキシド鎖を有する(A)成分以外のビニル化合
物を適量添加するのがよい。(C)成分の具体例としては特に限定されないが、ペン
タエチレングリコールジ(メタ)アクリレート、ノナエ
チレングリコールジ(メタ)アクリレート、ノナブチレ
ングリコールジ(メタ)アクリレート、ジエチレングリ
コールビスアリルカーボネート等の脂肪族モノマーが好
ましい。 本発明のプラスチックレンズは酸化防止剤、黄
変防止剤、紫外線防止剤、ブルーイング剤、顔料等の添
加剤が含まれてもよい。Further, in order to improve the impact resistance and the dyeing properties of the plastic lens, the component (C) is added to the main chain as a component.
Vinyl compounds other than component (A) having a kylene oxide chain
It is better to add an appropriate amount of the substance . Specific examples of the component (C) are not particularly limited.
Taethylene glycol di (meth) acrylate, nonae
Tylene glycol di (meth) acrylate, nonabutyle
Glycol di (meth) acrylate, diethylene glycol
Aliphatic monomers such as coal bisallyl carbonate are preferred.
Good. The plastic lens of the present invention may contain additives such as an antioxidant, an anti-yellowing agent, an ultraviolet inhibitor, a bluing agent and a pigment.
【0017】(D)成分は、(A)成分と上記のような
他のモノマーからなる組成物を成形する際には、有機過
酸化物、アゾ化合物等の熱重合開始剤、又は光重合開始
剤の1種もしくは2種以上を混合して使用する。The component (D) is used when molding a composition comprising the component (A) and another monomer as described above, or a thermal polymerization initiator such as an organic peroxide or an azo compound, or a photopolymerization initiator. One or more of the agents are used in combination.
【0018】硬化方法は、所望の形状の2枚のガラス鋳
型をエチレン−酢酸ビニル共重合体からなるガスケット
を介して型を作り、これに配合物を注入した後に加熱す
るか、紫外線等の活性エネルギー線を照射するか、ある
いはこれらの組み合わせであってもよい。このようにし
て得られた本発明のプラスチックレンズは、1.60以
上の高い屈折率を有しており、特に屈折率が1.65以
上のものも得ることも可能となり、眼鏡用レンズとして
特に好適である。 The curing method is as follows . Two glass molds having a desired shape are molded through a gasket made of an ethylene-vinyl acetate copolymer, and the mixture is poured into the mold and then heated, or heated with ultraviolet light or the like. or an active energy ray, or a combination thereof. Like this
The plastic lens of the present invention obtained by
High refractive index, especially when the refractive index is 1.65 or less.
It is also possible to obtain the above, as a spectacle lens
Particularly preferred.
【0019】[0019]
【実施例】以下に実施例及び比較例を掲げ本発明を更に
詳しく説明する。合成例1 5リットルの4つ口フラスコに、9,9−ビス(4−ヒ
ドロキシフェニル)−フルオレン(分子量350.4、
新日鉄化学(株)製)500g、脱水テトラヒドロフラ
ン2500g、トリエチルアミン300g、ハイドロキ
ノン1gを入れ、0℃に冷却しつつメタクリル酸クロリ
ド313g、脱水テトラヒドロフラン300gの混合物
を2時間にわたって滴下した。滴下終了後、室温で3時
間、50℃で3時間反応後、析出したトリエチルアミン
塩酸塩をろ過し、ろ液より、テトラヒドロフランを減圧
除去した。残った黄色固体をトルエンに溶解し、アルカ
リ水で洗浄し、トルエンを減圧留去して白色固体を得
た。The present invention will be described in more detail with reference to the following Examples and Comparative Examples. Synthesis Example 1 In a 5-liter four-necked flask, 9,9-bis (4-hydroxyphenyl) -fluorene (molecular weight 350.4,
500 g of Nippon Steel Chemical Co., Ltd., 2500 g of dehydrated tetrahydrofuran, 300 g of triethylamine and 1 g of hydroquinone were added, and a mixture of 313 g of methacrylic chloride and 300 g of dehydrated tetrahydrofuran was added dropwise over 2 hours while cooling to 0 ° C. After the completion of the dropwise addition, the reaction was carried out at room temperature for 3 hours and at 50 ° C. for 3 hours. The precipitated triethylamine hydrochloride was filtered, and tetrahydrofuran was removed from the filtrate under reduced pressure. The remaining yellow solid was dissolved in toluene, washed with alkaline water, and toluene was distilled off under reduced pressure to obtain a white solid.
【0020】実施例1 合成例1で得た9,9−ビス(4−メタクリロキシフェ
ニル)−フルオレン60g、スチレン40g、触媒とし
て2,2′−アゾビス(2,4−ジメチルバレロニトリ
ル)を0.05g混合し、液状配合物を作成した。 Example 1 60 g of 9,9-bis (4-methacryloxyphenyl) -fluorene obtained in Synthesis Example 1, 40 g of styrene, and 2,2'-azobis (2,4-dimethylvaleronitrile) as a catalyst in 0 g were used. 0.05g was mixed to form a liquid formulation.
【0021】次に、縦100mm、横100mm、厚さ
5mmの強化ガラスと外径6mm(板厚2mm用)、外
形10mm(板厚5mm用)の塩化ビニル製チューブ状
ガスケットとで構成された鋳型内に前記の配合物を注入
し、80℃で3時間、ひき続き120℃で3時間かけて
加熱硬化させた。硬化物を鋳型より脱型し、硬化物の内
部歪を除去するため100℃で1時間かけ加熱処理し、
透明な平板を得た。Next, a mold made of tempered glass having a length of 100 mm, a width of 100 mm and a thickness of 5 mm and a tubular gasket made of vinyl chloride having an outer diameter of 6 mm (for a thickness of 2 mm) and an outer diameter of 10 mm (for a thickness of 5 mm) The above formulation was poured into the mixture, and the mixture was cured by heating at 80 ° C. for 3 hours and subsequently at 120 ° C. for 3 hours. The cured product is released from the mold, and heated at 100 ° C. for 1 hour to remove internal strain of the cured product,
A transparent plate was obtained.
【0022】この平板は、可視光線透過率は90%であ
り、屈折率(589.3mmのD線)は1.675と高
かった。さらに、TMAによるTgは250℃であり、
アセトン、トルエン等の耐薬品性も優れていた。This plate had a visible light transmittance of 90% and a high refractive index (589.3 mm D-line) of 1.675. Further, Tg by TMA is 250 ° C.,
The chemical resistance of acetone, toluene, etc. was also excellent.
【0023】合成例2 5リットルの4つ口フラスコに、9,9−ビス(4−ヒ
ドロキシフェニル)−フルオレン1molに対し、エチ
レンオキシド4molを付加した9,9−ビス(4−ヒ
ドロキシジエトキシフェニル)−フルオレン800g、
トルエン2.5kg、メタクリル酸600g、ハイドロ
キノン1gおよび硫酸50gを入れ、120℃で撹拌を
行いながら副生した水をトルエンで共沸除去し4時間反
応させた。反応後トルエンを1kg加え、アルカリ水で
洗浄し、トルエンを減圧留去して9,9−ビス(4−メ
タクリロキシジエトキシフェニル)−フルオレンを得
た。 実施例2 合成例2で得た9,9−ビス(4−メタクリロキシジエ
トキシフェニル)−フルオレン60g、ベンジルメタク
リレート20g、ノナエチレングリコールジアクリレー
ト20g、触媒として2,2′−アゾビス(2,1−ジ
メチルバレロニトリル)を0.05g混合し、液状配合
物を作成した。[0023]Synthesis Example 2 In a 5 liter four-necked flask, add 9,9-bis (4-H
(Droxyphenyl) -fluorene (1 mol)
9,9-bis (4-H
800 g of droxydiethoxyphenyl) -fluorene,
2.5 kg of toluene, 600 g of methacrylic acid, hydro
Add 1 g of quinone and 50 g of sulfuric acid and stir at 120 ° C.
Azeotropically remove by-product water with toluene while performing
I responded. After the reaction, add 1 kg of toluene, and add
After washing, the toluene was distilled off under reduced pressure to give 9,9-bis (4-medium).
(Tacryloxydiethoxyphenyl) -fluorene
Was. Example 2 9,9-bis (4-methacryloxydie obtained in Synthesis Example 2
60 g of toxicphenyl) -fluorene, benzyl methac
Relate 20g, Nonaethylene glycol diacrylate
20g, 2,2'-azobis (2,1-di
Methyl valeronitrile) mixed with 0.05g
Created things.
【0024】次に、縦100mm、横100mm、厚さ
5mmの強化ガラスと外径6mm(板厚2mm用)、の
塩化ビニル製チューブ状ガスケットとで構成された鋳型
内に前記の配合物を注入し、80℃で3時間、ひき続き
120℃で3時間かけて加熱硬化させた。硬化物を鋳型
より脱型し、硬化物の内部歪を除去するため100℃で
1時間かけ加熱処理し、透明な平板を得た。Next, the above compound was poured into a mold composed of tempered glass having a length of 100 mm, a width of 100 mm and a thickness of 5 mm and a tubular gasket made of vinyl chloride having an outer diameter of 6 mm (for a plate thickness of 2 mm). Then, the mixture was cured by heating at 80 ° C. for 3 hours and subsequently at 120 ° C. for 3 hours. The cured product was removed from the mold and subjected to heat treatment at 100 ° C. for 1 hour to remove internal strain of the cured product, to obtain a transparent flat plate.
【0025】この平板は、可視光線透過率は91%であ
り、屈折率(589.3mmのD線)は1.643であ
った。さらに、TMAによるTgは195℃であり、ア
セトン、トルエン等の耐薬品性も優れていた。This flat plate had a visible light transmittance of 91% and a refractive index (D line of 589.3 mm) of 1.643. Further, Tg by TMA was 195 ° C., and the chemical resistance of acetone, toluene, and the like was excellent.
【0026】比較例1 ジエチレングリコ−ルビスアリルカーボネート100
g、ジイソプロピルパーオキシカーボネート2.5gを
混合し、実施例1、2で示した鋳型中に入れ40℃で1
0時間、60℃で5時間、90℃で5時間保持して硬化
させた。脱型後100℃で1時間加熱処理した。 Comparative Example 1 Diethylene glycol bisallyl carbonate 100
g, 2.5 g of diisopropyl peroxycarbonate, and put in the mold shown in Examples 1 and 2 at 40 ° C.
Curing was carried out by holding at 0 ° C, 5 hours at 60 ° C, and 5 hours at 90 ° C. After demolding, heat treatment was performed at 100 ° C. for 1 hour.
【0027】この平板は、可視光線透過率は92%、屈
折率(589.3mmのD線)は1.499であった。
TMAによるTgは80℃であった。This flat plate had a visible light transmittance of 92% and a refractive index (D line of 589.3 mm) of 1.499.
The Tg by TMA was 80 ° C.
【0028】[0028]
【発明の効果】上記の実施例に実証されるように、本発
明のプラスチックレンズ材料は屈折率が1.60以上、
特に1.65以上の高屈折率のプラスチックレンズ、眼
鏡用レンズを得ることができる。また、このようなプラ
スチックレンズ材料から得られた本発明のプラスチック
レンズは、耐熱性、表面硬度、耐薬品性にも優れてい
る。According to the present invention as demonstrated in the above examples, the plastic lens materials of the present invention has a refractive index of 1.60 or more,
Especially high refractive index plastic lens of 1.65 or more , eye
A mirror lens can be obtained. In addition, such a plastic
The plastic of the present invention obtained from a stick lens material
Lenses are also excellent in heat resistance, surface hardness, and chemical resistance.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平3−41110(JP,A) 特開 平3−84031(JP,A) 特開 昭61−118409(JP,A) 特開 昭55−13747(JP,A) (58)調査した分野(Int.Cl.7,DB名) C08G 220/30 C08G 299/02 G02B 1/04 G02C 7/02 CA,REGISTRY(STN)──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-3-41110 (JP, A) JP-A-3-84031 (JP, A) JP-A-61-118409 (JP, A) JP-A-55- 13747 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) C08G 220/30 C08G 299/02 G02B 1/04 G02C 7/02 CA, REGISTRY (STN)
Claims (4)
分とするラジカル重合可能な組成物であることを特徴と
するプラスチックレンズ材料。 【化1】 (式中、R1、R2は水素又はメチル基を、m、nは0
〜5の整数を示す。) 1. A plastic lens material which is a radically polymerizable composition containing a compound represented by the following general formula (1) as a main component. Embedded image (Wherein, R1 and R2 represent hydrogen or a methyl group, and m and n represent 0
Represents an integer of from 5 to 5. )
式(1)で示される化合物、(B)(A)成分及び
(C)成分以外のラジカル重合可能なビニル化合物から
選ばれる少なくとも1種のモノマー、(C)主鎖にアル
キレンオキシド鎖を有する(A)成分以外のビニル化合
物と、(D)熱重合開始剤及び/又は光重合開始剤とか
らなることを特徴とする請求項1記載のプラスチックレ
ンズ材料。 【化2】 (式中、R1、R2は水素又はメチル基を、m、nは0
〜5の整数を示す。) 2. A radically polymerizable composition comprising: (A) a compound represented by the general formula (1); and (B) a radically polymerizable vinyl compound other than the components (A) and (C). The composition according to claim 1, comprising one kind of monomer, (C) a vinyl compound other than the component (A) having an alkylene oxide chain in the main chain, and (D) a thermal polymerization initiator and / or a photopolymerization initiator. 2. The plastic lens material according to 1. Embedded image (Wherein, R1 and R2 represent hydrogen or a methyl group, and m and n represent 0
Represents an integer of from 5 to 5. )
ンズ材料から得られた、屈折率が1.60以上であるこ
とを特徴とするプラスチックレンズ。3. A plastic lens obtained from the plastic lens material according to claim 1 and having a refractive index of 1.60 or more.
ンズ材料から得られた、屈折率が1.60以上であるこ
とを特徴とする眼鏡用レンズ。4. A spectacle lens obtained from the plastic lens material according to claim 1 and having a refractive index of 1.60 or more.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03097322A JP3130555B2 (en) | 1991-04-26 | 1991-04-26 | Plastic lens materials, plastic lenses and spectacle lenses |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP03097322A JP3130555B2 (en) | 1991-04-26 | 1991-04-26 | Plastic lens materials, plastic lenses and spectacle lenses |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04325508A JPH04325508A (en) | 1992-11-13 |
JP3130555B2 true JP3130555B2 (en) | 2001-01-31 |
Family
ID=14189248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP03097322A Expired - Lifetime JP3130555B2 (en) | 1991-04-26 | 1991-04-26 | Plastic lens materials, plastic lenses and spectacle lenses |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3130555B2 (en) |
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