JPS58164608A - Resin for plastic lens - Google Patents

Resin for plastic lens

Info

Publication number
JPS58164608A
JPS58164608A JP4781582A JP4781582A JPS58164608A JP S58164608 A JPS58164608 A JP S58164608A JP 4781582 A JP4781582 A JP 4781582A JP 4781582 A JP4781582 A JP 4781582A JP S58164608 A JPS58164608 A JP S58164608A
Authority
JP
Japan
Prior art keywords
resin
refractive index
lens
high refractive
acrylic acid
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.)
Pending
Application number
JP4781582A
Other languages
Japanese (ja)
Inventor
Tadanori Fukuda
福田 忠則
Hiroyuki Fukuda
博之 福田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toray Industries Inc
Original Assignee
Toray Industries Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Toray Industries Inc filed Critical Toray Industries Inc
Priority to JP4781582A priority Critical patent/JPS58164608A/en
Publication of JPS58164608A publication Critical patent/JPS58164608A/en
Pending legal-status Critical Current

Links

Abstract

PURPOSE:The titled resin capable of forming lenses having excellent impact resistance and bending elasticity and a high refractive index, comprising a polymer prepared by addition-polymerizing a vinyl monomer compound mixture containing a (meth)acrylic acid metal salt. CONSTITUTION:A resin for plastic lenses, comprising a polymer prepared by addition-polymerizing a vinyl monomer compound containing above 30wt% (meth)acrylic acid metal salt of the formula, wherein X is H or CH3 and M is a metal, e.g., Pb, Ba, Zn or Al. Tough plastic lenses having a relatively low shrinkage during molding, and a high refractive index and excellent impact resistance and bending elasticity can be obtained and the size or thickness reduction of a lens is possible because of a high refractive index.

Description

【発明の詳細な説明】 本発明は、眼鏡プラスチックレンズ用樹脂に関するもの
である。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a resin for eyeglass plastic lenses.

プラスチックレンズは、ガラスレンズ′に比べて作り易
く、また軽量で耐衝撃性が良いために眼鏡レンズに用い
た場合に安全性が高いという利点がある。従来のプラス
チックレンズ用樹脂には、アクリル樹脂、ポリカーボネ
ート樹脂、アリルジグリコールカーボネート樹脂、ポリ
スチレン樹脂等力使用されている。このうち視力矯正用
眼鏡用プラスチックレンズとして広く使われているのは
Plastic lenses have the advantage of being easier to manufacture than glass lenses, and are also lightweight and have good impact resistance, making them highly safe when used in eyeglass lenses. Conventional plastic lens resins include acrylic resin, polycarbonate resin, allyl diglycol carbonate resin, and polystyrene resin. Among these, which plastic lenses are widely used for vision correction glasses.

熱硬化性樹脂であるジエチレングリコールビスアリルカ
ーボネートである。この樹脂は、耐衝撃性がすぐれるこ
と、レンズ度数が温度の変化で大きく変わらないこと、
さらに切削性、加工性が良好である等種々の特長を有し
ている。
Diethylene glycol bisallyl carbonate is a thermosetting resin. This resin has excellent impact resistance, and the lens power does not change significantly with changes in temperature.
Furthermore, it has various features such as good machinability and workability.

しかし、ジエチレングリコールビスアリルカー□ボネー
トは屈折率が1.50であり、この樹脂をレンズにした
場合、ガラスレンズに比べてレンズの厚みが大きくなる
という欠点がある。これはレンズ度数が大きくなると特
に顕著である。
However, diethylene glycol bisallyl carbonate has a refractive index of 1.50, and when this resin is used as a lens, there is a drawback that the lens is thicker than a glass lens. This is particularly noticeable when the lens power increases.

とくに近年、プラスチックレンズの小型化、薄型化が求
望されており、それを可能とする高屈折率を有するプラ
スチックレンズ用樹脂の必要性が出てきた。
In particular, in recent years, there has been a demand for plastic lenses to be smaller and thinner, and there has been a need for resins for plastic lenses that have a high refractive index that makes this possible.

本発明者らは、上記の問題点を解決して、高屈折率を与
えるプラスチックレンズ用樹脂について鋭意検討した結
果、以下に述べる本発明に到達した。
The inventors of the present invention solved the above-mentioned problems and conducted extensive studies on resins for plastic lenses that provide a high refractive index, and as a result, they arrived at the present invention described below.

すなわち本発明は9次の一般式で表わされる化金物を少
なくとも60重量%含有してなるビニル単量体化合物を
付加重合して得られる重合体からなることを特徴とする
プラスチックレンズ用樹脂に関するものである。
That is, the present invention relates to a resin for plastic lenses characterized by being made of a polymer obtained by addition polymerization of a vinyl monomer compound containing at least 60% by weight of a metal compound represented by the following general formula: It is.

OH,=O−0−0−M−0−0−C!= OH。OH,=O-0-0-M-0-0-C! = OH.

(Xは水素またはメチル基9Mは金属)本発明で使用す
る上記一般式の化合物は、アクリル酸またはメタアクリ
ル酸の金属塩である。金属の種類としては、屈折率を高
めるために、金属の原子量の大きい方が好ましい、水や
空気と反応しやすい金属、光に対して不安定な金属、放
射性を有する金属は好ましくな諭。
(X is hydrogen or methyl group 9M is metal) The compound of the above general formula used in the present invention is a metal salt of acrylic acid or methacrylic acid. Regarding the type of metal, in order to increase the refractive index, metals with a large atomic weight are preferred; metals that easily react with water and air, metals that are unstable to light, and metals that are radioactive are not preferred.

好適な金属としては1例求ば鉛、ビスマス、り1□ リウム、バリウム、スズ9.?ルコニウム、亜鉛。Examples of suitable metals include lead, bismuth, and 1□ Lium, barium, tin9. ? luconium, zinc.

リン、アルミニウム等である。These include phosphorus and aluminum.

一方9本発明で使用する1記の金属塩と共に用いるビニ
ル単量体は、共重合可能なものであればいずれでもよい
。しかし該ビニル単量体としては無色透明の液状物で、
かつ金属塩を溶解させるものが良好である。例えば次の
ようなビニル単量体が好適である。
On the other hand, the vinyl monomer used together with the metal salt mentioned above in the present invention may be any vinyl monomer as long as it is copolymerizable. However, the vinyl monomer is a colorless and transparent liquid,
Also, those that dissolve metal salts are preferable. For example, the following vinyl monomers are suitable.

アクリル酸 ン゛1タクリル酸 アクリル酸−2−ヒドロキシエチル メタクリル酸−2−ヒドロキシエチル ジアリルクロレンデート ジメタリルクロレンデート また上記のビニル単量体と共にさらに下記のビニル単量
体を併用して使用することもできる。このようなビニル
単量体としては0例えば次のようなものがある。
Acrylic acid 1-Tacrylic acid Acrylic acid-2-Hydroxyethyl Methacrylic acid-2-Hydroxyethyl diallyl chlorendate Dimethallyl chlorendate Additionally, the following vinyl monomers are used in combination with the above vinyl monomers. You can also. Examples of such vinyl monomers include the following.

スチレン ・ ジアリルフタレート エチレンイリコールジメタクリレート メタクリベ酸メチル 、:。Styrene・ diallyl phthalate Ethylene ylicol dimethacrylate Methyl methacrivate , :.

アクリル酸壬チル アクリル酸メチル 本発明で用いるアクリル酸またはメタアクリル酸の金属
塩の含量は、屈折率を少なくとも1.55以上に高める
目的から0重合体中、少なくとも30重量%以上含有さ
せることが必要である。
The content of the metal salt of acrylic acid or methacrylic acid used in the present invention is at least 30% by weight in the polymer in order to increase the refractive index to at least 1.55. is necessary.

本発明のプラスチックレンズ用樹脂を用いたプラスチッ
クレンズの製造方法を一般的に説明すると次のとおりで
ある。
A general explanation of the method for manufacturing a plastic lens using the resin for plastic lenses of the present invention is as follows.

製造方法としては、注型重合法と射出成形法に大別され
る。
Manufacturing methods are broadly divided into cast polymerization and injection molding.

注型重合法の特徴は、原料モノマから直接に重合硬化さ
せると同時に、レンズ状に成形されることにある。した
がってレンズに成形ひずみが少なく、光学的にも均一性
にすぐれる特徴があり、市販プラスチック製の度つきレ
ンズのほとんどが現在この方法であると言われる。
The feature of the cast polymerization method is that it directly polymerizes and hardens the raw material monomer and simultaneously forms it into a lens shape. Therefore, the lenses have little molding distortion and are characterized by excellent optical uniformity, and it is said that most prescription lenses made of plastic on the market are currently made using this method.

一方、射出成形法は、予め重合した樹脂をレンズ状に射
出成形する方法で、サングラスやファッショングラスを
対象にメタクリル樹脂やポリカーボネート樹脂がこの方
法で製造されている。射出成形は、レンズ成形品に光学
的′成形ひずみが少ないようにすることが必要であり、
金型設計と成形条件の設定が重要な問題となる。
On the other hand, injection molding is a method in which pre-polymerized resin is injected into the shape of a lens, and methacrylic resin and polycarbonate resin are manufactured using this method for sunglasses and fashion glasses. In injection molding, it is necessary to ensure that the lens molded product has little optical distortion.
Mold design and molding condition settings are important issues.

通常重合開始剤を加えて、予備的にある程度反応を進行
させ(予備重合)、空気等の溶存ガスを真空脱気した後
に、金型に注入し、加熱して重合させる方法である。
Usually, a polymerization initiator is added, the reaction is preliminarily allowed to proceed to some extent (prepolymerization), dissolved gases such as air are degassed under vacuum, and then the mixture is poured into a mold and polymerized by heating.

加熱温度は最初比較的低温(たとえば40〜50℃)で
反応を行ない0反応の進行とともに温度を11[1℃程
度まで上昇させて、ゆっくり付加重合させることが、レ
ンズのひずみを少なくさせる点で好ましい。
The heating temperature is such that the reaction is initially carried out at a relatively low temperature (for example, 40 to 50 degrees Celsius), and as the reaction progresses, the temperature is increased to about 11 [1 degrees Celsius, for slow addition polymerization, which reduces distortion of the lens. preferable.

重合開始剤としては、公知の各種のものを使用できるが
、所望の反応温度に応じて選択すべきである。たとえば
、1.1−アゾビスシクロヘキサンカーボネート、ジイ
ンプロピルパーオキシカーボネート、1,1/−アゾビ
スシクロヘキサンナイトレート、ジーtert−ブチル
パーオキサイドなどが良好である。
Various known polymerization initiators can be used, but should be selected depending on the desired reaction temperature. For example, 1,1-azobiscyclohexane carbonate, diimpropyl peroxycarbonate, 1,1/-azobiscyclohexane nitrate, di-tert-butyl peroxide, and the like are suitable.

本発明の樹脂を樹脂成分とするプラスチックレンズは市
販のプラスチックレンズに比べて次のような特徴を有し
ている。
The plastic lens containing the resin of the present invention as a resin component has the following characteristics compared to commercially available plastic lenses.

1. 強靭なプラスチックレンズが得られる。1. A strong plastic lens can be obtained.

2、 耐衝撃性がすぐれる。2. Excellent impact resistance.

3 無色透明な樹脂が得られる。3. A colorless and transparent resin is obtained.

4、成形重合時の収縮率が比較的小さい。4. The shrinkage rate during molding polymerization is relatively small.

5、屈折率が高い。5. High refractive index.

6、 曲げ弾性がすぐれる。6. Excellent bending elasticity.

一本発明の樹脂を樹脂成分とするプラスチックレンズは
0反射防止、高硬度付与、耐摩耗性、耐薬品性向上、防
曇性付与などの表面改質を行なうため、公知の物理的あ
るいは化学的方法を施すことが可能である。
1) Plastic lenses containing the resin of the present invention as a resin component can be subjected to surface modification such as anti-reflection, high hardness, abrasion resistance, improved chemical resistance, and anti-fogging properties using known physical or chemical methods. It is possible to apply the method.

以下、実施例により本発明を更に詳しく説明する。なお
0例中の屈折率は、波長が5892.9AOD線におけ
る値である。
Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that the refractive index in Example 0 is a value at a wavelength of 5892.9 AOD line.

実施例1 アクリル酸の鉛塩80重量部、:およびアクリル酸−2
−ヒドロキシエチル20重量部を混合し、均一な溶液を
作製する。この混合液にラジカル重合開始剤として、ジ
ーtert−ブチルパーオキサイドを1重量部添加し、
均一に混合した後、レンズ型に注入し、80℃、3時間
e100℃15時間。
Example 1 80 parts by weight of lead salt of acrylic acid: and acrylic acid-2
- Mix 20 parts by weight of hydroxyethyl to create a homogeneous solution. To this mixed solution, 1 part by weight of di-tert-butyl peroxide was added as a radical polymerization initiator,
After uniformly mixing, pour into a lens mold and heat at 80°C for 3 hours and at 100°C for 15 hours.

その後110℃で1時間熱処理した。Thereafter, it was heat treated at 110°C for 1 hour.

得られた重合体成形品は、無色透明で硬く、屈折率は1
.61と非常に高かった。
The obtained polymer molded product is colorless, transparent, hard, and has a refractive index of 1.
.. It was extremely high at 61.

実施例2 メタクリル酸のバリウム塩70重量部、ジアリルクロシ
ンデート10重量部、およびアクリル酸20重量部を均
一に混合して金属塩を溶解させ。
Example 2 70 parts by weight of barium salt of methacrylic acid, 10 parts by weight of diallyl crocindate, and 20 parts by weight of acrylic acid were uniformly mixed to dissolve the metal salt.

この混合液に重合開始剤としてジイソ゛プロビルパーオ
キシカーポネートを1重量部加えて均一に混合した。こ
の溶液をレンズ型に流し込み、50’0で3時間、40
℃で3時間、5o℃で6時間、 60℃で10時間加熱
を続けた。
1 part by weight of diisopropyl peroxy carbonate as a polymerization initiator was added to this mixed solution and mixed uniformly. Pour this solution into a lens mold and hold it at 50'0 for 3 hours.
Heating was continued for 3 hours at 50°C, 6 hours at 50°C, and 10 hours at 60°C.

得られた重合体成形品は透明で硬く、屈折率は1.60
と高かった。: 優 ′5゜
The obtained polymer molded product is transparent and hard, and has a refractive index of 1.60.
It was expensive. : Yu'5゜

Claims (1)

【特許請求の範囲】[Claims] (1)  次の一般式で表わされる化合物を少なくとも
30重量%含有してなるビニル単I体化合物を付加重合
ルて得られる重合体からなることを特徴とするプラスチ
ックレンズ用樹脂。 (Xは水素またはメチル基1Mは金属)
(1) A resin for plastic lenses, characterized by comprising a polymer obtained by addition polymerization of a vinyl monomer compound containing at least 30% by weight of a compound represented by the following general formula. (X is hydrogen or methyl group 1M is metal)
JP4781582A 1982-03-25 1982-03-25 Resin for plastic lens Pending JPS58164608A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4781582A JPS58164608A (en) 1982-03-25 1982-03-25 Resin for plastic lens

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4781582A JPS58164608A (en) 1982-03-25 1982-03-25 Resin for plastic lens

Publications (1)

Publication Number Publication Date
JPS58164608A true JPS58164608A (en) 1983-09-29

Family

ID=12785851

Family Applications (1)

Application Number Title Priority Date Filing Date
JP4781582A Pending JPS58164608A (en) 1982-03-25 1982-03-25 Resin for plastic lens

Country Status (1)

Country Link
JP (1) JPS58164608A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6028413A (en) * 1983-07-27 1985-02-13 Hitachi Ltd Transparent resin
JPS6356510A (en) * 1986-08-26 1988-03-11 Nippon Paint Co Ltd Disintegrating type vinyl resin particle
US5298569A (en) * 1985-10-30 1994-03-29 Nippon Paint Co. Metallic ester acrylic compositions capable of releasing bioactive substance at a controlled rate
JP2006182910A (en) * 2004-12-27 2006-07-13 Mitsui Chemicals Inc Metal-containing (meth)acrylic compound and its use
US20150192851A1 (en) * 2013-12-05 2015-07-09 Tokyo Ohka Kogyo Co., Ltd. Negative resist composition, method of forming resist pattern, and complex

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6028413A (en) * 1983-07-27 1985-02-13 Hitachi Ltd Transparent resin
US5298569A (en) * 1985-10-30 1994-03-29 Nippon Paint Co. Metallic ester acrylic compositions capable of releasing bioactive substance at a controlled rate
JPS6356510A (en) * 1986-08-26 1988-03-11 Nippon Paint Co Ltd Disintegrating type vinyl resin particle
JP2006182910A (en) * 2004-12-27 2006-07-13 Mitsui Chemicals Inc Metal-containing (meth)acrylic compound and its use
US20150192851A1 (en) * 2013-12-05 2015-07-09 Tokyo Ohka Kogyo Co., Ltd. Negative resist composition, method of forming resist pattern, and complex
US9366960B2 (en) * 2013-12-05 2016-06-14 Tokyo Oha Kogyo Co., Ltd. Negative resist composition, method of forming resist pattern, and complex
US9499646B2 (en) 2013-12-05 2016-11-22 Tokyo Ohka Kogyo Co., Ltd. Negative resist composition, method of forming resist pattern and complex

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