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JPH0223841B2 - - Google Patents

Info

Publication number
JPH0223841B2
JPH0223841B2 JP55099464A JP9946480A JPH0223841B2 JP H0223841 B2 JPH0223841 B2 JP H0223841B2 JP 55099464 A JP55099464 A JP 55099464A JP 9946480 A JP9946480 A JP 9946480A JP H0223841 B2 JPH0223841 B2 JP H0223841B2
Authority
JP
Japan
Prior art keywords
refractive index
lens
present
high refractive
phenyl methacrylate
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
Application number
JP55099464A
Other languages
Japanese (ja)
Other versions
JPS5723901A (en
Inventor
Jiro Tarumi
Shigeo Komya
Mitsuo Sugimura
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.)
Hoya Corp
Original Assignee
Hoya Corp
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 Hoya Corp filed Critical Hoya Corp
Priority to JP9946480A priority Critical patent/JPS5723901A/en
Publication of JPS5723901A publication Critical patent/JPS5723901A/en
Publication of JPH0223841B2 publication Critical patent/JPH0223841B2/ja
Granted legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F218/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F218/14Esters of polycarboxylic acids
    • C08F218/16Esters of polycarboxylic acids with alcohols containing three or more carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は、高屈折率を有するプラスチツクレン
ズに関するものである。近年、無機ガラスに代つ
て有機ガラスを素材とするレンズが普及してきて
いる。有機ガラスは、軽量、安全性(優れた耐衝
撃性)、易加工性、染色性等の無機ガラスでは満
たしえない利点を有しており、既にジエチレング
リコールビスアリルカーボネート(以下CR39と
呼ぶ)が広く利用されている。しかしながら、
CR39から成るレンズは屈折率が1.499と無機ガラ
スに比較して低いために、レンズ肉厚が厚くなる
欠点を有している。このような欠点を解決するた
めに、CR39とベンジルメタクリレート等を共重
合して、屈折率を高める方法が知られている。し
かし、ベンジルメタクリレートをCR39と共重合
させたレンズは表面硬度がCR39より劣るために、
レンズの取り扱いに注意を要するという欠点を有
していた。また、CR39とトリアリルイソシアヌ
レートを共重合させると、容易に屈折率を上げる
ことができるが、亀裂が入りやすくレンズになり
にくい欠点があつた。 本発明者らは、上記欠陥を改善すべく鋭意研究
した結果、CR39とトリアリルイソシアヌレート
の系にフエニルメタクリレートを加えて共重合す
ると、表面硬度の著しく優れた高屈折率レンズが
得られることを見いだし、本発明に到達した。 すなわち、本発明の目的は、高屈折率と良好な
表面硬度を有するプラスチツクレンズを提供する
ことにある。 このような本発明の目的とするレンズは、
CR39、トリアリルイソシアヌレート及びフエニ
ルメタクリレートの3成分を共重合することによ
り得られる。 本発明で用いられるCR39の好適使用量は、80
〜40重量%の範囲であり、トリアリルイソシアヌ
レートの好適使用量は、10〜30重量%の範囲であ
る。フエニルメタクリレートの好適使用量は、10
〜30重量%の範囲である。トリアリルイソシアヌ
レートが30重量%を越えると、レンズにクラツク
が入りやすくなり好ましくない。また、フエニル
メタクリレートが10%未満の場合も、レンズにク
ラツクが入りやすい。 本発明にこのような高屈折率レンズの作製は、
CR39、トリアリルイソシアヌレート、フエニル
メタクリレート及びラジカル発生剤とを混合した
混合液をガラスモールドと樹脂製ガスケツトによ
つて組み立てられた鋳型中に流し込み、加熱ある
いは紫外線照射等の方法を用いて硬化させること
によつて行われる。 このような本発明にかかる高屈折率レンズは、
従来知られていた単に屈折率の高いベンジルメタ
クリレートをCR39と混合して、重合したレンズ
と異なり、より高い表面硬度、良好な透明性、優
れたコート性を有している。すなわち、本発明に
かかるレンズは、CR39の有する優れたレンズ物
性を損わずに、高屈折率と表面硬度を改良したも
のであり、CR39とベンジルメタクリレートの2
成分系共重合体では考えられない程の効果を発現
している。 次に、本発明の詳細を実施例によつて説明す
る。なお、実施例中の部は、いずれも重量部であ
る。 実施例 1 CR39 60部、フエニルメタクリレート20部、ト
リアリルイソシアヌレート20部及びジイソプロピ
ルパーオキシジカーボネート4部から成る混合液
を2枚のガラスモールドとエチレン−酢ビ共重合
樹脂製ガスケツトにより組み立てられた鋳型中に
流し込み、24時間かけて40℃から90℃まで加熱し
た。重合終了後、レンズを鋳型から取り出し、
120℃で1時間アニーリングした。得られたレン
ズの屈折率は1.526、アツベ数は48、透過率92%
(550nm)、鉛筆硬度は4H、耐衝撃性はFDA規格
に合格する良好なレンズ物性を有していた。ま
た、真空蒸着によつてコーテイングしたガラスコ
ート膜の密着性クロスカツトテスト、耐アルカリ
性テスト)も合格であつた。比較例に挙げたレン
ズよりも著しく優れた物性を有していた。 実施例 2〜4 次に、実施例1と同様の条件で作製したレンズ
物性を第1表に示す。
The present invention relates to a plastic lens with a high refractive index. In recent years, lenses made of organic glass instead of inorganic glass have become popular. Organic glass has advantages that cannot be met by inorganic glass, such as light weight, safety (excellent impact resistance), ease of processing, and dyeability, and diethylene glycol bisallyl carbonate (hereinafter referred to as CR39) is already widely used. It's being used. however,
Lenses made of CR39 have a refractive index of 1.499, which is lower than that of inorganic glass, so they have the disadvantage of being thicker. In order to solve these drawbacks, a method is known in which CR39 is copolymerized with benzyl methacrylate or the like to increase the refractive index. However, lenses made by copolymerizing benzyl methacrylate with CR39 have a surface hardness inferior to that of CR39, so
This has the disadvantage that the lens must be handled with care. Furthermore, by copolymerizing CR39 and triallylisocyanurate, the refractive index can be easily increased, but it has the drawback that it is prone to cracking and is difficult to form into lenses. As a result of intensive research aimed at improving the above-mentioned defects, the inventors of the present invention found that by copolymerizing a system of CR39 and triallylisocyanurate with the addition of phenyl methacrylate, a high refractive index lens with significantly superior surface hardness can be obtained. They discovered this and arrived at the present invention. That is, an object of the present invention is to provide a plastic lens having a high refractive index and good surface hardness. The objective lens of the present invention is as follows:
It is obtained by copolymerizing three components: CR39, triallyl isocyanurate, and phenyl methacrylate. The preferred amount of CR39 used in the present invention is 80
-40% by weight, and the preferred amount of triallyl isocyanurate is in the range of 10-30% by weight. The preferred amount of phenyl methacrylate is 10
~30% by weight. If triallyl isocyanurate exceeds 30% by weight, cracks tend to form in the lens, which is undesirable. Also, if the phenyl methacrylate content is less than 10%, cracks are likely to occur in the lens. The production of such a high refractive index lens according to the present invention includes:
A mixture of CR39, triallyl isocyanurate, phenyl methacrylate, and a radical generator is poured into a mold assembled with a glass mold and a resin gasket, and cured using methods such as heating or ultraviolet irradiation. It is done by certain things. Such a high refractive index lens according to the present invention,
Unlike conventionally known lenses made by simply mixing benzyl methacrylate with a high refractive index with CR39 and polymerizing it, it has higher surface hardness, good transparency, and excellent coating properties. That is, the lens according to the present invention has improved high refractive index and surface hardness without impairing the excellent lens physical properties of CR39, and is a combination of CR39 and benzyl methacrylate.
It exhibits effects that would be unimaginable for component-based copolymers. Next, the details of the present invention will be explained with reference to examples. Note that all parts in the examples are parts by weight. Example 1 A mixed solution consisting of 60 parts of CR39, 20 parts of phenyl methacrylate, 20 parts of triallyl isocyanurate and 4 parts of diisopropyl peroxydicarbonate was assembled using two glass molds and a gasket made of ethylene-vinyl acetate copolymer resin. The mixture was poured into a mold and heated from 40°C to 90°C over 24 hours. After polymerization, remove the lens from the mold,
Annealing was performed at 120°C for 1 hour. The obtained lens has a refractive index of 1.526, an Atsube number of 48, and a transmittance of 92%.
(550 nm), pencil hardness was 4H, and impact resistance passed FDA standards. Furthermore, the glass coated film coated by vacuum deposition passed the adhesion cross-cut test and alkali resistance test). It had significantly better physical properties than the lenses listed as comparative examples. Examples 2 to 4 Next, the physical properties of lenses manufactured under the same conditions as in Example 1 are shown in Table 1.

【表】【table】

【表】 〓
〓△印:膜強度がCR39より
劣る
[Table] 〓
〓△mark: Film strength is inferior to CR39

Claims (1)

【特許請求の範囲】[Claims] 1 ジエチレングリコールビスアリルカーボネー
ト、トリアリルイソシアヌート及びフエニルメタ
クリレートの共重合体より成る表面硬度が鉛筆硬
度3H以上の高屈折率プラスチツクレンズ。
1. A high refractive index plastic lens with a surface hardness of 3H or more on the pencil hardness, which is made of a copolymer of diethylene glycol bisallyl carbonate, triallyl isocyanate, and phenyl methacrylate.
JP9946480A 1980-07-21 1980-07-21 Lens with high refractive index and high surface hardness Granted JPS5723901A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP9946480A JPS5723901A (en) 1980-07-21 1980-07-21 Lens with high refractive index and high surface hardness

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP9946480A JPS5723901A (en) 1980-07-21 1980-07-21 Lens with high refractive index and high surface hardness

Publications (2)

Publication Number Publication Date
JPS5723901A JPS5723901A (en) 1982-02-08
JPH0223841B2 true JPH0223841B2 (en) 1990-05-25

Family

ID=14248025

Family Applications (1)

Application Number Title Priority Date Filing Date
JP9946480A Granted JPS5723901A (en) 1980-07-21 1980-07-21 Lens with high refractive index and high surface hardness

Country Status (1)

Country Link
JP (1) JPS5723901A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6408751B1 (en) * 2017-02-21 2018-10-17 三井化学株式会社 Polymerizable composition for optical material, optical material obtained from the composition, and plastic lens

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS537789A (en) * 1976-07-09 1978-01-24 Toho Rayon Co Ltd Copolymers for use in lenses and their preparation
JPS5515118A (en) * 1978-07-17 1980-02-02 Hoya Corp Improved copolymer for high refractive index lens

Also Published As

Publication number Publication date
JPS5723901A (en) 1982-02-08

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