JPS5872101A - Synthetic resin lens - Google Patents

Synthetic resin lens

Info

Publication number
JPS5872101A
JPS5872101A JP17112081A JP17112081A JPS5872101A JP S5872101 A JPS5872101 A JP S5872101A JP 17112081 A JP17112081 A JP 17112081A JP 17112081 A JP17112081 A JP 17112081A JP S5872101 A JPS5872101 A JP S5872101A
Authority
JP
Japan
Prior art keywords
weight
parts
lens
synthetic resin
lenses
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.)
Granted
Application number
JP17112081A
Other languages
Japanese (ja)
Other versions
JPH0319521B2 (en
Inventor
Takao Mogami
最上 隆夫
Yoshihiko Kasai
河西 嘉彦
Hiroo Sumi
住 宏夫
Hiroichi Deguchi
出口 博一
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.)
Seiko Epson Corp
Suwa Seikosha KK
Original Assignee
Seiko Epson Corp
Suwa Seikosha KK
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 Seiko Epson Corp, Suwa Seikosha KK filed Critical Seiko Epson Corp
Priority to JP17112081A priority Critical patent/JPS5872101A/en
Publication of JPS5872101A publication Critical patent/JPS5872101A/en
Publication of JPH0319521B2 publication Critical patent/JPH0319521B2/ja
Granted legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerization Catalysts (AREA)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 本発明は合成樹脂としては比較的屈折率の高い(屈折率
t57〜t61)、特性の優れた合成樹脂レンズに関す
るものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a synthetic resin lens having a relatively high refractive index (refractive index t57 to t61) for a synthetic resin and excellent characteristics.

1972年の米国のIDム規格の制定以来、眼鏡レンズ
の安全性が見直されるようになっている中で、レンズ材
料としてより安全性の高い合成樹脂が、無機ガラスに代
って使用されるようになってきた。無機ガラスレンズか
ら合成樹脂レンズへの移行は、世界的な傾向であり、我
国においても年々合成樹脂レンズのシェアが拡大しつつ
ある。
Since the enactment of the US IDM standards in 1972, the safety of eyeglass lenses has been reconsidered, and safer synthetic resins are being used as lens materials instead of inorganic glass. It has become. The shift from inorganic glass lenses to synthetic resin lenses is a worldwide trend, and in Japan, the share of synthetic resin lenses is increasing year by year.

特にジエチレングリコールビスアリルカ二ボネート(以
下0R−5?)と略す)樹脂によるレンズの比率は、ア
メリカ、7ランスにおいて既に50−を越えたと予想さ
れる。合成樹脂レンズは安全性が高く、万−割れた場合
にも、無機ガラスのような微細な破片とならず、眼に損
傷を与える可能性が少ない。又、無機ガラスに比較して
軽い、加工性が良い、着色ガ容易である等の多くの利点
を有している。一方、合成樹脂で眼鏡レンズ材料の主流
として広く使用きれている0R−39は、屈折率がtS
Oと低く、又、機械的強度が弱いため、同じ度数を示す
レンズでも無機ガラスレンズに1 比べ、中心厚を厚くしなければならないという環。
In particular, the ratio of lenses made of diethylene glycol bisallyl carbonate (hereinafter abbreviated as 0R-5?) resin is expected to have already exceeded 50 in 7 lenses in the United States. Synthetic resin lenses are highly safe, and even if they break, they do not break into minute pieces like inorganic glass, and are less likely to cause damage to the eyes. In addition, it has many advantages compared to inorganic glass, such as being lighter, easier to process, and easier to color. On the other hand, 0R-39, which is a synthetic resin and is widely used as the mainstream eyeglass lens material, has a refractive index of tS.
Due to its low O and weak mechanical strength, the center thickness must be thicker than that of an inorganic glass lens even if the lens has the same dioptric power.

由のため、特にマイナスレンズにおいては、レンズのコ
バ厚みが著しく厚くなり、薄いレンズへの消費者の潜在
的要求は非常に強い。又、比較的屈折率の高い有機材料
であるぎりスチレン、〆リカーボネート等は、耐擦傷性
、玉摺加工性、耐熱性、耐溶剤性等に問題を有している
For this reason, the edge thickness of the lens becomes significantly thicker, especially in minus lenses, and there is a strong latent demand from consumers for thinner lenses. Furthermore, organic materials with a relatively high refractive index, such as styrene and recarbonate, have problems in scratch resistance, beading processability, heat resistance, solvent resistance, and the like.

本発明は上記の点に鑑み、より屈折率が高く、レンズと
して要求される諸物件を十分満足し、製造上の問題点を
解決した合成樹脂レンズを実現するために成されたもの
である。
In view of the above points, the present invention has been made in order to realize a synthetic resin lens that has a higher refractive index, fully satisfies various properties required for a lens, and solves manufacturing problems.

すなわち本発明の目的は、眼鏡レンズに要求される、無
色でかつ優れた透明性を有し、眼鏡装用者の潜在的要求
であるレンズの厚みを薄くするために約1.6の屈折率
を有し、レンズ加工性の良い合成樹脂レンズを提供する
ことにある。
That is, the object of the present invention is to provide a lens with a refractive index of approximately 1.6, which is required for eyeglass lenses, to be colorless and have excellent transparency, and to reduce the thickness of the lens, which is a potential requirement of eyeglass wearers. The object of the present invention is to provide a synthetic resin lens with a high processability.

又、本発明の別の大きな目的は優れた耐候性、耐熱性、
難燃性を有する有機レンズを合成することにある。
Another major objective of the present invention is to provide excellent weather resistance, heat resistance,
The objective is to synthesize organic lenses with flame retardant properties.

本発明によるレンズ用共重合物は、一般式が、〔工〕で
表わされる1種以上の単量体を9から80重量部と、一
般式が(l[)で示される1種以上の単量体を20から
80重量部と、一般式が(1)で示される重合開始剤を
l11から40重量部と紫外線吸収剤をaolからto
重量部含むモノマーO混合液をラジカル共重合させるこ
とにより得られる。
The copolymer for lenses according to the present invention contains 9 to 80 parts by weight of one or more monomers whose general formula is represented by 20 to 80 parts by weight of polymer, 11 to 40 parts by weight of a polymerization initiator whose general formula is represented by (1), and aul to 40 parts by weight of an ultraviolet absorber.
It can be obtained by radical copolymerization of a mixed solution of monomer O containing parts by weight.

・・・・・・(It) R,−0−0−0−Rs ・・・・・・(II) (式中、Xはフッ素を除く)・ロゲン又は水素、Yはフ
ッ素を除くノ・ロゲン、R1は水素又はメチル基、R1
゜R1は炭素数が1から12のアルキル基、儒は1又は
2、ルは0から3を表わす)本発明を実施するに当って
の物質(1(1)〔I)、紫外線吸収剤の混合比は、特
許請求の範囲で述べた割合により、眼鏡レンズに要求さ
れる特性を満足さ−せることができるがより優れた特性
を持たせるためには、使用される単量体〔I〕〔I〕の
種類によっても異なるが、単量体(1)は30〜65重
量部、単量体(I[)は25〜70重量部、重合開始剤
(N)は15〜20重量部、紫外S吸収剤は(LO5〜
17重量部が好適である。
......(It) R, -0-0-0-Rs ......(II) (In the formula, X excludes fluorine), rogene or hydrogen, Y excludes fluorine, rogen, R1 is hydrogen or methyl group, R1
゜R1 represents an alkyl group having 1 to 12 carbon atoms, 咒 represents 1 or 2, and RU represents 0 to 3) Substances used in carrying out the present invention (1 (1) [I), ultraviolet absorber The mixing ratio can satisfy the properties required for eyeglass lenses according to the proportions stated in the claims, but in order to have better properties, the monomer [I] used should be Although it varies depending on the type of [I], monomer (1) is 30 to 65 parts by weight, monomer (I[) is 25 to 70 parts by weight, polymerization initiator (N) is 15 to 20 parts by weight, The UV S absorber is (LO5~
17 parts by weight is preferred.

単量体CI)の組成比が9重量部未満の場合には、レン
ズの耐衝撃強度が低下し、80重量部を越えると耐熱性
、耐薬品性、耐擦傷性、玉摺加工性が著しく低下する。
If the composition ratio of monomer CI) is less than 9 parts by weight, the impact strength of the lens will decrease, and if it exceeds 80 parts by weight, the heat resistance, chemical resistance, scratch resistance, and chamferability will be significantly reduced. descend.

単量体(II)の組成比が20重量部未満の場合には、
単量体CI)の場合とは逆で、耐熱性、耐薬品性、耐擦
傷性、玉摺加工性が低下し、80重量部を越すと耐衝撃
性が低下し、レンズに要求される特性を満足できない。
When the composition ratio of monomer (II) is less than 20 parts by weight,
Contrary to the case of monomer CI), heat resistance, chemical resistance, abrasion resistance, and abrasive workability decrease, and if it exceeds 80 parts by weight, impact resistance decreases, and the properties required for lenses I can't be satisfied with that.

重合開始剤(II)の組成比が(11重量部未満の場合
には、耐擦優性、耐溶剤性が悪く、40重量部を越すと
もろ<′、又反応の制御が困難となる。
If the composition ratio of the polymerization initiator (II) is less than 11 parts by weight, the abrasion resistance and solvent resistance will be poor, and if it exceeds 40 parts by weight, it will become difficult to control the reaction.

本発明に用いる紫外線吸収剤としては、ベンゾフェノン
系、或はベンゾトリアゾール系、置換アクリロニトリル
系、サリチレー)系の紫外線吸収剤がある。
Examples of the ultraviolet absorbent used in the present invention include benzophenone-based, benzotriazole-based, substituted acrylonitrile-based, and salicylate-based ultraviolet absorbers.

本発明は所定の曲率を有する二枚のガラスモールドとガ
スケッシにより作られた空間に単量体〔1)(夏〕と〔
夏〕で表わされる重合開始剤と紫外II@収剤O混合液
を注入し、加熱硬化することにより成される。重合開始
剤の種類と濃度は単量体〔I〕〔亘〕の混合液の組成、
反応性、反応速度制御等を考慮し決定される。
In the present invention, monomer [1] (summer) and [
This is accomplished by injecting a mixture of a polymerization initiator represented by [Summer] and ultraviolet II @ collector O, and heating and curing. The type and concentration of the polymerization initiator are determined by the composition of the mixture of monomers [I] and [Wataru].
It is determined by considering reactivity, reaction rate control, etc.

本発明による合成樹脂レンズは、アゾビスイソブチロニ
トリルや、シイツブルビルバーオキシジカーボネートで
代表されるパーオキシジカーメネート、ベンゾイルパー
オキシサイド、ラウロイルパーオキシサイドで代表され
るジアシルパーオキサイド、ジ−t−ブチルパーオキサ
イドのようなジアルキルパーオキサイド−1その他のケ
トンパーオキサイド、ハイドロパーオキサイドでは達成
できなかった、無色で優れた透明性を有するレンズを提
供した点に特長がある。
The synthetic resin lens according to the present invention uses azobisisobutyronitrile, peroxydicarmenate represented by sewable bilber oxydicarbonate, diacyl peroxide represented by benzoyl peroxide, and lauroyl peroxide. , dialkyl peroxide-1 such as di-t-butyl peroxide, and other ketone peroxides and hydroperoxides, which are advantageous in that they provide lenses that are colorless and have excellent transparency, which cannot be achieved with other ketone peroxides or hydroperoxides.

更に詳しく述べるなら一般式が(1)で示される重合開
始剤、すなわち、t−ブチルパーオキシイソブチレート
、t−プチルパーオキシビパレート、t−ブチルパーオ
キシネオデカネート、1−ブチルパーオキシラウレート
等のパーオキシエステルを使用することによりレンズの
黄色味を除★したことである。
More specifically, polymerization initiators represented by the general formula (1), namely t-butylperoxyisobutyrate, t-butylperoxybiparate, t-butylperoxyneodecanate, 1-butylperoxy By using peroxyester such as laurate, the yellow tint of the lens was removed.

又上記の方法により得られた合成樹脂レンズは1!io
、等の蒸着によるコーテイング膜との密着性も非常に優
れたものでありコート膜の品質を向上゛させることがで
きた。
Also, the synthetic resin lens obtained by the above method is 1! io
The adhesion with the coating film formed by vapor deposition such as , etc. was also very excellent, and the quality of the coating film could be improved.

以下に本発明の実施例を示すが、本発明の範囲tta定
するものではない。尚実施例中r部」は「重量部」のこ
とである。
Examples of the present invention are shown below, but they do not limit the scope of the present invention. In the examples, "r parts" means "parts by weight."

実施例1 スチレン50重量部、2.2−ビス(3□5−ジブロム
、4−メタクロイルオキシエトキシフェニル)プロパン
4&5重量部 t−プチルパーオキシビパレートt5重
量部 2−(2’−ヒトaキシ−5′メチルフエニル)
ベンゾトリアシー ル(L2重量部を混合攪拌する。次
にこの混合液の不溶物をフィルターで除去し、゛胃液を
軟質ぎり塩化ビニルで成形されたガスケットと二枚のガ
ラスモールドで作られる空間に注入した。次に30℃で
4時間、50℃から50℃まで直線的に10時間、50
℃から70℃まで直線的に2時間、70℃で1時間、8
0℃で2時間熱サイクルをかけた後、ガスケットとガラ
スモールドからレンズを分離した。更に得られたレンズ
を110℃で2時間ゼストキエアし、レンズ内部の歪を
取った。このようにして製造されたレンズは無色で透明
感の優れたものであった。又屈折率1着色、玉摺加工性
Example 1 50 parts by weight of styrene, 4 & 5 parts by weight of 2,2-bis(3□5-dibromo,4-methacroyloxyethoxyphenyl)propane 5 parts by weight of t-butylperoxybiparate t2-(2'-human a) (xy-5'methylphenyl)
Mix and stir 2 parts by weight of benzotriacyl (L). Next, insoluble matter from this mixture is removed with a filter, and the gastric juice is poured into a space made of a gasket made of vinyl chloride and two glass molds. The injection was then carried out at 30°C for 4 hours, then linearly from 50°C to 50°C for 10 hours.
℃ to 70℃ linearly for 2 hours, 70℃ for 1 hour, 8
After thermal cycling at 0° C. for 2 hours, the lens was separated from the gasket and glass mold. Furthermore, the obtained lens was subjected to zesty air treatment at 110° C. for 2 hours to remove distortion inside the lens. The lens thus produced was colorless and had excellent transparency. Also, it has a refractive index of 1 and is colored with a beading process.

硬度、耐衝撃性、耐候性、耐熱性、耐溶剤性、耐熱性を
測定し得られた結果を表−1に示した。更に得られたレ
ンズに二酸化硅素を3μ真空蒸着し、得られたコート膜
の密着性を調査し、表−1に示した。
The hardness, impact resistance, weather resistance, heat resistance, solvent resistance, and heat resistance were measured and the results are shown in Table 1. Furthermore, 3 μm of silicon dioxide was vacuum-deposited on the obtained lens, and the adhesion of the obtained coating film was investigated, and the results are shown in Table 1.

なお、それぞれの特性についての試験方法は、下記の通
り行った。
In addition, the test method for each characteristic was performed as follows.

屈折率:アツベ屈折計により測定した 着色:目視で無色透明なものを良とした1摺加工性:レ
ンズ加工用のダイアモンドエツジヤ−で研削し、研削可
能で面のき れいなものを良とした 鉛筆硬度!71B([5400)により行りた耐衝撃性
2中心厚2m1mの平板に シフム規格に従って鋼球落
下試験を行い、割れな いものを良とした 耐候性:ウェザ−メーター2004間試験後面の荒れ、
着色(黄変)のないものを 良とした 耐熱性=120℃で3時間加熱し、着色、度数変化、変
形のないものを良とした 耐溶剤性:エチルアルコール、ア七トンに20℃で一昼
夜浸漬し、溶出、面の荒れ 、曇り、変形のないものを良とした コー)膜密着性:二酸化硅素を3μ真空蒸着したレンズ
を70℃の温水に2時間浸 いものを良とした 実施例−2 0一クロルスチレン60重量m a 2 # 2−ビス
(S 、 5−ジブロム−4−メタクロイルオキシェ)
キシ7エエル)プロパン!asffi量s  t −フ
チルバーオキシネオデカネート10重量部 2−ヒドロ
キシ4−メトキシベンゾフェノン(L5重量部の混合波
を実施例1と同様にレンズを製造し、その特性を調査し
た。レンズとしての特性を十分満足できるものであり、
結果を表−1に示した。
Refractive index: Measured using an Atsube refractometer Coloration: Colorless and transparent pencils are considered good by visual inspection Workability: Pencils that can be ground with a diamond edger for lens processing and have a clean surface are considered good hardness! 71B ([5400)] A steel ball drop test was performed on a flat plate with a center thickness of 2m1m according to the Schiffm standard, and those that did not break were considered good.Weather resistance: Roughness of the surface after the Weathermeter 2004 test.
Heat resistance: No coloring (yellowing) is considered good. Heat resistance is good when heated at 120°C for 3 hours, and no coloring, change in frequency, or deformation is considered good. Solvent resistance: Ethyl alcohol, A7T at 20°C. Film adhesion: Lenses vacuum-deposited with 3 μm of silicon dioxide were immersed in hot water at 70°C for 2 hours, and those with no elution, surface roughness, clouding, or deformation were considered good. Example-2 0-1 chlorstyrene 60 weight m a 2 #2-bis(S, 5-dibrom-4-methacroyloxie)
Kis7el) Propane! Amount of asffi 10 parts by weight of t-phthyl baroxyneodecanate 5 parts by weight of 2-hydroxy 4-methoxybenzophenone (L) A lens was manufactured in the same manner as in Example 1, and its properties were investigated. Characteristics as a lens It is enough to satisfy
The results are shown in Table-1.

比較例も表−1に示した。Comparative examples are also shown in Table-1.

表−1における組成の略語は下記の通りであるSt:ス
チレン Br4BMII!PP  : 2 、2−ビス(S 、
’5−ジブロムー4メタクロイルオキシエトキシフェニ
ル)プロパン 13PV:t−プチルパーオ牟シビパレートHMIP、
111?’II T 2−(2’−ヒドロキシー5′−
メチルフェニル)ベンゾトリアゾール o−ozst:オルトクロルスチレン npyn:t、−ブチルパーオキシネオデカネートHM
B?!2−ヒドロキシ−4−メトキシベンゾフェノン 11POSペンゾイルパーオキサイド エPP1ジイソプロビルパーオキシジ力−lネーシ 表−1レンズ試験結果
The abbreviations of the compositions in Table 1 are as follows: St: Styrene Br4BMII! PP: 2,2-bis(S,
'5-dibromo-4-methacryloyloxyethoxyphenyl)propane 13PV: t-butylperomucibiparate HMIP,
111? 'II T 2-(2'-hydroxy-5'-
methylphenyl)benzotriazole o-ozst: orthochlorostyrene npyn: t,-butylperoxyneodecanate HM
B? ! 2-Hydroxy-4-methoxybenzophenone 11POS Penzoyl peroxide PP1 Diisoprobyl peroxide Table 1 Lens test results

Claims (1)

【特許請求の範囲】 一般式が〔!〕で表わされる1種以上の単量体を?から
80重量部と、一般式が(][)で示される1種以上の
単量体を20から8゛0重量部と、−0重量部と、紫外
線吸収剤を(Lotからto重量部含むモノ!−の混合
液をラジカル典型合さ?たことを特徴とする合成樹脂製
レンズ。。 −−−−(I ) R,−0−0−a−1,−CM ) (式中Xはフッ素を除くハロゲン又は水素、Yはフッ素
を除くハロゲン、Rは水素又はメチル基、”m  e 
Raは炭素数が1から12C)アルキル基、憾は1又は
2、露は0から3を表わす)
[Claims] The general formula is [! ] One or more monomers represented by ? to 80 parts by weight, 20 to 80 parts by weight of one or more monomers having the general formula (][), -0 parts by weight of an ultraviolet absorber (from Lot to to parts by weight) A synthetic resin lens characterized by a radical combination of a mixture of mono!-.---(I)R,-0-0-a-1,-CM) halogen or hydrogen excluding fluorine, Y is halogen excluding fluorine, R is hydrogen or methyl group, "me
Ra is an alkyl group having 1 to 12 carbon atoms;
JP17112081A 1981-10-26 1981-10-26 Synthetic resin lens Granted JPS5872101A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP17112081A JPS5872101A (en) 1981-10-26 1981-10-26 Synthetic resin lens

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP17112081A JPS5872101A (en) 1981-10-26 1981-10-26 Synthetic resin lens

Publications (2)

Publication Number Publication Date
JPS5872101A true JPS5872101A (en) 1983-04-30
JPH0319521B2 JPH0319521B2 (en) 1991-03-15

Family

ID=15917345

Family Applications (1)

Application Number Title Priority Date Filing Date
JP17112081A Granted JPS5872101A (en) 1981-10-26 1981-10-26 Synthetic resin lens

Country Status (1)

Country Link
JP (1) JPS5872101A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58171408A (en) * 1982-04-02 1983-10-08 Tokuyama Soda Co Ltd Manufacturing method of high refractive index transparent resin
US5384380A (en) * 1993-01-14 1995-01-24 Daiso Co., Ltd. Polymerizable compositions and high refractive plastic lens obtained therefrom

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56166214A (en) * 1980-05-27 1981-12-21 Tokuyama Soda Co Ltd Production of resin with high refractive index and high flame retardancy

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56166214A (en) * 1980-05-27 1981-12-21 Tokuyama Soda Co Ltd Production of resin with high refractive index and high flame retardancy

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58171408A (en) * 1982-04-02 1983-10-08 Tokuyama Soda Co Ltd Manufacturing method of high refractive index transparent resin
US5384380A (en) * 1993-01-14 1995-01-24 Daiso Co., Ltd. Polymerizable compositions and high refractive plastic lens obtained therefrom

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