JPS62283109A - Resin having high refractive index - Google Patents
Resin having high refractive indexInfo
- Publication number
- JPS62283109A JPS62283109A JP12566686A JP12566686A JPS62283109A JP S62283109 A JPS62283109 A JP S62283109A JP 12566686 A JP12566686 A JP 12566686A JP 12566686 A JP12566686 A JP 12566686A JP S62283109 A JPS62283109 A JP S62283109A
- Authority
- JP
- Japan
- Prior art keywords
- refractive index
- resin
- high refractive
- monomer
- polymerization
- 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
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 14
- 239000011347 resin Substances 0.000 title claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 4
- 229920001519 homopolymer Polymers 0.000 claims abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 4
- 229920003023 plastic Polymers 0.000 abstract description 4
- 230000004075 alteration Effects 0.000 abstract description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 3
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- IJSVVICYGLOZHA-UHFFFAOYSA-N 2-methyl-n-phenylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=CC=C1 IJSVVICYGLOZHA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 1
- -1 di[-butyl peroxide Chemical compound 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CVUNPKSKGHPMSY-UHFFFAOYSA-N ethyl 2-chloroprop-2-enoate Chemical compound CCOC(=O)C(Cl)=C CVUNPKSKGHPMSY-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CEBFLGHPYLIZSC-UHFFFAOYSA-N n-benzyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCC1=CC=CC=C1 CEBFLGHPYLIZSC-UHFFFAOYSA-N 0.000 description 1
- OHLHOLGYGRKZMU-UHFFFAOYSA-N n-benzylprop-2-enamide Chemical compound C=CC(=O)NCC1=CC=CC=C1 OHLHOLGYGRKZMU-UHFFFAOYSA-N 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
ｌ産業上の利用分野ン
不発明は、高屈折率で収差が小さい透明性の優ねた樹脂
：て関する。無機光学レンズ：（代る素材として透明性
合成樹脂よりなる高屈折率レンズ用樹脂は、その軽量性
や耐衝撃性、成形加工性、染色性が良好なことからプラ
スチックレンズ材料として適用分野を拡大しつつある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a resin having a high refractive index, small aberrations, and excellent transparency. Inorganic optical lenses: (As an alternative material, high refractive index lens resins made of transparent synthetic resins are being used in expanding fields of application as plastic lens materials due to their light weight, impact resistance, moldability, and dyeability. It is being done.
〈従来の技術〉
従来用いられているプラスチックレンズ材料としてはジ
エチレングリコールビスアリルカーボネート樹脂（以下
、ＣＲ−３９という）があるが、これは屈折率が１．４
９〜１．５０と低いため、これから得られる樹脂を眼鏡
用レンズにすると無機光学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。<Prior art> A conventionally used plastic lens material is diethylene glycol bisallyl carbonate resin (hereinafter referred to as CR-39), which has a refractive index of 1.4.
9 to 1.50, so if the resin obtained from this resin is used as an eyeglass lens, there is a drawback that the lens will be thicker than an inorganic optical lens.
く本発明が解決しようとする問題点〉
高屈折率樹脂として代表的なものにポリカーボネート（
屈折率ｒｌｌ）＝１．５９、アツベ数ν＝３０）がある
が耐擦傷性や研磨性が劣ることやアツベ数が比較的小さ
く色収差が大きい・という欠へかある。Problems to be Solved by the Present Invention> Polycarbonate is a typical high refractive index resin.
It has a refractive index rll) = 1.59 and an Abbe number ν = 30), but it has drawbacks such as poor scratch resistance and polishing properties, a relatively small Abbe number, and large chromatic aberration.
〈問題点を解決するだめの手段および作用〉本発明者ら
は上記の問題点を解決すべく鋭意研究を重ねだ結果、
一般式（１）
Ｒ
（但し、ＲはＨ，Ｃ１もしくはＣＨ３基、ｎはＯ〜４の
整数）
で示される単量体を単独重合させる、又は、前記単量体
と他のビニル単量体とを共重合させることにより光学的
に屈折率が高く、かつ低分散の樹脂が得られることを見
い出した。すなわち本発明は、プラスチックレンズ用樹
脂として高屈折率で低分散の樹脂を提供することを目的
とするものである。<Means and effects for solving the problems> The present inventors have conducted intensive research to solve the above problems, and as a result, the general formula (1) R (where R is H, C1 or CH3 group, n is an integer of 0 to 4) By homopolymerizing a monomer represented by the formula (n is an integer of 0 to 4), or copolymerizing the monomer with another vinyl monomer, an optically high refractive index and low dispersion can be obtained. It was discovered that a resin of That is, an object of the present invention is to provide a resin with a high refractive index and low dispersion as a resin for plastic lenses.
本発明においては、前記一般式（１）で示される単量体
の単独重合物を光学用グラスチックレンズ用樹脂として
用いることができるが、ＣＲ−３９またはアクリル酸や
メタクリル酸のエステル類やアミド類、たとえばフェニ
ルメタクリレート、ベンジルメタクリレート、ベンジル
アクリレートやＮ−フェニルメタクリルアミド、Ｎ−ベ
ンジルメタクリルアミド、Ｎ−ベンジルアクリルアミド
やさらにスチレン、クロルスチレン等との共重合も可能
である。これらの単量体は前記一般式（１１で示される
単量体と均一に混ざり合い、共重合可能であること、又
、その重合性も同程度であり、且つ透明性を損わないこ
となどの点を考慮し適宜選択される。In the present invention, a homopolymer of the monomer represented by the general formula (1) can be used as a resin for optical glass lenses, but CR-39 or esters or amides of acrylic acid or methacrylic acid It is also possible to copolymerize with phenyl methacrylate, benzyl methacrylate, benzyl acrylate, N-phenylmethacrylamide, N-benzylmethacrylamide, N-benzylacrylamide, and also with styrene, chlorostyrene, and the like. These monomers must be uniformly mixed and copolymerizable with the monomer represented by the general formula (11), have the same degree of polymerizability, and do not impair transparency. It is selected appropriately taking into account the following points.
本発明の前記一般式（１１で示される単量体の単独重合
体または他のビニル単量体との共重合体の製法は特に限
定されず公知の方法が使用できる。たとえば、一般に好
適に使用される代表的なラジカル重合開始剤の存在下で
重合する方法を挙げることができる。ラジカル重合開始
剤としては、ベンゾイルパーオキサイド、アセチルパー
オキサイド、ジー【−ブチルパーオキサイド、ジイソプ
ロピルパーオキシカーボネート等の過酸化物やアゾビス
インブチロニトリルなどのアゾ系化合物を挙げることが
できる。The method for producing the homopolymer of the monomer represented by the general formula (11) or the copolymer with other vinyl monomers of the present invention is not particularly limited, and known methods can be used. Examples of radical polymerization initiators include benzoyl peroxide, acetyl peroxide, di[-butyl peroxide, diisopropyl peroxy carbonate, etc.]. Examples include peroxides and azo compounds such as azobisin butyronitrile.
以下に本発明を実施例により具体的に説明する。The present invention will be specifically explained below using examples.
実施例１
２−（トリシクロＣ５１２，１，Ｏ”６〕−３−デセル
チオ）エチルメタクリレート （以下Ａと略記する）１
００重量部に重合開始剤としてアゾビスイソブチロニト
リル０．２重量部を添加しよく混合したものを透明ガラ
ス板とガスケットからなる鋳型の中へ注入し、注型重合
を行った。重合は６０℃で６時間、１１０’Ｃで１時間
加熱して完結させた。このようにして得られた重合体は
無色透明であり、屈折率（Ｎｏ ）は１．５５７、アツ
ベ数（ν）は４７４であった。Example 1 2-(TricycloC512,1,O”6]-3-decelthio)ethyl methacrylate (hereinafter abbreviated as A) 1
0.2 parts by weight of azobisisobutyronitrile as a polymerization initiator was added to 0.00 parts by weight, and the mixture was thoroughly mixed and poured into a mold consisting of a transparent glass plate and a gasket to carry out cast polymerization. Polymerization was completed by heating at 60°C for 6 hours and at 110'C for 1 hour. The polymer thus obtained was colorless and transparent, had a refractive index (No) of 1.557, and an Abbe number (v) of 474.
実施例２
Ａ ５０重量部、ベンジルメタクリレート５０重量部
、アゾビスインブチロニトリル０．２重量部を用い実施
例１と同様に重合した。得られた重合体は無色透明であ
り、屈折率（ＮＤ ）は１，５６３、アツベ数（ν）は
４１．２であった。Example 2 Polymerization was carried out in the same manner as in Example 1 using 50 parts by weight of A, 50 parts by weight of benzyl methacrylate, and 0.2 parts by weight of azobisin butyronitrile. The obtained polymer was colorless and transparent, had a refractive index (ND) of 1,563, and an Abbe number (ν) of 41.2.
実施例３
２−（トリシクロ（５，２，１，０２″６〕−３−デセ
ルチオ）エチル−２−クロロアクリレート５０重量部、
ベンジルメタクリレート５０重量部、アゾビスイ・）
ンプチロニトリル０．２重量部を用い実施例１と同様に
重合した。得られた重合体は無色透明であり、屈折率（
Ｎｏ）は１．５６８、アツベ数（ν）は４２３であった
。Example 3 50 parts by weight of 2-(tricyclo(5,2,1,02″6)-3-decelthio)ethyl-2-chloroacrylate,
Polymerization was carried out in the same manner as in Example 1 using 50 parts by weight of benzyl methacrylate and 0.2 parts by weight of azobisylbutyronitrile. The obtained polymer is colorless and transparent, and has a refractive index (
No.) was 1.568, and Atsube's number (ν) was 423.
Claims (1)
の整数。） で示される単量体よりえられる単独重合体、又は前記単
量体と他のビニル単量体とを共重合してえられる共重合
体から成ることを特徴とする高屈折率樹脂。[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (However, R is H, Cl or CH_3 group, n is 0 to 4
an integer of ) A high refractive index resin comprising a homopolymer obtained from the monomers shown in (1) or a copolymer obtained by copolymerizing the monomers and other vinyl monomers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12566686A JPS62283109A (en) | 1986-06-02 | 1986-06-02 | Resin having high refractive index |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12566686A JPS62283109A (en) | 1986-06-02 | 1986-06-02 | Resin having high refractive index |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62283109A true JPS62283109A (en) | 1987-12-09 |
Family
ID=14915652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12566686A Pending JPS62283109A (en) | 1986-06-02 | 1986-06-02 | Resin having high refractive index |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62283109A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01163701A (en) * | 1987-12-21 | 1989-06-28 | Kureha Chem Ind Co Ltd | Plastic lens material |
| JPH01163702A (en) * | 1987-12-21 | 1989-06-28 | Kureha Chem Ind Co Ltd | Plastic lens material |
| WO1990004587A1 (en) * | 1988-10-20 | 1990-05-03 | Showa Denko Kabushiki Kaisha | 4,4'-bis(methacryloylthio)diphenyl sulfide and curable composition containing same |
| US5270439A (en) * | 1988-10-20 | 1993-12-14 | Sumitomo Seika Chemicals Co., Ltd. | Method of producing a curable composition containing 4,4'-bis(methacryloylthio)diphenylsulfide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5125746A (en) * | 1974-08-27 | 1976-03-02 | Sanyo Electric Co |
-
1986
- 1986-06-02 JP JP12566686A patent/JPS62283109A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5125746A (en) * | 1974-08-27 | 1976-03-02 | Sanyo Electric Co |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01163701A (en) * | 1987-12-21 | 1989-06-28 | Kureha Chem Ind Co Ltd | Plastic lens material |
| JPH01163702A (en) * | 1987-12-21 | 1989-06-28 | Kureha Chem Ind Co Ltd | Plastic lens material |
| JPH054642B2 (en) * | 1987-12-21 | 1993-01-20 | Kureha Chemical Ind Co Ltd | |
| JPH054641B2 (en) * | 1987-12-21 | 1993-01-20 | Kureha Chemical Ind Co Ltd | |
| WO1990004587A1 (en) * | 1988-10-20 | 1990-05-03 | Showa Denko Kabushiki Kaisha | 4,4'-bis(methacryloylthio)diphenyl sulfide and curable composition containing same |
| US5183917A (en) * | 1988-10-20 | 1993-02-02 | Showa Denko K.K. | 4,4'-bis(methacryloylthio)diphenylsulfide |
| US5270439A (en) * | 1988-10-20 | 1993-12-14 | Sumitomo Seika Chemicals Co., Ltd. | Method of producing a curable composition containing 4,4'-bis(methacryloylthio)diphenylsulfide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2537540B2 (en) | Monomer composition | |
| US4578445A (en) | Halogen-containing lens material | |
| US4522993A (en) | Resin for high-refractivity lenses and lenses made of same resin | |
| EP0142118A2 (en) | Monomeric mixture of cured polymeric material used in organic glass | |
| JP2003137938A (en) | Curable composition having excellent optical characteristic | |
| JPS6323908A (en) | Plastic lens material | |
| JPS62283109A (en) | Resin having high refractive index | |
| JPS61287913A (en) | Resin for optical material | |
| EP0154136A1 (en) | Plastic lens and method of manufacturing thereof | |
| JPS6225162B2 (en) | ||
| JPS61159408A (en) | Production of polymer | |
| JP2966236B2 (en) | Optical element | |
| JP4678008B2 (en) | Curable composition for plastic lens | |
| JPS60124605A (en) | Optical material | |
| JPH0251161B2 (en) | ||
| JPH02265907A (en) | High-refractive index optical resin | |
| JPH04225007A (en) | Optical resin having high refractive index and high strength | |
| JPS61247715A (en) | Resin for plastic lens | |
| JP3284213B2 (en) | Thermoplastic resin and optical parts made of it | |
| JPS63268707A (en) | Resin having high refractive index | |
| JPS63251408A (en) | Resin of high refractive index | |
| JPH0679083B2 (en) | Optical material | |
| JPH07145106A (en) | Acrylic acid derivative | |
| JPS6220514A (en) | Novel copolymer | |
| JPH01207307A (en) | Production of resin with high refractive index |