JPH0456281B2 - - Google Patents
Info
- Publication number
- JPH0456281B2 JPH0456281B2 JP57117235A JP11723582A JPH0456281B2 JP H0456281 B2 JPH0456281 B2 JP H0456281B2 JP 57117235 A JP57117235 A JP 57117235A JP 11723582 A JP11723582 A JP 11723582A JP H0456281 B2 JPH0456281 B2 JP H0456281B2
- Authority
- JP
- Japan
- Prior art keywords
- refractive index
- lens
- polymerization
- lenses
- 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
Links
- 229920003002 synthetic resin Polymers 0.000 claims description 10
- 239000000057 synthetic resin Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000004075 alteration Effects 0.000 description 3
- -1 for example Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- KCMITHMNVLRGJU-CMDGGOBGSA-N Allyl cinnamate Chemical compound C=CCOC(=O)\C=C\C1=CC=CC=C1 KCMITHMNVLRGJU-CMDGGOBGSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- HVYCQBKSRWZZGX-UHFFFAOYSA-N naphthalen-1-yl 2-methylprop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C(=C)C)=CC=CC2=C1 HVYCQBKSRWZZGX-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- CLIGMUNFUITOMS-UHFFFAOYSA-N (1,2,2-tribromo-2-phenoxyethyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(Br)C(Br)(Br)OC1=CC=CC=C1 CLIGMUNFUITOMS-UHFFFAOYSA-N 0.000 description 1
- HAYWJKBZHDIUPU-UHFFFAOYSA-N (2,4,6-tribromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=C(Br)C=C(Br)C=C1Br HAYWJKBZHDIUPU-UHFFFAOYSA-N 0.000 description 1
- CNLVUQQHXLTOTC-UHFFFAOYSA-N (2,4,6-tribromophenyl) prop-2-enoate Chemical compound BrC1=CC(Br)=C(OC(=O)C=C)C(Br)=C1 CNLVUQQHXLTOTC-UHFFFAOYSA-N 0.000 description 1
- DGZZQOZXBPFEIY-UHFFFAOYSA-N (2,4,6-trichlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=C(Cl)C=C(Cl)C=C1Cl DGZZQOZXBPFEIY-UHFFFAOYSA-N 0.000 description 1
- PKJZBAPPPMTNFR-UHFFFAOYSA-N (2,4,6-trichlorophenyl) prop-2-enoate Chemical compound ClC1=CC(Cl)=C(OC(=O)C=C)C(Cl)=C1 PKJZBAPPPMTNFR-UHFFFAOYSA-N 0.000 description 1
- GOUZWCLULXUQSR-UHFFFAOYSA-N (2-chlorophenyl) prop-2-enoate Chemical compound ClC1=CC=CC=C1OC(=O)C=C GOUZWCLULXUQSR-UHFFFAOYSA-N 0.000 description 1
- SIADNYSYTSORRE-UHFFFAOYSA-N (4-chlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(Cl)C=C1 SIADNYSYTSORRE-UHFFFAOYSA-N 0.000 description 1
- IGHDIBHFCIOXGK-UHFFFAOYSA-N (4-chlorophenyl) prop-2-enoate Chemical compound ClC1=CC=C(OC(=O)C=C)C=C1 IGHDIBHFCIOXGK-UHFFFAOYSA-N 0.000 description 1
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- IUNUDCDZCMNUGD-UHFFFAOYSA-N 2-(2-propylphenoxy)ethyl 2-methylprop-2-enoate Chemical compound CCCC1=CC=CC=C1OCCOC(=O)C(C)=C IUNUDCDZCMNUGD-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
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- ORNUPNRNNSVZTC-UHFFFAOYSA-N 2-vinylthiophene Chemical compound C=CC1=CC=CS1 ORNUPNRNNSVZTC-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- CHGZDPJVYBVPEU-UHFFFAOYSA-N 4-[3-(2-methoxy-4-methylphenyl)propyl]benzene-1,3-diol Chemical compound COC1=CC(C)=CC=C1CCCC1=CC=C(O)C=C1O CHGZDPJVYBVPEU-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GMPDOIGGGXSAPL-UHFFFAOYSA-N Phenyl vinyl sulfide Chemical compound C=CSC1=CC=CC=C1 GMPDOIGGGXSAPL-UHFFFAOYSA-N 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- FKRRNHGDZIXAEC-UHFFFAOYSA-N [2,6-dibromo-4-[2-[3,5-dibromo-4-(2-methylprop-2-enoyloxy)phenyl]propan-2-yl]phenyl] 2-methylprop-2-enoate Chemical compound C1=C(Br)C(OC(=O)C(=C)C)=C(Br)C=C1C(C)(C)C1=CC(Br)=C(OC(=O)C(C)=C)C(Br)=C1 FKRRNHGDZIXAEC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 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
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-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
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000005331 crown glasses (windows) Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 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
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 239000000843 powder 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
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical 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)
Description
本発明は、色収差の少ない高屈折率合成樹脂レ
ンズに関するものである。従来、眼鏡用レンズと
しては、無機ガラスが使用されていたが、近年、
合成樹脂、例えば、ジエチレングリコールビスア
リルカーボネート（以下CR39と略す）の重合体
が利用されるようになつてきた。合成樹脂レンズ
は、無機ガラスレンズに較べて、軽量性、染色
性、耐衝撃性（安全性）等においてすぐれてい
る。しかし、CR39重合体の屈折率は、1.50であ
り、一般の無機ガラス（クラウンガラス）の屈折
率1.523に較べて低い。その為、レンズの肉厚や
コバ厚が大きくなるという欠点を有している。最
近、特開昭54−77686、特開昭56−166214、特開
昭57−54901等に見られるように高屈折率を有す
る合成樹脂レンズが種種提案されている。これら
の合成樹脂レンズは、高屈折率を有するため、従
来のCR39重合体よりレンズの肉厚やコバ厚を薄
くできるという特徴を持つている。しかし、屈折
率を高めた反面、アツベ数が30と著しく低くなつ
ている。その為、レンズの色収差が増大し、実用
上眼鏡レンズとして使用できる度数範囲がきわめ
て限定されてしまうという欠点を有していた。
一般にアツベ数νは次式で与えられ、眼鏡レン
ズとしては少なくとも35以上が必要であり、40以
上を有る材料が特に好ましい。
ν＝nD−１／nF−nC
（nD：ナトリウムＤ線による屈折率
nF：水素Ｆ線による屈折率
nC：水素Ｃ線による屈折率）
本発明の目的は、高屈折率かつ高アツベ数を有
する合成樹脂レンズを供給することにある。本発
明の他の目的は、眼鏡レンズに要求されるすぐれ
た透明性、加工性、耐光性等を満足する合成樹脂
レンズを提供することにある。
本発明の目的は、一般式
（Ｘ：Ｈ又はCH3、ｎ：０、１又は２）
で表わされる１種以上の第１単量体と、単独重合
体の屈折率が1.55以上で、芳香族、ハロゲン原
子、イオウ原子のいずれかを有するラジカル重合
可能な１種以上の第２単量体とを共重合すること
により得られる。第２単量体としては、スチレ
ン、α−メチルスチレン、ｐ−メチルスチレン、
ｐ−メトキシスチレン、アリルシンナメート、フ
エニルアクリレート、フエニルメタクリレート、
ベンジルアクリレート、ベンジルメタクリレー
ト、α−ナフチルアクリレート、α−ナフチルメ
タクリレート、１−ビニルナフタレン、２−ビニ
ルナフタレン、Ｎ−ビニルカルバゾール、ビスフ
エノールＡジメタクリレート、２，２−ビス（４
−メタクリロイルオキシエトキシフエニル）プロ
パン、ジアリルフタレート、ジアリルイソフタレ
ート、トリアリルシアヌレート、トリアリルイソ
シアヌレート等の芳香環を有する単量体、クロル
スチレン、ジクロルスチレン、Ｏ−クロルフエニ
ルメタクリレート、ｐ−クロルフエニルメタクリ
レート、ｏ−クロルフエニルアクリレート、ｐ−
クロルフエニルアクリレート、２，４，６−トリ
クロルフエニルアクリレート、２，４，６−トリ
クロルフエニルメタクリレート、２，４，６−ト
リブロムフエニルアクリレート、２，４，６−ト
リブロムフエニルメタクリレート、ｐ−ブロムフ
エニルオキシエチルメタクリレート、２，４，６
−トリブロムフエニルオキシエチルメタクリレー
ト、テトラクロロビスフエノールＡジメタクリレ
ート、テトラブロムビスフエノールＡジメタクリ
レート、２，２−ビス（４−メタクリロイルオキ
シエトキシ３，３−ジブロムフエニル）プロパン
等のハロゲン原子を含有する単量体、ビニルチオ
フエン、ビニルフエニルサルフアイド等のイオウ
原子を有する単量体を用いることができる。
第１単量体の好適使用量は、30〜90重量％の範
囲であり、第２単量体の好適使用量は、10〜70重
量％の範囲である。
本発明にかかる合成樹脂レンズは、前記単量体
と重合開始剤との混合液を、ガラスモールドと樹
脂製ガスケツトとを組み合せた鋳型中に注入した
のち、加熱することにより得られる。また、かか
る方法によらず、紫外線重合、放射線重合、プラ
ズマ重合によつてもキヤスト可能であり、更には
溶液重合法や懸濁重合法によつて製造した重合体
粉末あるいは粒子を圧縮成形、トランスフアー成
形、射出成形等によりレンズを得ることも可能で
ある。尚、本発明にかかるレンズを製作するに際
しては、必要に応じて、紫外線吸収剤、酸化防止
剤、帯電防止剤、染料等を添加してよいことはも
ちろんである。
本発明にかかるレンズの重合条件は、単量体の
種類、重合開始剤の種類により異なるため、一義
的には決められないが、一般には重合温度は30°
〜90℃の範囲が用いられ、重合時間は、６〜72時
間の範囲が用いられる。利用できる重合開始剤と
しては、アゾビスイソブチロニトリル、ベンゾイ
ルパーオキサイド、ジイソプロピルパーオキシジ
カーボネート等の通常使用されている開始剤を用
いることができる。
かくして得られる本発明の合成樹脂レンズは、
高い屈折率と大きなアツベ数を同時に有し、従来
提示されていた高屈折率レンズでは満たすことの
できなかつたレンズ性能を具備している。さらに
透明性、耐光性、加工性等においても眼鏡レンズ
としての実用性を満足しているものも本発明の特
徴の一つである。
次に、本発明をより良く説明する為に、実施例
を記載する。
実施例 １
ジシクロペンテニルアクリレート70部、α−ナ
フチルメタクリレート30部、過酸化ベンゾイル
0.2部、２−ヒドロキシ−４−ｎ−オクトキシベ
ンゾフエノン0.1部から成る混合液を、２枚のガ
ラスモールドと塩化ビニルガスケツトから成る鋳
型中の注入したのち、60℃に10時間、80℃に６時
間保持した。重合終了後、鋳型からレンズを取外
し、100℃で１時間アニーリングした。得られた
レンズは透明率90％、屈折率1.573、アツベ数40
というすぐれた光学物性を有していた。また玉摺
機による加工性、ウエザーメータによる耐光性に
もすぐれていた。更に、真空蒸着法による反射防
止膜を施すことも容易であり、レンズの透過率は
97％にまで向上し、きわめて見やすい眼鏡レンズ
を得ることができた。
実施例 ２〜18
実施例１と同様の方法で注型重合したレンズの
光学物性を表１に示した。これらのレンズは、い
ずれも反射防止膜を施すことが可能であつた。
比較例 １
スチレン60部、２，２−ビス（４−メタクリロ
イルオキシ−３，５−ジブロムフエニル）プロパ
ン30部、アリルシンナメート10部、ジイソプロピ
ルパーオキシカーボネート0.2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製ガス
ケツトから成る鋳型中に注入したのち、40℃から
80℃まで24時間かけて昇温した。重合終了後、鋳
型からレンズを取り外し、120℃で１時間アニー
リングした。得られたレンズは、透過率90％、屈
折率90％、屈折率1.592、アツベ数30であり、眼
鏡レンズとして使用すると著しい色収差を生じ、
非常に見づらいものであつた。
The present invention relates to a high refractive index synthetic resin lens with little chromatic aberration. Traditionally, inorganic glass has been used for eyeglass lenses, but in recent years,
Synthetic resins, for example, polymers of diethylene glycol bisallyl carbonate (hereinafter abbreviated as CR39) have come into use. Synthetic resin lenses are superior in lightness, dyeability, impact resistance (safety), etc., compared to inorganic glass lenses. However, the refractive index of CR39 polymer is 1.50, which is lower than the refractive index of general inorganic glass (crown glass), which is 1.523. Therefore, it has the disadvantage that the lens thickness and edge thickness become large. Recently, various synthetic resin lenses having a high refractive index have been proposed, as seen in JP-A-54-77686, JP-A-56-166214, and JP-A-57-54901. These synthetic resin lenses have a high refractive index, so they have the characteristic that the lens wall and edge thickness can be made thinner than conventional CR39 polymers. However, while the refractive index was increased, the Atsbe number was significantly lower at 30. Therefore, the chromatic aberration of the lens increases, and the range of power that can be practically used as an eyeglass lens is extremely limited. In general, the Atsube number ν is given by the following formula, and a spectacle lens must have at least 35, and materials having a value of 40 or more are particularly preferred. ν=n D -1/n F -n C (n D : refractive index by sodium D line n F : refractive index by hydrogen F line n C : refractive index by hydrogen C line) Another object of the present invention is to provide a synthetic resin lens having a high Abe number. Another object of the present invention is to provide a synthetic resin lens that satisfies the excellent transparency, workability, light resistance, etc. required for eyeglass lenses. The purpose of the present invention is to obtain the general formula (X: H or CH 3 , n: 0, 1 or 2), and the homopolymer has a refractive index of 1.55 or more, and contains aromatic, halogen, or sulfur atoms. It can be obtained by copolymerizing one or more radically polymerizable second monomers. As the second monomer, styrene, α-methylstyrene, p-methylstyrene,
p-methoxystyrene, allyl cinnamate, phenyl acrylate, phenyl methacrylate,
Benzyl acrylate, benzyl methacrylate, α-naphthyl acrylate, α-naphthyl methacrylate, 1-vinylnaphthalene, 2-vinylnaphthalene, N-vinylcarbazole, bisphenol A dimethacrylate, 2,2-bis(4
- Monomers having an aromatic ring such as (methacryloyloxyethoxyphenyl) propane, diallyl phthalate, diallyl isophthalate, triallyl cyanurate, triallyl isocyanurate, chlorstyrene, dichlorostyrene, O-chlorophenyl methacrylate, p -Chlorphenyl methacrylate, o-chlorophenyl acrylate, p-
Chlorphenyl acrylate, 2,4,6-trichlorophenyl acrylate, 2,4,6-trichlorophenyl methacrylate, 2,4,6-tribromphenyl acrylate, 2,4,6-tribromphenyl methacrylate , p-bromphenyloxyethyl methacrylate, 2,4,6
- Contains halogen atoms such as tribromophenyloxyethyl methacrylate, tetrachlorobisphenol A dimethacrylate, tetrabromobisphenol A dimethacrylate, 2,2-bis(4-methacryloyloxyethoxy3,3-dibromophenyl)propane, etc. A monomer having a sulfur atom such as vinylthiophene or vinylphenyl sulfide can be used. The preferred amount of the first monomer used is in the range of 30 to 90% by weight, and the preferred amount of the second monomer to be used is in the range of 10 to 70% by weight. The synthetic resin lens according to the present invention can be obtained by injecting a mixture of the monomer and a polymerization initiator into a mold made of a combination of a glass mold and a resin gasket, and then heating the mixture. In addition, casting is possible by ultraviolet polymerization, radiation polymerization, or plasma polymerization, and it is also possible to cast by compression molding or transfer polymer powder or particles produced by solution polymerization or suspension polymerization. It is also possible to obtain lenses by arc molding, injection molding, etc. It goes without saying that when manufacturing the lens according to the present invention, ultraviolet absorbers, antioxidants, antistatic agents, dyes, etc. may be added as necessary. The polymerization conditions for the lens according to the present invention vary depending on the type of monomer and the type of polymerization initiator, so they cannot be determined unambiguously, but generally the polymerization temperature is 30°
~90°C is used, and the polymerization time is used in a range of 6 to 72 hours. As the polymerization initiator that can be used, commonly used initiators such as azobisisobutyronitrile, benzoyl peroxide, and diisopropyl peroxydicarbonate can be used. The synthetic resin lens of the present invention thus obtained is
It has both a high refractive index and a large Abbe's number, and has lens performance that could not be met by conventional high refractive index lenses. Furthermore, one of the features of the present invention is that the lens satisfies the practicality as a spectacle lens in terms of transparency, light resistance, workability, etc. Examples will now be described to better explain the invention. Example 1 70 parts of dicyclopentenyl acrylate, 30 parts of α-naphthyl methacrylate, benzoyl peroxide
A mixture of 0.2 parts of 2-hydroxy-4-n-octoxybenzophenone and 0.1 parts of 2-hydroxy-4-n-octoxybenzophenone was poured into a mold consisting of two glass molds and a vinyl chloride gasket, and then heated at 60°C for 10 hours at 80°C. It was kept at ℃ for 6 hours. After the polymerization was completed, the lens was removed from the mold and annealed at 100°C for 1 hour. The resulting lens has a transparency of 90%, a refractive index of 1.573, and an Atsube number of 40.
It had excellent optical properties. It also had excellent workability using a beading machine and light resistance using a weather meter. Furthermore, it is easy to apply an anti-reflection film using vacuum evaporation, and the transmittance of the lens can be reduced.
This improved to 97%, making it possible to obtain eyeglass lenses that are extremely easy to see. Examples 2 to 18 Table 1 shows the optical properties of lenses cast-polymerized in the same manner as in Example 1. All of these lenses could be coated with an antireflection film. Comparative Example 1 A mixed solution consisting of 60 parts of styrene, 30 parts of 2,2-bis(4-methacryloyloxy-3,5-dibromphenyl)propane, 10 parts of allyl cinnamate, and 0.2 parts of diisopropyl peroxycarbonate was poured onto two sheets of glass. After pouring into a mold consisting of a mold and an ethylene-vinyl acetate gasket,
The temperature was raised to 80°C over 24 hours. After polymerization, the lens was removed from the mold and annealed at 120°C for 1 hour. The obtained lens has a transmittance of 90%, a refractive index of 90%, a refractive index of 1.592, and an Atsube number of 30, and when used as an eyeglass lens, it causes significant chromatic aberration.
It was extremely difficult to see.
【表】【table】
Claims (1)
整数である）で表わされる１種以上の第１単量体
と、単独重合体の屈折率が1.55以上で、芳香族、
ハロゲン原子、イオウ原子のうちのいずれかを有
するラジカル重合可能な１種以上の第２単量体と
の共重合体から成る高屈折率合成樹脂レンズ。[Claims] 1. General formula (X represents H or CH 3 , n is an integer of 0, 1 or 2) and the homopolymer has a refractive index of 1.55 or more, aromatic,
A high refractive index synthetic resin lens made of a copolymer with one or more radically polymerizable second monomers having either a halogen atom or a sulfur atom.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11723582A JPS597901A (en) | 1982-07-06 | 1982-07-06 | Plastic lens high in refractive index |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11723582A JPS597901A (en) | 1982-07-06 | 1982-07-06 | Plastic lens high in refractive index |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS597901A JPS597901A (en) | 1984-01-17 |
| JPH0456281B2 true JPH0456281B2 (en) | 1992-09-08 |
Family
ID=14706723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11723582A Granted JPS597901A (en) | 1982-07-06 | 1982-07-06 | Plastic lens high in refractive index |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS597901A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60245613A (en) * | 1984-05-21 | 1985-12-05 | Kureha Chem Ind Co Ltd | Lens material of good dyeability |
| JPS60203607A (en) * | 1984-03-28 | 1985-10-15 | Kureha Chem Ind Co Ltd | Lens material |
| JPS6144909A (en) * | 1984-08-09 | 1986-03-04 | Japan Synthetic Rubber Co Ltd | Production of rubbery acrylate copolymer |
| DE3617755A1 (en) * | 1985-05-28 | 1986-12-04 | Nippon Sheet Glass Co., Ltd., Osaka | COPOLYMERES WITH HIGH BREAKING INDEX |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58224301A (en) * | 1982-06-24 | 1983-12-26 | Hoya Corp | Synthetic resin lens |
-
1982
- 1982-07-06 JP JP11723582A patent/JPS597901A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58224301A (en) * | 1982-06-24 | 1983-12-26 | Hoya Corp | Synthetic resin lens |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS597901A (en) | 1984-01-17 |
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