JPS6321605A - Optical member made of polarizing resin having dimming action - Google Patents
Optical member made of polarizing resin having dimming actionInfo
- Publication number
- JPS6321605A JPS6321605A JP16481286A JP16481286A JPS6321605A JP S6321605 A JPS6321605 A JP S6321605A JP 16481286 A JP16481286 A JP 16481286A JP 16481286 A JP16481286 A JP 16481286A JP S6321605 A JPS6321605 A JP S6321605A
- Authority
- JP
- Japan
- Prior art keywords
- optical member
- resin
- light control
- polarizing
- polarizing film
- 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
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 51
- 229920005989 resin Polymers 0.000 title claims description 64
- 239000011347 resin Substances 0.000 title claims description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000004313 glare Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000010408 film Substances 0.000 description 59
- 239000010410 layer Substances 0.000 description 32
- 238000002834 transmittance Methods 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000011241 protective layer Substances 0.000 description 6
- 230000010287 polarization Effects 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 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 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- -1 silver halide Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 150000004291 polyenes Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、調光作用を有する偏光性樹脂製光学部材、特
に偏光レンズ若しくはサングラスとして用いられる偏光
性樹脂製光学部材に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a polarizing resin optical member having a light control function, particularly to a polarizing resin optical member used as a polarizing lens or sunglasses.
一般に偏光レンズやサングラスは、自然光が反射された
ときに生ずる偏光を遮断し、これにより防眩作用若しく
は減光作用を果たすものであり、近年においては、この
ような特性を利用して、特に戸外における偏光防止ある
いは眩惑防止、例えばスキーの際の雪面の反射偏光の防
止、釣の場合の水面よりの乱反射光の防止、または自動
車のドライバーの眩惑防止だめのサングラス等として、
またこのような分野のほか、減光作用を目的とするサン
グラス、ファッシッンレンズ等として多方面で使用され
始めている。In general, polarized lenses and sunglasses block the polarized light that occurs when natural light is reflected, thereby achieving an anti-glare or light-reducing effect. For example, to prevent polarized light or dazzle when skiing, to prevent polarized light reflected from the snow surface when skiing, to prevent diffusely reflected light from the water surface when fishing, or as sunglasses to prevent dazzling for car drivers.
In addition to these fields, they are beginning to be used in a variety of other fields, such as sunglasses and fashion lenses for the purpose of reducing light.
従来の偏光レンズやサングラスは、以上のような特有の
作用を有してはいるが、偏光膜を備えてなる偏光レンズ
またはサングラスは、その残光率が当該偏光膜の特性に
よって決定されてしまい、入射光の強度に応じた調光機
能を得ることはできない。Conventional polarized lenses and sunglasses have the above-mentioned unique effects, but polarized lenses or sunglasses that are equipped with a polarizing film have an afterglow rate determined by the characteristics of the polarizing film. , it is not possible to obtain a dimming function according to the intensity of incident light.
一方、軽量性、加工性、耐衝撃性等の特長ををすること
から、樹脂製のレンズやサングラスが最近広く使用され
始めているが、斯かる樹脂製の光学部材に対しては好適
な調光機能を付与することが困難であった。即ち、無機
ガラスレンズに調光機能を付与するために通常用いられ
るハロゲン化銀は樹脂に対する相溶性が悪いことにより
、また調光機能を有する代表的有機化合物であるスピロ
ピランは、比較的高い２次転移温度を有する高分子物質
中では褪色が極めて遅くて実用性がないことにより、ま
た一般のスピロオキサジン化合物も一長一短があるため
、樹脂製光学部材に調光機能を付与するための有機化合
物として必ずしも満足できるものではなかった。On the other hand, lenses and sunglasses made of resin have recently begun to be widely used due to their features such as lightness, workability, and impact resistance. It was difficult to add functionality. In other words, silver halide, which is commonly used to impart a light control function to inorganic glass lenses, has poor compatibility with resins, and spiropyran, a typical organic compound with a light control function, has a relatively high secondary Since fading is extremely slow in polymeric substances with a transition temperature and is not practical, and general spirooxazine compounds also have advantages and disadvantages, they are not necessarily suitable as organic compounds for imparting light control function to resin optical members. It wasn't satisfying.
従って、戸外の自然環境下においても太陽光等の光に対
して十分な偏光機能と調光機能との両方を併せ有する樹
脂製光学部材、特に樹脂レンズや樹脂サングラスの出現
が要望されていた。Therefore, there has been a demand for resin optical members, particularly resin lenses and resin sunglasses, that have both a polarizing function and a dimming function that are sufficient for light such as sunlight even in outdoor natural environments.
しかしながら従来においては、そのような両方の機能の
何れもが十分にしかも長期間に亘って安定に発渾される
ような優れた樹脂製光学部材は提供されていない。However, in the past, there has not been provided an excellent resin optical member that satisfactorily and stably develops both of these functions over a long period of time.
本発明は、以上のような要請に応え、偏光機能と共に特
定の有機フォトクロミンク物質による調光機能を有し、
優れた偏光性と調光性の両方を備えた樹脂製光学部材、
特にそのような特性を有する樹脂レンズまたはサングラ
スを提供することを目的とする。In response to the above demands, the present invention has a polarization function and a light control function using a specific organic photochromic substance,
A resin optical member with both excellent polarization and dimming properties,
In particular, the object is to provide resin lenses or sunglasses having such characteristics.
本発明の目的は、樹脂製光学部材本体と、偏光膜とを備
えてなり、下記構造式（り乃至構造式（ＩＩＩ）の何れ
かによって表わされるスピロオキサジン化合物の少なく
とも１種を含有する調光機能部分を有することを特徴と
する８周光作用を有する偏光性樹脂製光学部材によって
達成される。An object of the present invention is to provide a light control member comprising a resin optical member main body and a polarizing film, and containing at least one type of spirooxazine compound represented by any of the following structural formulas (RI to Structural formula (III)). This is achieved by an optical member made of polarizing resin that has a functional part and has an eight-round optical effect.
（式中、Ｘは水素原子、ハロゲン原子、シアノ基、低級
アルキル基、低級アルコキシ基を示し、Ｙは低級アルキ
ル基、低級アルコキシアルキル基、各種置換アリルアル
キル基、千ＣＨり −−Ｃ０ＯＲを示す、但しＲは低級
アルキル基、ｎは１〜６の整数を示す、）
〔効果〕
本発明による調光作用を有する偏光性樹脂製光学部材は
、偏光膜による偏光作用を有するほか、特有のｆ機フォ
トクロミック材料を含有する調光機能部分を有するので
、入射光の強弱に応じて光量を調節することができ、防
眩作用と調光作用を同時に備えたものとなり、目を保護
するという観点からも非常に有用なものである。(In the formula, X represents a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group, a lower alkoxy group, and Y represents a lower alkyl group, a lower alkoxyalkyl group, various substituted arylalkyl groups, 1,000 CH--C0OR (where R is a lower alkyl group, and n is an integer of 1 to 6.) [Effects] The polarizing resin optical member having a dimming effect according to the present invention not only has a polarizing effect due to a polarizing film, but also has a unique f Since it has a dimming function part containing a photochromic material, it is possible to adjust the amount of light according to the intensity of the incident light, and it has both anti-glare and dimming effects, from the viewpoint of protecting the eyes. is also very useful.
本発明において用いられる光学部材本体の材質は、樹脂
であれば特に附定されず、通常の樹脂レンズあるいはサ
ングラスに用いられる樹脂材料を使用することができる
。その具体例としては、例えば、ジエチレングリコール
ビスアリルカーボネート樹脂、メチルメタクリレート樹
脂、各種の透明ナイロン樹脂、ポリカーボネート樹脂、
ポリスチレン樹脂、ポリウレタン樹脂、ポリエステル樹
脂並びに最近において樹脂レンズの間圧折率化という観
点から開発が進められている芳香族系樹脂、臭素原子を
含む芳香族系樹脂等の種々の樹脂を挙げることができる
。The material of the optical member main body used in the present invention is not particularly limited as long as it is a resin, and resin materials used for ordinary resin lenses or sunglasses can be used. Specific examples include diethylene glycol bisallyl carbonate resin, methyl methacrylate resin, various transparent nylon resins, polycarbonate resin,
Various resins include polystyrene resins, polyurethane resins, polyester resins, aromatic resins that have recently been developed from the perspective of increasing the refractive index of resin lenses, and aromatic resins containing bromine atoms. can.
本発明において、偏光膜としては種々のものを利用する
ことができる。その具体例としては、例えばいわゆる薄
膜型偏光フィルムと呼ばれるヨウ素−ポリビニルアルコ
ール偏光フィルム、二色性の大きい染料−ポリビニルア
ルコール偏光フィルム、ポリビニルアルコールやポリ塩
化ビニル等を分子内脱水または脱塩酸することによりポ
リエン構造を形成し、共役二重結合によって偏光特性を
得るようにしたいわゆるポリビニレン系偏光フィルム、
その他を挙げることができる。In the present invention, various polarizing films can be used. Specific examples include iodine-polyvinyl alcohol polarizing film called a so-called thin film type polarizing film, highly dichroic dye-polyvinyl alcohol polarizing film, and intramolecular dehydration or dehydrochlorination of polyvinyl alcohol, polyvinyl chloride, etc. A so-called polyvinylene polarizing film that forms a polyene structure and obtains polarizing properties through conjugated double bonds.
Others can be mentioned.
ヨウ素−ポリビニルアルコール偏光フィルムはニュート
ラル（中性色）系あるいは青色系が主であり、特にカラ
ー化を目的とする場合には染料系７）！リビニルアルコ
ール偏光フィルムが本発明に好適に使用される。偏光膜
を保護するため、当該偏光膜の両面または一面に他の透
明フィルム例えばトリアセテートフィルムよりなる保護
フィルムを積層して保護層を形成することが好ましい。Iodine-polyvinyl alcohol polarizing films are mainly neutral or blue, and dye-based 7)! Rivinyl alcohol polarizing films are preferably used in the present invention. In order to protect the polarizing film, it is preferable to form a protective layer by laminating another transparent film, such as a protective film made of a triacetate film, on both surfaces or one surface of the polarizing film.
本発明偏光性樹脂製光学部材においては、調光機能を得
るために、そのいずれかの部分に、下記構造式（Ｉ）乃
至構造式（Ｉ［＋）の何れかによって表わされるスピロ
オキサジン化合物の少なくとも１種またはそれ以上が含
有せしめられる。In order to obtain a light control function in the polarizing resin optical member of the present invention, a spirooxazine compound represented by any of the following structural formulas (I) to (I[+)] is added to any part thereof. At least one or more types are contained.
構造式（Ｉｌｌ）
（式中、Ｘは水素原子、ハロゲン原子、シアン基、低級
アルキル基、低級アルコキシ基を示し、Ｙハ低級アルキ
ル基、低級アルコキシアルキル基、各種置換アリルアル
キル基、＋Ｃ１ｈ）、１ＣＯＯＲを示す、但しＲは低級
アルキル基、ｎは１〜６の整数を示す、）
上記スピロオキサジン化合物の具体的な例としては、例
えば、
１．３．３− ）リメチルスビロ〔インドリン−２，３
゜−（３Ｆ（）ナフト（２，１−ｂ） （Ｉ，４）オキ
サジン〕、５−クロロ−１，３，３−）リンチルスピロ
〔インドリン−２，３’ −（３Ｈ）ナフト（２，１−
ｂ ） （Ｉ，４）オキサジン〕、
１、．３．３．５−テトラメチル−９゛−メトキシスピ
ロ〔インドリン−２，３°−（３Ｈ）ナフト（２，１−
ｂ）（Ｉ，４）オキサジン〕、
１−イソプロピル−３，３，５−トリメチルスピロ〔イ
ンドリン−２，３′−（３Ｈ）ナフト（２，１−ｂ〕（
Ｉ，４）オキサジン〕、
１−（ｐ−クロロベンジル）−３，３−ジメチルスピロ
〔インドリン−２，３’ −（３Ｈ）ナフト〔２，１−
ｂ）（Ｉ，４）オキサジン〕、
■−（β−メトキシエチル）−３，３−ジメチル−９゛
−メトキシスピロ〔インドリン−２，３′〜（３Ｈ）ナ
フト（２，１−ｂ ） （Ｉ，４）オキサジン〕、１．
３．３−トリメチルスピロ〔インドリン−２，２゛−（
２Ｈ）フェナントロ（９，１０−ｂ ） （Ｉ，４）オ
キサジン〕、
１．３．３−トリメチルスピロ〔インドリン−２，２゛
−（２Ｈ）ピリド（３，２−ｆ ） （Ｉ，４）ベンゾ
オキサジン〕、
その他を挙げることができるが、勿論これらに限定され
るものではない。Structural formula (Ill) (wherein, X represents a hydrogen atom, a halogen atom, a cyan group, a lower alkyl group, a lower alkoxy group, and Y represents a lower alkyl group, a lower alkoxyalkyl group, various substituted arylalkyl groups, +C1h), 1COOR, where R is a lower alkyl group and n is an integer of 1 to 6.) Specific examples of the above spirooxazine compounds include 1.3.3-)limethylsubiro[indoline-2,3
゜-(3F()naphtho(2,1-b)(I,4)oxazine], 5-chloro-1,3,3-)lyntylspiro[indoline-2,3'-(3H)naphtho(2,1 −
b) (I,4)oxazine], 1,. 3.3.5-tetramethyl-9゛-methoxyspiro[indoline-2,3°-(3H)naphtho(2,1-
b) (I,4)oxazine], 1-isopropyl-3,3,5-trimethylspiro[indoline-2,3'-(3H)naphtho(2,1-b]
I,4)oxazine], 1-(p-chlorobenzyl)-3,3-dimethylspiro[indoline-2,3'-(3H)naphtho[2,1-
b) (I,4)oxazine], ■-(β-methoxyethyl)-3,3-dimethyl-9'-methoxyspiro[indoline-2,3'-(3H)naphtho(2,1-b) ( I, 4) Oxazine], 1.
3.3-trimethylspiro[indoline-2,2゛-(
2H) phenanthro(9,10-b) (I,4)oxazine], 1.3.3-trimethylspiro[indoline-2,2゛-(2H)pyrido(3,2-f) (I,4) benzoxazine], and others, but are not limited to these, of course.
これらのスピロオキサジン化合物は、自然の環境下にお
いて、光の照射および除去に伴う呈色および褪色の繰り
返し変化を生ずる調光機能が長期間安定に発渾され、特
に太陽光の下での使用においても長期間に亘ってその優
れた調光機能を維持することができ、しかも比較的高温
においてもその作用が安定なものである。In natural environments, these spirooxazine compounds exhibit a dimming function that repeatedly changes color and fading as light is irradiated and removed. It is also possible to maintain its excellent dimming function over a long period of time, and its effect is stable even at relatively high temperatures.
次に上記の偏光膜およびスピロオキサジン化合物を樹脂
製光学部材本体に適用する手段について述べる。Next, a means for applying the above polarizing film and spirooxazine compound to the resin optical member body will be described.
偏光膜を樹脂製光学部材本体に設けるＬ！様としては、
（イ）第１図に示すように、光学部材本体を構成すべき
２枚の光学部材要素１１．１２間に偏光膜Ｐを介挿した
状態で貼り合わせた態様、
（ロ）第２図に示すように、光学部材本体１３の少なく
とも一面に接着剤を用いて偏光膜Ｐを貼り付けた態様、
（ハ）注型重合により光学部材本体１３を形成する場合
において、その材料モノマー中に偏光膜Ｐを浸漬した状
態でモノマーを重合させ、光学部材本体１３中に偏光膜
Ｐを埋設した態様、のいずれとすることもできる。なお
既述のように当該偏光膜にはその両面若しくは一面に保
護層が形成されていることが好ましい。Providing a polarizing film on the resin optical member body L! (a) As shown in FIG. 1, two optical member elements 11 and 12 that constitute the optical member body are bonded together with a polarizing film P inserted between them; (b) As shown in FIG. 2, a mode in which a polarizing film P is attached to at least one surface of the optical member main body 13 using an adhesive; (c) In the case where the optical member main body 13 is formed by cast polymerization, the material monomer It is also possible to polymerize monomers while the polarizing film P is immersed therein, and embedding the polarizing film P in the optical member main body 13. As mentioned above, it is preferable that the polarizing film has a protective layer formed on one or both sides thereof.
調光機能を得るための前記特定のスピロオキサジン化合
物を通用するためには、当該スピロオキサジン化合物を
含有する樹脂よりなる調光層を、以上のように偏光膜を
設けた光学部材本体に設ける手段、あるいはそのような
独立した調光層によらずに、当該スピロオキサジン化合
物を、以上のように偏光膜を設けた光学部材本体の当該
偏光膜および光学部材本体の何れか一方または両方に含
有せしめる手段を利用することができる。In order to use the specific spirooxazine compound for obtaining a light control function, it is necessary to provide a light control layer made of a resin containing the spirooxazine compound on the optical member body provided with the polarizing film as described above. , or instead of using such an independent light control layer, the spirooxazine compound is contained in either or both of the polarizing film and the optical member main body of the optical member main body provided with the polarizing film as described above. means are available.
後者の手段による場合において、スピロオキサジン化合
物を偏光膜中に含有させるためには、偏光膜の作製時に
おいて、ヨウ素や二色性染料等の偏光物質と共に当該ス
ピロオキサジン化合物を共存させる方法を用いることが
できる。あるいは光学部材本体に設けられた偏光膜を、
例えば当該スピロオキサジン化合物の有機溶媒による溶
液中に浸漬させることによって接触させ、これによって
スピロオキサジン化合物を偏光膜中に拡散させることが
できる。またこの場合において、偏光膜に保護層が形成
されているときは、当該偏光膜および保護層の一方また
は両方に拡散させればよい。In the case of the latter method, in order to incorporate the spirooxazine compound into the polarizing film, a method is used in which the spirooxazine compound is allowed to coexist with a polarizing substance such as iodine or dichroic dye during the production of the polarizing film. Can be done. Or a polarizing film provided on the optical member body,
For example, the spirooxazine compound can be brought into contact by immersing it in a solution of an organic solvent, thereby diffusing the spirooxazine compound into the polarizing film. Moreover, in this case, when a protective layer is formed on the polarizing film, it may be diffused into one or both of the polarizing film and the protective layer.
また同様の浸漬手段によって、光学部材本体中にスピロ
オキサジン化合物を拡散させて含有させることができる
。Furthermore, the spirooxazine compound can be diffused and contained in the optical member main body using the same dipping means.
前者の手段、即ち調光層を設けることによってスピロオ
キサジン化合物を通用する場合には、当該スピロオキサ
ジン化合物を、調光層用樹脂材料と共に有機溶媒に溶解
させ、この溶液を、偏光膜を設けた光学部材本体の表面
に塗布し、必要に応じて硬化させればよい、ここで用い
られる調光層用樹脂材料の種類は特に制限はな（、透明
な樹脂材料であれば種々のものを用いることができる。In the former method, that is, when a spirooxazine compound is used by providing a light control layer, the spirooxazine compound is dissolved in an organic solvent together with the resin material for the light control layer, and this solution is used to form a light control layer. The type of resin material for the light control layer used here is not particularly limited; it can be applied to the surface of the optical member body and cured if necessary (various resin materials can be used as long as it is a transparent resin material). be able to.
その具体例としては、例えば、ポリメチルメタクリレー
ト、ポリスチレン、ポリ酢酸ビニル、エチレン−酢酸ビ
ニル共重合体、ポリカーボネート、ポリ塩化ビニル、ポ
リエチレンテレフタレート等の熱可塑性樹脂、ポリウレ
タン、エポキシ樹脂、フェノール樹脂等の？ｊ！、ｌｉ
Ｊ！化性樹脂を挙げることができる。また一般にハード
コート剤として知られている光架橋型の多官能性アクリ
ル系樹脂、シリコーン系ハードコート剤用樹脂も用いる
ことができる。Specific examples include thermoplastic resins such as polymethyl methacrylate, polystyrene, polyvinyl acetate, ethylene-vinyl acetate copolymer, polycarbonate, polyvinyl chloride, polyethylene terephthalate, polyurethane, epoxy resin, phenolic resin, etc. j! ,li
J! Examples include chemical resins. Furthermore, photocrosslinkable polyfunctional acrylic resins and silicone hard coating resins, which are generally known as hard coating agents, can also be used.
調光層は、例えば第４図に示すように、第１図に示した
Ｇ様で偏光膜Ｐを有する光学部材本体の一方の光学部材
要素１１の表面または他方の光学部材要素１２の表面に
設けることができる。Ｃが調光層を示す、あるいは第５
図に示すように、２枚の光学部材要素１１と１２との間
に、偏光膜Ｐと積層された状態に調光層Ｃを設けること
も可能であり、更に第６図に示すように、光学部材本体
１３の表面に、偏光膜Ｐと調光層Ｃとの積層体を設けて
もよい、そして第５図および第６図の構成においては、
偏光膜Ｐと調光ＮＣとの順序は特に限定されるものでは
ない、即ち、調光層を単独で、第１図〜第３図に示した
偏光層Ｐの場合と同様の態様で、貼り合わせ、貼り付け
、注型重合時の埋設等の手段によって設けることができ
る。For example, as shown in FIG. 4, the light control layer is formed on the surface of one optical member element 11 or the surface of the other optical member element 12 of the optical member main body having the polarizing film P in the shape G shown in FIG. can be provided. C indicates a light control layer, or the fifth
As shown in the figure, it is also possible to provide a light control layer C between the two optical member elements 11 and 12 in a state where it is laminated with a polarizing film P. Furthermore, as shown in FIG. A laminate of a polarizing film P and a light control layer C may be provided on the surface of the optical member main body 13, and in the configurations shown in FIGS. 5 and 6,
The order of the polarizing film P and the light control NC is not particularly limited. In other words, the light control layer may be attached alone in the same manner as the polarizing layer P shown in FIGS. 1 to 3. It can be provided by means such as alignment, pasting, and embedding during cast polymerization.
以上のように前記スピロオキサジン化合物は、何れも樹
脂よりなる光学部材本体、偏光膜若しくはその保護層ま
たは調光層中に含有されて調光機能部分が形成されるが
、当該調光機能部分の樹脂は三次元架橋構造を有するも
のであることが好ましい、三次元架橋構造の樹脂中にお
いては、当該スピロオキサジン化合物は、比較的高い温
度においても優れた調光機能を確実にまた長期間に亘っ
て発揮することができるからである。As described above, the spirooxazine compound is contained in the optical member main body made of resin, the polarizing film or its protective layer, or the light control layer to form the light control function part. It is preferable that the resin has a three-dimensional crosslinked structure. In the resin having a three-dimensional crosslinked structure, the spirooxazine compound ensures excellent dimming function even at relatively high temperatures and for a long period of time. This is because they can demonstrate their abilities.
従って、本発明において調光層を設ける場合には、その
調光層を形成する樹脂として、熱硬化性樹脂やハードコ
ート剤用樹脂のような三次元架橋樹脂を構成する樹脂前
駆体あるいは多官能アクリル化合物中に混入させて調光
層用塗布液とし、これを、偏光膜を備えた光学部材本体
の表面に塗布し乾燥して被膜を形成させあるいは更に硬
化させ、これによって調光層を偏光膜の表面に設けるこ
とが好ましい。Therefore, when providing a light control layer in the present invention, the resin forming the light control layer may be a resin precursor or a polyfunctional resin that constitutes a three-dimensionally crosslinked resin such as a thermosetting resin or a resin for a hard coating agent. This is mixed into an acrylic compound to form a coating solution for a light control layer, and this is applied to the surface of an optical member body equipped with a polarizing film and dried to form a film or further hardened, thereby changing the light control layer into a polarizing layer. It is preferable to provide it on the surface of the membrane.
前記スピロオキサジン化合物は、三次元架橋樹脂１００
重量部に対して０．０１〜５０重量部の割合で含有され
ることが好ましく、また調光層の厚みは１〜１００μの
範囲内であることが好ましい。The spirooxazine compound is a three-dimensional crosslinked resin 100
It is preferably contained in a ratio of 0.01 to 50 parts by weight based on parts by weight, and the thickness of the light control layer is preferably in the range of 1 to 100 μm.
独立の調光層が形成されない場合には、光学部材本体ま
たは偏光膜を若しくはその保護膜を三次元架橋構造を有
する樹脂によって形成し、スピロオキサジン化合物の溶
液中に浸漬することにより、スピロオキサジン化合物を
当該樹脂中に拡散含有させて調光機能部分を形成するこ
とが好ましい。When an independent light control layer is not formed, the optical member main body, polarizing film, or its protective film is formed from a resin having a three-dimensional crosslinked structure, and the spirooxazine compound is immersed in a solution of the spirooxazine compound. It is preferable that the light control function portion be formed by diffusing and containing the light in the resin.
この場合には、特に偏光膜は第１図のａ様で光学部材本
体に具備されることが好ましい。In this case, it is particularly preferable that the polarizing film is provided on the optical member body as shown in a in FIG.
以上のようにして、偏光機能と特定のスピロオキサジン
化合物よりなる有機フォトクロミンク物質による調光機
能の二つの機能を共に有する樹脂製光学部材を得ること
ができる。この光学部材は偏光レンズ若しくはサングラ
スとして好適に用いることができるが、更にこの種の偏
光レンズやサングラスにおいて通常施されるハードコー
トや無反射コートをこの光学部材に形成することもでき
、また染色することも可能である。特にスピロオキサジ
ン化合物を含有する調光機能部分が外表面に露出して存
在する場合には、相当の長時間の経過後においては大気
中の水分、人体の汗等によりスピロオキサジン化合物の
加水分解による劣化を生ずるおそれがあり、このため、
表面にシリコーン系のハードコート層を設けることが好
ましい。ハードコート層の厚みは０．１〜２００ μの
範囲が好ましい。In the manner described above, it is possible to obtain a resin optical member having two functions: a polarizing function and a dimming function using an organic photochromic substance made of a specific spirooxazine compound. This optical member can be suitably used as polarized lenses or sunglasses, but it is also possible to form a hard coat or anti-reflection coating on this optical member, which is usually applied to polarized lenses or sunglasses, or to dye it. It is also possible. In particular, if the light control function part containing the spirooxazine compound is exposed on the outer surface, the spirooxazine compound may be hydrolyzed by moisture in the atmosphere, human sweat, etc. after a considerable period of time has passed. There is a risk of deterioration, and for this reason,
It is preferable to provide a silicone hard coat layer on the surface. The thickness of the hard coat layer is preferably in the range of 0.1 to 200 μm.
以下本発明の実施例について説明するが、これによって
本発明が限定されるものではない。Examples of the present invention will be described below, but the present invention is not limited thereto.
実施例１
市販のポリビニルアルコール−ヨウ素錯体系偏光膜（中
性グレー色、偏光度９４．６％、単体透過率４５．８％
、平行透過率３９．６％、直交透過率２．２％）の表面
にセルロース樹脂からなる保護層を設けたものを球面レ
ンズ状に熱プレス成形し、これをガラス製のレンズモー
ルド中に入れて保持し、このモールド中に、ジエチレン
グリコールビスアリルカーボネート１００重量部と、重
合開始剤としてイソプロピルパーオキシジカーボネート
２重量部とのモノマー混合物を注入し、温度を４０℃か
ら８０℃へ順次２０時間かけて上昇させて重合させ、こ
れにより、第３図に示すように内部に埋設した偏光膜を
存する偏光性樹脂製レンズを作製した。Example 1 Commercially available polyvinyl alcohol-iodine complex polarizing film (neutral gray color, degree of polarization 94.6%, single transmittance 45.8%)
, parallel transmittance 39.6%, orthogonal transmittance 2.2%) with a protective layer made of cellulose resin on the surface, which was hot press molded into a spherical lens shape, and placed in a glass lens mold. A monomer mixture of 100 parts by weight of diethylene glycol bisallyl carbonate and 2 parts by weight of isopropyl peroxydicarbonate as a polymerization initiator was poured into the mold, and the temperature was successively raised from 40°C to 80°C over 20 hours. The mixture was raised to polymerize, thereby producing a polarizing resin lens having a polarizing film embedded therein as shown in FIG.
次に１．３．３− トリメチルスピロ〔インドリン−２
，３’−（３Ｈ）ナフト（２，１−ｂ） （Ｉ，４）オ
キサジ７３５重量部を、エポキシ樹脂前駆体「エポニフ
クス１１１００クリヤー」（大日本塗料−社製）溶液２
００ｃｃに溶解させて調光層用塗布液を調製した。この
調光層用塗布液を上記偏光性樹脂製レンズの凸面に塗布
し乾燥させて厚さ１２μの調光層を形成し、本発明に係
る樹脂製レンズを作製した。Next, 1.3.3-trimethylspiro[indoline-2
, 3'-(3H) naphtho(2,1-b) (I,4) 735 parts by weight of oxadi was added to epoxy resin precursor "Eponifux 11100 Clear" (manufactured by Dainippon Toyo Co., Ltd.) solution 2.
A coating liquid for a light control layer was prepared by dissolving it in 00cc. This light control layer coating liquid was applied onto the convex surface of the polarizing resin lens and dried to form a light control layer having a thickness of 12 μm, thereby producing a resin lens according to the present invention.
このレンズを太陽光に当てたところ、徐々にグレーから
深緑色に変化した。また、このレンズを直射日光中に３
分間放置し、その後直ちに単体透過率を測定したところ
、４３％であったものが２８％に変化し、有効な調光機
能を有することが示された。また呈色したレンズを５分
間暗所に置いたところ、はぼ元の色調に回復した。When this lens was exposed to sunlight, it gradually turned from gray to dark green. Also, do not expose this lens to direct sunlight for 30 minutes.
When it was left to stand for a minute and the single transmittance was immediately measured, the transmittance changed from 43% to 28%, indicating that it had an effective dimming function. When the colored lens was left in a dark place for 5 minutes, the color returned to its original color.
なお、上記単体透過率の測定は、１５０Ｗのキセノンラ
ンプを光源とする瞬間マルチ測光システムｒＭｃＰＤ
１００ＯＪ （大塚電子■製）を用い、波長６１０〜６
２０ ｎａの光の透過率の平均値を求めることにより行
った。The measurement of the single transmittance was performed using an instantaneous multi-photometering system rMcPD using a 150W xenon lamp as a light source.
Using 100OJ (manufactured by Otsuka Electronics), wavelength 610~6
This was done by determining the average value of the transmittance of light at 20 na.
実施例２
実施例１で作製した調光機能を有する偏光性樹脂製レン
ズの調光層面に、市販のシリコーン系ハードコート剤「
トスガード５２０Ｊ （東芝シリコーン社！！！りを
塗布し、常法に従って加熱乾燥硬化させて厚さ７μのハ
ードコート層を形成した。Example 2 A commercially available silicone hard coating agent "
TOSGUARD 520J (Toshiba Silicone Co., Ltd.) was applied and cured by heating and drying according to a conventional method to form a hard coat layer with a thickness of 7 μm.
このレンズを試料としてウェザ−メーター「スーパーロ
ングライフ・サンシャイン・ウェザ−メーター」（スガ
試験機社製）により促進曝露テストを行ったところ、１
００時間経過後においても初期と殆ど同様の優れた偏光
作用および調光作用を有することが認められた。An accelerated exposure test was conducted using this lens as a sample using a weather meter "Super Long Life Sunshine Weather Meter" (manufactured by Suga Test Instruments Co., Ltd.).
Even after 00 hours had passed, it was found that the film had almost the same excellent polarizing effect and dimming effect as at the initial stage.
実施例３
市販のポリメチルメタクリレートよりなるサングラスの
凸面に、実施例１におけると同様の偏光膜をエポキシ接
着剤で貼り合わせ、第２図に示す態様の偏光性サングラ
スを作った。Example 3 A polarizing film similar to that in Example 1 was bonded to the convex surface of a commercially available sunglass made of polymethyl methacrylate using an epoxy adhesive to produce polarized sunglasses as shown in FIG. 2.
次に、１，３．３− ）リンチルスピロ〔インドリン−
２，２”−（２Ｈ）フェナントロ（９，１０−ｂ ）
（Ｉ，４）オキサジン〕１０ｇを、室温で液状のエポキ
シ樹脂前駆体「エポテック３０１Ｊ （米国エポキシ
・テクノロジー社製、温度２５℃における粘度１００
ｃｐｓ）１００ｇに熔解して調光層用塗布液を調製し、
この塗布液を、上記偏光性サングラスの偏光膜上に均一
に塗布し、温度６５℃で３時間放置して硬化させて厚さ
約１５μの調光層を形成し、以て本発明に係るサングラ
スを作製した。Next, 1,3.3-) lynchylspiro [indoline-
2,2”-(2H)phenanthro(9,10-b)
(I, 4) Oxazine] 10g was added to an epoxy resin precursor "Epotec 301J" (manufactured by Epoxy Technology Co., USA, viscosity 100 at 25°C), which is liquid at room temperature.
cps) to prepare a coating solution for a light control layer,
This coating solution is uniformly applied onto the polarizing film of the polarized sunglasses, and left to harden at a temperature of 65° C. for 3 hours to form a light control layer with a thickness of about 15 μm. was created.
このサングラスを、直射日光の下に約３０℃の温度で３
分間放置し、その後直ちに透過率を測定したところ、４
３％であったものが３２％に変化し、を効な調光機能を
有することが示された。太陽光の下での色調は深緑色で
あった。更に暗所に５分間程度放置すると呈色は完全に
消失し、偏光膜によるグレーの色に復帰した。Wear these sunglasses under direct sunlight at a temperature of about 30℃ for 3 days.
When I left it for a minute and measured the transmittance immediately after that, it was 4.
3% changed to 32%, indicating that it has an effective dimming function. The color under sunlight was deep green. Further, when it was left in a dark place for about 5 minutes, the coloration completely disappeared and the color returned to the gray color caused by the polarizing film.
実施例４
十分に精製した５−クロロ−１，３，３−トリメチルス
ピロ〔インドリン−２，３°−ナフト（２，１−ｂ）（
Ｉ，４）−オキサジン）１０ｇを、エチレン−酢酸ビニ
ル共重合体樹脂「エバフレックス１５０Ｊ３０ｇと共に
トルエン３００ｇに加熱溶解して調光フィルム形成液を
調製し、この液をテフロンシート上に流延乾燥して厚さ
２０μの調光フィルムを作製した。Example 4 Thoroughly purified 5-chloro-1,3,3-trimethylspiro[indoline-2,3°-naphtho(2,1-b) (
A light control film forming solution was prepared by heating and dissolving 10 g of ethylene-vinyl acetate copolymer resin "Evaflex 150J" in 300 g of toluene, and this solution was cast on a Teflon sheet and dried. A light control film with a thickness of 20 μm was prepared.
この調光フィルムおよび市販のマルチカラー偏光フィル
ム（青色、透過率４０％、偏光度９１％）の各−面に、
実施例３において用いたものと同様のエポキシ樹脂前駆
体「エボテック３０１」を塗布して当該各−面同士を貼
り合わせ、これを更に紫外線吸収剤を含有しないジエチ
レングリコールビスアリルカーボネート樹脂ｒＣＲ−３
９Ｊを材質とする厚さ１．２ ｍａ＋の樹脂製レンズ要
素２枚の間に挟んで圧着し、その後これを温度８０℃に
３時間保持することにより、２枚のレンズ要素間に偏光
膜と調光膜とが積層して設けられた第５図に示す構成の
本発明に係る偏光性樹脂製レンズを作製した。そしてこ
のレンズの両面に実施例２と同じハードコート層を形成
した。On each side of this light control film and a commercially available multicolor polarizing film (blue, transmittance 40%, polarization degree 91%),
The same epoxy resin precursor "Evotech 301" as used in Example 3 is applied and the respective surfaces are bonded together, and this is further coated with diethylene glycol bisallyl carbonate resin rCR-3 which does not contain an ultraviolet absorber.
A polarizing film was formed between the two lens elements by sandwiching and press-bonding them between two resin lens elements made of 9J and having a thickness of 1.2 ma+, and then keeping them at a temperature of 80°C for 3 hours. A polarizing resin lens according to the present invention having the structure shown in FIG. 5 and having a light control film laminated thereon was produced. Then, the same hard coat layer as in Example 2 was formed on both sides of this lens.
このようにして作製されたレンズを太陽光に３分間照ら
したところ、青い偏光膜の色が更に深み帯びた。また直
ちに透過率を測定したところ、４０％であったものが３
２％に変化し、良好な調光機能を有することが示された
。またウェザ−メータによる促進劣化試験による操り返
しテストの結果、１００時間ｉｉｉ後も初期と殆ど同様
の有効な偏光性および調光機能を維持していた。また、
暗所に５分間程変放置することによって呈色は完全に消
失し、元の青色の偏光膜の色に戻った。When the lens thus prepared was exposed to sunlight for 3 minutes, the color of the blue polarizing film became even deeper. Also, when I immediately measured the transmittance, the transmittance was 40%, but it turned out to be 3
2%, indicating that it has a good dimming function. Further, as a result of repeated testing using an accelerated deterioration test using a weather meter, it was found that even after 100 hours iii, the effective polarization and dimming functions were maintained, which were almost the same as those at the initial stage. Also,
By leaving it in a dark place for about 5 minutes, the coloration completely disappeared and the color returned to the original blue color of the polarizing film.
実施例５
実施例１におけると同様にして作製した、ポリビニルア
ルコール−ヨウ素錯体系偏光膜を埋設した状態で有する
ジエチレングリコールビスアリルカーボネート製レンズ
を、ジエチレングリコール１００重量部と、１，３．３
−トリメチルスピロ〔インドリン−２，２’ −（２Ｈ
）ピリド（３，２−ｆ ） （Ｉ，４）ベンゾオキサジ
７７３重量部との混合液中に温度１１０℃で５分間浸漬
させ、これによってスピロオキサジン化合物をレンズの
表面部分に拡散させた。Example 5 A diethylene glycol bisallyl carbonate lens having a polyvinyl alcohol-iodine complex polarizing film embedded therein, prepared in the same manner as in Example 1, was mixed with 100 parts by weight of diethylene glycol and 1.3.3 parts by weight of diethylene glycol.
-trimethylspiro[indoline-2,2'-(2H
) Pyrido(3,2-f)(I,4) The lens was immersed in a mixed solution of 773 parts by weight of benzoxadi at a temperature of 110° C. for 5 minutes, thereby diffusing the spirooxazine compound to the surface portion of the lens.
このレンズを水で十分洗浄した後、その表面上に実施例
２と同様の条件で膜厚約７μのシリコーン系ハードコー
ト層を形成し、本発明に係る偏光性樹脂製レンズを作製
した。After thoroughly washing this lens with water, a silicone hard coat layer having a thickness of about 7 μm was formed on the surface under the same conditions as in Example 2, thereby producing a polarizing resin lens according to the present invention.
このレンズに約３０℃の温度で約３分量大陽光を照らし
たところ深青色を示した。また直ちに透過率を測定した
ところ、４３％であったものが３５％に変化し、優れた
調光機能を有していることが認められた。When this lens was exposed to about 3 portions of sunlight at a temperature of about 30°C, it showed a deep blue color. When the transmittance was immediately measured, the transmittance changed from 43% to 35%, indicating that it had an excellent light control function.
第１図〜第３図はそれぞれ偏光膜を設ける態様について
の説明用断面図、第４図〜第６図はそれぞれ更に調光層
を設ける態様についての説明用断面図である。
１１．１２・・・光学部材要素 １３・・・光学部材
本体Ｐ・・・偏光膜 Ｃ・・・調光層ポ１図
一参２ｍ
＄３ｍFIGS. 1 to 3 are sectional views for explaining an embodiment in which a polarizing film is provided, and FIGS. 4 to 6 are sectional views for explaining an embodiment in which a light control layer is further provided. 11.12... Optical member element 13... Optical member body P... Polarizing film C... Light control layer P1 See Figure 1 2m $3m
Claims (1)
記構造式（ I ）乃至構造式（III）の何れかによって表
わされるスピロオキサジン化合物の少なくとも１種を含
有する調光機能部分を有することを特徴とする調光作用
を有する偏光性樹脂製光学部材。 構造式（ I ） ▲数式、化学式、表等があります▼ 構造式（II） ▲数式、化学式、表等があります▼ 構造式（III） ▲数式、化学式、表等があります▼ （式中、Ｘは水素原子、ハロゲン原子、シアノ基、低級
アルキル基、低級アルコキシ基を示し、Ｙは低級アルキ
ル基、低級アルコキシアルキル基、各種置換アリルアル
キル基、−（ＣＨ＿２）＿ｎ−ＣＯＯＲを示す。但しＲ
は低級アルキル基、ｎは１〜６の整数を示す。） ２）調光機能部分が前記スピロオキサジン化合物を含有
する三次元架橋樹脂よりなる調光層であり、当該調光層
が、偏光膜を備えた樹脂製光学部材本体の表面に設けら
れていることを特徴とする特許請求の範囲第１項記載の
偏光性樹脂製光学部材。 ３）樹脂製光学部材本体が三次元架橋樹脂からなり、前
記スピロオキサジン化合物が当該光学部材本体内に含有
されて調光機能部分が形成されていることを特徴とする
特許請求の範囲第１項記載の偏光性樹脂製光学部材。 ４）レンズ若しくはサングラスとして用いられる特許請
求の範囲第１項記載の偏光性樹脂製光学部材。[Scope of Claims] 1) Comprising a resin optical member body and a polarizing film, and containing at least one spirooxazine compound represented by any of the following structural formulas (I) to (III). 1. An optical member made of polarizing resin having a light control function, characterized by having a light control function part. Structural formula (I) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ Structural formula (II) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ Structural formula (III) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, represents a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group, a lower alkoxy group, and Y represents a lower alkyl group, a lower alkoxyalkyl group, various substituted arylalkyl groups, -(CH_2)_n-COOR.However, R
represents a lower alkyl group, and n represents an integer of 1 to 6. ) 2) The light control function portion is a light control layer made of a three-dimensional crosslinked resin containing the spirooxazine compound, and the light control layer is provided on the surface of a resin optical member body provided with a polarizing film. An optical member made of polarizing resin according to claim 1, characterized in that: 3) Claim 1, wherein the resin optical member main body is made of a three-dimensional crosslinked resin, and the spirooxazine compound is contained in the optical member main body to form a light control function part. The polarizing resin optical member described above. 4) The polarizing resin optical member according to claim 1, which is used as a lens or sunglasses.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61164812A JPH0666003B2 (en) | 1986-07-15 | 1986-07-15 | Method for manufacturing optical member made of polarizing resin having dimming effect |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61164812A JPH0666003B2 (en) | 1986-07-15 | 1986-07-15 | Method for manufacturing optical member made of polarizing resin having dimming effect |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6321605A true JPS6321605A (en) | 1988-01-29 |
| JPH0666003B2 JPH0666003B2 (en) | 1994-08-24 |
Family
ID=15800387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61164812A Expired - Lifetime JPH0666003B2 (en) | 1986-07-15 | 1986-07-15 | Method for manufacturing optical member made of polarizing resin having dimming effect |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0666003B2 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01170904A (en) * | 1987-12-25 | 1989-07-06 | Toray Ind Inc | Polarizing sheet having photochromic property |
| WO1989011673A1 (en) * | 1988-05-17 | 1989-11-30 | Kabushiki Kaisha Biotron | Dimmer lens, dimmer glasses and sun glasses and production of dimmer lens |
| JPH02332U (en) * | 1988-06-14 | 1990-01-05 | ||
| JPH0294115U (en) * | 1988-12-29 | 1990-07-26 | ||
| WO2001084218A1 (en) * | 2000-05-02 | 2001-11-08 | Yamamoto Kogaku Co., Ltd. | Polarizing optical article |
| WO2001084217A1 (en) * | 2000-05-02 | 2001-11-08 | Yamamoto Kogaku Co., Ltd. | Transparent optical article |
| JPWO2002099513A1 (en) * | 2001-06-01 | 2004-09-16 | 三菱瓦斯化学株式会社 | Plastic molded article having photochromic properties and / or polarization properties |
| EP1162482A3 (en) * | 2000-06-09 | 2004-11-10 | Mitsubishi Gas Chemical Company, Inc. | Synthetic resin laminate having both polarization characteristic and photochromism characteristic |
| WO2006035494A1 (en) * | 2004-09-28 | 2006-04-06 | Yugengaisha Magtec | Polarizing resin lens and process for producing same |
| JP2007178920A (en) * | 2005-12-28 | 2007-07-12 | Daicel Degussa Ltd | Functional optical lens and method for manufacturing same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55121412A (en) * | 1979-03-14 | 1980-09-18 | American Optical Corp | Photochromic plastic lens |
| JPS60112880A (en) * | 1983-11-04 | 1985-06-19 | ピーピージー インダストリーズ インコーポレーテツド | Photochromic compound and product containing same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1186987A (en) | 1967-08-30 | 1970-04-08 | Fuji Photo Film Co Ltd | Photochromic Compounds |
| JPS4948631B1 (en) | 1968-10-28 | 1974-12-23 | ||
| US4215010A (en) | 1978-09-08 | 1980-07-29 | American Optical Corporation | Photochromic compounds |
| US4342668A (en) | 1978-09-08 | 1982-08-03 | American Optical Corporation | Photochromic compounds |
-
1986
- 1986-07-15 JP JP61164812A patent/JPH0666003B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55121412A (en) * | 1979-03-14 | 1980-09-18 | American Optical Corp | Photochromic plastic lens |
| JPS60112880A (en) * | 1983-11-04 | 1985-06-19 | ピーピージー インダストリーズ インコーポレーテツド | Photochromic compound and product containing same |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01170904A (en) * | 1987-12-25 | 1989-07-06 | Toray Ind Inc | Polarizing sheet having photochromic property |
| JPH057681B2 (en) * | 1987-12-25 | 1993-01-29 | Toray Industries | |
| WO1989011673A1 (en) * | 1988-05-17 | 1989-11-30 | Kabushiki Kaisha Biotron | Dimmer lens, dimmer glasses and sun glasses and production of dimmer lens |
| JPH02332U (en) * | 1988-06-14 | 1990-01-05 | ||
| JPH0294115U (en) * | 1988-12-29 | 1990-07-26 | ||
| US6455163B1 (en) | 2000-05-02 | 2002-09-24 | Yamamoto Kogaku Co., Ltd. | Transparent optical article |
| JP2001315241A (en) * | 2000-05-02 | 2001-11-13 | Yamamoto Kogaku Co Ltd | Transparent optical article |
| WO2001084218A1 (en) * | 2000-05-02 | 2001-11-08 | Yamamoto Kogaku Co., Ltd. | Polarizing optical article |
| US6659608B2 (en) | 2000-05-02 | 2003-12-09 | Yamamoto Kogaku Co., Ltd. | Polarizing optical article |
| WO2001084217A1 (en) * | 2000-05-02 | 2001-11-08 | Yamamoto Kogaku Co., Ltd. | Transparent optical article |
| EP1162482A3 (en) * | 2000-06-09 | 2004-11-10 | Mitsubishi Gas Chemical Company, Inc. | Synthetic resin laminate having both polarization characteristic and photochromism characteristic |
| JP4779297B2 (en) * | 2001-06-01 | 2011-09-28 | 三菱瓦斯化学株式会社 | Plastic molded body having photochromic properties and / or polarization properties |
| JPWO2002099513A1 (en) * | 2001-06-01 | 2004-09-16 | 三菱瓦斯化学株式会社 | Plastic molded article having photochromic properties and / or polarization properties |
| WO2006035494A1 (en) * | 2004-09-28 | 2006-04-06 | Yugengaisha Magtec | Polarizing resin lens and process for producing same |
| JPWO2006035494A1 (en) * | 2004-09-28 | 2008-05-15 | 有限会社 マグティク | Polarized resin lens and manufacturing method thereof |
| JP4672669B2 (en) * | 2004-09-28 | 2011-04-20 | 有限会社 マグティク | Manufacturing method of polarizing resin lens |
| US7944637B2 (en) | 2004-09-28 | 2011-05-17 | Yugengaisha Magtec | Polarizing resin lens and process for producing same |
| JP2007178920A (en) * | 2005-12-28 | 2007-07-12 | Daicel Degussa Ltd | Functional optical lens and method for manufacturing same |
| US8703296B2 (en) | 2005-12-28 | 2014-04-22 | Daicel-Evonik Ltd. | Functioning optical lens and production method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0666003B2 (en) | 1994-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7289257B1 (en) | Molded laminate for optical use | |
| US4043637A (en) | Photochromic light valve | |
| KR100738267B1 (en) | Synthetic resin laminate having both polarization characteristic and photochromism characteristic | |
| US20070177100A1 (en) | Photochromic opitcal element | |
| US20080187749A1 (en) | Optical element having light influencing property | |
| JPH0629402B2 (en) | Variable light transmittance article | |
| JPWO2002099513A1 (en) | Plastic molded article having photochromic properties and / or polarization properties | |
| KR100399250B1 (en) | Photochromic power of sunglasses lens for light-polarizing and method of making same | |
| JPH0456285B2 (en) | ||
| JP6570452B2 (en) | Polarizing lens for glasses | |
| CN109648956B (en) | Photochromic material and preparation method and application thereof | |
| JPS6321605A (en) | Optical member made of polarizing resin having dimming action | |
| Gemert | The commercialization of plastic photochromic lenses: a tribute to John Crano | |
| JPH11513055A (en) | Polymeric materials for photochromic applications | |
| WO2020132822A1 (en) | Photochromic lens with laminated film, method for producing a photochromic lens, and a spectacle frame | |
| JP2795352B2 (en) | Polarizing resin optical member having light control action | |
| CN111138701A (en) | Special color-changing polarizing composite film for polarizing glasses arranged between two layers of transparent optical lenses and preparation method thereof | |
| JPS61236521A (en) | Light controlling lens and its production | |
| CN110879479B (en) | Color-changing contact lens | |
| JPS6122327A (en) | Photochromic molding | |
| JPH0323586B2 (en) | ||
| US20060250569A1 (en) | Photochromic eyeglass frames and their method of making | |
| TW201319236A (en) | Photo-chromic contact lens and method of manufacturing thereof | |
| JPS6210603A (en) | Dimming lens and its production | |
| TW201912761A (en) | Photochromic composition, ophthalmic lens and ophthalmic lens manufacturing method |