JP2016511840A - 色覚異常を矯正するための光学素子 - Google Patents
色覚異常を矯正するための光学素子 Download PDFInfo
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- JP2016511840A JP2016511840A JP2015556110A JP2015556110A JP2016511840A JP 2016511840 A JP2016511840 A JP 2016511840A JP 2015556110 A JP2015556110 A JP 2015556110A JP 2015556110 A JP2015556110 A JP 2015556110A JP 2016511840 A JP2016511840 A JP 2016511840A
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Images
Classifications
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- G02C7/104—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses having spectral characteristics for purposes other than sun-protection
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/024—Methods of designing ophthalmic lenses
- G02C7/027—Methods of designing ophthalmic lenses considering wearer's parameters
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Abstract
Description
R3は、C1〜C6アルキルであり、
R4は、C1〜C6アルキル、エーテル、またはポリエーテルから選択される)
によって表される。
R3は、C1〜C6アルキルであり得、
R4は、C1〜C6アルキル、エーテル、またはポリエーテルから選択され得る)
によって表される、光学素子が提供される。
b2=y2−mx2、
であるはずであり、式中、mは、混同色線(および混同色線に平行な任意の線)の勾配である。
ベンゾトリアゾール(11.91g、100mmol)、1−ヨード−2−メチルプロパン(13.8mL、120mmol)、炭酸カリウム(41.46g、300mmol)、およびジメチルホルムアミド(200mL)の混合物を、アルゴン下で約40℃にて2日間撹拌および加熱した。反応混合物を氷/水(1L)中に注ぎ、トルエン/ヘキサン(2:1、2×500mL)で抽出した。抽出物を1N HCl(2×200mL)で、その後ブライン(100mL)で洗浄し、無水MgSO4で乾燥させ、溶媒を減圧下で除去した。残渣をヘキサン(200mL)でトリチュレートし、室温にて約2時間放置した。沈殿物を分離および廃棄し、溶液をシリカゲル(200g)の層に通して濾過した。シリカゲルをヘキサン/ジクロロメタン/酢酸エチル(37:50:3、2L)で洗浄した。濾液と洗浄液を合わせ、溶媒を減圧下で除去して、2−イソブチル−2H−ベンゾ[d][1,2,3]トリアゾール(化合物1)(8.81g、50%の収率)を油状生成物として得た。
2−イソブチル−2H−ベンゾ[d][1,2,3]トリアゾール(化合物1)(8.80g、50mmol)、臭素(7.7mL、150mmol)、および48% HBr(50mL)の混合物を、HBrトラップと接続された還流冷却器下で約130℃にて約24時間加熱した。反応混合物を氷/水(200mL)中に注ぎ、5N NaOH(100mL)で処理し、ジクロロメタン(2×200mL)で抽出した。抽出物を無水硫酸マグネシウムで脱水し、溶媒を減圧下で除去した。ヘキサン/ジクロロメタン(1:1、200mL)中の残渣の溶液を、シリカゲルの層に通して濾過し、濃縮して、4,7−ジブロモ−2−イソブチル−2H−ベンゾ[d][1,2,3]トリアゾール、化合物2(11.14g、63%の収率)を油状物として得た。これは、室温で貯蔵すると徐々に固化した。
4,7−ジブロモ−2−イソブチル−2H−ベンゾ[d][1,2,3]トリアゾール(化合物2)(17.8g、53mmol)を、予混合した発煙HNO3(7.0mL)およびTFMSA(110g)を約0〜5℃にて少しずつ添加し、約10分後に、反応混合物を油浴中に置き、約55℃にて約8時間加熱し、次いで冷却し、次いで氷/水500mL中に注いだ。得られた固体を水で、その後MeOHで徹底的に洗浄し、真空オーブン内で乾燥させて、7−ジブロモ−2−イソブチル−5,6−ジニトロ−2H−ベンゾ[d][1,2,3]トリアゾール(化合物3)を黄色がかった固体として得た(20.4g、91%)。
4−ブロモトリフェニルアミン(65.0g、200mmol)を、磁気撹拌子、低温温度計、およびアルゴン吸気口を備えた500mlの乾燥した3つ口RBフラスコ内に入れた。テトラヒドロフランを、カニューレ(200ml)を使用して反応フラスコに移し、ドライアイスアセトン浴中で−78℃に冷却し、n−BuLi(ヘキサン中1.6M、130mL)を約30分の期間にわたって滴加した。反応混合物を同じ温度にて約30分にわたって撹拌したままにし、次いで塩化トリブチルスズ(65.0mL)を約30分にわたって滴加した。得られた混合物を一晩撹拌したままにし、室温まで徐々に加温させた。次いでこれを氷冷水(約500mL)中に注ぎ、ジエチルエーテル(2×250mL)で抽出した。有機層をMgSO4で乾燥させ、溶媒を蒸発によって除去して、化合物4 106.5gを1H NMRによって約95%純粋な黄色がかった油状物として得た。
化合物3および4を、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリドの存在下で1:2の比で合わせることによって、化合物5を形成した。無水1,4−ジオキサン100mlを、化合物4(6.80g、12.7mmol)を含有するフラスコに添加し、アルゴンを溶液に通してバブリングさせた。化合物3(2.12g、5mmol)、その後、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド(0.448g、0.640mmol)を添加し、アルゴンをさらに10分間溶液に通して連続してバブリングさせた。次いでフラスコを2時間、約100℃に加熱した。次いで反応混合物を分液漏斗中に注ぎ、ブラインと酢酸エチルの間で分配した。有機層を分離し、濃縮して乾燥させ、次いで最小限のジクロロメタン中に溶解させ、メタノール中に注ぎ、その後沈殿物を濾過し、乾燥させて、化合物5 3.51g(93%)を暗赤色固体として得た。
化合物6のジアミンを、氷酢酸(75ml)中に化合物5(3.51g、4.6mmol)を溶解させ、次いで鉄粉末(2.8g、10当量)を添加することによって調製した。反応器をアルゴンでパージし、次いで約130℃に加熱した。130℃にて3時間後、反応混合物を氷中に注ぎ、黄色沈殿物を真空濾過によって収集した。濾液を水で洗浄し、次いで真空下で乾燥させた。乾燥した生成物を、ジクロロメタン中にこれを溶解させ、シリカゲルのプラグに通して濾過することによってさらに精製した。溶媒を除去した後、化合物6 3.16g(98%)を黄色固体として得た。
化合物6のジアミンを、酢酸の存在下で亜硝酸ナトリウムでこれを処理することによって、化合物7の対応するベンゾトリアゾールに変換した。化合物6(3.03g、4.38mmol)をTHF(20ml)中に溶解させ、氷酢酸(10ml)を添加した。混合物を氷浴中で約0℃に冷却し、水(6ml)中の亜硝酸ナトリウム(0.363g、5.26mmol)の溶液を磁気撹拌しながら滴加した。約10分間撹拌した後、反応器を氷浴から取り出し、室温にてさらに20分間撹拌させた。次いで得られた鮮赤色混合物を分液漏斗中の炭酸水素ナトリウムの溶液中に注ぎ、ジクロロメタンを添加して有機生成物を抽出した。合わせた有機層をブラインで洗浄し、硫酸マグネシウムで乾燥させ、次いで濾過し、濃縮して、化合物7 3g(97%)を赤色固体として得た。
化合物8を、N,N−ジメチルホルムアミド中の塩基性条件下で、化合物7を2−ブトキシエチル4−メチルベンゼンスルホネートと反応させることによって形成した。化合物7(3g)を、丸底フラスコ中でN,N−ジメチルホルムアミドおよび炭酸カリウム(2.4g)と合わせた。DMF中の2−ブトキシエチル4−メチルベンゼンスルホネート(1.5g)の溶液を撹拌溶液に徐々に添加した。混合物を80℃にて3時間撹拌し、次いで冷却させた。これを、水を含有する分液漏斗中に注ぎ、有機生成物をジクロロメタンで抽出した。硫酸マグネシウムで有機部分を乾燥させた後、これを濾過し、真空下で乾燥させた。移動相としてヘキサンおよび酢酸エチルを用いて、Teledyne Isco CombiFlash RF200クロマトグラフィーシステムを使用して、最終生成物を精製した。生成物含有画分をプールし、乾燥させた後、赤色微粉末700mgを収集した。ジクロロメタンおよびメタノールから再結晶によってこの材料をさらに精製して、化合物8(Red−1)600mg(18%)を、LCMSによって98%の純度を有する赤色粉末として得た。
実施例1に従って作製したルミネセント染料、化合物8をさらに抽出または精製することなく使用し、1:1 N−メチルピロリドン:シクロペンタノン中5wt% PVBの溶液と混ぜ、次いでガラス上に2000RPMで約10秒間スピンコートし、その後ホットプレート上で100℃にて約10分間乾燥させた。図6に示した透過率スペクトルが見出された:
したがって、一部の実施形態では、光学素子は、図6に表したものと同様の吸収および/または発光プロファイルを有し得る。例えば、光学素子は、約425nm〜約500nm、約440nm〜約500nm、約450nm、または約530nmの波長を有する光を吸収し得る。一部の実施形態では、光学素子は、約510nm〜約585nm、約515nm〜約575mm、約530nm、または約560nmの波長を有する光を発光し得る。同様に、一部の実施形態では、光学素子は、図7のものに対して透過率スペクトルを有し得る。例えば、光学素子は、約500nm〜約700nm、約510nm〜約550nm、約550nm〜約620nm、または約640nm〜約720nmの波長で透過率ピークを有し得る。一部の実施形態では、ピークの透過率は、約90%、約95%、または約100%超であり得る。
Claims (15)
- R3が、イソプロピルおよびイソブチルから選択される、請求項1または2記載の光学素子。
- R4がR5−O−R6であり、R5およびR6が独立して、C1〜C6アルキルから選択される、請求項1から3のいずれか記載の光学素子。
- ルミネセント化合物が、第1の可視波長で90%超である透過率をもたらすように選択される量で存在する、請求項1から6のいずれか記載の光学素子。
- 膜を備える、請求項1から7のいずれか記載の光学素子。
- レンズを備える、請求項1から8のいずれか記載の光学素子。
- レンズが、コンタクトレンズまたは眼鏡レンズを含む、請求項9記載の光学素子。
- 哺乳動物における視覚不感受性を矯正するための方法であって、
第1の可視色波長と第2の可視色波長との間に視覚不感受性を有する個体を同定することと、
視覚不感受性を矯正する請求項1から10のいずれか記載の光学素子を選択することと、
個体に光学素子を提供するまたは提供するように手配することと
を含む方法。 - 視覚不感受性が、2型3色覚を含む、請求項10記載の方法。
- 色を区別する能力の障害を矯正するためのデバイスであって、
マトリックス材料中に分散したルミネセント化合物を備える光学素子を備え、ルミネセント化合物は、一般式(1):
R3は、C1〜C6アルキルであり、
R4は、C1〜C6アルキル、エーテル、またはポリエーテルから選択される)
によって表され、
光学素子は、人が光学素子を通して見ることを可能にするのに十分に透明であり、
色を区別する能力の障害を有する人が、光学素子を通じて色を含む画像または物体を眺めることによって色をより良好に区別することができるように構成されている、デバイス。 - ルミネセント化合物が、第1の可視色波長と実質的に重なる発光波長および第2の可視色波長と実質的に重なる吸収波長を有する、請求項1から10のいずれか記載の光学素子、または請求項12記載のデバイス。
- ルミネセント化合物が、吸収波長で光を吸収し、発光波長で光を発光し、ヒト錐体光色素が、吸収波長より発光波長に対して実質的に感受性である、請求項1から10のいずれか記載の光学素子、または請求項12記載のデバイス。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2020174950A1 (ja) * | 2019-02-26 | 2020-09-03 | パナソニックIpマネジメント株式会社 | 色覚補正レンズ及び光学部品 |
CN113227886A (zh) * | 2019-02-26 | 2021-08-06 | 松下知识产权经营株式会社 | 色觉矫正透镜以及光学部件 |
JPWO2020174950A1 (ja) * | 2019-02-26 | 2021-09-13 | パナソニックIpマネジメント株式会社 | 色覚補正レンズ及び光学部品 |
JP7329761B2 (ja) | 2019-02-26 | 2023-08-21 | パナソニックIpマネジメント株式会社 | 色覚補正レンズ及び光学部品 |
Also Published As
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EP2951620A1 (en) | 2015-12-09 |
US20160085090A1 (en) | 2016-03-24 |
CN105209936A (zh) | 2015-12-30 |
HK1219310A1 (zh) | 2017-03-31 |
WO2014120809A1 (en) | 2014-08-07 |
CN105209936B (zh) | 2020-01-14 |
JP6738866B2 (ja) | 2020-08-12 |
EP2951620B1 (en) | 2017-03-01 |
US9885883B2 (en) | 2018-02-06 |
JP2018185528A (ja) | 2018-11-22 |
JP6367834B2 (ja) | 2018-08-01 |
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