JP5990579B2 - ナノテクスチャー表面を持つシリコーンヒドロゲルレンズ - Google Patents
ナノテクスチャー表面を持つシリコーンヒドロゲルレンズ Download PDFInfo
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- JP5990579B2 JP5990579B2 JP2014514613A JP2014514613A JP5990579B2 JP 5990579 B2 JP5990579 B2 JP 5990579B2 JP 2014514613 A JP2014514613 A JP 2014514613A JP 2014514613 A JP2014514613 A JP 2014514613A JP 5990579 B2 JP5990579 B2 JP 5990579B2
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- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- KAKFZMMRKBQABS-UHFFFAOYSA-N trimethyl(silyloxysilyloxy)silane Chemical compound C[Si](C)(C)O[SiH2]O[SiH3] KAKFZMMRKBQABS-UHFFFAOYSA-N 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
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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
- G02C7/04—Contact lenses for the eyes
- G02C7/049—Contact lenses having special fitting or structural features achieved by special materials or material structures
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- 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
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00317—Production of lenses with markings or patterns
- B29D11/00326—Production of lenses with markings or patterns having particular surface properties, e.g. a micropattern
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00317—Production of lenses with markings or patterns
- B29D11/00346—Production of lenses with markings or patterns having nanosize structures or features, e.g. fillers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C2202/00—Generic optical aspects applicable to one or more of the subgroups of G02C7/00
- G02C2202/16—Laminated or compound lenses
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- Engineering & Computer Science (AREA)
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- Ophthalmology & Optometry (AREA)
- Health & Medical Sciences (AREA)
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- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nanotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Eyeglasses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Description
1つの態様において、本発明は、ナノテクスチャー表面を有するコンタクトレンズ、好ましくはシリコーンヒドロゲルコンタクトレンズの製造方法を提供する。本発明の方法は、(1)有機系溶媒及び有機系溶媒に溶解したポリマーコーティング材料を包含する、有機系コーティング溶液を提供すること(ここで、ポリマーコーティング材料は、複数の第1の反応性官能基及び複数の親和性基又は残基を含む);(2)コンタクトレンズを有機系コーティング溶液と接触させることにより、コンタクトレンズを膨潤させて、コンタクトレンズ上にポリマーコーティング材料の中間コーティングを形成すること(ここで、コンタクトレンズは、ポリマーコーティング材料を結合するために、コンタクトレンズの表面及び表面近くに、ポリマーコーティング材料の親和性基又は残基と相互作用できる、モノマー単位及び/又は疎水性残基及び/若しくはセグメントを含み、そしてポリマーコーティング材料の平均分子量は、ポリマーコーティング材料が、有機系溶媒により膨潤したコンタクトレンズ中に部分的に浸透することを保証するのに充分に高いものであるように選択される);(3)中間コーティングを表面に有する膨潤コンタクトレンズを水溶液又は好ましくは水と接触させることにより、中間コーティングを表面に有するコンタクトレンズを収縮させて、コンタクトレンズ上にナノテクスチャーを有する下塗りコーティングを形成すること;並びに(4)水溶性かつ架橋性親水性ポリマー材料を複数の第2の反応性官能基と、第1の反応性官能基を介して下塗りコーティングの上に架橋して架橋ポリマーコーティング(下塗りコーティングのナノテクスチャーを維持し、かつコンタクトレンズにナノテクスチャー表面を提供する)を形成することにより、下塗りコーティングのナノテクスチャーを固定すること(ここで、1個の第1の反応性官能基は、1個の第2の反応性官能基と、カップリング剤の存在下又は非存在下で反応することにより、ポリマーコーティング材料と水溶性かつ架橋性親水性ポリマー材料との間に1個の架橋結合を形成することができる)という工程を含む。
ここで本発明の実施態様が詳細に述べられる。本発明において発明の範囲又は本質を逸することなく種々の変形及び変化を加えられることは、当業者には明らかであろう。例えば、1つの実施態様の一部として例証又は記述される特色は、更に別の実施態様を生み出すために別の実施態様に利用できる。即ち、本発明は、このような変形及び変化が添付の請求の範囲及びその均等物の範囲に入るとき、これらを含めるものである。本発明の他の目的、特色及び態様は、以下の詳細な説明に開示されるか、又はそこから明らかである。本考察は、典型的な実施態様の説明に過ぎず、そして本発明のより広い態様を限定するものではないことが当業者によって理解される。
で示される基、スチレニル、又は他のC=C含有基を包含する。
[式中、nは、1〜5の整数であり、そしてR1、R2及びR3は、互いに独立に、C1−C8アルキル又はC1−C8ヒドロキシアルキルである]で示される両性イオン基のことをいう。
で示される正荷電基のことをいう。
[式中、pは、0又は1であり;R3及びR4は、独立に、1〜14個の炭素原子を有するアルキル基、3〜14個の炭素原子を有するシクロアルキル基、5〜12個の環原子を有するアリール基、6〜26個の炭素及び0〜3個の硫黄、窒素及び/又は酸素原子を有するアレーニル基であってよいか、あるいはR3及びR4は、これらが結合している炭素と一緒に、4〜12個の環原子を含有する炭素環を形成することができる]で示される1価ラジカルのことをいう。
D = −n’/(A × dc/dx)
[式中、n’=イオン輸送の速度[mol/分];A=曝露されたレンズの面積[mm2];dc=濃度差[mol/L];dx=レンズの厚さ[mm]]のとおり、フィックの法則を適用することにより求める。
により算出できる。
[式中、Rは、化合物の残りの部分であり、Lは、−NR’−(ここで、R’は、水素、C1−C20非置換又は置換の直鎖又は分岐のアルキル基である)、−S−、又は−OC(=O)−である]に図解されるように反応させることにより、中性のヒドロキシル含有共有結合を形成する。
酸素透過度測定
レンズの見かけの酸素透過度及びレンズ材料の酸素伝達率は、米国特許第5,760,100号及びWintertonらによる論文(The Cornea: Transactions of the World Congress on the Cornea 111 , H.D. Cavanagh Ed., Raven Press: New York1988, pp273-280)(これらは両方とも、その全体が参照により本明細書に組み込まれる)に記載されるものと同様の手法により測定した。酸素フラックス(J)は、Dk1000装置(Applied Design and Development Co., Norcross, GAから入手できる)、又は同様の分析装置を用いて、ウェットセル(即ち、ガス流が約100%相対湿度に維持される)中で34℃で測定した。既知の割合の酸素(例えば、21%)を有する空気流は、約10〜20cm3/分の速度でレンズの片側を通過させ、一方窒素流は、約10〜20cm3/分の速度でレンズの反対側に通した。試料は、試験媒体(即ち、生理食塩水又は蒸留水)中で所定の試験温度で測定前に少なくとも30分間(しかし45分間を超えない)平衡化させた。被覆層として使用される任意の試験媒体は、所定の試験温度で測定前に少なくとも30分間(しかし45分間を超えない)平衡化させた。撹拌モーターの速度は、ステッピングモーター制御器での400±15の表示設定に対応する、1200±50rpmにセットした。系を囲む気圧、P測定値を測定した。試験用に曝露される領域におけるレンズの厚さ(t)は、MitotoyaマイクロメーターVL-50、又は同様の装置で約10箇所を測定し、そして測定値を平均することにより決定した。窒素流中の酸素濃度(即ち、レンズを通過して拡散する酸素)は、DK1000装置を用いて測定した。レンズ材料の見かけの酸素透過度、Dkappは、下記式から求めた:
Dkapp=Jt/(P酸素)
(式中、
J=酸素フラックス[マイクロリットルO2/cm2−分]
P酸素=(P測定値−P水蒸気)=(空気流中O2%)[mmHg]=空気流中の酸素の分圧
P測定値=気圧(mmHg)
P水蒸気=34℃で0mmHg(ドライセル中)(mmHg)
P水蒸気=34℃で40mmHg(ウェットセル中)(mmHg)
t=曝露される試験領域におけるレンズの平均厚さ(mm)
Dkappは、barrerの単位で表される)。
(式中、tは試験レンズの厚さ(即ち、対照レンズも同じ)であり、そしてnは測定した対照レンズの数である)。残存酸素抵抗値Rrをtデータに対してプロットして、式:Y=a+bX(ここで、j番目のレンズでは、Yj=(ΔP/J)jであり、そしてX=tjである)の曲線に当てはめた。残存酸素抵抗、Rrは、aに等しい。
Dkc = t/[(t/Dka)−Rr] (2)
Dka_std = tstd/[(tstd/Dkc)+Rr_std] (3)
透過微分干渉コントラスト(TDIC)法。 コンタクトレンズを、スライドガラス上に載せて、レンズをスライドとガラスカバースリップの間で圧迫することにより平らにした。コンタクトレンズ表面を位置決めして、40×対物レンズを用いて、透過微分干渉コントラスト光学部を持つNikon ME600顕微鏡を用いてレンズを通して焦点を合わせて検査した。得られるTDIC画像を次に、図1に示されるように皺の寄った表面パターンの存在を決定すべく評価した。
末端メタクリレート基を持つ鎖延長ポリジメチルシロキサンビニルマクロマー(CE−PDMSマクロマー)の調製
第1の工程において、α,ω−ビス(2−ヒドロキシエトキシプロピル)−ポリジメチルシロキサン(Mn=2000、Shin-Etsu、KF-6001a)を、α,ω−ビス(2−ヒドロキシエトキシプロピル)−ポリジメチルシロキサン49.85gをジイソシアン酸イソホロン(IPDI)11.1gと無水メチルエチルケトン(MEK)150g中でジラウリン酸ジブチルスズ(DBTDL)0.063gの存在下で反応させることにより、IPDIでキャップした。反応を、40℃で4.5時間保持することにより、IPDI−PDMS−IPDIを形成させた。第2の工程では、α,ω−ビス(2−ヒドロキシエトキシプロピル)−ポリジメチルシロキサン(Mn=3000、Shin-Etsu、KF-6002)164.8g及び無水MEK 50gの混合物を、DBTDL更に0.063gを加えたIPDI−PDMS−IPDI溶液に滴下により加えた。反応器を約40℃で4.5時間維持することにより、HO−PDMS−IPDI−PDMS−IPDI−PDMS−OHを形成させた。次にMEKを減圧下で除去した。第3の工程では、メタクリル酸イソシアナトエチル(IEM)7.77g及びDBTDL更に0.063gの添加により第3の工程で末端ヒドロキシル基をメタクリロイルオキシエチル基でキャップすることにより、IEM−PDMS−IPDI−PDMS−IPDI−PDMS−IEMを形成させた。
KF-6001 240.43gを、撹拌器、温度計、クライオスタット、滴下ロート、及び窒素/真空注入口アダプターを取り付けた1L反応器に加え、次に高真空(2×10−2mBar)の適用により乾燥させた。次に、大気圧の乾燥窒素下で、蒸留MEK 320gを反応器に加え、この混合物を充分に撹拌した。DBTDL 0.235gを反応器に加えた。反応器を45℃まで温めた後、穏やかな撹拌下でIPDI 45.86gを滴下ロートにより10分間かけて反応器に加えた。反応液を60℃で2時間保持した。次に蒸留MEK 452gに溶解したKF-6002 630gを加え、均質な溶液が生成するまで撹拌した。DBTDL 0.235gを加え、乾燥窒素のブランケット下で反応器を一晩約55℃で維持した。翌日、MEKをフラッシュ蒸留により除去した。反応器を冷却し、次にIEM 22.7gを反応器に仕込み、続いてDBTDL約0.235gを仕込んだ。約3時間後、更にIEM3.3gを加え、反応を一晩進行させた。その次の日、反応混合物を約18℃に冷却することにより、末端メタクリレート基を持つCE−PDMSマクロマーを得た。
レンズ配合物の調製
配合物Iを、以下の組成を有するように成分を1−プロパノールに溶解することにより調製した:33重量%の実施例2で調製されたCE−PDMSマクロマー、17重量%のN−[トリス(トリメチルシロキシ)−シリルプロピル]アクリルアミド(TRIS−Am)、24重量%のN,N−ジメチルアクリルアミド(DMA)、0.5重量%のN−(カルボニル−メトキシポリエチレングリコール−2000)−1,2−ジステアロイル−sn−グリセロ−3−ホスホエタノールアミン、ナトリウム塩)(L−PEG)、1.0重量%のDarocur 1173(DC1173)、0.1重量%のビジティント(visitint)(メタクリル酸トリス(トリメチルシロキシ)シリルプロピル、TRIS中の5%銅フタロシアニンの青色色素分散液)、及び24.5重量%の1−プロパノール。
レンズを、米国特許第7,384,590号の図1〜6及び7,387,759号(図1〜6)に示される成形用型と類似した再利用可能な成形用型(石英の雌型半分及びガラスの雄型半分)で、上で調製されるレンズ配合物から注型法により調製した。UV照射源は、約4mW/cm2の強度でWG335+TM297カットオフフィルターを持つHamamatsuランプである。成形用型中のレンズ配合物を、約25秒間UV線で照射した。注型レンズを、メチルエチルケトン(MEK)(又はプロパノール若しくはイソプロパノール)で抽出した。
ポリアクリル酸コーティング溶液(PAA−1)を、約0.1重量%の濃度を有するように、ある量のPAA(M.W.:450kDa、Lubrizol製)を所定容量の1−プロパノールに溶解することにより調製して、ギ酸でpHを約2.5に調整した。
PrOHは100%の1−プロパノールを表す;PBSはリン酸緩衝生理食塩水を表す;MEKはメチルエチルケトンを表す;50/50は50/50の1−PrOH/H2Oの溶媒混合物を表す。
PrOHは100%の1−プロパノールを表す;PBSはリン酸緩衝生理食塩水を表す;MEKはメチルエチルケトンを表す;50/50は50/50の1−PrOH/H2Oの溶媒混合物を表す。
ポリ(アクリルアミド−コ−アクリル酸)部分ナトリウム塩、ポリ(AAm−コ−AA)(90/10)(≒90%固形分、ポリ(AAm−コ−AA)(90/10)、Mw 200,000)をPolysciences, Inc.から購入して、受け取ったまま使用した。PAE(Kymene、NMRで測定すると0.46のアゼチジニウム含量)をAshlandから水溶液として購入して、受け取ったまま使用した。パッケージ内架橋(IPC)生理食塩水は、約0.07%w/wのポリ(AAm−コ−AA)(90/10)及び約0.15%のPAE(約8.8ミリモルの初期アゼチジニウムのミリモル当量)をリン酸緩衝生理食塩水(PBS)(約0.044w/w% NaH2PO4・H2O、約0.388w/w% NaH2PO4・2H2O、約0.79w/w% NaCl)に溶解して、pHを7.2〜7.4に調整することにより調製した。次にIPC生理食塩水を約70℃で約4時間熱前処理した(熱前処理)。この熱前処理中に、ポリ(AAm−コ−AA)及びPAEが相互に部分架橋する(即ち、PAEの全てのアゼチジニウム基を消費しない)ことにより、IPC生理食塩水中に、分岐ポリマーネットワーク内にアゼチジニウム基を含有する水溶性かつ熱架橋性親水性ポリマー材料を形成させた。熱前処理後、IPC生理食塩水を、0.22ミクロンのポリエーテルスルホン[PES]膜フィルターを用いて濾過して、室温まで冷却して戻した。次に10ppmの過酸化水素を最終IPC生理食塩水に加えることにより、バイオバーデン増殖を防ぎ、そしてIPC生理食塩水を、0.22ミクロンのポリエーテルスルホン[PES]膜フィルターを用いて濾過した。
架橋親水性コーティングを表面に、そして約0.95ミクロンの中心厚を有する、得られたSiHyコンタクトレンズは、約142〜約150barrerの酸素透過度(Dkc又は推定固有Dk)、約0.72〜約0.79MPaのバルク弾性係数、約30%〜約33重量%の含水量、約6の相対イオン透過性(Alsaconレンズに比較して)、及び約34〜約47度の接触角を有していた。
実施例4
PAA−Fは、5−アミノフルオレセインをPAA(Mw 450k)に共有結合させることにより社内で合成した。フルオレセインの標識程度は、数%、例えば、約2モル%(又は下に示される式でn/(m+n)=2%)である。
レンズを、実施例3で上で調製したレンズ配合物から、米国特許第7,384,590号の図1〜6及び7,387,759号(図1〜6)に示される成形用型と類似した再利用可能な成形用型(石英の雌型半分及びガラスの雄型半分)で注型法により調製した。成形用型中のレンズ配合物を、約24秒間UV線(13.0mW/cm2)で照射した。
PAA−Fコーティング溶液を、約0.036重量%の濃度を有するように、ある量の上で調製したPAA−Fを所定容量の1−PrOH/水(95/5)に溶解することにより調製して、ギ酸でpHを約2.5に調整した。PAA−Fを溶解するために5%水を使用した。
注型コンタクトレンズを抽出して、以下の一連の浴に浸漬することによってコーティングした:DI水浴(約56秒間);6つのMEK浴(それぞれ約44、56、56、56、56、及び56秒間);DI水浴(約56秒間);1−PrOH/水(95/5)溶媒混合物中のPAA−Fコーティング溶液(約0.036重量%、ギ酸で約pH2.5まで酸性にする)の1つの浴(約44秒間);水/1−プロパノールの50%/50%混合物の1つの浴(約56秒間);4つのDI水浴、それぞれ約56秒間;1つのPBS浴、約56秒間;及び1つのDI水浴、約56秒間。
上で調製したPAA−LbLベースコーティングを表面に有するレンズを、ポリプロピレンのレンズパッケージングシェル(1シェルあたり1個のレンズ)に実施例3に記載される手順により調製されたIPC生理食塩水0.6mL(生理食塩水の半分はレンズを挿入する前に加えた)と一緒に入れた。次にブリスターをアルミ箔で密閉して、約121℃で約30分間オートクレーブ処理することにより、架橋コーティング(PAA−x−親水性ポリマー材料)を表面に持つSiHyコンタクトレンズを形成させた。
架橋コーティング(上で調製)を持つ水和SiHyレンズの横断面を切り出して、2枚のガラスカバースリップの間に挟み、そして共焦点レーザー蛍光顕微鏡(モデル#Zeiss LSM 510 Vis)で画像を収集した。レンズのフロントカーブ側からベースカーブ側まで、又はその逆に走査した。PAA−Fの存在は、緑色の蛍光により示され、そして共焦点レーザー蛍光顕微鏡像を得ることができる。共焦点レーザー蛍光顕微鏡像の検査により、高PAA−F層が両方のレンズ表面(前面及び後面)及び周辺端部に存在し、一方水和レンズ材料の大半にはPAA−Fが観測されないことが明らかになった。
Claims (17)
- ナノテクスチャー表面を有するコンタクトレンズの製造方法であって、
(1)有機系溶媒及び有機系溶媒に溶解したポリマーコーティング材料を包含する、有機系コーティング溶液を提供すること(ここで、ポリマーコーティング材料は、複数の第1の反応性官能基及び複数の親和性基又は残基を含む);
(2)コンタクトレンズを有機系コーティング溶液と接触させることにより、コンタクトレンズを膨潤させて、コンタクトレンズ上にポリマーコーティング材料の中間コーティングを形成すること(ここで、コンタクトレンズは、ポリマーコーティング材料を結合するために、コンタクトレンズの表面及び表面近くに、ポリマーコーティング材料の親和性基又は残基と相互作用できる、モノマー単位及び/又は疎水性残基及び/若しくはセグメントを含み、そしてポリマーコーティング材料の平均分子量は、少なくとも25,000ダルトンである);
(3)中間コーティングを表面に有する膨潤コンタクトレンズを水溶液又は水と接触させることにより、中間コーティングを表面に有するコンタクトレンズを収縮させて、コンタクトレンズ上にナノテクスチャーを有する下塗りコーティングを形成すること;並びに
(4)水溶性かつ架橋性親水性ポリマー材料を複数の第2の反応性官能基と、第1の反応性官能基を介して下塗りコーティングの上に架橋して架橋ポリマーコーティング(下塗りコーティングのナノテクスチャーを維持し、かつコンタクトレンズにナノテクスチャー表面を提供する)を形成することにより、下塗りコーティングのナノテクスチャーを固定すること(ここで、1個の第1の反応性官能基は、1個の第2の反応性官能基と、カップリング剤の存在下又は非存在下で反応することにより、ポリマーコーティング材料と水溶性かつ架橋性親水性ポリマー材料との間に1個の架橋結合を形成することができる)という工程を含む方法。 - 有機系溶媒が、溶媒系であって、1種以上の有機溶媒、及び溶媒系の重量に対して30%以下(重量)の水からなる溶媒系であり、そして1種以上の有機溶媒が、トリプロピレングリコールメチルエーテル、ジプロピレングリコールメチルエーテル、エチレングリコールn−ブチルエーテル、アセトン、メチルエチルケトン、ジエチレングリコールn−ブチルエーテル、ジエチレングリコールメチルエーテル、エチレングリコールフェニルエーテル、プロピレングリコールメチルエーテル、プロピレングリコールメチルエーテルアセテート、ジプロピレングリコールメチルエーテルアセテート、プロピレングリコールn−プロピルエーテル、ジプロピレングリコールn−プロピルエーテル、トリプロピレングリコールn−ブチルエーテル、プロピレングリコールn−ブチルエーテル、ジプロピレングリコールn−ブチルエーテル、トリプロピレングリコールn−ブチルエーテル、プロピレングリコールフェニルエーテル、ジプロピレングリコールジメチルエーテル、ポリエチレングリコール類、ポリプロピレングリコール類、酢酸エチル、酢酸ブチル、酢酸アミル、乳酸メチル、乳酸エチル、乳酸i−プロピル、C1−C12アルコール、1−メチル−2−ピロリドン、N,N−ジメチルプロピオンアミド、ジメチルホルムアミド、ジメチルアセトアミド、ジメチルプロピオンアミド、N−メチルピロリジノン、1,2−プロピレングリコール、200以下の分子量を有するポリエチレングリコール、テトラヒドロフラン、塩化メチレン、及びこれらの混合物よりなる群から選択される、請求項1に記載の方法。
- コンタクトレンズが、有機系コーティング溶液により、少なくとも50%膨潤させられる、請求項1又は2に記載の方法。
- 第1の複数の反応性官能基が、カルボキシル基、アゼチジニウム基、アミノ基、アズラクトン基、イソシアネート基、エポキシ基、アジリジン基、チオール基、ヒドロキシル基、及びこれらの組合せよりなる群から選択され;そして親和性基又は残基が、第1の反応性官能基と同一であるか又は異なるかのいずれかであり、そしてカルボキシル基、アンモニウム基、疎水性残基、疎水性セグメント、及びこれらの組合せよりなる群から選択される、請求項1、2又は3に記載の方法。
- ポリマーコーティング材料が、(1)アンモニウム含有ビニルモノマー又はカルボキシル含有ビニルモノマーのホモポリマー;(2)1種以上のアンモニウム含有及び/又はカルボキシル含有ビニルモノマーのコポリマー;(3)1種以上のアンモニウム含有及び/又はカルボキシル含有ビニルモノマーと非反応性ビニルモノマー[(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N−ビニルピロリドン(NVP)、N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノプロピル(メタ)アクリルアミド、メタクリル酸グリセロール、3−アクリロイルアミノ−1−プロパノール、N−ヒドロキシエチルアクリルアミド、N−[トリス(ヒドロキシメチル)メチル]−アクリルアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、2−ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、1500ダルトン以下の重量平均分子量を有するC1−C4−アルコキシポリエチレングリコール(メタ)アクリレート、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、アリルアルコール、ビニルアルコール(コポリマー中の酢酸ビニルの加水分解形)、ホスホリルコリン含有ビニルモノマー、及びこれらの組合せよりなる群から選択される]との、そして、アゼチジニウム基、アズラクトン基、イソシアネート基、エポキシ基、アジリジン基、及びこれらの組合せよりなる群から選択される反応性官能基を有する、1種以上の反応性ビニルモノマーとのコポリマー;(4)ポリエチレンイミン(PEI);(5)ペンダント第1級及び/又は第2級アミノ基を持つポリビニルアルコール;(6)少なくとも1個の疎水性セグメント並びにアゼチジニウム基、アズラクトン基、イソシアネート基、エポキシ基、アジリジン基、チオール基、及びこれらの組合せよりなる群から選択される反応性官能基を有するポリマーセグメントを包含するブロックコポリマー;あるいは(7)これらの組合せである、請求項1〜4のいずれか1項に記載の方法。
- ポリマーコーティング材料が、少なくとも70モル%のモノマー単位の1種以上のカルボキシル含有ビニルモノマーを含むポリマー又はコポリマーであり、そして1種以上のカルボキシル含有ビニルモノマーが、アクリル酸、メタクリル酸、エチルアクリル酸、プロピルアクリル酸、ブチルアクリル酸、N,N−2−アクリルアミドグリコール酸、β−メチル−アクリル酸、α−フェニルアクリル酸、β−アクリルオキシプロピオン酸、ソルビン酸、アンゲリカ酸、ケイ皮酸、1−カルボキシ−4−フェニルブタジエン−1,3、イタコン酸、シトラコン酸、メサコン酸、グルタコン酸、アコニット酸、マレイン酸、フマル酸、及びこれらの組合せよりなる群から選択される、請求項1〜5のいずれか1項に記載の方法。
- ポリマーコーティング材料が、直鎖又は分岐のポリアクリル酸;直鎖又は分岐のポリメタクリル酸;直鎖又は分岐のポリ(アクリル酸−コ−アクリルアミド)(少なくとも70モル%のアクリル酸を有する);直鎖又は分岐のポリ(メタクリル酸−コ−アクリルアミド)(少なくとも70モル%のメタクリル酸を有する);直鎖又は分岐のポリ(アクリル酸−コ−ビニルピロリドン)(少なくとも70モル%のアクリル酸を有する);直鎖又は分岐のポリ(メタクリル酸−コ−ビニルピロリドン)(少なくとも70モル%のメタクリル酸を有する)である、請求項6に記載の方法。
- コンタクトレンズが、シリコーン含有ビニルモノマー、シリコーン含有ビニルマクロマー、シリコーン含有プレポリマー、親水性ビニルモノマー、疎水性ビニルモノマー、架橋剤、フリーラジカル開始剤、親水性ビニルマクロマー/プレポリマー、UV吸収剤、可視着色剤、抗菌剤、生物活性剤、浸出性潤滑剤、浸出性涙液安定化剤、及びこれらの組合せよりなる群から選択される、少なくとも1種の成分を含むレンズ配合物の重合により得られる、シリコーンヒドロゲルコンタクトレンズである、請求項1〜7のいずれか1項に記載の方法。
- 水溶性かつ架橋性親水性ポリマー材料の第2の反応性官能基が、カルボキシル基、アゼチジニウム基、アミノ基、アズラクトン基、イソシアネート基、エポキシ基、アジリジン基、ヒドロキシル基、チオール基、又はこれらの組合せ(ただし、1個の第2の反応性官能基は、ポリマーコーティング材料の1個の第1の反応性官能基と、カップリング剤の存在下又は非存在下でカップリング反応において反応させて、架橋結合を形成することができる)である、請求項1〜8のいずれか1項に記載の方法。
- 第2の反応性官能基が、熱架橋性基である、請求項1〜9のいずれか1項に記載の方法。
- 水溶性かつ架橋性親水性ポリマー材料が、3次元ネットワーク及びネットワーク内の第2の反応性官能基を含む、部分架橋親水性ポリマー材料である、請求項1〜10のいずれか1項に記載の方法。
- 水溶性かつ架橋性親水性ポリマー材料が、(i)20%〜95%(重量)のエピクロロヒドリン官能化ポリアミン又はポリアミドアミンから誘導された第1のポリマー鎖、(ii)5%〜80%(重量)の、少なくとも1個の反応性官能基(アミノ基、カルボキシル基、チオール基、及びこれらの組合せよりなる群から選択される)を有する少なくとも1種の親水性増強剤から誘導された、親水性残基又は第2のポリマー鎖(ここで、親水性残基又は第2のポリマー鎖は、それぞれエピクロロヒドリン官能化ポリアミン又はポリアミドアミンの1個のアゼチジニウム基と、親水性増強剤の1個のアミノ、カルボキシル又はチオール基との間に形成される、1個以上の共有結合を介して第1のポリマー鎖に共有結合している)、及び(iii)第1のポリマー鎖又は第1のポリマー鎖に共有結合しているペンダント若しくは末端基の一部である、アゼチジニウム基を含む、請求項1〜11のいずれか1項に記載の方法。
- 親水性増強剤が、アミノ−、カルボキシル−又はチオール含有単糖類;アミノ−、カルボキシル−又はチオール含有二糖類;アミノ−、カルボキシル−又はチオール含有オリゴ糖類;あるいはこれらの組合せである、請求項12に記載の方法。
- 親水性増強剤が、カルボキシメチルセルロース(反復単位:−[C6H10−mO5(CH2CO2H)m]−(ここで、mは1〜3である)の組成に基づいて概算して、40%以下のカルボキシル含量を有する);カルボキシエチルセルロース(反復単位:−[C6H10−mO5(C2H4CO2H)m]−(ここで、mは1〜3である)の組成に基づいて概算して、36%以下のカルボキシル含量を有する);カルボキシプロピルセルロース(反復単位:−[C6H10−mO5(C3H6CO2H)m]−(ここで、mは1〜3である)の組成に基づいて概算して、32%以下のカルボキシル含量を有する);ヒアルロン酸(反復単位:−(C13H20O9NCO2H)−の組成に基づいて概算して、11%のカルボキシル含量を有する);コンドロイチン硫酸(反復単位:−(C12H18O13NSCO2H)−の組成に基づいて概算して、9.8%のカルボキシル含量を有する);又はこれらの組合せである、請求項12に記載の方法。
- 親水性増強剤が、PEG−NH2;PEG−SH;PEG−COOH;H2N−PEG−NH2;HOOC−PEG−COOH;HS−PEG−SH;H2N−PEG−COOH;HOOC−PEG−SH;H2N−PEG−SH;1個以上のアミノ、カルボキシル又はチオール基を持つマルチアームPEG;1個以上のアミノ、カルボキシル又はチオール基を持つPEGデンドリマー;アクリルアミド(AAm)、N,N−ジメチルアクリルアミド(DMA)、N−ビニルピロリドン(NVP)、N−ビニル−N−メチルアセトアミド、グリセロール(メタ)アクリレート、ヒドロキシエチル(メタ)アクリレート、N−ヒドロキシエチル(メタ)アクリルアミド、400ダルトン以下の重量平均分子量を有するC1−C4−アルコキシポリエチレングリコール(メタ)アクリレート、ビニルアルコール、N−メチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノプロピル(メタ)アクリルアミド、(メタ)アクリロイルオキシエチルホスホリルコリン、及びこれらの組合せよりなる群から選択される、非反応性親水性ビニルモノマーのモノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のホモ−又はコポリマー;(1)0.1%〜30%(重量)の(メタ)アクリル酸、アリルアミン及び/又はアミノ−C2−C4アルキル(メタ)アクリレート、並びに(2)アクリルアミド、N,N−ジメチルアクリルアミド、N−ビニルピロリドン、(メタ)アクリロイルオキシエチルホスホリルコリン、N−ビニル−N−メチルアセトアミド、グリセロール(メタ)アクリレート、ヒドロキシエチル(メタ)アクリレート、N−ヒドロキシエチル(メタ)アクリルアミド、400ダルトン以下の重量平均分子量を有するC1−C4−アルコキシポリエチレングリコール(メタ)アクリレート、ビニルアルコール、及びこれらの組合せよりなる群から選択される、少なくとも1種の非反応性親水性ビニルモノマーを含む組成物の重合生成物であるコポリマー;あるいはこれらの組合せである、請求項12に記載の方法。
- 親水性増強剤が、PEG−NH2;PEG−SH;PEG−COOH;モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリビニルピロリドン;モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリアクリルアミド;モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ(DMA);モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ(DMA−コ−NVP);モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ(NVP−コ−N,N−ジメチルアミノエチル(メタ)アクリレート);モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ(ビニルアルコール);モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ[(メタ)アクリロイルオキシエチルホスホリルコリン]ホモポリマー又はコポリマー;モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ(NVP−コ−ビニルアルコール);モノアミノ−、モノカルボキシル−、ジアミノ−又はジカルボキシル末端のポリ(DMA−コ−ビニルアルコール);0.1%〜30%(重量)の(メタ)アクリル酸を含むポリ[(メタ)アクリル酸−コ−アクリルアミド];0.1%〜30%(重量)の(メタ)アクリル酸を含むポリ[(メタ)アクリル酸−コ−NVP];(1)(メタ)アクリロイルオキシエチルホスホリルコリン及び(2)0.1%〜30%(重量)の(メタ)アクリル酸、アリルアミン及び/又はアミノ−C2−C4アルキル(メタ)アクリレートを含む組成物の重合生成物であるコポリマー;あるいはこれらの組合せである、請求項12に記載の方法。
- 下塗りコーティングのナノテクスチャーを固定する工程が、ナノテクスチャーを包含する下塗りコーティングを含み、そして密閉レンズパッケージ中の水溶性架橋性親水性ポリマー材料を包含するパッケージング溶液に浸したコンタクトレンズを、118℃〜125℃の温度で20〜90分間オートクレーブ処理することにより実行され、そして水溶性架橋性親水性ポリマー材料の第2の反応性官能基が、アゼチジニウム基及び/又はエポキシ基である、請求項1〜16のいずれか1項に記載の方法。
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-
2012
- 2012-06-07 WO PCT/US2012/041207 patent/WO2012170603A1/en unknown
- 2012-06-07 SG SG2013084348A patent/SG194955A1/en unknown
- 2012-06-07 CN CN201610998845.3A patent/CN106896422B/zh active Active
- 2012-06-07 EP EP12728894.2A patent/EP2718751B1/en active Active
- 2012-06-07 CN CN201280028304.8A patent/CN103597378B/zh active Active
- 2012-06-07 HU HUE12728894A patent/HUE027812T2/en unknown
- 2012-06-07 US US13/490,517 patent/US9244195B2/en active Active
- 2012-06-07 JP JP2014514613A patent/JP5990579B2/ja active Active
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- 2012-06-07 CA CA2838242A patent/CA2838242C/en active Active
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2015
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CA2838242C (en) | 2016-05-17 |
US20120314185A1 (en) | 2012-12-13 |
EP2718751B1 (en) | 2015-07-22 |
CN103597378A (zh) | 2014-02-19 |
EP2718751A1 (en) | 2014-04-16 |
MY163326A (en) | 2017-09-15 |
CN103597378B (zh) | 2017-02-15 |
JP2016218468A (ja) | 2016-12-22 |
WO2012170603A1 (en) | 2012-12-13 |
US9244195B2 (en) | 2016-01-26 |
CA2838242A1 (en) | 2012-12-13 |
HUE027812T2 (en) | 2016-11-28 |
JP2014523542A (ja) | 2014-09-11 |
CN106896422A (zh) | 2017-06-27 |
CN106896422B (zh) | 2021-03-23 |
JP6378268B2 (ja) | 2018-08-22 |
US20160097939A1 (en) | 2016-04-07 |
SG194955A1 (en) | 2013-12-30 |
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