JP2012511180A - 疎水性助剤の送達のための肉眼用装置 - Google Patents
疎水性助剤の送達のための肉眼用装置 Download PDFInfo
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- JP2012511180A JP2012511180A JP2011539671A JP2011539671A JP2012511180A JP 2012511180 A JP2012511180 A JP 2012511180A JP 2011539671 A JP2011539671 A JP 2011539671A JP 2011539671 A JP2011539671 A JP 2011539671A JP 2012511180 A JP2012511180 A JP 2012511180A
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- Prior art keywords
- contact lens
- hydrophobic
- lens
- soft
- hydrogel contact
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Abstract
Description
涙膜は、通常、三層構造(脂質層、中間水層、及びムチン層)を含む。脂質層は、最外層であり、マイボーム腺の分泌物から誘導される。それは、二層(水性ムチン相に隣接する薄い極性相、ならびに極性相及び空気界面の両方に会合している厚い非極性相)で構成されているらしい(McCully and Shine, Tr. Am. Soc. Vol. XCV, 1997)。中間水層は、大及び小涙腺(major and minor lacrimal glands)により提供され、水溶性物質を含む。最も内側のムチン相は、糖タンパク質であるムチンで構成され、角膜及び結膜上皮細胞を覆っている。上皮細胞膜は、リポタンパク質で構成されており、そのため一般に疎水性である。涙膜成分のいずれかが欠けると、涙膜が破壊されて、角膜及び結膜上皮にドライスポットが形成される。3種の成分(水層、ムチン層又は脂質層)のいずれかが欠けると、目が乾燥する場合がある。
本発明は、一態様において、ポリマーマトリックスと、そのポリマーマトリックスに共有結合しておらずその内部に分配されている疎水性助剤と、を含むソフトハイドロゲルコンタクトレンズを提供し、そのポリマーマトリックスは、シリコーン含有モノマーもしくはマクロマー及び/又は疎水性モノマーから誘導された疎水性単位と、親水性モノマー又はマクロマーから誘導された親水性単位と、を含み、そのソフトコンタクトレンズは、装用中に疎水性助剤をポリマーマトリックスから装用者の目に徐々に放出する能力を特徴とする。
他に断りがない限り、本明細書で用いられる全ての技術用語及び科学用語は、本発明が属する当該技術分野の当業者に一般に理解されるものと同じ意味を有する。一般に本明細書で用いられる命名法及び実験室手順は、周知であり、当該技術分野で一般に用いられている。当該技術分野及び様々な一般的参考文献の中で提供される方法など、従来の方法が、これらの手順に用いられる。用語が、単数形で示されている場合、本発明人は、その用語の複数も企図する。本明細書で用いられる命名法及び以下に記載される実験室手順は、周知のものであり、当該術分野で一般に用いられている。本開示全体をとおして用いられる以下の用語は、他に断りがない限り、以下の意味を有すると理解されたい。
[(酸素cm3)/(cm2)(秒)(mmHg)]×10−9
と定義される。
[(酸素cm3)(mm)/(cm2)(秒)(mmHg)]×10−10
と定義される。これらは、当該技術分野で一般に用いられる単位である。つまり当該技術分野での使用と一致させるために、単位「バレル」は、先に定義された意味を有する。例えば、90バレルのDk(酸素透過性バレル)及び90ミクロン(0.090mm)の厚さを有するレンズは、100バレル/mmのDk/t(酸素伝達率バレル/mm)を有することになる。本発明によれば、材料又はコンタクトレンズに関する高度の酸素透過性は、100ミクロン厚の試料(フィルム又はレンズ)で測定すると、少なくとも40バレル以上の見かけ上の酸素透過性を特徴とする。
D=−n’/(A×dc/dx)
(式中、n’=イオン輸送率[mol/分];A=暴露されたレンズの面積[mm2];D=イオノフラックス拡散係数[mm2/分];dc=濃度差[mol/L];dx=レンズの厚さ[mm])。約1.5×10−6mm2/分を超えるイオノフラックス拡散係数Dが好ましく、約2.6×10−6mm2/分を超えることがより好ましく、そして約6.4×10−6mm2/分を超えることが最も好ましい。
酸素透過性の測定 レンズの酸素透過性及びレンズ材料の酸素伝達率を、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 York 1988, pp273-280)(両者とも、全体が本明細書に参考として援用されている)に記載のものと類似の技術により測定した。酸素流量(J)を、湿潤(即ち、気流を約100%相対湿度で保持した)セル内で、Dk1000装置(Applied Design and Development Co., Norcross, GAより市販)又は類似の分析装置を使用して34℃で測定した。既知の割合%の酸素(例えば、21%)を有する気流を、レンズの片側に約10〜20cm3/分の速度で透過させる一方、窒素気流をレンズの反対側に約10〜20cm3/分の速度で透過させた。試料を、検査媒体(即ち、生理食塩水又は蒸留水)中で、規定の検査温度で、測定前の少なくとも30分間(但し、45分間未満の間)平衡化した。オーバーレイヤーとして使用した任意の検査媒体を、規定の検査温度で、測定前の少なくとも30分間(但し、45分間未満の間)平衡化した。ステッパ・モータ・コントローラでの表示設定400±15に対応して、撹拌モータの速度を1200±50rpmに設定した。システム周囲の大気圧Pmeasuredを測定した。ミツトヨ(Mitotoya)マイクロメータ VL-50又は同様の装置により約10箇所測定して、測定値の平均をとることにより、検査用に暴露された領域におけるレンズの厚さ(t)を測定した。窒素気流中の酸素濃度(即ち、レンズを通して拡散した酸素)を、Dk1000装置を使用して測定した。レンズ材料の見かけ上の酸素透過性Dkapp(バレル)を、以下の式から測定した:
Dkapp=Jt/(Poxygen)
(式中、J=酸素流量[O2μL/cm2・分];Poxygen=(Pmeasured−Pwater水蒸気)=(気流中のO2%)[mmHg]=気流中の酸素分圧;Pmeasured=大気圧(mmHg);Pwater水蒸気=34℃で0mmHg(乾燥セル内)(mmHg);Pwater水蒸気=34℃で40mmHg(湿潤セル内)(mmHg);t=暴露された検査領域のレンズの平均厚さ(mm))。材料の酸素伝達率(Dk/t)は、酸素透過性(Dkapp)をレンズの平均厚さ(t)で除算することにより計算してもよい。
鎖延長PDMS−ジメタクリラートの合成
第一の工程において、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)49.85gを、ジブチルチンジラウラート(DBTDL)0.063gの存在下、乾燥メチルエチルケトン150g中のイソホロンジイソシアナート(IPDI)11.1gと反応させることにより、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をイソホロンジイソシアナートでキャップした。反応を40℃で4.5時間保持して、IPDI−PDMS−IPDIを形成させた。第二の工程において、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=3000、Shin-Etsu、KF-6002)164.8gと乾燥メチルエチルケトン50gとの混合物を、IPDI−PDMS−IPDI溶液に滴下し、それに更なるDBTDL 0.063gを添加した。反応器を40℃で4.5時間保持して、HO−PDMS−IPDI−PDMS−IPDI−PDMS−OHを形成させた。その後、MEKを減圧下で除去した。第三の工程において、イソシアナトエチルメタクリラート(IEM)7.77g及び更なるDBTDL 0.063gを添加することにより、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して、IEM−PDMS−IPDI−PDMS−IPDI−PDMS−IEMを形成させた。
実施例2で製造されたポリジメチルシロキサンマクロマー31.5重量%;TRIS−アクリルアミド(Shin-Etsu #805001)20.5重量%;DMA(ジメチルアクリルアミド)23重量%;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−2000)0.5重量%;Darocur1173 1.0重量%;Cuフタロシアニン分散液(TRISメタクリラート中の5%)0.1重量%;及び1−プロパノール23.4重量%を混合することにより、レンズ配合剤を調製した。
レンズ(実施例3で製造)を、リン脂質を用いずに調製された表1に示された組成を有する人工涙液(ATF)中で、2種の放出検査のうちの一方に供試した。
この実施例で用いられたDMPCが放射線標識DMPC(C14)であった以外は実施例3に記載された手順により、レンズを製造した。放射線標識DMPCは、New England Nuclear(マサチューセッツ州ウォルサム)により供給された。レンズを1−プロパノール中の放射線標識DMPCの溶液に浸漬することにより、レンズに放射線標識DMPCを付加した。その後、付加されたレンズを、人工涙液(ATF)を放出媒体として用いた放出検査に供試した。ATFの組成を、表2に示す。表1に列挙された成分を、リン酸緩衝生理食塩溶液に溶解して、生理学的に許容しうるpH及びモル浸透圧濃度を提供した。
(1)それまでに放出検査に供試されたレンズを完全に抽出し、その後、溶離液をDMPC含量について分析した。このDMPC量を、放出媒体中で既に定量されたDMPCに数量的に加算した。つまり全DMPC量は、使用寿命全体での量(cradle-to-grave)を表す。
(2)放出検査を受けていない他のレンズも抽出して、初期DMPC含量(レンズ中のDMPCの合計付加量)を測定した。
実施例3に詳述されたとおりに、1,2−ジミリストイル−sn−グリセロ−3−ホスホコリン(DMPC)を0.75重量%の濃度で配合剤に添加して、配合溶媒である1−プロパノールを22.65重量%に低下させて、レンズ配合剤を調製した。レンズの硬化は、実施例3に記載されたとおりであった。
レンズを、実施例3に詳述された方法により製造した。ポリアクリル酸溶液中に浸漬した後、レンズを水で1分間すすぎ、その後、0.10%(重量/容量)〜1.5%の範囲の濃度のビタミンE油を含む1−プロパノール溶液に浸漬した。リン酸緩衝生理食塩水を含むバイアルにレンズを入れて、121℃で30分間オートクレーブ処理した。透過率%の測定から、溶液中の高濃度のビタミンE油に暴露されたそれらのレンズで、透過率の低下が示され、レンズによるビタミンE油の取り込みが示された。
Claims (15)
- ポリマーマトリックスと、前記ポリマーマトリックスに共有結合しておらずその内部に分配されている疎水性助剤と、を含むソフトハイドロゲルコンタクトレンズであって、前記ポリマーマトリックスが、シリコーン含有モノマーもしくはマクロマー及び/又は疎水性モノマーから誘導された疎水性単位と、親水性モノマー又はマクロマーから誘導された親水性単位と、を含み、
前記疎水性助剤が、リン脂質、モノグリセリド、ジグリセリド、トリグリセリド、糖脂質、グリセロ糖脂質、スフィンゴリピド、スフィンゴ糖脂質、脂肪酸、脂肪アルコール、C12−C28鎖長を有する炭化水素、又はそれらの混合物を含み、
前記ソフトコンタクトレンズが、装用中に前記疎水性助剤を前記ポリマーマトリックスから装用者の目に徐々に放出する能力によって特徴付けられる、ソフトハイドロゲルコンタクトレンズ。 - ソフトハイドロゲルコンタクトレンズが、少なくとも約40バレルの酸素透過性、約0.2MPa〜約2.0MPaの弾性係数、少なくとも約1.5×10−6mm2/分のイオノフラックス拡散係数D、約15%〜約70%の水分量、約90°以下の平均水接触角を有することを特徴とする表面親水性、及びそれらの組合わせからなる群から選択される特性を少なくとも1種有する、請求項1記載のソフトハイドロゲルコンタクトレンズ。
- 前記疎水性助剤が、リン脂質である、請求項2記載のソフトハイドロゲルコンタクトレンズ。
- 前記疎水性助剤が、モノグリセリド、ジグリセリド、トリグリセリド、又はそれらの混合物である、請求項2記載のソフトハイドロゲルコンタクトレンズ。
- 前記疎水性助剤が、糖脂質、グリセロ糖脂質、又はそれらの混合物である、請求項2記載のソフトハイドロゲルコンタクトレンズ。
- 前記疎水性助剤が、スフィンゴリピド、スフィンゴ糖脂質、又はそれらの混合物である、請求項2記載のソフトハイドロゲルコンタクトレンズ。
- 前記疎水性助剤が、脂肪酸、脂肪アルコール、C12−C28鎖長を有する炭化水素、又はそれらの混合物である、請求項2記載のソフトハイドロゲルコンタクトレンズ。
- 前記ソフトハイドロゲルコンタクトレンズが、更に、非架橋性親水性ポリマーを浸出性の湿潤剤として含む、請求項2記載のソフトハイドロゲルコンタクトレンズ。
- 前記非架橋性親水性ポリマーが、ポリビニルアルコール;ポリエチレンオキシド;ポリエチレン−ポリプロピレン・ブロック共重合体;ポリアミド;ポリイミド;ポリラクトン;ポリビニルピロリドン;N−ビニルピロリドンと1種以上の親水性ビニルモノマーとの共重合体;アクリルアミド又はメタクリルアミドのホモポリマー;アクリルアミド又はメタクリルアミドと1種以上の親水性ビニルモノマーとの共重合体;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、又はN−ビニル−N−メチルアセトアミドのホモポリマー;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、又はN−ビニル−N−メチルアセトアミドと1種以上の親水性ビニルモノマーとの共重合体、ならびにそれらの混合物である、請求項1〜8のいずれか1項記載のソフトハイドロゲルコンタクトレンズ。
- パッケージ溶液及び請求項1〜9のいずれか1項記載のソフトハイドロゲルコンタクトレンズを含む密閉容器を含む肉眼用製品であって、前記ソフトコンタクトレンズが、前記パッケージ溶液中に少なくとも約1ヶ月間貯蔵した後、少なくとも約4時間にわたり、装用中に前記疎水性助剤を徐々に放出する能力を有する肉眼用製品。
- 前記パッケージ溶液が、増粘性ポリマーを約0.01重量%〜約5重量%含み、前記増粘性ポリマーが、水溶性セルロースエーテル、水溶性ポリビニルアルコール、約2000〜約10,000,000ダルトンの分子量を有するポリ(エチレンオキシド)、約30,000ダルトン〜約1,000,000ダルトンの分子量を有するポリビニルピロリドン、ビニルピロリドンと1種以上の親水性モノマーとの共重合体、又はそれらの混合物である、請求項10記載の肉眼用製品。
- 前記増粘性ポリマーが、メチルセルロース(MC)、エチルセルロース、ヒドロキシメチルセルロース、ヒドロキシエチルセルロース(HEC)、ヒドロキシプロピルセルロース(HPC)、ヒドロキシプロピルメチルセルロース(HPMC)、又はそれらの混合物である、請求項11記載の肉眼用製品。
- 前記増粘性ポリマーが、約30,000ダルトン〜約1,000,000ダルトンの分子量を有するポリビニルピロリドン、ビニルピロリドンと1種以上の親水性モノマーとの共重合体、又はそれらの混合物である、請求項11記載の肉眼用製品。
- コンタクトレンズの装用中に疎水性助剤を徐々に送達することが可能なソフトコンタクトレンズの製造方法であって、
a)疎水性助剤及び水と混和性の有機溶媒を含む溶液に、ソフトハイドロゲルコンタクトレンズを浸漬する工程であって、前記ソフトハイドロゲルコンタクトレンズが、シリコーン含有モノマーもしくはマクロマー及び/又は疎水性モノマーから誘導された疎水性単位と、親水性モノマー又はマクロマーから誘導された親水性単位と、を含むポリマーマトリックスを含み、前記疎水性助剤が、モノグリセリド、ジグリセリド、トリグリセリド、糖脂質、グリセロ糖脂質、スフィンゴリピド、スフィンゴ糖脂質、リン脂質、脂肪酸、脂肪アルコール、C12−C28鎖長を有する炭化水素、鉱物油、シリコーン油、又はそれらの混合物を含み、前記有機溶媒が、ソフトハイドロゲルコンタクトレンズを膨潤させて、前記疎水性助剤を前記ソフトハイドロゲルコンタクトレンズの前記ポリマーマトリックスに浸透させて組み込ませる工程と;
b)内部に分配された前記助剤を有する前記ソフトハイドロゲルコンタクトレンズを、水又は緩衝された水溶液で水和させる工程と;
c)前記水和させたソフトハイドロゲルコンタクトレンズを、レンズパッケージ溶液を含むレンズ容器内に入れて密閉する工程と、を含み、
前記ソフトコンタクトレンズが、装用中に前記疎水性助剤を前記ポリマーマトリックスから装用者の目に徐々に放出する能力を特徴とする方法。 - コンタクトレンズの装用中に疎水性助剤を徐々に送達することが可能なソフトコンタクトレンズを製造する方法であって、
a)第一の有機溶媒、化学線架橋性レンズ形成材料、及び疎水性助剤を含む流体プレポリマー組成物を得る工程であって、前記化学線架橋性レンズ形成材料が、化学線架橋基を含み、そして熱又は化学線により重合して前記ソフトコンタクトレンズのポリマーマトリックスを形成することができ、前記化学線架橋性レンズ形成材料が、モノマー、マクロマー、及び/又はプレポリマーを含み、前記疎水性助剤が、任意の化学線架橋性基を含まず、モノグリセリド、ジグリセリド、トリグリセリド、糖脂質、グリセロ糖脂質、スフィンゴリピド、スフィンゴ糖脂質、リン脂質、脂肪酸、脂肪アルコール、C12−C28鎖長を有する炭化水素、鉱物油、シリコーン油、又はそれらの混合物を含む工程と;
b)一定量の前記流体プレポリマー組成物を、コンタクトレンズを製造するための金型に導入する工程と;
c)前記化学線架橋性プレポリマーを金型内で重合して、前記ポリマーマトリックスに共有結合しておらず実質的に均一な様式でその内部に分布している前記疎水性助剤を含むソフトハイドロゲルコンタクトレズを形成させる工程と;
d)得られた前記ソフトハイドロゲルコンタクトレンズを水又は水溶液で水和させて、第一の有機溶媒を水又はその水溶液と交換する工程と;
e)パッケージ溶液を含む容器内に、前記水和させたコンタクトレンズをパッケージする工程と;
f)前記ソフトコンタクトレンズを容器内で滅菌する工程であって、前記滅菌されたソフトコンタクトレンズが、装用中に前記疎水性助剤を徐々に放出することが可能な工程と、
を含むが、但し、第二の有機溶媒での任意の抽出工程を含まないこと条件とする方法。
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JP2015197479A (ja) * | 2014-03-31 | 2015-11-09 | 株式会社メニコン | 眼科用組成液及びその使用方法 |
JP2023526139A (ja) * | 2020-12-15 | 2023-06-20 | クーパーヴィジョン インターナショナル リミテッド | オレイン酸を放出するコンタクトレンズ |
JP7369878B2 (ja) | 2020-12-15 | 2023-10-26 | クーパーヴィジョン インターナショナル リミテッド | オレイン酸を放出するコンタクトレンズ |
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