TWI229683B - Hydrogel with internal wetting agent - Google Patents
Hydrogel with internal wetting agent Download PDFInfo
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- TWI229683B TWI229683B TW090106666A TW90106666A TWI229683B TW I229683 B TWI229683 B TW I229683B TW 090106666 A TW090106666 A TW 090106666A TW 90106666 A TW90106666 A TW 90106666A TW I229683 B TWI229683 B TW I229683B
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- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
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- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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Description
!229683 經濟部智慧財產局員工消費合作社印製 五、發明説明(/ ) 本發明係關於一種親水性聚合物,尤指一種當製備 具内部潤濕劑之親水性聚合物時m生物 置,例如眼鏡片。 材料適用於生物醫藥裝置係依一些因子而定,這些 因子包含材料的潤濕性、其枯著性或與其他生物材料例 如蛋白質及脂質之反應特性。在眼科的應用,例如隱形 眼鏡及眼内植入物,氧透性亦為一重要的考量。高氧透 性通常為較佳’因為其具有良好潤濕性及抗粘著或抗生 物材料之反應。 由於具高透氧性的緣故,矽_水凝膠可為一製造生 物醫藥裝置例如隱形眼鏡之特佳材料。然而,其疏水本 性使得由矽酮水凝膠所製之裝置不易潤濕。解決此問題 的方法之一對水凝膠塗佈更多親水性塗層。此增加製造 上的額外複雜度。此外,塗層材料之選用與適當塗層厚 度、塗層一致性及其他可影響生理上表現之因子之二定 一樣困難。 美國專利US Patent 5,219,965及其子案揭示藉由 將具有-疏水部分、-親水部分、一鏈轉移劑及一不飽 和端基之巨分子包含在用以製造聚合物物件之單體混合 物内,以改良聚合物物件例如隱形眼鏡之表面性質。巨 分子可包含具有分子量為50〇_1〇,〇〇〇之聚_N乙烯基吡 咯烷酮,且以1,000-5,000為較佳。巨分子經聚合為水 凝膠且確實可改良聚合物的潤濕性。然而,此種改良通 常無法達到鏡片可從水凝膠製得,而不需親水性塗層之 5 10 15 20 (請先閱讀背面之注意事項存填寫本貢) •装· 訂 1229683 A7
度無响如何,不需鏡片塗層而增進生物醫學裝置(例 如隱形眼鏡)之潤濕性將可視為在技藝中之一顯著的進 步 ° f請先閱讀背面之注意事項再填寫本頁) 美國專利 US Patent 4,045,547 及 4,042,552 揭示聚 5合大置(14·25""35重量%)之聚乙烯基吡咯烷酮^▽?)為_ 聚(曱基丙烯酸羥基乙酯)(HEMA)為基礎之隱形眼鏡的 配方。該聚合反應係在無水分存在下進行。pVp之分 子量則未述及。 美國專利 US Patent 4,833,196 ; 4,791,175 及 10 4,678,838係關於將聚·Ν-乙浠基内醯胺混合於用以製造 隱形眼鏡之聚合物中。聚乙烯基吡咯烷酮(PVP)係為較 佳之聚内醯胺。低分子量(〜4〇,〇〇〇道爾頓)之pvp係與 用以形成鏡片之單體共價鍵結,其係首先藉由與臭氧之 反應使PVP過氧化氫化,接著聚合Pvp與其他單體。 15 美國專利US Patent 5,198,477係在主要由含乙烯 基單體所製之大環物所形成之互穿聚合物網絡中使用低 分子量(〜25,000道爾頓)之PVP。 經濟部智慧財產局員工消費合作社印製 發明摘要 20 本發明關於一種可濕潤之矽酮水凝膠,其係藉由將 一高分子量之親水性聚合物包含於矽酮水凝#單體混合 物内而製得。該親水性聚合物係包覆於介於其與水凝膠 基質間具有少量或無共價鍵之水凝膠中。 在本發明之一方面,高分子量之親水性聚合物係包 25 覆在矽酮水凝膠基質中。 本紙張尺度適用中國國家標準(CNS ) A4規格(21 Οχ 297公釐) 1229683 A/ B7 五、發明説明(3 ) 在本發明之另·方面,古八曰> 1 、 回刀子置之親水性聚合物係 為聚乙稀基17比洛烧嗣。 在本發明之更一方面,离八工曰々^日, 回刀子ΐ之親水性聚合物具 有分子量(Mw)為100,〇〇〇至500 οηΛ、皆说+s ^ ^王)υυ,〇〇〇逗爾頓;較佳為至 5 少約300,000道爾頓。 ★ 在本發明之更一方面,眼於μ於丄j w 敝鏡片係由本發明之石夕嗣水 凝膠所製得。 10 15 經濟部智慧財產局®工消費合作社印製 20 發明詳述 此中所稱”單體,,-言司係為彳聚合之低分子量化合物 (即通常具有低於700之數均分子量),以及為含可進一 步聚合之中至高分子量之化合物或聚合物,有時亦稱為 巨單體(即通常具有大於7〇0之數均分子量)。因此,咸 瞭解”含矽酮單體”及”親水性單體,,一詞包含單體、巨單 體及預聚物。預聚物係為部分聚合之單體或可進一步聚 合之單體。 ’’含矽網單體”係為一在單體、巨分子或預聚物中 含至少二[-Si-O-]重複單元之親水性單體。較佳為存在 於含矽酮單體之總Si及結合〇之數量大於20重量百 分2,較佳為大於30重量百分比之含矽酮單體的總分 子量。本發明較佳之含矽酮單體係具有下列結構: (〒η3)γ 51 | "r ~^—(CH^)p—Si—(:〇SiR52R53R5^ 25 結構
L----.-----10^I— (請先閱讀背面之注意事項再填寫本頁) 、11 f 1229683 A7
五、發明説明(4 ) 10 其中R51為Η或CH3,q為1吱2,曰料— 3 q馮1次2,且對母一 q而言,R52、 及尺為獨立之乙基、甲基、节美、笠其十人 重稷S,-0單元之單價矽氧烷鏈’p為!至i〇n X為0或NR55,其中R55為Η或呈右】φ」加山 r ^ ο. ^ A具有1至4個碳原子 之早k燒基,a為〇或1,且la#杜人ο X 且L為較佳含2至5個碳原 子之雙價鍵合劑’亦可視情況選用包含醚或羥基,例如 聚乙二醇鏈。 可用以形成本發明之矽酮水凝膠之具結構〗之含矽 綱單體為甲基㈣氧丙基雙(三甲切氧基)甲基石夕院, 甲基丙烯氧丙基五甲基二矽氧烷,(3·甲基丙烯氧基·2_ 羥丙氧)丙基雙(三甲基矽氧基)甲基矽烷。較佳之含矽 酮單體為單甲基丙烯氧烷基封端之聚二甲基矽氧烷 (‘mPDMS”),例如示於結構π者·· (請先閱讀背面之注意事項再填寫本頁) 15
SiO- (SiO)
Si-
•R 57 經濟部智慧財產局員工消費合作社印製 其中b=〇至loo 25 ^紙張尺度適用中國國家榡準(CNS ) M規格(21G>< 297趣
結構II 且假使鍵結於Si之位置的r57未具官 20肊丨生,則R”為任一可能含雜原子之c1-1G之脂肪基或 芳香基;具有丁基之C3·8烷基係為較佳,特別是具有 第二丁基者為最佳。Rw為任一單可聚合之乙烯基。其 較佳為一甲基丙烯基部分,但亦可為丙烯基或苯乙烯基 部分或其他類似部分。 較佳為,使額外之含矽酮單體混合於結構I之含石夕 6 1229683 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明説明(女) 酮單體’以形成本發明之軟性隱形眼鏡。 甲基丙烯氧基丙基三(三甲基矽氧基)矽烷(TRIS)、 述於美國專利us 4,711,943之醯胺類似物及述於美國 專利US 5,070,215之乙烯基胺基甲酸酯或碳酸酯類似 5物亦適用於本發明。當然,任一供製造矽酮水凝膠之已 知的含矽酮單體可合併具結構I之含矽酮單體使用,以 形成本發明之軟性隱形眼鏡。依此目的可用於本發明之 許多含矽酮單體則述於1997年10月9日申請之美國專 利申請案序號No· 08/948,128中,在此合併於本案以為 10參考。可合併具結構I之含矽酮單體之其他單體以形成 本發明之矽酮水凝膠的一些實例係為具羥烷胺基官能之 含石夕酮單體,其係述於Vanderlaan等人於1998年3月 2曰申請之美國專利申請案序號No. 09/033,348,標題 為石夕酮水凝膠聚合物,在此合併於本案以為參考。可使 15 用直鏈或具支鏈之羥烷胺基官能之含矽酮單體,係包含 具有下式之後段或無規單體。I μ2 \ R4 R6 Si ——R8p!7 其中, η 為 〇 至 500,且 m 為 〇 至 500,且(n+m)=l〇 至 500, 25更佳為20至250 ; R2、R4、R5、R6及r7為獨立之單價 20 (請先^^背面之注意事項再填寫本頁) m In m mi 1^1 ml in 4 - - 1 ini— 士 .
、1T R1
結構III
Si- 〇 R3
Si Ο 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) • J--—Ί 1229683 A7 五、發明説明 / … 或务基’其可進一步以醇、醋、胺、酮、羧酸或_ 基取8代,較佳為為取代之單價烷基或芳基;且Rl、R3 及R8為獨立之單價烷基或芳基,其可進一 醇、酯、 月’ 、鋼、緩酸或醚基取代,較佳為未經取代之單價烷基 5或方基’或具有以下含氮結構: R9——N;
II
R
10結構IV 饭使R、R及R8至少之一係根據結構IV,其中R9為 雙鍵烧基,例如_(CH2)S·,其中s為1至10 ,較佳為3 15 ,6,且最佳為3 H Rh為獨立之H、單價烧基或 方基,其可進_步以醇、§旨、胺、綱、叛酸或_基取代, 或具有以下結構:
R 12 )R* 16 J5 20
結構V 其中’ R14為Η或單價可聚合基團,係包含丙埽氧基、 甲基丙烯氧基、苯乙烯基、乙烯基、丙烯基或心烯 25基内酿胺’較^^甲,丙婦氧基為η、單價 Τ紙張尺度適用中國國家標準 1229683 A7 經濟部智慧財產局員工消費合作社印製 五、發明説明(γ ) 烷基或芳基,其可進一步以醇、_、胺、酮、羧酸或醚 基或包含丙烯酸、甲基丙烯酸、笨乙烯基、乙烯基、丙 烯基或N-乙烯基内醯胺之可聚合基團取代,較佳為以 醇或甲基丙烯酸取代之烷基。RQ、及Rls為獨立之 5 Η、單價烷基或芳基,其可進一步以醇、酯、胺、酮、 羧酸或醚基取代,或當單體上至少一些結構IV的基團 包含可聚合基團時,R!2及R!5,及R"可相互結合 而形成一環狀結構。R12、R1;及RM較佳為H。 在另一具體實施例中,本發明之矽酮水凝膠亦可包 含親水性單體。視情況可用於製造本發明之水凝膠聚合 物之親水性單體可為任一習知技藝所揭露用以製備水凝 膠之親水性單體。用於本實施例之較佳親水性單體為含 丙烯SiL-或含乙浠基-者。此種親水性單體本身可作為交 聯劑。”心'稀基種類,,或,,含乙烯基,,單體一詞係指含乙烯 基(-CH-CH2)之單體,且通常具高活性。此種親水性含 乙烯基單體已知相當容易聚合。,,丙烯酸種類,,或,,含丙 烯酸”單體一詞係指含丙烯酸基之單體·· (CH2=CRCOX),其中 R 為 Η 或 CH3,且 X 為 〇 或 N, 其亦已知容易聚合例如N,N-二甲基丙烯醯胺(DMA)、 甲基丙烯酸羥乙酯(HEMA)、甲基丙烯酸甘油酯、2-經 乙基甲基丙烯醯胺、單甲基丙烯酸聚乙二醇酯、甲基丙 烯酸及丙烯酸。 可合併於本發明之矽_水凝膠之親水性含乙烯基 單體包含之單體為N-乙烯基内醢胺(例如N_乙烯基吡咯 烷酮(NVP)、N-乙烯基·甲基乙醯胺、N-乙烯基養乙 10 15 20 25 本紙張尺度適用中國國家標準(CNS ) A4規格Y210>^^y t 意 事 項 再 填 寫 本 頁 !229683 A7
請 閱 讀 背 之 注 意 事 項 再 填 本 頁 1229683 A7 五、發明説明(? 用以形成本發明之鏡片的聚合混合物除了 水性單體外,亦包含一或更多高分子量之親水性2 物。親水性聚合物係作為内部潤濕劑。因此,其 ° 所結合之水凝膠’以便大大地改善潤濕性。較佳為滿= 5到-定程度’使得-般供良好生理相容需要疏水塗 疏水性水凝膠可成形,不需塗層仍與例如眼球表面: 好的生理相容性。然而若必要,親水性塗層例如聚丙‘ 酸亦可塗敷於水凝膠表面。當完成時,於其中混合潤濕 劑之水凝膠係藉由降低組織與水凝膠之疏水區間之接觸 而改良水凝膠之生理相容性(相料一㈣時潤 塗層鏡片)。 …Η 可'用於作為内部潤濕劑之親水性聚合物為聚醯 胺、聚内醯胺、聚亞醯胺及聚内醋。其較佳為在水性環 境之氫鍵接受物,對水之氫鍵,因此變得更具親水性。 無娜如何,無水存在下,在親水性水凝膠基質中摻合之 親水性聚合物促進其與疏水性聚合物(例如矽酮)之相容 性。接著與水接觸下(即水合作用),其增進矽酮之可潤 濕性。 這些親水性聚合潤濕劑較佳為在主鏈上結合一環 狀Τ分之線性聚合物。環狀部分更佳為環狀醯胺或亞醯 胺環狀部分。此類聚合物較佳為包含例如聚乙烯基吡咯 烷酮、聚乙烯基咪唑,然而聚合物例如聚二甲基丙烯醯 胺為有效之聚合物。聚乙烯基σ比洛烧酮為最佳之親水性 聚合潤濕劑。 可用於作為本發明之潤濕劑之親水性聚合物具有 ^紙張尺 規格(210χ297二 10 15 20 25 (請先閱讀背面之注意事項再填寫本頁) I229683 A7 經濟部智慧財產今貝工消費合作社印製 五、發明説明(|c?, 高平均分子量(Mw不低於50,000道爾頓,且較佳為 100,000至500,000道爾頓)。更佳之分子量範圍為 300,000 至 400,000,最佳之範圍為 32〇 〇〇〇 至 37〇 〇〇〇。 基於運動黏度量測,親水性聚合物之分子量亦可以所謂 5的K-值表示,如述於E.s· Baraba之聚合物化學及工程 (Encyclopedia of Polymer Science and Engineering)第二 版’第 17 卷,第 198-257 頁,John Wiley & Sons,Inc· 之N-乙烯基醯胺聚合物。以此方式表達,親水性聚合 物之K-值以46至100為較佳。親水性聚合物之用量為 在最終水凝膠配方中存在約1-15重量%之潤濕劑(例如 PVP)。較佳為最終水凝膠配方中存在約3·8重量%之潤 濕劑。此種聚合物當以此令所述之方式製為水凝膠基 貝’則合併於本發明之水凝膠配方,而對水凝膠未有顯 著的共價鍵結。沒有顯著的共價鍵結表示僅可能存在少 里私度的共1貝鍵結,免不了在水凝勝基質中保留濁濕 劑。只要共價鍵可能存在,則其本身不足以在水凝膠基 貝中保留潤濕劑。取而代之為’保持潤濕劑與水凝膠相 關之最顯著的效果為截留。當聚合物在物理上為保留在 水凝膠中時,根據本說明書,聚合物係被,,截留,,。截 留作用係藉由將潤濕劑的聚合物鏈纏繞在水凝膠基質中 而達成。但是,凡得瓦爾力、偶極_偶極交互作用力、 靜電力及氫鍵亦可促進纏繞作用達較小的程度。 本發明之水凝膠較佳係藉由製備一巨分子及聚舍 該巨分子與其他單體混合物之化合物而製得。本說明毫 10 15 20 25 中’’巨分子”一詞係指一藉由使 12 一或 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) (請先閱讀背面之注意事項再填寫本頁}
1229683 A7 經濟部智慧財產局員工消費合作社印製 五、彆明説明(11 ) 多丙烯酸或甲基丙烯酸材料行基團轉移聚合反應(GTP) 而得之預聚物。用於本案之甲基丙烯酸酯或丙烯酸酯可 提供總巨分子配方之羥基部分。因此,甲基丙烯酸甲酯 雖然有利於巨分子總配方不若曱基丙烯酸酯成分,但其 5 本身足以形成本發明之巨分子。但是,其存在及經甲基 丙烯酸將足以作為甲基丙烯酸酯配方。本發明較佳的巨 分子為羥甲基丙烯酸或丙烯酸、三曱基矽氧烷及聚二甲 基矽氧烷之GTP反應產物。更佳為,該巨分子係為甲 基丙烯酸2-羥乙酯(HEMA)、甲基丙烯酸曱酯(MMA)、 甲基丙烯氧基丙基三(三甲基石夕氧基)石夕烧(TRIS)、單甲 基丙烯氧基丙基封端之單丁基封端之聚二甲基矽氧烷 (mPDMS)。較佳為,18-21(甚至更佳為約19.1)莫耳HEM A 係混合约2-3(甚至更佳為約2.8)莫耳MMA、約7-9(甚 至更佳為約7·9)莫耳TRIS及2·5-4·5(甚至更佳為約3·3) 莫耳mPDMS。巨分子之GTP形成係藉由使上述材料之 組合物反應而完成,其,中使用二丁基錫二月桂酸為觸媒 且每莫耳3-異丙烯基-α,α—二甲基节基異氰酸酯加入 2莫耳組合物。上述反應係在約6〇_12〇〇c下進行約 小時。 水凝膠係藉由使以下反應混合物(有時稱為,,單體混 合物)反應而製得··巨分子;含矽酮單體、任意之親水 性聚合物(除潤濕劑以外)交聯劑及高分子量親水性聚合 物(潤濕劑)。單體混合物係在無水下或視需要存在一有 機稀釋劑下反應。水凝膠係藉由該反應混合物之反應產 物的水合作用而完成。較佳為,矽氧烷包含Μ? 9單甲 10 15 20 25 ________ 13 μ氏張尺度適用中酬家標^7^77規格(21 〇 (請先閱讀背面之注意事項再填寫本頁) —0 •項再填· 裝-
、1T - I I · Ϊ229683 五、發明説明(丨工) 基丙烯氧基封端之聚二甲基矽氧烷及三甲基矽氧基矽 =更佳為’單體混合物係包含巨分子、、單甲基丙 、乳基封端之聚二甲基石夕氧炫;甲基丙稀氧基丙基三(三 甲基石夕氧基)石夕烧,” TRIS”;二甲基丙缔醯胺,“DMA” . 甲基丙烯酸經乙醋,” HEMA”;二甲基丙稀酸三乙二醇 酉曰,TEGDMA” ;聚乙稀基吼洛烧嗣,“PVP”,添 加物及光引發劑。 + 混合之含矽酮單體佔反應混合物(單體混合物加上 巨分子)中之反應成分的較佳範圍為從約5至100重量 %,更佳為約· 1〇至90重量%,且最佳為約15至8Q重 量%°倘若本發明視需要選用之親水性單體存在時,則 其:反應混合物中之反應成分的較佳範圍為從約5至 重量%,更佳為約10至60重量%,且最佳為約2〇至Μ 重量%。高分子量親水性聚合物(潤濕劑)佔總反應混合 物之較佳範圍為從約i至15重量%,更佳為約3至Μ 重,且最佳為約5至8重量%。稀釋劑係佔總反應 混合物之較佳範圍為從約〇至7〇重量%,更佳為約〇 至重量%,且最佳為約〇至2〇重量%。所需之稀釋 劑量依反應成分之本性及相對量而定。 更佳為,該反應混合物包含最佳之巨分子(如上所 述);si7.9單甲基丙烯氧基封端之聚二甲基錢燒(〜28 重量%);甲基丙烯氧基丙基三(三甲基矽氧基)矽 烷,”TRIS,,(〜14重量%);二甲基丙稀酿胺,“dma” (〜26重量;甲基丙烯酸羥乙酯,”HEMA”(〜5重量 %);二甲基丙烯酸三乙二j酯’ “TEGDMA”(〜工= 5 10 訂 15 20 25 __ 14 本紙張尺度適用中""國國家標準(CNS ) A4規格(210χ297公着 1229683
量%);聚乙稀基吼略烧嗣,“PVP”(〜5重量%),剩餘 成分包含少量之添加物及光引發劑。該聚合反應最佳係 在20%(全部單體及稀釋劑混合物之重量% (請先閱讀背面之注意事項再填寫本頁) 醇稀釋劑存在下進行。 ’-甲基-3-辛 5 反應混合物中較佳係包含聚合觸媒。聚合觸媒可為 經濟部智慧財產局員工消費合作社印製 一化合物,例如在一般高溫下產生自由基之過氧化月桂 ‘、過氧化苯甲醯、過碳酸異丙酯、偶氮二異丁稀腈等, 或者聚合觸媒可為一光引發劑系統,例如芳香族^ _羥 基酮或第三胺加上二酮。光引發劑系統之實施例為^ 10羥環己基苯基酮、2_羥基-2-甲基-1-苯基-丙-丨_酮、雙(2,6_ 二曱氧苯甲醯)-2,4,4-三甲基苯基氧化膦(DMBAp〇)及一 樟腦醌與4·(Ν,Ν-二甲胺)苯酸乙酯之混合物。該觸媒在 反應混合物中之用量係為催化上有效量,例如每1〇〇份 重之反應單體約〇· 1至約2份。反應混合物之聚合反麻 15之引發可藉由使用適當熱或可見光或紫外光或其他依所 用之聚合反應引發劑而定之裝置。另一替代方式為,引 發作用可完成,不需使用引發劑,例如低電壓電子束。 然而’當使用光引發劑時,較佳的引發劑為丨_經環己 基苯基酮及雙(2,6-二甲氧苯甲醯)-2,4,4-三甲基笨美氧 20化膦(DMBAPO)之混合物,且聚合反應引發作用之最佳 方法為可見光。 通常反應混合物經硬化後,將所生成之聚合物以一 溶劑處理以除去稀釋劑(倘若使用)或任一微量的未反應 成分,同時使聚合物水合以形成水凝膠。所用之溶劑可 25 為水(或水溶液,例如生理食鹽水)或視製造本發明之水 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ297公釐) 1229683 A7 _____B7 五、發明説明(If ) 一~ 凝膠使用之稀釋劑(倘若使用)的溶解度特性,及任一未 (請先閱讀背面之注意事項再填寫本頁) 聚合之單體的溶解度特性而定,最初使用之溶劑可為一 有機液體,例如乙醇、甲醇、異丙醇、其混合物等,或 一或更多此種有機液體與水之混合物,接著以純水(或 5生理食鹽水)萃取,以製造矽酮水凝膠,其中該石夕酮水 凝膠含一以水膨潤之單體的聚合物。經使聚合物水合 後,該矽酮水凝膠含佔矽酮水凝膠總重量1 〇至5 5重量 %水,更佳為2 0至5 0重量。/。水,且最佳為2 5至4 5重 量%水。這些矽酮水凝膠尤適合製造隱形鏡片或眼内透 10 鏡,較佳為軟性隱形鏡片。 参 許多方法已知係於製造隱形鏡片時供反應混合物 成形,包含旋轉鑄造及靜態鑄造。旋轉鑄造法揭露於美 國專利 U.S· Patent Nos· 3,408,429 及 3,660,545,且靜 態鎢造揭露於美國專利U.S. Patent Nos. 4,113 224及 15 4,197,266。用以製造含本發明聚合物之隱形鏡片的較 經濟部智慧財產局員工消費合作社印製 佳方法係藉由直接使秒銅水凝膠成形,其較便宜且能精 密控制水合之鏡片的最終形狀。為了上述目的,將反應 混合物放置於一具有最終所需之%酮水凝膠形狀的塑模 中,藉以製造一具有大約為最終所需產品形狀之聚合 20 物。接著,該聚合物視需要以一溶劑然後水處理,製造 一矽酮水凝膠,該矽酮水凝膠具有大致與最初,成型之聚 合物製品之尺度及形狀相同之最終尺度及形狀。此方法 可用以形成隱形鏡片且進一步述於美國專利U.S. Patent
Nos· 4,495,313 ; 4,889,664 及 5,〇39,549,合併於本案 25 以為參考。經製造矽酮水凝膠後,倘若必要,鏡片可塗 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) 1229683 A7 Β7 經濟部智慧財產局8工消費合作社印製 五、發明説明(|Γ) 佈一親水性塗層。一些加入親水性塗層至鏡片之方法揭 示於習知技藝中,包括美國專利u s Patent 3,854,982, 3,916,033,4,920,184 及 5,002,794 ;世界專利 w〇 91/04283 及歐洲專利 EPO 93810399。 本發明之反應混合物可藉由任一熟習本技藝之人 士已知之方法形成,例如震盪或攪拌,用以形成聚合物 製品或藉由較早揭示之裝置。對一些單體反應混合物而 s,t合反應混合物之溫度較佳係在略大於室溫,例如 30-40 C ’或更高溫如80°C,或低於室溫例如〇_1〇°c, 以避免成分之相分離。 本發明之矽酮水凝膠具高氧透性。其具介於4()及 300 barrer之間的02 Dk值,係由極譜分析法測定。氧 透性之極譜分析法量測如下。將鏡片定位在感應器上, 且Ik後以一網眼支持物覆蓋在上側。滲透過鏡片之氧氣 係使用一由4毫米直徑之金陰極及一銀環陽極組成之極 譜氧氣感應器測得。參考值為使用該方法測量市售之隱 形鏡片。購自Bausch & Lomb之Balaficon A鏡片得到 約79 barrer之測量值。Etafilcon鏡片得到約20至25 barrer之測量值。 5 10 15 20 在實例中使用以下縮寫: TRIS 3_甲基丙烯氧基丙基三(三甲基矽氧基)矽烷
DMA THF TMI HEMA MMA N,N-二甲基丙稀酿胺 四氫呋喃 二甲基間-異丙烯基苄基異氰酸酯 甲基丙烯酸2-羥乙酯 曱基丙烯酸甲酯 本紙ί艮尺度通用中國國家標準(CNS ) A4規格(210χ 297公楚) (請先閱讀背面之注意事項再填寫本頁} I229683 A7 B7 Λ、發明説明(4 ) TB ACB 四丁基鍵-m-氣笨酸醋 mPDMS 800- 1000MW單甲基丙烯氧基丙基封端之 甲基 矽氧烷 3M3P 3-甲基-3-丙醇
Norbloc 2-(2’-經·5-甲基丙烯氧乙基苯基)-2H-苯並三唑 (請先閱讀背面之注意事項再填寫本頁) CGI 1850 ^經環己基苯基嗣與雙(2,6-二甲氧苯甲醯)-2,4,4_ 二甲基本基乳化膦之1:1 (Wgt)摻合物 PVP 聚(N-乙晞基吼洛烧_ ) IPA 異丙醇 實例1(巨分子形成) 經濟部智慧財產局員工消費合作社印製 在14°c、N2氣壓下之於THF之13.75毫升之1M TBACB溶液、30克雙(二甲基胺)甲基矽烷、6139克對 5二甲苯、154J8克甲基丙烯酸甲酯以及於4399.78克THF 之1892.13克甲基丙稀酸2-(三甲基碎氧)乙醋所成之溶 液中,將191.75克1-三曱基矽氧-1-甲氧-2-甲基丙烯加 入。超過260分鐘之期間加入30毫升額外的於THF之 TBACB (0.40M),在此期間使反應為放熱,且接著冷卻 10 至30°C。曱基丙烯酸2-(三甲基矽氧)乙酯加入後60分 鐘,加入467.56克甲基丙烯酸2-(三甲基矽氧)乙酯、 363 6.6克mPDMS及3673.84克TRIS所成之溶液及20.0 克雙(二甲基胺)甲基矽烷,並且使混合物為放熱,且冷 卻至30°C達2小時。接著加入10·0克雙(二甲基胺)甲 15 基矽烷、154.26克甲基丙烯酸甲酯及1892· 13克甲基丙 烯酸2-(三甲基矽氧)乙酯之溶液,且再度使混合物為反 熱。經2小時後,加入2加余無水THF,接著當溶液 冷卻至34°C後,加入43 9.69克水、740.6克甲醇及8.8 克二氣醋酸。使混合物迴流4·5小時,以1 1 〇°c下之油 18 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) 1229683 五、發明説明(l?) A加熱,在135。(:下蒸除揮發物,直到蒸氣溫度n0〇c 達到時,加入曱苯以助水分去除。 將反應燒瓶冷卻至Π 〇 °C,且加入4 4 3克τ ΜI及5 · 7 克二丁基錫之溶液。使混合物反應3·5小時,隨後冷卻 5至3〇t。在減壓下使甲苯蒸發,以產出白色、無水、 蠟質的巨分子。該巨分子之理論〇H含量為169毫莫耳/克。 10 15 2-14 ^ 隱形鏡片係由實例1之巨分子摻合物製得,且其餘 成分如耒1所述,於7(TC可見光下硬化。(除稀釋劑外, 所給予之所有成分量為反應成分之重量%,稀釋劑之給 予里係為隶終單體·稀釋劑摻合物之重量%)。所用之pvf 係為INC生物醫學公司(INC Biomedicals,Inc )所售之,, POLYVINYLPYRROLIDONE (PVP K90),,。經硬化後, 打開鑄模,且將鏡片鬆開放入一 1:1之水與乙醇摻合物 中’隨後於乙醇中清洗以去除任一殘留的單體及稀釋 劑。最後使鏡片在生理硼酸緩衝鹽水中平衡。 (請先閱讀背面之注意事項再填寫本頁) -裝· 經濟部智慧財產局員工消費合作社印製 20 25 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 1229683 A7 --- B7 五、發明說明(I公) 表1:
Ex. 2 Ex, 3 Ex. 4 Ex. 5 Ex. 6 Ex. 7 Ex. 8 Ex. 9 Ex. 10 Ex. 11 Ex. 12 Ex. 13 Ex. 14 巨分子 24 25 25 25 21 25 25 25 25 19 25 25 25 TRIS 20 17 17 18 20 18 19 19.5 19.75 20 17 17 17 DMA 33 32 30 28 28 32 32 32 32 37 30 .30 30 mPDMS 20 17 17 18 20 18 19 19.5 19.75 20 17 17 17 Norbioc 2 2 2 2 2 2 2 2 2 2 2 2 2 CGI 1850 1 1 1 1 1 1 1 1 1 1 1 1 1 PVP 0 6 8 8 8 A 2 1 0.5 1 8 0 8 %稀釋 (3M3P) 20 20 20 20 20 20 20 20 20 20 20 25 30 %EWC1 標準偏差 34.5 50.2 48.6 48.5 46.8 44.1 41.3 38.3 36.0 42.7 48.6 53.0 51.1 0.3 0.3 0.2 0.2 0.3 0.1 0.3 0.2 0.2 0.1 0.2 0.2 0.3 模f 76 59 59 59 49 60 66 77 76 63 59 56 53 標準偏差 4 3 7 11 11 3 4 2 4 3 7 5 A %斷裂4 at 伸長量 332 244 220 261 239 283 295 280 309 325 220 253 264 標準偏差 38 48 71· 48 50 69 35 52 39 22 71 46 41 !bk ec^ 112. 3 76.0 75.9 97.9 107.8 95.8 99.8 92.3 94.1 81.2 75.9 80.5 '39.0 Dk3 139. 8 93.2 99.1 133.3 133.8 123.5 126.0 114.9 114.9 93.3 99.1 102.6 113.0 DCAA 前進 ncj 125 71 58 53 59 55 100 127 117 139 58 61 69 標準偏差 14 18 8 15 8 7 19 17 6 15 8 13 12 揸IS 40 40 40 36 38 45 43 33 46 37 40 38 3 39 5 楳準偏差 脂質吸 7 5 7 5 3 3 6 9 3 7 \標準偏差 7.93 3.55 2.85 3.345 4.165 3.26 4.245 6.405 7.015 5.01 2.85 3.705 2.83 0.46 0.42 0.41 0.11 0.85 0.54 0.355 0.63 0.335 0.2 0.41 0.365 0.24 f青tS賡匕主fe笋負导真窝木頁) 裝--------訂· —.------ 經濟部智慧財產局員工消費合作社印製 20 1. 平衡水含量 2. 氧滲透,邊緣校正’以Barrers計 3. 氧滲透,無邊緣校正’以Barrers計 4. 動接觸角,使用Wilheimy天平以生理硼酸緩衝鹽水測定 25 20 本紙張尺度適用中國國家標準(CNS)M規格⑵G x 297公爱) I229683 經濟部智慧財產局員工消費合作社印製 A7 五、發明說明(丨1 ) 實例15潤濕性
鏡片係由一 8%(以重量計)pVp(得自iNC
Biomedicals,Inc·之 K90)、20%實例 1 之巨分子、28.5% 之 mPDMS、8%之 TRIS、5·0%之 HEMA、26%之 DMA、 5 之 TEGDMA、2·0%之 Norbloc 及 1 ·〇%之 CGI 1850 之摻合物,摻合37.5%(以總單體/稀釋劑摻合物為基 準)3M3P為稀釋劑,接著進行實例2之程序而製得。上 述鏡片進行臨床研究,經配戴後發現具潤濕性且舒適。 以上鏡片(n=10眼)相較於ACUVUE® (n=12眼)歷史對 10照組,發現為1〇0%可潤濕性(配戴時看不到不潤濕點); 關於預鏡片撕裂膜非侵入性撕裂中斷時間(pLTF_NIBUT) 相似,為7·1± 2·7對ACUVUE㊣之12 7± 4·7 ;且舒適度 之 50-點標度為 44·3± 4.5 對 ACUVUE⑧之 46.8± 2.8。 15 f例16(比較)-Κ值29-32 PVP之萃fe 隱形鏡片係依實例2之程序製得,由一 2〇%(以重 量計)40,000 Mw PVP(得自 Sigma Chemicals,平均分子 量為10,000,K值(特性黏度)為29_32)、2〇%實例^之 巨分子、20%之 TRIS、39%之 HEMA、5%之 DMA、3% 20之TEGDMA及1%之DAR0CUR所成之摻合物製得0 摻合50%(以總單體/稀釋劑摻合物為基準)己醇為稀釋 劑’除鏡片不需初萃取而由塑模中取出。每一鏡片妙杆 重並且在5·0毫升之水或曱醇中萃取,分析以時間為1 數之萃取物。於表2中之結果顯示相當低分子量的;νρ 25滲出於甲酵中之聚合物基質。2小時後大約取屮於士 21 j %出所有 I ^--------^--------- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準(CNS)A4規格(210 297公釐) 1229683 經濟部智慧財產局員工消費合作社印製 A7 B7 五、發明說明(Μ ) PVP。然而在水中,PVP未完全從鏡片基質消失。經以 小時後滲透作用停滯,未進一步釋放PVP。 於曱醇中清洗之鏡片放入硼酸緩衝鹽水中。這些鏡 片與硼酸緩衝鹽水之動接觸角為前進104❶及後退41。, 5亦顯不此相當低分子量之pvp未充分保留在聚合物基 質中,以存續醇萃取。 表2-K值29-32PVP之萃取 以聲波萃取PVP(%總詈、* 時間(小時) 於 MeOH 中 於水中 0.25 * 71 14 0.50 78 16 1.00 87 29 1.50 95 35 _ 2.00 93 41 3.00 108 51 __ 18.00 114 72 24.00 114 82 27.50 106 80 43.00 114 79 48.00 1 107 80 *由於正常試驗變異之緣故,值可超過1〇0〇/〇 10 JL例17- K值80-100 PVP之萃取 隱形鏡片係依實例2之程序製得,由一 8%(以重量 什)360,000 Mw PVP(得自 Sigma Chemicals,平均分子量 為360,000,K值(特性黏度)為80-100)、20%實例1之 15 巨分子、35%之 mPDMS、5%之 HEMA、26%之 DMA、 2%之 TEGDMA、2%之 Norbloc 及 2%之 CGI 1850 所成 之摻合物製得,摻合35%(以總單體/稀釋劑摻合物為基 22 本紙張尺度適用j關家標準(CNS)A4規格⑵Q χ 297公髮) 裝--------訂---------線 (請先閱讀背面之注意事項再填寫本頁) 1229683 Λ7 B7 五、發明說明(叫) 準)3M3P為稀釋劑,除鏡片不需初提取而 叩由塑模中取 出。每一鏡片經秤重並且在10.0毫升之水+ π或IPA中萃 取,分析以時間為函數之萃取物。於表3中_ 丁 <多口果顯示 (請先閱讀背面之注意事項再填寫本頁) 即使以強有機溶劑萃取後,較高分子量之PVD丄α \ F V Ρ大部分 5 保留在鏡片中。 表3- Κ值80-100 PVP之萃取 以聲波萃取PVP(%總量)* 時間(小時) 於IPA中 於水中 0.17 14 17 0.33 20 21 0.58 13 21 0.92 20 21 1.08 23 21 1.5 21 22 2.00 22 23 2.50 21 23 3.00 20 23
實例17·粉塵黏荖試驗,可加工之容易I 10 隱形鏡片係由一 5%(以重量計)PVP(得自Sigma
Chemicals,平均分子量為360,000,K值(特性黏度)為 經濟部智慧財產局員工消費合作社印製 80-100)、18%實例 1 之巨分子、28%之 mpDMS、14〇/〇 之 TRIS、5%之 HEMA、26%之 DMA、1%之 TEGDMA、 2%之Norbloc及1%之CGI 1850所成之摻合物製得, 15 摻合20%(以總單體/稀釋劑摻合物為基準)之3,7_二甲基 -3 -辛醇為稀釋劑,接著進行實例2之程序。將鏡片之 一放入一於硼酸緩衝鹽水之家庭粉塵的分散液中,以一 1 〇秒數字摩擦清潔,且在一比較器下檢查。黏在表面 之粉塵量約為25%或低於黏在一同樣處理之無PVP製 23 本紙張尺㈣财關家標準(CNS)A4規格⑵0 X 297公爱) 1229683 A7 B7 ~ " ------ 五、發明說明(^) 造之鏡片。此外’可觀察到含PVP所製之鏡片較其他 鏡片及玻璃與塑膠表面更不黏,故使其在加工過程中t 容易控制。 Γ%先閱讀背面之注音?事項再填寫本頁) -♦裝 訂——.------線泰 經濟部智慧財產局員工消費合作社印製 24 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐)
Claims (1)
- Α8 Β8 C8 D8 修正/受¢7補充· 六、申請專利範圍 專利申請案第90106666號 ROC Patent Appln. No. 90106666 修正之申請專利έ圍中文本一附件一 Amended Claims in Chinese - Encl.m 5 (民國93年5月20曰送呈) (Submitted on May 20, 2004) 1· 一種可潤濕之矽酮水凝膠,其係包含下列成分之反應 10 產物: ' 1 a) —含矽酮巨分子, b) —含矽酮反應混合物;及 c) 一高分子量聚合物,其具有至少50,0〇〇道爾頓之 分子量’相對於矽酮反應混合物所包含之矽酮為 15 親水性,且其選自包含聚醯胺、聚内醯胺、聚亞 醯胺、聚内酯及聚葡聚糖之族群, 其中該親水性聚合物係包覆於該矽酮水凝膠中。 2·如申請專利範圍第1項之水凝膠,其中該親水性聚合 物係為一均聚物。 20 3·如申請專利範圍第1項之水凝膠,其中該親水性聚合 物係為由至少二不同單體之組合物所製之共聚物。 經濟部智慧財產局員工消費合作社印製 4·如申請專利範圍第1項之水凝膠,其中該親水性聚合 物係在主鏈上結合一環狀部。 5. 如申請專利範圍第1項之水凝膠,其中該親水性聚合 25 物係為聚乙烯基吡咯烷酮。 6. 如申請專利範圍第5項之水凝膠,其中該聚乙烯基吡 咯烷酮具有數均分子量大於80,000。 -25 - 本纸張尺度適用巾國國家標準(cnS)A4規格(21〇χ297公爱)9〇l23B1^ 1229683 巧;年 修正 六、申請專利範圍 Α8 Β8 C8 D8 7.如申請專利_第5項之水凝膠,其中該聚乙烯基吼 洛院酮具有數均分子量大於約 100,000 〇 8·種眼鏡片,其係由根據申請專利範圍第1項之可濕 潤之矽酮水凝膠製備。 5 9·如,專職_ 8項之眼鏡片 ’其中具有大量羥基 含里之巨分子包含—部分之單體混合物。 ιο·如申4專则&圍第8項之眼鏡片,其巾該親水性聚合 物係為一均聚物。 11·如申請專韻圍第8項之眼鏡片,其巾該親水性聚合 10 物係為由至少二不同單體之組合物所製之共聚物。 12·如申請專利範圍第8項之眼鏡片,其中該親水性聚合 物係選自包含聚醯胺、聚内醯胺、聚亞醯胺、聚内酯 及聚葡聚糖之族群。 13·如申請專利範圍第12項之眼鏡片,其中該親水性聚合 15 物係為聚乙稀基吼略烧酮。 14·如申請專利範圍第13項之眼鏡片,其中該聚乙烯基吡 洛烧酮具有重均分子量至少為5〇,〇〇〇。 經濟部智慧財產局員工消費合作社印製 15·如申請專利範圍第13項之眼鏡片,其中該聚乙烯基吡 咯烷酮具有重均分子量至少為80,000。 20 16·如申請專利範圍第13項之眼鏡片,其中該聚乙烯基吡 咯烷酮具有重均分子量至少為1〇〇,〇〇〇。 17· —種製造矽酮水凝膠的方法,其係包含: a)混合一石夕酮水凝膠單體混合物與一具有至少 50,000道爾頓分子量之高分子量親水性聚合物以 -26 - 本紙張尺度適用中國國家標準(CNS)A4規格(21〇 X 297公釐) A8 B8 C81229683 形成反應混合物, b) 將該反應混合物置於塑模中,且使該反應混合 物於聚合條件包括熱及/或可見光或紫外光下以 形成具有包覆其中的該親水性聚合物之矽酮水 5 凝膠,及 c) 回收該親水性聚合物包覆其中之矽酮水凝膠。 18·如申請專利範圍第17項之方法,其中該單體混合物具 有大量羥基含量。 19·如申請專利細第17項之方法,其中該親水性聚合物 10 係為一均聚物。 2〇·如申請專利範圍帛17項之方法,其中該親水性聚合物 係為由至少二不同單體之組合物所製之共聚物。 21·如申睛專利範圍帛17項之方法,其中該親水性聚合物 係選自包含聚醯胺、聚内醯胺、聚亞醯胺、聚内醋及 15 聚葡聚糖之族群。 22·如申請專利範圍第21項之方法,其中該親水性聚合物 係為聚乙稀基TJ比Π各烧酮。 經濟部智慧財產局員工消費合作社印製 23·如申請專利範圍第21項之方法,其中該聚乙烯基吡咯 境獅具有重均分子量至少為50,000。 2〇 2屯如申請專利範圍第21項之方法,其中該聚乙烯基吡咯 燒_具有重均分子量至少為8〇,〇〇〇。 25·如申请專利範圍第21項之方法,其中該聚乙烯基π比略 燒_具有重均分子量至少為1〇〇,〇〇〇。 26·二種眼鏡片,係由根據申請專利範圍第17項之方法製 25 得之矽酮水凝膠製備。 _ - 27 讎 本紙張尺度適財國國家標準規格⑵〇 x撕公爱)
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- 2001-03-22 KR KR1020027012414A patent/KR100748379B1/ko active IP Right Grant
- 2001-03-22 JP JP2001569035A patent/JP2003528183A/ja active Pending
- 2001-03-22 WO PCT/US2001/009072 patent/WO2001070837A1/en active IP Right Grant
- 2001-03-22 EP EP10178812.3A patent/EP2258736B1/en not_active Expired - Lifetime
- 2001-03-22 BR BRPI0109443-2 patent/BRPI0109443B8/pt unknown
- 2001-03-22 AU AU4765601A patent/AU4765601A/xx active Pending
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- 2001-03-22 AU AU2001247656A patent/AU2001247656B2/en not_active Expired
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US6367929B1 (en) | 2002-04-09 |
WO2001070837A1 (en) | 2001-09-27 |
AR030691A1 (es) | 2003-09-03 |
CN1217969C (zh) | 2005-09-07 |
EP2258736B1 (en) | 2019-07-31 |
CA2404133A1 (en) | 2001-09-27 |
EP1268590B1 (en) | 2019-08-28 |
EP1268590A1 (en) | 2003-01-02 |
AU4765601A (en) | 2001-10-03 |
BRPI0109443A (pt) | 2004-01-13 |
AU2001247656B2 (en) | 2005-05-26 |
BRPI0109443B8 (pt) | 2021-07-06 |
CN1441814A (zh) | 2003-09-10 |
JP2003528183A (ja) | 2003-09-24 |
KR20030065306A (ko) | 2003-08-06 |
BRPI0109443B1 (pt) | 2013-01-22 |
CA2404133C (en) | 2011-07-05 |
KR100748379B1 (ko) | 2007-08-10 |
EP2258736A1 (en) | 2010-12-08 |
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