CN1849531A - 具有蓝光吸收特性的人工晶状体的制备方法 - Google Patents
具有蓝光吸收特性的人工晶状体的制备方法 Download PDFInfo
- Publication number
- CN1849531A CN1849531A CNA2004800257119A CN200480025711A CN1849531A CN 1849531 A CN1849531 A CN 1849531A CN A2004800257119 A CNA2004800257119 A CN A2004800257119A CN 200480025711 A CN200480025711 A CN 200480025711A CN 1849531 A CN1849531 A CN 1849531A
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- China
- Prior art keywords
- methacrylic acid
- phenyl
- ethyl ester
- ester
- absorption
- 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
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Abstract
一种采用光固化来制备能够吸收蓝光和紫外光的人工晶状体的方法。所制备的人工晶状体可阻止蓝光和紫外光到达植入有人工晶状体的眼睛的视网膜。由于所述人工晶状体可阻止蓝光和紫外光到达视网膜,从而能使视网膜免受潜在的危害。
Description
技术领域
本发明涉及具有蓝光吸收特性的人工晶状体的制备方法,更具体地说,本发明涉及在晶状体材料中使用一种或多种在500nm以上具有合适吸收的可见光光引发剂并用可见光源固化晶状体材料来制备人工晶状体的方法。
背景技术
自20世纪40年代,人工晶状体(IOL)植入物形式的光学器件便被用于代替患病或受损的天然晶状体。多数情况下,在手术摘除患病或受损的天然晶状体(如白内障的情况)的同时,人工晶状体被植入眼内。几十年来,刚性的玻璃状聚合物—聚甲基丙烯酸甲酯一直是制造这种人工晶状体植入物的优选材料。
近年来,较柔软、柔韧的人工晶状体植入物因具有可被压缩、折叠、卷曲及其他形变的性能而受到欢迎。这种更柔软的人工晶状体植入物可在嵌入(insertion)眼角膜切口内之前变形。在将IOL嵌入眼内后,由于这种柔软的材料具有弹性复原性,IOL可以恢复到起初未变形的形状。如上所述,较柔软、柔韧的IOL植入物可以通过比刚性IOL所需的5.5-7.0mm更小的眼角膜切口植入眼内,即可以小于4.0mm。由于晶体必须通过角膜上的切口嵌入眼内,因此植入刚性较强的IOL植入物需要较大的切口,通常比非柔韧IOL光学部分的直径稍大。相应地,刚性较强的IOL植入物在市场上变得不受欢迎,主要由于发现大的切口与术后并发症(例如诱导性散光)的发生率的增加相关联。
随着近来白内障小切口手术的改进,人们越来越重视开发适于人造IOL植入物应用的可折叠的柔软材料。Mazzocco(美国专利US4573998)揭示了可以卷曲、折叠或拉伸以通过相对小的切口的可变形晶状体植入物。该可变形晶状体在扭曲状态下被嵌入眼内,然后在眼腔内释放开,由于镜片的弹性使其恢复它的压模形状(molded shape)。Mazzocco揭示了适于用作这种可变形镜片的材料包括聚氨酯弹性体、硅树脂弹性体、水凝胶聚合体化合物(hydrogel polymercompounds)、有机或合成凝胶化合物以及它们的组合。
近年,已经认识到蓝光(400-500mm)对视网膜具有潜在的损害。相应地,结合紫外光吸收体,可以阻止蓝光的黄色染料被应用于可折叠的人工晶状体以避免潜在的损害影响。授予Freeman等人的美国专利US 6353069揭示了含有两种或多种具有芳香基团的丙烯酸酯和/或甲基丙烯酸酯单体的高折射率共聚物。由这些共聚物制成的眼科器件可以含有有色染料,例如美国专利US 5470932揭示的黄色染料。这样的材料表现出足够的强度,使得由其制成的器件,例如人工晶状体,可被折叠或操作,但不破裂。
由于含有蓝光和紫外光吸收体的人工晶状体材料在紫外光及蓝光范围内具有强裂的光吸收,因此很难用传统的光固化引发剂固化所述人工晶状体材料。大多数光引发剂在450nm以上是惰性的。因此,含有蓝光吸收体的人工晶状体材料一般通过热固化制备。热固化一般耗时较长,因此比人工晶状体材料的光固化经济性更低。此外,如果用塑料模具浇铸晶状体,由于模具在热固化过程中变形而使精度不容易控制。
发明内容
按照本发明,能吸收蓝光和紫外光的、柔软可折叠的高折射率人工晶状体是通过使用在500nm以上的具有合适吸收的可见光光引发剂使得能够用可见光源进行固化的固化方法制备的。根据本发明所制备的能吸收蓝光和紫外光的人工晶状体可保护眼睛的视网膜免受蓝光和紫外光的潜在危害,因此可能避免黄斑病变(maculardegeneration)。
本发明中吸收蓝光和紫外光的人工晶状体是用含有烯属不饱和基团的材料例如丙烯酸酯、甲基丙烯酸酯等制备的。合适的材料还含有一种或多种高折射率单体、一种或多种吸收蓝光的部分、一种或多种吸收紫外光的部分,和一种或多种在500nm以上具有合适吸收的光引发剂。
因此,本发明的一个目的是提供具有蓝光吸收特性的人工晶状体的制备方法。
本发明的另一个目的是提供具有相对较高折射率和良好透明性的人工晶状体的制备方法。
本发明的再一个目的是提供具有韧性的人工晶状体的制备方法。
本发明的又一个目的是提供具有生物适应性的可吸收蓝光的人工晶状体。
通过下面的具体描述和权利要求,本发明的上述和其他目的及优点将变得更加明显,其中一些目的和优点将特别描述,另外一些则不进行特别描述。
附图说明
图1显示了光引发剂Irgacure-784TM(Ciba Specialty Chemical,Hawthome,纽约)的0.1%甲醇溶液的紫外-可见(UV-VIS)光谱。
具体实施方式
本发明涉及具有蓝光吸收特性,以便阻止蓝光到达植有人工晶状体的眼睛的视网膜的高折射率人工晶状体的新的制备方法。所述方法通过光固化制备具有蓝光和紫外光吸收能力的人工晶状体。本发明的人工晶状体材料含有在500nm以上具有合适吸收的可见光光引发剂,以便使用可见光源(例如氙灯)使所述材料在相对短的时间内能够固化,优选小于几个小时。根据本发明制备的吸收蓝光和紫外光的人工晶状体保护眼睛的视网膜免受蓝光和紫外光的潜在危害,从而可以避免黄斑病变。
本发明的人工晶状体是用含有烯属不饱和基团(例如丙烯酸酯、甲基丙烯酸酯等)的一种或多种的单体和/或预聚物制备的。
根据本发明,合适的人工晶状体材料还包括一种或多种具有高折射率的单体和/或预聚物。具有高折射率的合适单体包括但不限于那些含有各种芳香基部分的单体。高折射率单体包括但不限于甲基丙烯酸-2-乙基苯氧基酯、丙烯酸-2-乙基苯氧基酯、甲基丙烯酸-2-乙基噻吩酯、丙烯酸-2-乙基噻吩酯、甲基丙烯酸-2-乙基氨基苯酯、丙烯酸-2-乙基氨基苯酯、甲基丙烯酸苯酯、甲基丙烯酸苄酯、甲基丙烯酸-2-苯基乙酯、甲基丙烯酸-3-苯基丙酯、甲基丙烯酸-4-苯基丁酯、甲基丙烯酸-4-甲基苯酯、甲基丙烯酸-4-甲基苄酯、甲基丙烯酸-2,2-甲基苯基乙酯、甲基丙烯酸-2,3-甲基苯基乙酯、甲基丙烯酸-2,4-甲基苯基乙酯、甲基丙烯酸-2-(4-丙基苯基)乙酯、甲基丙烯酸-2-(4-(1-甲基乙基)苯基)乙酯、甲基丙烯酸-2-(4-甲氧基苯基)乙酯、甲基丙烯酸-2-(4-环己基苯基)乙酯、甲基丙烯酸-2-(2-氯苯基)乙酯、甲基丙烯酸-2-(3-氯苯基)乙酯、甲基丙烯酸-2-(4-氯苯基)乙酯、甲基丙烯酸-2-(4-溴苯基)乙酯、甲基丙烯酸-2-(3-苯基苯基)乙酯、甲基丙烯酸-2-(4-苯基苯基)乙酯和甲基丙烯酸-2-(4-苄基苯基)乙酯等。
适合用于本发明的高折射率预聚物包括但不限于丙烯酸酯封端的聚硅氧烷预聚物和甲基丙烯酸酯封端的聚硅氧烷预聚物,其中所述预聚物含有适量的芳香部分以便使预聚物的折射率至少为1.42。优选地,所述预聚物的每个聚硅氧烷单元平均分子量大约在1000~10000,并且预聚物的分子量大约高于1000,但是低于300000。
按照本发明,合适的人工晶状体材料还含有吸收蓝光的部分。典型的吸收蓝光的部分是活性黄色染料,例如偶氮基黄色染料。这样的吸收蓝光的部分包括但不限于D.L.Jinkerson在美国专利US 5662707中公开的那些,以及在其相应的在审申请中公开的那些。上述文献在此一并引入作为参考。
按照本发明,合适的人工晶状体材料还含有吸收紫外光的部分。合适的紫外光吸收体包括但不限于丙烯酸-β-(4-苯并三唑基-3-羟基苯氧基)乙酯、4-(2-丙烯酰氧基乙氧基)-2-羟基二苯酮、4-甲基丙烯酰氧基-2-羟基二苯酮、2-(2’-甲基丙烯酰氧基-5’-甲基苯基)苯并三唑、2-(2’-羟基-5’-甲基丙烯酰氧基乙基苯基)-2H-苯并三唑、2-[3’-叔丁基-2’-羟基-5’-(3”-甲基丙烯酰氧基丙基)苯基]-5-氯苯并三唑、2-[3’-叔丁基-5’-(3”-二甲基乙烯基甲硅烷基丙氧基)-2’-羟基苯基]-5-甲氧基苯并三唑和2-[3’-叔丁基-2’-羟基-5’-(3”-甲基丙烯酰氧基丙氧基)苯基]-5-氯苯并三唑。
按照本发明,合适的人工晶状体材料还含有在500nm以上具有合适吸收的光引发剂。合适的光引发剂包括但不限于取代的光引发剂、共轭的酮类、三嗪基衍生物、金属盐等。用在本发明中的特别优选的一类的光引发剂为二茂钛衍生物,该引发剂暴露于光源下能直接被光解。所述二茂钛衍生物例如Irgacure-784TM(Ciba SpecialtyChemical,Hawthorne,纽约),其UV-VIS谱见图1。Irgacure-784是氟化二苯基二茂钛,其具有下述式1中所描述的结构。
式1
为了使含有黄色染料的制剂在可见光下有效聚合,光源应有足够的瓦特数和在450nm以上具有足够的光发射强度。用于本发明的优选的光源是高强度氙灯,例如但不限于脉冲灯Lamp Model RC-257,该脉冲灯可从麻萨诸塞州Woburn地区的Xenon Corporation购买。Lamp Model RC-257可提供足够使含有黄色染料的制剂有效聚合的瓦特数和足够的450nm以上的光发射强度。使用这样的高强度氙灯可使固化在少于4小时的时间内完成,优选少于1小时,甚至更优选少于30分钟,具体取决于所使用的强度。
本发明中具有蓝光和紫外光吸收能力和高折射率的可折叠的人工晶状体的制备方法将在下边的实施例中进行更详细的描述。
实施例1 N,N-双-(2-羟乙基)-(4-苯偶氮基)苯胺的合成(SolventYellow 58)
通过苯胺的重氮盐与N-苯基二乙醇胺偶联来实施N,N-双-(2-羟乙基)-(4-苯偶氮基)苯胺的合成。在授予D.L.Jinkerson在美国专利US5470932中公开了合成N,N-双-(2-羟乙基)-(4-苯偶氮基)苯胺的详细步骤。
实施例2 N,N-双-(2-丙烯酰氧基乙基)-(4’-苯偶氮基)苯胺的合成
向与回流冷凝器和干燥管相连接的1000ml三颈圆底烧瓶中添加250ml二氯甲烷、5.7g(0.02mol)N,N-双-(2-羟乙基)-(4-苯偶氮基)苯胺。将烧瓶内物质用冰浴冷却。将7.24g(0.04mol)烯丙酰氯通过滴液漏斗滴加至烧瓶内,滴加30分钟。然后将冰浴移走,彻夜连续搅拌反应物。混合物经过滤后用旋转蒸发仪将其浓缩。高效液相色谱(HPLC)分析表明只有一种主产物生成。然后将产物通过硅胶色谱柱以便得到最终纯化的产物,产率至少为80%。将产物用核磁共振(NMR)和质谱鉴定。
实施例3 羟丁基封端的二甲基硅氧烷和二苯基硅氧烷的制备(苯基的含量为25%)
将33.70g(0.118mol)的1,3-双(羟丁基)四甲基二硅氧烷、403.18g(3.25mol)的二甲基二甲氧基硅烷和272.3g(1.08mol)的二苯基二甲氧基硅烷加至1L的圆底烧瓶中。然后将78.29g水和11.9ml浓盐酸缓慢加至烧瓶中。将烧瓶内的反应物回流1小时,从反应物中蒸馏出253.3ml甲醇。将160ml水和130ml浓盐酸加至烧瓶中,反应物回流1小时。然后将烧瓶内的反应物倒入分液漏斗。分离出硅树脂层,并用500ml的醚稀释后用250ml水洗涤一次,用250ml5%的碳酸氢钠水溶液洗涤两次,再用250ml水洗涤两次。最终的有机层用硫酸镁干燥,然后在80℃下抽真空(0.01mmHg)得到粗产品。将粗产品在50∶50的环己胺/二氯甲烷中溶解,然后通过装有同样组成的溶剂混合物的硅胶柱。将四氢呋喃(THF)通过硅胶柱,从而将最终产品收集在THF中。THF馏分合并后干燥、抽真空得到最终产品。最终产品的尺寸排阻色谱(SEC)测量表明环状化合物含量低于3%,滴定法测得分子量为2821。
实施例4 甲基丙烯酸酯封端的、含有二甲基硅氧烷和二苯基硅氧烷单元的聚硅氧烷预聚物的制备
向安装有回流冷凝器和氮气保护的500ml圆底烧瓶中添加5.031g(0.0227mol)的异佛尔酮二异氰酸酯、51.4465g(0.0189mol)的实施例3中的羟丁基封端的二甲基硅氧烷与二苯基硅氧烷共聚物、0.1811g二丁锡二月桂酸酯和150ml二氯甲烷。将烧瓶内反应物回流。回流近90小时后,发现异氰酸酯含量已降至原来的16.2%(理论值为16.7%)。将烧瓶内的反应物冷却至室温。将1.1572g的HEMA和5.7mg的1,1’-2-双-萘酚加至烧瓶内并搅拌。7天后,NCO峰从IR谱图上消失,反应到达终点。除去溶剂后得到定量产率的产物。
实施例5 可用于IOL的、含有黄色染料部分和紫外光吸收体的高折射率水凝胶的制备
制剂由50份实施例5中的预聚物、20份丙烯酸苄基酯、10份甲基丙烯酸苄基酯、20份N,N-二甲基丙烯酰胺、0.25份甲基丙烯酸苯并三唑酯、0.2份的实施例2中所描述的N,N-双-(2-丙烯酰氧基乙基)-(4’-苯偶氮基)苯胺和1份Irgacure-784组成。该混合物在高强度可见光灯即Lamp ModelRC-257下,在两个经硅烷处理过的玻璃盘之间固化1小时。然后将固化后的膜在异丙醇中释放(release)、浸提4小时以上,在70℃的真空干燥箱中彻夜干燥。然后在表征前将干燥后的膜彻夜放置在硼酸盐缓冲液中。该膜的厚度为170~200μm。然后测量水凝胶膜的UV-VIS吸收,在400nm以下透射率小于1%,在450nm以下透射率小于60%但是大于40%。所制备的膜的机械性能可通过调整用于固化的光强度来调整。
通过本发明方法可合成出具有蓝光吸收特性和相对高折射率(大约为1.42或者更高)、相对高的伸长率(大约为100%或者更高)的柔软可折叠的人工晶状体。如本申请所述制得的硅树脂IOL具有所要求的韧性,允许被折叠或变形以通过尽可能小即3.5mm或更小的手术切口嵌入眼内。出人意料的是,在此描述的本发明IOL具有在此所述的理想的物理性能。本发明IOL的这些理想的物理性能之所以出人意料,是因为以前很难将其与蓝光吸收和紫外光吸收材料的光固化联系起来。
采用本发明方法制得的IOL,可以进行卷曲或折叠的任何设计,以便可以通过相对较小的(3.5mm或更小)手术切口进行移植。这样的IOL可以被制造成具有由相同或不同材料制成的光学部分和触觉部分。一旦材料被选定,就可以将其放入具有所需形状的模具中模塑、固化,然后从模具中取出。这样模塑后,根据本发明方法对IOL进行处理,然后用本领域技术人员公知的常规方法对其进行清洁、抛光、包装和消毒。或者,材料可以被浇铸成棒、切成圆片和车成本领域技术人员公知的所需形状。
除了IOL,本发明方法也适合用于制备其它医疗或眼科装置,例如接触镜、人工角膜移植物(keratoprotheses)、囊膜伸缩环(capsular bagextension rings)、角膜潜入体、角膜环等。
采用本发明方法制备的IOL通常在眼科领域应用。例如,在白内障手术过程中,通过在眼角膜上设置的一个小切口将发生白内障病变的天然晶体取出(无晶状体应用(aphakic application)),在切口缝合前,将IOL嵌入前室和后室或晶体囊(lens capsule)。然而这种眼科器件同样也可以在眼科领域技术人员已知的其它手术过程中使用。
虽然这里说明并描述了制备可吸收蓝光的硅树脂IOL的方法,但很显然,对本领域技术人员来说,在不背离本发明精神和范围的情况下可以进行各式各样的修改。本发明的精神和范围由所附的权利要求限定,而不限于在此说明和描述的具体方法和结构。
权利要求书
(按照条约第19条的修改)
用修改后的权利要求书第1页代替原权利要求书第1页,其中修改涉及用新的权利要求1和2代替原权利要求1和2。
1.一种制备医疗器件的方法,该方法包括:
将一种或多种在500nm以上有吸收的光引发剂掺入到含有一种或多种蓝光吸收部分和一种或多种紫外光吸收部分的合适的材料中,其中所述光引发剂能够在波长大于约500nm的可见光辐射下引发所述合适的材料的聚合;和将所述材料在相对短的时间内暴露于可见光下。
2.一种制备具有蓝光和紫外光吸收特性的医疗器件的方法,该方法包括:
将一种或多种在500nm以上有吸收的光引发剂掺入到含有一种或多种蓝光吸收部分和一种或多种紫外光吸收部分的合适的材料中,其中所述光引发剂能够在波长大于约500nm的可见光辐射下引发所述合适的材料的聚合;和将所述材料在相对短的时间内暴露于可见光下。
3.权利要求1或2的方法,其中所述医疗器件选自接触镜、人工角膜移植物、囊膜伸缩环、角膜嵌入物及角膜环。
4.权利要求1或2的方法,其中所述医疗器件是人工晶状体。
5.权利要求1或2的方法,其中所述蓝光吸收部分是一种或多种活性黄色染料。
6.权利要求1或2的方法,其中所述蓝光吸收部分是一种或多种偶氮基黄色染料。
7.权利要求1或2的方法,其中所述合适的材料是具有烯属不饱和基团的材料。
Claims (22)
1.一种制备医疗器件的方法,该方法包括:
将一种或多种在500nm以上有吸收的光引发剂掺入到含有一种或多种蓝光吸收部分和一种或多种紫外光吸收部分的合适的材料中;
和将所述材料在相对短的时间内暴露于可见光下。
2.一种制备具有蓝光和紫外光吸收特性的医疗器件的方法,该方法包括:
将一种或多种在500nm以上有吸收的光引发剂掺入到含有一种或多种蓝光吸收部分和一种或多种紫外光吸收部分的合适的材料中;
和将所述材料在相对短的时间内暴露于可见光下。
3.权利要求1或2的方法,其中所述医疗器件选自接触镜、人工角膜移植物、囊膜伸缩环、角膜嵌入物及角膜环。
4.权利要求1或2的方法,其中所述医疗器件是人工晶状体。
5.权利要求1或2的方法,其中所述蓝光吸收部分是一种或多种活性黄色染料。
6.权利要求1或2的方法,其中所述蓝光吸收部分是一种或多种偶氮基黄色染料。
7.权利要求1或2的方法,其中所述合适的材料是具有烯属不饱和基团的材料。
8.权利要求1或2的方法,其中所述合适的材料是丙烯酸酯或者甲基丙烯酸酯。
9.权利要求1或2的方法,其中所述合适的材料包括一种或多种高折射率单体。
10.权利要求1或2的方法,其中所述合适的材料包括一种或多种高折射率单体,所述单体选自:甲基丙烯酸-2-乙基苯氧基酯、丙烯酸-2-乙基苯氧基酯、甲基丙烯酸-2-乙基噻吩酯、丙烯酸-2-乙基噻吩酯、甲基丙烯酸-2-乙基氨基苯酯、丙烯酸-2-乙基氨基苯酯、甲基丙烯酸苯酯、甲基丙烯酸苄酯、甲基丙烯酸-2-苯基乙酯、甲基丙烯酸-3-苯基丙酯、甲基丙烯酸-4-苯基丁酯、甲基丙烯酸-4-甲基苯酯、甲基丙烯酸-4-甲基苄酯、甲基丙烯酸-2,2-甲基苯基乙酯、甲基丙烯酸-2,3-甲基苯基乙酯、甲基丙烯酸-2,4-甲基苯基乙酯、甲基丙烯酸-2-(4-丙基苯基)乙酯、甲基丙烯酸-2-(4-(1-甲基乙基)苯基)乙酯、甲基丙烯酸-2-(4-甲氧基苯基)乙酯、甲基丙烯酸-2-(4-环己基苯基)乙酯、甲基丙烯酸-2-(2-氯苯基)乙酯、甲基丙烯酸-2-(3-氯苯基)乙酯、甲基丙烯酸-2-(4-氯苯基)乙酯、甲基丙烯酸-2-(4-溴苯基)乙酯、甲基丙烯酸-2-(3-苯基苯基)乙酯、甲基丙烯酸-2-(4-苯基苯基)乙酯和甲基丙烯酸-2-(4-苄基苯基)乙酯。
11.权利要求1或2的方法,其中所述合适的材料包括一种或多种高折射率的预聚物,所述预聚物选自甲基丙烯酸酯封端的聚硅氧烷预聚物和丙烯酸酯封端的聚硅氧烷预聚物,所述预聚物含有适量的芳香部分以使所述预聚物的折射率至少为1.42。
12.权利要求1或2的方法,其中所述紫外光吸收部分是一种或者多种苯并三唑类化合物。
13.权利要求1或2的方法,其中所述紫外光吸收部分是一种或者多种选自下述组中的苯并三唑类化合物:丙烯酸-β-(4-苯并三唑基-3-羟基苯氧基)乙酯、4-(2-丙烯酰氧基乙氧基)-2-羟基二苯酮、4-甲基丙烯酰氧基-2-羟基二苯酮、2-(2’-甲基丙烯酰氧基-5’-甲基苯基)苯并三唑、2-(2’-羟基-5’-甲基丙烯酰氧基乙基苯基)-2H-苯并三唑、2-[3’-叔丁基-2’-羟基-5’-(3”-甲基丙烯酰氧基丙基)苯基]-5-氯苯并三唑、2-[3’-叔丁基-5’-(3”-二甲基乙烯基甲硅烷基丙氧基)-2’-羟基苯基]-5-甲氧基苯并三唑和2-[3’-叔丁基-2’-羟基-5’-(3”-甲基丙烯酰氧基丙氧基)苯基]-5-氯苯并三唑。
14.权利要求1或2的方法,其中所述光引发剂选自取代的紫外光引发剂、共轭酮、三嗪衍生物和金属盐。
15.权利要求1或2的方法,其中所述光引发剂选自二茂钛衍生物。
16.权利要求1或2的方法,其中所述可见光由可见光源提供。
17.权利要求1或2的方法,其中所述可见光由氙灯提供。
18.权利要求1或2的方法,其中所述短时间是指少于几个小时。
19.权利要求1或2的方法,其中所述短时间是指约两个小时或者更少。
20.由权利要求1或2所述方法制备的医疗器件的使用方法,该方法包括把所述的医疗器件植入眼中。
21.一种由权利要求1或2所述方法制备的医疗器件。
22.一种由权利要求1或2所述方法制备的人工晶状体。
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PCT/US2004/026776 WO2005026787A1 (en) | 2003-09-08 | 2004-08-19 | Process for manufacturing intraocular lenses with blue light absorption characteristics |
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CN106414514A (zh) * | 2014-05-07 | 2017-02-15 | 土耳其科学技术研究理事会 | 用于制备人工晶状体(iol)的配制物和晶状体制造方法 |
CN106773319A (zh) * | 2017-01-24 | 2017-05-31 | 深圳市华星光电技术有限公司 | 显示装置及其制备方法 |
CN106773319B (zh) * | 2017-01-24 | 2019-09-27 | 深圳市华星光电技术有限公司 | 显示装置及其制备方法 |
CN113166290A (zh) * | 2018-11-30 | 2021-07-23 | 富士胶片株式会社 | 聚合性组合物及隐形眼镜 |
CN113166290B (zh) * | 2018-11-30 | 2023-02-21 | 富士胶片株式会社 | 聚合性组合物及隐形眼镜 |
CN110152059A (zh) * | 2019-05-07 | 2019-08-23 | 浙江大学 | 一种含有抗生素的人工晶状体及其制作方法 |
CN110152059B (zh) * | 2019-05-07 | 2020-07-07 | 浙江大学 | 一种含有抗生素的人工晶状体及其制作方法 |
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WO2005026787A1 (en) | 2005-03-24 |
CA2536762A1 (en) | 2005-03-24 |
JP2007504854A (ja) | 2007-03-08 |
US7276544B2 (en) | 2007-10-02 |
KR20060076290A (ko) | 2006-07-04 |
EP1664855A1 (en) | 2006-06-07 |
AU2004272996A1 (en) | 2005-03-24 |
EP1664855B1 (en) | 2009-03-11 |
US20050055090A1 (en) | 2005-03-10 |
CN1849531B (zh) | 2011-11-16 |
DE602004019948D1 (de) | 2009-04-23 |
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