CN104871036A - 制备改进的uv吸收性眼用透镜的方法 - Google Patents
制备改进的uv吸收性眼用透镜的方法 Download PDFInfo
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- CN104871036A CN104871036A CN201380065744.5A CN201380065744A CN104871036A CN 104871036 A CN104871036 A CN 104871036A CN 201380065744 A CN201380065744 A CN 201380065744A CN 104871036 A CN104871036 A CN 104871036A
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- Prior art keywords
- lens
- acid
- methyl
- alkyl
- acrylic
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- 238000000576 coating method Methods 0.000 claims abstract description 45
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- 239000011248 coating agent Substances 0.000 claims abstract description 29
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- 239000006096 absorbing agent Substances 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 27
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 26
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 23
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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- 239000012965 benzophenone Substances 0.000 claims description 8
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 7
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
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- 230000007062 hydrolysis Effects 0.000 claims description 4
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- 229920000671 polyethylene glycol diacrylate Polymers 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
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- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 claims description 3
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 3
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 3
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 claims description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- VZPULCFQAMRUMH-UHFFFAOYSA-N 1-ethyl-3-methylidenepyrrolidin-2-one Chemical compound CCN1CCC(=C)C1=O VZPULCFQAMRUMH-UHFFFAOYSA-N 0.000 claims description 2
- CXNYYQBHNJHBNH-UHFFFAOYSA-N 1-ethyl-5-methylidenepyrrolidin-2-one Chemical compound CCN1C(=C)CCC1=O CXNYYQBHNJHBNH-UHFFFAOYSA-N 0.000 claims description 2
- ZZDBHIVVDUTWJC-UHFFFAOYSA-N 1-methyl-5-methylidenepyrrolidin-2-one Chemical compound CN1C(=C)CCC1=O ZZDBHIVVDUTWJC-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- RBUACGOFWUSJNX-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-ethenylphenol Chemical group OC1=CC=C(C=C)C=C1N1N=C2C=CC=CC2=N1 RBUACGOFWUSJNX-UHFFFAOYSA-N 0.000 claims description 2
- JNDVNJWCRZQGFQ-UHFFFAOYSA-N 2-methyl-N,N-bis(methylamino)hex-2-enamide Chemical compound CCCC=C(C)C(=O)N(NC)NC JNDVNJWCRZQGFQ-UHFFFAOYSA-N 0.000 claims description 2
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 claims description 2
- KARGMXZXPAWXQJ-UHFFFAOYSA-N 3-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 KARGMXZXPAWXQJ-UHFFFAOYSA-N 0.000 claims description 2
- XVUWMCJNMDQXKX-UHFFFAOYSA-N 5-ethyl-3-methylidenepyrrolidin-2-one Chemical compound CCC1CC(=C)C(=O)N1 XVUWMCJNMDQXKX-UHFFFAOYSA-N 0.000 claims description 2
- VDORPYPVQAFLTR-UHFFFAOYSA-N 5-methyl-3-methylidenepyrrolidin-2-one Chemical compound CC1CC(=C)C(=O)N1 VDORPYPVQAFLTR-UHFFFAOYSA-N 0.000 claims description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims description 2
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- BVILYQIASATHST-UHFFFAOYSA-N N-[4-hydroxy-3-(5-methoxybenzotriazol-2-yl)phenyl]-2-methylprop-2-enamide Chemical compound N1=C2C=C(OC)C=CC2=NN1C1=CC(NC(=O)C(C)=C)=CC=C1O BVILYQIASATHST-UHFFFAOYSA-N 0.000 claims description 2
- OOPYUNNXQSWBQE-UHFFFAOYSA-N OC(C(=O)OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)C)=C Chemical compound OC(C(=O)OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)C)=C OOPYUNNXQSWBQE-UHFFFAOYSA-N 0.000 claims description 2
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- CKIDCRFWPRVLEU-UHFFFAOYSA-N [3-(benzotriazol-2-yl)-4-hydroxyphenyl] prop-2-enoate Chemical compound OC1=CC=C(OC(=O)C=C)C=C1N1N=C2C=CC=CC2=N1 CKIDCRFWPRVLEU-UHFFFAOYSA-N 0.000 claims description 2
- 229940091181 aconitic acid Drugs 0.000 claims description 2
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 claims description 2
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Abstract
本文描述了用于制备UV吸收性接触透镜的划算且具有时效的方法。与涉及使包含UV吸收性乙烯单体的透镜形成组合物共聚合的常规UV吸收性眼用透镜制备方法相反，本发明方法涉及将接触透镜浸入包含含羧基单体单元、UV吸收性单体单元和共价结合自由基引发结构部分的UV吸收性聚合物溶液中以在接触透镜上形成UV吸收涂层。
Description
本发明涉及制备能阻断紫外线(“UV”)辐射，由此一定程度地保护眼睛以防UV辐射导致的损害的眼用透镜(包括接触透镜和眼内透镜)的方法。本发明还提供根据本发明方法制备的UV吸收性眼用透镜。
背景
UV吸收性眼用透镜，特别是UV吸收性接触透镜通常通过所谓的铸造模塑方法大量制备，所述方法涉及使包含可聚合UV吸收剂和至少一种乙烯单体、大单体和/或预聚物的透镜形成组合物在模具中热-或UV引发自由基聚合。包含共价附着在它们的UV吸收性结构部分上的烯属不饱和基团的可共聚苯并三唑、二苯甲酮和三嗪UV吸收剂是已知的且先前已使用。那些UV吸收剂可并入眼用透镜的聚合物基体中。然而，必须将未聚合的UV吸收剂通过提取方法除去以确保所得眼用透镜具有对使用而言所需的生物相容性。另外，当透镜制备依赖于具有比热引发聚合方法更短的加工周期的UV引发聚合方法时，存在与已知可聚合UV吸收剂有关的几个缺点。首先，UV吸收剂并入透镜中的效率可能不确定。第二，透镜形成组合物中存在的UV吸收剂可降低可用于引发聚合的UV射线的量并可甚至降低UV吸收剂共价并入所得透镜中的效率。通常必须将未反应的UV吸收剂在一种或多种提取方法中从透镜中除去。第三，UV吸收剂可导致透镜形成组合物的无效或不均匀的光聚合。
因此，仍需要制备UV吸收性接触透镜的划算方法。
概述
一方面，本文提供制备UV吸收性眼用透镜的方法，所述方法包括以下步骤：得到眼用透镜，优选接触透镜；将眼用透镜浸入包含有机溶剂和UV吸收性聚合物的涂覆溶液中足够的时间以在眼用透镜上形成UV吸收涂层；其中UV吸收性聚合物包含UV吸收性单体单元、共价结合自由基引发结构部分，至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元；和在浸渍步骤以后任选但优选在亲水性乙烯单体或交联剂的存在下照射眼用透镜以获得UV吸收性聚合物在眼用透镜上的光引发接枝。
另一方面，本发明提供眼用透镜，所述透镜包含：聚合物透镜体；在透镜体上的UV吸收性聚合物层；其中UV吸收性聚合物包含UV吸收性单体单元、共价结合自由基引发结构部分和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元，其中UV吸收性聚合物层通过光引发接枝方法接枝在透镜体上。
另一方面，本发明提供眼用透镜，所述透镜包含聚合物透镜体；在透镜体上的UV吸收性聚合物层；其中UV吸收性聚合物包含UV吸收性单体单元、共价结合自由基引发结构部分，和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元，其中UV吸收性聚合物层在亲水性乙烯单体或交联剂的存在下通过光引发接枝方法接枝在透镜体上。
本发明的优点部分描述于以下说明书中，部分会由说明书中获悉，或可通过以下所述方面的实践学习。以下所述优点通过所附权利要求书中特别指出的元素和组合实现和获得。应当理解前文一般性描述和下文的详细描述都仅为示例性和解释性的且不是限制性的。
附图简述
图1显示如实施例1所述接触透镜的储液的UV吸光度光谱，其中1)关于PAA-N20溶液中处理20分钟并在压热器处理以后的透镜，2)关于在PAA-N20-Irg中处理20分钟，在PBS溶液中UV照射5分钟并压热器处理的透镜，且3)关于在PAA-N20-Irg溶液中处理20分钟，在PEG-DA 700水溶液中UV照射5分钟并压热器处理的透镜。x轴上显示UV吸光度的标度在y轴水平处为零，在平行于y轴的最低线处为0.5，在平行于y轴的第二条线处为1.0，在平行于y轴的最高线处为1.5。
详述
在公开和描述本方法以前，应当理解下文所述方面不限于具体化合物、步骤或用途，因而当然可变化。还应当理解本文所用术语仅用于描述具体方面且不意欲为限定性的。
在本说明书和以下的权利要求书中，参考大量术语，应定义所述术语具有如下含义：
必须指出，除非本文中另外清楚地指出，如说明书和所附权利要求书中所用，单数形式“一个/一种(a/an)”和“该(the)”包括复数对象。因此，例如提及“单体”包括两种或更多种这类单体的混合物，等。
如本文所用“约”意指称为“约”的数包括所述数加或减该所述数的1-10％。
“任选”或“任选地”意指随后描述的事件或情形可能发生或不发生，且该描述包括事件或情形发生的情况和它不发生的情况。
除非另外定义，本文所用所有技术和科学术语具有与本发明所属领域中的技术人员通常理解的相同含义。如本公开内容所用，除非另外说明，以下术语应当理解具有如下含义。
“眼用透镜”指接触透镜和/或眼内透镜。“接触透镜”指可放在佩戴者眼睛上或眼内的结构。接触透镜可校正、改善或改变使用者的视力，但未必是这种情况。“硅氧烷水凝胶接触透镜”指包含硅氧烷水凝胶材料的接触透镜。
如本申请中所用，术语“水凝胶”或“水凝胶材料”指非水溶性且在完全水化时聚合物基体内可含有至少10重量％水的交联聚合材料。
“硅氧烷水凝胶”指含有硅氧烷的水凝胶。硅氧烷水凝胶通常通过包含至少一种含硅氧烷乙烯单体或至少一种含硅氧烷乙烯大单体的可聚合组合物或至少一种具有烯属不饱和基团的含硅氧烷预聚物共聚得到。
“乙烯单体”指具有一个唯一烯属不饱和基团的化合物。
术语“烯键式不饱和基团”或“烯属不饱和基团”以宽泛的意义用于本文中并意欲包括任何含有至少一个>C＝C<基团的基团。示例的烯属不饱和基团包括但不限于(甲基)丙烯酰基烯丙基、乙烯基苯乙烯基或其它含C＝C基团。
术语“(甲基)丙烯酰胺”指甲基丙烯酰胺和/或丙烯酰胺。
术语“(甲基)丙烯酸酯”指甲基丙烯酸酯和/或丙烯酸酯。
如本文所用“亲水乙烯单体”指可聚合形成水溶性或可吸收至少10重量％水的均聚物的乙烯单体。
“疏水性乙烯单体”指可聚合形成不溶于水并可吸收小于10重量％水的均聚物的乙烯单体。
如本申请中所用，术语“大单体”或“预聚物”指含有两个或更多烯属不饱和基团的中和高分子量化合物或聚合物。中和高分子量通常意指大于700道尔顿的平均分子量。
如本申请中所用，术语“交联剂”指具有至少两个烯属不饱和基团的化合物。“交联试剂”指具有约700道尔顿或更小的分子量的交联剂。
如本申请中所用，术语“聚合物”意指通过使一种或多种单体或大单体或预聚物聚合/交联而形成的材料。
除非另外明确指出或者除非另外指出测试条件，如本申请中所用，术语聚合材料(包括单体或大单体材料)的“分子量”指重均分子量。
本发明UV吸收性聚合物的分子量可宽泛地变化。它可以为约3000至约700,000，优选约5000至约500,000。
关于化合物或材料在溶剂中的术语“可溶”意指化合物或材料在室温(即约20℃至约30℃的温度)下可溶于溶剂中以得到具有至少约1重量％的浓度的溶液。
关于化合物或材料在溶剂中的术语“不溶”意指化合物或材料在室温(如上文所定义)下可溶于溶剂中以得到具有小于0.005重量％的浓度的溶液。
关于聚合物的术语“水溶性”意指聚合物在室温(如上文所定义)下可以以足以形成具有至少约1重量％的浓度的聚合物水溶液的程度溶于水中。
如本申请中所用，术语“水接触角”指平均水接触角(即通过座滴法(sessile drop method)测定的接触角)，其通过接触角的平均值测量而得到。
如本申请中所用，术语“交联涂层”或“水凝胶涂层”互换地用于描述在完全水化时可含有水的具有三维网络的交联聚合材料。交联聚合材料的三维网络可通过两种或更多种线性或支化聚合物通过交键交联形成。
“聚合物”意指通过使一种或多种单体交联或聚合形成的材料。
本发明一般性地涉及制备UV吸收性眼用透镜，特别是接触透镜的划算且有时效的方法。与涉及使包含UV吸收性乙烯单体的透镜形成组合物共聚合的传统UV吸收性眼用透镜制备方法相反，本发明方法涉及在模制以后简单的浸渍方法以将UV吸收涂层应用于眼用透镜上。本发明部分地基于这一发现：具有羧基的UV吸收性聚合物层(或涂层)可仅通过将眼用透镜浸入UV吸收性聚合物的溶液中而容易地应用于铸造的眼用透镜上。UV吸收涂层的厚度和耐久性可通过在UV吸收性聚合物溶液中使用有机溶剂作为溶剂或溶剂混合物的一种，然后用水或水与至少一种有机溶剂的混合物冲洗而控制。认为当含有至少一种有机溶剂的溶剂体系用于制备涂覆溶液时，它可使眼用透镜溶胀使得一部分UV吸收性聚合物可渗入眼用透镜内并提高UV吸收涂层的厚度。随后的水洗步骤可使眼用透镜收缩并部分地嵌入UV吸收性聚合物并提高UV吸收涂层的耐久性。
UV吸收涂层的耐久性进一步通过除UV吸收性单元和含羧基单体单元外还包含共价结合自由基引发结构部分的UV吸收性聚合物改进。这些自由基引发结构部分的存在容许UV吸收涂层在亲水性乙烯单体或交联剂的不存在或存在下光引发接枝(即通过那些自由基引发结构部分的其余残基共价连接)在眼用透镜上。这类接枝可通过在浸渍步骤以后，任选但优选在亲水性乙烯单体或交联剂的存在下照射眼用透镜而实现。
本发明可提供以下优点。首先，UV吸收剂结合到眼用透镜中在透镜形成组合物在模具中固化以后进行，由此可克服在先前“背景”部分中描述的使用UV吸收性乙烯单体的缺点。第二，整个方法基于湿化学(将眼用透镜浸入溶液中一段时间)。该方法可容易地在全自动大量生产环境中进行。第三，并入UV吸收剂的方法可以为用于将水凝胶涂层应用于接触透镜的涂覆方法的组成部分。第四，包括光引发接枝步骤的方法将UV吸收性聚合物接枝在眼用透镜上。这具有降低或防止UV吸收性聚合物由眼用透镜再迁移(即沥滤)到储存透镜的溶液中的效果。换而言之，UV吸收性聚合物比不用接枝步骤更好地固定在眼用透镜上。
一方面，本发明提供制备UV吸收性眼用透镜的方法，所述方法包括以下步骤：得到眼用透镜，优选接触透镜；将眼用透镜浸入包含有机溶剂和UV吸收性聚合物的涂覆溶液中足够的时间以在眼用透镜上形成UV吸收涂层；其中UV吸收性聚合物包含UV吸收性单体单元、共价结合自由基引发结构部分，和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元，在浸渍步骤以后任选但优选在亲水性乙烯单体或交联剂的存在下照射眼用透镜以获得UV吸收性聚合物在眼用透镜上的光引发接枝。
根据本发明，接触透镜可以为任何接触透镜，包括软和硬接触透镜。优选的软接触透镜为硅氧烷水凝胶接触透镜。
本领域技术人员已知如何制备接触透镜。例如接触透镜可以在例如如美国专利No.3,408,429所述常规“旋转铸造模塑”，或通过如美国专利No.4,347,198；5,508,317；5,583,463；5,789,464；和5,849,810所述静态形式的全铸造模塑方法，或者通过将制备定制接触透镜中所用硅氧烷水凝胶纽扣形物车床切割(lathe cutting)而生产。在铸造模塑中，通常将透镜配制剂加入模具中并在模具中固化(即聚合和/或交联)以制备接触透镜。对于优选的硅氧烷水凝胶接触透镜的生产，用于接触透镜的铸造模塑的透镜配制剂通常包含至少一种选自如下的组分：含硅氧烷乙烯单体、含硅氧烷乙烯大单体、亲水乙烯单体、亲水性乙烯大单体、疏水性乙烯单体及其组合。应当理解透镜形成组合物还可包含如本领域技术人员已知的各种组分，例如交联试剂、能见度着色剂(例如染料、颜料或其混合物)、抗微生物剂(例如优选银纳米颗粒)、生物活性试剂、可浸出润滑剂、可浸出眼泪稳定剂及其混合物。然后可如本领域技术人员已知使所得硅氧烷水凝胶接触透镜经受用提取溶剂提取以从所得透镜中除去未聚合的组分并经受水化方法。另外，接触透镜可以为有色接触透镜(即如本领域技术人员熟知的具有至少一种印在其上的有色图案的接触透镜)。
本领域技术人员非常了解如何制备透镜配制剂。大量非硅氧烷水凝胶透镜配制剂和硅氧烷水凝胶透镜配制剂描述于该申请的提交日期前出版的大量专利和专利申请中。它们中所有都可用于得到接触透镜中。用于制备商业硅氧烷水凝胶接触透镜的硅氧烷水凝胶透镜配制剂，例如lotrafilcon A、lotrafilcon B、balafilcon A、galyfilcon A、senofilcon A、narafilcon A、narafilcon B、comfilcon A、enfilcon A、asmofilcon A、filconII 3也可用于制备硅氧烷水凝胶接触透镜，其然后可用于根据本发明方法制备UV吸收性接触透镜。
用于制备接触透镜的透镜模具是本领域技术人员熟知的，并例如用于铸造模塑或旋转铸造中。例如模具(用于铸造模塑的)通常包含至少两个模具段(或部分)或半模，即第一和第二半模。第一半模限定第一模塑(或光学)表面，第二半模限定第二模塑(或光学)表面。配置第一和第二半模以彼此容纳使得透镜形成空穴在第一模塑表面与第二模塑表面之间形成。半模的模塑表面为模具的空穴形成表面并与透镜形成材料直接接触。
生产用于将接触透镜铸造模塑的模具段的方法通常是本领域技术人员熟知的。本发明方法不限于形成模具的任何具体方法。事实上，任何形成模具的方法可用于本发明中。第一和第二半模可通过各种技术如注塑或车削(lathing)形成。形成模具的合适方法的实例公开于美国专利No.4,444,711，Schad；4,460,534，Boehm等人；5,843,346，Morrill；和5,894,002，Boneberger等人中，也通过引用将其并入本文中。
本领域中已知用于制备模具的基本所有材料可用于制备用于制备接触透镜的模具。例如，可使用聚合材料如聚乙烯、聚丙烯、聚苯乙烯、PMMA、COC品级8007-S10(乙烯与降冰片烯的透明无定形共聚物，来自Ticona GmbH of Frankfurt，德国和Summit，New Jersey)等。可使用容许UV光透过的其它材料，例如石英玻璃和蓝宝石。
根据本发明，UV吸收性聚合物包含UV吸收性单体单元、共价结合自由基引发结构部分和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元。各UV吸收性单体单元包含UV吸收性结构部分，所述结构部分可以为苯并三唑结构部分、二苯甲酮结构部分或三嗪结构部分，苯并三唑结构部分或二苯甲酮结构部分为优选的UV吸收性结构部分，苯并三唑结构部分为最优选的UV吸收性结构部分。如本申请中所用，术语“单体单元”指聚合物的重复单元，其衍生自参与聚合的乙烯单体，并可在聚合以后任选通过化合物改性。
通过使用官能化自由基引发化合物而引入UV吸收性聚合物中的各个共价结合自由基引发结构部分适于结合在前体聚合物或中间UV吸收性聚合物的羧基上。适于结合在羧基上的官能化自由基引发化合物是已知的且描述于例如WO 03/042724、WO 86/005778、EP-B 632 329和EP-B 800 511中。优选的自由基引发化合物为Irgacure型的那些。
本发明UV吸收性聚合物可由通过使包含至少一种含羧基乙烯单体和至少一种UV吸收性乙烯单体的可聚合混合物在乙烯单体的存在或不存在下共聚而得到的中间UV吸收性聚合物得到，条件是含羧基乙烯单体以至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)的量存在于可聚合组合物中。
所得到的中间UV吸收性聚合物可通过使它在偶联反应中与官能化自由基引发化合物，例如借助具有N-(3-二甲基氨基丙基)-N’-乙基碳二亚胺的活性酯路线与Irgacure型光引发剂反应而进一步改性以包含共价结合自由基引发结构部分。下文所述其它“偶联反应”也可用于将官能化自由基引发化合物连接在中间UV吸收性聚合物上。
任何UV吸收性乙烯单体可用于制备本发明中间UV吸收性聚合物。优选的UV吸收性乙烯单体的实例包括但不限于含苯并三唑乙烯单体(例如2-(2-羟基-5-乙烯基苯基)-2H-苯并三唑、2-(2-羟基-5-丙烯酰氧基苯基)-2H-苯并三唑、2-(2-羟基-3-甲基丙烯酰氨基甲基-5-叔辛基苯基)苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氨基-苯基)-5-氯苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氨基苯基)-5-甲氧基苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氧基丙基-3'-叔丁基-苯基)-5-氯苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氧基乙基苯基)苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氧基丙基-苯基)苯并三唑或其组合)；含二苯甲酮乙烯基单体(例如2-羟基-4-丙烯酰氧基烷氧基二苯甲酮、2-羟基-4-甲基丙烯酰氧基烷氧基二苯甲酮、烯丙基-2-羟基二苯甲酮和2-羟基-4-甲基丙烯酰氧基二苯甲酮或其组合)；或其组合。含苯并三唑乙烯基单体可根据美国专利No.3,299,173、4,612,358、4,716,234、4,528,311(通过引用将其全部并入本文中)所述程序制备或者可由商业供应商得到。含二苯甲酮乙烯基单体可根据美国专利No.3,162,676(通过引用将其全部并入本文中)所述程序制备或者可由商业供应商得到。
适于结合在羧基上的任何官能化自由基引发化合物可用于制备本发明UV吸收性聚合物。适于结合在羧基上的官能化自由基引发化合物包含对羧基呈共反应性的基团，例如氨基或羟基，优选氨基。自由基引发部分可属于不同的类型，例如噻吨酮类型，以及优选苯偶姻类型。
在本发明一个优选实施方案中，羧基与官能化自由基引发化合物之间的共价键合借助羧基与自由基引发化合物的羟基、氨基或烷基氨基的反应，例如通过使用EP B1 1299753的式(10a)自由基引发化合物进行，通过引用将其相关部分并入本文中。羧基与例如EP B1 1299753的式10a自由基引发化合物的羟基或氨基的反应是本领域中熟知的并且可例如如有机化学教课书中所述进行。
任何合适的含羧基乙烯单体可用于制备本发明中间UV吸收性聚合物。优选的含羧基乙烯单体的实例包括但不限于丙烯酸、C1-C12烷基丙烯酸(例如甲基丙烯酸、乙基丙烯酸、丙基丙烯酸、丁基丙烯酸、戊基丙烯酸等)、N,N-2-丙烯酰氨基羟基乙酸、β-甲基-丙烯酸(巴豆酸)、α-苯基丙烯酸、β-丙烯酰氧基丙酸、山梨酸、当归酸、肉桂酸、1-羧基-4-苯基丁二烯-1,3、衣康酸、柠康酸、中康酸、戊烯二酸、乌头酸、马来酸、富马酸、三羧基乙烯及其组合。UV吸收性聚合物由至少一种选自丙烯酸、甲基丙烯酸、乙基丙烯酸、丙基丙烯酸、丁基丙烯酸、戊基丙烯酸及其组合，更优选选自丙烯酸、甲基丙烯酸、乙基丙烯酸、丙基丙烯酸及其组合，甚至更优选选自丙烯酸、甲基丙烯酸、乙基丙烯酸及其组合的含羧基乙烯单体制备。
作为选择，本发明UV吸收性聚合物可通过使UV吸收性化合物和自由基引发化合物顺序地(不以特定顺序)或者通过使UV吸收性化合物和自由基引发化合物的混合物与(使UV吸收性结构部分共价连接在)具有至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元的前体聚合物在本领域技术人员已知的偶联反应中反应而得到。
“偶联反应”意欲描述在本领域技术人员熟知的各种反应条件如氧化还原条件、脱水缩合条件、加成条件、取代(或置换)条件、迪尔斯阿尔德反应条件、阳离子交联条件、开环条件、环氧树脂硬化条件及其组合下在偶联剂的存在或不存在下一对匹配的官能团之间形成共价键或键的任何反应。下面给出在各种反应条件下选自如下的一对匹配共反应性官能团之间的偶联反应的非限定性实例以说明：优选氨基(如上所定义的-NHR’)、羟基、羧酸基团、酰基卤基团(─COX，X＝Cl、Br或I)、酸酐基团、醛基团、吖内酯(azlactone)基团、异氰酸酯基团、环氧基、吖丙啶(aziridine)基团、硫醇基和酰胺基团(─CONH2)。羧酸基团与氨基-NHR’在偶联剂—碳化二亚胺(例如1-乙基-3-(3-二甲基氨基丙基)碳化二亚胺(EDC)、N,N’-二环己基碳化二亚胺(DCC)、1-环己基-3-(2-吗啉基乙基)碳化二亚胺、二异丙基碳化二亚胺或其混合物)的存在下反应以形成酰胺键；羧酸基团与异氰酸酯基团在加热下反应以形成酰胺键；羧基与环氧基或吖丙啶基团反应以形成酯键；羧基与卤基团(–Cl、–Br或–I)反应以形成酯键；氨基与醛基团反应以形成席夫碱，可将其进一步还原；氨基-NHR’与酰基氯或酰基溴基团或者与酸酐基团反应以形成酰胺键(-共聚-NR’-)；氨基-NHR’与异氰酸酯基团反应以形成脲键(-NR’-C(O)-NH-)；氨基-NHR’与环氧基或吖丙啶基团反应以形成胺碱(C-NR’)；氨基与吖内酯基团反应(开环)以形成键(-C(O)NH-CR1R2-(CH2)r-C(O)-NR’-)；羟基与异氰酸酯反应以形成氨基甲酸酯键；羟基与环氧基或吖丙啶反应以形成醚键(-O-)；羟基与酰基氯或酰基溴基团或与酸酐基团反应以形成酯键；羟基与吖内酯基团在催化剂的存在下反应以形成键(-C(O)NH-CR1R2-(CH2)r-C(O)-O-)；硫醇基(-SH)与异氰酸酯反应以形成硫代氨基甲酸酯键(-N-C(O)-S-)；硫醇基与环氧基或吖丙啶反应以形成硫醚键(-S-)；硫醇基与酰基氯或酰基溴基团或与酸酐基团反应以形成硫酯键；硫醇基与吖内酯基团在催化剂的存在下反应以形成键(-C(O)NH-亚烷基-C(O)-S-)；硫醇基与乙烯基基于硫醇-烯反应在硫醇-烯反应条件下反应以形成硫醚键(–S–)；硫醇基与丙烯酰基或甲基丙烯酰基基于迈克尔加成在合适的反应条件下反应以形成硫醚键。
还应当理解具有两个反应性官能团的偶联剂可用于偶联反应中。例如，二异氰酸酯、二酰基卤、二羧酸、二吖内酯或二环氧化合物可用于两个羟基、两个氨基、两个羧基、两个环氧基或其组合的偶联中；二胺或二羟基化合物可用于两个异氰酸酯、两个环氧基、两个吖丙啶、两个羧基、两个酰基卤或两个吖内酯基团或其组合的偶联中。
上述偶联反应的反应条件教导于教课书中且为本领域技术人员熟知的。
任何包含至少至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元的聚合物可作为前体聚合物用于制备本发明UV吸收性聚合物。优选前体聚合物为：含羧基乙烯单体(丙烯酸或C1-C12烷基丙烯酸)的均聚物；丙烯酸和C1-C12烷基丙烯酸的共聚物；含羧基乙烯单体(丙烯酸或C1-C12烷基丙烯酸)和含氨基乙烯单体(例如(甲基)丙烯酸氨基-C2-C6烷基酯、(甲基)丙烯酸C1-C6烷基氨基-C2-C6烷基酯、烯丙胺、乙烯胺、氨基-C2-C6烷基(甲基)丙烯酰胺、C1-C6烷基氨基-C2-C6烷基(甲基)丙烯酰胺)的共聚物；含羧基乙烯单体(丙烯酸或C1-C12烷基丙烯酸)和一种或多种亲水乙烯单体的共聚物，所述亲水乙烯单体不含羧基或氨基且选自丙烯酰胺(AAm)、甲基丙烯酰胺N,N-二甲基丙烯酰胺(DMA)、N,N-二甲基甲基丙烯酰胺(DMMA)、N-乙烯基吡咯烷酮(NVP)、甲基丙烯酸N,N,-二甲基氨基乙基酯(DMAEM)、丙烯酸N,N-二甲基氨基乙基酯(DMAEA)、N,N-二甲基氨基丙基甲基丙烯酰胺(DMAPMAm)、N,N-二甲基氨基丙基丙烯酰胺(DMAPAAm)、甲基丙烯酸甘油酯、3-丙烯酰氨基-1-丙醇、N-羟基乙基丙烯酰胺、N-[三(羟基甲基)甲基]-丙烯酰胺、N-甲基-3-亚甲基-2-吡咯烷酮、1-乙基-3-亚甲基-2-吡咯烷酮、1-甲基-5-亚甲基-2-吡咯烷酮、1-乙基-5-亚甲基-2-吡咯烷酮、5-甲基-3-亚甲基-2-吡咯烷酮、5-乙基-3-亚甲基-2-吡咯烷酮、(甲基)丙烯酸2-羟基乙基酯、(甲基)丙烯酸羟基丙基酯、重均分子量为至多1500道尔顿的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯、N-乙烯基甲酰胺、N-乙烯基乙酰胺、N-乙烯基异丙基酰胺、N-乙烯基-N-甲基乙酰胺、烯丙醇、乙烯醇(共聚物中乙酸乙烯酯的水解形式)及其组合。更优选前体聚合物为聚丙烯酸、聚甲基丙烯酸、聚(C2-C12烷基丙烯酸)、聚(丙烯酸-共聚-甲基丙烯酸)、聚[C2-C12烷基丙烯酸-共聚-(甲基)丙烯酸]、聚(N,N-2-丙烯酰氨基羟基乙酸)、聚[(甲基)丙烯酸-共聚-丙烯酰胺]、聚[(甲基)丙烯酸-共聚-乙烯基吡咯烷酮]、聚[C2-C12烷基丙烯酸-共聚-丙烯酰胺]、聚[C2-C12烷基丙烯酸-共聚-乙烯基吡咯烷酮]、水解聚[(甲基)丙烯酸-共聚-乙酸乙烯酯]、水解聚[C2-C12烷基丙烯酸-共聚-乙酸乙烯酯]或其组合。
包含UV吸收性结构部分和选自氨基、吖内酯基团、环氧基、异氰酸酯基团、吖丙啶基团及其组合的反应性官能团的UV吸收性化合物可用于本发明中。可用于本发明中的具有苯并三唑结构部分的优选UV吸收性化合物由式I、II或III表示：
其中：
R1和R2相互独立地为氢、C1-C12线性或支化烷基、卤素(Cl或Br)、C6-C24芳基、C7-C24烷芳基、C7-C24芳烷基或C1-C12线性或支化烷氧基；
L1为共价键或–Xa–E1–Xb–E2–Xc–的二价基团，其中Xa为共价键，–O–，羰基–(RaO)n–的二价基团，其中Ra为线性或支化C1-C12亚烷基且n为1-10，其中R”为H或C1-C8烷基，E1和E2相互独立地为共价键，–(RaO)n–的二价基团，其中Ra和n为以上定义的， 其中R”为H或C1-C8烷基、C1-C12线性或支化亚烷基二价基团、具有至多40个碳原子的环烷基二价基团、具有至多40个碳原子的烷基环烷基二价基团、具有至多40个碳原子的烷基芳基二价基团、具有至多40个碳原子的芳基亚烷基二价基团，或者式–C(O)L2C(O)–的二羰基，其中L2为C1-C12线性或支化亚烷基二价基团，或者–(Re1–O)w1–(Re2–O)w2–(Re3–O)w3–，其中Re1、Re2和Re3相互独立地为线性或支化C1-C4亚烷基且w1、w2和w3相互独立地为为0-20的值，条件是(n+m+p)的和为1-60，且Xb和Xc相互独立地为共价键、羰基、–O–、 –S–和其中R”如上文所定义；且
Y为吖内酯基团、环氧基、异氰酸酯基团、吖丙啶基团或–NHR’的氨基，其中R’为氢或C1-C12未被取代或取代的线性或支化烷基。
式I、II或III的含氨基UV吸收性化合物的实例包括但不限于2-(2’-羟基-3’-氨基甲基-5’-甲基苯基)-2H-苯并三唑、2-(2’-羟基-5’-氨基苯基)-2H-苯并三唑、2-(2’-羟基-4’-(3-氨基丙氧基)苯基)-2H-苯并三唑、2-(2’-羟基-4’-乙基氨基苯基)-5-氯-苯并三唑。作为选择，式I、II或III的含氨基UV吸收性化合物可通过根据本领域技术人员熟知的迈克尔加成或硫醇-烯反应使它的烯属不饱和基团与氨基硫醇(例如2-氨基乙二醇)反应而由含苯并三唑乙烯基单体(上述那些中的任一种)制备。
其中Y为吖内酯基团、环氧基或异氰酸酯基团的式I、II或III的UV吸收性化合物可由具有一个羟基烷氧基或氨基的苯并三唑化合物通过使它与过量摩尔当量量的二吖内酯化合物、二环氧化合物或二异氰酸酯化合物在本领域技术人员熟知的常规偶联反应条件下反应而制备。
二环氧化合物的实例为新戊二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、乙二醇二缩水甘油醚、二乙二醇二缩水甘油醚、聚乙二醇二缩水甘油醚、丙二醇二缩水甘油醚和二丙二醇二缩水甘油醚。这类二环氧化合物是市售的(例如来自Nagase ChemteX Corporation的那些DENACOL系列二环氧化合物)。C10-C24二吖内酯化合物的实例包括美国专利No.4,485,236(通过引用将其全部并入本文中)所述那些。C4-C24二异氰酸酯的实例可用于本发明中。二异氰酸酯包括但不限于异佛尔酮二异氰酸酯、六甲基-1,6-二异氰酸酯、4,4'-二环己基甲烷二异氰酸酯、甲苯二异氰酸酯、4,4'-二苯基甲烷二异氰酸酯、4,4'-二苯基甲烷二异氰酸酯、对亚苯基二异氰酸酯、1,4-亚苯基4,4'-二苯基二异氰酸酯、1,3-双-(4,4'-异氰酸酯基甲基)环己烷、环己烷二异氰酸酯及其组合。
在式I、II或III中，Y优选为–NHR’的氨基，其中R’为氢或C1-C12未被取代或取代的线性或支化烷基。
可用于本发明中的具有二苯甲酮结构部分的优选UV吸收性化合物由式IV表示：
其中：
R3为氢、C1-C12线性或支化烷基、卤素、C6-C24芳基、C7-C24烷芳基、C7-C24芳烷基或C1-C12线性或支化烷氧基；
L3为共价键或–Xa–E1–Xb–E2–Xc–的二价基团，其中Xa为共价键，–O–，羰基–(RaO)n–的二价基团，其中Ra为线性或支化C1-C12亚烷基且n为1-10，其中R”为H或C1-C8烷基，E1和E2相互独立地为共价键，–(RaO)n–的二价基团，其中Ra和n是以上定义的， 其中R”为H或C1-C8烷基、C1-C12线性或支化亚烷基二价基团、具有至多40个碳原子的环烷基二价基团、具有至多40个碳原子的烷基环烷基二价基团、具有至多40个碳原子的烷基芳基二价基团、具有至多40个碳原子的芳基亚烷基二价基团，或者式–C(O)L2C(O)–的二羰基，其中L2为C1-C12线性或支化亚烷基二价基团或者–(Re1–O)w1–(Re2–O)w2–(Re3–O)w3–，其中Re1、Re2和Re3相互独立地为线性或支化C1-C4亚烷基且w1、w2和w3相互独立地为为0-20的值，条件是(n+m+p)的和为1-60，且Xb和Xc相互独立地为共价键、羰基、–O–、 –S–和其中R”如上文所定义；且
Y1为吖内酯基团、环氧基、异氰酸酯基团、吖丙啶基团，或–NHR的氨基，其中R为氢或C1-C12未被取代或取代的线性或支化烷基。
在式IV中，Y1优选为–NHR的氨基，其中R为氢或C1-C20未被取代或取代的线性或支化烷基。
式IV的含氨基UV吸收性化合物可根据本领域技术人员熟知的迈克尔加成或硫醇-烯反应使它的烯属不饱和基团与氨基硫醇(例如2-氨基乙硫醇)反应而由含二苯甲酮乙烯基单体制备。所得式IV的含氨基UV吸收性化合物然后可直接用于本发明中或者用于通过使式IV的含氨基UV吸收性化合物与过量摩尔当量量的二吖内酯化合物、二环氧化合物或二异氰酸酯化合物在本领域技术人员熟知的常规偶联反应条件下反应而制备式IV的UV吸收性化合物，其中Y1为吖内酯基团、环氧基或异氰酸酯基团。
在优选实施方案中，UV吸收性化合物包含一种或多种式I、II、III或IV，优选式I、II或III的化合物，其中Y和Y1为–NHR’的氨基，其中R’为氢或C1-C12未被取代或取代的线性或支化烷基，R1和R2相互独立地为氢、卤素、C1-C6线性或支化烷氧基、C1-C12线性或支化烷基(优选叔丁基)或C6-C15芳基，L为共价键或–Xa–E1–Xb–E2–Xc–的二价基团，其中Xa为共价键或–O–、其中R”为H或C1-C8烷基，E1和E2相互独立地为共价键，–(RaO)n–的二价基团，其中Ra为线性或支化C1-C12亚烷基且n为1-10，C1-C12线性或支化亚烷基二价基团，具有至多12个碳原子的环烷基二价基团，具有至多20个碳原子的烷基环烷基二价基团，具有至多20个碳原子的烷基苯基二价基团，或具有至多20个碳原子的苯基亚烷基二价基团，Xb和Xc相互独立地为共价键、羰基、–O–、 –S–和其中R”是上文定义的；且Y为–NHR的氨基，其中R为氢或C1-C6未被取代或取代的线性或支化烷基。
中间UV吸收性聚合物的一个优选实施方案为丙烯酸或甲基丙烯酸与优选包含下式结构单元的UV吸收性乙烯单体的共聚物：
R’：H或CH3
其中Y为UV吸收性结构部分的基团，(m+n)的和为21-10000的整数，且m:n的比为200:1-20:1。
在任何给定的本发明UV吸收性聚合物中，共价结合自由基引发结构部分优选以约3至约15摩尔％，更优选约5至约10摩尔％存在于UV吸收性聚合物中。
在任何给定的本发明UV吸收性聚合物中，UV吸收性单体单元优选以约4至约15摩尔％，更优选约5-12摩尔％存在于UV吸收性聚合物中。
在任何给定的本发明UV吸收性聚合物中，UV吸收性单体单元与共价结合自由基引发结构部分的比为100:1-1:100，优选10:1-1:10，同时含羧基单元的摩尔％为至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％。
用于在接触透镜上形成UV吸收层(涂层)的UV吸收性聚合物溶液可通过将一种或多种UV吸收性聚合物溶于水、水和一种或多种与水溶混的有机溶剂的混合物、有机溶剂或一种或多种有机溶剂的混合物中而制备。优选的有机溶剂的实例包括但不限于四氢呋喃、三丙二醇甲基醚、二丙二醇甲基醚、乙二醇正丁基醚、酮(例如丙酮、甲乙酮等)、二乙二醇正丁基醚、二乙二醇甲基醚、乙二醇苯基醚、丙二醇甲基醚、丙二醇甲基醚乙酸酯、二丙二醇甲基醚乙酸酯、丙二醇正丙基醚、二丙二醇正丙基醚、三丙二醇正丁基醚、丙二醇正丁基醚、二丙二醇正丁基醚、三丙二醇正丁基醚、丙二醇苯基醚、二丙二醇二甲醚、聚乙二醇、聚丙二醇、乙酸乙酯、乙酸丁酯、乙酸戊酯、乳酸甲酯、乳酸乙酯、乳酸异丙酯、二氯甲烷、2-丁醇、1-丙醇、2-丙醇、薄荷醇、环己醇、环戊醇和外-降冰片(exonorborneol)、2-戊醇、3-戊醇、2-己醇、3-己醇、3-甲基-2-丁醇、2-庚醇、2-辛醇、2-壬醇、2-癸醇、3-辛醇、降冰片(norborneol)、叔丁醇、叔戊醇、2-甲基-2-戊醇、2,3-二甲基-2-丁醇、3-甲基-3-戊醇、1-甲基环己醇、2-甲基-2-己醇、3,7-二甲基-3-辛醇、1-氯-2-甲基-2-丙醇、2-甲基-2-庚醇、2-甲基-2-辛醇、2-2-甲基-2-壬醇、2-甲基-2-癸醇、3-甲基-3-己醇、3-甲基-3-庚醇、4-甲基-4-庚醇、3-甲基-3-辛醇、4-甲基-4-辛醇、3-甲基-3-壬醇、4-甲基-4-壬醇、3-甲基-3-辛醇、3-乙基-3-己醇、3-甲基-3-庚醇、4-乙基-4-庚醇、4-丙基-4-庚醇、4-异丙基-4-庚醇、2,4-二甲基-2-戊醇、1-甲基环戊醇、1-乙基环戊醇、1-乙基环戊醇、3-羟基-3-甲基-1-丁烯、4-羟基-4-甲基-1-环戊醇、2-苯基-2-丙醇、2-甲氧基-2-甲基-2-丙醇2,3,4-三甲基-3-戊醇、3,7-二甲基-3-辛醇、2-苯基-2-丁醇、2-甲基-1-苯基-2-丙醇和3-乙基-3-戊醇、1-乙氧基-2-丙醇、1-甲基-2-丙醇、叔戊醇、异丙醇、1-甲基-2-吡咯烷酮、N,N-二甲基丙酰胺、二甲基甲酰胺、二甲基乙酰胺、二甲基丙酰胺、N-甲基吡咯烷酮及其混合物。
优选将UV吸收性聚合物溶于水与一种或多种有机溶剂的混合物、有机溶剂或一种或多种有机溶剂的混合物中。认为含有至少一种有机溶剂的溶剂体系可使接触透镜溶胀使得一部分UV吸收性聚合物可渗入接触透镜中并提高UV吸收涂层的厚度和耐久性。上述任何有机溶剂可用于制备UV吸收性聚合物溶液，条件是它可溶解UV吸收性聚合物。
接触透镜与UV吸收性聚合物溶液接触可以以本领域技术人员已知的任何方式进行。优选的接触方法是将接触透镜浸入溶液中或用溶液喷雾接触透镜，前者是优选的。应当理解在与UV吸收性聚合物溶液接触以前可使接触透镜经受用提取溶剂提取以从模制透镜中除去未聚合的组分，如本领域技术人员所知。作为选择，提取步骤可在将UV吸收性聚合物的涂层(层)应用于接触透镜上后进行。
在优选实施方案中，有机溶剂以至少约60％，优选至少约70％，更优选至少约80％，甚至更优选至少约90％，最优选至少约95％(以重量计)的量存在于涂覆溶液中，且本发明方法进一步包括以下步骤：将其上具有UV吸收涂层的眼用透镜用水和至多约50％，优选至多约40％，更优选至多约30％，甚至更优选至多约20％，最优选至多约10％(以重量计)有机溶剂的混合物冲洗。
接枝方法可例如由热的作用热引发或者优选由辐射，特别是由UV辐射引发。合适的照射光源是技术人员已知的且包括例如汞灯、高压汞灯、氙灯、碳弧灯或太阳光。照射时间可例如取决于所得眼用透镜的所需性能，但通常为至多30分钟，优选10秒至10分钟，特别优选0.5-5分钟。有利的是在惰性气体气氛中进行照射。照射也可在溶液中，例如在pH 7.0的PBS溶液中进行。合适的灯为以约4-6mW/cm2的强度使用约5分钟的Hamamatsu灯。在接枝以后，可例如通过用合适的溶剂处理而除去任何非共价键合的聚合物、低聚物或形成的未反应大单体。
几乎任何亲水性乙烯单体可用于本发明中。合适的亲水性乙烯单体为(非穷举地)(甲基)丙烯酰胺、二烷基(C1-C6)(甲基)丙烯酰胺、(C1-C6)烷基(甲基)丙烯酰胺、羟基取代的较低级烷基(C1-C6)(甲基)丙烯酰胺、羟基取代的较低级烷基(C1-C6)(甲基)丙烯酸酯、羟基取代的较低级烷基乙烯基醚、N-乙烯基吡咯、N-乙烯基-2-吡咯烷酮、2-乙烯基噁唑啉、2-乙烯基-4,4'-二烷基噁唑啉-5-酮、2-和4-乙烯基吡啶、具有总计3-6个碳原子的烯键式不饱和羧酸、氨基(较低级烷基)(其中术语“氨基”还包括季铵)、单(较低级烷基氨基)(较低级烷基)和二(较低级烷基氨基)(较低级烷基)丙烯酸酯和甲基丙烯酸酯、烯丙醇、N-乙烯基烷基酰胺、N-乙烯基-N-烷基酰胺等。
优选的亲水性乙烯单体为N,N-二甲基丙烯酰胺(DMA)、N,N-二甲基甲基丙烯酰胺(DMMA)、2-丙烯酰氨基羟基乙酸一水合物、3-丙烯酰氨基-1-丙醇、N-羟乙基丙烯酰胺、N-[三(羟甲基)甲基]-丙烯酰胺、N-甲基-3-亚甲基-2-吡咯烷酮、甲基丙烯酸2-羟基乙酯(HEMA)、丙烯酸2-羟基乙酯(HEA)、丙烯酸羟基丙酯、甲基丙烯酸羟基丙酯(HPMA)、三甲基铵甲基丙烯酸2-羟基丙酯盐酸盐(trimethylammonium 2-hydroxypropylmethacrylate hydrochloride)、甲基丙烯酸氨基丙酯盐酸盐(aminopropyl methacrylate hydrochloride)、甲基丙烯酸二甲基氨基乙酯(DMAEMA)、甲基丙烯酸甘油酯(GMA)、N-乙烯基-2-吡咯烷酮(NVP)、烯丙醇、乙烯基吡啶、丙烯酸、具有200-1500的重均分子量的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯如聚(乙二醇)甲基醚甲基丙烯酸酯、甲基丙烯酸、N-乙烯基甲酰胺、N-乙烯基乙酰胺、N-乙烯基异丙酰胺、N-乙烯基-N-甲基乙酰胺、烯丙醇、N-乙烯基己内酰胺及其混合物。
接枝步骤可进一步在亲水性乙烯单体和交联剂的存在下，或者在单独交联剂的存在下进行，条件是交联剂为亲水性的。这类交联剂具有至少2个烯属不饱和基团，并且可以为交联试剂(即包含2个或更多个烯属不饱和基团且具有70道尔顿或更小的分子量的化合物)。
亲水性乙烯单体和优选的这类单体的实例提供于前文中。尤其优选具有200-1500的重均分子量的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯如聚(乙二醇)甲基醚甲基丙烯酸酯。
优选的交联试剂的实例包括但不限于四(乙二醇)二丙烯酸酯、三(乙二醇)二丙烯酸酯、乙二醇二丙烯酸酯、二(乙二醇)二丙烯酸酯、四乙二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯、乙二醇二甲基丙烯酸酯、二(乙二醇)二甲基丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、季戊四醇四甲基丙烯酸酯、双酚A二甲基丙烯酸酯、甲基丙烯酸乙烯酯、乙二胺二甲基丙烯酰胺、甘油二甲基丙烯酸酯、异氰尿酸三烯丙酯、氰尿酸三烯丙酯、甲基丙烯酸烯丙酯、美国专利No.4,711,943(通过引用将其全部并入本文中)中公开的二聚物(例如1,3-双(甲基丙烯酰氨基丙基)-1,1,3,3-四(三甲基-甲硅烷氧基)二硅氧烷、1,3-双(N-甲基丙烯酰氨基丙基)-1,1,3,3-四-(三甲基甲硅烷氧基)二硅氧烷、1,3-双(甲基丙烯酰氨基丁基)-1,1,3,3-四(三甲基甲硅烷氧基)-二硅氧烷、1,3-双(丙烯酰胺-丙基)-1,1,3,3-四(三甲基甲硅烷氧基)二硅氧烷、1,3-双(甲基丙烯酰氧基乙基脲基丙基)-1,1,3,3-四(三甲基甲硅烷氧基)二硅氧烷)(1,3-bis(methacryloxyethylureidopropyl)-1,1,3,3-tetrakis-(trimethylsiloxy)disiloxane))、例如如WO02/071106中公开并在其中例示的丙烯酰胺改性聚乙烯醇及其组合。优选的交联剂为聚(乙二醇)二丙烯酸酯、四(乙二醇)二丙烯酸酯、三(乙二醇)二丙烯酸酯、乙二醇二丙烯酸酯、二(乙二醇)二丙烯酸酯、异氰尿酸三烯丙酯或氰尿酸三烯丙酯。甚至更优选的交联试剂为聚(乙二醇)二丙烯酸酯(Mn约700道尔顿，Aldrich#455008)和丙烯酰胺改性聚乙烯醇，例如如WO02/071106的实施例2中所公开的。
根据本发明，加热优选通过在密封透镜包装中在约118℃至约125℃的温度下将其上具有UV吸收涂层的接触透镜在包含水溶性热可交联亲水性聚合材料的包装溶液(即缓冲水溶液)中压热器处理约20-90分钟而进行。根据本发明这一实施方案，包装溶液为在压热器处理以后眼用安全的缓冲水溶液。作为选择，优选通过将在密封透镜包装中浸入包装溶液(即缓冲水溶液)中的包含UV吸收涂层的接触透镜在约118℃至约125℃的温度下压热器处理约20-90分钟而进行。
透镜包装(或容器)是本领域技术人员熟知用于压热器处理和储存软接触透镜的。任何透镜包装可用于本发明中。优选透镜包装为泡罩包装，其包含基底和覆盖物，其中覆盖物可拆卸地密封基底，其中基底包括用于接纳灭菌包装溶液和接触透镜的空穴。
在分配给使用者以前将透镜封装在单独的包装中，密封并灭菌(例如在约120℃或更高下压热器处理至少30分钟)。本领域技术人员应当理解如何将透镜包装密封和灭菌。
根据本发明，包装溶液含有至少一种缓冲剂以将包装溶液的pH保持在约6至约8.5的生理可接受范围内，一种或多种其它张力剂(tonicity agent)以提供约200至约450毫渗克分子(milliosmol，mOsm)，优选约250至约350mOsm的张力，和本领域技术人员已知的其它成分。其它成分的实例包括但不限于表面活性剂/润滑剂、抗菌剂、防腐剂和水溶性增粘剂(例如纤维素衍生物、聚乙烯醇、聚乙烯基吡咯烷酮)。
生理相容性缓冲剂为硼酸、硼酸盐如硼酸钠、柠檬酸、柠檬酸盐如柠檬酸钾、碳酸氢盐如碳酸氢钠、TRIS(2-氨基-2-羟基甲基-1,3-丙二醇)、Bis-Tris(双-(2-羟乙基)-亚氨基-三-(羟甲基)-甲烷)、双氨基多元醇、三乙醇胺、ACES(N-(2-羟乙基)-2-氨基乙磺酸)、BES(N,N-双(2-羟乙基)-2-氨基乙磺酸)、HEPES(4-(2-羟乙基)-1-哌嗪乙磺酸)、MES(2-(N-吗啉)乙磺酸)、MOPS(3-[N-吗啉]-丙磺酸)、PIPES(哌嗪-N,N’-双(2-乙磺酸)、TES(N-[三(羟甲基)甲基]-2-氨基乙磺酸)、其盐、磷酸盐缓冲剂如Na2HPO4、NaH2PO4和KH2PO4或其混合物。优选的双氨基多元醇为1,3-双(三[羟甲基]-甲基氨基)丙烷(双-TRIS-丙烷)。包装溶液中各缓冲剂的量优选为0.001-2％，优选0.01-1％；最优选约0.05至约0.30重量％。
合适的眼睛可接受张力剂包括但不限于氯化钠、氯化钾、甘油、丙二醇、多元醇、甘露糖醇、山梨糖醇、木糖醇及其混合物。
本发明包装溶液具有在25℃下约1至约20厘泊，优选约1.2至约10厘泊，更优选约1.5至约5厘泊的粘度。
在优选实施方案中，本发明方法进一步包括以下步骤：将接触透镜浸入具有蓝光吸收性单体单元和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元的蓝光吸收聚合物溶液中。术语“蓝光吸收性单体单元”指各自包含蓝光吸收性结构部分的聚合物的重复单元。“蓝光吸收性结构部分”指可使含有这类基团的化合物吸收约400至约480nm的区域内的光的有机基团。一个优选的蓝光吸收性结构部分为硝基苯基吡咯烷基团。蓝光吸收性聚合物可根据类似于以上关于UV吸收性聚合物所述那些程序制备。例如，蓝光吸收聚合物可通过使包含至少一种含羧基乙烯单体(上述那些中的任一种)和至少一种蓝光吸收性乙烯单体的可聚合混合物聚合，或者作为选择通过使具有反应性官能团(例如氨基、吖内酯基团、环氧基、异氰酸酯基团、吖丙啶基团及其组合，其中氨基是最优选的反应性官能团)的蓝光吸收性化合物与包含羧基和任选氨基的前体聚合物(以上关于制备UV吸收性聚合物所述那些中的任一种)反应而制备。
在另一优选实施方案中，根据本发明方法得到的接触透镜，优选硅氧烷水凝胶接触透镜具有特征是具有约90°或更小，优选约80°或更小，更优选约70°或更小，甚至更优选约60°或更小，最优选约50°或更小的平均水接触角的表面润湿性。
应当理解尽管在本发明这一方面，上文中可分别描述本发明的各个实施方案，包括优选实施方案，它们可以以任何理想的方式组合和/或一起使用以达成本发明接触透镜的不同实施方案。
另一方面，本发明提供眼用透镜，所述透镜包含：聚合物透镜体；在透镜体上的UV吸收性聚合物层；和接枝在UV吸收性聚合物层上的水凝胶，其中UV吸收性聚合物包含UV吸收性单体单元和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％(以摩尔计)含羧基单体单元，其中水凝胶接枝通过光引发接枝方法得到，所述光引发接枝方法可通过在亲水性乙烯单体或交联剂的存在下照射共价结合自由基引发结构部分而进行。
上文关于本发明先前方面所述的各个实施方案中的所有都可单独或一任何组合用于本发明这一方面中。
先前的公开内容能使本领域技术人员实践本发明。可作出对本文所述各个实施方案的各种改进、变化和组合。为了更好地使读者理解具体实施方案及其优点，提出对以下实施例的参考。说明书和实施例意欲被认为是示例性的。
尽管已使用了具体术语、器件和方法描述了本发明的各个方面和各个实施方案，但这种描述仅用于说明目的。所用措辞为描述而不是限制性措辞。应当理解本领域技术人员可不偏离以下权利要求书所述本发明精神或范围地作出改变和变化。另外，应当理解各个实施方案的方面可全部或部分地互换或可以以任何方式组合和/或一起使用。因此，所附权利要求书的精神和范围应不限于本文所含优选变化方案的描述。
实施例：一般注释
透氧性测量。透镜的表观透氧性和透镜材料的氧气透过率根据类似于美国专利No.5,760,100和Winterton等人的文章，(The Cornea：Transactions of the World Congress on the Cornea 111，H.D.CavanaghEd.，Raven Press：New York 1988，第273-280页)所述的技术测定，通过引用将二者的全部内容并入本文中。氧通量(J)使用Dk1000仪器(可由Applied Design and Development Co.,Norcross，GA得到)或类似的分析仪器在湿池(即将气流保持在约100％相对湿度下)中在34℃下测量。使具有已知百分数的氧气(例如21％)的空气流以约10-20cm3/min的速率通过透镜的一面，同时使氮气流以约10-20cm3/min的速率通过透镜的相对面。在测量以前将试样在规定试验温度下在试验介质(即盐水或蒸馏水)中平衡至少30分钟但不大于45分钟。在测量以前将作为重叠层使用的任何试验介质在规定试验温度下平衡至少30分钟但不大于45分钟。搅拌电机速度设置为1200±50rpm，相当于步进式电机控制器上400±15的指定设置。测量围绕系统的大气压P测量。暴露用于测试的面积中透镜的厚度(t)通过用Mitotoya测微计VL-50或类似仪器测量约10个位置并将测量值求平均而测定。氮气流中的氧气(即扩散通过透镜的氧气)浓度使用DK1000仪器测量。透镜材料的表观透氧性Dk表观由下式测定：
Dk表观＝Jt/(P氧气)
其中J＝氧通量[微升O2/cm2–分钟]
P氧气＝(P测量-P水蒸气)＝(空气流中的％O2)[mm Hg]＝空气流中的氧分压
P测量＝大气压(mm Hg)
P水蒸气＝在34℃下0mm Hg(在干池中)(mm Hg)
P水蒸气＝在34℃下40mm Hg(在湿池中)(mm Hg)
t＝暴露的试验面积上透镜的平均厚度(mm)
Dk表观以Barrer为单位表示。
材料的表观氧气透过率(Dk/t)可通过将表观透氧性(Dk表观)除以透镜的平均厚度(t)计算。
上述测量不对所谓的边界层效应校正，所述边界层效应可归因于氧通量测量期间在接触透镜顶部的水或盐水浴的使用。边界层效应导致关于硅氧烷水凝胶材料的表观Dk的报告值低于实际本征Dk值。另外，边界层效应的相对影响对于较薄的透镜比对较厚的透镜更大。当它应保持恒定时，净效果是报告的Dk显现出作为透镜厚度的函数变化。
透镜的本征Dk值可如下基于关于边界层效应导致的氧通量的表面阻力(surface resistance)校正的Dk值评估。
使用相同设备测量参比lotrafilcon A(来自CIBA VISIONCORPORATION的N&)或lotrafilcon B(来自CIBA VISIONCORPORATION的AirOptixTM)透镜的表观透氧性值(单点)。参比透镜具有与试验透镜类似的屈光力并与试验透镜同时测量。
使用相同设备根据上述用于表观Dk测量的程序测量通过厚度系列的lotrafilcon A或lotrafilcon B(参比)透镜的氧通量以得到参比透镜的本征Dk值(Dki)。厚度系列应涵盖约100μm或更大的厚度范围。优选，参比透镜厚度的范围包括试验透镜厚度。这些参比透镜的Dk表观必须在与试验透镜相同的设备上测量并应理想地与试验透镜同时测量。设备设置和测量参数应在整个实验中保持恒定。如果需要的话可将各个试样测量多次。
在计算中使用方程式1由参比透镜结果测定残余氧阻力值(residualoxygen resistance value)Rr。
其中t为试验透镜(即也指参比透镜)的厚度，且n为测量的参比透镜的数目。绘出残余氧阻力值Rr相对于t数据，并拟合具有形式Y＝a+bX的曲线，其中对于jth透镜，Yj＝(ΔP/J)j且X＝tj。残余氧阻力Rr等于a。
基于方程式2使用以上测定的残余氧阻力值计算试验透镜的校正透氧性Dkc(估算的本征Dk)。
Dkc＝t/[(t/Dka)-Rr] (2)
试验透镜的估算本征Dk可用于基于方程式3计算在相同试验环境中标准厚度透镜的表观Dk(Dka_标准)。lotrafilcon A的标准厚度(t标准)＝85μm。lotrafilcon B的标准厚度＝60μm。
Dka_标准＝t标准/[(t标准/Dkc)+Rr_标准] (3)
离子渗透性测量。透镜的离子渗透性根据美国专利No.5,760,100(通过引用将其全部内容并入本文中)所述程序测量。以下实施例中报告的离子渗透性值为关于作为参比材料的透镜材料Alsacon的相对ionoflux扩散系数(D/Dref)。Alsacon具有0.314×10-3mm2/min的ionoflux扩散系数。
表面润湿性试验。接触透镜上的水接触角是接触透镜的表面润湿性的一般测量。特别是，低水接触角相当于更可润湿的表面。接触透镜的平均接触角(座滴法)使用来自位于Boston，Massachusetts的AST，Inc.的VCA2500XE接触角测量设备测量。该设备能够测量前进或后退接触角或座滴(静)接触角。测量如下在完全水化的接触透镜上且在沾污-干燥以后立即进行。将接触透镜从小瓶中取出并在～200ml新鲜去离子水中洗涤3次以从透镜表面上除去疏松地结合的包装添加剂。然后将透镜放在无绒清洁布(Alpha Wipe TX1009)上，好好地轻拍以除去表面水，安装在接触角测量台架上，用干空气鼓风吹干，最后使用生产商提供的软件自动测量座滴接触角(sessile drop contact angle)。用于测量接触角的去离子水具有>18MΩcm的电阻率，且所用液滴体积为2μl。通常，未涂覆的硅氧烷水凝胶透镜(在压热器处理以后)具有约120度的座滴接触角。在与接触透镜接触以前将镊子和台架用异丙醇良好地洗涤并用去离子水冲洗。
涂层完整性试验。接触透镜表面上亲水性涂层的完整性可如下根据苏丹黑染色试验测试。将具有亲水性涂层(LbL涂层、等离子体涂层或任何其它涂层)的接触透镜浸入苏丹黑染料溶液(苏丹黑在维生素E油中)中，然后用水充分冲洗。苏丹黑染料为疏水性的，且具有被疏水性材料吸收或吸收到疏水透镜表面或疏水透镜(例如硅氧烷水凝胶接触透镜)的部分涂覆表面上的疏水点上。如果疏水透镜上的亲水性涂层是完整的，则在透镜上或透镜中应观察不到染色点。测试的所有透镜为完全水化的。如果测试的接触透镜具有疏水性透镜表面或在疏水性透镜的部分涂覆表面上的疏水点，则接触透镜被染色或者在透镜上或透镜中可观察到染色点。
涂层耐久性试验。将透镜用多功能透镜护理液手指摩擦30次，然后用盐水冲洗。将以上程序重复给定次数，例如1-30次(即模拟清洁和浸泡循环的连续手指摩擦试验的数目)。然后使透镜经受苏丹黑试验(即上述涂层完整性试验)以检查亲水性涂层是否仍完整。为经得住手指摩擦试验，不存在显著提高的染色点(例如染色点覆盖总透镜表面积的不大于约5％)。测量水接触角以测定涂层耐久性。
其它使用仪器：1H-NMR光谱研究用Bruker Avance 400NMR谱仪进行。对于UV-Vis光谱研究，使用Perkin Elmer Lambda 25分光计。透镜光谱在PBS溶液(pH＝7.0)中在石英比色皿(长度：1cm)中记录。在从包装中取出时在石英比色皿(长度也是1cm)中记录包装溶液的光谱。
实施例1
CE-PDMS大单体的制备。在第一步骤中，通过使49.85g的α,ω-双(2-羟基乙氧基丙基)-聚二甲基硅氧烷与11.1g IPDI在150g干甲乙酮(MEK)中在0.063g二月桂酸二丁锡(DBTDL)的存在下反应而将α,ω-双(2-羟基乙氧基丙基)-聚二甲基硅氧烷(Mn＝2000，Shin-Etsu，KF-6001a)用异佛尔酮二异氰酸酯(IPDI)封端。将反应在40℃下保持4.5小时，形成IPDI-PDMS-IPDI。在第二步骤中，将164.8gα,ω-双(2-羟基乙氧基丙基)-聚二甲基硅氧烷(Mn＝3000，Shin-Etsu，KF-6002)与50g干MEK的混合物逐滴加入IPDI-PDMS-IPDI溶液中，已向其中加入另外0.063g DBTDL。将反应器保持在约40℃下4.5小时，形成HO-PDMS-IPDI-PDMS-IPDI-PDMS-OH。然后在降低的压力下除去MEK。在第三步骤中，通过加入7.77g甲基丙烯酸异氰酸酯基乙酯(isocyanatoethylmethacrylate，IEM)和另外0.063g DBTDL而将末端羟基用甲基丙烯酰氧基乙基封端，形成IEM-PDMS-IPDI-PDMS-IPDI-PDMS-IEM(即用甲基丙烯酸酯基团封端的CE-PDMS)。
透镜配制剂的制备。透镜配制剂通过将组分溶于1-丙醇中以具有如下组成而制备：33重量％的该实施例中制备的CE-PDMS大单体、17重量％N-[三(三甲基甲硅烷氧基)-甲硅烷基丙基]丙烯酰胺(TRIS-Am)、24重量％N,N-二甲基丙烯酰胺(DMA)、0.5重量％N-(羰基-甲氧基聚乙二醇-2000)-1,2-二硬脂酰-sn-甘油-3-磷乙醇胺钠盐(N-(carbonyl-methoxypolyethylene glycol-2000)-1,2-disteaoyl-sn-glycero-3-phospho-ethanolamin,sodium salt))(L-PEG)、1.0重量％Darocur 1173(DC1173)、0.1重量％visitint(在三(三甲基甲硅烷氧基)甲硅烷基丙基甲基丙烯酸酯，TRIS中的5％酞菁铜蓝颜料分散体)和24.5重量％1-丙醇。
透镜的制备。透镜通过在类似于美国专利No.7,384,590的图1-6和7,387,759(图1-6)所示模具的可重复使用模具中由以上制备的透镜配制剂铸造模塑而制备。模具包含由CaF2构成的阴半模和由PMMA构成的阳半模。UV辐射源为具有WG335+TM297截止滤光器、约4mW/cm2的强度的Hamamatsu灯。将模具中的透镜配制剂用UV辐射照射约25秒。
将铸造模塑的透镜脱模并作为所谓的“实施例1的未提取接触透镜”用于实施例中。
作为选择，将铸造模塑的透镜用异丙醇(或甲乙酮，MEK)提取，用水冲洗，通过将透镜浸入PAA的丙醇溶液(0.1重量％，用甲酸酸化至约pH 2.5)中而用聚丙烯酸(PAA)涂覆，并在水中水化。测定其上具有反应性PAA-LbL底涂层的所得接触透镜具有如下性能：相对于Alsacon透镜材料约8.0至约9.0的离子渗透率；约90-100的表观Dk(单点)；约30至约33％的水含量；和约0.60MPa至约0.65MPa的体弹性模量(bulk elastic modulus)。
实施例2
聚(丙烯酸-共聚-Norbloc)(PAA-N20)的制备。该实施例阐述如何制备其上具有UV吸收涂层的接触透镜。丙烯酸由Fluka提供(#017309111)。
指定为PAA-N20的式(2)UV吸收性聚合物(其中m:n～80:20)具有约36kD的分子量且包含约8.1摩尔％UV吸收性单体单元(Norbloc，甲基丙烯酸[3-(2-H-苯并三唑-2-基)-4-羟基苯基]乙酯。它根据下文所述程序制备。
向装配有N2入口管、冷凝器、温度计和磁力棒的250ml三颈烧瓶中放入8,00g丙烯酸(111毫摩尔；Fluka#017309111)、2,00g甲基丙烯酸([3-(2-H-苯并三唑-2-基)-4-羟基苯基]乙酯(Norbloc 7966；6.2毫摩尔；Aldrich#22,-705-6)和100ml N,N-二甲基甲酰胺(DMF；Aldrich，#227056)的混合物。引导氮气通过该溶液以使溶液不含空气。然后随着搅拌加热至60℃，加入0.5ml的4％2,2’-偶氮双-异丁酸二甲酯(V-601，Wako#927-14717)的DMF溶液。通过经16小时时间搅拌而将反应混合物保持在60℃，冷却至环境温度，并倒入1.0L乙酸乙酯中。将所得沉淀物通过离心分离(6000min-1，30min)，再溶于轻微碱性水溶液(pH＝10.0，用碳酸钠调整)中并相对于去离子水超滤(3kDa膜，Millipore#P2PLBCV01；水15倍体积交换)。在将溶液冻干以后，分离7.0g白色固体产物。
1H-NMR(400MHz；D2O)δ：0.8-3.15(最大值在1.06，1.52，1.62，2.15，2.57处)，4.25，6.5-8.1(H芳族)ppm；所有信号是无结构且宽的。
共聚物PAA-N20中Norbloc单体单元的摩尔百分数根据以下方程式基于1H-NMR积分为XNorbloc＝8.1[摩尔％]：
XNorbloc[摩尔％]＝100×[3×A芳族/(7×A1-4×A芳族)]
其中A1为1.02-3,15ppm的质子的区域的积分，且A芳族为6.5-8.15ppm的芳族信号的区域的积分。
UV-Vis吸光度(pH7.0的PBS溶液)：两个最大值：吸收系数ε1(299nm)＝9.09和ε2(329nm)＝8.86[l/(g×cm)]。
通过GPC得到的分子量(具有和孔径大小的PSS Suprema柱；PBS溶液作为洗脱液；聚(丙烯酸)钠作为校准基准)：Mw＝36kda。
PAA-N20涂覆接触透镜的制备。将实施例1的未提取接触透镜浸入PAA-N20溶液(溶于1-丙醇中的0.36g/L PAA-N20，用HCOOH将pH调整至约2.0)中约30分钟，然后用磷酸盐缓冲盐水溶液(PBS)冲洗并储存于其中。所得其上具有PAA-N20涂层的接触透镜的UV光谱清楚地显示透镜的透光性在UV-B和UV-A区域(即280nm至380nm的区域)中有效地被阻断。
实施例3
PAA-N20-Irg的制备：通过搅拌将1.00g(14毫摩尔)PAA-N20(Mw＝36kD；根据前文实施例制备)溶于75ml水中。在环境温度下向该溶液中加入各2ml的1-(3-二甲基氨基丙基)-3-乙基碳二亚胺-盐酸盐(w＝23％，EDC-HCl；Fluka#03450)、N-羟基磺基-琥珀酰亚胺钠盐(w＝24％；NHS；Aldrich#341851)的水溶液，在15分钟以后加入1.48g(5.7毫摩尔)固体2-羟基-2-甲基-1-[4-(2-羟乙基氨基)乙氧基]苯基-1-丙酮(Irgacure-胺；根据WO 03/042724，实施例A-1，第24页制备)。在Irgacure-胺完全溶解以后，通过1N NaOH水溶液将溶液的pH调整至9.0。在21小时以后，将清澈的溶液用1N盐酸中和，相对于去离子水超滤(1kD膜，Millipore#P2PLACV01，水10倍体积交换)并浓缩。在将所得溶液冻干以后，分离1.19g白色固体材料。
1H-NMR(400MHz，D2O)δ：0.9-2.6(最大值在1.00，1.45，1.61，1.81，2.11，2.52处)，2.81(s；对应于EDC-HCl：-N(CH 3)，2.97-3.17，3.23，3.46，3.77，3.83，3.9-4.3(最大值在4.20和4,27处)，6.7-7.8(最大值在6.87和6.89处，H芳族)，7.91(d，对应于Irgacure-胺：H芳族)。
1-H-NMR积分提供关于聚合物PAA-N20-Irg的以下组成：77摩尔％具有丙烯酸结构部分的重复单元，8摩尔％具有Norbloc，7摩尔％具有光引发剂，8摩尔％具有EDC作为来源的结构部分。
UV-Vis吸光度(pH 7.0的PBS溶液)：两个最大值：吸收系数ε1(287nm)＝10.81[l/(g×cm)]和ε2(327nm)＝6,46[l/(g×cm)]。
通过GPC得到的分子量(具有和孔径大小的PSS Suprema柱；PBS溶液作为洗脱液；聚(丙烯酸)钠作为校准基准)：Mw＝34kD。
实施例4
PAA-N75-V15的制备：将2.54g(35.2毫摩尔)丙烯酸、0.86g(2.7毫摩尔)Norbloc 7966和2.28g(5.0毫摩尔)2-(2-丙烯基-氨基)-2-甲基丙酸4-(2-羟基-2-甲基丙酰基)苯氧基乙酯[VDM；制备：G.N.Babu等人，ACS PolymerPreprints，38(1997)，510]与63ml N,N-二甲基甲酰胺(Sigma-Aldrich#227056)一起放入烧瓶中。将氩气引导通过该溶液以使溶液不含空气。然后通过搅拌将它加热至60℃并加入0.008g(0.03毫摩尔)2,2’-偶氮双异丁酸二甲酯(V-601，Wako#927-14717)。经16小时时间通过搅拌将反应混合物保持在60℃下。然后通过真空蒸馏除去50ml DMF并将残余溶液倒入200ml乙酸乙酯中。将所得沉淀物通过离心分离，再溶于轻微碱性水溶液(pH＝10.0，用碳酸氢钠调整)中并相对于去离子水超滤(1kD膜，Millipore#P2PLACV01；水10倍体积交换)。在将溶液冻干以后，分离1.41g白色固体材料。
1-H-NMR(400MHz，D2O)δ：0.5-3.2(最大值在1.04，1.40，1.70，2.17，2.56，2.77处)，3.7-4.5(最大值在4.21处；对应于VDM的O-CH 2 CH 2 -O和Norbloc的–CH2CH 2-O)，6.25-8.25(最大值在7.01，7.35，8,17处；对应于VDM的4H芳族和Norbloc的7H芳族)。
1-H-NMR积分提供关于聚合物PAA-N75-V15的以下组成：75摩尔％具有丙烯酸结构部分，15摩尔％具有Norbloc，10摩尔％具有光引发剂。因此，PAA-N75-V15可由下式2表征：
其中m:n:o的比为75:15:10。
UV-Vis吸光度(pH 7.0的PBS溶液)：两个最大值：吸收系数ε1(294nm)＝13.83[l/(g×cm)]和ε2(334nm)＝11.27[l/(g×cm)。
通过GPC得到的分子量(具有和孔径大小的PSS Suprema柱；PBS溶液作为洗脱液；聚(丙烯酸)钠作为校准基准)：Mw＝6.2kD。
实施例5、制备具有蓝光吸收剂的光引发剂：
PAA-L20-IA15的制备：2.04g(27.7毫摩尔)丙烯酸、0.77g(S)-2-甲基丙烯酰氧基甲基-1-(4-硝基苯基)吡咯烷酮(1.6毫摩尔；根据M.Yoshida等人；Makromol.Chem.Rapid Commun.，10，(1989)，517制备)、1.14g丙烯酸2-[4-(2-羟基-2-甲基丙酰基)苯氧基]乙酯(4.1毫摩尔；根据WO2010/0635355，第24页制备)与40ml N,N-二甲基甲酰胺(Sigma-Aldrich#227056)一起放入烧瓶中。引导氮气通过该溶液以使溶液不含空气。然后通过搅拌将它加热至60℃，并加入0.006g(0.02毫摩尔)2,2’-偶氮双异丁酸二甲酯(V-601，Wako#927-14717)。经18小时时间通过搅拌将反应混合物保持在60℃。然后将该溶液倒入400ml乙酸乙酯中。将所得沉淀物通过离心分离，再溶于轻微碱性水溶液(pH＝10.0，用碳酸氢钠调整)中并相对于去离子水超滤(1kD膜，Millipore#P2PLACV01；水10倍体积交换)。在将溶液冻干以后，分离0.82g黄色固体材料。
1-H-NMR(400MHz，D2O)δ：05-2.7(最大值在1.00，1.45，2.00，2.50处)，2.8-3.65(最大值在3.24，3.57处；对应于“蓝光”吸收剂的吡咯烷环的4个质子)，3.7-4.6(最大值在4.18，4.36处)，6.1-8.2(最大值在6,47，6.78，7.06，7.87，8.04处；对应于光引发剂子单元的4H芳族和蓝光吸收剂的4H芳族)。
1-H-NMR积分提供关于聚合物PAA-L20-IA15的以下组成：85摩尔％具有丙烯酸结构部分，9摩尔％具有蓝光吸收剂，6摩尔％具有光引发剂。因此，PAA-L20-IA15可由下式4表征：
其中m:n:o的比为85:9:6。
UV-Vis吸光度(pH 7.0的PBS溶液)：三个最大值：吸收系数ε1(223nm)＝8.31[l/(g×cm)，ε2(277nm)＝8.22[l/(gx cm)]和ε2(415nm)＝10.43[l/(g×cm)。
通过GPC得到的分子量(具有和孔径大小的PSS Suprema柱；PBS溶液作为洗脱液；聚丙烯酸钠作为校准基准)：Mw＝22.2kD。
实施例6、浸渍溶液的生产和浸渍方法
浸渍溶液：PAA-N20浸渍溶液通过将PAA-N20(0.36％)溶于1-丙醇/水混合物(4％)中并通过加入甲酸酸化至pH＝2而制备。
PAA-N20-Irg浸渍溶液通过将PAA-N20-Irg(0.36％)溶于EtOH中并通过加入盐酸的乙醇溶液(Fluka#17934)将溶液酸化至pH＝2而制备。
PAA-N75-V15浸渍溶液通过将PAA-N75-V15(0.36％)溶于1-丙醇中并通过加入盐酸的丙醇溶液(Fluka#17933)将溶液酸化至pH＝2.0而制备。
PAA-L20-IA15浸渍溶液通过将PAA-L20-IA15(0.36％)溶于1-丙醇中并通过加入盐酸的丙醇溶液将溶液酸化至pH＝2.0而制备。
浸渍方法：将实施例1透镜的未提取接触透镜放入夹持装置(holder)中并用合适的浸渍溶液处理。在透镜在其315nm(局部最小值)下的UV光谱(在PBS溶液中记录)中显示出UV吸光度(A)≥2时停止处理。然后将透镜用去离子水冲洗(6min)，随后用PBS溶液冲洗(1min)。
实施例7
透镜的UV后处理/光引发接枝：所有步骤在N2气氛下进行。向具有根据实施例6用合适的浸渍溶液处理的实施例1的未提取接触透镜的石英比色皿中倒入合适的UV处理溶液(参见下文)(约1.5ml/透镜)。在5分钟以后，将透镜通过垂直于透镜表面但彼此相对排列的2个光波导，用来自装配有328nm边缘滤光器的Hamamatsu UV光源的UV光(强度：5,8mW/cm2每光波导)照射5分钟。然后将透镜从固化溶液中取出，用水冲洗，与PBS储液一起封装在PP壳中，用箔密封并压热器处理。
作为UV处理溶液，使用：i)PBS溶液(pH＝7.0)，ii)聚(乙二醇)二丙烯酸酯的PBS缓冲(pH＝7.0)水溶液(PEG-DA 700；10％；Mn＝700D；Aldrich#455008)，iii)聚(乙二醇)甲基醚甲基丙烯酸酯的PBS缓冲(pH＝7.0)水溶液(PEG-MEMA 950；10％；Mn＝950；Aldrich#447951)，和iv)下文式3的聚乙烯醇的PBS缓冲(pH＝7.0)水溶液(PVA；10％；根据WO02/071106的实施例2制备)：
实施例8
将实施例1的未提取接触透镜根据实施例6用PAA-N20浸渍溶液处理并根据实施例7在PBS溶液中UV处理。相应PBS储液的UV光谱公开于图1中，指定为1)的吸收线。
实施例9
将实施例1的未提取接触透镜根据实施例6用PAA-N20-Irg浸渍溶液处理并根据实施例7在PBS溶液中UV照射。相应PBS储液的UV光谱公开于图1中，指定为2)的吸收线。
实施例10
将实施例1的未提取接触透镜根据实施例6用PAA-N20-Irg溶液处理并根据实施例7在PEG-DA 700溶液中UV照射。相应PBS储液的UV光谱公开于图1中，指定为3)的吸收线。
从图1中获悉存在UV吸收性聚合物从实施例8的透镜中实质性的再迁移。所述再迁移由根据本发明方法得到的透镜降低。实施例9的透镜关于图1证明了这一点。尽管具有和不具有UV光引发剂的UV吸收性聚合物的类似分子量，实施例9的透镜的储液的UV吸光度明显低于实施例8的透镜的。用在PEG-DA 700溶液中照射的实施例10的透镜实现了透镜中UV吸收性官能化共聚物的完全阻断。在将透镜压热器处理以后，在其储液的UV光谱中没有检测到属于再迁移(沥滤)的UV吸收性聚合物的信号。
实施例11
用于对比的未处理透镜(这些为实施例1的未提取接触透镜，然后提取但不浸涂或另外处理)。
实施例12
将实施例1的未提取接触透镜根据实施例6用PAA-N20-Irg浸渍溶液处理20分钟并根据实施例7在PVA溶液中UV照射。这样处理的透镜的ATR-FTIR光谱显示对应于PVA的信号。
实施例13
将实施例1的未提取接触透镜根据实施例6用PAA-N75-V15溶液处理15分钟并根据实施例7在PBS溶液中UV照射。
实施例14
将实施例1的未提取接触透镜根据实施例6用PAA-N75-V15溶液处理15分钟并根据实施例7在PEG-DA700溶液中UV照射。这样处理的透镜的ATR-FTIR光谱显示出对应于PEG-DA 700的信号。
实施例15
将实施例1的未提取接触透镜根据实施例6用PAA-N75-V15溶液处理15分钟并根据实施例7在PEG-MEMA 950溶液中UV照射。这样处理的透镜的ATR-FTIR光谱显示出对应于PEG-MEMA 950的信号。
实施例16
将实施例1的未提取接触透镜根据实施例6用PAA-N75-V15溶液处理15分钟并根据实施例7在PVA溶液中UV照射。这样处理的透镜的ATR-FTIR光谱显示出对应于PVA的信号。
实施例17
这是对照实验以证明不具有UV引发剂官能的PAA-Norbloc共聚物不能通过UV处理接枝亲水性聚合物：将实施例1的未提取接触透镜根据实施例6用PAA-N20溶液处理并根据实施例7在PVA溶液中UV照射。在pH＝2.0下水接触角从16°提高至92°以及在pH＝2.0下透镜被苏丹黑完全染色表明不存在PVA层。该观察也由ATR-FTIR测量证实：不能检测到对应于PVA的信号。这意指反应性涂层的接枝不能由包含单独聚丙烯酸聚合物的UV吸收剂引发，而是需要在光引发剂的存在下成功接枝在聚合物上。
实施例18
该实验证明所公开的涂覆方法用具有大单体作为本体透镜材料的硅氧烷水凝胶透镜也起作用。将根据WO 2008/074838的实施例2ia-id制备的大单体透镜根据实施例6用PAA-N75-V15溶液处理25分钟并根据实施例7在PVA溶液中UV照射。
实施例19
制备具有UV和蓝光吸收剂并在式3的PVA的存在下后固化的透镜。将实施例1的未提取接触透镜根据实施例6首先用PAA-N75-V15溶液处理15分钟，其次用PAA-L20-IA15溶液处理15分钟。然后将如此处理的透镜根据实施例7在PVA溶液中照射。所得透镜具有强烈的黄色。这也反映于其UV光谱中，显示降至零的约420nm波长的透射率。这样处理的透镜的ATR-FTIR光谱显示出对应于PVA的信号。
表1：从包装中取出并且i)用水(pH＝7.0)冲洗和ii)用pH＝2.0的酸化水冲洗的透镜的水接触角和苏丹黑染色试验
*)评估值：0：无；1：轻微；2：透镜完全被苏丹黑溶液染色
**)由于透镜的强烈黄色，苏丹黑染色透镜显示出绿色而不是蓝色！
实施例20
用于测定透镜提取物的程序：将20个各自如下文所列实施例的透镜从它们的包装中取出，放在玻璃烧瓶中并用水冲洗，条件是除去PBS缓冲剂的无机盐。然后将透镜干燥，称重(mo)，提供2-丙醇(40ml；Fluka，#34965)并放在实验室振动器上。在环境温度下处理4小时以后，完全除去提取溶液并将透镜用新鲜2-丙醇冲洗几次。将透镜再次干燥并称重(me)。提取物根据提取物＝100×(mo-me)/mo[透镜的重量％]计算。
表2：透镜提取物
实施例21
测量PBS储液在329nm下的UV吸光度(在329nm下的吸光度对应于在压热器处理和储存以后在储液中从透镜中释放/再迁移的含Norbloc化合物；吸光度越高，不想要的释放越高)。
表3：UV吸光度
| UV吸光度x) | |
| 实施例8(PAA-N20) | 1.66 |
| 实施例9(PAA-N20-Irg，hν) | 0.33 |
| 实施例10(PAA-N20-Irg，PEG-DA 700，hv) | 0.00 |
| 实施例12(PAA-N20-Irg，PVA，hν) | 0.12 |
| 实施例13(PAA-N75-V15，hν) | 0.58 |
| 实施例14(PAA-N75-V15，PEG-DA 700，hν) | 0.07 |
| 实施例15(PAA-N75-N15，PEG-MEMA 950，hν) | 0.11 |
| 实施例16(PAA-N75-V15，PVA，hν) | 0.06 |
| 实施例17(PAA-N20，PVA，hν) | 1.28 |
| 实施例18(大单体透镜，N75-V15，PVA，hν)h | 0.20 |
| 实施例19(PAA-N75-V15，PAA-L20-IA15，PVA，hν) | 0.27 |
x)UV-吸光度值未校准。
Claims (18)
1.制备UV吸收性接触透镜的方法，所述方法包括以下步骤：
得到眼用透镜，优选接触透镜；
将眼用透镜浸入包含有机溶剂和UV吸收性聚合物的涂覆溶液中足够的时间以在眼用透镜上形成UV吸收涂层，其中UV吸收性聚合物包含：
a)UV吸收性单体单元，
b)共价结合自由基引发结构部分，
c)和至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％含羧基单体单元，以摩尔计；
在浸渍步骤以后任选但优选在亲水性乙烯单体或交联剂的存在下照射眼用透镜以获得UV吸收性聚合物在眼用透镜上的光引发接枝。
2.根据权利要求1的方法，其中各个UV吸收性单体单元包含苯并三唑或二苯甲酮结构部分或其组合。
3.根据权利要求1或2的方法，其中UV吸收性聚合物由通过使包含至少一种含羧基乙烯单体和至少一种UV吸收性乙烯单体的可聚合混合物在乙烯单体的存在或不存在下共聚而得到的中间UV吸收性聚合物得到，条件是含羧基乙烯单体以至少约50％，优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％的量存在于可聚合组合物中，以摩尔计。
4.根据权利要求3的方法，其中UV吸收性乙烯单体选自2-(2-羟基-5-乙烯基苯基)-2H-苯并三唑、2-(2-羟基-5-丙烯酰氧基苯基)-2H-苯并三唑、2-(2-羟基-3-甲基丙烯酰氨基甲基-5-叔辛基苯基)苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氨基苯基)-5-氯苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氨基苯基)-5-甲氧基苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氧基丙基-3'-叔丁基-苯基)-5-氯苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氧基乙基苯基)苯并三唑、2-(2'-羟基-5'-甲基丙烯酰氧基丙基苯基)苯并三唑、2-羟基-4-丙烯酰氧基烷氧基二苯甲酮、2-羟基-4-甲基丙烯酰氧基烷氧基二苯甲酮、烯丙基-2-羟基二苯甲酮和2-羟基-4-甲基丙烯酰氧基二苯甲酮及其组合；其中含羧基乙烯单体选自丙烯酸、C1-C12烷基丙烯酸、N,N-2-丙烯酰氨基羟基乙酸、β-甲基-丙烯酸(巴豆酸)、α-苯基丙烯酸、β-丙烯酰氧基丙酸、山梨酸、当归酸、肉桂酸、1-羧基-4-苯基丁二烯-1,3、衣康酸、柠康酸、中康酸、戊烯二酸、乌头酸、马来酸、富马酸、三羧基乙烯及其组合，优选选自丙烯酸、C1-C6烷基丙烯酸及其组合。
5.根据权利要求1或2的方法，其中UV吸收性聚合物通过使具有至少约50摩尔％(优选至少约60％，更优选至少约70％，甚至更优选至少约80％，最优选至少约90％)含羧基单体单元的前体聚合物在偶联反应中同时或顺序地与UV吸收性化合物和自由基引发化合物反应而得到，
其中UV吸收性化合物由式I、II、III或IV表示：
其中：
R1和R2相互独立地为氢、C1-C12线性或支化烷基、卤素(Cl或Br)、C6-C24芳基、C7-C24烷芳基、C7-C24芳烷基或C1-C12线性或支化烷氧基；
L1和L3相互独立地为共价键或–Xa–E1–Xb–E2–Xc–的二价基团，其中Xa为共价键，–O–，羰基–(RaO)n–的二价基团，其中Ra为线性或支化C1-C12亚烷基且n为1-10，其中R”为H或C1-C8烷基，E1和E2相互独立地为共价键，–(RaO)n–的二价基团，其中Ra和n为以上定义的，其中R”为H或C1-C8烷基、C1-C12线性或支化亚烷基二价基团、具有至多40个碳原子的环烷基二价基团、具有至多40个碳原子的烷基环烷基二价基团、具有至多40个碳原子的烷基芳基二价基团、具有至多40个碳原子的芳基亚烷基二价基团，或者式–C(O)L2C(O)–的二羰基，其中L2为C1-C12线性或支化亚烷基二价基团或者–(Re1–O)w1–(Re2–O)w2–(Re3–O)w3–，其中Re1、Re2和Re3相互独立地为线性或支化C1-C4亚烷基且w1、w2和w3相互独立地为为0-20的值，条件是(n+m+p)的和为1-60，且Xb和Xc相互独立地为共价键、羰基、 其中R”如上文所定义；且
Y和Y1相互独立地为吖内酯基团、环氧基、异氰酸酯基团、吖丙啶基团，或者–NHR的氨基，其中R为氢或者C1-C20未取代或取代、线性或支化烷基，
其中自由基引发化合物具有对羧基呈反应性的官能团。
6.根据权利要求5的方法，其中前体聚合物为：(1)丙烯酸或C1-C12烷基丙烯酸的均聚物；(2)丙烯酸和C1-C12烷基丙烯酸的共聚物；(3)含羧基乙烯单体和含氨基乙烯单体的共聚物，其中含羧基乙烯单体为丙烯酸或C1-C12烷基丙烯酸或其组合，其中含氨基乙烯单体选自(甲基)丙烯酸氨基-C2-C6烷基酯、(甲基)丙烯酸C1-C6烷基氨基-C2-C6烷基酯、烯丙胺、乙烯基胺、氨基-C2-C6烷基(甲基)丙烯酰胺、C1-C6烷基氨基–C2-C6烷基(甲基)丙烯酰胺)及其组合；(4)含羧基乙烯单体和一种或多种亲水乙烯单体的共聚物，其中含羧基乙烯单体为丙烯酸和C1-C12烷基丙烯酸或其组合，其中所述一种或多种亲水乙烯单体不含羧基或氨基且选自丙烯酰胺(AAm)、甲基丙烯酰胺N,N-二甲基丙烯酰胺(DMA)、N,N-二甲基甲基丙烯酰胺(DMMA)、N-乙烯基吡咯烷酮(NVP)、甲基丙烯酸N,N,-二甲基氨基乙酯(DMAEM)、丙烯酸N,N-二甲基氨基乙酯(DMAEA)、N,N-二甲基氨基丙基甲基丙烯酰胺(DMAPMAm)、N,N-二甲基氨基丙基丙烯酰胺(DMAPAAm)、甲基丙烯酸甘油酯、3-丙烯酰氨基-1-丙醇、N-羟乙基丙烯酰胺、N-[三(羟甲基)甲基]-丙烯酰胺、N-甲基-3-亚甲基-2-吡咯烷酮、1-乙基-3-亚甲基-2-吡咯烷酮、1-甲基-5-亚甲基-2-吡咯烷酮、1-乙基-5-亚甲基-2-吡咯烷酮、5-甲基-3-亚甲基-2-吡咯烷酮、5-乙基-3-亚甲基-2-吡咯烷酮、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸羟基丙酯、具有至多1500道尔顿的重均分子量的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯、N-乙烯基甲酰胺、N-乙烯基乙酰胺、N-乙烯基异丙酰胺、N-乙烯基-N-甲基乙酰胺、烯丙醇、乙烯基醇(共聚物中乙酸乙烯酯的水解形式)及其组合。
7.根据权利要求5的方法，其中前体聚合物为聚丙烯酸、聚甲基丙烯酸、聚(C2-C12烷基丙烯酸)、聚(丙烯酸-共聚-甲基丙烯酸)、聚[C2-C12烷基丙烯酸-共聚-(甲基)丙烯酸]、聚(N,N-2-丙烯酰氨基羟基乙酸)、聚[(甲基)丙烯酸-共聚-丙烯酰胺]、聚[(甲基)丙烯酸-共聚-乙烯基吡咯烷酮]、聚[C2-C12烷基丙烯酸-共聚-丙烯酰胺]、聚[C2-C12烷基丙烯酸-共聚-乙烯基吡咯烷酮]、水解聚[(甲基)丙烯酸-共聚-乙酸乙烯酯]、水解聚[C2-C12烷基丙烯酸-共聚-乙酸乙烯酯]或其组合。
8.根据权利要求1-7中任一项的方法，其中有机溶剂以至少约60％，优选至少约70％，更优选至少约80％，甚至更优选至少约90％，最优选至少约95％的量存在于涂覆溶液中，以重量计，其中方法包括以下步骤：将其上具有UV吸收涂层的眼用透镜用水和至多约50％，优选至多约40％，更优选至多约30％，甚至更优选至多约20％，最优选至多约10％有机溶剂的混合物冲洗，以重量计。
9.根据权利要求1-8中任一项的方法，其中共价结合自由基引发结构部分衍生自包含对羧基呈共反应性的基团如氨基或羟基，优选氨基的官能化自由基引发化合物。
10.根据权利要求1-9中任一项的方法，其中自由基引发部分属于噻吨酮类型或苯偶姻类型。
11.根据权利要求1-10中任一项的方法，其中共价结合自由基引发结构部分衍生自Irgacure型光引发剂。
12.根据权利要求1-11中任一项的方法，其中共价结合自由基引发结构部分以约3至约15摩尔％，优选约5至约10摩尔％存在于UV吸收性聚合物中。
13.根据权利要求1-12中任一项的方法，其中UV吸收性单体单元以约4至约15摩尔％，优选约5-12摩尔％存在于UV吸收性聚合物中。
14.根据权利要求1-13中任一项的方法，其中浸渍步骤以后的照射在亲水性乙烯单体或交联剂的存在下进行。
15.根据权利要求1-14中任一项的方法，其中亲水性交联剂为聚(乙二醇)二丙烯酸酯。
16.根据权利要求1-15中任一项的方法，其中UV吸收涂层进一步包含蓝光-吸收聚合物。
17.根据权利要求1-16中任一项的方法，其中眼用透镜为硅氧烷水凝胶接触透镜，其具有通过约90°或更小，优选约80°或更小，更优选约70°或更小，甚至更优选约60°或更小，最优选约50°或更小的平均水接触角表征的表面润湿性。
18.根据权利要求1-17中任一项的方法得到的眼用透镜。
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- 2013-12-16 SG SG11201504763UA patent/SG11201504763UA/en unknown
- 2013-12-16 WO PCT/EP2013/076658 patent/WO2014095690A1/en active Application Filing
- 2013-12-16 HU HUE13814874A patent/HUE031702T2/en unknown
- 2013-12-16 CN CN201380065744.5A patent/CN104871036B/zh active Active
- 2013-12-16 MY MYPI2015001192A patent/MY172901A/en unknown
- 2013-12-16 EP EP13814874.7A patent/EP2932314B1/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| MY172901A (en) | 2019-12-13 |
| US10338408B2 (en) | 2019-07-02 |
| CN104871036B (zh) | 2019-12-10 |
| US20140178595A1 (en) | 2014-06-26 |
| EP2932314B1 (en) | 2017-02-01 |
| EP2932314A1 (en) | 2015-10-21 |
| WO2014095690A1 (en) | 2014-06-26 |
| HUE031702T2 (en) | 2017-07-28 |
| SG11201504763UA (en) | 2015-07-30 |
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