CN103917899A - 通过涂布制备uv吸收性眼用透镜的方法 - Google Patents
通过涂布制备uv吸收性眼用透镜的方法 Download PDFInfo
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- CN103917899A CN103917899A CN201280050162.5A CN201280050162A CN103917899A CN 103917899 A CN103917899 A CN 103917899A CN 201280050162 A CN201280050162 A CN 201280050162A CN 103917899 A CN103917899 A CN 103917899A
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- Prior art keywords
- methyl
- acid
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- approximately
- alkyl
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- 238000000576 coating method Methods 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 60
- 239000011248 coating agent Substances 0.000 title claims abstract description 52
- 239000000178 monomer Substances 0.000 claims abstract description 111
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000000463 material Substances 0.000 claims description 76
- -1 octyl phenyl Chemical group 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 239000006096 absorbing agent Substances 0.000 claims description 51
- 239000000017 hydrogel Substances 0.000 claims description 51
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 39
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 38
- 125000000524 functional group Chemical group 0.000 claims description 38
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 35
- 239000004593 Epoxy Substances 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 27
- 150000003573 thiols Chemical class 0.000 claims description 26
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 22
- 239000012744 reinforcing agent Substances 0.000 claims description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229920000768 polyamine Polymers 0.000 claims description 19
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 230000031700 light absorption Effects 0.000 claims description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 15
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- 238000004806 packaging method and process Methods 0.000 claims description 14
- 229920001519 homopolymer Polymers 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004069 aziridinyl group Chemical group 0.000 claims description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
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- 239000002253 acid Substances 0.000 claims description 10
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 9
- 239000012965 benzophenone Substances 0.000 claims description 9
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 9
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- 239000002243 precursor Substances 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 6
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
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- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 5
- AFXKUUDFKHVAGI-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidin-2-one Chemical compound CN1CCC(=C)C1=O AFXKUUDFKHVAGI-UHFFFAOYSA-N 0.000 claims description 4
- ZZDBHIVVDUTWJC-UHFFFAOYSA-N 1-methyl-5-methylidenepyrrolidin-2-one Chemical compound CN1C(=C)CCC1=O ZZDBHIVVDUTWJC-UHFFFAOYSA-N 0.000 claims description 4
- VDORPYPVQAFLTR-UHFFFAOYSA-N 5-methyl-3-methylidenepyrrolidin-2-one Chemical compound CC1CC(=C)C(=O)N1 VDORPYPVQAFLTR-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
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- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000007789 sealing Methods 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
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
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- 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
- 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 compound OC1=CC=C(C=C)C=C1N1N=C2C=CC=CC2=N1 RBUACGOFWUSJNX-UHFFFAOYSA-N 0.000 claims description 2
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-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
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
- YOCBKMGIFSUGDK-UHFFFAOYSA-N N-[3-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=C(O)C(N2N=C3C=C(Cl)C=CC3=N2)=C1 YOCBKMGIFSUGDK-UHFFFAOYSA-N 0.000 claims description 2
- 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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 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
- RLYNGYDVXRKEOO-SQQVDAMQSA-N but-2-enoic acid;(e)-but-2-enoic acid Chemical compound CC=CC(O)=O.C\C=C\C(O)=O RLYNGYDVXRKEOO-SQQVDAMQSA-N 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
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- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 2
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- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 2
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 12
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- 125000003118 aryl group Chemical group 0.000 description 7
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Abstract
本文描述了用于制备UV吸收性接触透镜的具有成本效率和时间效率的方法。与涉及使包含UV吸收性乙烯属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，本发明方法涉及将接触透镜浸入包含含羧基单体单元和UV吸收性单体单元的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全部通过所谓的铸造模塑方法制备，所述方法涉及使包含可聚合UV吸收剂和至少一种乙烯属单体、大分子单体和/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吸收剂通过萃取方法除去以确保所得眼用透镜具有对用途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萃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吸收性接触透镜的成本有效方法。
概述
一方面，本发明提供制备UV吸收性眼用透镜的方法，所述方法包括步骤：得到眼用透镜，优选接触透镜；将眼用透镜浸入包含第一有机溶剂和UV吸收性聚合物的涂料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，和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元；和任选，但优选使具有反应性官能团的亲水聚合物或聚合材料共价附着在UV吸收涂层上以形成水凝胶涂层，其中水凝胶涂层通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着在UV吸收涂层上。
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；和共价附着在UV吸收性聚合物层上的水凝胶涂层，其中UV吸收性聚合物包含UV吸收性单体单元和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元，其中水凝胶涂层通过使具有反应性官能团的亲水聚合物或聚合材料通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着在UV吸收性聚合物层上而得到。
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获知。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显示通过浸入荧光素改性的PAA溶液中不同的时间而得到的其上具有涂层的硅水凝胶接触透镜的UV-Vis透射光谱。A：5秒；B：60秒；C：10分钟；D：1小时；E：5小时；F：24小时。
图2显示作为用于得到涂层的浸渍时间的函数，其上具有涂层的硅水凝胶接触透镜在490nm下的UV-Vis吸光度。
图3显示其上具有UV吸收涂层的硅水凝胶接触透镜的UV-Vis透射光谱。
图4显示其上具有不同涂层的硅水凝胶接触透镜的UV-Vis透射光谱。1：具有PAA-L20涂层(浸入PAA-L20溶液中约20分钟)；具有PAA-N20和PAA-L20涂层(浸入PAA-N20溶液中，然后浸入PAA-L20溶液中分别约20分钟)。
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，单数形式的不定冠词(a/an)和定冠词(the)包括复数对象。因此，例如提及不定冠词修饰的“单体”包括两种或更多种这类单体的混合物，等。
“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。“硅水凝胶接触透镜”指包含硅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合时聚合物基体内可含有至少10重量%水的交联聚合材料。
关于溶剂中的化合物或材料，术语“可溶性”意指化合物或材料在室温下(即在约20至约30℃的温度下)可溶于溶剂中以得到浓度为至少0.5重量%的溶液。
关于溶剂中的化合物或材料，术语“不可溶（不溶性）”意指化合物或材料在室温下可溶于溶剂中以得到浓度小于0.005重量%的溶液。
“硅水凝胶”指含有硅氧烷的水凝胶。硅水凝胶通常通过包含至少一种含硅氧烷乙烯属单体或至少一种含硅氧烷乙烯属大分子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而得到。
“乙烯属单体”指可溶于溶剂中且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。典型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“亲水乙烯属单体”指可聚合形成水溶性或可吸收至少10重量%水的均聚物的乙烯属单体。
“疏水性乙烯属单体”指可聚合形成不溶于水并可吸收小于10重量%水的均聚物的乙烯属单体。
如本申请中所用，术语“大分子单体”或“预聚物”指可溶于溶剂中且含有两个或更多个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分子单体或预聚物聚合/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(包括单体材料或大分子单体材料)的“分子量”指重均分子量。
除非另外明确指出，如本申请中所用，术语“氨基”指式–NHR’的伯或仲氨基，其中R’为氢或C1-C20未被取代或经取代的线性或支化烷基。
如本申请中所用，术语“表氯醇官能化聚胺”或“表氯醇官能化聚酰胺胺”指通过使聚胺或聚酰胺胺与表氯醇反应以将聚胺或聚酰胺胺的所有或实质百分数的胺基团转化成氮杂环丁基团而得到的聚合物。
术语“氮杂环丁基团”指的正电性基团。
如本申请中所用，术语“磷酸胆碱”指的两性离子基团，其中n为1-5的整数，且R1、R2和R3各自独立地为或C1-C8烷基或C1-C8羟基烷基。
如本申请中所用，术语“水接触角”指平均水接触角(即通过固滴法(Sessile Drop method)测定的接触角)，其通过接触角的测量值平均而得到。
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合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而形成。
“聚合物”意指通过使一种或多种单体交联或聚合而形成的材料。
本发明一般性地涉及制备UV吸收性眼用透镜，特别是接触透镜的具有成本效率和时间效率的方法。与涉及使包含UV吸收性乙烯属单体的透镜形成组合物共聚合的UV吸收性眼用透镜传统制备方法相反，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模塑的眼用透镜上。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料溶液时，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。
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吸收性乙烯属单体的缺点。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节中进行。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。
一方面，本发明提供制备UV吸收性眼用透镜的方法，所述方法包括步骤：得到眼用透镜，优选接触透镜；将眼用透镜浸入包含第一有机溶剂和UV吸收性聚合物的涂料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，和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元；和任选，但优选使具有反应性官能团的亲水聚合物或聚合材料共价附着在UV吸收涂层上以形成水凝胶涂层，其中水凝胶涂层通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着在UV吸收涂层上。
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Nos.4,347,198；5,508,317；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水凝胶纽扣形物车床切割而生产。在铸造模塑中，通常将透镜配制剂分散于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：含硅氧烷乙烯属单体、含硅氧烷乙烯属大分子单体、亲水乙烯属单体、亲水性乙烯属大分子单体、疏水性乙烯属单体及其组合。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可以使所得硅水凝胶接触透镜经受用萃取溶剂萃取以从所得透镜中除去未聚合的组分并经受水合方法。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。大量非硅水凝胶透镜配制剂和硅水凝胶透镜配制剂描述于本申请的提交日期之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。用于制备商业硅水凝胶接触透镜的硅水凝胶透镜配制剂，例如lotrafilcon A、lotrafilcon B、balafilcon A、galyfilcon A、senofilcon A、narafilcon A、narafilcon B、comfilcon A、enfilcon A、asmofilcon A、filcon II3也可用于制备硅水凝胶接触透镜，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。
生产用于铸造模塑接触透镜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钉板条形成。形成模具的合适方法的实例公开于美国专利Nos.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吸收性单体单元和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%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，其在聚合中衍生自乙烯属单体，并可在聚合以后任选通过化合物改性。
本发明UV吸收性聚合物可通过使包含至少一种含羧基乙烯属单体和至少一种UV吸收性乙烯属单体的可聚合混合物在乙烯属单体的存在或不存在下共聚而得到，条件是含羧基乙烯属单体以至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%的量存在于可聚合组合物中。
任何UV吸收性乙烯属单体可用于制备本发明UV吸收性聚合物。优选UV吸收性乙烯属单体的实例包括但不限于含苯并三唑乙烯属单体(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Nos.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Nos3,162,676(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。
任何合适的含羧基乙烯属单体可用于制备本发明UV吸收性聚合物。优选含羧基乙烯属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。优选UV吸收性聚合物由至少一种选自丙烯酸、C1-C6烷基丙烯酸及其组合的含羧基乙烯属单体制备。
作为选择，本发明UV吸收性聚合物可通过使UV吸收性化合物与(即使UV吸收性结构部分共价附着在)具有至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%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同反应性官能团之间的偶联反应的非限定性实例予以说明：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、二氢唑酮基团(azlactone group)、异氰酸酯基团、环氧基、氮杂环丙烷基团(aziridine group)、硫羟基和酰胺基团(─CONH2)。羧酸基团与氨基-NHR’在偶联剂—碳二亚胺(例如1-乙基-3-(3-二甲基氨基丙基)碳二亚胺(EDC)、N,N’-二环己基碳二亚胺(DCC)、1-环己基-3-(2-吗啉基乙基)碳二亚胺、二异丙基碳二亚胺或其混合物)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；羧基与环氧基或氮杂环丙烷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(-CO-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’与环氧基或氮杂环丙烷基团反应以形成胺碱(C-NR’)；氨基与二氢唑酮基团反应(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；羟基与环氧基或氮杂环丙烷反应以形成醚键(-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；羟基与二氢唑酮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-)；硫羟基(-SH)与异氰酸酯反应以形成硫代氨基甲酸酯键(-N-C(O)-S-)；硫羟基与环氧基或氮杂环丙烷反应以形成硫醚键(-S-)；硫羟基与酰基氯或酰基溴基团或与酸酐基团反应以形成硫羟酸酯键；硫羟基与二氢唑酮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-)；硫羟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–)；硫羟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、双二氢唑酮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、两个氮杂环丙烷、两个羧基、两个酰基卤或两个二氢唑酮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。
任何包含至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元的聚合物可作为前体聚合物用于UV吸收性聚合物制备中。优选前体聚合物为：含羧基乙烯属单体(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；含羧基乙烯属单体(丙烯酸或C1-C12烷基丙烯酸)和含氨基乙烯属单体(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；含羧基乙烯属单体(丙烯酸或C1-C12烷基丙烯酸)和一种或多种亲水乙烯属单体的共聚物，所述亲水乙烯属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-co-甲基丙烯酸)、聚[C2-C12烷基丙烯酸-co-(甲基)丙烯酸]、聚(N,N-2-丙烯酰氨基羟基乙酸)、聚[(甲基)丙烯酸-co-丙烯酰胺]、聚[(甲基)丙烯酸-co-乙烯基吡咯烷酮]、聚[C2-C12烷基丙烯酸-co-丙烯酰胺]、聚[C2-C12烷基丙烯酸-co-乙烯基吡咯烷酮]、水解聚[(甲基)丙烯酸-co-乙酸乙烯酯]、水解聚[C2-C12烷基丙烯酸-co-乙酸乙烯酯]或其组合。
包含UV吸收性结构部分和选自氨基、二氢唑酮基团、环氧基、异氰酸酯基团、氮杂环丙烷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，或其中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， 或其中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个碳原子的烷芳基二价基团、具有至多40个碳原子的亚芳烷基二价基团，或者具有式–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–(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0-20的数，条件是(w1+w2+w3)的和为1-60，且Xb和Xc相互独立地为共价键、羰基、 其中R”为以上定义的；且
Y为二氢唑酮基团、环氧基、异氰酸酯基团、氮杂环丙烷基团或–NHR’的氨基，其中R’为氢或C1-C12未被取代或经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(thiol-ene)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)反应而由含苯并三唑乙烯基单体(上述那些中的任一种)制备。
其中Y为二氢唑酮基团、环氧基或异氰酸酯基团的式I、II或III的UV吸收性化合物可通过使具有一个羟基烷氧基或氨基的苯并三唑化合物与过量摩尔当量量的双二氢唑酮化合物、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由具有一个羟基烷氧基或氨基的苯并三唑化合物制备。
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、二甘醇二缩水甘油醚、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双二氢唑酮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未被取代或经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，或其中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， 或其中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个碳原子的烷芳基二价基团，具有至多40个碳原子的亚芳烷基二价基团，具有式–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–(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0-20的数，条件是(w1+w2+w3)的和为1-60，且Xb和Xc相互独立地为共价键、羰基、 其中R”是上文定义的；且
Y1为二氢唑酮基团、环氧基、异氰酸酯基团、氮杂环丙烷基团，或–NHR的氨基，其中R为氢或C1-C12未被取代或经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未被取代或经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-烯反应使含二苯甲酮的乙烯基单体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的乙烯基单体制备。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双二氢唑酮化合物、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为二氢唑酮基团、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的化合物，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未被取代或经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为共价键或或其中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、 其中R”是上文定义的；且Y为–NHR的氨基，其中R为氢或C1-C6未被取代或经取代的线性或支化烷基。
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)、二甘醇正丁基醚、二甘醇甲基醚、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、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、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萃取溶剂萃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，萃取步骤可在将UV吸收性聚合物的涂层(层)应用于接触透镜上之后进行。
在优选实施方案中，第一有机溶剂以至少约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重量%的量存在于涂料溶液中，且本发明方法进一步包括步骤：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重量%第二有机溶剂(其可与第一有机溶剂相同或不同)的混合物冲洗。
在另一优选实施方案中，本发明方法包括步骤：使具有反应性官能团的亲水聚合物或聚合材料共价附着在UV吸收涂层上以形成水凝胶涂层，其中水凝胶涂层通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着在UV吸收涂层上。包含反应性官能团的任何亲水聚合物和任何亲水性聚合材料可用于本发明中，条件是亲水聚合物或亲水性聚合材料可溶于任何溶剂或溶剂体系，优选水中。反应性官能团的实例包括但不限于氮杂环丁基团(azetidiniumgroup)、环氧基、异氰酸酯基团、氮杂环丙烷基团、二氢唑酮基团、氨基、羧基及其组合。优选用于形成水凝胶涂层的水溶性且可交联亲水性聚合材料为包含三维网络和在网络内的反应性官能团的部分交联聚合材料，所述反应性官能团选自氮杂环丁基团、环氧基、异氰酸酯基团、氮杂环丙烷基团、二氢唑酮基团、氨基、羧基及其组合，其中氮杂环丁基团是最优选的实施方案。关于聚合材料的术语“部分交联”意指用于在交联反应中制备聚合材料的原料的反应性(可交联)官能团未完全消耗。在优选实施方案中，用于形成水凝胶涂层的亲水聚合物或亲水性聚合材料包含UV吸收性结构部分。UV吸收性结构部分可通过将以上式(I)、(II)、(III)或(IV)的UV吸收性化合物偶联在亲水聚合物或亲水性聚合材料(如上所述)上而引入，条件是不是亲水聚合物或聚合材料的所有反应性官能团都被消耗。通过UV吸收涂层上具有水凝胶涂层，疏水性UV吸收性结构部分可没入水凝胶表面以下且不会影响接触透镜的亲水性和可湿性。
包含选自氮杂环丁基团、环氧基、异氰酸酯基团、氮杂环丙烷基团、二氢唑酮基团、氨基、羧基及其组合的反应性官能团的任何亲水聚合物可用于根据本领域技术人员已知的任何偶联反应形成水凝胶涂层(多个水凝胶涂层)。优选含有反应性官能团的单体单元的摩尔百分数为约40%或更少，优选约35%或更少，更优选约30%或更少，甚至更优选约25%或更少，最优选约20%或更少。通过使用具有相对小摩尔百分数的各自具有反应性官能团的单体单元的亲水聚合物，水凝胶(交联的)涂层可具有相对低交联密度以及因此低柔软度(弹性模量)和舒适润滑性。用于在接触透镜上形成水凝胶涂层的优选亲水聚合物的实例包括但不限于包含至少约60摩尔%至少一种非反应性乙烯属单体和至多约40摩尔%至少一种反应性乙烯属单体的共聚物，其中反应性乙烯属单体选自含羧基乙烯属单体、含氨基乙烯属单体、含环氧基乙烯属单体、含氮杂环丙烷乙烯属单体、含二氢唑酮乙烯属单体、含异氰酸酯乙烯属单体、其组合，其中非反应性亲水乙烯属单体选自丙烯酰胺(AAm)、N,N-二甲基丙烯酰胺(DMA)、N-乙烯基吡咯烷酮(NVP)、N-乙烯基-N-甲基乙酰胺、(甲基)丙烯酸甘油酯、(甲基)丙烯酸羟基乙基酯、N-羟基乙基(甲基)丙烯酰胺、重均分子量为至多400道尔顿的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯、乙烯醇、N-甲基-3-亚甲基-2-吡咯烷酮、1-甲基-5-亚甲基-2-吡咯烷酮、5-甲基-3-亚甲基-2-吡咯烷酮、(甲基)丙烯酸N,N-二甲基氨基乙酯、N,N-二甲基氨基丙基(甲基)丙烯酰胺、(甲基)丙烯酰氧基乙基磷酸胆碱及其组合。
含氨基乙烯属单体的实例包括但不限于(甲基)丙烯酸氨基-C1-C6烷基酯、(甲基)丙烯酸C1-C6烷基氨基-C1-C6烷基酯、烯丙胺、乙烯胺、氨基-C1-C6烷基(甲基)丙烯酰胺、C1-C6烷基氨基-C1-C6烷基(甲基)丙烯酰胺、二-氨基-C1-C6烷基(甲基)丙烯酰胺、二-C1-C6烷基氨基-C1-C6烷基(甲基)丙烯酰胺或其组合。
含二氢唑酮乙烯属单体的实例包括但不限于2-乙烯基-4,4-二甲基-1,3-唑啉-5-酮、2-异丙烯基-4,4-二甲基-1,3-唑啉-5-酮、2-乙烯基-4-甲基-4-乙基-1,3-唑啉-5-酮、2-异丙烯基-4-甲基-4-丁基-1,3-唑啉-5-酮、2-乙烯基-4,4-二丁基-1,3-唑啉-5-酮、2-异丙烯基-4-甲基-4-十二烷基-1,3-唑啉-5-酮、2-异丙烯基-4,4-二苯基-1,3-唑啉-5-酮、2-异丙烯基-4,4-五亚甲基-1,3-唑啉-5-酮、2-异丙烯基-4,4-四亚甲基-1,3-唑啉-5-酮、2-乙烯基-4,4-二乙基-1,3-唑啉-5-酮、2-乙烯基-4-甲基-4-壬基-1,3-唑啉-5-酮、2-异丙烯基-4-甲基-4-苯基-1,3-唑啉-5-酮、2-异丙烯基-4-甲基-4-苄基-1,3-唑啉-5-酮、2-乙烯基-4,4-五亚甲基-1,3-唑啉-5-酮和2-乙烯基-4,4-二甲基-1,3-唑啉-6-酮，其中2-乙烯基-4,4-二甲基-1,3-唑啉-5-酮(VDMO)和2-异丙烯基-4,4-二甲基-1,3-唑啉-5-酮(IPDMO)是优选的含二氢唑酮乙烯属单体。
含烷氧基乙烯属单体的实例包括但不限于(甲基)丙烯酸缩水甘油酯、烯丙基缩水甘油醚、甲基烯丙基缩水甘油醚、缩水甘油基(甲基)丙烯酰胺、(甲基)丙烯酸C1-C6羟基烷基酯缩水甘油醚(例如(甲基)丙烯酸4-羟基丙基酯缩水甘油醚、(甲基)丙烯酸羟基丙基酯缩水甘油醚、(甲基)丙烯酸羟基乙酯缩水甘油醚)、缩水甘油基(甲基)丙烯酰胺、二缩水甘油基(甲基)丙烯酰胺、乙基丙烯酸缩水甘油酯、衣康酸缩水甘油酯、(甲基)丙烯酸甲基缩水甘油酯、3,4-环氧基-1-乙烯基环己烷，和US5,677,398(通过引用将其全部并入本文中)所述那些。
含异氰酸酯乙烯属单体的实例包括但不限于(甲基)丙烯酸异氰酸酯基-C1-C6烷基酯。
含氮杂环丙烷乙烯属单体的实例包括但不限于(甲基)丙烯酸吖丙啶基C1-C12烷基酯(例如(甲基)丙烯酸2-(1-吖丙啶基)乙酯、(甲基)丙烯酸3-(1-吖丙啶基)丙酯、(甲基)丙烯酸4-(1-吖丙啶基)丁酯、(甲基)丙烯酸6-(1-吖丙啶基)己酯或(甲基)丙烯酸8-(1-吖丙啶基)辛酯)，和US3,974,131(通过引用将其全部并入本文中)所述那些吖丙啶基乙烯基单体(例如二甘醇单-(甲基)丙烯酸酯单-2-吖丙啶基丙酸酯)。
在优选实施方案中，用于形成水凝胶涂层(或交联涂层)的水溶性且可交联亲水性聚合材料包含(i)约20至约95重量%的衍生自表氯醇官能化聚胺或聚酰胺胺的第一聚合物链，(ii)约5至约80重量%的衍生自至少一种亲水性增强剂的亲水性结构部分或第二聚合物链，所述亲水性增强剂具有至少一个选自氨基、羧基、硫羟基及其组合的反应性官能团，其中亲水性结构部分或第二聚合物链通过各自在表氯醇官能化聚胺或聚酰胺胺的一个氮杂环丁基团与亲水性增强剂的一个氨基、羧基或硫羟基之间形成的一个或多个共价键共价连接在第一聚合物链上，和(iii)氮杂环丁基团，其为第一聚合物链的一部分或者共价连接在第一聚合物链上的侧基或端基。优选第一和第二聚合物链的至少一个包含UV吸收性单体单元。
用这类水溶性且可交联亲水性聚合材料，水凝胶涂层(或交联涂层)的形成可通过将其上具有UV吸收涂层的接触透镜在水溶液中在亲水性聚合材料的存在下简单地加热至且在约40至约140℃的温度下足够的时间以使亲水性聚合材料通过各自在亲水性聚合材料的一个氮杂环丁基团与接触透镜上UV吸收涂层的一个羧基之间形成的共价键共价连接在接触透镜表面上，由此在接触透镜上形成交联亲水涂层。应当理解任何含有反应性官能团的水溶性且可交联亲水性聚合材料(例如上述那些)可在本发明中用于形成接触透镜的水凝胶涂层。
含有氮杂环丁基团的水溶性且可热交联亲水性聚合材料包含(即它具有包含如下的组成)约20至约95重量%，优选约35至约90重量%，更优选约50至约85重量%的衍生自表氯醇官能化聚胺或聚酰胺胺的第一聚合物链，和约5至约80重量%，优选约10至约65重量%，甚至更优选约15至约50重量%的衍生自至少一种亲水性增强剂的亲水性结构部分或第二聚合物链，所述亲水性增强剂具有至少一个选自氨基、羧基、硫羟基及其组合的反应性官能团。亲水性聚合材料的组成由用于根据以上示意图I所示交联反应而制备可热交联亲水性聚合材料的反应物混合物的组成(基于反应物的总重量)决定。例如，如果反应物混合物包含基于反应物的总重量约75重量%表氯醇官能化聚胺或聚酰胺胺和约25重量%至少一种亲水性增强剂，则反应物亲水性聚合材料包含约75重量%的衍生自表氯醇官能化聚胺或聚酰胺胺的第一聚合物链和约25重量%的衍生自所述至少一种亲水性增强剂的亲水性结构部分或第二聚合物链。可热交联亲水性聚合材料的氮杂环丁基团为不参与用于制备可热交联亲水性聚合材料的交联反应的那些(表氯醇官能化聚胺或聚酰胺胺的)氮杂环丁基团。
表氯醇官能化聚胺或聚酰胺胺可通过使表氯醇与聚胺聚合物或含有伯或仲氨基的聚合物反应而得到。例如，聚(亚烷基亚胺)或聚(酰胺胺)，其为衍生自聚胺和二羧酸的缩聚物(例如己二酸-二亚乙基三胺共聚物)，可与表氯醇反应以形成表氯醇官能化聚合物。类似地，(甲基)丙烯酸氨基烷基酯、(甲基)丙烯酸单-烷基氨基烷基酯、氨基烷基(甲基)丙烯酰胺或单-烷基氨基烷基(甲基)丙烯酰胺的均聚物或共聚物也可与表氯醇反应以形成表氯醇官能化聚胺。聚胺或聚酰胺胺聚合物的表氯醇官能化的反应条件教导于EP1465931(通过引用将其全部内容并入本文中)中。优选的表氯醇官能化聚合物为聚氨基酰胺-表氯醇(PAE)(或聚酰胺-聚胺-表氯醇或聚酰胺-表氯醇)，例如来自Hercules的树脂(表氯醇官能化己二酸-二亚乙基三胺共聚物)或来自Servo/Delden的树脂。
任何合适的亲水性增强剂可用于本发明中，条件是它们含有至少一个氨基、至少一个羧基和/或至少一个硫羟基。
一类优选的亲水性增强剂包括但不限于：含有氨基、羧基或硫醇的单糖(例如3-氨基-1,2-丙二醇、1-硫羟基甘油、5-酮-D-葡糖酸、半乳糖胺、葡糖胺、半乳糖醛酸、葡糖酸、氨基葡糖酸、甘露糖胺、葡糖二酸1,4-内酯、糖酸、尤罗索尼克酸(Ketodeoxynonulosonic acid)、N-甲基-D-葡糖胺、1-氨基-1-脱氧-β-D-半乳糖、1-氨基-1-脱氧山梨糖醇、1-甲基氨基-1-脱氧山梨糖醇、N-氨基乙基葡糖酰胺)；含有氨基、羧基或硫羟基的二糖(例如软骨素二糖钠盐、二(β-D-吡喃糖木基)胺、二半乳糖醛酸、肝素二糖、透明质酸二糖、乳糖酸)；和含有氨基、羧基或硫羟基的低聚糖(例如羧甲基-β-环糊精钠盐、三半乳糖醛酸)；及其组合。
另一类优选的亲水性增强剂为具有一个或多个氨基、羧基和/或硫羟基的亲水聚合物。更优选，作为亲水性增强剂的亲水聚合物中具有氨基(–NHR’，其中R’如上文所定义)、羧基(–COOH)和/或硫羟基(–SH)的单体单元的含量基于亲水聚合物的总重量为小于约40重量%，优选小于约30重量%，更优选小于约20重量%，甚至更优选小于约10重量%。
作为亲水性增强剂的一类优选亲水聚合物为含氨基或含羧基多糖，例如羧甲基纤维素(具有约40%或更少的羧基含量，其基于重复单元─[C6H10-mO5(CH2CO2H)m]─的组成估算，其中m为1-3)、羧乙基纤维素(具有约36%或更少的羧基含量，其基于重复单元─[C6H10-mO5(C2H4CO2H)m]─的组成估算，其中m为1-3)、羧丙基纤维素(具有约32%或更少的羧基含量，其基于重复单元─[C6H10-mO5(C3H6CO2H)m]─的组成估算，其中m为1-3)、透明质酸(具有约11%的羧基含量，其基于重复单元─(C13H20O9NCO2H)─的组成估算)、硫酸软骨素(具有约9.8%的羧基含量，其基于重复单元─(C12H18O13NS CO2H)─的组成估算)，或其组合。
作为亲水性增强剂的另一类优选亲水聚合物包括但不限于：具有单氨基、羧基或硫羟基的聚(乙二醇)(PEG)(例如PEG-NH2、PEG-SH、PEG-COOH)；H2N-PEG-NH2；HOOC-PEG-COOH；HS-PEG-SH；H2N-PEG-COOH；HOOC-PEG-SH；H2N-PEG-SH；具有一个或多个氨基、羧基或硫羟基的多臂PEG；具有一个或多个氨基、羧基或硫羟基的PEG树状聚合物；非反应性亲水乙烯属单体的二氨基-或二羧基封端均聚物或共聚物；非反应性亲水乙烯属单体的单氨基-或单羧基封端均聚物或共聚物；为包含如下组分的组合物的聚合产物的共聚物：(1)约60重量%或更少，优选约0.1至约30重量%，更优选约0.5至约20重量%，甚至更优选约1至约15重量%一种或多种反应性乙烯属单体，和(2)至少一种非反应性亲水乙烯属单体和/或至少一种含磷酸胆碱乙烯属单体；及其组合。反应性乙烯属单体和非反应性亲水乙烯属单体为前文所述那些。
更优选，作为亲水性增强剂的亲水聚合物为PEG-NH2；PEG-SH；PEG-COOH；H2N-PEG-NH2；HOOC-PEG-COOH；HS-PEG-SH；H2N-PEG-COOH；HOOC-PEG-SH；H2N-PEG-SH；具有一个或多个氨基、羧基或硫羟基的多臂PEG；具有一个或多个氨基、羧基或硫羟基的PEG树状聚合物；非反应性亲水乙烯属单体的单氨基-、单羧基-、二氨基-或二羧基封端均聚物或共聚物，所述非反应性亲水乙烯属单体选自丙烯酰胺(AAm)、N,N-二甲基丙烯酰胺(DMA)、N-乙烯基吡咯烷酮(NVP)、N-乙烯基-N-甲基乙酰胺、(甲基)丙烯酸甘油酯、(甲基)丙烯酸羟基乙酯、N-羟乙基(甲基)丙烯酰胺、重均分子量为至多400道尔顿的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯、乙烯醇、N-甲基-3-亚甲基-2-吡咯烷酮、1-甲基-5-亚甲基-2-吡咯烷酮、5-甲基-3-亚甲基-2-吡咯烷酮、(甲基)丙烯酸N,N-二甲基氨基乙酯、N,N-二甲基氨基丙基(甲基)丙烯酰胺、(甲基)丙烯酰氧基乙基磷酸胆碱及其组合；为包含如下组分的组合物的聚合产物的共聚物：(1)约0.1至约30重量%，优选约0.5至约20重量%，更优选约1至约15重量%(甲基)丙烯酸、C2-C12烷基丙烯酸、乙烯胺、烯丙胺和/或(甲基)丙烯酸氨基-C2-C4烷基酯，(2)(甲基)丙烯酰氧基乙基磷酸胆碱和/或至少一种选自如下的非反应性亲水乙烯属单体：丙烯酰胺、N,N-二甲基丙烯酰胺、N-乙烯基吡咯烷酮、N-乙烯基-N-甲基乙酰胺、(甲基)丙烯酸甘油酯、(甲基)丙烯酸羟基乙酯、N-羟乙基(甲基)丙烯酰胺、重均分子量为至多400道尔顿的C1-C4烷氧基聚乙二醇(甲基)丙烯酸酯、乙烯醇及其组合。
最优选，作为亲水性增强剂的亲水性增强剂为PEG-NH2；PEG-SH；PEG-COOH；单氨基-、单羧基-、二氨基-或二羧基封端聚乙烯基吡咯烷酮；单氨基-、单羧基-、二氨基-或二羧基封端聚丙烯酰胺；单氨基-、单羧基-、二氨基-或二羧基封端聚(DMA)；单氨基-或单羧基-、二氨基-或二羧基封端聚(DMA-co-NVP)；单氨基-、单羧基-、二氨基-或二羧基封端聚(NVP-co-(甲基)丙烯酸N,N-二甲基氨基乙酯))；单氨基-、单羧基-、二氨基-或二羧基封端聚(乙烯醇)；单氨基-、单羧基-、二氨基-或二羧基封端聚[(甲基)丙烯酰氧基乙基磷酸胆碱]均聚物或共聚物；单氨基-、单羧基-、二氨基-或二羧基封端聚(NVP-co-乙烯醇)；单氨基-、单羧基-、二氨基-或二羧基封端聚(DMA-co-乙烯醇)；具有约0.1至约30重量%，优选约0.5至约20重量%，更优选约1至约15重量%(甲基)丙烯酸的聚[(甲基)丙烯酸-co-丙烯酰胺]；具有约0.1至约30重量%，优选约0.5至约20重量%，更优选约1至约15重量%(甲基)丙烯酸的聚[(甲基)丙烯酸-co-NVP)；为包含如下组分的组合物的聚合产物的共聚物：(1)(甲基)丙烯酰氧基乙基磷酸胆碱和(2)约0.1至约30重量%，优选约0.5至约20重量%，更优选约1至约15重量%含羧酸乙烯属单体和/或含氨基乙烯属单体，及其组合。
具有官能团的PEG和具有官能团的多臂PEG可由多个商业供应商如Polyscience和Shearwater Polymers，Inc.等得到。
一种或多种非反应性亲水乙烯属单体或含磷酸胆碱乙烯属单体的单氨基-、单羧基-、二氨基-或二羧基封端的均聚物或共聚物可根据美国专利No.6,218,508所述程序制备，通过引用将其全部内容并入本文中。例如，为制备非反应性亲水乙烯属单体的二氨基或二羧基封端均聚物或共聚物，使非反应性乙烯属单体、具有氨基或羧基的链转移剂(例如2-氨基乙硫醇、2-巯基丙酸、巯基乙酸、硫羟乳酸或其它羟基硫醇、氨基硫醇或含羧基硫醇)和任选其它乙烯属单体与反应性乙烯属单体(具有氨基或羧基)在自由基引发剂的存在下共聚(热或光化)。通常，链转移剂与不同于反应性乙烯属单体的所有乙烯属单体的摩尔比为约1:5至约1:100，而链转移剂与反应性乙烯属单体的摩尔比为1:1。在该制备中，具有氨基或羧基的链转移剂用于控制所得亲水聚合物的分子量并形成所得亲水聚合物的末端，以提供给所得亲水聚合物一个末端氨基或羧基，同时反应性乙烯属单体提供给所得亲水聚合物另一末端羧基或氨基。类似地，为制备非反应性亲水乙烯属单体的单氨基-或单羧基封端均聚物或共聚物，使非反应性乙烯属单体、具有氨基或羧基的链转移剂(例如2-氨基乙硫醇、2-巯基丙酸、巯基乙酸、硫羟乳酸或其它羟基硫醇、氨基硫醇或含羧基硫醇)和任选其它乙烯属单体在不存在任何反应性乙烯属单体下共聚(热或光化)。
包含非反应性亲水乙烯属单体和反应性乙烯属单体(例如含羧基乙烯属单体)的共聚物可根据任何熟知的自由基聚合方法制备或者由商业供应商得到。含有甲基丙烯酰氧基乙基磷酸胆碱和含羧基乙烯属单体的共聚物可由NOP Corporation得到(例如-A和–AF)。
具有至少一个氨基、羧基或硫羟基(作为亲水性增强剂)的亲水聚合物的重均分子量Mw优选为约500至约1,000,000，更优选约1,000至约500,000。
根据本发明，亲水性增强剂与表氯醇官能化聚胺或聚酰胺胺之间的反应在约40至约100℃的温度下进行足够的时间(约0.3至约24小时，优选约1至约12小时，甚至更优选约2至约8小时)以形成含有氮杂环丁基团的水溶性且可热交联亲水性聚合材料。
根据本发明，必须选择亲水性增强剂相对于表氯醇官能化聚胺或聚酰胺胺的浓度以不使所得亲水性聚合材料不溶于水(即在室温下小于0.005g每100ml水的溶解度)且不消耗表氯醇官能化聚胺或聚酰胺胺的多于约99%，优选约98%，更优选约97%，甚至更优选约96%氧杂环丁基团。
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，包装溶液为在压热处理以后眼用安全的缓冲水溶液。作为选择，优选通过将包含UV吸收涂层和在底涂层上的水溶性可热交联亲水性聚合材料层，在密封透镜包装中浸入包装溶液(即缓冲水溶液)中的接触透镜在约118至约125℃的温度下压热处理约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收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以提供约200至约450毫渗透分子(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)。
生理相容性缓冲剂的实例为硼酸、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)、双-三(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，包装溶液优选包含约0.01至约2重量%，更优选约0.05至约1.5重量%，甚至更优选约0.1至约1重量%，最优选约0.2至约0.5重量%本发明水溶性且可热交联亲水性聚合材料。
如果交联涂层和包装溶液中的至少一种包含具有聚乙二醇链段的聚合材料，则包装溶液优选包含足够量的α-含氧多酸或其盐以具有对聚乙二醇链段的氧化降解降低的敏感度。共有未决专利申请(美国专利申请公开No.2004/0116564A1，将其全部并入本文中)公开了含氧多酸或其盐可降低对含PEG聚合材料的氧化降解的敏感度。
典型α-含氧多酸或其生物相容性盐包括但不限于柠檬酸、2-酮戊二酸或苹果酸或其生物相容性(优选眼用相容性)盐。更优选，α-含氧多酸为柠檬酸或苹果酸或其生物相容性(优选眼用相容性)盐(例如钠、钾等)。
根据本发明，包装溶液可进一步包含粘蛋白状材料、眼用有益材料和/或表面活性剂。典型的上述粘蛋白状材料、典型的上述眼用有利材料、典型的上述表面活性剂可用于该实施方案中。
在优选实施方案中，本发明方法进一步包括步骤：将接触透镜浸入具有蓝光吸收性单体单元和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元的蓝光吸收性聚合物溶液中。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，蓝光吸收性聚合物可通过使包含至少一种含羧基乙烯属单体(上述那些中的任一种)和至少一种蓝光吸收性乙烯属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、二氢唑酮基团、环氧基、异氰酸酯基团、氮杂环丙烷基团及其组合，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可润湿性。
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；和共价附着于UV吸收性聚合物层上的水凝胶涂层，其中UV吸收性聚合物包含UV吸收性单体单元和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元，其中水凝胶涂层通过使具有反应性官能团的亲水聚合物或聚合材料通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着于UV吸收性聚合物层上而得到。
以上关于本发明前述方面描述的各个实施方案都可单独或以任何组合用于本发明这一方面中。
前述公开内容能使本领域技术人员实践本发明。可做出本文所述各个实施方案的各种改进、变化和组合。为了能使读者更好地理解具体实施方案及其优点，提出以下实施例。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1
该实施例阐述了根据以下示意图1所示迈克尔加成制备本发明氨基官能化UV吸收性化合物。
氨基官能化Norbloc的制备
Norbloc(即甲基丙烯酸2-[3-(2H-苯并三唑-2-基)-4-羟基苯基]乙基酯)由Aldrich(Cat#413437-100G)得到。半胱胺盐酸盐由Fluka(Cat#30078)得到。0.1N碘水溶液由Acros(Cat#124220010)得到。
在2升三颈圆底烧瓶中，将40.0g(123.7毫摩尔)Norbloc溶于800mLTHF中。在分开的烧瓶中，将15.46g(136.1毫摩尔)半胱胺盐酸盐溶于25mL甲醇中。使用添加漏斗将半胱胺HCl溶液逐滴加入反应烧瓶中，同时搅拌。在反应期间将反应混合物在氮气下清洗。当添加完成时，将反应混合物加热至35℃。当反应混合物达到所需温度时，通过注射器从反应混合物中取出0.25mL试样。将试样放入10mL烧瓶中并用5mL的50/50异丙醇/甲苯稀释，用稀乙酸酸化，然后用0.1N碘水溶液滴定以测定反应的起始硫羟基含量。使用添加漏斗将85mL的2N氢氧化钾溶液加入反应混合物中以使它为碱性的。使反应混合物在氮气下在35℃下混合。通过重复碘滴定监控反应进程以确定何时所有有效硫羟基被消耗。对于完全硫羟基消耗，反应可进行至多65小时。当硫羟基消耗完成时，将反应混合物冷却至室温并转移至4升分液漏斗中。将400mL THF加入漏斗中。将反应混合物用1L盐水萃取2次。将水相抛弃并将有机相经硫酸镁干燥。将溶液过滤并在旋转式蒸发器上除去溶剂。所得产物是清澈的粘性荧光黄液体。反应的收率为约54.0g(90%)。
表征
氨基官能化Norbloc(产物)通过1H-NMR表征；产物与起始材料之间的光谱对比显示5.5和6.1ppm处的甲基丙烯酸酯质子消失。产物的官能度还通过氨基滴定测定；结果显示2.21meq/g(理论2.5meq/g)的氨基官能度。产物的纯度还通过HPLC分析测定；在335nm的检测波长下，氨基官能化Norbloc具有比甲基丙烯酸酯起始材料Norbloc更短的保留时间。通过HPLC分析，产物的典型纯度为85-95%氨基官能材料，其中Norbloc(起始材料)为主要杂质。
Norbloc和胺官能化Norbloc的UV光谱显示迈克尔加成反应不显著影响Norbloc的UV吸收特征。
进行重复合成以显示轻微按比例放大的合成再现性。确认重复产物与先前合成的产物相同。
实施例2
PDMS交联剂I的制备
在4-L烧杯中，将24.13g Na2CO3、80g NaCl和1.52kg去离子水混合以溶解。在分开的4-L烧杯中，将700g双-3-氨基丙基-聚二甲基硅氧烷(Shin-Etsu，MW约11500)溶于1000g己烷中。4-L反应器装配有用涡轮式搅拌器顶入式搅拌和具有微型流量控制器的250-mL添加漏斗。然后将两种溶液装入反应器中，并随着强力搅拌而混合15分钟以产生乳液。将14.5g丙烯酰氯溶于100mL己烷中并装入添加漏斗中。在强力搅拌下经1小时将丙烯酰氯溶液逐滴加入乳液中。当添加完成时，将乳液搅拌30分钟，然后停止搅拌并使相分离过夜。将水相倾析并将有机相用2.0kg溶于水中的2.5%NaCl的混合物洗涤两次。然后将有机相经硫酸镁干燥，用1.0μm尺寸排阻的过滤器过滤，并在旋转式蒸发器上浓缩。将所得油通过高真空干燥而进一步提纯至恒重。通过滴定分析所得产物显示出0.175meq/g的C=C双键。
PDMS交联剂II的制备
在4-L烧杯中，将61.73g Na2CO3、80g NaCl和1.52kg去离子水混合以溶解。在分开的4-L烧杯中，将700g双-3-氨基丙基-聚二甲基硅氧烷(Shin-Etsu，MW约4500)溶于1000g己烷中。4-L反应器装配有用涡轮式搅拌器顶入式搅拌和具有微型流量控制器的250-mL添加漏斗。然后将两种溶液装入反应器中，并随着强力搅拌而混合15分钟以产生乳液。将36.6g丙烯酰氯溶于100mL己烷中并装入添加漏斗中。在强力搅拌下经1小时将丙烯酰氯溶液逐滴加入乳液中。当添加完成时，将乳液搅拌30分钟，然后停止搅拌并使相分离过夜。将水相倾析并将有机相用2.0kg溶于水中的2.5%NaCl的混合物洗涤两次。然后将有机相经硫酸镁干燥，过滤至1.0μm尺寸排阻，并在旋转式蒸发器上浓缩。将所得油通过高真空干燥而进一步提纯至恒重。通过滴定分析所得产物显示出0.435meq/g的C=C双键。
可交联共聚物的制备
2-L夹套反应器装配有加热/冷却回路、回流冷凝器、N2-入口/真空转接器、进料管转接器和顶入式机械搅拌。溶液通过将90.00g上述制备的PDMS交联剂I和30.00g上述制备的PDMS交联剂II溶于480g1-丙醇中而产生。将该溶液装入反应器中并冷却至8℃。将溶液通过抽空至小于15毫巴，保持在真空下15分钟，然后用干氮气再加压而除气。该除气程序重复总计3次。将反应器保持在干氮气覆盖层下。
在分开的烧瓶中，通过将1.50g半胱胺盐酸盐、0.3g AIBN(2-2-偶氮异双丁腈)、55.275g DMA(N,N-二甲基丙烯酰胺)、18.43g HEA(丙烯酸羟基乙酯)和364.5g1-丙醇混合而制备单体溶液。将该溶液用Waterman540滤纸过滤，然后通过除气装置和HPLC泵以3.0mL/分钟的流速加入反应器中。然后随着加热将反应温度升高至68℃约1小时。
在第二烧瓶中，如下制备进料溶液：将4.5g半胱胺盐酸盐和395.5g1-丙醇混合，然后用Waterman540滤纸过滤。当反应器温度达到68℃时，将该溶液通过除气器/HPLC泵经3小时缓慢计量加入反应器中。反应然后在68℃下继续另外3小时，此时停止加热并使反应器冷却至室温。
将反应混合物转移至烧瓶中并在旋转式蒸发器上在真空下在40℃下汽提溶剂直至保留1000g试样。然后将溶液与2000g去离子水缓慢地混合，同时快速搅拌。进一步除去另外的溶剂直至保留约2000g试样。在该汽提方法期间，溶液逐渐变成乳液。将所得材料通过用10kD分子量截留膜超滤而提纯直至渗透物导电性为2.5μS/cm以下。
然后将该乳液装入装配有顶入式搅拌、致冷回路、温度计以及pH计和Metrohm Model718STAT Titrino的分配尖的2-L反应器。然后将反应混合物冷却至1℃。将7.99g NaHCO3装入乳液中并搅拌以溶解。将Titrino通过间歇地加入15%氢氧化钠溶液而设置以将pH保持为9.5。然后使用注射泵经1小时加入11.59mL丙烯酰氯。将乳液搅拌另外一小时，然后通过加入15%HCl溶液设置Titrino以将反应混合物中和。将产物通过再次用10kD分子量截留膜超滤而提纯直至渗透物导电性为2.5μS/cm以下。最终大分子单体通过冻干法(lypophilization)进行分离。
接触透镜的制备
将18.83g上述制备的可交联共聚物溶于约200mL1-丙醇中，浓缩至约70g总溶液重量，并过滤至0.45μm排阻。回收67.94g的26.53%固体的溶液。加入4.503g1%2-羟基-4’-羟基乙基-2-甲基苯基乙基甲酮(-2959，Ciba Specialty Chemicals)溶液，然后将溶液浓缩至具有60%固体的最终配制剂。将200mg配制剂计量加入聚(丙烯)接触透镜模具中并将模具封闭。然后将模具用强度为2.18mW/cm2的紫外光源照射15秒。然后打开模具，将接触透镜从半模中取出。
实施例3
该实施例通过使用称为PAA-F50的式(1)荧光素改性聚丙烯酸(其中m:n～160:1)而阐述本发明方法。
PAA-F50的制备
1H-NMR光谱研究用Bruker Avance400NMR分光计进行。对于UV-Vis光谱研究，使用Perkin Elmer Lambda25分光计。
PAA-F50具有约50kD的分子量，且包含约0.6摩尔%具有荧光生结构部分的单体单元。它如下制备。
将5,0g固体聚丙烯酸(PAA，Mw50.000，来自Polysciences的PAA溶液的冻干产物#00627-250)放入装配有氮气入口管、冷凝器和磁力棒的250ml三颈烧瓶中并通过在环境温度下搅拌而溶于150ml N,N-二甲基甲酰胺DMF(Aldrich#227056)中。向该溶液中加入2.68g N-(3-二甲基氨基丙基)-N’-乙基碳二亚胺盐酸盐(14毫摩尔；EDC-HCl；Fluka#03449)并搅拌，条件是浑浊的溶液变得清澈。向该混合物中缓慢地加入溶于20ml DMF中的4.86g6-氨基荧光素(14毫摩尔；Aldrich#201634)。在搅拌6天以后，将反应混合物倒入1L去离子水中。将该溶液的pH用1N NaOH溶液(Merck#1.09137,1000)调整至pH=7.0，相对去离子水超滤(10kDa膜，Millipore#P2C010V01；15×由水体积交换)，并浓缩(约300ml)。在将该溶液冻干以后，分离7.1g深橙色固体产物。
UV-Vis(pH7.0的PBS溶液)：最大值ε1(321nm)=0.88和ε2(491nm)=6.37[l/(g×cm)]。
聚合物PAA-F50(XFluoresceine)中含荧光素单体单元的摩尔百分数为0.6[摩尔%]。它根据以下方程式在PBS缓冲溶液(pH=7.0)中通过UV-Vis光谱测定：
XFluoresceine=100×A×MA/[w×εF(491nm)×d+A×(MA-MF)][摩尔%] (1)
其中w[g/L]为溶液中PAA-F50的浓度；MA(72g/mol)和MF(419g/mol)分别为共聚物PAA-F50中重复单体单元丙烯酸和荧光素改性丙烯酸(即6-丙烯酰氨基-荧光素)的摩尔质量。A为491nm下的相应UV吸光度；εF(491nm)为共聚物中荧光素结构部分在491nm波长下的吸光度系数：假定这与6-氨基荧光素的相等(εAF(491nm)=76290[l/(mol×cm)]；d为UV测量皿的宽度。
PAA-F50涂覆接触透镜的制备
在将如实施例2所制备的接触透镜从水浴中转移至含有PAA-F50溶液(溶于1-丙醇中，用HCOOH将pH调整至约2.0；0.36g/l PAA-F50，标记等级：0.59摩尔%)的浴中以后，PAA-F50连续扩散到透镜中。PAA-F50向透镜中的该扩散由透镜的着色反映，而透镜颜色的强度随着处理时间的提高而提高(参见图1)。扩散和提高的着色也可通过UV-VIS光谱监控。PAA-F50上荧光结构部分在490nm下的吸光度随时间而提高(参见图2)。透镜上PAA-F50涂层的形成通过首先将接触透镜浸入PAA-F50溶液(以上制备)中约1小时，然后将PAA-F50涂覆的透镜转移并储存在磷酸盐缓冲盐水(PBS)溶液中而阐明。缓冲溶液甚至在储存几周以后保持基本无色。
实施例4
该实施例阐述如何根据本发明优选实施方案制备其上具有UV吸收涂层的接触透镜。
聚(丙烯酸-co-Norbloc)(PAA-N20)的制备
1H-NMR光谱研究用Bruker Avance400NMR分光计进行。对于UV-Vis光谱研究，使用Perkin Elmer Lambda25分光计。丙烯酸由Fluka(#017309111)提供。
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)。它根据以下所述程序制备。
向装配有氮气入口管、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(Norbloc7966；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。使氮气通过该溶液以使溶液除去空气。然后将它加热至60℃，同时搅拌，并加入0.5ml的具有4%二甲基-2,2’-偶氮双-异丁酸酯(V-601，Wako#927-14717)的DMF溶液。通过搅拌将反应混合物保持在60℃下16小时，冷却至环境温度并倒入1.0L乙酸乙酯中。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)中并相对去离子水超滤(3kDa膜，Millipore#P2PLBCV01；15×由水体积交换)。在溶液冻干以后，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)，4.25，6.5-8.1(Haromatic)ppm；所有信号是无组织且宽的。
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集合为XNorbloc=8.1[摩尔%]：
XNorbloc[摩尔%]=100×[3×Aaromatic/(7×A1-4×Aaromatic)]
其中A1为1.02-3,15ppm的质子区域的积分，且Aaromatic为6.5-8.15ppm的芳族信号区域的积分。
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；Na-聚(丙烯酸)作为校准基准)：Mw=36kDa。
PAA-N20涂覆接触透镜的制备
将实施例2中制备的接触透镜浸入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(PBS)溶液冲洗并储存于其中。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光透射在UV-B和UV-A区域(即280-380nm之间的区域)中有效地被阻断(参见图3)。
实施例5
聚[丙烯酸-co-甲基丙烯酰氧基甲基-1-(4-硝基苯基]吡咯烷)(PAA-L20)蓝光吸收剂的制备
指定为PAA-L20的式(3)蓝光吸收性聚合物具有约XXkD的分子量且包含约12.3摩尔%蓝光吸收性单体单元((S)-2-甲基丙烯酰氧基甲基-1-(4-硝基苯基)吡咯烷)。它根据以下所述程序制备：
向装配有氮气入口管、冷凝器、温度计和磁力棒的100ml三颈烧瓶中放入2,0g丙烯酸(28毫摩尔，Fluka#017309111)、0,5g(S)-2-甲基丙烯酰氧基甲基-1-(4-硝基苯基)吡咯烷(1,6毫摩尔；根据M.Yoshida等人，Makromol.Chem.Rapid Commun.，10，(1989)，517制备)和20ml N,N-二甲基甲酰胺(DMF，Aldrich#227056)的混合物。使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0.5ml的具有1%二甲基-2,2’-偶氮双-异丁酸酯(V-601，Wako#927-14717)的DMF溶液。通过搅拌将反应混合物保持在60℃下6小时，冷却至环境温度并倒入500ml乙酸乙酯中。将所得沉淀物通过离心(6000min-1，30min)分离，再溶于轻微碱性水溶液(pH=10.0，用碳酸钠调整)中并相对去离子水超滤(3kDa膜，Millipore#P2PLBCV01；15×由水体积交换)。在溶液冻干以后，分离1,1g深黄色固体产物。
1H-NMR(400MHz；D2O)δ：1,0-2,8(最大值在1,24，1,67，1,80，2,26)，3,15-4,15(最大值在3,49，3,79，4,27)，6,4-7,0(Haromatic)，7,7-8,4(Haromatic)ppm；所有信号是无组织且宽的。
共聚物PAA-L20中含4-硝基苯基吡咯烷单体单元，即蓝光吸收性单体单元(XBlue)的摩尔百分数为XBlue=12,3[摩尔%]，其根据以下方程式通过1H-NMR集合计算：
XBlue[摩尔%]=100×[3×A2/(2×A1-6×A2)]
其中A1为1.0-2.8ppm的质子区域的积分，且A2为7.7-8.4ppm的芳族信号区域的积分。
UV-Vis吸光度(pH7.0的PBS溶液)：两个最大值：吸收系数ε1(235nm)=6.6和ε2(417nm)=15.3[l/(g×cm)]。
通过GPC得到的分子量(具有S2和孔径大小的PSS Suprema柱；PBS溶液作为洗脱液；Na-聚(丙烯酸)作为校准基准)：Mw=36kDa。
实施例6
增链聚二甲基硅氧烷交联剂的制备
在第一步骤中，通过使49.85gα,ω-双(2-羟基乙氧基丙基)-聚二甲基硅氧烷与11.1g异佛尔酮二异氰酸酯(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封端。将反应保持在40℃下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)和50g干MEK的混合物逐滴加入已向其中加入另外0.063g DBTDL的IPDI-PDMS-IPDI溶液中。将反应器保持在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，通过在第三步骤中加入7.77g甲基丙烯酸异氰酸酯基乙酯(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。
作为选择，CE-PDMS可如下制备。将240.43g KF-6001加入装配有搅拌、温度计、低温恒温器、滴液漏斗和氮气/真空入口转接器的1-L反应器中，然后通过施加高真空(2×10-2毫巴)而干燥。然后在干氮气气氛下，然后将320g经蒸馏MEK加入反应器中，并将混合物充分搅拌。将0.235gDBTDL加入反应器中。在将反应器加热至45℃以后，将45.86g IPDI通过添加漏斗经10分钟加入反应器中，同时温和搅拌。将反应在60℃下保持2小时。然后将溶于452g经蒸馏MEK中的630g KF-6002加入并搅拌直至形成均匀溶液。加入0.235g DBTDL，并将反应器在干氮气覆盖层下保持在55℃下过夜。第二天通过闪蒸除去MEK。将反应器冷却，然后将22.7g IEM装入反应器中，其后加入0.235g DBTDL。在3小时以后，加入另外3.3g IEM，并使反应进行过夜。下一天将反应混合物冷却至18℃以得到CE-PDMS大分子单体。
透镜配制剂的制备
透镜配制剂通过将组分溶于1-丙醇中而制备以具有以下组成：约32重量%上述制备的CE-PDMS大分子单体，约21重量%TRIS-Am，约23重量%DMA，约0.6重量%L-PEG(N-(羰基-甲氧基聚乙二醇-2000)-1,2-二硬脂酰-sn-甘油-3-磷基乙醇胺，钠盐)，约1重量%Darocur1173，约0.1重量%visitint(在TRIS中的5%铜酞菁蓝色颜料分散体)，约0.8重量%DMPC(1,2-二肉豆蔻酰-sn-甘油-3-胆碱磷酸)，约200ppm H-tempo(4-羟基-2,2,6,6-四甲基-1-哌啶氧基)和约22重量%1-丙醇。
透镜的制备
透镜通过在类似于美国专利Nos.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(石英阴半模和玻璃阳半模)中由以上制备的透镜配制剂铸造模塑而制备。将模具中的透镜配制剂用UV辐射(13.0mW/cm2)照射约24秒。将模制透镜用MEK萃取。
具有UV吸收性和蓝光吸收性涂层的接触透镜的制备
将以上制备的接触透镜浸入含有PAA-N20溶液(溶于1-丙醇中的3,6g/L PAA-N20，用HCOOH调整至pH～2.0)的浴中约20分钟，用1-丙醇冲洗，随后浸入具有PAA-L20溶液(3,6g/L PAA-L20，用HCOOH调整至pH～2.0)的浴中。图4显示所得接触透镜不仅吸收280-380nm范围，而且吸收380-480nm范围内的UV光，即不仅是关于具有UV吸收剂类型1性能的透镜的标准。它还满足蓝光吸收性透镜的性能。
Claims (17)
1.制备UV吸收性接触透镜的方法，所述方法包括步骤：得到眼用透镜，优选接触透镜；将眼用透镜浸入包含第一有机溶剂和UV吸收性聚合物的涂料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吸收性单体单元和至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元；和任选，但优选使具有反应性官能团的亲水聚合物或聚合材料共价附着在UV吸收涂层上以形成水凝胶涂层，其中水凝胶涂层通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着在UV吸收涂层上。
2.根据权利要求1的方法，其中UV吸收性单体单元各自包含苯并三唑或二苯甲酮结构部分。
3.根据权利要求1或2的方法，其中UV吸收性聚合物通过使包含至少一种含羧基乙烯属单体和至少一种UV吸收性乙烯属单体的可聚合混合物在乙烯属单体的存在或不存在下共聚而得到，条件是含羧基乙烯属单体以至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%的量存在于可聚合组合物中。
4.根据权利要求3的方法，其中UV吸收性乙烯属单体选自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；其中含羧基乙烯属单体选自丙烯酸、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UV吸收性化合物与具有至少约50摩尔%，优选至少约60摩尔%，更优选至少约70摩尔%，甚至更优选至少约80摩尔%，最优选至少约90摩尔%含羧基单体单元的前体聚合物在偶联反应中反应而得到，其中UV吸收性化合物由式I、II、III或IV表示：
其中：
R1、R2和R3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，或其中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， 或其中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个碳原子的烷芳基二价基团、具有至多40个碳原子的亚芳烷基二价基团，或者具有式–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–(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0-20的数，条件是(w1+w2+w3)的和为1-60，且Xb和Xc相互独立地为共价键、羰基、 其中R”为以上定义的；且
Y和Y1相互独立地为二氢唑酮基团、环氧基、异氰酸酯基团、氮杂环丙烷基团或–NHR的氨基，其中R为氢或C1-C20未被取代或经取代的线性或支化烷基。
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)含羧基乙烯属单体和含氨基乙烯属单体的共聚物，其中含羧基乙烯属单体为丙烯酸或C1-C12烷基丙烯酸或其组合，其中含氨基乙烯属单体选自(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；或(4)含羧基乙烯属单体和一种或多种亲水乙烯属单体的共聚物，其中含羧基乙烯属单体为丙烯酸和C1-C12烷基丙烯酸或其组合，其中所述一种或多种亲水乙烯属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-羟基乙酯、(甲基)丙烯酸羟基丙酯、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。
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-co-甲基丙烯酸)、聚[C2-C12烷基丙烯酸-co-(甲基)丙烯酸]、聚(N,N-2-丙烯酰氨基羟基乙酸)、聚[(甲基)丙烯酸-co-丙烯酰胺]、聚[(甲基)丙烯酸-co-乙烯基吡咯烷酮]、聚[C2-C12烷基丙烯酸-co-丙烯酰胺]、聚[C2-C12烷基丙烯酸-co-乙烯基吡咯烷酮]、水解聚[(甲基)丙烯酸-co-乙酸乙烯酯]、水解聚[C2-C12烷基丙烯酸-co-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，其进一步包括步骤：将其上具有UV吸收涂层的眼用透镜用水与至多约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重量%第二有机溶剂的混合物冲洗，其中第一有机溶剂以至少约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重量%的量存在于涂料溶液中。
9.根据权利要求1-8中任一项的方法，其中所述方法包括步骤：使具有反应性官能团的亲水聚合物或聚合材料共价附着于UV吸收涂层上以形成水凝胶涂层，其中水凝胶涂层通过各自在UV吸收涂层的一个羧基与亲水聚合物或聚合材料的一个反应性官能团之间形成的键共价附着于UV吸收涂层上。
10.根据权利要求9的方法，其中亲水聚合物和亲水性聚合材料的反应性官能团为氮杂环丁基团、环氧基、异氰酸酯基团、氮杂环丙烷基团、二氢唑酮基团、氨基、羧基及其组合。
11.根据权利要求9的方法，其中水凝胶涂层通过使部分交联聚合材料交联在UV吸收涂层上而形成，其中部分交联聚合材料为水溶性的且包含三维网络和在网络内的反应性官能团，所述反应性官能团选自氮杂环丁基团、环氧基、异氰酸酯基团、氮杂环丙烷基团、二氢唑酮基团、氨基、羧基及其组合，优选氮杂环丁基团。
12.根据权利要求10的方法，其中部分交联聚合材料包含：(i)约20至约95重量%的衍生自表氯醇官能化聚胺或聚酰胺胺的第一聚合物链，(ii)约5至约80重量%的衍生自至少一种亲水性增强剂的亲水性结构部分或第二聚合物链，所述亲水性增强剂具有至少一个选自氨基、羧基、硫羟基及其组合的反应性官能团，其中亲水性结构部分或第二聚合物链通过各自在表氯醇官能化聚胺或聚酰胺胺的一个氮杂环丁基团与亲水性增强剂的一个氨基、羧基或硫羟基之间形成的一个或多个共价键共价连接在第一聚合物链上，和(iii)氮杂环丁基团，其为第一聚合物链的一部分或共价连接在第一聚合物链上的侧基或端基，优选第一和第二聚合物链中的至少一个包含UV吸收性单体单元。
13.根据权利要求12的方法，其中使亲水性聚合材料共价连接的步骤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部分交联聚合材料的包装溶液中压热处理约20-90分钟而进行。
14.根据权利要求9-13中任一项的方法，其中用于形成水凝胶涂层的亲水聚合物或亲水性聚合材料包含UV吸收性结构部分。
15.根据权利要求1-14中任一项的方法，其中UV吸收涂层进一步包含蓝光吸收性聚合物。
16.根据权利要求1-15中任一项的方法，其中眼用透镜为硅水凝胶接触透镜，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可润湿性。
17.根据权利要求1-16中任一项的方法得到的眼用透镜。
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| CN110337462A (zh) * | 2017-02-24 | 2019-10-15 | 索尔维特殊聚合物美国有限责任公司 | 用于处理聚合物制品的表面层的uv稳定剂溶液 |
| TWI705051B (zh) * | 2016-02-22 | 2020-09-21 | 瑞士商愛爾康公司 | Ｕｖ/可見-吸收性乙烯基單體以及其用途 |
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| CN108369291A (zh) * | 2015-12-15 | 2018-08-03 | 诺华股份有限公司 | 用于将稳定的涂层施加在硅酮水凝胶接触镜片上的方法 |
| CN108369291B (zh) * | 2015-12-15 | 2021-07-20 | 爱尔康公司 | 用于将稳定的涂层施加在硅酮水凝胶接触镜片上的方法 |
| TWI705051B (zh) * | 2016-02-22 | 2020-09-21 | 瑞士商愛爾康公司 | Ｕｖ/可見-吸收性乙烯基單體以及其用途 |
| CN110337462A (zh) * | 2017-02-24 | 2019-10-15 | 索尔维特殊聚合物美国有限责任公司 | 用于处理聚合物制品的表面层的uv稳定剂溶液 |
| CN110337462B (zh) * | 2017-02-24 | 2023-09-15 | 索尔维特殊聚合物美国有限责任公司 | 用于处理聚合物制品的表面层的uv稳定剂溶液 |
| CN111801389A (zh) * | 2018-03-02 | 2020-10-20 | 强生视力健公司 | Uv和高能可见光的可聚合吸收剂 |
| CN111801389B (zh) * | 2018-03-02 | 2023-01-20 | 强生视力健公司 | Uv和高能可见光的可聚合吸收剂 |
| CN113939545A (zh) * | 2019-07-01 | 2022-01-14 | 株式会社尼康 | 化合物、树脂前体、固化物、光学元件、光学系统、照相机用更换镜头、光学装置、接合透镜以及接合透镜的制造方法 |
| CN113939545B (zh) * | 2019-07-01 | 2023-05-30 | 株式会社尼康 | 化合物、树脂前体、固化物、照相机用更换镜头、光学装置、接合透镜及其制造方法 |
| CN115466349A (zh) * | 2022-09-28 | 2022-12-13 | 长春工业大学 | 一种二苯甲酮衍生物防紫外线硅水凝胶隐形眼镜及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103917899B (zh) | 2018-04-03 |
| US20130095235A1 (en) | 2013-04-18 |
| SG11201400228WA (en) | 2014-05-29 |
| EP2766750B1 (en) | 2016-02-03 |
| US9005700B2 (en) | 2015-04-14 |
| CA2851668C (en) | 2016-08-16 |
| CA2851668A1 (en) | 2013-04-18 |
| HUE029018T2 (en) | 2017-02-28 |
| EP2766750A1 (en) | 2014-08-20 |
| MY164605A (en) | 2018-01-30 |
| JP2014534467A (ja) | 2014-12-18 |
| JP6017572B2 (ja) | 2016-11-02 |
| WO2013055746A1 (en) | 2013-04-18 |
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