CN1243846A - 具有亲水性涂层的生物医学装置 - Google Patents

具有亲水性涂层的生物医学装置 Download PDF

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CN1243846A
CN1243846A CN99108449A CN99108449A CN1243846A CN 1243846 A CN1243846 A CN 1243846A CN 99108449 A CN99108449 A CN 99108449A CN 99108449 A CN99108449 A CN 99108449A CN 1243846 A CN1243846 A CN 1243846A
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D·G·范德拉安
D·C·图尔纳
J·M·伍德
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Abstract

提供具有稳定性、亲水性及抗微生物性涂层的生物医学装置,该涂层是使用偶合剂将含羧基的亲水性涂敷剂经由酯或酰胺键链结至其表面而形成。

Description

具有亲水性涂层的生物医学装置
本发明涉及含涂层的装置，具体地说，本发明提供生物医学装置，其表面经由酯或酰胺键，将涂层偶合至表面而形成稳定性、亲水性及抗微生物性的涂层。
在人体内部及外部使用的装置已经熟知，此种装置表面的化学组合物在主导该装置的整体效应时，扮演关键性的角色，例如包括导尿管、移植片固定模、镜片及植入物的许多装置，必须具有在生物学上无污染的表面，也就是说蛋白质、脂类及细胞将不会粘附在表面上，镜片也必须可经由眼液湿化，以便确保戴用者的舒适性，此外，适宜提供具有抗微生物表面的此种装置。
曾经发展多种不同的方法，供涂敷装置的表面使其具有所需的特色，但是，仍然需求可提供稳定性、亲水性及抗微生物性涂层的简单、有效方法。
本发明提供一种简单、经济的方法供生产具有稳定的表面涂层的装置，该涂层同时具有亲水性及抗微生物性，“抗微生物性”是指与不含涂层的表面比较时，粘附在装置表面的细菌减少约30％或更多。
在一个实施方案中，本发明提供一种生物医学装置的制法，包括：基本上由，由使生物医学装置的至少一面与有效剂量的至少一种偶合剂和含涂敷有效量的羧基官能聚合物接触，在表面产生稳定性、亲水性及抗微生物性的涂层组成。在另一个实施方案中，本发明提供生物医学装置，包括，基本上由，由在该装置的至少一个表面上，经由至少一种偶合剂偶合含羧基官能基聚合物的涂层组成。
“生物医学装置”是指设计用在人类组织或流体内部或上面或两者的任何装置，此种装置的实施例包括但不限於移植片固定模、植入物、导尿管及眼镜，在一个较佳的具体实施例中，生物医学装置为眼镜，包括但不限於隐形眼镜或人工晶状体(intraocularlenses)，此装置更宜为隐形眼镜。
本发明意外地发现可使用羧基官能化聚合物为生物医学装置提供稳定性、抗微生物性以及亲水性的涂层，“稳定性”是指将涂层进行高压消毒、用清洁剂清洗及/或用盐水冲洗时，不会实质上改变涂层的化学性质，本发明的涂层可用某些偶合剂经由酯键、酰胺键或其组合，偶合至装置的表面上。
可在本发明中使用的偶合剂包括但不限於碳化二亚胺类、N，N′-羰基二咪唑、磷酰氯、四氯化钛、硫酰氯氟、氯磺酰基异氰酸酯、碘化磷、三丁胺的吡啶盐、二氯磷酸苯酯、聚磷酸酯、氯硅烷类等，以及三丁磷与异氰酸苯酯、氯甲酸烷酯与三乙胺、2-氯-1，3，5-三硝基苯与吡啶、甲基磺酰氯与二乙胺、及三苯基膦、四氯化碳与三乙胺的混合物，较佳的偶合剂为碳化二亚胺类，更宜为1-乙基-3-(3-二甲胺基丙基)碳化二亚胺及二环己基碳化二亚胺。
虽然任何数量的聚合物，例如含伯或仲胺基、羟基、羧基的物质或其混合物，可用於提供亲水性的涂层，发现使用羧基官能化亲水性聚合物，优选为聚(丙烯酸)，提供的涂层当与其他此种涂层比较时，具有优越的亲水性，而且这些涂层提供抗微生物性的附加优点。
合适的羧基官能化亲水性聚合物实施例包括但不限於聚(丙烯酸)、聚(甲基丙烯酸)、聚(马来酸)聚(衣康酸)、(甲基)丙烯酸、丙烯酸、马来酸、衣康酸与任何反应性乙烯基单体的嵌段或无规共聚物等及其混合物，较佳的羧基官能基亲水性聚合物为聚(丙烯酸)或聚(甲基丙烯酸)，更优选使用聚(丙烯酸)。
羧基官能化聚合物可具有任何分子量，聚合物较宜具有相对高的分子量，或约100,000至约10,000,000，更宜约100,000至约4,000,000克/摩尔，最宜约100,000至约1,000,000克/摩尔。
装置的一或多个表面可使用本发明方法涂敷，供本发明使用的合适表面为含羟基、胺基、或其混合物的任何表面，此表面较宜由硅酮弹性体、水凝胶、或含硅酮的水凝胶制成，此表面更宜为硅氧烷，包括但不限於聚二甲基硅氧烷大分子、甲基丙烯酰氧基丙基聚烷基硅氧烷类及其混合物、硅酮水凝胶或水凝胶例如ETAFILCONTM。
在本发明的方法及装置中，如果待涂敷的表面物质不含所需的官能基团，可将这些官能团引入表面物质内，例如可将一或多种含羟基的单体加入用於形成表面的聚合物内而引入羟基，此种含羟基单体的实施例包括但不限於乙二醇、丙二醇、甘油、四甘醇等的单(甲基)丙烯酸酯，引入的胺基可使用但不限於胺基醇类例如胺基乙醇、叔丁基胺基乙醇的(甲基)丙烯酸酯、或二胺类例如双胺基丙烷的(甲基)丙烯酰胺。
或者是，可以使用胺或羟基官能化、含硅酮的单体或大分子单体，将羟基或胺基官能度引入表面，合适的含羟基的大分子单体包括但不限於下列结构的含硅酮的直链或支链羟基烷基胺基官能基单体：
Figure A9910844900061
其中：n为0至500，m为0至500，且n+m＝10至500，较宜为20至250；R2、R4、R5、R6及R7各独立地为经取代或优选为未经取代的含1至10个碳原子的单价烷基，或为经取代或优选为未经取代的芳基，其合适的取代基包括醇、酯、胺、酮、羧酸或醚基；R1、R3及R8各独立地为经取代或优选为未经取代的含1至30个碳原子的单价烷基，或为经取代或优选为未经取代的芳基，其合适的取代基包括醇、酯、胺、酮、羧酸或醚基，且至少其中一个R1、R3及R8为下式结构：
Figure A9910844900062
其中R9为可连接N至Si的任何基团，包括但不限於直链或支链含1至约10个碳原子的二价烷基或醚基，R10及R11各独立地为H、经取代后未经取代的含1至5个碳原子的单价烷基、经取代或未经取代的芳基，其合适的取代基为经醇、酯、胺、酮、羧酸或醚基取代，或下列结构：
Figure A9910844900063
其中R14为H或单价(甲基)丙烯酰基、苯乙烯基、乙烯基、烯丙基、或N-乙烯基内酰胺可聚合的基团且较宜为H或甲基丙烯酰基；R16为H、经取代或未经取代的含1至6个碳原子的单价烷基、经取代或未经取代的芳基，其合适的取代基为醇、酯、胺、酮、羧酸或醚基，或(甲基)丙烯酸酯、苯乙烯基、乙烯基、烯丙基、或N-乙烯基内酰胺可聚合的基，且较宜为经醇取代的含1至6个碳原子的烷基或为甲基丙烯酸酯；R12、R13及R15独立地为H、经取代或未经取代的含1至6个碳原子的单价烷基、经取代或未经取代的芳基，其合适的取代基包括醇、酯、胺、酮、羧酸或醚基，或R12及R15或R13及R15形成一个环结构，其条件是在单体上的至少一些结构II基团为可聚合化的基团，较宜R12、R13及R15为H。
可在本发明中使用的含硅酮聚合物也可为引入一或多种亲水性单体的共聚物，在本发明中用於制造水凝胶的亲水性单体可为供形成水凝胶使用的任何已知单体。
经由本发明方法在形成表面涂层中使用的较佳亲水性单体为含丙烯酸或乙烯基的物质，含丙烯酸的单体含(CH2＝CRCOX)基，其中R为H或CH3，且X为O或N，此种单体的实施例包括但不限於N，N-二甲基丙烯酰胺、甲基丙烯酸2-羟基乙酯、甲基丙烯酸甘油酯、2-羟基乙基甲基丙烯酰胺、单甲基丙烯酸聚乙二醇酯、甲基丙烯酸、丙烯酸等。
含乙烯基的单体是指含(-CH＝CH2)基的单体，此种单体的实施例包括但不限於N-乙烯基吡咯烷酮、及N-乙烯基-N-甲基乙酰胺、N-乙烯基-N-乙基乙酰胺、N-乙烯基-N-乙基甲酰胺、N-乙烯基甲酰胺等N-乙烯基内酰胺，较佳的单体为N-乙烯基吡咯烷酮。
可在形成本发明的表面中使用的其他亲水性单体包括但不限於一或多个终端羟基被含可聚合的双键的官能基取代的聚氧化乙烯多元醇类，实施例包括但不限於聚乙二醇，乙氧基化的烷基葡糖苷，及乙氧基化的双酚A与一或多当量封端基例如甲基丙烯酸异氰酸根合乙酯、甲基丙烯酸酐、甲基丙烯酰氯、乙烯基苯甲酰氯等反应所产生的聚乙二醇，其中含一或多个终端可聚合的且经由连接部分例如氨基甲酸酯或酯基键结至聚乙二醇的烯羟基。
亲水性单体的其他实施例揭示在美国专利5,070,215及4,910,277号中，其整份并入本文供参考，较佳的亲水性单体为N，N-二甲基丙烯酰胺、甲基丙烯酸2-羟基乙酯、甲基丙烯酸甘油酯、2-羟基乙基甲基丙烯酰胺、N-乙烯基吡咯烷酮、聚单甲基丙烯酸乙二醇酯、及(甲基)丙烯酸，最宜使用N，N-二甲基丙烯酰胺。
在本发明的方法中，待涂敷的表面与聚合物及至少一种偶合剂在任何惯用方法下接触，例如可将装置放在聚合物及溶剂的溶液中并加入偶合剂，或者是，聚合物或装置表面先用偶合剂处理，然后将表面放在聚合物溶液内。
适合在本发明中使用的溶剂为可同时溶解羧基官能基聚合物及偶合剂的溶剂，本涂覆法较宜在水或水溶液中进行，该溶液较宜含缓冲液及盐类，碳化二亚胺当中的1-乙基-3-(3-二甲胺基丙基)碳化二亚胺(“EDC”)在水溶液中有效，且因此是最佳的偶合剂。
偶合剂既可单独使用或与能够稳定所形成的任何反应性中间体的试剂结合使用，例如EDC可与作为稳定性的N-羟基琥珀酰亚胺一起使用，此外，可能需要调整溶液的pH，以便使酯或酰胺键的形成最佳化，pH较宜调整至约2.0至约8.0，更宜为约4.5至约5.0。
使用的偶合剂的有效偶合量是足够将聚合物偶合至装置表面的量，偶合剂的具体用量将决定於表面的化学以及选用的聚合物及偶合剂，通常使用约0.01至约10重量％，较宜约0.01至约5.0，更宜约0.01至约1重量％的涂敷溶液，涂敷溶液是指含一或多种溶剂、偶合剂、及缓冲液的聚合物，通常每个镜片使用的涂敷溶液为约0.1至约100克，较宜约0.5至约50克，更宜约1至约10克。
使用的聚合物的有效涂敷量是指足够在表面涂敷至所要程度的量，通常聚合物的使用量为约0.001至约100，较宜约0.01至约50，更宜约0.01至约10重量％的涂敷溶液。
温度及压力对本发明方法并不重要，且本方法可方便地在室温及大气压力下进行，但是在一个较佳的具体实施例中，使用的温度为约30至约60℃，使用的接触时间是足够在表面上涂覆至所要程度的时间长度，如果表面与偶合剂-聚合物溶液接触，通常接触时间为约1分钟至约24小时，较宜为约1至约120分钟，更宜为约1分钟至约60分钟。
如果表面先只用偶合剂处理，接触时间将为约1至约120，较宜为约2至约60分钟，然后如上所述将表面与聚合物-溶剂溶液接触。
接触后，用水或缓冲盐水清洗以去除未反应的聚合物、偶合剂、溶剂及副产物，视需要来定可将涂敷后的表面在水中加热以萃取残留的涂敷剂、偶合剂及副产物，分解可能形成的任何偶合剂-稳定剂复合物。
在本发明的一个具体实施例中，涂覆羧基官能基聚合物后，可将涂覆后的表面进一步改性，例如涂覆后的表面可和能与涂层的官能基反应的单体或聚合物反应，此种进一步的反应可以使用任何合适的偶合剂进行，包括上文叙述的偶合剂，可以使用的单体实施例包括但不限於醇类例如甲醇及乙醇、多元醇类例如乙二醇及甘油、胺类例如正丁胺、甲胺、氨、乙醇胺或二乙醇胺等，但是一般技术人员将会了解到改性用单体或聚合物的选择决定於涂敷后的表面所要改良的程度。
一般技术人员将会了解，用于制造由本发明方法涂敷的表面的配制剂可含其他单体及添加剂，例如可以使用紫外线吸收单体、反应性颜料、加工助剂等。
本发明将参照下列非限定性的实施例进一步说明。
                 实施例
                  制备1
根据下列步骤制备含硅酮的隐形眼镜，将500克α、ω-双胺基丙基聚二甲基硅氧烷(分子量5000)及68克甲基丙烯酸缩水甘油酯混合并在100℃下搅拌加热10小时，用1500毫升乙腈萃取产物五次以去除残留的甲基丙烯酸缩水甘油酯而得到无色的油，红外光谱如下：3441厘米-1，2962厘米-1，1944厘米-1，1725厘米-1，1638厘米-1，1612厘米-1，1412厘米-1。
将25.35重量％此反应产物、25.35重量％3-甲基丙烯酰氧基丙基双(三甲硅烷氧基)甲基硅烷(“MBM”)、27.3重量％N，N-二甲基丙烯酰胺(“DMA”)、0.31重量％市售的DAROCURTM 1173的2-羟基-2-甲基-1-苯基丙-1-酮、13.2重量％3-甲基-3-戊醇及8.8重量％八甲基环四硅氧烷的掺混物在隐形眼镜模具中使用UV光固化，将模具打开并将镜片释出至异丙醇中，然后转移至硼酸盐缓冲溶液中。
               实施例1
将170制备1的镜片浸入含1.5重量％(分子量250,000)聚(丙烯酸)的硼酸盐缓冲盐水溶液中，加入0.62克EDC并使混合物在室温下搅拌1小时，然后用新鲜的盐水溶液清洗镜片五次，在涂覆前后使用Wilhelmy天平测量与硼酸盐缓冲盐水的动态接触角，结果列在表1。
涂覆后的镜片在121℃下高压消毒五次并测量动态接触角，结果列在表1。
使用数字式摩擦器及纯化水清洗液、异丙醇(15.7重量/重量％)、poloxamer 407、及amphoteric 10(市售MIRAFLOWTM)的清洁剂清洗数个经高压消毒后的镜片，用盐水冲洗镜片，在涂覆前后用经硼酸盐缓冲的盐水测量经高压消毒及清洗后的镜片的动态接触角，结果列在表1。
                    比较实施例1
将五个制备1的镜片浸泡在与实施例1相同的含1.5重量％(分子量250,000)聚(丙烯酸)但是没有加入EDC的经硼酸盐缓冲的盐水溶液中，将混合物在室温下搅拌1小时，然后用新鲜的盐水溶液冲洗镜片五次，一个镜片用数字式摩擦器及MIRAFLOWTM清洗，镜片用盐水冲洗且无法湿化。
                    制备2
将2.48克1，3-双(3-胺基丙基)四甲基二硅氧烷、83.62克八甲基环四硅氧烷、13.37克3-胺基丙基甲基二乙氧基硅烷、0.1克氢氧化钾及10.0克水混合并加热至145℃，搅拌并经由共沸去除水及乙醇，将混合物冷却至60℃并加入0.13克醋酸，将混合物搅拌1小时并经由硅藻土过滤，在145℃，一大气压下加热将产物去挥发分。
将制造的10克胺基官能化聚硅氧烷液体与1.33克缩水甘油及0.729克甲基丙烯酸缩水甘油酯混合，观察到中度放热，使混合物反应三天，在此期间变成非常粘稠，产物为侧基羟基烷基胺官能化的含硅酮单体。
将12.06单体组分与7.24克DMA、4.82克甲基丙烯酰氧基丙基三(三甲基硅氧烷基)硅烷(“TRIS”)及0.06克DAROCURETM1173在隐形眼镜模具中经由暴露在UV光下而共聚合，所得的镜片浸泡在异丙醇中以去除任何残留的单体，然后在经硼酸盐缓冲中的溶液中平衡化。
                      实施例2
将25个制备2的镜片浸泡在46.46克经硼酸盐缓冲的盐水中并加入1.95克35重量％的聚(丙烯酸)(分子量250,000)的水溶液，加入0.09克EDC并将混合物在室温下搅拌5分钟，然后用新鲜的盐水溶液冲洗这些镜片4次，如同实施例1的方法测量动态接触角，结果列在表1。
                       实施例3
将30个制备1的镜片浸泡在室温下的29.3克EDC在经硼酸盐缓冲的盐水中的1.0％溶液1小时，将镜片转移至132克聚(丙烯酸)(分子量250,000)在经硼酸盐缓冲的盐水中的3.0％溶液，在室温下经1小时后，加入0.38克EDC，在室温下经1小时后，用经硼酸盐缓冲的盐水冲洗镜片，然后将其放入60克甘油在经硼酸盐缓冲的盐水中的5％溶液，加入0.60克EDC，在室温下经1小时后，用新鲜的经硼酸盐缓冲的盐水溶液冲洗这些镜片五次，发现这些镜片可以非常湿润化。
                      制备3
隐形眼镜通过如下制造：将15重量％平均分子量为4,600的二甲基丙烯酸聚乙二醇酯，2.0重量％1，3-双(3-甲基丙烯酰氧基丙基)四(三甲硅氧烷基)二硅氧烷，30重量％平均分子量为350的甲基丙烯酸甲氧基聚乙二醇酯，30.18重量％TRIS，15重量％甲基丙烯酸3-(全氟-5-甲基己基)-2-羟基丙酯，3.0重量％甲基丙烯酸，0.80重量％IRGACURETM 1850，4.0重量％NORBLOCTM7966，以及0.02重量％的掺混在稀释剂聚丙二醇(平均20个重复单元)乙基己醇中的Reactive Blue 2甲基丙烯酸2-羟基乙酯加合物(1∶1重量比例的反应性单体与稀释剂的重量比例为60∶40)的掺混物加入镜片模具内并用可见光照射模具，将所得的镜片浸泡在异丙醇中以去除任何残留的单体，然后在经硼酸盐缓冲的溶液中平衡化。
                        实施例4
将20个制备3的镜片浸泡在含0.8重量％聚(丙烯酸)(分子量250,000)的40毫升经硼酸盐缓冲的盐水溶液，加入0.06克EDC，使混合物在室温下搅拌1小时，然后用去离子水重复清洗镜片，测量动态接触角，且结果列在表1。
                  制备4
如同实施例3的方法，但是使用2.0重量％2-羟基乙基甲基丙烯酸酯及13重量％甲基丙烯酸3-(全氟-5-甲基己基)-2-羟基丙酯制备镜片。
                 实施例5
将50个制备4的镜片浸泡在100毫升含0.88重量％聚(丙烯酸)(分子量250,000)的经硼酸盐缓冲的盐水溶液中，加入0.15克EDC，使混合物在室温下搅拌1小时后，用经硼酸盐缓冲的盐水重复冲洗镜片，发现这些镜片可以非常湿润化。
                 制备5
将12.5克KOH加入在高温/高压反应器内的350克20摩尔可从Americol Corp.，N.J.以GLUCAMTMP-20获得的甲基葡萄糖丙氧基化物，将混合物加热至105℃并在氮气吹扫下搅拌30分钟，然后抽真空，经再重复吹扫/真空两次以上后，使压力增加至10psi且温度上升至125℃，历时7小时逐渐加入1922克环氧丙烷，同时保持压力为30-40psi且温度为135℃，持续搅拌过夜后，根据类似步骤加入947克环氧乙烷，用9.1克磷酸将产物中和，经由硅藻土过滤，得到微雾状的液体，其羟基值为28.3毫克KOH/克。
在200克此产物、21.0克三乙胺及342毫克N，N-二甲胺基吡啶於600克无水乙二醇二甲醚的溶液中，在40℃下历时7至8小时将在250克无水乙二醇二甲醚中的32.1克甲基丙烯酸酐逐滴加入反应烧瓶，使反应在40℃下搅拌7天。
使反应温度降至25℃并加入100毫升去离子水，用5％盐酸溶液将反应混合物的pH调整成7.0，加入600克AMBERLITETM IRA 96并搅拌混合物1.5小时，经由过滤去除AMBERLITETM IRA 96，在30至35℃和减压下将混合物挥发，加入约1升的氯仿，所得的液体用等体积的碳酸氢钠5％水溶液清洗两次及用饱和的氯化钠清洗一次，使有机层通过400克硅胶床，加入100毫克4-甲氧基苯酚并在减压下去除氯仿，加入约75毫升甲醇后在减压下将残留的氯仿去除而得到大分子化合物。
将11.2％制备5的大分子化合物、40％TRIS、28％DMA、0.8％DAROCURTM 1173及20％1-己醇制成混合物，使混合物在隐形眼镜模具中通过暴露在UV光下30分钟而固化，打开模具并将镜片放入异丙醇及水的混合物中，用异丙醇冲洗，并放在经硼酸盐缓冲的盐水中。
                  实施例6
将35个制备5的镜片浸泡在含1.37重量％聚(丙烯酸)(分子量250,000)的184毫升经硼酸盐缓冲的盐水溶液，加入0.030克EDC，使混合物在室温下搅拌1小时，然后用去离子水重复清洗镜片，测量动态接触角，且结果列在表1。
                  制备6
将3.26克制备5的大分子化合物与12.5 TRIS、8.78克DMA、0.27克DAROCURTM 1173、0.96克甲基丙烯酸2-羟基乙酯、0.0078克甲基丙烯酸2-羟基乙酯和反应性盐2的加合物及5.03克1-己醇混合，使混合物在隐形眼镜模具中通过暴露在UV光下30分钟而固化，打开模具并将镜片放入异丙醇及水的混合物中，用异丙醇冲洗，并放在经硼酸盐缓冲的盐水中。
                  实施例7
将35个制备6的镜片浸泡在含1.37重量％聚(丙烯酸)(分子量250,000)的184毫升经硼酸盐缓冲的盐水溶液，加入0.03克EDC，使混合物在室温下搅拌1小时，然后用经硼酸盐缓冲的盐水溶液重复清洗镜片，测量动态接触角，且结果列在表1。
                  实施例8
将35个ETAFILCONTM的镜片浸泡在含1.37重量％聚(丙烯酸)(分子量250,000)的184毫升经硼酸盐缓冲的盐水溶液，加入0.030克EDC，使混合物在室温下搅拌1小时，然后用经硼酸盐缓冲的盐水溶液重复冲洗镜片，所得的镜片可以非常湿润化及润滑。
                 实施例9
将2个制备1的镜片放在含10％EDC及0.25％聚(丙烯酸)(分子量750,000)的室温下溶液中，经20分钟后，取出镜片并用经硼酸盐缓冲的盐水溶液冲洗，此镜片可以湿润化。
                     表1
    实施例 未涂覆镜片的前进角(°) 涂覆镜片的前进角(°) 未涂覆镜片的后退角(°)   涂覆镜片的后退角(°)
    1     135     45     62     40
 1(经高压消毒)     ---     50     ---     39
  1(经高压消毒及清洗)     ---     58     ---     52
    2     114     32     56     35
 2(经高压消毒)     ---     35     ---     45
  2(经高压消毒及清洗)     ---     35     ---     39
    4     148     50     50     44
 4(经高压消毒)     ---     45     ---     45
  4(经高压消毒及清洗)     ---     49     ---     42
    6     111     44     52     44
 6(经高压消毒)     ---     55     ---     50
  6(经高压消毒及清洗)     ---     71     ---     55
    7     111     46     52     49
 7(经高压消毒)     ---     39     ---     44
  7(经高压消毒及清洗)     ---     52     ---     50
    8     76     58     48     54
 8(经高压消毒)     ---     56     ---     39
  8(经高压消毒及清洗)     ---     39     ---     44
              实施例10及11
将铜绿假单胞菌ATCC#15442(得自ATCC，Rockville，Maryland)的培养液在150毫升的胰蛋白酶大豆肉汤中成长过夜，制备含1×108cfu/毫升的经标准化磷酸盐缓冲的盐水(PBS)清洗的细菌接种物，将细菌施加至实施例1至8的镜片上，包括涂覆及没有涂覆聚(丙烯酸)，用PBS清洗隐形眼镜，各清洗后的镜片在玻璃小瓶中与2毫升标准化的细菌接种物混合，该小瓶在100rpm下的旋转摇动培养器中在35℃下摇动2小时，用PBS清洗各镜片，放入含0.05％TWEENTM 80的10毫升PBS中，并在2000rpm及室温下旋转3分钟，从所得的上清液测定能生存的细菌，列在表2的结果显示聚(丙烯酸)涂层可大幅减低镜片上的细菌粘附，该镜片可湿润化。
           表2
    镜片     未涂覆     涂覆   降低％
    实施例1  17.7×106CFU  0.20×106CFU     99％
    实施例8  3.54×106CFU  0.051×106CFU     99％
                 实施例12
将制备1的镜片浸泡在含1.5重量％聚(丙烯酸)(分子量100,000)的31.3克经硼酸盐缓冲的盐水溶液中，加入0.62克EDC并将混合物在室温下搅拌1小时，然后用新鲜的盐水溶液冲洗镜片五次。
                 实施例13
将从制备2的镜片浸泡在46.46克经硼酸盐缓冲的盐水溶液中，加入1.95克聚(丙烯酸)(分子量150,000)的35重量％水溶液，加入0.09克EDC并将混合物在室温下搅拌5分钟，然后用新鲜的盐水溶液冲洗镜片4次，所得的镜片可以湿润化。

Claims (10)

1.一种装置，其中含有生物医学装置，在该生物医学装置的至少一个表面上含羟基、胺基或其混合基，借助于有效偶合量的至少一种偶合剂在该表面上偶合有效涂覆量的羧基官能化聚合物。
2.根据权利要求1的装置，其中该羧基官能化聚合物为聚(丙烯酸)、聚(甲基丙烯酸)、聚(马来酸)、聚(衣康酸)，及(甲基)丙烯酸或丙烯酸、丙烯酸、马来酸、或衣康酸与任何反应性乙烯基单体的嵌段或无规共聚物或其混合物。
3.根据权利要求1的装置，其中该偶合剂是选自碳化二亚胺类、N，N′-羰基二咪唑、磷酰氯、四氯化钛、磺酰氯氟、氯磺酰基异氰酸酯、碘化磷、三丁胺的吡啶盐、二氯磷酸苯酯、多磷酸酯、氯硅烷类、三丁磷与异氰酸苯酯的混合物、氯甲酸烷基酯与三乙胺的混合物、2-氯-1，3，5-三硝基苯与吡啶的混合物、甲基磺酰氯与二乙胺的混合物、及三苯基膦、四氯化碳与三乙胺的混合物。
4.一种隐形眼镜，其至少一个表面含有选自硅酮弹性体、水凝胶、或含硅酮水凝胶的聚合物，该聚合物含有选自羟基、胺基或其混合基的官能基，该表面含有借助于有效偶合量的至少一种偶合剂偶合在其上面的有效涂覆量的羧基官能化聚合物，该偶合剂是选自碳化二亚胺类、N，N′-羰基二咪唑、磷酰氯、四氯化钛、磺酰氯氟、氯磺酰基异氰酸酯、碘化磷、三丁胺的吡啶盐、二氯磷酸苯酯、多磷酸酯、氯硅烷类、三丁磷与异氰酸苯酯的混合物、氯甲酸烷基酯与三乙胺的混合物、2-氯-1，3，5-三硝基苯与吡啶的混合物、甲基磺酰氯与二乙胺的混合物、及三苯基膦、四氯化碳与三乙胺的混合物，该羧基官能化聚合物是选自聚(丙烯酸)、聚(甲基丙烯酸)、聚(马来酸)、聚(衣康酸)，及(甲基)丙烯酸或丙烯酸、丙烯酸、马来酸、或衣康酸与任何反应性乙烯基单体的嵌段或无规共聚物或其混合物。
5.一种隐形眼镜，其至少一个表面含选自硅酮弹性体、水凝胶、和含硅酮水凝胶的聚合物，该聚合物含羟基、胺基或其混合基的官能基，至少一个表面含有借助于有效偶合量的碳化二亚胺偶合剂偶合在其上面的有效涂覆量的聚(丙烯酸)。
6一种生产生物医学装置的方法，其步骤包括使该生物医学装置的至少一个表面与有效涂覆量的至少一种羧基官能化亲水性聚合物及有效偶合量的至少一种偶合剂接触。
7.根据权利要求6的方法，其中该生物医学装置为隐形眼镜。
8.根据权利要求6的方法，其中该羧基官能化聚合物为聚(丙烯酸)、聚(甲基丙烯酸)、聚(马来酸)、聚(衣康酸)，及(甲基)丙烯酸或丙烯酸、丙烯酸、马来酸、或衣康酸与任何反应性乙烯基单体的嵌段或无规共聚物或其混合物。
9.根据权利要求6的方法，其中该羧基官能化聚合物为聚(丙烯酸)。
10.根据权利要求6的方法，其中该偶合剂是选自包括碳化二亚胺类、N，N′-羰基二咪唑、磷酰氯、四氯化钛、磺酰氯氟、异氰酸氯磺酰基酯、碘化磷、三丁胺的吡啶盐、二氯磷酸苯酯、多磷酸酯、氯硅烷类、三丁磷与异氰酸苯酯的混合物、氯甲酸烷基酯与三乙胺的混合物、2-氯-1，3，5-三硝基苯与吡啶的混合物、甲基磺酰氯与二乙胺的混合物、及三苯基膦、四氯化碳与三乙胺的混合物。
CNB991084497A 1998-06-11 1999-06-11 具有亲水性涂层的生物医学装置 Expired - Fee Related CN1167741C (zh)

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EP0963761B1 (en) 2003-10-29
CN1167741C (zh) 2004-09-22
KR100642970B1 (ko) 2006-11-13
US6087415A (en) 2000-07-11
BR9902243A (pt) 2000-09-26
AR018653A1 (es) 2001-11-28
DE69912352D1 (de) 2003-12-04
US6838491B1 (en) 2005-01-04
SG87032A1 (en) 2002-03-19
US6534559B1 (en) 2003-03-18
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