CN101516926B - 可固化组合物及由其形成的抗生物膜涂层 - Google Patents
可固化组合物及由其形成的抗生物膜涂层 Download PDFInfo
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- CN101516926B CN101516926B CN2007800341343A CN200780034134A CN101516926B CN 101516926 B CN101516926 B CN 101516926B CN 2007800341343 A CN2007800341343 A CN 2007800341343A CN 200780034134 A CN200780034134 A CN 200780034134A CN 101516926 B CN101516926 B CN 101516926B
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Abstract
本发明提供一种用于阻滞生物膜形成的可固化组合物。本发明还涉及包含所述可固化组合物的涂层。所述可固化组合物包含:聚合物,所述聚合物衍生自:具有长链脂族侧基的烯键式不饱和单元;具有聚(氧化烯)侧基的烯键式不饱和单元;以及具有基底反应性侧基的烯键式不饱和单元;以及交联剂。
Description
背景技术
生物膜是嵌入胞外聚合物(通常为多糖)和其它大分子的高度水合基质内的微生物聚集体。生物膜可含有单个或多个微生物物种并且容易附着至诸如医疗器械(包括导管)、土壤、管道、牙齿、粘膜和热交换器之类的各种基底。在某些环境中,定殖的微生物既能够以生物膜的(固着的)形式生长又能够以自由生活的(浮游的)形式生长,并且与生物膜相关的细胞可以1000-10,000∶1的比例在数量上超过相同种类的浮游细胞。尽管浮游细胞的生长可通过抗菌处理或灭菌处理来控制,但生物膜本身可能难以控制处理,实际上提供了细胞的储藏所,这可能会导致处理后定殖、感染和/或生物膜生长的复发。
在许多不同的领域中,防止微生物定殖和根除与生物膜相关的微生物是重要的,并且常常难以解决的问题。与对杀生物剂(例如,抗生素)相对敏感的浮游生物不同,与生物膜相关的微生物常常对许多抗菌剂具有极高的抗性。在一项研究中,与生物膜相关的细菌能够在20倍于有效除去生长于浮游培养物中的相同种类细菌的浓度的抗生素浓度下存活(Nickel,1985)。已知当生物体与生物膜分离并且随后在浮游培养基中生长时,它们会丧失许多与生物膜前体(progenitor)相关的特征,尤其是它们对抗菌剂处理的抗性。在生物膜中,多糖包被基质是一种保护性机制,其提供了抵抗宿主防御机制(例如抗体和吞噬细胞)以及某些抗菌剂的屏障。生物膜的抗菌剂抗性的其它可能原因包括:微生物中许多微生物处于休眠生长状态,显著改变了的基因和蛋白表达谱(与浮游细胞比较而言),以及“耐药株”(以随机方式产生抗菌剂抗性的微生物亚群)的存在。
尽管本项领域中已知许多组合物可用于处理基底以赋予它们对生 物膜形成的抗性,但仍继续希望提供进一步改良的用于处理基底,特别是聚合物表面、陶瓷、玻璃和石料的组合物,以便赋予它们进一步的生物膜抗性,并且更容易清洗。
发明内容
本发明提供了一种用于阻滞生物膜形成或增强已形成的生物膜的释放的可固化组合物。该可固化组合物包含:
a)聚合物,其衍生自:具有长链脂族侧基的烯键式不饱和单体单元;具有聚(氧化烯)侧基的烯键式不饱和单体单元;以及具有基底反应性侧基的烯键式不饱和单体单元;以及
b)交联剂。
在另一个实施例中,本发明包含含可固化组合物和溶剂的涂层组合物,由此将该涂层组合物施加至基底以赋予基底抗生物膜涂层。在另一个实施例中,本发明还提供了用本发明的涂层组合物涂布基底,特别是硬质基底以提供给基底抗生物膜涂层的方法。多种涂布方法可用于施加本发明的组合物,例如刷涂法、喷涂法、浸涂法、辊涂法、刮涂法等。基底上获得的涂层可在室温下或在40至300℃的高温下固化。在一些实施例中,可在室温或高温下利用催化剂来实现固化。
在此所用的术语“(甲基)丙烯酰基”包括丙烯酰基和甲基丙烯酰基/化合物两者,所述化合物包括丙烯酸和甲基丙烯酸的酯、硫酯和酰胺。在至少一些实施例中,丙烯酸酯基团是优选的。
“烯键式不饱和”表示化合物或组分具有可自由基聚合的C=C基团,例如乙烯基或(甲基)丙烯酰基团。
本文通过端点详述的数值范围包括该范围内包容的所有数字(例如,1到5包括1、1.5、2、2.75、3、3.80、4和5)。
如本说明书以及所附权利要求中所使用的,单数形式“一种”、“一个”和“该”也包括复数指代,除非上下文另外清楚地指明。因此,例如,包含“该化合物”的组合物这一表达方式包括两种或更多种化合物的混合物。另外,术语“或”通常以“和/或”的意义使用,除非上下文另外清楚地指明。
除非另外指明,否则本说明书和权利要求中所用的所有表示成分的量、特性(例如表面能、接触角)的量度等的数字在所有情况下均应理解为被术语“约”所修饰。因此,除非有相反的指示,否则在说明书和所附权利要求中列出的数字参数为近似值,该近似值的改变可取决于通过本领域的技术人员利用本发明的教导内容而获得的所需特性。在最低限度上,并且无意于将等同原则的应用受制于权利要求的范围,每个数字参数应至少按照所报告的有效数字之数并且通过应用普通的舍入技术来理解。虽然在本发明的广泛范围内设定的数字范围和参数为近似值,但具体例子中设定的数值会尽可能准确地报告。然而,任何数值都固有地含有一定的误差,并且这些误差是由它们各自的试验测定中所存在的标准偏差必然引起的。
附图说明
图1示出使用甲基丙烯酸月桂酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在该测试中所使用的细菌是嗜水气单胞菌(Aeromonas hydrophilia)。
图2示出使用甲基丙烯酸月桂酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在该测试中所使用的细菌是表皮葡萄球菌(Staphylococcus epidermidis)。
图3示出使用甲基丙烯酸硬脂基酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在该测试中所使用的细菌是表皮葡萄球菌。
图4是使用甲基丙烯酸月桂酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在这个测试中所使用的细菌是变形链 球菌(Streptococcus mutans)。
图5示出使用甲基丙烯酸硬脂基酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在该测试中所使用的细菌是变形链球菌。
图6示出使用甲基丙烯酸异癸酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在该测试中所使用的细菌是表皮葡萄球菌。
图7示出使用甲基丙烯酸正癸酯作为具有烷基链的单体,在带涂层的表面上保留的生物膜的数据。在该测试中所使用的细菌是表皮葡萄球菌。
具体实施方式
本发明提供了一种可固化组合物,该可固化组合物包含:
a)聚合物,其衍生自:具有长链脂族侧基的烯键式不饱和单体单元;具有聚(氧化烯)侧基的烯键式不饱和单体单元;以及具有基底反应性侧基的烯键式不饱和单体单元;以及
b)交联剂。
更具体地讲,本发明的第一组分聚合物包含:
10重量%至70重量%,优选15重量%至40重量%的具有长链脂族侧基的烯键式不饱和单元;
10重量%至80重量%,优选40重量%至75重量%的具有聚(氧化烯)侧基的烯键式不饱和单元;
1重量%至20重量%,优选5重量%至15重量%的具有[基底反应性]侧基的烯键式不饱和单元;和
0重量%至20重量%,优选0重量%至10重量%的其它单体。
选择“基底反应性官能团”以使得它们与所选择的基底表面的官能团形成离子键或共价键。优选的是,选择“基底反应性官能团”以使得与基底形成的键是不可水解的;即,在使用条件下基本上不会水 解。这些限制将不排除硅烷官能团的使用,在使用硅烷官能团的情况中与硅质基底表面形成的硅氧烷键被认为是不断地水解和重新形成。
还选择具有与第一组分聚合物的基底反应性官能团侧基共反应(即与之形成共价键)的官能团的交联剂。可选的“其它单体”缺少反应性官能团并且将其加入用以改变第一组分聚合物的物理性质。
具有长链脂族基团的单体具有如下通式:
R1-Q-Rh(I),其中
R1是具有通式H2C=C(R11)-的烯键式不饱和可聚合基团,其中R3是H或C1-C4烷基,优选R11是H或甲基。
Q是有机连接基团,其可包括可以是饱和的或不饱和的直链、支链或环状结构。优选地,每个二价Q基团独立地是可任选包括杂原子和/或官能团的直链基团。实例包括含有约2个至约16个碳原子(优选约3个至约个碳原子)的被一个或多个杂原子(如氧、氮或硫)、官能团(如羰基、酰氨基或亚磺酰氨基)或这两者取代的二价亚烷基、亚芳基或其混合物。
Q的实例包括下列结构,其中每个r独立地是从1到约10的整数,R5是氢、芳基或1至约4个碳原子的烷基。因此,所描绘的结构是非定向的。
应当理解,关于R1和Q基团,合在一起的R1-Q可包含乙烯基、烯丙基、乙烯氧基、烯丙氧基和(甲基)丙烯酰基。优选地,R1-Q包含(甲基)丙烯酰基。
Rh是长链脂族基团;即,具有8至75个碳原子,优选10至50,更优选10至24个碳原子的环状或无环的(或其任意组合)单价饱和脂族基团。优选地,Rh是结构为-CnH2n+1的直链单价烷基,其中n是8至75,优选10至24个碳原子。化学式I表示的化合物可选自长链(甲基)丙烯酸烷基酯和硫酯、长链烷基乙烯基醚、长链乙烯基酯和长链烷基(甲基)丙烯酰胺。
本发明的可固化组合物的单体组分包含一个或多个单官能聚(环氧烷)单体。这些单体包含一个末端可聚合的烯键式不饱和基团(如仅一个(甲基)丙烯酰基、乙烯基、烯丙基或烯丙氧基)、聚(环氧烷)部分(例如先前所描述的)和第二不可自由基聚合的末端端基,例如OH、(C1-C4)烷氧基、芳氧基(如苯氧基)或(C1-C4)烷芳氧基。这些基团可以是直链的或支链的。
聚(环氧烷)部分具有如下通式:
-(CH(R2)-CH2-O-)m-(CH2-CH2-O-)n-,其中m可以是0,n至少是5并且n与m的摩尔比(n∶m)大于2∶1,优选大于3∶1;R2是(C1-C4)烷基。-CH(R2)-CH2-O-部分和-CH2-CH2-O-部分的结构分布可以是无规的或是嵌段的。优选地,m+n至少为5,并且更优选至少为20。优选地,m+n小于500,并且更优选小于150。应当理解,m和n可以是非整数,因为聚(环氧烷)部分通常是不同量或数目的m和n个单元的混合物。
优选单官能聚(环氧烷)单体具有如下化学式:
R1-Q-(CH(R2)-CH2-O-)m-(CH2-CH2-O-)n-R3 (II)
其中
R1是如先前针对化学式I所述的烯键式不饱和可聚合基团,
R2是(C1-C4)烷基,
R3是H或R2或芳基或其组合,
Q是二价连接基团,例如先前针对化学式I所述的,
n至少为5,m可为0,n+m至少为5,并且优选至少20,并且n∶m的摩尔比至少为2∶1(优选至少3∶1)。
合适的单官能聚(环氧烷)单体的实例包括聚(环氧乙烷)(甲基)丙烯酸酯、聚(环氧乙烷-环氧丙烷)(甲基)丙烯酸酯及其组合。这样的单体通常包括非反应性端基(以进行自由基聚合)例如(C1-C4)烷基、芳基(如苯基)、(C1-C4)烷芳基、芳基(C1-C4)或羟基。这些基团可以是直链的或支链的。这些单体可以具有宽泛的分子量范围并且可从以下来源商购获得:例如宾夕法尼亚州埃克斯顿(Exton,PA)的沙多玛公司(Sartomer Company);日本东京中村新化学株式会社(ShinnakamuraChemical Co.,Ltd.,Tokyo,Japan);威斯康星州密尔沃基市的奥尔德里奇公司(Aldrich,Milwaukee,WI);以及日本大阪的大阪有机化工株式会社(Osaka Organic Chemical Ind.,Ltd.,Osaka,Japan)。
官能单体是结构为R1-Q-X(III)的化合物,其中:
R1-Q-是烯键式不饱和可聚合基团,包括乙烯基、烯丙基、乙烯氧基、烯丙氧基、(甲基)丙烯酰氨基和(甲基)丙烯酰基,如先前针对化学式I所述的,
Q是二价连接基团,例如上文关于化学式I所述的,并且
X是表面反应性官能团,其能够与其上设置有可固化组合物的基底(如金属表面、玻璃、玻璃布或可与X形成共价键或离子键的任何表面)键合,并且还能够与交联剂键合。
优选地,X是硫醇基(-SH)、单磷酸根基、膦酸根基或膦酸基(-P(O)(OH)2)、异羟肟酸基(-C(O)NHOH)、羧酸基(-C(O)OH)、异腈基、异氰酸根基、胺基、甲硅烷基或二硫基(-S-S-)。更优选地,X是硫醇基、单磷酸根基、膦酸根基、羧酸基、甲硅烷基、钛酸根基或锆酸根基。
对于氧化铝表面,优选X包括膦酸基(-P(O)(OH)2)、异羟肟酸基 (-C(O)NHOH)或羧酸基(-C(O)OH)。对于氧化铁或钢表面,优选X包括异羟肟酸基(-C(O)NHOH)。对于氧化铜,优选X包括异羟肟酸基(-C(O)NHOH)、硫醇基(-SH)、单磷酸根基、膦酸根基或膦酸基。
对于氧化硅、玻璃或其它硅质表面,优选X包括化学式-Si(Y)x(R7)3-x表示的甲硅烷基,其中Y是可水解基团(包括卤素、C1-C4烷氧基或C1-C4酰氧基),R7为单价烷基或芳基,x为1、2或3。对于金、铜和银,优选X为硫醇基(-SH)或二硫基(-S-S-)。
诸如聚氨酯之类的许多聚合物基底在它们的表面上具有羟基或羧酸基,并且可据此选择X。如果聚合物表面不含官能团,则可以通过本领域已知的技术使这些官能团在表面上生成。例如,含氧气氛中的电晕放电将会在表面上生成羟基和羧基。等离子处理将在聚合物表面上产生任意的多种反应基团。随后可以选择基底反应性侧基“X”来与该表面反应性基团反应。
第一组分聚合物还可包含先前未描述的其它单体。对可用于制备该聚合物的“其它单体”进行选择使得最终交联材料具有适合于其应用的性质。例如,“其它单体”可用于增加抗拉强度或其它机械性能,或用于控制聚合物的Tg。“其它单体”的代表性实例包括具有至少一个烯键式不饱和可聚合基团的可自由基聚合的单体,该烯键式不饱和可聚合基团可与上述单体共聚,并且包括乙烯基单体,例如醋酸乙烯酯、苯乙烯、烯丙基醚、马来酸酐、烷基乙烯基醚,“极性单体”和(甲基)丙烯酸低级烷基酯。当存在时,聚合物通常包含小于20重量%(如1重量%至10重量%)的这类单体单元。
可用于本发明的(甲基)丙烯酸烷基酯单体包括含有C1-C7烷基的烷基酯的直链、环状和支链异构体。可用的(甲基)丙烯酸烷基酯的具体实例包括:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸-2-丁酯、(甲基)丙烯酸异戊酯、(甲基)丙烯酸正己酯 和(甲基)丙烯酸庚酯。
第一组分聚合物还可包含“极性单体”。在此所用的“极性单体”为具有至少1重量%,优选至少5重量%的水混溶性(水在单体中)而未达到浊点的那些可聚合单体。极性单体可用于增加固化的组合物的吸收性和/或改进其机械性能(如抗拉强度)。优选的极性单体也可为所得聚合物提供顺应性。极性单体可含有官能团,但这些官能团通常不与所选基底、表面反应性单体或交联剂反应。
合适的极性单体的实例包括N-乙烯基己内酰胺、N-乙烯基乙酰胺、N-乙烯基吡咯烷酮、丙烯腈、丙烯酸四氢糠基酯、丙烯酰胺、单-或双-N-烷基取代的丙烯酰胺、丙烯酸β-羧乙基酯、[2-(甲基)(丙烯酰氧基)乙基]三甲基氯化铵、[2-(甲基)(丙烯酰氧基)乙基]三甲基铵硫酸甲酯、[2-(甲基)(丙烯酰氧基)乙基]二甲基十八烷基氯化铵及其组合。优选的极性单体包括N-乙烯基吡咯烷酮、N-乙烯基乙酰胺和也为季铵盐的单体以及它们的混合物等。可用的含有季铵的极性单体在U.S.5,374,501和U.S.5,712,027(Ali等人)中公开,将这些专利以引用方式并入本文中。
该聚合物组分可以通过用常规聚合方法聚合上述单体组分而产生。可使用的典型聚合方法包括热聚合法和/或光化学聚合法以及本体聚合法和溶液聚合法。如本领域中已知的那样,可以通过使用链转移剂和链阻滞剂控制分子量,例如诸如十二烷基硫醇、巯基乙酸异辛酯和α-甲基苯乙烯之类的烷基硫醇。
在一种代表性的溶液聚合方法中,在存在溶剂和聚合引发剂的情况下伴随搅拌地将单体组分合并,可任选进行加热。溶剂的实例是甲醇、乙醇、异丙醇、丙酮、甲基乙基酮、甲基异丁基酮、乙酸甲酯、乙酸乙酯、庚烷、甲苯、二甲苯和乙二醇烷基醚。这些溶剂可单独使用或作为其混合物使用。优选地,在基底反应性官能团X为硅烷的情况下,溶剂组分含有能够与所有单体形成溶液的醇溶剂。
适用于这种聚合反应的引发剂包括(例如)热引发剂和光引发剂。引发剂通常以每100重量份单体0.001至5重量份的水平使用。可用的热引发剂包括偶氮化合物和过氧化物。可用的偶氮化合物的实例包括:2,2′-偶氮二(2,4-二甲基戊腈)(VazoTM52,可从杜邦·德内穆尔公司(E.I.duPont de Nemours & Co.)商购获得);2,2′-偶氮二(异丁腈)(VazoTM64,可从杜邦·德内穆尔公司(E.I.duPont de Nemours & Co.)商购获得);2,2’-偶氮二(2-甲基丁腈),(VazoTM67,可从杜邦商购);1,1’-偶氮二(氰基环己烷),(VazoTM 88,可从杜邦商购获得);1,1′-偶氮二(1-环己烷-1-腈),(V-40,可从和光纯药工业株式会社(Wako PureChemical Industries,Ltd.)商购获得);以及,2,2′-偶氮二异丁酸二甲酯,(V-601TM,可从Wako商购获得)。可用的过氧化物的实例包括:过氧化苯甲酰;二叔戊基过氧化物、过氧苯甲酸叔丁酯、2,5-二甲基-2,5双(叔丁过氧基)己烷、2,5-二甲基-2,5-双(叔丁过氧基)己炔-3、过氧化月桂酰和叔丁基过氧化特戊酸酯。可用的有机氢过氧化物包括(但不限于)诸如叔戊基过氧化氢和叔丁基过氧化氢之类的化合物。
可用的光引发剂包括安息香醚,例如安息香甲基醚和安息香丁基醚;苯乙酮衍生物,例如2,2-二甲氧基-2-苯基-苯乙酮和2,2-二乙氧基苯乙酮;以及酰基膦氧化物衍生物和酰基膦酸酯衍生物,例如二苯基-2,4,6-三甲基苯甲酰膦氧化物、异丙氧基(苯基)-2,4,6-三甲基苯甲酰膦氧化物和二甲基特戊酰膦酸酯。这些化合物中,2,2-二甲氧基-2-苯基-苯乙酮是优选的。
在典型的光聚合方法中,在光聚合引发剂(即光引发剂)存在的情况下,用紫外(UV)线照射单体组分的混合物。市售的光引发剂包括:购自纽约州塔里敦的汽巴特种化学品公司(Ciba Speciality ChemicalCorp.,Tarrytown,NY)的IRGACURE并且包括1-羟基环己基苯基酮(IRGACURE 184)、2,2-二甲氧基-1,2-二苯基-1-乙酮(IRGACURE651)、双(2,4,6-三甲基苯甲酰基)苯基膦氧化物(IRGACURE 819)、 1-[4-(2-羟乙氧基)苯基]-2-羟基-2-甲基-1丙烷-1-酮(IRGACURE 2959)、2-苄基-2-二甲氨基-1-(4-吗啉代苯基)丁酮(IRGACURE 369)、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉基-1-丙酮(IRGACURE 907)以及2-羟基-2-甲基-1-苯基-1-丙酮(IRGACURE 1173)。特别优选的光引发剂是IRGACURE 819和2959。
在聚合本文所述的单体时可使用链转移剂以控制所得聚合物的分子量。合适的链转移剂包括卤代烃(如四溴化碳)和硫化合物(如月桂基硫醇、丁硫醇、乙硫醇以及2-巯基乙基醚、巯基乙酸异辛酯、叔月桂基硫醇、3-巯基-1,2-丙二醇)。当硅质表面是所选择的基底时,优选的链转移剂是巯丙基三甲氧基硅烷。链转移剂的量取决于所希望的聚合物的分子量和链转移剂的类型。基于单体的总重量,链转移剂通常以约0.1重量份至约10重量份;优选0.1重量份至约8重量份;并且更优选约0.5重量份至约6重量份的量使用。
可固化组合物还包含由化学式R8(Z)m表示的交联剂,其中R8可以是化合价为m的聚合或非聚合有机基团,并且Z是与官能单体的官能团共反应的反应性官能团。关于化合物R8(Z)m,m至少为二。多官能化合物的多个-Z基团可相同或不同。
应当理解,在上文描述的第一组分聚合物和交联组分的情形中,选择具有反应性官能团(由化学式III表示的单体的“X”基团)的烯键式不饱和单体以使得第一组分聚合物和交联组分互相共反应,使得第一组分聚合物具有官能团侧基(与第二组分交联剂的官能团侧基(“Z”基团)共反应的“X”基团)。反应性官能团和共反应官能团通过在亲电子官能团和亲核官能团对之间形成连接基团来形成第一组分与第二组分之间的交联,并且可包括通常被称为置换、缩合和加成反应的反应,而不是烯属不饱和基团的聚合。
示例性的组合包括与硅烷-、异氰酸根-及酐-官能团反应的羟基或 氨基官能团和与氮丙啶或环氧基团反应的羧基。可选择环氧树脂来与磷酸酯和膦酸酯反应。巯基官能单体可与异氰酸根和环氧基团反应。在选择硅质表面的情况下,X和Z两者优选为由化学式-Si(Y)x(R7)3-x表示的硅烷基,其中Y是可水解基团(包括卤素、C1-C4烷氧基或C1-C4酰氧基),R7为单价的烷基或芳基,x为1、2或3。
有机部分R8具有高达20,000的分子量,优选选自单价和多价的烃基(即,具有1至30个碳原子和任选零至四个链中杂原子氧、氮或硫的脂族和芳基化合物)、聚烯烃、聚氧化烯、聚酯、聚烯烃、聚丙烯酸酯或硅氧烷主链并且可在涂层溶剂中溶解。
在一个实施例中,R8包含具有1至30个碳原子的非聚合脂族部分、脂环族部分、芳族部分或烷基取代的芳族部分。在另一个实施例中,R8包含具有反应性-Z侧基或末端反应性-Z基团的聚氧化烯、聚酯、聚烯烃、聚丙烯酸酯或聚硅氧烷聚合物。可用的聚合物包括(例如)羟基、硫醇或氨基封端的聚乙烯或聚丙烯,羟基、硫醇或氨基封端的聚(环氧烷)和聚丙烯酸酯,其具有反应性官能团侧基,例如丙烯酸羟乙酯聚合物和共聚物。
可用的由化学式R8(Z)m表示的醇包括脂族多元醇和芳族多元醇。可用于本发明的多元醇包括具有1至30个碳原子、至少两个羟基的脂族多元醇或芳族多元醇。可用的多元醇的实例包括乙二醇、丙二醇、丁二醇、1,3-戊二醇、2,2-氧代二乙醇、己二醇、聚(己二酸戊二醇酯)(poly(pentyleneadipate glycol))、聚(四亚甲基醚乙二醇)、聚(乙二醇)、聚(己内酯二醇)、聚(1,2-亚丁基氧乙二醇)、三羟甲基乙烷、三羟甲基丙烷、三羟甲基氨基甲烷、乙二醇、2-丁烯-1,4-二醇、季戊四醇、二季戊四醇和三季戊四醇。术语“多元醇”还包括上文所述多元醇的衍生物,例如多元醇与双或聚异氰酸酯或者双或聚羧酸的反应产物,多元醇与-NCO或-COOH的摩尔比为1比1。
可用的由化学式R8(Z)m表示的胺包括脂族聚胺和芳族聚胺。代表性的可用的二胺或聚胺是4,4′-亚甲基二苯胺、3,9-双(3-氨丙基)-2,4,8,10-四氧杂螺[5,5]十一烷,以及聚氧乙二胺。许多二胺和聚胺(例如刚提到的那些)是可商购获得的,例如,可得自德克萨斯州休斯敦的亨茨曼化工公司(Huntsman Chemical,Houston,TX)的那些。最优选的二胺或聚胺包括脂族二胺或脂族二胺或聚胺,并且更具体地讲为具有两个伯氨基的化合物,例如乙二胺、环己烷二胺、十二烷二胺等。
可用的由化学式R8(Z)m表示的硫醇包括脂族和多官能硫醇。可用的烷基硫醇包括2-巯基乙醇、3-巯基-1,2-丙二醇、4-巯基丁醇、巯基十一醇、2-巯基乙胺、2,3-二巯基丙醇、3-巯丙基三甲氧基硅烷、2-氨基-3-巯基丙酸以及季戊四醇四硫代甘醇酸酯(pentaerythritoltetrathioglycolate)。可用的可溶性高分子量的硫醇包括:聚乙二醇二(2-巯基乙酸酯)、由Morton Thiokol公司(特伦顿,新泽西州(Trenton,N.J.))供应的LP-3TM树脂、由Products Research & Chemical Corp.(格伦代尔,加利福尼亚(Glendale,Calif.))供应的Permapol P3TM树脂,以及诸如2-巯基乙胺与己内酰胺的加成物之类的化合物。
合适的多异氰酸酯包括含有至少两个自由异氰酸酯基的有机化合物。优选使用由化学式R9(NCO)2表示的二异氰酸酯,其中R9表示具有4至20个碳原子的脂族烃基、具有6至20个碳原子的脂环族烃基、具有6至20个碳原子的芳族烃基或具有7至20个碳原子的芳脂族烃基。
二异氰酸酯的实例包括四亚甲基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、十二亚甲基二异氰酸酯、1,4-二异氰酸根合环己烷(diisocyanatocy clohexane)、1-异氰酸根-3,3,5-三甲基-5-异氰酸根合甲基环己烷(IPDI)、4,4′二异氰酸根-二环己基甲烷(1-112MDI)、4,4′-二异氰酸根-2,2-二环己基-丙烷、1,4-二异氰酸根合苯、2,4-二异氰酸根合甲苯(TDI)、2,6二异氰酸根合甲苯、4,4′-二异氰酸根合二苯 甲烷(MDI)、间-和对-苯二甲基二异氰酸酯、α、α、α’、α’-四甲基-间-和对-苯二甲基二异氰酸酯以及这些化合物的混合物。合适的多异氰酸酯还包括三异氰酸酯例如1,3,5三异氰酸根合环己烷-s-三酮(1,3,5triisocyanatocyclohexane-s-trione)、异氰脲酸酯及HDI和H12MDI的缩二脲衍生物以及聚合芳族异氰酸酯,例如购自密歇根州米德兰的道氏化学公司(Dow Chemical,Dow Chemical,Midland,MI)的PAPI tm材料。
对于硅质基底,具有至少两个自由甲硅烷基的化合物是优选的。合适的硅烷交联剂通常具有化学式:
R10(-Si(Y)x(R7)3-x)p,其中Y是可水解基团(包括卤素、C1-C4烷氧基或C1-C4酰氧基),R7是单价的烷基或芳基,x是1、2或3,p至少是2,R10是任选被链中氧或氮原子取代的多价有机基团,优选为3至10个碳原子的二价亚烷基基团。
属于这个类别的硅烷交联剂(例如)可从田纳西州莫里森市(Morristown,N.J)的Scotia,N.Y,Allied-Signal公司的Silar实验室和Lisle,Ill的OSI Chemicals商购获得。具有仲氨基的烷氧基硅烷,例如,双-(三甲氧基硅烷丙基)胺(购自Osi Specialties公司(Lisle,Ill)的Silquest A-1170)是特别优选的,因为含有硅烷的胺是自催化性的。
现存的聚合物可在任选存在催化剂的情况下与交联剂和通过加热方法交联的组合物合并以实现缩合反应。具体的催化剂的选择取决于官能团R8(Z)m和由化学式III表示的基底-反应性官能团X。催化剂可以是酸催化剂、碱催化剂或含有金属的催化剂。一般来讲,基于可固化组合物的总重量,催化剂或催化剂混合物以约0.01重量%-5重量%的量,并且更优选以约0.1重量%至2重量%的量存在于该组合物中。
在第一聚合物和/或交联剂具有硅烷官能团(化学式II,X为硅烷)的情况下,用于硅烷官能团的合适的固化催化剂包括烷基锡化合物(例 如,可作为“T系列催化剂”购自宾夕法尼亚州阿伦敦(Allentown,Pa.)的空气化工产品公司(Air Products and Chemicals,Inc.)的二丁基二月桂酸锡、二丁基二乙酸锡以及二丁基二异辛酸锡)和烷基钛酸酯(例如,可以商标名“TYZOR”从杜邦商购获得的四异丁基正钛酸酯(tetraisobutylorthotitanate)、四乙酰丙酮络钛(titanium acetylacetonate)和乙酰乙酸酯钛酸酯(acetoacetic ester titanate))。但是,一般来讲,优选选择不需要使用固化催化剂的硅烷交联剂以避免减短贮存期限和不利地影响涂层组合物的物理性质。
可用于硅烷官能团的其它催化剂包括酸、酐及其低级烷基铵盐,其包括(但不限于)三氯乙酸、氰乙酸、丙二酸、硝基乙酸、二氯乙酸、二氟乙酸、三氯乙酸酐、二氯乙酸酐、二氟乙酸酐、三氯乙酸三乙铵酯(triethylammonium trichloroacetate)、三氯乙酸三甲铵酯(trimethylammonium trichloroacetate)以及它们的混合物。
本发明的涂层组合物可包括有效量的杀生物剂来防止或阻滞微生物的生长。本发明并不限于选择任何特定的杀生物剂,任何已知的杀生物剂都可包含于本发明的组合物中,例如防霉剂、抗菌剂、防腐药、消毒剂、卫生洗涤剂、杀菌剂、灭藻剂、防污剂、防腐剂以及前述试剂的组合等。预期在本发明的广泛教导内容内,将根据需要选择杀生物剂以在湿润条件下或暴露于不同程度的湿气时保护特定基底防止特定类型的微生物生长。此外,包含于本发明组合物中的杀生物剂可包含一种或多种在抗微生物上有效的物质。
所选的杀生物剂或杀生物剂的组合将与组合物的其它组分相容,并且优选为有效对抗常见微生物(例如常见于湿润、湿或潮湿环境中的那些微生物)的杀生物剂。据信对包含于本发明组合物中的合适杀生物剂的选择是在本领域所实践的那些技术范围内。由于需要杀生物剂与组合物中的其它组分在化学上相容,合适类型的杀生物剂包括:阳离子季铵化合物、有机硫化合物例如砜和硫氰酸酯;异噻唑啉酮; 苯酚和受取代的苯酚;二嗪;三嗪,有机锡化合物;酰胺例如2,2-二溴-3-氰基丙酰胺以及碘代苯甲酰苯胺;氨基甲酸酯,包括(但不限于)硫代氨基甲酸酯、苯并咪唑基氨基甲酸酯和二硫代氨基甲酸酯;乙内酰脲,包括二甲基乙内酰脲;有机卤素;甲醇例如二氯苯基三氯乙醇;有机磷酸酯;脲,包括诸如二氟苯甲酰氯苯基脲(difluoro benzoylchlorophenylurea)之类的苯甲酰脲;拟除虫菊酯类;醌;二甲酰亚胺;胍例如乙酸十二烷基胍酯;三唑;噻二唑;以及金属性的磷酸单乙酯(metallic monoethyl phosphate)、银、铜、锡及其盐,以及前述化合物中任何化合物的有效组合。
杀生物剂可以约0.1重量%至5.0重量%,并且优选约0.1重量%至约2.0重量%的浓度范围存在于本发明的可固化或固化组合物中。当然,本发明并不限于前述浓度范围。杀生物剂的浓度可根据需要进行调整以在变化的预期使用条件下,例如在不同的湿度水平、温度条件等下维持期望的效力水平。另外,所选杀生物剂的化学性质可影响杀生物剂的期望浓度,如本领域的技术人员已知的那样。
在其上设置有涂层用以阻滞生物膜的基底可以是多种材料中的任何材料。可用的基底包括陶瓷、包括玻璃的硅质基底、金属、天然石料和人造石料、织造制品和非织造制品、包括热塑性和热固性聚合物材料在内的聚合物材料(例如聚(甲基)丙烯酸酯、聚碳酸酯、聚苯乙烯、诸如苯乙烯丙烯腈共聚物之类的苯乙烯共聚物、聚酯、聚对苯二甲酸乙二酯)、硅酮(例如在医用管材中使用的硅酮)、油漆(例如基于丙烯酸树脂的那些)、粉末涂层(例如聚氨酯或混合粉末涂层)以及木材。可用本发明的涂层组合物有效地处理多种制品以在制品上提供抗生物膜涂层。
可用本发明的可固化组合物或涂层组合物以特别有效的方式处理的许多基底包括:具有能够与根据化学式II的聚合物的X基团反应的表面官能团的基底。优选地,基底表面的这种反应性是由活性氢原子 提供。当不存在这样的活性氢原子时,可以首先将基底在含有氧的等离子体中或电晕气氛中处理以使其与化学式II的X基团反应。
如果聚合物表面并不含官能团,则可利用多种手段来在表面上生成这样的官能团。例如,含氧气氛中的电晕放电将会使表面上生成羟基和羧基。等离子处理将会使聚合物表面上产生许多反应基团。然后可以选择官能单体与该表面反应性基团反应。当然,表面处理的选择在很大程度上取决于将要用作基底的聚合物材料。
发现特别适用于将本发明的涂层施加至聚合物材料的一种方法是通过氧等离子放电来氧化聚合物表面的表面。在这之后,生成硅质(玻璃状或硅石状)表面。硅石表面可通过多种技术产生。一种可用的方法由以下步骤组成:将单体或低聚硅烷的醇溶液施加至表面,然后将其暴露于氨蒸汽。这种坚韧的多微孔的玻璃状表面随后能与本发明的硅烷改性的涂层反应,赋予本发明的涂层耐久性。可进一步参考WO2005/049757(Harvey等人)。
如果表面是全氟化表面,例如聚四氟乙烯(PTFE)聚合物表面,则可将其用溶解于氨水中的钠或溶解于四氢呋喃或其它适当溶剂中的环烷酸钠处理。这种处理使表面脱氟且得到具有羟基和羧基的表面,这个表面随后能够与上文所述的官能团中的许多官能团反应。
优选地,应该在施加本发明组合物之前清洗基底以获得最佳特性,特别是耐久性。也就是说,在涂布之前待涂布的基底表面应该基本上无有机污染。清洗技术取决于基底的类型,并且包括(例如)利用诸如丙酮或乙醇之类的有机溶剂的溶剂洗涤步骤。
金属表面常常被有机污染物层覆盖。在将本发明的涂层施加至这种表面之前,应该将它们至少通过溶剂擦拭来进行清洁。就严重的污染而言,必须将金属表面以本领域技术人员已知的方式进行蚀刻、阳 极化或处理。例如,如果钢的表面涂布有锈,则必须通过酸处理将锈蚀刻掉。一旦将金属表面暴露,就可施加涂层,允许基底反应性官能团与基底表面中的羟基或金属原子反应。
生物膜通常在基底与水接触或暴露于湿润条件的地方生长。可固化涂层阻滞这种生物膜的形成,特别是在暴露于循环水时。据信微生物不能够或很少能够附着至带涂层的表面上。而且,据信现存的生物膜能被更容易地从带涂层的表面移除。因此,可固化组合物特别适用于潮湿或湿润环境中的基底,例如医疗导管涂层、防污船舶涂层(antifouling marine coating)、用于水处理设备、热交换器和其它暖通空调设备的涂层、用于过滤介质和牙科设备、可用于口腔的装置和材料的涂层。
涂层组合物包含第一组分聚合物、交联组分和溶剂。可用的溶剂包括不会不利地影响与基底键合或交联反应的任何溶剂并且其中组分可溶解达至少1重量%。溶剂的实例为甲醇、乙醇、异丙醇、丙酮、甲基乙基酮、甲基异丁基酮、乙酸甲酯、乙酸乙酯、庚烷、甲苯、二甲苯和乙二醇烷基醚。这些溶剂可单独地使用或作为其混合物使用。如果聚合物含有硅烷官能团侧基,优选地,溶剂组分含有趋于暂时阻滞硅烷之间的反应的醇溶剂。一般来讲,水溶液不是优选的,因为聚合物组分在中性水中基本上是不溶解的;其特征在于,在中性(pH约7)水中大于0.1重量%的聚合物的混合物会产生多相组合物。
涂层组合物通常是相对稀释的溶液,含有0.1重量%至50重量%之间的固体组分,优选1重量%至25重量%之间的固体组分。应该选择溶剂、聚合物和交联组分的比例以获得具有适于施加条件的粘度的均匀混合物。例如,将要刷涂或辊涂的材料将优选具有比浸涂溶液更高的粘度。
实例
除非另外指明,否则所有的溶剂和试剂均购自美国威斯康星州密尔沃基的奥德里奇化学公司(Aldrich Chemical Company,Milwaukee,WI)。除非另外指明,否则所有百分比和量均按重量计。
聚合方法
通过下文描述的方法制备甲基丙烯酸烷基酯和_聚乙二醇单甲基丙烯酸酯单甲基醚的共聚物(PEG1000,MW=约1000)并将该反应混合物的具体组分在表1中列出。将甲苯、庚烷和乙醇的不同混合物用于将聚乙二醇单甲基丙烯酸酯甲基醚和甲基丙烯酸烷基酯单体置于溶液中。除了单体之外,该聚合混合物还包括5-10%的甲基丙烯酰氧丙基三乙氧基硅烷/三甲氧基硅烷和0.5-1%的巯丙基三甲氧基硅烷。将0.5-1%(基于单体重量)浓度的VAZO 64用作聚合引发剂。将单体溶解于溶剂或溶剂混合物中。如果单体是固体,则常常需要温和地加热聚合混合物以确保所有这些单体溶解。用于溶解单体的温度是60℃或更低。然后在添加VAZO 64TM引发剂前,将反应混合物冷却至20℃。然后将氮气鼓入该反应混合物两分钟并盖上。将反应瓶用电绝缘带来包裹并将其置于保持架(cage)中,并利用海绵防止瓶子破损。将保持架(内有反应瓶)置于Atlas Launder-o-meter(伊利诺斯州芝加哥市(Chicago,I L.)的Atlas Electric Device公司)中。在65℃进行聚合反应18小时,并在这之后,测定固体百分比。
制备带涂层的膜的表面
通过在准备好的聚碳酸酯盘表面上涂布来测试抗生物膜可固化组合物。从0.5″聚碳酸酯杆(Plastics International,Eden Prairie,MN)碾磨出该聚碳酸酯盘。该盘的标称厚度为0.15″且标称直径为0.5″。用3M公司的干湿两用砂纸(500grit Wetordry Tri-M-Ite)研磨这些盘的表面,然后用3M公司的Wetordry抛光纸进行抛光。使用YES G1000等离子处理器(可得自加利福尼亚州圣何塞市的Yield Engineering Systems公司)以500W在氧气中对该基底进行10分钟的等离子处理。之后,用滴眼管将在乙醇中固形物含量为约1%的聚(二甲氧基硅烷)(PSI-026,可 购自宾夕法尼亚州莫里斯维尔市的格莱斯特公司(Gelest,Inc.,Morrisville,PA))的涂层施加在经等离子处理的表面上。将1滴或2滴PSI-026溶液施加到该聚碳酸酯盘的每一侧面上。该溶液使盘表面完全湿润。让溶剂蒸发并且在干燥时,将该盘置于其底部填充有氢氧化铵的干燥器中持续约1/2小时。
在如表2所列出的溶剂混合物中制备可固化组合物涂层混合物。通常,涂层溶液含有被测试的共聚物(1%至2%的固体)和A1170(基于共聚物重量为20%,双(三甲氧基甲硅烷基丙基)胺,可购自宾夕法尼亚州莫里斯维尔市的格莱斯特公司(Gelest,Inc,Morrisville PA))。将该带涂层的基底在120℃下固化15小时。
测试带涂层的表面的生物膜抗性
将CDC生物膜反应器(蒙大拿州博兹曼市(Bozeman,MT)的Biosurface Technologies公司)用于评估所制备的可固化组合物抵抗生物膜形成的能力。该系统允许对以一前一后排列的多个测试基底样品(试样块)上的宏观生物膜形成进行定量。将这些样品装在反应器中,每个夹持器上一式三份。每个反应器有八个夹持器。在开始试验前,通过将水穿过反应器16至24个小时来在该组装好的反应器中洗涤样品。然后将该组装好的反应器进行高压灭菌(在121℃下15分钟),之后装入大约350mL的培养基,培养基取自装有10升超纯水中的无菌2%Bacto胰酶大豆肉汤(TSB)(马里兰州斯帕克斯市的BD公司(Becton,Dickinson and Co.,Sparks,MD))的容器。然后,用5mL TSB中的测试细菌菌株过夜培养物中的0.4mL对反应器进行接种。在搅拌(130RPM)下将该反应器培养物孵育24小时,而不让培养基从容器流过来以允许细胞附着和生长。然后将来自容器的新鲜培养基以每小时大约400mL的速率经过反应器另外24小时以便于生物膜生长,同时也进行搅拌(130RPM)。所有孵育均在37℃下进行。
这些生长条件用于表皮葡萄球菌ATCC#35984和大肠杆菌K12。 对于变形链球菌ATCC#25175,规程作如下更改:培养基为10%TSB,用1.0ml的过夜培养物进行接种,且搅拌速率为310RPM。对于嗜水气单胞菌ATCC#7966,规程作如下更改:生长培养基为具有0.1%葡萄糖的2%TSB,并且所有孵育均在室温下进行。
在孵育后,从CDC反应器中移出杆、完整的试样块样品和粘附的生物膜,并在结晶紫的饱和水溶液中染色45秒。然后用磷酸盐缓冲盐水冲洗杆和样品20至40次以移除过量的结晶紫和任何疏松粘附的细胞。从杆上移下试样块并将其置于装有4mL乙醇的15mL Falcon离心管(马萨诸塞州贝德福德市的BD生命科学公司(BD Biosciences,Bedford,MA))中,在其中通过涡旋(Vortex Genie 2,纽约波西米亚(Bohemia,NY)的Scientific Industries公司)大约10秒来洗脱结晶紫。用Genesys 6分光光度计(威斯康星州麦迪逊市热电公司(ThermoElectron Corp.,Madison,WI))测量乙醇溶液的吸光度(λ=590nm)来估计粘附至聚碳酸酯试样块的生物膜的量。所示值为一式三份的样品的平均吸光度。对于与生物膜的存在无关的也被结晶紫染色的材料(背景染色),通过如下方法定量材料着色的量:从乙醇溶液移出测试试样块,在流动水下轻轻地擦洗试样块以移除所粘附的生物膜并然后用结晶紫重新染色,并且如上文所述冲洗并洗脱到乙醇内。然后从通过使具有粘附的生物膜的试样块着色而获得的值减去这些背景吸光度。结果包括于表格3中并且在图1至图7中有说明。
表3:利用CDC反应器的生物膜保留测量结果
表2的聚合物 | 所用细菌种 | 吸光度 |
9 | 大肠杆菌 | 0.9±0.05 |
10 | “ | 1.02±0.21 |
11 | “ | 0.09 |
12 | “ | 0.24±0.01 |
13 | “ | -0.06±0.01 |
19 | “ | -0.12 |
20 | “ | 0.55±0.07 |
9 | 嗜水气单胞菌 | 参见图1 |
10 | “ | ” |
12 | “ | ” |
13 | “ | ” |
19 | “ | ” |
20 | “ | ” |
21 | “ | ” |
9 | 表皮葡萄球菌 | 参见图2 |
10 | “ | ” |
12 | “ | ” |
13 | “ | ” |
19 | “ | ” |
20 | “ | ” |
21 | “ | ” |
14 | 表皮葡萄球菌 | 参见图3 |
15 | “ | ” |
16 | “ | ” |
17 | “ | ” |
18 | “ | ” |
19 | “ | ” |
20 | “ | ” |
21 | “ | ” |
表2的聚合物 | 所用细菌种 | 吸光度 |
9 | 变形链球菌 | 参见图4 |
10 | “ | ” |
11 | “ | ” |
12 | “ | ” |
13 | “ | ” |
19 | “ | ” |
20 | “ | ” |
21 | “ | ” |
14 | 变形链球菌 | 参见图5 |
15 | “ | ” |
16 | “ | ” |
17 | “ | ” |
18 | “ | ” |
19 | “ | ” |
20 | “ | ” |
21 | “ | ” |
5 | 表皮葡萄球菌 | 参见图6 |
6 | “ | ” |
7 | “ | ” |
8 | “ | ” |
19 | “ | ” |
21 | “ | ” |
1 | 表皮葡萄球菌 | 参见图7 |
2 | “ | ” |
3 | “ | ” |
4 | “ | ” |
19 | “ | ” |
21 | “ | ” |
Claims (7)
1.一种可固化组合物,包含:
a)聚合物,其得自:具有长链脂族侧基的烯键式不饱和单体单元;具有聚(氧化烯)侧基的烯键式不饱和单体单元;和具有基底反应性侧基的烯键式不饱和单体单元;以及
b)交联剂,其具有化学式R8(Z)m,其中m至少为2,R8可以是具有化合价m的聚合有机基团或非聚合有机基团,Z是与所述聚合物的所述基底反应性侧基官能团共反应的反应性官能团。
2.根据权利要求1所述的可固化组合物,所述聚合物包含:
10重量%至70重量%的具有长链脂族侧基的烯键式不饱和单元;
10重量%至80重量%的具有聚(氧化烯)侧基的烯键式不饱和单元;
1重量%至20重量%的具有基底反应性侧基的烯键式不饱和单元;和
0重量%至20重量%的其它单体。
3.根据权利要求1所述的可固化组合物,其中具有聚(氧化烯)侧基的单体具有如下化学式:
R1-Q-(CH(R2)-CH2-O-)m-(CH2-CH2-O-)n-R3
其中,
R1是烯键式不饱和可聚合基团,
R2是(C1-C4)烷基,
R3是H或R2或芳基,或其组合,
Q是二价连接基团,
n至少为5,n+m至少为5,并且n∶m的摩尔比至少为2∶1。
4.根据权利要求1所述的可固化组合物,其中所述含有长链脂族基团的单体具有如下通式:
R1-Q-Rh,(I)
其中R1是烯键式不饱和可聚合基团,
Q是二价连接基团,并且
Rh是具有8至75个碳原子的环状或无环的单价脂族基团。
5.根据权利要求1所述的可固化组合物,其中具有基底反应性官能团的所述单体具有化学式R1-Q-X,其中
R1是烯键式不饱和可聚合基团,
Q是二价连接基团,并且
X是能够与基底键合的表面反应性官能团。
6.根据权利要求1所述的组合物,其中所述交联剂具有化学式R10(-Si(Y)x(R7)3-x)p,其中Y是可水解基团,R7是单价的烷基或芳基,x是1、2或3,p至少为2,R10是可任选被链中氧原子或氮原子取代的3至10个碳原子的多价亚烷基。
7.一种基底,具有根据权利要求1-6中任一项所述的固化的组合物的涂层。
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2006
- 2006-09-26 US US11/535,255 patent/US7585919B2/en not_active Expired - Fee Related
-
2007
- 2007-09-19 EP EP20070842789 patent/EP2069410B1/en not_active Not-in-force
- 2007-09-19 JP JP2009529366A patent/JP2010505009A/ja active Pending
- 2007-09-19 CN CN2007800341343A patent/CN101516926B/zh not_active Expired - Fee Related
- 2007-09-19 BR BRPI0718448-4A2A patent/BRPI0718448A2/pt not_active Application Discontinuation
- 2007-09-19 DE DE200760008743 patent/DE602007008743D1/de active Active
- 2007-09-19 WO PCT/US2007/078901 patent/WO2008039670A1/en active Application Filing
- 2007-09-19 AT AT07842789T patent/ATE478895T1/de not_active IP Right Cessation
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US6048953A (en) * | 1996-06-03 | 2000-04-11 | Toyo Ink Manufacturing Co., Ltd. | Curable liquid resin composition |
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US7585919B2 (en) | 2009-09-08 |
CN101516926A (zh) | 2009-08-26 |
US20080075960A1 (en) | 2008-03-27 |
JP2010505009A (ja) | 2010-02-18 |
WO2008039670A1 (en) | 2008-04-03 |
DE602007008743D1 (de) | 2010-10-07 |
EP2069410A1 (en) | 2009-06-17 |
EP2069410B1 (en) | 2010-08-25 |
ATE478895T1 (de) | 2010-09-15 |
BRPI0718448A2 (pt) | 2013-12-10 |
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