CN101679779B - 带有生物钝性涂层的基底 - Google Patents
带有生物钝性涂层的基底 Download PDFInfo
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- CN101679779B CN101679779B CN2008800134117A CN200880013411A CN101679779B CN 101679779 B CN101679779 B CN 101679779B CN 2008800134117 A CN2008800134117 A CN 2008800134117A CN 200880013411 A CN200880013411 A CN 200880013411A CN 101679779 B CN101679779 B CN 101679779B
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- alkyl
- aryl
- group
- cycloalkyl
- thiazolinyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
- C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明提供了赋予基底表面降低的生物材料粘附的方法,包括下列步骤:(i)氧化基底表面;(ii)将包含一种或多种烯键式不饱和化合物的组合物施加到基底的氧化表面上;和(iii)固化所述组合物以形成涂层。
Description
本发明涉及赋予基底表面降低的生物材料粘附的方法、涉及涂布基底的方法和适用在所述方法中的化合物的混合物。
基底可以用杀生物剂处理以保护基底免受生物侵扰和生长。生物材料,如植物、藻类或微生物在基底表面上的不希望的积聚通常被称作生物污垢。常见防污剂是四丁基锡(TBT)或乙酸苯汞。防污剂会泄漏到环境中并因此污染环境。这些杀生物剂的泄漏会在目标生物体中造成抗性,且由于这些防污剂通常对非目标生物体,如人类和其它哺乳动物而言通常也是高毒性的,因此不能排除对这些生物体的不希望的伤害。
因此,本发明的目的是提供无需常见防污剂也能保护基底免受生物侵扰和生长的方法。该方法还应在技术上可以在现有设备上以大规模和以连续模式实行。
目的通过权利要求1和10的方法、权利要求17的基底和权利要求18的混合物实现。
本发明的赋予基底表面降低的生物材料粘附的方法包括下列步骤:
(i)氧化基底表面
(ii)将包含一种或多种烯键式不饱和化合物的组合物施加到基底的氧化表面上和
(iii)固化所述组合物以形成涂层。
生物材料可以是蛋白质、孢子、核酸、病毒或生物细胞以及生物细胞的片段或提取物。
蛋白质的实例是纤维状蛋白质,如肌动蛋白和微管蛋白;球蛋白,如白蛋白、纤维蛋白、凝血酶和免疫球蛋白;酶,如氧化还原酶、转移酶和水解酶;以及朊病毒。
孢子的实例是真菌、蕨类和拟蕨植物的孢子。
核酸的实例是脱氧核糖核酸和核糖核酸。
病毒的实例是腺病毒、AIDS病毒、λ噬菌体、T4噬菌体和T7噬菌体。
生物细胞的实例是古菌(archaea)、细菌细胞或真核细胞。
细菌细胞的实例是来自放线菌(Actinobacteria)门、衣原体(Chlamydia)门、蓝藻(Cyanobacteria)门、厚壁菌(Firmicutes)门、变形菌(Proteobacteria)门和螺旋体(Spirochaetes)门的细胞。放线菌门的属的实例是放线菌属(Actinomyces)、节杆菌属(Arthrobacter)、棒杆菌属(Corynebacterium)、诺卡氏菌属(Nocardia)和链霉菌属(Streptomyces)。厚壁菌门的属的实例是芽孢杆菌属(Bacillus)、肠球菌属(Enterococcus)、乳杆菌属(Lactobacillus)、乳球菌属(Lactococcus)、链球菌属(Streptococcus)、醋酸杆菌属(Acetobacterium)、梭菌属(Clostridium)、真杆菌属(Eubactrium)和太阳杆菌属(Heliobacterium)。变形菌门的属的实例是肠杆菌属(Enterobacter)、埃希氏菌属(Escherichia)、克雷伯氏菌属(Klebsiella)、沙门氏菌属(Salmonella)、假单胞菌属(Pseudomonas)、弧菌属(Vibrio)、Burkholdria、螺杆菌属(Helicobacter)和弯曲杆菌属(Campylobacter)。大肠杆菌(Escherichia coli)类的细胞是特别优选的细菌细胞。
真核细胞的实例是真菌细胞、人细胞、动物细胞和植物细胞。
真菌细胞的实例是霉菌、蘑菇和酵母细胞。酵母细胞的实例是酵母菌属(Saccharomyces)和假丝酵母属(Candida)的细胞。酿酒酵母(Saccharomyees cerevisae)和白假丝酵母(Candida albicans)类的细胞是特别优选的酵母细胞。
优选的生物材料是蛋白质、细菌细胞和生物细胞。更优选的生物材料是蛋白质、细菌细胞和真菌细胞。最优选的生物材料是细菌细胞,特别是大肠杆菌的那些。
通过将粘附到根据本发明的方法处理过的基底表面上的生物材料量与粘附到未处理基底的表面上的生物材料量进行比较,可以测定生物质与基底表面的粘附程度。
基底可以是二维物体,如板或薄膜,或任何三维物体;其可以是透明或不透明的。基底可以由纸、纸板、木材、皮革、金属、织物、玻璃、陶瓷、石头和/或聚合物制成。
金属的实例是铁、镍、钯、铂、铜、银、金、锌和铝,以及合金,如钢、黄铜、青铜和硬铝。
织物可以由天然纤维,如来自动物或植物来源的纤维,或由合成纤维制成。来自动物来源的天然纤维的实例是羊毛和丝。来自植物来源的天然纤维的实例是棉、亚麻和黄麻。合成织物的实例是聚酯、聚丙烯酰胺、聚烯烃如聚乙烯和聚丙烯、以及聚酰胺如尼龙和莱卡(lycra)。
陶瓷的实例是主要由粘土制成的产品,例如砖、瓷砖和瓷,以及技术陶瓷。技术陶瓷可以是氧化物如氧化铝、二氧化锆、二氧化钛和钛酸钡,碳化物如碳化钠、碳化硅或碳化硼,硼化物如硼化钛,氮化物如氮化钛或氮化硼,以及硅化物如硅化钠或硅化钛。
石头的实例是石灰石、花岗岩、片麻岩、大理石、板岩和砂岩。
聚合物的实例是丙烯酸类聚合物、苯乙烯类聚合物及其氢化产物、乙烯基聚合物及其衍生物、聚烯烃及其氢化或环氧化产物、醛聚合物、环氧化物聚合物、聚酰胺、聚酯、聚氨酯、聚碳酸酯、砜基聚合物和天然聚合物及其衍生物。
丙烯酸类聚合物可以是由至少一种丙烯酸类单体或由至少一种丙烯酸类单体和至少一种其它烯键式不饱和单体,如苯乙烯类单体、乙烯基单体、烯烃单体或马来酸类单体形成的聚合物。
丙烯酸类单体的实例是(甲基)丙烯酸、(甲基)丙烯酰胺、(甲基)丙烯腈、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸缩水甘油酯、甲基丙烯酸乙酰乙酰氧乙酯、丙烯酸二甲基氨基乙酯和丙烯酸二乙基氨基乙酯。苯乙烯类单体的实例是苯乙烯、4-甲基苯乙烯和4-乙烯基联苯。乙烯基单体的实例是乙烯醇、氯乙烯、偏二氯乙烯、乙烯基异丁基醚和乙酸乙烯酯。烯烃单体的实例是乙烯、丙烯、丁二烯和异戊二烯和它们的氯化或氟化衍生物,如四氟乙烯。马来酸类单体的实例是马来酸、马来酸酐和马来酰亚胺。
丙烯酸类聚合物的实例是聚(甲基丙烯酸甲酯)(PMMA)、聚(甲基丙烯酸丁酯)、聚丙烯腈(PAN)、聚丙烯酸、苯乙烯/丙烯酸2-乙基己酯共聚物、苯乙烯/丙烯酸共聚物。
苯乙烯类聚合物可以是由至少一种苯乙烯类单体或由至少一种苯乙烯类单体和至少一种乙烯基单体、烯烃单体和/或马来酸类单体形成的聚合物。苯乙烯类聚合物的实例是聚苯乙烯(PS)、苯乙烯丁二烯苯乙烯嵌段聚合物、苯乙烯乙烯丁二烯嵌段聚合物、苯乙烯乙烯丙烯苯乙烯嵌段聚合物和苯乙烯-马来酸酐共聚物。
乙烯基聚合物可以是由至少一种乙烯基单体或由至少一种乙烯基单体和至少一种烯烃单体或马来酸类单体形成的聚合物。乙烯基聚合物的实例是聚氯乙烯(PVC)、聚偏二氟乙烯(PVDF)、聚乙烯醇、聚乙酸乙烯酯、部分水解的聚乙酸乙烯酯和甲基乙烯基醚-马来酸酐共聚物。它们的衍生物的实例是羧基改性的聚乙烯醇、乙酰乙酰基改性的聚乙烯醇、双丙酮改性的聚乙烯醇和硅改性的聚乙烯醇。
聚烯烃可以是由至少一种烯烃单体或由至少一种烯烃单体和马来酸类单体形成的聚合物。聚烯烃的实例是低密度聚乙烯(LDPE)、高密度聚乙烯(HDPE)、聚丙烯(PP)、双轴取向的聚丙烯(BOPP)、聚丁二烯、聚四氟乙烯(Teflon-PTFE)、氯化聚乙烯和异丙烯-马来酸酐共聚物。
醛聚合物可以是由至少一种醛单体或聚合物和至少一种醇单体或聚合物、胺单体或聚合物和/或脲单体或聚合物形成的聚合物。醛单体的实例是甲醛、糠醛和丁醛。醇单体的实例是苯酚、甲酚、间苯二酚和二甲苯酚。聚醇的实例是聚乙烯醇。胺单体的实例是苯胺和三聚氰胺。脲单体的实例是脲、硫脲和双氰胺。醛聚合物的实例是由丁醛和聚乙烯醇形成的聚乙烯基丁醛。
环氧化物聚合物可以是由至少一种环氧化物单体和至少一种醇单体和/或胺单体形成的聚合物。环氧化物单体的实例是表氯醇和缩水甘油。醇单体的实例是苯酚、甲酚、间苯二酚、二甲苯酚、双酚A和乙二醇。环氧化物聚合物的实例是由表氯醇和双酚A形成的苯氧基树脂。
聚酰胺可以是由至少一种具有酰胺基团或氨基以及羧基的单体或由至少一种具有两个氨基的单体和至少一种具有两个羧基的单体形成的聚合物。具有酰胺基团的单体的实例是己内酰胺。二胺的实例是1,6-二氨基己烷。二羧酸的实例是己二酸、对苯二甲酸、间苯二甲酸和1,4-萘二甲酸。聚酰胺的实例是聚己二酰己二胺和聚己内酰胺。
聚酯可以是由至少一种具有羟基以及羧基的单体或由至少一种具有两个羟基的单体和至少一种具有两个羧基或内酯基团的单体形成的聚合物。具有羟基以及羧基的单体的实例是己二酸。二醇的实例是乙二醇。具有内酯基团的单体的实例是己内酯。二羧酸的实例是对苯二甲酸、间苯二甲酸和1,4-萘二甲酸。聚酯的实例是聚对苯二甲酸乙二酯(PET)。所谓的醇酸树脂也被认为属于聚酯聚合物。
聚氨酯可以是由至少一种二异氰酸酯单体和至少一种多元醇单体和/或聚胺单体形成的聚合物。二异氰酸酯单体的实例是己二异氰酸酯、甲苯二异氰酸酯、异佛尔酮二异氰酸酯和二苯甲烷二异氰酸酯。
聚碳酸酯的实例是聚(芳族碳酸酯)和聚(脂族碳酸酯)。聚(脂族碳酸酯)可以由二氧化碳和至少一种环氧化物形成。
砜基聚合物的实例是聚芳基砜、聚醚砜(PES)、聚苯基砜(PPS)和聚砜(PSF)。聚砜(PSF)是由4,4-二氯二苯砜和双酚A形成的聚合物。
天然聚合物的实例是淀粉、纤维素、明胶、caesin和天然橡胶。衍生物的实例是氧化淀粉、淀粉-乙酸乙烯酯接枝共聚物、羟乙基纤维素、羟丙基纤维素、甲基纤维素、硝基纤维素、乙基纤维素、羧甲基纤维素和乙酰基纤维素。
基底可以是用在医学领域中的基底。这类基底的实例是体内使用的基底,如植入物、人造器官、人造关节、人造血管和医用器材,如创伤护理绷带、导管、听诊器、管、注射器和针头。
基底可以是water liner或包装,例如食品包装。基底也可以是膜。
优选基底由聚合物制成。更优选基底由选自由苯乙烯类聚合物、乙烯基聚合物及其衍生物、聚烯烃、聚酯和砜基聚合物组成的组中的聚合物制成。基底再更优选由聚烯烃制成。再更优选基底由聚丙烯(PP)或双轴取向的聚丙烯(BOPP)制成。
由聚合物制成的基底优选是膜。
基底表面的氧化可以例如通过用电晕放电、等离子体、火焰、臭氧、电子束、X-射线或紫外线辐射等处理来进行。
电晕放电可以是这样的放电,以电晕为特征,并且在气体中的两个电极之一具有使其表面的电场明显高于电极之间的电场的形状时发生。常用空气作为气体。基底通常在环境压力下位于这两个电极之间的放电场中,例如通过使作为基底的薄膜在两个电极之间穿过。
等离子体可以是其中存在电子和离子的气体。等离子体可以通过用高温或高电场处理气体来产生。等离子体处理通常在真空室中在10至100Pa下在由惰性气体或反应性气体,例如氧气构成的气氛中用非热等离子体进行。
火焰可以是在将可燃气体和含氧气体(例如大气空气)合并并燃烧时形成的火焰。可燃气体的实例是丙烷、丁烷或民用燃气。火焰处理通常在环境压力下进行。
臭氧可以在电晕放电中由大气氧产生或通过紫外线辐射产生。
电子束可以由电子束加速器,例如由阴极射线管产生。
X-射线可以由X-射线发生器,例如由X-射线管产生。
表面的氧化优选通过用电晕放电、等离子体或火焰处理来进行。其更优选通过电晕放电处理或等离子体处理进行。
所述一种或多种烯键式不饱和化合物可以是能够聚合的任何烯键式不饱和化合物。
所述一种或多种烯键式不饱和化合物例如可具有下式:
其中
R1、R2和R3可以相同或不同并且可以是氢、卤素或C1-6-烷基,
A可以是芳基、卤素、CN、C(O)R4、C(O)OR5、OR6、OC(O)R7、NR8C(O)R9或C(O)NR10R11,其中芳基可以是未取代或如下所述取代,
其中
R4、R5、R6、R7、R10和R11可以相同或不同并且可以是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基、C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2或芳基-C1-30-亚烷基-芳基,且
R8和R9可以相同或不同并且可以具有与R5相同的含义,此外,可以与NC(O)一起形成4至7元环,
其中
C1-100-烷基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基和C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2可以是未取代的或被一个或多个C3-8-环烷基、芳基、OC2-30-烯基、卤素、CN、C(O)OR12、C(O)NR13R14、OR15、NR16R17、NHC(O)C(R18)=C(R19)R20、OC(O)C(R21)=C(R22)R23或C(O)OC(R24)=C(R25)R26取代;
C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、CN、C(O)OR12、C(O)NR13R14、OR15、NR16R17、NHC(O)C(R18)=C(R19)R20、OC(O)C(R21)=C(R22)R23或C(O)OC(R24)=C(R25)R26取代,
芳基或芳基-C1-30-亚烷基-芳基可以是未取代的或被一个或多个C1-6-烷基、C3-8-环烷基、C2-30-烯基、卤素、CN、C(O)OR12、C(O)NR13R14、OR15、NR16R17、NHC(O)C(R18)=C(R19)R20、OC(O)C(R21)=C(R22)R23或C(O)OC(R24)=C(R25)R26取代,其中
R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R25和R26可以相同或不同并且可以是氢或C1-6-烷基,
且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
卤素可以是氟、氯、溴或碘。C1-6-烷基可以是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基或己基。
C1-6-亚烷基-芳基-(C1-6-烷基)2的实例是异氰脲酸三乙酯。C1-6-亚烷基-C1-12-环烷基-C1-6-烷基的实例是二甲基三环癸烷。
芳基可以是苯基或萘基或杂芳基,如咪唑基、吡咯基或异氰尿酰基。芳基优选是苯基。
C1-6-烷基可以是带支链或直链的并且可以是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基或己基。
C1-100-烷基可以是带支链或直链的。C1-100-烷基的实例是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十五烷基、十六烷基、十八烷基、十九烷基(icosyl)、二十烷基、二十二烷基、二十四烷基和三十烷基。
C3-8-环烷基的实例是环丙基、环丁基、环戊基、环己基、环庚基和环辛基。
C2-30-烯基的实例是乙烯基和烯丙基。
芳基-C1-30-亚烷基-芳基的实例是苯基-亚乙基-苯基和苯基-亚丙基-苯基。
式1的烯键式不饱和化合物的实例是丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-乙基己酯、丙烯酸2-羟乙酯、甲基丙烯酸缩水甘油酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、丙烯腈、丙烯酰胺、甲基丙烯酸、甲基丙烯酰胺、乙酸乙烯酯、异丁基乙烯基醚、苯乙烯、N-乙烯基吡咯烷酮、氯乙烯、偏二氯乙烯、乙二醇二丙烯酸酯、六亚甲基二醇二丙烯酸酯、丙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、双酚A二丙烯酸酯、三环癸烷二甲醇二丙烯酸酯、4,4’-双(2-丙烯酰氧基乙氧基)二苯丙烷、丙烯酸乙烯酯、甲基丙烯酸乙烯酯、二乙烯基苯、琥珀酸二乙烯酯、乙二醇二乙烯基醚、二乙二醇二乙烯基醚、三乙二醇二乙烯基醚、甘油乙氧基化物三丙烯酸酯、甘油丙氧基化物三丙烯酸酯、三羟甲基丙烷乙氧基化物三丙烯酸酯、三羟甲基丙烷丙氧基化物三丙烯酸酯、季戊四醇乙氧基化物四丙烯酸酯、季戊四醇丙氧基化物三丙烯酸酯、季戊四醇丙氧基化物四丙烯酸酯、三羟甲基丙烷三丙烯酸酯、异氰脲酸三丙烯酸2-羟乙酯、乙氧基化(6)三羟甲基丙烷三丙烯酸酯、乙氧基化(9)三羟甲基丙烷三丙烯酸酯、乙氧基化(15)三羟甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、新戊二醇乙氧基化物二丙烯酸酯和新戊二醇丙氧基化物二丙烯酸酯、聚乙二醇(400)二丙烯酸酯、聚乙二醇(400)二甲基丙烯酸酯、聚乙二醇(600)二丙烯酸酯、聚乙二醇(600)二甲基丙烯酸酯和聚乙二醇-单-甲基丙烯酸酯。
优选地,R1、R2和R3相同或不同并且是氢或C1-6-烷基。
A优选是芳基、卤素、CN、C(O)OR5、OR6、OC(O)R7、NR8C(O)R9或C(O)NR10R11,其中R5、R6、R7、R10和R11是氢、C1-100-烷基、C2-30-烯基或芳基-C1-30-亚烷基-芳基;R8和R9相同或不同并具有与R5相同的含义,此外,可以与NC(O)一起形成4至7元环,且其中C1-100-烷基可以是未取代的或被一个或多个C3-8-环烷基、O-C2-30-烯基、OR15、NR16R17、OC(O)C(R21)=C(R22)R23、NHC(O)C(R18)=C(R19)R20或C(O)OC(R24)=C(R25)R26取代,且芳基可以是未取代的或被一个或多个C2-30-烯基或OC(O)C(R21)=C(R22)R23取代;R15、R16、R17、R21、R22、R23、R24、R25和R26可以相同或不同并且是氢或C1-6-烷基,且C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
更优选,A是C(O)OR5,其中R5是C1-100-烷基,其中C1-100-烷基被一个或多个OC(O)C(R21)=C(R22)R23取代,且C1-100-烷基中的一个或多个CH2-基团可以被-O-替代。
优选的式1的烯键式不饱和化合物的实例是乙二醇二丙烯酸酯、六亚甲基二醇二丙烯酸酯、丙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、甘油乙氧基化物三丙烯酸酯、甘油丙氧基化物三丙烯酸酯、三羟甲基丙烷乙氧基化物三丙烯酸酯、三羟甲基丙烷丙氧基化物三丙烯酸酯、季戊四醇乙氧基化物四丙烯酸酯、季戊四醇丙氧基化物三丙烯酸酯、季戊四醇丙氧基化物四丙烯酸酯、三羟甲基丙烷三丙烯酸酯、乙氧基化(6)三羟甲基丙烷三丙烯酸酯、乙氧基化(9)三羟甲基丙烷三丙烯酸酯、乙氧基化(15)三羟甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、新戊二醇乙氧基化物二丙烯酸酯、新戊二醇丙氧基化物二丙烯酸酯、聚乙二醇(400)二丙烯酸酯、聚乙二醇(400)二甲基丙烯酸酯、聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯。
这些化合物例如可购自Sartomer Company。或者,聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯可以例如通过使聚乙二醇(600)分别与丙烯酸甲酯和甲基丙烯酸甲酯反应来制备。
最优选,A是C(O)OR5,其中R5是C30-60-烷基,其中C30-60-烷基可以是带支链或直链的并且被一个或多个OC(O)C(R21)=C(R22)R23取代,且C30-60-烷基中的一个或多个CH2-基团可以被-O-替代。
尤其优选的式1的烯键式不饱和化合物的实例是聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯、乙氧基化(9)三羟甲基丙烷三丙烯酸酯和乙氧基化(15)三羟甲基丙烷三丙烯酸酯。聚乙二醇(600)二丙烯酸酯是最优选的式1的化合物。
所述一种或多种烯键式不饱和化合物也可以是烯丙基,例如邻苯二甲酸二烯丙酯、磷酸三烯丙酯和异氰脲酸三烯丙酯。
所述一种或多种烯键式不饱和化合物也可以是能够形成具有至少五个单体单元的聚合物的大分子单体,该大分子单体具有1’000至1’000’000’000克/摩尔的分子量并带有具有烯键式不饱和基团的侧链。这类大分子单体的实例是(甲基)丙烯酰基-改性的聚乙烯醇、(甲基)丙烯酰基-改性的部分水解的聚乙酸乙烯酯、(甲基)丙烯酰基-改性的甲基乙烯基醚-马来酸酐共聚物、(甲基)丙烯酰基-改性的甲基异丙烯-马来酸酐共聚物、(甲基)丙烯酰基-改性的聚氨酯和(甲基)丙烯酰基-改性的纤维素。
所述一种或多种烯键式不饱和化合物优选是式1的化合物。
优选,所述组合物还可以包含溶剂。
溶剂可以是水、有机溶剂或其混合物。
有机溶剂的实例是C1-4-链烷醇、C2-4-多元醇、C3-6-酮、C4-6-醚、C2-3-腈、硝基甲烷、二甲亚砜、二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮和环丁砜,其中C1-4-链烷醇和C2-4-多元醇可以被C1-4-烷氧基取代。C1-4-链烷醇的实例是甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、仲丁醇和叔丁醇。其C1-4-烷氧基衍生物的实例是2-乙氧基乙醇和1-甲氧基-2-丙醇。C2-4-多元醇的实例是乙二醇和丙三醇。C3-6-酮的实例是丙酮和甲乙酮。C4-6-醚的实例是二甲氧基乙烷、二异丙基醚和四氢呋喃。C2-3-腈的实例是乙腈。有机溶剂优选选自C1-4-链烷醇、C2-4-多元醇、C3-6-酮、二甲基甲酰胺和二甲基乙酰胺,其中C1-4-链烷醇和C2-4-多元醇可以被C1-4-烷氧基取代。有机溶剂更优选是C1-4-链烷醇。
优选,溶剂是水或水和有机溶剂的混合物。
所述组合物还可以包含一种或多种自由基引发剂。所述一种或多种自由基引发剂可以是热引发剂,如2,2-偶氮二异丁腈或光引发剂。优选,所述一种或多种自由基引发剂是光引发剂。
光引发剂可以具有下式:
其中
L可以是氢或
其中C1-6-亚烷基可以是未取代的或被羟基取代,且
R27、R28和R29可以相同或不同并且可以是氢、卤素、羟基、C1-6-烷基、芳基、O-C1-6-烷基、O-芳基、S-C1-6-烷基、S-芳基或NR30R31,
其中R30和R31可以相同或不同并且可以是氢或C1-6-烷基,或与氮一起形成5至7元环,其中该环的CH2基团可以被-O-替代,且C1-6-烷基、O-C1-6-烷基和S-C1-6-烷基可以是未取代的或被一个或多个羟基、C2-30-烯基、OC(O)C2-30-烯基或芳基取代,且
X可以是
其中E和G可以是-O-、-S-或NR40,其中R40可以是氢或C1-6-烷基,或R40分别和R32或和R35可以与氮一起形成5至7元环,其中该环的CH2基团可以被-O-、NH、NC(O)C(R41)C=C(R42)R43和/或
R32、R35和R39可以相同或不同并且可以是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基或C(O)R44,
R36、R37和R38可以相同或不同并且可以是氢、C1-100-烷基、O-C1-100-烷基、S-C1-100-烷基、NR45C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基或C(O)R44,其中R45可以具有与R32相同的含义,且R44可以具有与R36相同的含义,
R33和R34可以具有与R36相同的含义,此外,可以与连接碳原子一起形成5至7元环,
C1-100-烷基和C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、氨基、羟基、CN、COOH、C(O)R46、C(O)OR47、C(O)NR48R49、OR50、OC(O)R51、OC(O)C(R52)=C(R53)R54、C(O)OC(R55)=C(R56)R57、
芳基可以是未取代的或被一个或多个C1-4-烷基、C3-8-环烷基、C2-30-烯基、卤素、羟基、CN、COOH、C(O)R46、C(O)OR47、C(O)NR48R49、OR50、OC(O)R51、OC(O)C(R52)=C(R53)R54或C(O)OC(R55)=C(R56)R57取代;
其中R41、R42、R43、R46、R47、R48、R49、R50、R51、R52、R53、R54、R55、R56和R57可以相同或不同并且可以是氢或C1-6-烷基,
且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NR40-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
C1-6-亚烷基的实例是亚甲基、亚丙基和亚丁基。
式2的光引发剂的实例是苯偶姻醚如苯偶姻乙基醚,苄基单缩酮如2,2-二乙氧基-1-苯基乙酮和2,2-二乙氧基-1,2-二苯基乙酮,α-取代的苯乙酮衍生物如2-羟基-2-甲基苯丙酮、1-羟基环己基苯基酮、2-甲基-4’-(甲硫基)-2-吗啉基苯丙酮和2-苄基-2-(二甲基氨基)-4’-吗啉基苯丁酮,酰基膦氧化物如二苯基(2,4,6-三甲基苯甲酰基)-氧化膦或苯基双(2,4,6-三甲基苯甲酰基)-氧化膦,α-酰基肟酯如1-[4-(苯硫基)苯基]-2-(O-苯甲酰基肟)辛-1,2-二酮,和苯基乙醛酸酯如二乙二醇二(苯基乙醛酸酯)、三乙二醇二(苯基乙醛酸酯)、聚乙二醇(150)二(苯基乙醛酸酯)、聚乙二醇(300)二(苯基乙醛酸酯)、聚乙二醇(400)二(苯基乙醛酸酯)和聚乙二醇(600)二(苯基乙醛酸酯)。
在优选的式2的化合物中,R27、R28和R29可以相同或不同并且是氢、羟基、C1-6-烷基、O-C1-6-烷基、S-C1-6-烷基、S-芳基或NR30R31,其中R30和R31可以相同或不同并且可以是氢或C1-6-烷基,或与氮一起形成5至7元环,其中该环的CH2基团可以被-O-替代,且C1-6-烷基和O-C1-6-烷基可以是未取代的或被一个或多个羟基、C2-30-烯基或芳基取代,且
X是
其中E和G是-O-或NR40,其中R40可以是氢或C1-6-烷基,或R40分别和R32或和R35可以与氮一起形成5至7元环,其中该环的CH2基团可以被-O-、NH、NC(O)C(R41)C=C(R42)R43和/或
R32、R35和R39可以相同或不同并且是氢、C1-100-烷基、C2-30-烯基、芳基或C(O)R44;R36、R37和R38可以相同或不同并且是氢、C1-100-烷基、O-C1-100-烷基或C(O)R44;R33和R34可以具有与R36相同的含义,此外可以与连接碳原子一起形成5至7元环,R44具有与R36相同的含义,
C1-100-烷基和C2-30-烯基可以是未取代的或被一个或多个芳基、氨基、羟基、OC(O)C(R52)=C(R53)R54、C(O)OC(R55)=C(R56)R57、
其中R41、R42、R43、R52、R53、R54、R55和R56和R57可以相同或不同并且是氢或C1-6-烷基,
芳基可以是未取代的或被一个或多个C1-4-烷基取代,且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-和/或-NR40-替代。
在更优选的式2的化合物中,R27、R28和R29可以相同或不同并且是氢、羟基、C1-6-烷基、O-C1-6-烷基、S-C1-6-烷基或NR30R31,其中R30和R31可以相同或不同并且是氢或C1-6-烷基;其中C1-6-烷基和O-C1-6-烷基可以是未取代的或被一个或多个羟基、C2-30-烯基或芳基取代,且
X是
其中G是-O-或NR40、其中R40可以是氢,或R40和R35可以与氮一起形成5至7元环,其中该环的CH2基团可以被NH、NC(O)C(R41)C=C(R42)R43和/或
R35是氢、C1-100-烷基或C2-30-烯基,其中C1-100-烷基和C2-30-烯基可以是未取代的或被一个或多个氨基、羟基、OC(O)C(R52)=C(R53)R54和/或
其中R41、R42、R43、R52、R53和R54可以相同或不同并且是氢或C1-6-烷基,且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-和/或-NR40-替代。
在最优选的式2的化合物中,R27、R28和R29是氢或C1-6-烷基,且
X是
其中G是-O-;R35是C1-100-烷基,其中C1-100-烷基可以是未取代的或被一个或多个
C1-100-烷基中的一个或多个CH2-基团可以被-O-替代。
尤其优选的式2的光引发剂是二乙二醇二(苯基乙醛酸酯)、三乙二醇二(苯基乙醛酸酯)、聚乙二醇(150)二(苯基乙醛酸酯)、聚乙二醇(300)二(苯基乙醛酸酯)、聚乙二醇(400)二(苯基乙醛酸酯)和聚乙二醇(600)二(苯基乙醛酸酯)。尤其优选聚乙二醇(600)二(苯基乙醛酸酯)。
光引发剂也可以是二茂钛,或者是二苯甲酮或噻吨酮衍生物与助引发剂(例如叔胺)的组合。但优选地,光引发剂为式2的化合物。
所述组合物也可以包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物。通常,这些化合物具有生物杀灭活性。带有一个或多个烯键式不饱和基团的季铵化合物可以具有下式:
其中
R58、R59和R60可以相同或不同并且是氢、卤素或C1-6-烷基,
R61、R62和R63可以相同或不同并且是C1-30-烷基、C2-30-烯基、C3-8-环烷基、芳基,或R61和R62与铵基团的N一起形成4至8元环、其中该环的一个CH2基团可以被NH或O替代,
Q和Y可以相同或不同并且是C1-15-亚烷基,
M是桥连基,
n和m可以相同或不同并且是0或1,
J-是阴离子,
其中C1-30-烷基、C2-30-烯基、C3-8-环烷基或C1-15-亚烷基可以是未取代的或被一个或多个芳基、OC2-6-烯基、卤素、CN、C(O)OR64、C(O)NR65R66、OR67、NR68R69、NHC(O)C(R70)=C(R71)R72、OC(O)C(R73)=C(R74)R75或C(O)OC(R76)=C(R77)R78取代;
其中芳基可以是未取代的或被一个或多个C1-6-烷基、C2-6-烯基、OC2-6-烯基、卤素、CN、C(O)OR64、C(O)NR65R66、OR67、NR68R69、NHC(O)C(R70)=C(R71)R72、OC(O)C(R73)=C(R74)R75或C(O)OC(R76)=C(R77)R78取代;
其中R64、R65、R66、R67、R68、R69、R70、R71、R72、R73、R74、R75、R76、R77和R78可以相同或不同并且是氢或C1-6-烷基,
且C1-15-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代。
C1-30-烷基可以是带支链或直链的。C1-30-烷基的实例是甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十五烷基、十六烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基和三十烷基。
C1-15-亚烷基的实例是亚甲基、亚丙基和亚丁基。
桥连基M的实例是C3-8-亚环烷基、亚芳基、聚合物、OC(O)、C(O)O、NH(CO)和C(O)NH。亚芳基可以是亚苯基。聚合物的实例是聚乙烯亚胺。
J-可以是任何阴离子,例如硫酸根、亚硫酸根、碳酸根、磷酸根或卤素离子。卤素离子可以是氟离子、氯离子、溴离子或碘离子。
带有一个或多个烯键式不饱和基团的季铵化合物的实例是丙烯酸三甲基氨基乙基酯氯化物、甲基丙烯酸三甲基氨基乙基酯氯化物、丙烯酸三甲基氨基十四烷基酯氯化物、丙烯酸三甲基氨基十六烷基酯氯化物、丙烯酸三甲基氨基十八烷基酯氯化物和二烯丙基二甲基氯化铵和下式的化合物:
和
更优选的带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R58、R59和R60可以相同或不同并且是氢或C1-6-烷基,
R61、R62和R63可以相同或不同并且是C1-30-烷基或C2-30-烯基,
Q和Y可以相同或不同并且是C1-15-亚烷基,
M是选自由亚芳基、聚合物、OC(O)和C(O)O组成的组的桥连基,
n和m可以相同或不同并且是0或1,
J-是卤素离子,
其中C1-30-烷基、C2-30-烯基或C1-15-亚烷基可以是未取代的或被一个或多个OC2-6-烯基、C(O)OR64、C(O)NR65R66、OR67、NR68R69、NHC(O)C(R70)=C(R71)R72、OC(O)C(R73)=C(R74)R75或C(O)OC(R76)=C(R77)R78取代;
其中R64、R65、R66、R67、R68、R69、R70、R71、R72、R73、R74、R75、R76、R77和R78可以相同或不同并且是氢或C1-6-烷基,
且C1-15-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2、CH-CH=CH2、NH和/或O替代。
最优选的带有一个或多个烯键式不饱和基团的季铵化合物具有下式:
其中
R58、R59和R60可以相同或不同并且是氢或C1-6-烷基,
R61、R62和R63可以相同或不同并且是C1-30-烷基,
Q和Y可以相同或不同并且是C1-6-亚烷基,
M是选自由聚合物和OC(O)组成的组的桥连基,
n和m可以相同或不同并且是0或1,
J-是卤素离子,
其中C1-30-烷基或C1-6-亚烷基可以是未取代的或被一个或多个OR67取代,
其中R67可以是氢或C1-6-烷基,
且C1-6-亚烷基中的一个或多个CH2-基团可以被N-CH2-CH=CH2替代。
C1-6-亚烷基的实例是亚甲基、亚丙基和亚丁基。
化合物3A和3B是尤其优选的带有一个或多个烯键式不饱和基团的季铵化合物。
化合物3A可以通过使聚乙烯亚胺与N-3-氯-2-羟丙基-N-月桂基-二甲基氯化铵和烯丙基溴反应来制备。化合物3B可以如S.M.Hamid和D.C.Sherrington,Polymer 1987,28,325至331中所述通过使甲基丙烯酸N,N-二甲基氨基乙酯与十二烷基溴反应来制备。
所述组合物还可以包含其他组分,如杀生物剂、表面活性剂和消泡剂。
杀生物剂的实例是5-氯-2-(2,4-二氯苯氧基)苯酚,例如以商品名 DP300出售;N’-叔丁基-N-环丙基-6-(甲硫基)-1,3,5-三嗪-2,4-二胺,例如以商品名1051出售;2-噻唑-4-基-1H-苯并咪唑,例如以商品名F3000出售;氯己定;没食子酸;粘溴酸;衣康酸;和氨基甲酸3-碘-2-丙炔基丁基酯,例如以商品名MaguardTMI-100出售。
表面活性剂的实例是阴离子型表面活性剂,如十二烷基硫酸钠或月桂基硫酸铵,阳离子型表面活性剂,如鲸蜡基三甲基溴化铵或鲸蜡基氯化吡啶鎓,两性表面活性剂,如十二烷基甜菜碱,和非离子型表面活性剂,如聚(环氧乙烷)和聚(环氧丙烷)的共聚物。
所述组合物可以包含基于组合物重量为0.001至100重量%的所述一种或多种烯键式不饱和化合物。其优选包含0.01至20重量%的所述一种或多种烯键式不饱和化合物,更优选0.1至10重量%。
所述组合物可以包含基于组合物重量为0至99.999重量%的溶剂。其优选包含10至99.9重量%的溶剂,更优选80至99重量%。
所述组合物可以包含基于组合物重量为0至50重量%的所述一种或多种自由基引发剂。其优选包含0.01至20重量%的所述一种或多种自由基引发剂,更优选0.1至10重量%。
所述组合物可以包含基于组合物重量为0至50重量%的一种或多种带有一个或多个烯键式不饱和基团的季铵化合物。其优选包含0.001至10重量%的季铵化合物,更优选0.01至5重量%。
所述组合物可以包含基于组合物重量为0至50重量%的其他组分。其优选包含0.001至10重量%的其他组分,更优选0.01至5重量%。
优选,一种或多种烯键式不饱和化合物/溶剂的重量比为0.01/100至50/100,更优选0.1/100至20/100,最优选0.5/100至10/100。
优选,一种或多种烯键式不饱和化合物/一种或多种自由基引发剂的摩尔比为100/1至1/100,优选10/至1/10,更优选2/1至1/2。最优选,所述一种或多种烯键式不饱和化合物和所述一种或多种自由基引发剂以大致等摩尔量使用。
所述组合物可以是溶液、乳液或分散体。该组合物优选是溶液。该组合物可以例如使用线棒或通过浸渍、喷涂或旋涂法施加。
可以通过所述一种或多种烯键式不饱和化合物和能够聚合并任选存在于该组合物中的其它组分(例如带有一个或多个烯键式不饱和基团的季铵化合物)的聚合实现所述组合物的固化。
如果在基底的氧化表面上存在充足自由基,则所述一种或多种烯键式不饱和化合物可以在施加后聚合而无需任何其他处理。但是,通常,通过用热、电子束或电磁辐射处理来引发聚合。电磁辐射的实例X-射线、γ射线、紫外线辐射、红外辐射、可见光或微波。优选通过用电磁辐射处理,更优选通过用紫外线辐射处理来引发聚合。通常,紫外线辐射在60至300瓦特/cm和1至1000米/分钟,优选10至200米/分钟的带速下进行。
优选,在仅含痕量氧的惰性气体气氛下进行聚合。惰性气体的实例是氮气、氩气、二氧化碳和氦气。优选,惰性气体气氛中存在的氧的量低于1000体积ppm,更优选低于500体积ppm,最优选低于150体积ppm。
固化涂层可具有0.1至100微米,优选1至50微米的厚度。
杀生物剂可以例如在表面氧化之前(在步骤(i)之前)、在表面氧化之后和在施加包含烯键式不饱和化合物的组合物之前(在步骤(i)之后和在步骤(ii)之前)、在施加该所述组合物之后和在固化之前(在步骤(ii)之后和在步骤(iii)之前)或在固化所述组合物之后(在步骤(iii)之后)施加在基底表面上。
基底可以用另外的涂层涂布,该另外的涂层可以在由本发明的方法形成的涂层之前或之后施加到基底上。
涂布基底的方法也是本发明的一部分,该方法包括下列步骤:
(i)氧化基底表面
(ii)将包含一种或多种具有下式的烯键式不饱和化合物的组合物施加到基底的氧化表面上
其中R79、R80和R81可以相同或不同并且是氢、卤素或C1-6-烷基,且Y是C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基或O-C30-100-烷基,其中C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基或O-C30-100-烷基可以是未取代的或被一个或多个OC2-30-烯基、OR82、NR83R84、OC(O)C(R85)C=C(R86)R87和/或NHC(O)C(R88)C=C(R89)R90取代,其中R82、R83、R84、R85、R86、R87、R88、R89和R90可以相同或不同并且是氢或C1-6-烷基,且其中C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基或O-C30-100-烷基中的一个或多个CH2-基团可以被-O-和/或-NH-替代,和
(iii)固化所述组合物以形成涂层。
C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基和O-C30-100-烷基中的C30-100-烷基可以是带支链或直链的。
优选的式1A的烯键式不饱和化合物的实例是聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯。
在优选的式1A化合物中,R79、R80和R81可以相同或不同并且是氢或C1-6-烷基,且Y是C(O)-OC30-100-烷基,其可以是未取代的或被一个或多个OC2-30-烯基、OR82、NR83R84、OC(O)C(R85)C=C(R86)R87和/或NHC(O-)C(R88)C=C(R89)R90取代,其中R82、R83、R84、R85、R86、R87、R88、R89和R90可以相同或不同并且是氢或C1-6-烷基,且其中C(O)-OC30-100-烷基中的一个或多个CH2-基团可以被一O-和/或-NH-替代。
在更优选的式1A化合物中,R79、R80和R81可以相同或不同并且是氢或C1-6-烷基,且Y是C(O)-OC30-60-烷基,其可以是未取代的或被一个或多个OC(O)C(R85)C=C(R86)R87取代,且其中C(O)-OC30-60-烷基中的一个或多个CH2-基团可以被-O-替代。
C(O)-OC30-60-烷基中的C30-60-烷基可以是带支链或直链的。
特别优选的式1A化合物是聚乙二醇(600)二丙烯酸酯和聚乙二醇(600)二甲基丙烯酸酯。
基底的定义如上所述。表面的氧化、所述组合物的施加和所述组合物的固化也如上所述。
可通过这一方法获得的基底也是本发明的一部分。
一种或多种烯键式不饱和化合物和一种或多种自由基光引发剂的混合物也是本发明的一部分,所述烯键式不饱和化合物具有下式:
其中R79、R80和R81可以相同或不同并且是氢、卤素或C1-6-烷基,且Y是C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基或O-C30-100-烷基,其中C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基或O-C30-100-烷基可以是未取代的或被一个或多个OC2-30-烯基、OR82、NR83R84、OC(O)C(R85)C=C(R86)R87和/或NHC(O)C(R88)C=C(R89)R90取代,其中R82、R83、R84、R85、R86、R87、R88、R89和R90可以相同或不同并且是氢或C1-6-烷基,且其中C(O)-OC30-100-烷基、C(O)-NHC30-100-烷基或O-C30-100-烷基中的一个或多个CH2-基团可以被-O-和/或-NH-替代,
所述自由基光引发剂具有下式:
其中
L可以是氢或
其中C1-6-亚烷基可以是未取代的或被羟基取代,且
R27、R28和R29可以相同或不同并且可以是氢、卤素、羟基、C1-6-烷基、芳基、O-C1-6-烷基、O-芳基、S-C1-6-烷基、S-芳基或NR30R31,
其中R30和R31可以相同或不同并且可以是氢或C1-6-烷基,或与氮一起形成5至7元环,其中该环的CH2基团可以被-O-替代,且C1-6-烷基、O-C1-6-烷基和S-C1-6-烷基可以是未取代的或被一个或多个羟基、C2-30-烯基、OC(O)C2-30-烯基或芳基取代,且
X可以是
其中E和G可以是-O-、-S-或NR40,其中R40可以是氢或C1-6-烷基,或
R40分别和R32或和R35可以与氮一起形成5至7元环,其中该环的CH2基团可以被-O-、NH、NC(O)C(R41)C=C(R42)R43和/或
R32、R35和R39可以相同或不同并且可以是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基或C(O)R44,
R36、R37和R38可以相同或不同并且可以是氢、C1-100-烷基、O-C1-100-烷基、S-C1-100-烷基、NR45C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基或C(O)R44,其中R45可以具有与R32相同的含义,且R44可以具有与R36相同的含义,R33和R34可以具有与R36相同的含义,此外,可以与连接碳原子一起形成5至7元环,
C1-100-烷基和C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、氨基、羟基、CN、COOH、C(O)R46、C(O)OR47、C(O)NR48R49、OR50、OC(O)R51、OC(O)C(R52)=C(R53)R54、C(O)OC(R55)=C(R56)R57、
或取代,
芳基可以是未取代的或被一个或多个C1-4-烷基、C3-8-环烷基、C2-30-烯基、卤素、羟基、CN、COOH、C(O)R46、C(O)OR47、C(O)NR48R49、OR50、OC(O)R51、OC(O)C(R52)=C(R53)R54或C(O)OC(R55)=C(R56)R57取代;
其中R41、R42、R43、R46、R47、R48、R49、R50、R51、R52、R53、R54、R55、R56和R57可以相同或不同并且可以是氢或C1-6-烷基,
且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NR40-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
对式1A的烯键式不饱和化合物和光引发剂2给出的优选情况在此也适用。
本发明的方法的优点在于,它们提供涂有涂层的基底,生物材料对该涂层上表现出降低的粘附性。这些涂布的基底表现出提高的对生物材料的抗性并因此不再需要额外的可基于重金属并且高毒性的杀生物剂的处理。本发明的方法的另一优点在于,可以在现有印刷设备上在大规模连续工艺中简单地用表现出降低的与生物材料的粘附性的涂层涂布基底。
实施例
实施例1
ExxonMobil Chemical Company供应的50微米宽的双轴取向聚丙烯(BOPP)膜在两面上都使用距BOPP膜0.8毫米的一个陶瓷电极进行电晕预处理,带速为3米/分钟,电晕放电为1×600W。然后,使用4微米线棒在该BOPP膜的两面上都施加Sartomer Company以SR-610出售的聚乙二醇(600)二丙烯酸酯(1B)在异丙醇中的1重量%溶液。储存该处理过的BOPP膜直至异丙醇蒸发。将该处理过的干BOPP膜在含有大约500ppm氧的氮气氛下使用在50米/分钟带速下的带有输出为120W/cm的中压汞灯的UV处理器和分色反射镜照射。
实施例2
重复实施例1的方法,不同的是使用1B和聚乙二醇(600)二(苯基乙醛酸酯)(2A)(其如WO 06/067061的实施例3中所述制备)的等摩尔混合物的1重量%溶液代替1B的1重量%溶液。
实施例3
重复实施例2的方法,不同的是使用12微米线棒代替4微米线棒。
实施例4
重复实施例2的方法,不同的是使用90重量%的1B和2A的等摩尔混合物(基于1B、2A和3A的总重量)和10重量%杀生物剂3A(基于1B、2A和3A的总重量)在异丙醇中的1重量%溶液代替1B和2A的等摩尔混合物的1重量%溶液。
如下制备化合物3A:将在乙醇(60克)中的N-3-氯-2-羟基丙基-N-月桂基-二甲基氯化铵(10.35克)和氢氧化钾(1.71克)添加到聚乙烯亚胺(5克)的溶液中,并将该混合物在氮气下在80℃下加热29小时。添加烯丙基溴(5.63克)和氢氧化钾(2.6克),并将该混合物在回流下搅拌6小时。将该反应混合物冷却,过滤并浓缩产生不透明的浅黄色浆(syryp)。在真空中干燥22小时后,获得8.6克化合物3A。可以通过NMR鉴定聚胺、十二烷基和烯丙基部分。对每个十二烷基部分而言,存在大约一个烯丙基部分,对所存在的每九个亚乙基氨基部分而言,存在大约一个十二烷基部分和一个烯丙基部分。
实施例5
重复实施例4的方法,不同的是使用90重量%1B和2A的等摩尔混合物(基于1B、2A和3B的总重量)和10重量%3B(基于1B、2A和3B的总重量)在异丙醇中的1重量%溶液代替90重量%1B和2A的等摩尔混合物(基于1B、2A和3A的总重量)和10重量%3A(基于1B、2A和3A的总重量)的1重量%溶液。如S.M.Hamid和D.C.Sherrington,Polymer 1987,28,325至331中所述制备3B。
1HNMR(300MHz,CDCl3):0.87(t,3H,烷基末端CH3),1.24至1.33(m,18H,烷基CH2),1.7(m,2H,N-CH2CH 2),1.95(s,3H,烯丙基CH3),3.49(s,6H,N(CH3)2),3.6(m,2H,NCH2),4.16(m,2H,O-CH2),4.64,(m,2H,O-CH2CH 2),5.67,(s,1H,顺式乙烯基H),6.14(s,1H,反式乙烯基H)。
实施例6
ExxonMobil Chemical Company供应的50微米宽的双轴取向聚丙烯(BOPP)膜在两面上都使用距BOPP膜1.5毫米的两个陶瓷电极(15’000V,500mA,10至40kHz)进行电晕预处理,带速为50米/分钟,电晕放电为3×700W。然后,使用4微米大线棒在该BOPP膜的两面上都施加1B和2A的等摩尔混合物在异丙醇中的1重量%溶液。储存该处理过的BOPP膜直至异丙醇蒸发。将该处理过的干BOPP膜在含有大约500ppm氧的氮气氛下使用在50米/分钟带速下的带有输出为80W/cm的中压汞灯的UV处理器和分色反射镜照射。
实施例7
重复实施例6的方法,不同的是使用带有输出为120W/cm的中压汞灯的UV处理器代替带有输出为80W/cm的中压汞灯的UV处理器。
实施例8
重复实施例6的方法,不同的是使用1B和2A的等摩尔混合物的10重量%溶液代替1B和2A的等摩尔混合物的1重量%溶液。
实施例9
重复实施例8的方法,不同的是使用带有输出为120W/cm的中压汞灯的UV处理器代替带有输出为80W/cm的中压汞灯的UV处理器。
实施例10
重复实施例8的方法,不同的是使用带有输出为200W/cm的中压汞灯的UV处理器代替带有输出为80W/cm的中压汞灯的UV处理器。
实施例11
ExxonMobil Chemical Company供应的50微米宽的双轴取向聚丙烯(BOPP)膜在两面上都使用距BOPP膜1.5毫米的两个陶瓷电极(15’000V,500mA,10至40kHz)进行电晕预处理,带速为50米/分钟,电晕放电3×700W。然后,使用喷雾瓶通过喷涂在该BOPP膜的两面上都施加1B和2A的等摩尔混合物在异丙醇中的1重量%溶液。储存该处理过的BOPP膜直至异丙醇蒸发。将该处理过干BOPP膜在含有大约70至80ppm氧的氮气氛下使用在50米/分钟带速下的带有输出为120W/cm的中压汞灯的UV处理器和分色反射镜照射。
实施例12
重复实施例11的方法,不同的是通过浸渍而非喷涂施加1B和2A的等摩尔混合物的1重量%溶液。
实施例13
重复实施例11的方法,不同的是使用1B和2A的等摩尔混合物在异丙醇中的3重量%溶液代替1重量%溶液。
实施例14
重复实施例12的方法,不同的是使用1B和2A的等摩尔混合物在异丙醇中的3重量%溶液代替1重量%溶液。
实施例15
重复实施例11的方法,不同的是使用1B和2A的等摩尔混合物在异丙醇中的6重量%溶液代替1重量%溶液。
实施例16
重复实施例12的方法,不同的是使用1B和2A的等摩尔混合物在异丙醇中的6重量%溶液代替1重量%溶液。
测试细菌细胞在实施例1至16的处理过的BOPP膜上的粘附性
实施例1至16中获得的处理过的BOPP膜的一面通过粘性胶带粘贴到载玻片上。在该处理过的BOPP膜的另一面上放置聚合物垫圈。向该垫圈中加入100微升HEPES缓冲液(150mM,pH=7.4),然后400微升含大约109个细胞/毫升大肠杆菌K12的溶液(获自Professor Sokurenko,University of Washington,Seattle,WA 98195,USA)。在37℃下培养20分钟后,用HEPES缓冲液(10×300微升)洗除未附着到该处理过的BOPP膜上的细菌细胞。将该BOPP膜成像,并计数粘附到该处理过的BOPP膜的表面上的细菌细胞数。
也用未处理的BOPP膜(对比例1),和使用距BOPP膜0.8毫米的一个陶瓷电极,在3米/分钟带速,1×600W电晕放电下的电晕预处理的BOPP膜(对比例2),和使用距BOPP膜1.5毫米的两个陶瓷电极,在50米/分钟带速,3×700W电晕放电下的电晕预处理的BOPP膜(对比例3)重复相同程序。粘附到未处理的BOPP膜上的细菌细胞数相当于100%的细菌细胞粘附。结果列在下表1中:
表1
在成像之前,C系列的BOPP膜也a)在蒸馏水中储存3周,和b)在2007年2月在Frick/Switzerland花园中储存(暴露在室外条件,如目光、风和雨中)3周。
结果列在下表2中:
表2
a未测得。
实施例17
将Pentaplast GMBH供应的250微米宽的聚对苯二甲酸乙二酯(PET)箔用O2等离子体处理10秒。然后通过旋涂(1000rpm)在PET箔的一面上施加Sartomer Company以SR-610出售的聚乙二醇(600)二丙烯酸酯(1B)和如WO 06/067061的实施例3中所述制备的聚乙二醇(600)二(苯基乙醛酸酯)(2A)的60/40(mol/mol)混合物在异丙醇中的3重量%溶液。储存该处理过的PET箔直至异丙醇蒸发。将该处理过的干PET箔含有大约20ppm氧的氮气氛下用350W压力汞灯和320nm滤光片进行UV照射5分钟。所得涂层具有100纳米厚度并在用水或皂溶液洗涤时稳定20分钟。
实施例18
重复实施例17的方法,不同的是使用1B、2A和Sartomer Company以Sartomer CD-552出售的式1C的单甲氧基化甲基丙烯酸酯的2/10/88(mol/mol/mol)混合物在乙醇中的3重量%溶液代替1B和2A的60/40(mol/mol)混合物在异丙醇中的3重量%溶液。
实施例19
重复实施例18的方法,不同的是使用1B、2A和1C的2/10/88(mol/mol/mol)混合物的6重量%溶液代替1B、2A和1C的2/10/88(mol/mol/mol)混合物的3重量%溶液。
测试细菌细胞在实施例17至19的处理过的PET箔上的粘附
与上述实施例1至16的处理过的BOPP膜类似地测试细菌细胞在实施例17至19的处理过的PET箔上的粘附。结果列在下表3中:
表3
Claims (9)
1.赋予基底表面降低的生物材料粘附的方法,包括下列步骤:
(i)氧化基底表面
(ii)将包含一种或多种烯键式不饱和化合物的组合物施加到所述基底的氧化表面上和
(iii)固化所述组合物以形成涂层。
2.权利要求1的方法,其中所述一种或多种烯键式不饱和化合物具有下式:
其中
R1、R2和R3可以相同或不同并且是氢、卤素或C1-6-烷基,
A是芳基、卤素、CN、C(O)R4、C(O)OR5、OR6、OC(O)R7、NR8C(O)R9或C(O)NR10R11,
其中
R4、R5、R6、R7、R10和R11可以相同或不同并且是氢、C1-100-烷基、C3-8-环烷基、C2-30-烯基、芳基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基、C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2或芳基-C1-30-亚烷基-芳基,且
R8和R9可以相同或不同并具有与R5相同的含义,或与NC(O)一起形成4至7元环,
其中
C1-100-烷基、C1-6-亚烷基-芳基-C1-6-烷基、C1-6-亚烷基-芳基-(C1-6-烷基)2、C1-6-亚烷基-C1-12-环烷基-C1-6-烷基和C1-6-亚烷基-C1-12-环烷基-(C1-6-烷基)2可以是未取代的或被一个或多个C3-8-环烷基、芳基、OC2-30-烯基、卤素、CN、C(O)OR12、C(O)NR13R14、OR15、NR16R17、NHC(O)C(R18)=C(R19)R20、OC(O)C(R21)=C(R22)R23或C(O)OC(R24)=C(R25)R26取代;
C2-30-烯基可以是未取代的或被一个或多个C3-8-环烷基、芳基、卤素、CN、C(O)OR12、C(O)NR13R14、OR15、NR16R17、NHC(O)C(R18)=C(R19)R20、OC(O)C(R21)=C(R22)R23或C(O)OC(R24)=C(R25)R26取代,
芳基或芳基-C1-30-亚烷基-芳基可以是未取代的或被一个或多个C1-6-烷基、C3-8-环烷基、C2-30-烯基、卤素、CN、C(O)OR12、C(O)NR13R14、OR15、NR16R17、NHC(O)C(R18)=C(R19)R20、OC(O)C(R21)=C(R22)R23或C(O)OC(R24)=C(R25)R26取代,其中
R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R25和R26可以相同或不同并且是氢或C1-6-烷基,
且
C1-100-烷基或C2-30-烯基中的一个或多个CH2-基团可以被-O-、-NH-和/或亚苯基替代,且C3-8-环烷基中的一个CH2-基团可以被-O-替代。
3.权利要求1至2任一项的方法,其中所述组合物还包含溶剂。
4.权利要求1至3任一项的方法,其中所述组合物还包含一种或多种自由基引发剂。
5.权利要求1至3任一项的方法,其中所述组合物不含自由基引发剂,条件是所述烯键式不饱和化合物不能是带有烯键式不饱和基团的纳米粒子。
6.权利要求1至5任一项的方法,其中所述组合物还包含一种或多种带有一个或多个烯键式不饱和基团的季铵化合物。
7.权利要求1至6任一项的方法,其中所述组合物还包含其他组分。
8.权利要求1至7任一项的方法,其中将一种或多种杀生物剂在步骤(i)之前、在步骤(i)之后和在步骤(ii)之前、在步骤(ii)之后和在步骤(iii)之前,或在步骤(iii)之后施加在所述基底表面上。
9.权利要求1至8任一项的方法,所述基底用另外的涂层涂布。
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WO2008132037A2 (en) | 2008-11-06 |
CN101679779A (zh) | 2010-03-24 |
JP2010527385A (ja) | 2010-08-12 |
KR20100017293A (ko) | 2010-02-16 |
US8623459B2 (en) | 2014-01-07 |
US20100112364A1 (en) | 2010-05-06 |
WO2008132037A3 (en) | 2009-04-23 |
JP5431304B2 (ja) | 2014-03-05 |
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