CN101970583A - 亲水性涂层 - Google Patents
亲水性涂层 Download PDFInfo
- Publication number
- CN101970583A CN101970583A CN2009801087315A CN200980108731A CN101970583A CN 101970583 A CN101970583 A CN 101970583A CN 2009801087315 A CN2009801087315 A CN 2009801087315A CN 200980108731 A CN200980108731 A CN 200980108731A CN 101970583 A CN101970583 A CN 101970583A
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- Prior art keywords
- coating
- hydrophilic
- poly
- hydrophilic coating
- preparation
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims abstract description 188
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- -1 halo acetophenone derivative Chemical class 0.000 claims description 31
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- 238000009736 wetting Methods 0.000 claims description 27
- 238000012360 testing method Methods 0.000 claims description 24
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 12
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
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Abstract
本发明涉及一种用于制备亲水性涂层的涂料配制品,其中,所述亲水性涂料配制品包含:(a)至少一种多官能可聚合化合物;(b)至少一种Norrish I型光引发剂;和(c)至少一种Norrish II型光引发剂。
Description
本发明涉及一种用于制备亲水性涂层的涂料配制品。本发明还涉及一种亲水性涂层、一种润滑涂层、一种制品、以及一种在基材上形成亲水性涂层的方法。
许多医疗器械,诸如导线、导尿管和心血管导管、注射器和隔膜,需要将润滑剂施加到其外表面和/或内表面上,从而有利于***或拔出体内,和/或有利于液体从体内排出。润滑性质也是需要的,从而使在***或拔出过程中对软组织造成的伤害最小化。尤其,为了润滑目的,上述医疗器械可以具有亲水性表面涂层或层,该表面在润湿时(即在将器械***患者体内之前涂敷润湿液体一段时间)变得润滑且具有低摩擦性质。润湿后变得润滑的涂层或层此后被称为亲水性涂层。润湿后得到的涂层此后被称为润滑涂层(lubricious coating)。
对于多数医疗应用,涂层的强度是最重要的要求之一。为了达到足够的强度,多官能可聚合化合物通常用在涂料配制品中,该化合物在引发剂的存在下在固化时聚合。除了改善强度以外,使用多官能可聚合化合物还可以提供可控的网络,这允许活性物质,例如抗微生物试剂和药物,的调节释放。
本发明人已经发现了一些含有多官能可聚合化合物的涂层具有不好的涂层性质。通常,这种涂层往往在一段时间内降解,特别在水合环境下,这导致可提取物或者可滤取物增加。这种可提取物或可滤取物包括低分子量的和/或聚合型的化合物和/或粒子,它们对于涂层的功能很重要。这种可提取物或可滤取物可以具有例如抗微生物、抗形成血栓、成像、生物活性和/或信号功能。所述涂层的降解通常导致诸如水合能力和维持水合能力损失,光滑性质损失、患者舒适度损失、成像性质损失、由于留在组织表面上的残余物引起的感染风险增大、释放不可控以及生物活性组分的共洗脱问题,并且/或者导致机械强度缺乏,这表现为在摩擦时部分涂层容易从被涂制品上除去。除了降解问题以外,润滑涂层通常易于磨损,同样可以使弯路中(例如血管中)的涂层材料损耗。
因此,本发明的目的在于提供一种具有改善耐磨性的强韧密实的涂层。
现在惊讶地发现,具有改善耐磨性的强韧密实的润滑涂层可以通过使用如下用于制备亲水涂层的涂料配制品获得,其中,所述亲水涂料配制品包含:
(a)至少一种根据式(1)的多官能可聚合化合物:
其中G是具有至少n个官能团的多官能化合物的残基;其中每个R1和每个R2独立地表示氢或选自被取代的和未被取代的可选包含一个或多个杂原子的烃的基团,优选表示氢或C1-C20烃基,更优选表示氢或C1-C20烷基;其中,n是数值至少为2的整数,优选为2-100,更优选为2-8,具体为2或3;
(b)至少一种Norrish I型光引发剂;和
(c)至少一种Norrish II型光引发剂。
已发现,可通过固化本发明的亲水性涂料组合物获得的亲水性涂层与本领域已知的类似涂层相比在弯曲测试(tortuous test)中强韧且耐磨。例如,当使本发明的涂层进行实施例所述的颗粒释放测试(particulate release test)时,发现脱离涂层的颗粒数惊人的低。这对于诸如导线、导管之类的心血管应用特别有利,其中亲水性涂层经受严重弯曲,并且无法忍受颗粒释放。优选的,根据颗粒脱离磨损测试测量的耐磨性相应于小于3000颗、更优选小于2000颗、最优选小于1000颗、具体小于500颗的大于10μm的粒子。
在本发明的上下文中,“润滑”被定义为具有湿滑表面。如果诸如导管的医疗器械的外表面或内表面上的涂层(润湿时)可以***预期身体部位而不会对患者造成伤害和/或使患者不适,那么该涂层被认为是润滑的。具体地,如果在300g的夹持力、1cm/s的牵引速度、22℃的温度的条件下在Harland FTS 5000摩擦测试仪(HFT)上测量的涂层摩擦力为20g或更低,优选为15g或更低,那么该涂层被认为是润滑的。术语“润湿的”是本领域公知的,广义上,意指“含水”。具体地,该术语在本文中被用于描述含有足量的水从而润滑的涂层。就水浓度而言,通常润湿的涂层相对于涂层的干重含有至少10wt%,优选相对于涂层的干重至少50wt%,更优选相对于涂层的干重至少100wt%的水。例如,在本发明的具体实施方式中,约300-500wt%水的吸水量是可行的。润湿液体的实例为:精制水或非精制水、具有例如有机溶剂的含水混合物或含有例如盐、蛋白质或多糖的水性溶液。具体地,润湿液体可以为体液。
Norrish I型和Norrish II型光引发剂b)和c)被用于利用电磁辐射固化本发明的亲水性涂料配制品,例如利用可见光或UV、电子束或γ辐射,从而形成亲水性涂层。本文中,Norrish I型和Norrish II型光引发剂二者都是自由基光引发剂,但其区别在于形成引发自由基的过程。辐射时发色团经历单分子键断裂从而形成引发聚合的自由基的化合物被称为NorrishI型或均裂型光引发剂。Norrish II型光引发剂从适当的协同剂处通过夺氢间接形成自由基,所述协同剂可以是低分子量化合物或聚合物。
如式(1)所示,辐射时发色团经历单分子键断裂的化合物被称为Norrish I型或均裂型光引发剂:
hv
PI →PI* → R1·+·R2 (1)
光引发剂 激发态PI 自由基
根据官能团的性质及其相对于羰基在分子中的位置,断裂可以在邻近羰基的键上发生(α-断裂)、在β-位的键上断裂(β-断裂)或者在远距离位置上的特定弱键(如C-S键或O-O键)处断裂。光引发剂分子中最重要的断裂是,烷基芳基甲酮中的羰基和烷基残基之间的碳碳键的α-断裂,其被称为Norrish I型反应。
如果处于激发态的光引发剂与第二分子(助引发剂COI)相互作用从而如式(2)所示在双分子反应中产生自由基,那么该光引发剂被称为Norrish II型光引发剂。对于Norrish II型光引发剂而言,通常两条主要的反应途径是:激发态引发剂夺氢,或者光诱导电子转移然后裂解。双分子夺氢是激发态二芳基甲酮的典型反应。光诱导电子转移是更一般的过程,其并不局限于某一类化合物。
hv
PI →PI* +COI →R1·+·R2 (2)
光引发剂 激发态PI 自由基
适当的Norrish I型或自由基光引发剂的实例是苯偶姻衍生物、羟甲基苯偶姻和4-苯甲酰基-1,3-二氧杂戊环衍生物、苄基缩酮(benzilketal)、α,α-二烷氧基苯乙酮、α-羟基烷基苯甲酮(α-hydroxy alkylphenones)、α-氨基烷基苯甲酮、酰基氧化膦、二酰基氧化膦、酰基硫化膦、卤代苯乙酮衍生物等等。适当I型光引发剂的商品实例是Irgacure 2959(2-羟基-4’-(2-羟基乙氧基)-2-甲基苯基乙基甲酮),Irgacure 651(苄基二甲基缩酮或2,2-二甲氧基-1,2-二苯基乙酮,Ciba-Geigy),Irgacure 184(1-羟基-环己基-苯基甲酮作为活性组分,Ciba-Geigy),Darocur 1173(2-羟基-2-甲基-1-苯基丙-1-酮作为活性组分,Ciba-Geigy),Irgacure 907(2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙-1-酮,Ciba-Geigy),Irgacure 369(2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁-1-酮作为活性组分,Ciba-Geigy),Esacure KIP 150(聚{2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙-1-酮},Fratelli Lamberti),Esacure KIP100 F(聚{2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙-1-酮}和2-羟基-2-甲基-1-苯基-丙-1-酮的共混物,Fratelli Lamberti),Esacure KTO 46(聚{2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙-1-酮},2,4,6-三甲基苯甲酰基二苯基氧化膦和甲基二苯甲酮衍生物的共混物,Fratelli Lamberti),诸如Lucirin TPO(2,4,6-三甲基苯甲酰基二苯基氧化膦,BASF)、Irgacure 819(二(2,4,6-三甲基苯甲酰基)-苯基氧化膦,Ciba-Geigy)、Irgacure 1700(二(2,6-二甲氧基苯甲酰基)2,4,4-三甲基苯基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮的25∶75%共混物,Ciba-Geigy)的酰基氧化膦,等等。还可以使用I型光引发剂的混合物。
可用在本发明的亲水性涂料配制品中的Norrish II型光引发剂的实例包括芳族酮,诸如二苯甲酮、呫吨酮、二苯甲酮的衍生物(例如氯二苯甲酮)、二苯甲酮和二苯甲酮衍生物的共混物(例如Photocure 81,4-甲基-二苯甲酮与二苯甲酮的50/50共混物)、米蚩酮、乙基米蚩酮、噻吨酮和其它呫吨酮衍生物(诸如Quantacure ITX,异丙基噻吨酮)、苯偶酰、蒽醌(例如2-乙基蒽醌)、香豆素或者这些光引发剂的化学衍生物或组合。
优选的Norrish I型和Norrish II型光引发剂是水溶性的或者可被调节成水溶性的,还要优选的光引发剂是聚合光引发剂或可聚合光引发剂。
一般而言,光引发剂在亲水性涂料配制品中的总量基于干涂层的总重介于0.2和10wt%之间,优选介于0.8和8wt%之间。
此后,本申请中所有组分的百分率都是基于干涂层的总重,即固化亲水性涂料配制品后形成的亲水性涂层的总重。
典型地,Norrish I型光引发剂与Norrish II型光引发剂的重量比介于10∶1和1∶10之间,介于7∶1和1∶7之间或介于5∶1和1∶5之间。
多官能可聚合化合物(a)的用量相对于干燥涂层的总重可以大于0%,例如大于1%,或大于2%。多官能可聚合化合物在涂料配制品中的含量基于干燥涂层的总重可以高达100%、90%、80%、70%、60%或50%。本领域普通技术人员可以在上述范围内变化多官能可聚合化合物的含量以获得对其应用所需的性质。
通常,多官能可聚合化合物(a)具有500g/mol或更高、优选750g/mol或更高、更优选1000g/mol或更高的数均分子量(Mn)。通常,多官能可聚合化合物(a)具有100000g/mol或更低、优选10000g/mol或更低、更优选6000g/mol或更低、具体2000g/mol或更低的数均分子量(Mn)。具有优选范围内的Mn的多官能可聚合化合物表现出有利的交联密度,即具有足以为官能组分提供空间的开阔度和足以提供足够机械强韧性的致密度。
除了以上定义的多官能(即n≥2)可聚合化合物(a)以外,组合物还可以包含根据式(1)(其中n=1)的物种,即仅含有一个反应性片段的分子。这些单官能分子也成为在固化后形成的网络的一部分。每个式(1)分子中反应性片段的平均数优选在约1.2至约64的范围内,更优选在约1.2至约16的范围内,最优选在约1.2至约8的范围内。
在本发明的一个实施方式中,多官能可聚合化合物(a)可溶于极性溶剂中。在本发明的上下文中,这意味着根据这个实施方式至少1g、优选至少3g、更优选至少5g、具体至少10g的多官能可聚合物化合物(a)可以溶解在100g 25℃的极性溶剂中。适当的极性溶剂的实例包括水和C1-C6醇、具体为甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
在本发明的一个实施方式中,G包括至少一个含有杂原子的片段。在本发明的上下文中,杂原子被理解为非碳、非氢原子。适当杂原子的实例包括氧原子(O)、氮原子(N)、硫原子(S)和磷原子(P)。
在本发明的一个实施方式中,G是亲水性多官能化合物的残基,所述亲水性多官能化合物优选选自由聚醚、聚酯、聚氨酯、聚环氧化物、聚酰胺、聚(甲基)丙烯酰胺、聚(甲基)丙烯酸类、聚噁唑烷酮、聚乙烯醇、聚乙烯亚胺、多肽和多糖(诸如纤维素或淀粉)或上述的任意组合组成的组,更优选为包含至少一个聚乙二醇或聚丙二醇嵌段的聚合物。如果需要涂层具有亲水性和/或润滑特性,那么使用亲水性多官能化合物特别有利。
在式(1)的多官能可聚合化合物(a)中,R1优选表示氢、CH3或CH2OH。特别适宜的是其中R1和R2都表示氢或者其中R1表示CH3且R2表示氢的多官能可聚合化合物。
适当的本发明的多官能可聚合化合物的实例是聚醚基(甲基)丙烯酰胺,例如聚乙二醇二丙烯酰胺和聚乙二醇二甲基丙烯酰胺。可用于生产多官能(甲基)丙烯酰胺多官能可聚合化合物的可商购聚醚多官能胺包括双(3-氨基丙基)封端的聚(乙二醇),Mw=1500(Aldrich);PEG二胺(纯氧化乙烯单元)P2AM-2(分子量2K)、P2AM-3(3.4K)、P2AM-6(6K)、P2AM-8(8K)和P2AM-10(10K)(Sunbio),D-230聚醚胺、D-400聚醚胺、D-2000、D-4000、XTJ-500(ED-600)、XTJ D501(ED-900)、XTJ-502(ED-2003)、XTJ-590二胺、XTJ-542二胺、XTJ-548二胺、XTJ-559二胺、XTJ-556二胺、SD-231(XTJ584)、SD401(XTJ-585)、T-403聚醚胺、XTJ-509聚氧丙烯三胺、T-5000聚醚胺和ST-404聚醚胺(XTJ-586)。
在本发明的上下文中,术语“聚合物”是指含有两个或多个重复单元的分子。具体地,聚合物可以由两个或多个相同或不同的单体形成。当用于本文时,该术语包括低聚物或预聚物。通常,聚合物的数均分子量(Mn)为约500g/mol或更高,具体为约1000g/mol或更高,但是在聚合物由相对小的单体单元组成的情况下,Mn可以更低。此处和此后,Mn被定义为通过光散射(可选与尺寸排斥色谱SEC组合)测定的Mn。
在本发明的一个实施方式中,亲水涂料配制品还包含非离子亲水性聚合物。本文中,非离子亲水性聚合物被理解为由包含如下构成单元的大分子构成的高分子量线性的、支化的或交联的聚合物,其中,当亲水聚合物存在于润滑涂层中时小于5%的所述构成单元包含离子化的基团。
亲水性聚合物能够为涂层提供亲水性,其可以是合成的或生物衍生的,还可以是以上两种的共混物或共聚物。亲水性聚合物包括但不限于聚(内酰胺)(例如聚乙烯基吡咯烷酮(PVP))、聚氨酯、丙烯酸和甲基丙烯酸的均聚物和共聚物、聚乙烯醇、聚乙烯醚、马来酸酐基共聚物、聚酯、乙烯基胺、聚乙烯亚胺、聚环氧乙烷、聚(羧酸)、聚酰胺、聚酸酐、聚磷嗪(polyphosphazene)、纤维素类(例如甲基纤维素、羧甲基纤维素、羟甲基纤维素和羟丙基纤维素)、肝磷脂、右旋糖苷、多肽(例如胶原质、纤维蛋白和弹性蛋白)、多糖(例如壳聚糖、透明质酸、海藻酸、明胶和壳多糖)、聚酯(例如聚丙交酯、聚乙交酯和聚己内酯)、多肽(例如胶原质、白蛋白、寡肽、多肽、短链肽、蛋白质和寡聚核苷)。
通常,亲水性聚合物具有在约8000至约5000000g/mol范围内、优选在约20000至约3000000g/mol范围内、更优选在约200000至约2000000g/mol范围内的分子量。
在本发明的一个实施方式中,亲水性聚合物的用量相对于干燥涂层的总重大于1wt%,例如大于5wt%或大于50wt%。亲水性聚合物的用量基于干燥涂层的总重可以高达99wt%,或高达95wt%。
本发明的亲水涂料配制品还可以包含聚电解质。在本文中,聚电解质被理解为:由含有多个构成单元的大分子组成的高分子量线性、支化或交联聚合物,其中,当所述聚电解质用在润滑涂层中时,5至100%的所述构成单元包含离子化基团。本文中,构成单元例如被理解为重复单元,例如单体。聚电解质在本文中可以指由一种类型的大分子组成的一种类型的聚电解质,也可以指由不同类型的大分子组成的两种或多种不同类型的聚电解质。
聚电解质的使用被认为改善亲水性涂层的润湿性和变干时间。在本文中,变干时间为:在将含有亲水性涂层的器械从所述亲水性涂料在其中被储存和/或润湿的润湿液体中取出后,所述亲水性涂层保持润滑的持续时间。具有改善变干时间的亲水性涂层(其中亲水性涂层保持润滑的持续时间延长)在***体内以前或者在体内与例如黏膜或血管接触时失水、变干的趋势降低了。在含有润滑涂层的器械***体内或从体内取出的时候,失水和变干可能导致并发症。变干时间可以通过如下测定:在HFT上测量暴露于空气中的导管的摩擦力(以克计)与时间的函数关系。
当选择合适的聚电解质时,应当考虑其在水性介质中的溶解性和粘度、其分子量、其电荷密度、其与涂层的支撑网络的亲合性以及其生物相容性。本文中,生物相容性意指,在活哺乳动物组织中不会产生有毒、有害或免疫响应的生物相容性。
为了减少迁移性,聚电解质优选是重均分子量至少为约1000g/mol的聚合物,所述重均分子量通过光散射(可选与尺寸排除色谱组合)测定。为了延长变干时间和/或减少迁移出涂层,优选相对高分子量的聚电解质。聚电解质的重均分子量优选为至少20,000g/mol,更优选为至少100,000g/mol,甚至更优选为至少约150,000g/mol,具体为约200,000g/mol或更高。为了易于施加所述涂层,优选的平均重量为1,000,000g/mol或更低,具体为500,000g/mol或更低,更具体为300,000g/mol或更低。
可存在于聚电解质中的离子化基团的实例为:铵基、磷鎓基、硫鎓基、羧酸盐基、硫酸盐基、亚磺基、磺基、磷酸盐基和膦基。上述基团在键合水时非常有效。在本发明的一个实施方式中,所用聚电解质还包含金属离子。金属离子,当溶于水中时,与水分子络合,从而形成水合离子[M(H2O)x]n+,其中,x是配位数,n是金属离子的电荷,因此所述金属离子在键合水时特别有效。可存在于聚电解质中的金属离子例如为:碱金属离子,诸如Na+、Li+或K+;或碱土金属离子,诸如Ca2+和Mg2+。具体地,当聚电解质包括季胺盐(例如季铵基团)时,可以存在阴离子。所述阴离子例如可以为:卤离子,诸如Cl-、Br-、I-和F-,还可以为硫酸根、硝酸根、碳酸根和磷酸根。
合适的聚电解质例如为:丙烯酸的均聚物和共聚物的盐、甲基丙烯酸的均聚物和共聚物的盐、马来酸的均聚物和共聚物的盐、富马酸的均聚物和共聚物的盐、含有磺酸基团的单体的均聚物和共聚物的盐、含有季铵盐的单体的均聚物和共聚物及其混合物和/或衍生物。合适的聚电解质的实例为:聚(丙烯酰胺-共-丙烯酸)盐,例如聚(丙烯酰胺-共-丙烯酸)钠盐;聚(丙烯酰胺-共-甲基丙烯酸)盐,例如聚(丙烯酰胺-共-甲基丙烯酸)钠盐;聚(甲基丙烯酰胺-共-丙烯酸)盐,例如聚(甲基丙烯酰胺-共-丙烯酸)钠盐;聚(甲基丙烯酰胺-共-甲基丙烯酸)盐,例如聚(甲基丙烯酰胺-共-甲基丙烯酸)钠盐;聚(丙烯酸)盐,例如聚(丙烯酸)钠盐;聚(甲基丙烯酸)盐,例如聚(甲基丙烯酸)钠盐;聚(丙烯酸-共-马来酸)盐,例如聚(丙烯酸-共-马来酸)钠盐;聚(甲基丙烯酸-共-马来酸)盐,例如聚(甲基丙烯酸-共-马来酸)钠盐;聚(丙烯酰胺-共-马来酸)盐,例如聚(丙烯酰胺-共-马来酸)钠盐;聚(甲基丙烯酰胺-共-马来酸)盐,例如聚(甲基丙烯酰胺-共-马来酸)钠盐;聚(丙烯酰氨基-2-甲基-1-丙烷磺酸)盐;聚(4-苯乙烯磺酸)盐;聚(丙烯酰胺-共-二烷基氯化铵);季铵化聚[二-(2-氯乙基)醚-交替-1,3-二[3-(二甲氨基)丙基]脲];聚磷酸烯丙基铵;聚(二烯丙基二甲基氯化铵);聚(三亚甲基氧亚乙基磺酸钠);聚(二甲基十二烷基(2-丙烯酰氨基乙基)溴化铵);聚(2-N-甲基吡啶鎓亚乙基碘);聚乙烯基磺酸以及聚(乙烯基)吡啶、聚乙烯亚胺和聚赖氨酸的盐。
特别适于用在本发明中的聚电解质为共聚聚电解质,该共聚聚电解质可以是无规共聚物或嵌段共聚物,其中,所述共聚聚电解质是含有至少两种不同类型构成单元的共聚物,其中,至少一种类型的构成单元包含可离子化或离子化基团,至少一种类型的构成单元没有可离子化基团或离子化基团。可离子化被理解为在中性水溶液(例如pH为6-8的溶液)中可离子化。这种共聚聚电解质的实例是聚(丙烯酰胺-共-丙烯酸)盐。
在发明的一个实施方式中,亲水性涂料组合物相对于干涂层的总重包含0-90wt%%或10-20wt%的聚电解质。
在亲水涂料配制品中,亲水性聚合物和聚电解质(如果存在)的总重量与多官能可聚合化合物的重量比例如可以介于1∶99至99∶1之间,诸如介于5∶95至95∶5之间,或50∶50至95∶5之间。
本发明涉及含有一种亲水性涂料配制品,当所述涂料配制品被涂敷到基材上并固化时得到亲水性涂层。本文中,亲水性涂料配制品指:液体亲水性涂料配制品,例如含有液体介质的溶液或悬浮液。本文中,允许在表面上涂敷亲水性涂料配制品的任何液体介质都是满足需要的。液体介质的实例是:醇(如甲醇、乙醇、丙醇、丁醇或其异构体和水性混合物)、丙酮、甲基乙基甲酮、四氢呋喃、二氯甲烷、甲苯或其水性混合物或乳液或水。亲水性涂料配制品进一步包括各种组分,这些组分当固化时转化成亲水性涂层,从而在固化后保留在亲水性涂层中。本文中固化被理解为:通过例如加热、冷却、干燥、结晶的任何方法造成物理或化学硬化或凝固,或由化学反应造成的固化,例如辐射固化或热固化。处于固化状态时,亲水性涂料配制品中的所有组分或部分组分可以通过使用UV辐射或电子束辐射进行交联,从而在所有组分之间或部分组分之间形成共价联接。然而,处于固化状态时,所有组分或部分组分还可以是离子键合的,通过偶极-偶极相互作用键合或者通过范德华力或氢键键合。
术语“固化”包括处理配制品从而使其形成坚固涂层的任何方式。具体地,该术语包括如下处理方式,其中亲水性聚合物进一步聚合,被提供接枝从而所述亲水性聚合物形成接枝聚合物,和/或被交联从而所述亲水性聚合物形成交联聚合物。
本发明还涉及一种亲水性涂层,所述涂层可通过将本发明的亲水性涂料配制品涂敷到基材上并使其固化得到。本发明还涉及一种润滑涂层,所述涂层可通过将润湿液体施加在所述亲水性涂层上得到。而且本发明涉及一种制品,具体涉及一种含有至少一层本发明亲水性涂层的医疗器械或医疗器械构件,并且涉及一种在基材上形成本发明亲水性涂层的方法。
亲水性涂层包含支撑网络。所述亲水性涂层通过使含有多官能可聚合化合物、Norrish I型光引发剂和Norrish II型光引发剂的亲水性涂料配制品固化来形成。如果存在亲水性聚合物和/或聚电解质,那么它们在固化后还可以共价键合和/或物理结合到其它组分的一个或多个上和/或缠绕形成聚合物网络。
多官能可聚合化合物、可选亲水性聚合物和/或聚电解质在亲水性涂层中共价键合和/或物理结合作为聚合物网络一部分,具有如下优点,例如在亲水性涂层覆盖在医疗器械上时,它们(如果存在)不会漏到所述亲水性涂层的环境中。当所述医疗器械处于人体或动物体内时,这点特别有益。
在本发明的一个实施方式中,根据本发明的亲水性涂料配制品进一步包含至少一种表面活性剂,所述表面活性剂可以改善涂层的表面性质。表面活性剂是去污组分中最重要的部分。一般而言,它们是可水溶表面活性剂,其由连接到亲水性官能团或水溶解性增强官能团上的疏水部分(通常是长烷基链)组成。根据存在于分子(在水溶液中解离后)的亲水性部分中的电荷,表面活性剂可被分类为:离子表面活性剂,例如阴离子表面活性剂或阳离子表面活性剂,和非离子表面活性剂。离子表面活性剂的实例包括,十二烷基硫酸钠(SDS)、胆酸钠、二(2-乙基己基)硫代琥珀酸钠盐、十六烷基三甲基溴化铵(CTAB)、十二烷基二甲基氧化胺(LDAO)、N-月桂酰基肌氨酸钠盐和脱氧胆酸钠(DOC)。非离子表面活性剂的实例包括,烷基聚葡萄糖苷(诸如TRITONTM BG-10表面活性剂和TRITON CG-110表面活性剂)、支化仲醇乙氧化物(诸如TERGITOLTM TMN系列)、环氧乙烷/环氧丙烷共聚物(诸如TERGITOL L系列、TERGITOL XD、XH和XJ表面活性剂)、壬基酚乙氧化物(诸如TERGITOL NP系列)、辛基酚乙氧化物(诸如TRITON X系列)、仲醇乙氧化物(诸如TERGITOL 15-S系列)和特殊烷氧化物(诸如TRITON CA表面活性剂、TRITON N-57表面活性剂、TRITON X-207表面活性剂、Tween 80和Tween 20)。
在上述实施方式中,基于干涂层的总重,通常应用0.001至1wt%的表面活性剂,优选应用0.05-0.5wt%。
在本发明的一个实施方式中,根据本发明的亲水性涂料配制品进一步包括至少一种增塑剂,其可以增加涂层的柔性,待涂敷的物品在使用过程中可能弯曲时优选含有增塑剂。包含在亲水性涂料配制品中的所述增塑剂的浓度,相对于干涂层的总重,为约0.01wt%至约15wt%,优选为约1wt%至约5.0wt%。合适的增塑剂是高沸点化合物,优选的化合物在环境压力下具有>200℃的沸点,并且具有均匀溶解和/或分散在固化涂层中的趋势。合适的增塑剂的实例为,单醇和多醇和聚醚,诸如正癸醇、丙三醇、乙二醇、二乙二醇、聚乙二醇和/或与丙二醇和/或脂肪酸的共聚物。
根据本发明的亲水性涂层可以涂敷在制品上。亲水性涂层可以涂敷在基材上,所述基材可以选自具有各种几何形状和材料的基材。所述基材可以具有如下纹理,诸如多孔、无孔、平滑、粗糙、平坦、不平坦。基材支撑其表面上的亲水性涂层。亲水性涂层可以在基材的所有区域上或在选择区域上。亲水性涂层可以应用到各种物质形式上,包括薄膜、片材、棒、管、模制部件(规则形状或不规则形状)、纤维、织物和颗粒。适于用在本发明中的表面是提供如下所需性质的表面,所需性质诸如为,多孔性、疏水性、亲水性、着色性(colorisability)、强度、柔性、渗透性、伸长率、耐磨性和抗撕扯性。合适表面的实例例如为如下表面,其由金属、塑料、陶瓷、玻璃和/或复合物组成或包含金属、塑料、陶瓷、玻璃和/或复合物。亲水性涂层可以直接施加到所述表面上,或者可以施加到经预处理或被涂敷的表面上,其中所述预处理的目的在于,有助于亲水性涂层粘合到基材上。
在本发明的一个实施方式中,根据本发明的亲水性涂层涂敷到生物医学基材上。生物医学基材部分涉及医学领域以及活细胞和体系的研究。这些领域包括诊断、治疗、和实验人医学、兽医学和农业。医学领域的实例包括眼科学、整型外科和假体学、免疫学、皮肤医学、药理学和外科学;研究领域的非限制性实例包括细胞生物学、微生物学和化学。术语“生物医学”还涉及化学品和化学品的组合物,而不管这些化学品的来源,这些化学品(i)调节体内生物反应;(ii)在体外实验或其它模型(例如免疫学或药理学试验)中具有活性,或者(iii)可以在细胞或有机体内找到。术语“生物医学”还涉及分离科学,诸如涉及色谱、渗透、反向渗透和过滤过程的科学。生物医学制品的实例包括研究工具、工业和消费用具。生物医学制品包括分离制品、可植入制品和眼科制品。眼科制品包括软质和硬质接触镜、眼内晶状体以及镊子、牵引器或其它接触眼睛或周围组织的手术工具。优选的生物医学制品是,由具有高透氧性的含硅水凝胶聚合物制成的软质接触镜。分离制品包括过滤器、渗透膜和反向渗透膜、透析膜以及诸如人造皮肤和其它隔膜的生物表面。可植入制品包括导管以及人造骨骼、关节或软骨的片段。制品可以属于一个以上的范畴,例如,人造皮肤是多孔、生物医学制品。细胞培养制品的实例为玻璃烧杯、塑料陪替氏培养皿和其它用在组织细胞培养和细胞组织过程中的器具。细胞培养制品中的优选实例是生物反应器微量载体、用在固定细胞生物反应器中的硅酮聚合物基质,其中,可以控制微粒微量载体的几何形状、多孔性和密度,从而使性能最优化。理想的是,微量载体耐化学降解或生物降解,耐高冲击应力、耐机械应力(搅动)并且耐重复蒸汽或化学品消毒。除了硅酮聚合物以外,其它材料也是合适的。本发明也可以用在食品工业中、纸张印刷工业中、病号服中、尿布和其它衬垫中以及需要亲水性、可润湿或毛细制品(wicking article)的其它领域中。
医疗器械可以为可植入器械或体外器械。该器械可以短期暂时使用,或者长期永久性植入。在某些实施方式中,合适的器械是那些通常用于为心律失调、心力衰竭、瓣膜性疾病、血管病、糖尿病、神经疾病和失调症、整型外科、神经外科、肿瘤学、眼科学和ENT手术提供医疗和/或诊断的器械。
医疗器械的合适实例包括,但不限于,支架、支架移植物、吻合连接器、合成贴片、引线、电极、针、导线、导管、传感器、手术仪器、血管成形球、创口引流管、分流管(shunt)、管子、输液套简(infusion sleeve)、尿道插管、小球、植入物、血液充氧发生器、泵、脉管移植物、埋入式介入药盒(vascular access port)、心瓣膜、瓣环成形术环、缝合线、手术夹、手术钉、起博器、可植入去纤颤器、神经刺激器、整型外科器械、脑脊髓液分流管、可植入药泵、椎笼、人造椎间盘、髓核的替代器械、耳管、眼内晶状体和在微创手术中使用的任何管。
特别适于用在本发明中的制品包括医疗器械或构件,诸如导管(例如间歇性导管、球囊导管、PTCP导管、支架输送导管)、导线、支架、注射器、金属和塑料植入物、接触镜和医用管。
亲水性涂料配制品可以通过例如浸涂涂敷到基材上。涂敷的其它方法包括喷涂、洗涤、气相沉淀、刷涂、辊涂和其它本领域已知的方法。
根据本发明的亲水性涂层的厚度可以通过如下方法控制:改变浸泡时间、改变牵引速率或改变亲水性涂料配制品的粘度和涂敷步骤的次数。通常,亲水性涂层在基材上的厚度在0.1-300μm的范围内,优选在0.5-100μm的范围内,更优选在1-30μm的范围内。
本发明进一步涉及一种在基材上形成亲水性涂层的方法,所述涂层当被水基液体润湿时具有低摩擦系数。
为了将亲水性涂层涂敷到基材上,可以使用初级涂层,从而在亲水性涂层和基材之间提供粘合物。初级涂层通常被称为底层,基层或粘结层。所述初级涂层是有利于亲水性涂层粘着到给定基材上的涂层,如在例如WO02/10059中所述。初级涂层和亲水性涂层之间可以由于共价键合或离子键合、氢键、物理吸附或聚合物缠结而发生粘合。这些初级涂层可以基于溶剂、基于水(乳胶或乳液)或没有溶剂,并且可以包含线性、支化和/或交联组分。可用的典型初级涂层例如包括聚醚砜、聚氨酯、聚酯(包括聚丙烯酸酯,如在例如US6,287,285中所述的)、聚酰胺、聚醚、聚烯烃和上述聚合物的共聚物。
具体地,初级涂层包括支撑聚合物网络,所述支撑网络可选包含缠结在支撑聚合物网络中的官能性亲水性聚合物,如WO06/056482 A1中所述。现通过引用将关于初级涂层的配制的信息包含于此。
上述初级层特别适于改善包含亲水性聚合物(诸如聚内酰胺,具体为PVP)和/或上述的亲水性聚合物中的另一种的涂层特别是在聚氯乙烯(PVC)、硅酮、聚酰胺、聚酯、聚烯烃(诸如聚乙烯、聚丙烯和乙烯-丙烯橡胶(例如EPDM))或具有大致相同或更低亲水性的表面上的粘合性。
一般而言,对初级涂层的厚度没有限制,但厚度通常小于5μm、小于2μm或小于1μm。
在实施方式中,对制品的表面进行氧化表面处理、光氧化表面处理和/或极化表面处理,例如进行等离子体和/或电晕处理,从而改善待提供涂层的粘合性。合适的条件是本领域公知的。
可以以任何方式来涂敷本发明的配制品。固化条件可以根据光引发剂和聚合物的已知固化条件来确定或者通过常规实验来确定。
优选地,可以通过如下在基材上形成亲水涂层:
-将本发明的涂料配制品涂覆到所述基材的至少一个表面上;并且
-通过将所述配制品暴露于电磁辐射从而激发所述引发剂来使所述涂料配制品固化。
一般而言,固化可以在任何合适的温度下来实施,这依赖于基材,前提条件是:制品的机械性质或其它性质不会受到不可接受程度上的不利影响。
根据光引发剂的选择,可以常规选择电磁辐射的强度和波长。具体地,可以使用光谱的UV部分、可见部分或IR部分中的合适波长。
本发明通过以下实施例进一步阐明。
实施例
如下制备初级涂料配制品。
初级涂料配制品(实施例1和对比例A-B)
PTGL1000(T-H)2* 5.00%(w/w)
Irgacure 2959(Aldrich) 0.20%(w/w)
乙醇(Merck,96%额外纯PH EUR,BP) 94.8%(w/w)
*如下合成
将上述组分加入棕色玻璃烧瓶中,然后在室温下搅拌整夜(~16小时)。第二天早上,初级配制品是粘度为7mPa.s的均匀液体。本文中,粘度在Brookfield CAP 1000,v.1.2上结合1号锥体在25℃下测定。
表1.初级涂料配制品的涂敷条件
初级涂料配制品 | |
初级涂层固含量[w/w%] | 5 |
粘度[mPa.s] | 7 |
初级涂层牵引速度[cm/s] | 1.0 |
初级涂层固化时间[s] | 15 |
PTGL 1000(T-H)
2
的合成
在干燥的惰性气氛中,将甲苯二异氰酸酯(TDI或T,Aldrich,纯度95%,87.1g,0.5mol)、Irganox 1035(Ciba Specialty Chemicals,0.58g,相对于丙烯酸羟乙基酯(HEA或H)为1wt%)和2-乙基己酸锡(II)(Sigma,纯度95%,0.2g,0.5mol)置于1升烧瓶中并搅拌30分钟。利用冰浴将反应混合物冷却至0℃。在30分钟内滴加HEA(Aldrich,纯度96%,58.1g,0.5mol),此后除去冰浴,使得混合物温热至室温。3小时后,反应完全。在30分钟内滴加聚(2-甲基-1,4-丁二醇)-交替-聚(四亚甲基二醇)(PTGL,Hodogaya,Mn=1000g/mol,250g,0.25mol)。随后,将反应混合物加热至60℃,并搅拌18小时,此时GPC(表明HEA被完全消耗了)、IR(表明没有与NCO相关的谱带)和NCO滴定(NCO含量低于0.02wt%)表明该反应完全了。
实施例1
制备含有式(1)多官能可聚合化合物(a)、Norrish I型光引发剂(b)(Irgacure 2959)和Norrish II型光引发剂(c)(二苯甲酮)的亲水性涂料配制品。
PEG1500二丙烯酰胺* 2.00wt%
聚乙烯吡咯烷酮(PVP,1.3M,Aldrich) 1.33wt%
PAcA 0.67wt%
二苯甲酮(Aldrich) 0.08wt%
Irgacure 2959 0.04wt%
Tween 80(表面活性剂,Merck) 0.04wt%
水 47.92wt%
MeOH(Merck pa) 47.92wt%
*如下合成
对比例A
为了比较,制备不含Norrish II型光引发剂的亲水性涂料配制品A。
PEG1500二丙烯酰胺** 2.00wt%
PVP 1.3M 1.33wt%
PAcA 0.67wt%
二苯甲酮 -
Irgacure 2959 0.04wt%
Tween 80 0.04wt%
水 47.96wt%
MeOH(Merck pa) 47.96wt%
**如下合成
对比例B
制备不含Norrish II型光引发剂(c)且含有与式(1)不同的多官能可聚合化合物的对比例B的涂料配制品。
PEGDA* 2.00wt%
PVP 1.3M 1.33 wt%
PAcA 0.67wt%
二苯甲酮
Irgacure 2959 0.04wt%
Tween 80 0.04wt%
水 47.92wt%
MeOH 47.92wt%
*如下合成
将实施例1以及对比例A和B的上述组分加入棕色玻璃烧瓶中,然后在室温下搅拌整夜(~16小时)。第二天早上,初级配制品是粘度如表2所示的均匀液体。本文中,粘度在Brookfield CAP 1000,v.1.2上结合1号锥体在25℃下测定。
PEG1500二丙烯酰胺的合成
在氮气下,将20g(13.3mmol)双(3-氨基丙基)封端的聚乙二醇(PEG1500-二胺,Mn=1500g/mol,Aldrich,34901-14-9)在400mL甲苯中共沸蒸馏,除去约100mL甲苯。将溶液在氮气氛、室温下冷却,然后在冰浴中冷却。添加50mL的二氯甲烷(Merck)。先后滴加4.04g(39.7mmol)的三乙胺和3.48g(39.7mmol)的丙烯酰氯(直接使用未进行进一步纯化)。该反应在氮气下进行整夜。将溶液在冰浴中冷却从而沉淀出NEt3-HCl盐,然后进行过滤。在添加1%(w/w)Irganox 1035,真空浓缩滤液。将浓缩液重新溶于75mL的二氯甲烷中,然后在1.5L冰冷的二***中沉淀。通过过滤收集产物,随后用二***对其进行洗涤。
1H-NMR(CDCl3,22℃)δ(TMS)=6.7ppm(2H,-NH-);6.2 & 6.1ppm(4H,CH2=CH-);5.6ppm(2H,CH2=CH-);3.6ppm(164H,-O-CH2-CH2-and-O-CH2-CH2-CH2-);1.8ppm(4H,-O-CH2-CH2-CH2-)。
NMR光谱确认形成了PEG1500二丙烯酰胺。分别对在6.2、6.1ppm和在1.8ppm的NMR峰进行积分,估计约99%的PEG-二胺都转化成PEG1500二丙烯酰胺。
IR光谱确认形成了PEG1500二丙烯酰胺。
PEG4000DA的合成
在45℃的氮气氛下,将150g(75mmol OH)的聚乙二醇(PEG,来自Fluka的Biochemika Ultra,OH值28.02mg KOH/g,499.5mew/kg,Mn=4004g/mol)溶于350ml无水甲苯中。加入0.2g(0.15wt%)Irganox1035作为自由基稳定剂。将所得溶液共沸蒸馏整夜(50℃,70mbar),将冷凝甲苯引导到分子筛上。对于每批PEG,通过OH滴定精确测定OH值,根据在the European Pharmacopoeia第四版,105页,2.5.3节,“羟值”中描述的方法进行上述测定。这可以计算待加丙烯酰氯的量并且可以确定反应过程中的丙烯酸酯的酯化度。将9.1g(90mmol)的三乙胺加入反应混合物中,接着在1小时内滴加溶于50ml甲苯中的8.15g(90mmol)丙烯酰氯。三乙胺和丙烯酰氯是无色液体。将反应混合物在45℃、氮气氛下搅拌2至4小时。反应过程中,将温度保持在45℃,从而防止PEG结晶。为了测定转化率,将样品从反应混合物中取出、干燥并溶于氘代氯仿中。加入三氟乙酸酐(TFAA)并记录1H-NMR光谱。TFAA与剩余的羟基反应,从而形成三氟乙酸酯,这可以利用1H-NMR光谱容易地测定(可以清楚地区分三氟乙酸α-位的亚甲基质子的三重信号峰(g,4.45ppm)和丙烯酸酯α-位的亚甲基质子的信号峰(d,4.3ppm))。当丙烯酸酯的酯化度为98%时,将额外的10mmol丙烯酰氯和三乙胺加入反应混合物中,使反应混合物反应1小时。在丙烯酸酯的酯化度>98%时,将温热的溶液过滤,从而除去三乙胺盐酸盐。在真空下(50℃,20mbar)除去约300ml甲苯。将剩余的溶液保持在45℃的热滴液漏斗中,并滴加到1升二***(在冰浴中冷却)中。将醚悬浮液冷却1小时,然后通过过滤得到PEG二丙烯酸酯产物。将该产物在室温下、减压空气气氛(300mbar)中干燥整夜。得到白色晶体状产物,收率:80-90%。
表2.实施例1、对比例A和B的亲水性涂料配制品的涂敷条件
1 | A | |
顶涂层固含量[w/w%] | 4 | 4 |
粘度[mPa.s] | 23 | 24 |
顶涂层牵引速度[cm/s] | 1.0 | 1.0 |
顶涂层固化时间[s] | 360 | 360 |
对于初级涂层和亲水性涂层而言,Pebax导管轴的被涂敷长度为27cm。
Harland PCX涂布机中介于250-400nm之间的UV光强度平均为60mW/cm2,这利用安装有探测器SED005#989和滤光器WBS320#27794的Harland UVR335(1L 1400)光度仪测量。初级涂层曝光15秒,顶部涂层暴露于UV光下360秒。这相当于UV剂量分别为0.9J/cm2和21.6J/cm2。涂敷期间,温度为21℃,RH为50%。对于所应用的涂敷参数参见表3。
表3.PCX涂布仪上所应用的工艺参数
在如下所述颗粒释放测试中对被涂敷的导管轴进行测试。
颗粒释放测试用样品的制备
称重10g Congo-红,然后将其溶解在处于测量烧瓶中的1L milli-Q纯化水中。使用所得1wt%的Congo红溶液对被涂敷PebaxTM导管轴上的亲水性涂层进行染色。将被涂敷导管轴浸渍在该溶液中30分钟。将被涂敷的导管轴在空气中干燥15分钟。再次在纯水中润湿,从而除去过量Congo红。现在,将被涂敷的导管轴再次在空气中干燥至其不发粘(约1小时)。对被Congo红着色的经涂敷导管轴进行以下所述磨损测试。
颗粒释放磨损测试
在带有10 N KAP-Z载荷传感器的Zwick 1474 ZmartPro拉伸测试仪(此后被称为“Zwick拉伸测试仪”,见图1)上进行颗粒释放磨损测试。使用如下材料和装置:
-950mm的0.022”(0.56mm)Nitinol SE金属导线(直径0.0022”,New England Precision Grinding)作为每个被涂敷导管轴内的增强芯线。
-625mm的Medtronic Pro-Flo 6F 2.00mm,110cm猪尾形血管造影导管(此后被称为“Pro-Flo引导导管”或在图1中为“Pro-Flo引导导管”)作为摩损测试用外部相对表面。近端上的连接器用于连接注射器。
-60ml的Milli-Q水
-150mm的如上所述被涂敷的导管轴(在图1中为“被着色的CV导管轴”)
采用Loctite将被涂敷的导管轴粘到Nitinol导线上,从而防止被涂敷的导管轴在测试期间滑动,该导管轴距离Nitinol导线的一端(距离载荷单元)200mm。这确保了当被涂敷的导管轴***测试装置中时,其刚好位于曲率之前(见图1)。被涂敷的导管轴被置于Milli-Q水中30秒,从而确保亲水性涂层彻底润湿。在样品润湿30秒期间,Congo红指示剂部分溶于水中。将Nitinol导线和被粘住的经涂敷导管轴在导管入口部分***直且被预润湿的Pro-Flo引导导管中。将Pro-Flo引导导管和被***的经涂敷导管轴置于聚合物支撑模具中,该模具中,特定180°的曲率为40mm,然后将额外的Milli-Q水小心冲入Pro-Flo引导导管中,从而确保内部空间弯曲润湿。
将聚合物模具和含有被***经涂敷导管轴的Pro-Flo引导导管置于Zwick拉伸测试仪上并通过夹具附接到载荷单元,该载荷单元被放置在模具顶部上方350mm处。现在导管轴的末端刚好处于Pro-Flo引导导管将要进入弯曲部之前的内部位置处,摩擦(和磨损)主要在此发生。
采用Zwick拉伸测试仪,将被涂敷的导管轴***100mm的长度,然后以200mm/min的速度拉出同样的长度。一个***和拉出被确定为1个循环。对每个样品进行该项测试,5个循环。
颗粒收集
在上述颗粒释放磨损测试后,将Pro-Flo引导导管的一侧从模具上取下,并放置在收集Pro-Flo引导导管中的Milli-Q水的瓶的上方。将含有10ml Milli-Q水的注射器连接到Pro-Flo引导导管的导管入口部分,冲洗Pro-Flo引导导管。取出Nitinol导线和被粘住的经涂敷导管轴,然后用10ml的Milli-Q水冲洗。用Milli-Q水冲洗Pro-Flo引导导管四次,每次10ml。对收集到的60ml Milli-Q水进行颗粒测试(参见以下),同时将Pro-Flo引导导管干燥,以进一步目测被有色颗粒的污染情况。未发现颗粒。
使用0.45-微米的Millipore过滤器(型号HAWP)过滤收集到的Milli-Q水溶液。采用该过滤器,还收集小于10微米的颗粒,然而根据USP28标准这种小颗粒不需计算在内。而且,如下所述图象分析能够清楚地分辩大于10微米和小于10微米的尺寸。Millipore玻璃Büchner漏斗***被用于该过程。
首先用纯水润湿过滤器,以确保过滤器不会被太过染红。不能抑制轻微粉红。采用白色和彩色平衡对这个背景色进行校正。这种校正不会影响最终结果。
成像
采用安装有CC-12 Soft成像***的LEICA MA FLIII记录显微图像。采用带有光导(固定到显微镜上)的LEICA CLS 150X以180°反向散射模式照射过滤器。上部开关被设定为数值4,下部开关被设定在位置6处。采用10×放大,变焦因子为5。用白纸自动设定白色平衡。捕捉每张照片的照明时间被设定为3.900ms。用总共9张照片对过滤器进行部分成像,每张代表2.71×2.12mm(等于5.7mm2)的面积。将由9块格子组成的一张纸放置在过滤器下方,从而能够记录每块的图像。过滤器的总面积为1020mm2。对于整个过滤器而言,校正因子为1020/(9x5.75)=20。
图像分析
图像分析包括如下步骤:
-扣除背景
-目标分析
-数据可视化
由于过滤器对Congo红染料的吸收可变而造成背景变化,因此必须进行背景校正。
打开Bersoft成像软件“Image Measurement Professional 4.02”中的图像,然后选取通过中心的像素切片(pixel slice),从而揭示背景弯曲(background curvature)。使用如果过程:大约沿着图像的中心选取垂直切片和水平切片。向Excel输出像素值,其中对两个切片进行拟合。
然后,在Mathematica Workbook中使用二次曲线以扣除背景(参见如下代码)。
为了背景扣除所用计算代码
fMain=Import[″D:\\image.jpg″];
fTotal=fMain;{n1,n2,n3}=Dimensions[fMain[[1,1]]];
nx=n1;ny=n2;
(*--Fit of Red background--*)
tabelRed=Table[fMain[[1,1,x,y,1]],{x,nx},{y,ny}];
(*---Generate table t.b.v.″Fit″.*)
tabelFit=Flatten[Table[{x,y,tabelRed[[x,y]]},{x,nx},{y,ny}],1];
(*---Fit,calculate parameters.*)
opl=Fit[tabelFit,{1,x,x^2,y,y^2},{x,y}];
r0=opl[[1]];{r1,r2,r3,r4}=Table[opl[[i,1]],{i,2,5}];
Print[″pLijst=″,{r0,r1,r2,r3,r4}];
tabelRed=.
tabelFit=.
fTotal[[1,1]]=Table[{Abs[(fMain[[1,1,i,j,3]]-(r0+r1*i+r2*i^2+r3*j+r4*j^2)-
10)*2-40],0,0},
{i,n1},{j,n2}];
Export[″D:\\BackgroundRSubtracted.jpg″,fTotal,″JPEG″];
fTotal=.
fMain=.
opl=.
所有RGB颜色组合成一个数值,并***RGB Red中。所得图片被保存为JPG文件。然后在Bersoft成像软件中打开图片,以检测所有RGBRed像素值大于24的对象。选择这样的水平,以使其刚好高于剩余的所有背景数值。
分析所有对象以后,数据输出到Excel中,其中进行可视化。将所有9张图片的结果放在一起,然后针对过滤器总表面的分数进行校正。
解释说明
分析过滤器上的颗粒。根据USP28忽略在所有方向上都小于10微米的颗粒。根据USP28标准记录在至少一个方向上大于10微米的颗粒。将颗粒表面积转化成颗粒体积,假定颗粒是刚性球体。应当考虑的是:导管具有2微米的涂层厚度。
标准:
颗粒>10微米(颗粒体积介于500μm3和8000μm3之间):每个释放测试(=每个过滤器)小于3000个。
颗粒>25微米(颗粒体积>8000μm3):每个释放测试(=每个过滤器)小于300个。
实施例1和对比例A和B的颗粒释放磨损测试结果
如上所述,对导管轴上的亲水性涂层1、A和B进行颗粒释放磨损测试。从这三个涂层上释放的颗粒表示在表4中。
表4:与USP标准相关的颗粒数
样品 | >10微米 | >25微米 | 通过与否 |
实施例1 | 80 | 0 | 是 |
对比例A | 820 | 40 | 有条件的 |
对比例B | 6340 | 1260 | 否 |
上表表明,采用本发明的涂层,颗粒释放明显减少。
Claims (15)
2.如权利要求1所述的涂料配制品,其中,所述Norrish I型光引发剂选自由苯偶姻衍生物、羟甲基苯偶姻和4-苯甲酰基-1,3-二氧杂戊环衍生物、苄基缩酮、α,α-二烷氧基苯乙酮、α-羟基苯烷基酮、α-氨基苯烷基酮、酰基氧化膦、二酰基氧化膦、酰基硫化膦和卤代苯乙酮衍生物组成的组。
3.如权利要求1或权利要求2所述的涂料配制品,其中,所述Norrish II型光引发剂选自由芳族酮,诸如二苯甲酮、呫吨酮、二苯甲酮的衍生物(例如氯二苯甲酮)、二苯甲酮和二苯甲酮衍生物的共混物(例如Photocure 81,4-甲基-二苯甲酮与二苯甲酮的50/50共混物)、米蚩酮、乙基米蚩酮、噻吨酮和其它呫吨酮衍生物如Quantacure ITX(异丙基噻吨酮)、苯偶酰、蒽醌(例如2-乙基蒽醌)、香豆素或者这些光引发剂的化学衍生物或组合组成的组。
4.如权利要求1-3中任意一项所述的涂料配制品,其中,所述式(1)的多官能可聚合化合物具有500g/mol或更高的数均分子量(Mn)并且/或者具有2000g/mol或更低的数均分子量(Mn)。
5.如权利要求1-4中任意一项所述的涂料配制品,其中,G包含至少一个杂原子。
6.如权利要求1-5中任意一项所述的涂料配制品,其中,G是亲水性多官能化合物的残基,优选选自由聚醚、聚酯、聚氨酯、聚环氧乙烷、聚酰胺、聚(甲基)丙烯酰胺、聚(甲基)丙烯酸、聚噁唑烷酮、聚乙烯醇、聚乙烯亚胺、多肽或多糖诸如纤维素和淀粉或上述任意组合,更优选含有至少一个聚乙二醇或聚丙二醇嵌段的聚合物。
7.如权利要求1-6中任意一项所述的涂料配制品,其中,R1=H,R2=H,或者R1为CH3,R2=H。
8.如权利要求1-7中任意一项所述的涂料配制品,进一步包含非离子亲水性聚合物,所述非离子亲水性聚合物选自由如下组成的组:聚(内酰胺)例如聚乙烯基吡咯烷酮(PVP),聚氨酯,丙烯酸和甲基丙烯酸的均聚物和共聚物,聚乙烯醇,聚乙烯基醚,马来酸酐基共聚物,聚酯,乙烯基胺,聚乙烯亚胺,聚环氧乙烷,聚(羧酸),聚酰胺,聚酸酐,聚磷嗪、纤维素类例如甲基纤维素、羧甲基纤维素、羟甲基纤维素和羟丙基纤维素,肝磷脂,右旋糖苷,多肽例如胶原质、纤维蛋白和弹性蛋白,多糖例如壳聚糖、透明质酸、海藻酸、明胶和壳多糖,聚酯例如聚丙交酯、聚乙交酯和聚己内酯,多肽例如胶原质、白蛋白、寡肽、多肽、短链肽、蛋白质和寡聚核苷。
9.如权利要求1-8中任意一项所述的涂料配制品,进一步包含亲水性聚合物和/或聚电解质,其中,所述亲水性聚合物和聚电解质(如果存在)与所述多官能可聚合物化合物的重量比介于50∶50和95∶5之间。
10.一种亲水性涂层,所述亲水性涂层可通过将权利要求1-9中任意一项所述的亲水性涂料配制品固化得到。
11.一种润滑涂层,所述润滑涂层可通过将润湿液体施加到权利要求10所述亲水性涂层上得到。
12.一种润滑涂层,所述润滑涂层的耐磨性根据颗粒释放磨损测试进行测试时相当于小于3000个、优选小于2000个、更优选小于1000个,具体小于500个大于10μm的颗粒。
13.一种制品,所述制品包含至少一层权利要求10-12中任意一项所述的亲水性涂层或润滑涂层。
14.如权利要求13所述的制品,其中,所述制品为医疗器械或构件,诸如导管、导线、支架、注射器、金属和塑料植入物、接触镜和医用管。
15.在基材上形成亲水性涂层的方法,所述方法包括:
将权利要求1-9中任意一项所述的亲水性涂料配制品涂敷到所述基材的至少一个表面上;
通过将所述配制品暴露于使引发剂活化的电磁辐射下,从而使所述涂料配制品固化。
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- 2009-03-12 MY MYPI2010003945A patent/MY160698A/en unknown
- 2009-03-12 US US12/920,399 patent/US20110059874A1/en not_active Abandoned
- 2009-03-12 JP JP2010550200A patent/JP5521237B2/ja active Active
- 2009-03-12 BR BRPI0909064A patent/BRPI0909064A2/pt not_active IP Right Cessation
- 2009-03-12 MX MX2010009982A patent/MX2010009982A/es unknown
- 2009-03-12 ES ES09718754.6T patent/ES2608823T3/es active Active
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Also Published As
Publication number | Publication date |
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CN101970583B (zh) | 2012-11-28 |
JP2011513566A (ja) | 2011-04-28 |
JP5521237B2 (ja) | 2014-06-11 |
MY160698A (en) | 2017-03-15 |
ES2608823T3 (es) | 2017-04-17 |
US20150352259A1 (en) | 2015-12-10 |
BRPI0909064A2 (pt) | 2019-02-26 |
WO2009112548A1 (en) | 2009-09-17 |
US20110059874A1 (en) | 2011-03-10 |
DK2252661T3 (en) | 2017-01-16 |
MX2010009982A (es) | 2010-09-30 |
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