CN103849002B - 表面改性弹性体 - Google Patents
表面改性弹性体 Download PDFInfo
- Publication number
- CN103849002B CN103849002B CN201310459308.8A CN201310459308A CN103849002B CN 103849002 B CN103849002 B CN 103849002B CN 201310459308 A CN201310459308 A CN 201310459308A CN 103849002 B CN103849002 B CN 103849002B
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- China
- Prior art keywords
- polymerization
- low
- modified
- absorption material
- protein absorption
- Prior art date
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Abstract
本发明提供一种无需使用价格昂贵的具有自润滑性的树脂、可赋予优越的滑动性、对反复滑动的耐久性、蛋白质的防止吸附性和防止凝集性等性能且通过能维持密封性的硫化橡胶或热塑性弹性体的表面改性方法得到的注射器用垫圈等表面改性弹性体。本发明涉及具有至少一部分通过表面改性方法进行改性的表面的注射器用垫圈等表面改性弹性体,所述表面改性方法包括工序1和工序2,其中,工序1在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点,工序2以所述聚合引发点为起点,使分子内具有C‑N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链。
Description
技术领域
本发明涉及通过规定的表面改性方法得到的注射器用垫圈、轮胎、导管、低蛋白质吸附性材料等表面改性弹性体。
背景技术
边维持密封状态边滑动的部分,例如,注射器的柱塞一体化的柱塞和进行注射筒密封的垫圈中,虽然采用了重视密封性的橡胶等弹性体,但在滑动性上还存在若干问题(参照专利文献1)。为此,在滑动面上涂布硅酮油等滑动性改良剂,但有人指出硅酮油可能会促进最近上市的生物制剂中的蛋白质吸附·凝集。另一方面,由于没有涂布滑动性改良剂的垫圈滑动性差,因此,投药时会产生柱塞不能平滑按下而脉动、注入量变得不准确、给患者带来痛苦等问题。
如此,为了满足密封性和滑动性的相反要求,提出了覆盖具有自润滑性的PTFE膜的技术(参照专利文献2),但由于一般价格昂贵,加工制品的制造成本上升,限定了其应用范围。另外,覆盖了PTFE膜的制品在用于需要反复滑动等、耐久性的用途时,也担心其可靠性。更进一步说,由于PTFE对放射线耐受性弱,存在不能通过射线进行灭菌的问题。
另外,还需要考虑要求在水存在下的滑动性的其他用途中的应用。即还可以期待如下效果,通过降低载药注射器的注射筒内表面和用于送水的管或管的内表面的流动阻力、增大或者显著降低与水的接触角,从而无损失地进行送水。另外,插入血管·尿道中的导管,为了不损伤血管和尿道、不给人带来疼痛,需要有高的滑动性。更进一步说,通过降低轮胎花纹沟表面的流动阻力、增大或者显著降低与水的接触角,使得在湿路面和雪路面上的水和雪的排除变良好,作为结果,提高其湿路打滑性、抓地性,改善安全性。也可期待通过减少轮胎的侧壁面和建筑物墙壁的滑动阻力、增加与水的接触角,使垃圾和粉尘变得难以附着。
再者,还可以期待如下有益效果。通过隔膜泵、隔膜阀等隔膜运送水或者水溶液等时,其压损变小。通过提高滑雪橇和滑雪板的滑行面的滑动性,使滑行变得容易。通过提高交通标志和招牌的滑动性,使雪变得容易滑落,容易看见标志。通过降低船外周面的滑动阻力、增大与水的接触角,减少水的阻力的同时,外周面也变得难以吸附蛋白质,其结果是,不易附着细菌。通过改良泳装的线表面的滑动性,从而减少水的阻力。
现有技术文献
专利文献
专利文献1:日本专利特开2004-298220号公报
专利文献2:日本专利特开2010—142573号公报
发明内容
发明要解决的问题
本发明的目的在于解决上述问题,提供一种无需使用价格昂贵的具有自润滑性的树脂、可赋予优越的滑动性、对反复滑动的耐久性、蛋白质的防止吸附性和防止凝集性等性能且通过能维持密封性的硫化橡胶或热塑性弹性体的表面改性方法得到的注射器用垫圈、轮胎、导管和低蛋白质吸附性材料等表面改性弹性体。
解决问题的手段
本发明涉及具有至少一部分通过表面改性方法进行改性的表面的注射器用垫圈;所述表面改性方法包括工序1和工序2;
所述工序1,在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点;
所述工序2,以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链。
本发明涉及具有至少一部分通过表面改性方法进行改性的轮胎花纹沟表面的轮胎;所述表面改性方法包括工序1和工序2;
所述工序1,在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点;
所述工序2,以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链。
本发明涉及具有至少一部分通过表面改性方法进行改性的表面的导管;所述表面改性方法包括工序1和工序2;
所述工序1,在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点;
所述工序2,以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链。
本发明涉及具有至少一部分通过表面改性方法进行改性的表面的低蛋白质吸附性材料;所述表面改性方法包括工序1和工序2;
所述工序1,在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点;
所述工序2,以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链。
所述硫化橡胶或热塑性弹性体,优选具有与双键相邻的碳原子,即烯丙位的碳原子。
所述聚合引发点,优选使所述改性对象表面吸附聚合引发剂而形成。在这里,所述聚合引发剂,优选为二苯甲酮系化合物和/或噻吨酮系化合物。
更进一步说,优选对吸附的所述聚合引发剂进行光照射,使其化学键合于所述改性对象表面。
所述自由基聚合,优选为光自由基聚合。在这里,所述光自由基聚合,优选为照射波长300~450nm光的自由基聚合。另外,所述自由基聚合,优选在所述光照射时或光照射前,向反应容器和反应液中导入不活泼气体,置换为不活泼气体气氛,进行聚合。
所述分子内具有C-N键的单体,优选选自由(甲基)丙烯酰胺、二甲基(甲基)丙烯酰胺、二乙基(甲基)丙烯酰胺、异丙基(甲基)丙烯酰胺、羟基(甲基)丙烯酰胺和(甲基)丙烯酰吗啉构成的群中的至少一种。
所述光自由基聚合,优选使所述分子内具有C-N键的单体或其溶液接触于所述改性对象表面或者吸附或共价键合了所述聚合引发剂的改性对象表面,再照射光,使聚合进行。在这里,所述分子内具有C-N键的单体或其溶液含有阻聚剂,优选在该阻聚剂的存在下,使其聚合。所述阻聚剂,优选为4-甲基苯酚。所述聚合物链的长度,优选为10~50000nm。
发明效果
本发明是具有至少一部分通过表面改性方法进行改性的表面的注射器用垫圈、轮胎、导管和低蛋白质吸附性材料等表面改性弹性体,所述表面改性方法包括工序1和工序2,其中,工序1是在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点,工序2以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链,因而能够在改性对象表面赋予优良的滑动性和对于反复滑动的耐久性的同时,也能得到良好的密封性。另外,经改性的表面改性弹性体,由于不具有PTFE的聚合物骨架,使通过γ射线等放射线进行灭菌成为可能。更进一步说,由于使用分子内具有C-N键的单体,使抑制蛋白质吸附、防止生物制药中的蛋白质吸附或凝集成为可能。
附图说明
图1是一例注射器用垫圈的实施方式的侧面图;
图2是一例充气轮胎(整体未图示)的胎面部的展开图;
图3是一例图2的A1-A1截面图。
图中附图标记说明如下:
1为垫圈,11a、11b、11c为环状突起部,13为底面部表面,2为胎面部,3a为中央纵沟,3b为胎肩纵沟,5为细沟,6为中间倾斜沟,7为连接沟,8、8a、8b为胎肩横沟。
具体实施方式
本发明是一种表面改性方法和通过该表面改性方法得到的具有至少一部分改性表面的注射器用垫圈、轮胎、导管和低蛋白质吸附性材料等表面改性弹性体;所述表面改性方法包括工序1和工序2,其中,工序1是在由硫化橡胶或热塑性弹性体构成的改性对象表面形成聚合引发点,工序2以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链。
工序1中,在硫化成形后的橡胶或成形后的热塑性弹性体(改性对象)表面形成聚合引发点。作为所述硫化橡胶、所述热塑性弹性体,适宜采用具有与双键相邻的碳原子(烯丙位的碳原子)的物质。
作为改性对象的橡胶,可列举出苯乙烯丁二烯橡胶、丁二烯橡胶、异戊二烯橡胶、天然橡胶、脱蛋白质天然橡胶等二烯系橡胶,以及含有几个百分点的异戊二烯单元作为不饱和度的丁基橡胶、卤代丁基橡胶等。当采用丁基橡胶、卤代丁基橡胶时,从硫化橡胶的提取物变少的观点来看,优选通过三嗪交联的橡胶。在这种情况下,也可含有吸酸剂,作为适合的吸酸剂,可举出例如水滑石、碳酸镁等。
采用其他橡胶时,优选硫磺硫化。在这种情况下,可以添加硫磺硫化中一般采用的硫化促进剂、氧化锌、填充剂、硅烷偶联剂等配料。作为填充剂,适宜采用碳黑、二氧化硅、粘土、滑石粉、碳酸钙等。
另外,橡胶的硫化条件可进行适当地设定,橡胶的硫化温度优选为150℃以上,更优选为170℃以上,进一步优选为175℃以上。
作为热塑性弹性体,例如,可举出通过使可塑性成分(硬链段)的聚集体担任交联点的作用,从而在常温下具有橡胶弹性的高分子化合物(苯乙烯-丁二烯苯乙烯共聚物等热塑性弹性体(TPE)等);通过热塑性成分和橡胶成分混合、通过交联剂进行动态交联而具有橡胶弹性的高分子化合物(含有苯乙烯系嵌段共聚物或烯烃系树脂和交联的橡胶成分的聚合物合金等热塑性弹性体(TPV)等)。
另外,作为其他的适合的热塑性弹性体,可举出尼龙、聚酯、聚氨酯、聚丙烯以及它们的动态交联热塑性弹性体。当采用动态交联热塑性弹性体时,优选以卤代丁基橡胶在热塑性弹性体中进行动态交联。在这种情况下的热塑性弹性体优选尼龙、聚氨酯、聚丙烯、SIBS(苯乙烯-异丁烯-苯乙烯嵌段共聚物)等。
聚合引发点通过例如,使聚合引发剂吸附于改性对象表面,从而形成。作为聚合引发剂,例如,可举出羰基化合物、四乙基秋兰姆二硫化物等有机硫化合物、过硫化物、氧化还原系化合物、偶氮化合物、重氮化合物、卤素化合物、光还原性色素等,其中,优选羰基化合物。
作为聚合引发剂的羰基化合物,优选二苯甲酮及其衍生物,例如,适宜采用下式所示的二苯甲酮系化合物。
【化1】
(式中,R1~R5及R1′~R5′相同或不相同,表示氢原子、烷基、卤素(氟、氯、溴、碘)、羟基、伯~叔氨基、巯基或可以含有氧原子、氮原子、硫原子的烃基,还可以相邻的任意两个相互连接,与它们所键合的碳原子一起形成环结构)。
作为二苯甲酮系化合物的具体例子,可举出二苯甲酮、呫吨酮、9-芴酮、2,4-二氯二苯甲酮、邻苯甲酰苯甲酸甲酯、4,4′-双(二甲氨基)二苯甲酮,4,4′-双(二乙氨基)二苯甲酮等。其中,从获得良好的聚合物刷这一观点来看,特别优选为二苯甲酮、呫吨酮、9-芴酮。作为二苯甲酮系化合物,氟二苯甲酮系化合物也适合使用,例如,可举出2,3,4,5,6-五氟二苯甲酮、十氟二苯甲酮等。
作为聚合引发剂,从聚合速度快和易于吸附于橡胶等和/或容易与橡胶等反应的观点来看,噻吨酮系化合物也能适合使用。例如,适宜采用下式所示的化合物。
【化2】
(式中,R11~R14及R11′~R14相同或不相同,表示氢原子、卤素原子、烷基、环状烷基、芳基、烯基、烷氧基或芳氧基。)
作为上式所示的噻吨酮系化合物,可举出噻吨酮、2-异丙基噻吨酮、4-异丙基噻吨酮、2,3-二甲基噻吨酮、2,4-二甲基噻吨酮、2,3-二乙基噻吨酮、2,4-二乙基噻吨酮、2,4-二氯噻吨酮、2-甲氧基噻吨酮、1-氯-4-丙氧基噻吨酮、2-环己基噻吨酮、4-环己基噻吨酮、2-乙烯基噻吨酮、2,4-二乙烯基噻吨酮、2,4-二苯基噻吨酮、2-丁烯基-4-苯基噻吨酮、2-甲氧基噻吨酮、2-对-辛氧基苯基-4-乙基噻吨酮等。其中,优选为R11~R14及R11′~R14′中的1~2个、特别是2个被烷基所取代的物质,更优选为2,4-Diethylthioxanthone(2,4-二乙基噻吨酮)。
作为二苯甲酮系化合物、噻吨酮系化合物等聚合引发剂向改性对象表面进行吸附的方法,可采用公知的方法。例如,对于二苯甲酮系化合物、噻吨酮系化合物,用有机溶剂使其溶解,用得到的溶液处理对象的改性表面部位,由此使二苯甲酮系化合物、噻吨酮系化合物吸附在表面,并根据需要通过干燥使有机溶剂蒸发,由此形成聚合引发点。作为表面处理方法,只要使该二苯甲酮系化合物、该噻吨酮系化合物溶液能接触改性对象表面,就没有特别限制,例如,适合采用该二苯甲酮系化合物、该噻吨酮系化合物溶液的涂布、喷涂、在该溶液中浸渍等。更进一步说,仅一部分表面需要进行表面改性时,只要使聚合引发剂仅吸附于所需的一部分表面,在这种情况下,例如,适合采用该溶液的涂布、该溶液的喷涂等。作为所述溶剂,可使用甲醇、乙醇、丙酮、苯、甲苯、甲基乙基酮、乙酸乙酯、THF等,但在不使改性对象溶胀方面、干燥蒸发快速方面,优选为丙酮。
另外,优选通过二苯甲酮系化合物溶液、噻吨酮系化合物溶液对改性对象部位进行表面处理,使其吸附聚合引发剂后,再经光照射,使化学键合于改性对象表面。例如,通过照射波长300~450nm(优选为300~400nm,更优选为350~400nm)的紫外线,能使二苯甲酮系化合物、噻吨酮系化合物溶液在表面上进行固定化。所述工序1和该固定化中,去除橡胶表面的氢原子、二苯甲酮的C=O中的碳原子和橡胶表面的碳原子以共价键形成的同时,去除的氢原子结合到C=O中的氧原子上,形成C-O-H。另外,由于该脱氢反应是通过改性对象的烯丙位的氢原子选择性地进行,因此,优选为含有带烯丙氢的丁二烯、异戊二烯单元的橡胶。
【化3】
R:氢或碳原子数为1~4的烷基
其中,优选通过聚合引发剂对改性对象表面进行处理,使聚合引发剂吸附于表面,接着,通过对处理后的表面进行300~400nm的LED光照射,形成聚合引发剂,特别优选通过二苯甲酮系化合物溶液、噻吨酮系化合物溶液等对改性对象表面进行表面处理,使聚合引发剂吸附后,再通过对处理后的表面进行300~400nm的LED光照射,由此使吸附的聚合引发剂化学键合于表面。在这里,LED光的波长,适宜采用355~380nm。
工序2中,以工序1中形成的聚合引发点为起点,使分子(1分子)内具有C-N键的单体进行自由基聚合,在改性对象表面上生长聚合物链。如此,制造在改性对象表面上形成了分子内具有C-N键的单体自由基聚合而得到的聚合物链的注射器用垫圈等表面改性弹性体。
作为分子内具有C-N键的单体,例如,适宜采用(甲基)丙烯酰胺;N-烷基取代的(甲基)丙烯酰胺衍生物【N-乙基(甲基)丙烯酰胺、N-正丙基(甲基)丙烯酰胺、N-异丙基(甲基)丙烯酰胺、N-环丙基(甲基)丙烯酰胺、N-乙氧基乙基(甲基)丙烯酰胺等】;N,N-二烷基取代的(甲基)丙烯酰胺衍生物【N,N-二甲基(甲基)丙烯酰胺、N,N-乙基甲基(甲基)丙烯酰胺、N,N-二乙基(甲基)丙烯酰胺等】;羟基(甲基)丙烯酰胺;羟基(甲基)丙烯酰胺衍生物【N-羟基乙基(甲基)丙烯酰胺等】;具有环状基团的(甲基)丙烯酰胺衍生物【(甲基)丙烯酰吗啉等】等。其中,优选为(甲基)丙烯酰胺、二甲基(甲基)丙烯酰胺、二乙基(甲基)丙烯酰胺、异丙基(甲基)丙烯酰胺、羟基(甲基)丙烯酰胺和(甲基)丙烯酰吗啉;在低蛋白质吸附性方面,优选为(甲基)丙烯酰胺,特别是丙烯酰胺。
作为工序2的分子内具有C-N键的单体的自由基聚合方法,在吸附或共价键合了二苯甲酮系化合物、噻吨酮系化合物等的改性对象表面上,涂布(喷雾)具有C-N键的单体(液体)或其溶液,或者将改性对象浸渍在具有C-N键的单体(液体)或其溶液中,通过紫外线等光照射,分别进行自由基聚合(光自由基聚合),在该改性对象表面上生长聚合物链。更进一步说,经上述涂布后,在表面覆盖上透明的玻璃·PET·聚碳酸酯等,通过从其上方进行紫外线等光照射,分别进行自由基聚合(光自由基聚合),能使聚合物链生长于改性对象表面上。
涂布(喷雾)溶剂、涂布(喷雾)的方法、浸渍方法、照射条件等,适宜采用现有公知的材料和方法。另外,作为具有C-N键的单体(自由基聚合性单体)的溶液,采用水溶液或使自由基聚合性单体溶解于有机溶剂而形成的溶液,其中,该有机溶剂不能溶解所使用的聚合引发剂(二苯甲酮系化合物等)。另外,作为具有C-N键的单体(液体)及其溶液,也可采用含有4-甲基苯酚等公知的阻聚剂的单体及其溶液。
本发明中,单体(液体)或其溶液涂布后或浸渍于单体或其溶液后,通过光照射进行具有C-N键的单体的自由基聚合,但适宜采用具有以紫外光作为主要发光波长的高压汞灯、金属卤化物灯、LED灯等UV照射光源。照射量根据聚合时间和反应进行的均匀性考虑,进行适当设定。另外,为了防止由于反应器内的氧等活性气体的聚合阻碍,在光照射时或者光照射前,优选去除反应器内和反应液中的氧。因此,适宜采用在反应器内和反应液内,导入氮气或氩气等不活泼气体,将氧等活性氧气体排出反应体系外,进行反应体系内的不活泼气体气氛置换等。更进一步说,为了防止氧等的反应阻碍,也适宜采用将UV照射光源设置在玻璃和塑料等的反应器与反应液和改性对象之间、空气层(氧含量15%以上)不能进入的位置等办法。
紫外线照射时,其波长优选为300~450nm,更优选为300~400nm。由此,在改性对象表面能形成良好的聚合物链。300nm以下的紫外线,存在使单体并非由表面单独地进行聚合而生长聚合物的弊端。作为光源,可采用高压汞灯、具有365nm中心波长的LED、具有375nm中心波长的LED等。其中,优选300~400nm的LED光照射,更优选355~380nm的LED光照射。特别是,具有接近于二苯甲酮激发波长366nm的365nm中心波长的LED等,在效率方面是优选的。
另外,工序2中,通过形成聚合物链,得到优良的滑动性、耐久性、蛋白质的防止吸附性和防止凝集性且又能维持良好的密封性。形成的聚合物链的聚合度,优选为20~200000,更优选为350~50000。小于20时,聚合物链过短,埋没于改性对象表面的凹凸中,具有不能发挥滑动性的趋势。超过200000时,使用的单体量变多,具有在经济上变不利的趋势。
工序2形成的聚合物链的长度优选为10~50000nm,更优选为100~50000nm。小于10nm时,具有不能得到良好的滑动性的趋势。超过50000nm时,滑动性的进一步提高已不能期待,由于使用高价的单体,原料成本具有上升的趋势,另外,通过表面处理的表面花纹变得肉眼可见,具有损害美观、密封性降低的趋势。
所述工序2中,以聚合引发点为起点,也可使两种以上的分子内具有C-N健的单体同时进行自由基聚合,另外,改性对象表面上也可生长多种聚合物链。所述表面改性方法,也可进行聚合物链间交联。在这种情况下,聚合物链之间可以形成有离子交联、基于具有氧原子的亲水基的交联。更进一步说,也可通过少量添加一分子内具有2个以上乙烯基的化合物进行聚合,在聚合中的聚合物链之间导入交联结构。作为一分子内具有2个以上乙烯基的化合物,优选为N,N′-亚甲基双丙烯酰胺等。
通过对硫化橡胶或热塑性弹性体采用上述表面改性方法,得到表面改性弹性体。例如,得到在水存在下或干燥状态下滑动性优良的表面改性弹性体,由于摩擦力低,在水阻力小方面也优良。另外,通过对三维形状的固体(弹性体等)的至少一部分适用于上述方法,可得到改性的表面改性弹性体。更进一步说,作为该表面改性弹性体的优选例,可举出聚合物刷(高分子刷)。在这里,聚合物刷是指,通过表面引发活性自由基聚合得到的graftingfrom的接枝聚合物。另外,接枝链从改性对象的表面取向为大致垂直的方向的,其熵变小,接枝链分子运动变低,从而得到滑动性,是优选的。更进一步说,作为刷密度,0.01链/nm2以上的准浓度及浓度刷是优选的。
另外,通过对硫化橡胶或热塑性弹性体采用上述表面改性方法,可制造至少一部分具有改性的表面的注射用垫圈。优选至少在垫圈表面的滑动部进行改性,也可在整个表面进行改性。
图1是一例注射用垫圈的实施方式的侧面图。如图1所示的垫圈1的与注射器的注射筒内周面接触的外周面上,在圆周方向具有连续突出的3个环状突起部11a、11b、11c。垫圈1中,作为适用所述表面改性的部位,可举出(1)环状突起部11a、11b、11c等与注射器接触的突起部表面,(2)包括环状突起部11a、11b、11c的侧面的整个表面,(3)该侧面的整个表面和底部表面13等。
更进一步说,轿车等车辆所使用的轮胎胎面形成的花纹沟通过采用所述表面改性方法,使花纹沟中生成聚合物刷,从而可以降低湿路面和雪路面的花纹沟表面的流体阻力,增大与水的接触角,因此可以提高水和雪的排除及流泄,能改善抓地性。
图2是一例充气轮胎(整体未图示)胎面部2的展开图,图3显示图2的A1-A1截面图。图2~3中,中央纵沟3a(沟深度D1)、胎肩纵沟3b(沟深度D2)是由在轮胎周方向以直线状延伸的直沟所构成。这样的直沟排水阻力变小,直线前行时能发挥高的排水性能。
另外,充气轮胎中,胎肩纵沟3b侧设置了在轮胎周方向上延伸的细沟5(沟深度D3)、从该细沟5面向中央纵沟3a倾斜延伸的中间倾斜沟6(沟深度D4)、相对于细沟5位于轮胎轴方向内侧且在轮胎周方向上相邻的中间倾斜沟6、连接6之间的连接沟7(沟深度D5)、从胎肩纵沟3b到面向轮胎外侧的胎肩横沟8、8a、8b(沟深度D6)等,这样的沟能发挥排水性能。此外,通过对这些沟使用上述方法,能发挥上述效果。
实施例
以下根据实施例对本发明进行具体的说明,但本发明并不局限于这些实施例。
(实施例1)
将含有异戊二烯单元的氯化丁基橡胶(不饱和度:1~2%)通过三嗪进行交联而得到的硫化橡胶垫圈(180。℃10分钟硫化)浸渍于二苯甲酮的1wt%丙酮溶液,使硫化橡胶表面吸附二苯甲酮。随后,取出硫化橡胶,干燥。将干燥的硫化橡胶浸渍于放入了丙烯酰胺水溶液(2.5M)的玻璃反应器内,以具有365nm波长的LED UV灯(2mW/cm2)照射60小时紫外线,进行自由基聚合,使橡胶表面生长聚合物链,得到表面改性弹性体垫圈(聚合物刷)。
(实施例2)
除将丙烯酰胺水溶液(2.5M)变更为1.25M丙烯酰胺水溶液、紫外线的照射时间变更为120小时以外,其他与实施例1相同,制作表面改性弹性体垫圈。
(实施例3)
除将二苯甲酮的1wt%丙酮溶液变更为2,4-二甲基噻吨酮化合物的1%丙酮溶液、紫外线的照射时间变更为30分钟以外,其他与实施例1相同,制作表面改性弹性体垫圈。
比较例1
采用氯化丁基橡胶通过三嗪交联的硫化橡胶垫圈(180℃10分钟硫化)。
(实施例4)
将含有异戊二烯单元的氯化丁基橡胶(不饱和度:1~2%)通过三嗪进行交联而得到的硫化橡胶垫圈(厚度2mm:180。℃10分钟硫化)浸渍于二苯甲酮的1wt%丙酮溶液,使硫化橡胶表面吸附二苯甲酮。随后,取出硫化橡胶,干燥。将干燥的硫化橡胶浸渍于放入了丙烯酰胺水溶液(2.5M)的玻璃反应器内,以具有365nm波长的LED UV灯(2mW/cm2)照射60小时紫外线,进行自由基聚合,使橡胶表面生长聚合物链,得到表面改性弹性体垫圈(聚合物刷)。
实施例、比较例中制作的表面改性弹性体通过以下的方法进行评价。
(聚合物链的长度)
硫化橡胶表面形成的聚合物链长度通过使用SEM以加速电压15kV、1000倍对形成有聚合物链的改性橡胶截面进行测量。所拍摄的聚合物层的厚度作为聚合物链的长度。
(摩擦阻力)
为了测量表面改质弹性体的表面摩擦阻力,将实施例和比较例中制作的硫化橡胶垫圈设置于注射器的COP树脂注射筒上,采用拉伸试验机进行推入,测量那时的摩擦阻力(推入速度:100mm/min)。将比较例1的摩擦阻力作为100,采用下式,以摩擦阻力指数表示各实施例、比较例。指数小的,表示摩擦阻力小。
(摩擦阻力指数)=各实施例的摩擦阻力/比较例1的摩擦阻力×100
(蛋白质吸附试验)
使表面改性弹性体在37℃接触1mg/mL牛血清白蛋白溶液3小时。这时,按照JIST9010,提取所吸附的牛血清白蛋白·蛋白质质量,通过Lowry法对提取液中的蛋白质量进行定量。将其值换算成表面改性弹性体片的单位面积的值。
【表1】
【表2】
从表1来看,明显显示了实施例的表面改性弹性体表面的摩擦阻力大幅度下降,得到了良好的滑动性。另外,由于只有表面进行了改性,因此,密封性与比较例1相同。
蛋白质吸附量超过0.4μg/cm2时,具有蛋白质变性层积、坚固吸附的趋势,但实施例4的蛋白质吸附量为0.3μg/cm2,该吸附量非常少,明确说明没有问题(表2)。
因此,用于注射器的柱塞垫圈时,拥有充分的密封性的同时,柱塞对于注射筒的摩擦力降低,注射器的操作可以容易且准确地进行。另外,注射器的注射筒以热塑性弹性体进行制作,在其内表面生成聚合物链时,也能与上述同样地容易地进行注射器操作。更进一步说,由于对表面的蛋白质吸附量少,能防止生物制剂中的蛋白质吸附·凝集。
另外,通过在轿车等所使用的轮胎胎面形成的花纹沟、侧壁、隔膜、滑雪橇或滑雪板的滑行面、游泳泳衣、道路标志、招牌等表面形成聚合物链,也能期待上述的效果。
Claims (13)
1.一种低蛋白质吸附性材料,其具有至少一部分通过表面改性方法进行改性的表面,所述表面改性方法包括工序1和工序2;
工序1:在作为改性对象的含有异戊二烯单元的丁基橡胶或卤代丁基橡胶表面形成聚合引发点;
工序2:以所述聚合引发点为起点,使分子内具有C-N键的单体进行自由基聚合,在所述改性对象表面上生长聚合物链,
所述分子内具有C-N键的单体为选自由(甲基)丙烯酰胺、二甲基(甲基)丙烯酰胺、二乙基(甲基)丙烯酰胺、异丙基(甲基)丙烯酰胺、羟基(甲基)丙烯酰胺构成的群中的至少一种。
2.如权利要求1记载的低蛋白质吸附性材料,其中,所述含有异戊二烯单元的丁基橡胶或卤代丁基橡胶具有与双键相邻的碳原子,即烯丙位的碳原子。
3.如权利要求1或2记载的低蛋白质吸附性材料,其中,所述聚合引发点,是使所述改性对象表面吸附聚合引发剂而形成的。
4.如权利要求1或2记载的低蛋白质吸附性材料,其中,所述聚合引发剂为二苯甲酮系化合物和/或噻吨酮系化合物。
5.如权利要求3记载的低蛋白质吸附性材料,其中,还对吸附的所述聚合引发剂进行光照射,使其化学键合于所述改性对象表面。
6.如权利要求1记载的低蛋白质吸附性材料,其中,所述自由基聚合为光自由基聚合。
7.如权利要求6记载的低蛋白质吸附性材料,其中,所述光自由基聚合为照射波长300~450nm光的自由基聚合。
8.如权利要求1记载的低蛋白质吸附性材料,其中,所述自由基聚合,是在光照射时或光照射前,向反应容器和反应液中导入不活泼气体,置换为不活泼气体气氛,进行聚合。
9.如权利要求6~8的任一项记载的低蛋白质吸附性材料,其中,所述光自由基聚合,是使所述分子内具有C-N键的单体或其溶液接触吸附或共价键合了所述聚合引发剂的改性对象表面,再照射光,使聚合进行。
10.如权利要求9记载的低蛋白质吸附性材料,其中,所述分子内具有C-N键的单体或其溶液含有阻聚剂,在该阻聚剂的存在下,使其聚合。
11.如权利要求10记载的低蛋白质吸附性材料,其中,所述阻聚剂为4-甲基苯酚。
12.如权利要求1记载的低蛋白质吸附性材料,其中,所述聚合物链的长度为10~50000nm。
13.如权利要求1记载的低蛋白质吸附性材料,其中,所述低蛋白质吸附性材料用于注射器用垫圈。
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EP2743294A1 (en) | 2014-06-18 |
US20140155510A1 (en) | 2014-06-05 |
US9752003B2 (en) | 2017-09-05 |
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JP2014108153A (ja) | 2014-06-12 |
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