CN103242487B - 表面改性方法及表面改性弹性体 - Google Patents
表面改性方法及表面改性弹性体 Download PDFInfo
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- CN103242487B CN103242487B CN201310013566.3A CN201310013566A CN103242487B CN 103242487 B CN103242487 B CN 103242487B CN 201310013566 A CN201310013566 A CN 201310013566A CN 103242487 B CN103242487 B CN 103242487B
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- Prior art keywords
- modifying method
- surface modifying
- polymer chain
- salt
- modified
- Prior art date
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Abstract
本发明提供可以根据用途赋予硫化橡胶或者热塑性弹性体滑动性、生物相容性等各种各样功能性的表面改性方法。本发明是以硫化橡胶或者热塑性弹性体为改性对象物的表面改性方法,包含上述改性对象物表面上形成聚合引发点的工序1,与以上述聚合引发点为起点使单体进行自由基聚合,使聚合物链在上述改性对象物表面生长的工序2,与功能化处理上述聚合物链的工序3。
Description
技术领域
本发明涉及表面改性方法以及具有至少一部分通过该表面改性方法得到的经改性的表面的注射器用密封垫片及引流管,具有至少一部分轮胎的槽表面的轮胎等的表面改性弹性体。
背景技术
维持密封状态且滑动部分如密封垫片,其与注射器的柱塞一体化,使柱塞与注射筒间密封,其重视密封性,使用橡胶等弹性体,但滑动性存在若干问题(参照专利文献1)。因此,在滑动面上涂敷聚硅氧烷油等滑动性改良剂,但最近指出聚硅氧烷油有可能给上市的生物制剂带来不良影响。另一方面,没有涂敷滑动性改良剂的密封垫片由于滑动性差,所以投药时不能平稳地压下柱塞而发生跳动,引发了注入量不正确,给患者带来痛苦等问题。
为了满足这样的密封性与滑动性相反的要求,有人提出包覆具有自我润滑性的PTFE膜的技术(参照专利文献2),但一般因为价格高,加工产品的制造成本上升,应用范围受到限制。此外,将包覆PTFE膜的产品用于反复进行滑动等要求耐久性的用途时,也担忧其可靠性。此外,PTFE不耐放射线,也存在不能采用照射线对其灭菌的问题。
此外,还考虑应用到其它用途,要求水存在条件下的滑动性,即,通过使充液注射筒的注射筒内表面或引流管等输送水用的管或者筒的内表面的流体阻力下降,或者使其与水的接触角增大或者明显下降,来无损耗地运送水。通过使轮胎的槽表面的流体阻力下降,或者使其与水的接触角增大或者明显下降,在湿地或冰雪路面上,排水或排雪变良好,结果提高了抓地性、抗水面打滑性,使得安全性改善。通过减少轮胎的胎侧面或建筑物的墙壁的滑动阻力,或者增大与水的接触角,也可以期待垃圾或粉尘不易附着。
进一步地还可以期待以下等有利效果,用隔膜泵、隔膜阀等隔膜输送水或水溶液等时,压力损失变小。通过提高双板滑雪板(ski)或单板滑雪板(snow board)的滑动面的滑动性,滑动变得容易。通过提高道路标识或看板的滑动性,使雪容易滑下,而变得容易看见标识。通过使船的外周面的滑动阻力下降,或者增大与水的接触角,而使水的阻力减小,同时外周面变得不易附着细菌。通过改良泳衣的纱线表面的滑动性,水的阻力降低。
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2010-142537号公报
发明内容
发明要解决的课题
本发明为解决所述课题,目的在于提供一种根据用途能赋予滑动性、生物相容性等各种各样功能性的硫化橡胶或热塑性弹性体的表面改性方法。本发明的目的还在于提供一种具有至少一部分通过该表面改性方法得到的经改性的表面的注射器用密封垫片及引流管、具有至少一部分轮胎的槽表面的轮胎等表面改性弹性体。
解决课题的手段
本发明是以硫化橡胶或者热塑性弹性体为改性对象物的表面改性方法,包含在上述改性对象物表面上形成聚合引发点的工序1,与以上述聚合引发点为起点使单体进行自由基聚合,使聚合物链在上述改性对象物表面生长的工序2,与功能化处理上述聚合物链的工序3。
上述工序1,对改性对象物的表面照射300~400nm的LED光,由上述表面上的光敏剂形成聚合引发点,上述工序2,优选以上述聚合引发点为起点,对单体照射300~400nm的LED光使其进行自由基聚合,从而使聚合物链生长的工序。
上述硫化橡胶或者热塑性弹性体优选具有与双键邻接的碳原子即烯丙位的碳原子。
所述光敏剂优选使用下述式(1)表示的二苯甲酮系化合物。
【化1】
(式(1)中,R1~R5及R1′~R5′相同或不同,表示氢原子、烷基、卤素、羟基、伯~叔胺基、巯基或者可以含有氧原子、氮原子或硫原子的烃基,相邻的任意两个可以相互连结,同与它们键合的碳原子一起形成环结构。)
上述工序2中,优选在上述单体进行自由基聚合时添加还原剂或者抗氧化物质。
所述还原剂或者抗氧化物质优选使用由核黄素、抗坏血酸、α-生育酚、β-胡萝卜素及尿酸所成群中的至少1种。
所述表面改性方法优选进行所述光照射时或照射前,将非活性气体导入反应容器及反应液中,将其置换成非活性气体气氛,使之聚合。
所述工序3,优选所述聚合物链的侧链转换为盐。
例如,通过对所述聚合物链的侧链使用碱金属盐或者抗菌性金属盐等转换为盐,使所述聚合物链的侧链与氨水接触后转换为盐,对所述聚合物链的侧链使用碱性盐转换为盐,对所述聚合物链的侧链使用硝酸盐、碳酸盐或者卤化盐转换为盐,对所述聚合物链的侧链使用硝酸银、碳酸银或者氯化银转换为盐,来导入功能性基团,从而实施所述工序3。
同时,所述工序3,例如,通过使所述聚合物链的侧链中的羧酸基与胺化合物反应形成酰胺键,使所述聚合物链的侧链中的羧酸基与含有羟基的化合物反应形成酯键,来导入功能性基团,从而实施所述工序3。
在这里,所述功能性基团优选氟代烷基。同时所述胺化合物优选使用下述式表示的化合物。
CF3(CF2)n-(CX2)p-NH2-m((CF2)nCF3)m
(式中X表示氢或氟。n表示相同或者不同的1~10的整数。m表示0~2的整数p表示0~4的整数。)
优选所述自由基聚合性单体(液体)或者其溶液含有聚合抑制剂,在聚合抑制剂存在下聚合。在这里,所述聚合抑制剂优选使用4-甲基苯酚。
所述聚合物链的长度优选为10~50000nm。
本发明涉及由所述表面改性方法得到的表面改性弹性体。
本发明涉及一种由所述表面改性方法得到的表面改性弹性体,其要求具有在水存在下或干燥状态下的滑动性、低摩擦或低的水阻力。
本发明涉及由所述表面改性方法得到的表面改性弹性体,其要求具有抗菌性。
本发明涉及其三维形状的固体表面的至少一部分经所述表面改性方法改性的表面改性弹性体。
在此,所述表面改性弹性体优选为聚合物刷。
本发明进一步涉及具有至少一部分经所述表面改性方法改性的表面的注射器用密封垫片。
本发明进一步涉及具有至少一部分经所述表面改性方法改性的表面的注射器用引流管。
本发明进一步涉及具有至少一部分经所述表面改性方法改性的轮胎的槽表面的轮胎。
发明效果
根据本发明,可提供一种包含在硫化橡胶或者热塑性弹性体(改性对象物)的表面形成聚合引发点的工序1,与以上述聚合引发点为起点使单体进行自由基聚合,使聚合物链在上述改性对象物表面生长的工序2,与功能化处理上述聚合物链的工序3的表面改性方法,能够赋予聚合物链期望的功能,容易地提供具有滑动性、抗菌性等各种功能的表面改性弹性体。
附图说明
图1是一例注射器用密封垫片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的截面图A1-A1。
符号说明
1 密封垫片
11a、11b、11c 环状突起部
13 底面部的表面
2 胎面部
3a 中央纵槽
3b 胎肩纵槽
5 细槽
6 中间倾斜槽
7 连接槽
8、8a、8b 胎肩横槽
具体实施方式
本发明是以硫化橡胶或者热塑性弹性体为改性对象物的表面改性方法,包含在上述改性对象物表面上形成聚合引发点的工序1,与以上述聚合引发点为起点使单体进行自由基聚合,使聚合物链在上述改性对象物表面生长的工序2,与功能化处理上述聚合物链的工序3。
使丙烯酸等单体在改性对象物表面聚合形成聚合物链,通过此聚合物链可赋予滑动性等功能。另一方面,形成的聚丙烯酸的聚合物链,有其侧链的羧基使表面显示酸性的担忧,用于注射器的垫圈等时,对于药液,用于引流管时,对于蛋白质等体内环境恐怕会有影响。因此,优选表面具有中性或者阳离子性,进一步具有疏水性等性质。进一步地,引流管等是置入体内物,要求其具有抗菌性,期望在其表面引入银等赋予此功能。
本发明是在改性对象物的表面上形成聚合物链后,进一步地对其聚合物链施行中性化、疏水化、阳离子化、抗菌化等功能化处理的表面改性方法,可根据用途等提供具有期望性能或功能的聚合物刷。所以,在获得对于滑动性或重复滑动的耐久性、密封性的同时,通过银或氟化合物等的处理也可赋予其抗菌性或疏水性,同时对于中性化或阳离子化等其他的功能,也可通过使具有这样的功能的化合物与聚合物链反应的方法来赋予聚合物链此功能。因此,根据本发明,可容易地提供具有期望的功能的注射器用密封垫片、引流管、轮胎等表面改性弹性体。
工序1中,在硫化成形后的橡胶或者成形后的热塑性弹性体(改性对象物)的表面形成聚合引发点。
上述硫化橡胶或者热塑性弹性体优选具有与双键邻接的碳原子(烯丙位碳原子)。
作为改性对象物的橡胶举例有丁苯橡胶、丁二烯橡胶、异戊橡胶、天然橡胶、脱蛋白天然橡胶等的二烯系橡胶,及含有百分之几的异戊二烯单元作为不饱和度的丁基橡胶、卤化丁基橡胶等。从来自硫化橡胶的提取物少这方面考虑,丁基橡胶、卤化丁基橡胶优选由三嗪交联所成橡胶。此时,可以含有酸受体,合适的酸受体举例有铝碳酸镁、碳酸镁。
其他橡胶优选用硫进行硫化。此时,可以添加用硫硫化时通常使用的硫化促进剂、氧化锌、填料、硅烷偶联剂等的混合剂。填料可以适宜地使用炭黑、二氧化硅、粘土、滑石、碳酸钙等。
另外,橡胶的硫化条件适当地设定即可,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。
热塑性弹性体举例有例如,通过可塑性成分(硬链段)的集结发挥交联点的作用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);具有橡胶弹性的高分子化合物,由热塑性成分及橡胶成分混合,通过交联剂进行动态交联而成(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混合聚合物等热塑性弹性体(TPV)等)。
此外,其他合适的热塑性弹性体举例有尼龙、聚酯、聚氨酯、聚丙烯及它们的动态交联热塑性弹性体。动态交联热塑性弹性体优选使卤化丁基橡胶在热塑性弹性体中进行动态交联得到的弹性体。此时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。
关于聚合引发点,例如,通过使光敏剂吸附在改性对象物的表面上而形成。光敏剂举例有例如,羰基化合物、二硫化四乙基秋兰姆等有机硫化合物、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。
作为光敏剂的羰基化合物优选二苯甲酮及其衍生物,例如可以适宜地使用下述式(1)表示的二苯甲酮系化合物。
【化2】
(式(1)中,R1~R5及R1′~R5′相同或不同,表示氢原子、烷基、卤素(氟、氯、溴、碘)、羟基、伯~叔胺基、巯基或者可以含有氧原子、氮原子或硫原子的烃基,相邻的任意两个可以相互连结,同与它们键合的碳原子一起形成环结构。)
二苯甲酮系化合物的具体例举例有二苯甲酮、氧杂蒽酮、9-芴酮、2,4-二氯二苯甲酮、邻苯甲酰安息香酸甲酯、4,4′-双(二甲基氨基)二苯甲酮、4,4′-双(二乙基氨基)二苯甲酮等。其中,从良好地得到聚合物刷的观点看,特别优选二苯甲酮、氧杂蒽酮、9-芴酮。
二苯甲酮系化合物可以适宜地使用氟代二苯甲酮系化合物,举例有例如下述式所示的2,3,4,5,6-五氟二苯甲酮、十氟二苯甲酮等。
【化3】
将二苯甲酮系化合物等的光敏剂吸附在改性对象物表面的方法使用公知的方法即可。例如,对于二苯甲酮系化合物,将二苯甲酮系化合物溶解于有机溶剂中,用得到的溶液对对象物要改性的表面部位进行处理,从而吸附在表面,根据需要,通过干燥使有机溶剂蒸发,形成聚合引发点。表面处理方法只要是可以使该二苯甲酮系化合物溶液与改性对象物的表面接触即可,没有特别的限定,合适的有例如涂覆、喷涂该二苯甲酮系化合物溶液、将其浸渍于该溶液中等。另外,只有一部分的表面需要进行表面改性时,只在所需要的一部分的表面吸附敏化剂即可,此时,合适的是例如涂覆该溶液、喷涂该溶液等。所述溶剂可以使用甲醇、乙醇、丙酮、苯、甲苯、甲基乙基甲酮、乙酸乙酯、THF等,从不会使改性对象物膨胀、干燥、蒸发快这方面考虑,优选丙酮。
优选采用二苯甲酮系化合物溶液对改性对象部位实施表面处理,使光敏剂吸附后,进一步地用光照射改性对象物的表面使吸附的光敏剂与表面进行化学键合。例如照射波长300~450nm(优选300~400nm,更优选350~400nm)的紫外线,可以将二苯甲酮系化合物固定在表面上。所述工序1及上述固定中,橡胶表面的氢被夺取,二苯甲酮的C=O的碳与橡胶表面的碳形成共价键,同时被夺取的氢与C=O的氧键合,形成C-O-H。此外,该抽氢反应由于是由改性对象物的烯丙位的氢选择性进行的,所以橡胶优选是含有烯丙基氢的丁二烯、异戊二烯单元的物质。
【化4】
R:氢或者碳原子数1~4的烷基
其中,优选用光敏剂处理改性对象物的表面,使该光敏剂吸附在表面,接着通过对处理后的表面照射300~400nm的LED光形成聚合引发剂,尤其是,采用二苯甲酮系化合物溶液对改性对象物的表面实施表面处理使光敏剂吸附后,进一步地优选对处理后的表面照射300~400nm的LED光,使吸附的光敏剂与表面进行化学键合。在这里,LED光的波长以355~380nm为适宜。
工序2中,以上述聚合引发点为起点进行单体自由基聚合,使聚合物链于上述改性对象物的表面生长。
单体根据赋予在工序2~3中制造的聚合物链的性能或功能,可以适当选择,例如,举例有取代基或侧链等具有离子性基团的离子性单体。此时,工序2中,制造出发挥源于离子性单体的滑动性等功能的聚合物链,与此同时,在工序3中,容易地追加赋予其抗菌性、疏水性等功能。
离子性单体举例有例如,具有铵、鏻等正电荷的单体(阳离子性单体);具有磺酸基、羧基、磷酸基、膦酸基等负电荷,或者能在负电荷中分解的酸性基的单体(负离子性单体)。
离子性单体的具体例,举例有丙烯酸、甲基丙烯酸酯、衣康酸、3-乙烯丙酸、乙烯磺酸、2-磺基乙基(甲基)丙烯酸酯、3-磺基丙基(甲基)丙烯酸酯、2-丙烯酰胺-2-甲基丙烷磺酸、苯乙烯磺酸;烯丙基胺,2-二甲基氨基乙基(甲基)丙烯酸酯;3-三甲基铵丙基(甲基)丙烯酸酯,3-三甲基铵丙基(甲基)丙烯酰胺等。其中,从通过工序2~3能赋予其各种功能出发,优选丙烯酸、甲基丙烯酸酯。这些可以单独使用也可以2种以上并用。
作为工序2的单体的自由基聚合的方法,可以是将单体(液体)或其溶液涂覆(喷雾)在吸附或者共价键合有二苯甲酮系化合物等的改性对象物的表面,,或者是将该改性对象物浸渍在单体(液体)或其溶液中,通过照射紫外线等光,进行自由基聚合(光自由基聚合),使聚合物链生长于该改性对象物表面上。进一步,也可以在所述涂覆后,用透明的玻璃、PET、聚碳酸酯等覆盖表面,通过从上照射紫外线等光,进行自由基聚合(光自由基聚合),使聚合物链生长于改性对象物表面上。
工序2优选通过光照射添加了还原剂或抗氧化物质的单体进行自由基聚合(光自由基聚合)。此时,还原剂或抗氧化物质会补充系统内的氧,因而优选。添加有还原剂或抗氧化物质的单体中,其各个成分可以是混合的,也可以是分开的。此外,可以使单体先与工序1得到的改性对象物接触之后,再往里添加还原剂、抗氧化物质,也可以预先混合所述成分,再使其混合材料与该改性对象物接触。
具体地,可使工序1得到的由光敏剂在表面形成了聚合引发点的改性对象物,与在单体(液体)或其溶液中添加还原剂或抗氧化物质的溶液得到的物质接触后(浸渍、涂覆等),或者使该改性对象物与单体(液体)或其溶液接触,再在其上放置还原剂或抗氧化物质的溶液后,通过光照射实施自由基聚合,形成聚合物链。
还原剂、抗氧化物质无特别限定,可以适宜地使用具有这样的作用的化合物。举例有例如视黄醇、脱氢视黄醇、乙酸视黄醇、十六烷酸视黄醇、视黄醛、视黄酸、维他命A油等的维他命A类、其衍生物及其盐;α-胡萝卜素、β-胡萝卜素、γ-胡萝卜素、隐黄素、虾青素、墨角藻黄质等类胡萝卜素类及其衍生物;吡哆醇、吡哆醛、吡哆醛-5-磷酸酯、吡哆胺等的维他命B类、其衍生物及其盐;抗坏血酸、抗坏血酸钠、抗坏血酸硬脂酸酯、抗坏血酸棕榈酸酯、抗坏血酸二棕榈酸酯、抗坏血酸磷酸镁等维他命C类、其衍生物及其盐;麦角钙化醇、胆骨化醇、1,2,5-二羟基胆骨化醇等维他命D类、其衍生物及其盐;α-生育酚、β-生育酚、γ-生育酚、δ-生育酚、α-生育三烯酚、β-生育三烯酚、γ-生育三烯酚、δ-生育三烯酚、生育酚醋酸酯、生育酚烟酸酯等维他命E类、其衍生物及其盐;水溶性维生素E(Trolox)、其衍生物及其盐;二羟基甲苯、丁基羟基甲苯、丁基羟基苯甲醚、二丁基羟基甲苯、α-硫辛酸、脱氢硫辛酸、谷胱甘肽、其衍生物及其盐;尿酸、异抗坏血酸、异抗坏血酸钠等异抗坏血酸、其衍生物及其盐;没食子酸、没食子酸丙酯等没食子酸、其衍生物及其盐;芸香苷、α-糖基芸香苷等芸香苷、其衍生物及其盐;色氨酸、其衍生物及其盐;组氨酸、其衍生物及其盐;N-乙酰基半胱氨酸、N-乙酰基高半胱氨酸、N-辛酰基半胱氨酸、N-乙酰基半胱氨酸甲酯等半胱氨酸衍生物及其盐;N,N’-二乙酰基胱氨酸二甲酯、N,N’-二辛酰基胱氨酸二甲酯、N,N’-二辛酰基高胱氨酸二甲酯等胱氨酸衍生物及其盐;肌肽、其衍生物及其盐;高肌肽、其衍生物及其盐;鹅肌肽、其衍生物及其盐;β-丙氨酰组胺(carcinine)、其衍生物及其盐;含有组氨酸及/或色氨酸及/或组胺的二肽或三肽衍生物及其盐;二氢黄酮、黄酮、花青苷、花青素、黄酮醇、五羟黄酮、槲皮苷、杨梅素、非瑟酮、金缕梅单宁、儿茶素、表儿茶素、没食子儿茶素、表没食子儿茶素、表儿茶素没食子酸酯、表没食子儿茶素没食子酸酯等的类黄酮类;单宁酸、咖啡酸、阿魏酸、原儿茶酸、查耳酮、谷维素、鼠尾草酚、芝麻酚、芝麻素、芝麻酚林、姜油酮、姜黄素、四氢姜黄素、3-(3,4-二羟基苯基)-2-(3-(3,4-二羟基苯基)丙烯酰胺基)丙酸(Clovamide)、脱氧3-(3,4-二羟基苯基)-2-(3-(3,4-二羟基苯基)丙烯酰胺基)丙酸(deoxyclovamide)、生姜酚、辣椒素、香草酰胺、鞣花酸、溴苯酚、灰绿曲霉黄色素(flavoglaucin)、蛋白黑素、核黄素、核黄素丁酸酯、黄素单核苷酸、黄素腺嘌呤核苷酸、辅酶(Ubiquinone),泛醇(Ubiquinol)、甘露醇、胆红素、胆固醇、依布硒、硒蛋氨酸、铜蓝蛋白、转铁蛋白、乳铁蛋白、白蛋白、超氧化歧化酶,过氧化氢酶,谷胱甘肽过氧化酶,金属硫蛋白,O-膦酰基亚吡啶醇若丹明等。它们可以单独使用或两种以上并用。
其中,出于氧的补充能力高的理由,优选核黄素、抗坏血酸、α-生育酚、β-胡萝卜素、尿酸,特别优选核黄素、抗坏血酸。
使用还原剂、抗氧化物质的溶液时,该还原剂、抗氧化物质的浓度优选10-4~1质量%,更优选10-3~0.1质量%。此外,自由基聚合性单体的使用量根据形成的聚合物链的长度、该链发挥的功能等适当地设定即可。此外,还原剂、抗氧化物质的使用量也可从体系内的氧的补充等方面考虑进行适当地设定。
粉刷(喷雾)溶剂、粉刷(喷雾)方法、浸渍方法、照射条件等可以采用传统公知的材料及方法。另外,自由基聚合性单体的溶液使用其溶解于水溶液或溶解于使用的光敏剂(二苯甲酮系化合物等)不溶的有机溶剂中得到的溶液。此外,自由基聚合性单体(液体)、其溶液也可以使用含有4-甲基苯酚等公知的聚合抑制剂的物质。
本发明中,涂覆单体(液体)或者其溶液后,或者浸渍于单体或者其溶液中后,通过光照射,进行单体的自由基聚合,主要地可适当使用紫外光中具有发光波长的高压水银灯、金属卤化物灯、LED灯等UV照射光源。照射光量考虑聚合时间或反应进行的均一性后适当设定即可。此外,为了防止反应容器内的氧等活性气体阻碍聚合,优选在光照射时或光照射前,除去反应容器内或反应液中的氧。因此,如下适当地进行,在反应容器内或反应液中导入氮气或氩气等非活性气体,将氧等活性气体排到反应体系外,将反应体系内置换成非活性气体气氛等。进一步地,为了防止氧等阻碍反应,也可以考虑如下进行,将UV照射光源设置于玻璃或塑料等的反应容器与反应液或改性对象物之间的空气层(氧含量在15%以上)进不来的位置等。
照射紫外线时,其波长优选300~450nm,更优选300~400nm。由此,改性对象物的表面可以良好地形成聚合物链。光源可以使用高压水银灯或具有365nm的中心波长的LED、具有375nm的中心波长的LED等。其中,优选使用300~400nm的LED光照射,更优选355~380nm的LED光照射。从效率方面考虑,特别优选具有365nm的中心波长的LED等,其接近二苯甲酮的激发波长366nm。
工序2中形成的聚合物链的长度优选为10~50000nm,更优选为100~50000nm。若不足10nm,则存在得不到良好的滑动性的倾向。若超过50000nm,则不能期待滑动性进一步提高,使用高价的单体而存在原料成本上升的倾向,还有,导致用肉眼能看到表面处理带来的表面花纹,而有损美观,或者存在密封性降低的倾向。
所述工序2中,可以以聚合引发点为起点,使两种以上的单体进行自由基聚合,也可以使多种聚合物链在改性对象物的表面生长。本发明的表面改性方法可以使聚合物链间进行交联。此时,聚合物链间可以形成离子交联,通过具有氧原子的亲水性基团形成交联,通过具有碘等卤素基团的化合物形成交联。
工序3中,对工序2中形成的聚合物链实施功能化处理。该工序3,进一步地对形成的聚合物链添加功能,例如,根据需要,使聚合物链的侧链的功能团与氨水等接触后,转换为盐,使该功能团与具有其他功能团等功能性基的化合物反应等,适当选择方法添加期望的性能或功能,制造成并有各种功能的表面改性弹性体。
例如,工序2中,丙烯酸或甲基丙烯酸酯聚合后制成聚(甲基)丙烯酸的聚合物链,需要进一步赋予聚合物链抗菌性时,通过工序3中,令(甲基)丙烯酸与抗菌性金属盐进行盐转换,将抗菌性金属并入聚合物链即可。盐转换可以使用公知的方法,例如,通过聚合物链与抗菌性金属盐的水溶液(银盐的水溶液或氨水溶液,金在王水中溶解的溶液等)接触的方法等(浸渍,涂敷等)实施。
抗菌性金属盐,举例有金、银、铜、铂、锌、镍、锰、钴、锡等抗菌性金属的硫酸盐、碳酸盐、醋酸盐、硝酸盐、卤化盐、氢氧化物等的盐。其中,因为价格低且安全性高,优选银盐。
银盐(银化合物)的具体例,举例有醋酸银、碳酸银、甲酸银、丙酸银、酪酸银、柠檬酸银、乳酸银等有机酸银;氯化银、碘化银、溴化银、氟化银等卤化银;碳酸银、硫酸银、硝酸银、亚硝酸银、氯酸银、过氯酸银等无机酸银等。锌盐(锌化合物)的具体例,举例有硫酸锌、氯化锌、醋酸亚铅等。铜盐(铜化合物)的具体例,举例有硫酸铜、氯化铜、氢氧化铜、乙酸铜等。同时,还可以使用金、铂、镍、锰、钴、锡等其他公知的金属盐。这些可以单独使用,也可以2种以上并用。
另外,对于工序2中制成的聚(甲基)丙烯酸的聚合物链,进一步地赋予该聚合物链碱性、中性或者阳离子性时,通过工序3中,令聚(甲基)丙烯酸与碱性盐进行盐转换,将碱性金属并入聚合物链即可。盐转换可以使用公知的方法,例如,通过使聚合物链与碱性盐的水溶液接触的方法等实施。
碱性盐举例有钠、钾、锂盐等碱金属盐;镁、钙盐等碱土类金属盐等。具体地,碱金属盐举例有碱金属的无机酸盐、碳酸盐、磷酸盐等,例如氯化锂、硝酸锂、硫酸锂、碳酸锂、过盐酸锂、氯化钠、碳酸氢钠、硝酸钠、碳酸钠、硫酸钠、硫酸钠、亚硫酸钠、过氯酸钠、硝酸钾、硫酸钾、碳酸钾、氯化钾、溴化钾等。碱土类金属盐可列举碱土类金属的无机酸盐、碳酸盐、磷酸盐等,例如可举例硫酸钙、硝酸钙、氯化钙、硫酸镁等。这些可以单独使用也可以2种以上并用。
此外,通过在工序2中制成聚(甲基)丙烯酸的聚合物链,在工序3中使聚(甲基)丙烯酸与胺化合物发生酰胺化反应,也可以导入胺化合物中的功能性基团(各种功能团等)。例如,赋予工序2中制成的聚合物链疏水性时,在工序3中使聚(甲基)丙烯酸与氟系胺化合物发生酰胺化反应,使氟系胺化合物并入聚合物链中即可。酰胺化可以使用公知的方法,例如,在硫酸等酸的存在下,实施使聚合物链的羧基与氟系胺化合物等胺化合物的氨基反应,导入氟代烷基等功能性基团(功能团)的方法。进一步地,可以实施使用缩合剂使聚合物链的羧基与氟系胺化合物等胺化合物的胺基缩合,转化为酰胺的方法或聚合物链的羧基经亚硫酰氯氯化,此时使该胺化合物的胺基在氢氧化钠等碱性条件下缩合转化为酰胺的方法等。
此外,在工序2中制成聚(甲基)丙烯酸的聚合物链,在工序3中使聚(甲基)丙烯酸与具有羟基的化合物发生酯化反应,可以导入具有羟基化合物中的功能性基团(各种功能团等)。例如,实施使聚合物链的羧基与氟系具有羟基的化合物等具有羟基化合物的羟基在酸存在下缩合,酯化的方法等。
氟系胺化合物可以使用氟化有机脂肪族胺等,例如举例有下式显示的化合物等。
CF3(CF2)n-(CX2)p-NH2-m((CF2)nCF3)m
(式中X表示氢或氟。n表示相同或者不同的1~10的整数。m表示0~2的整数。p表示0~4的整数。)
氟化脂肪族胺的具体例,举例有2,2,2-三氟乙基胺、2,2,3,3,3-五氟丙基胺、2,2,3,3,4,4,4-七氟丁基胺、2,2,3,3,4,4,5,5,5-九氟戊基胺、2,2,3,3,4,4,5,5,6,6,6-十一氟己基胺、三氟甲基胺、全氟乙基胺、全氟丙基胺、全氟丁基胺、全氟戊基胺、全氟己基胺、全氟庚基胺、全氟辛基胺、全氟癸基胺、二氟乙醇胺等。这些可以单独使用,也可以2种以上并用。
氟系含羟基化合物,举例有1H,1H-七氟-1-丁醇(CF3CF2CF2CH2OH)、1H,1H-九氟-1-戊醇(CF3(CF2)3CH2OH)、1H,1H-全氟-1-壬醇(CF3(CF2)7CH2OH)、1H,1H-2,5-二(三氟甲基)-3,6-二恶十一氟壬醇(CF3CF2CF2OCF(CF3)CF2OCF(CF3)CH2OH)、3,3,3-三氟-1-丙醇(CF3CH2CH2OH)、3,3,4,4,4-五氟-1-丁醇(CF3CF2CH2CH2OH)、3,3,4,4-四氟-3-(三氟甲基)-1-丁醇(CF3CF(CF3)CH2CH2OH)、1H,1H,2H,2H-九氟-1-己醇(CF3(CF2)3CH2CH2OH)、1H,1H,2H,3H,3H-全氟-1,2-壬二醇(CF3(CF2)5CH2CH(OH)CH2OH)、1H,1H,2H,3H,3H-全氟-1,2-十一二醇(CF3(CF2)7CH2CH(OH)CH2OH)。
这些可以单独使用,也可以两种以上并用。
通过在硫化橡胶或热塑性弹性体上应用所述表面改性方法,能够得到表面改性弹性体。得到的表面改性弹性体在水存在的条件下或在干燥状态下,其滑动性优异,由于是低摩擦、水的阻力小这些方面也优异。进一步,也可以赋予抗菌性金属盐、疏水性、中性、阳离子性等期望的功能。此外,通过在三维形状的固体(弹性体等)的至少一部分应用所述方法,能够得到经改性的表面改性弹性体。进一步地,该表面改性弹性体的优选例举例有聚合物刷(高分子刷)。在这里,聚合物刷是指经由表面引发活性自由基聚合的接出(graftingfrom)式接枝聚合物。此外,接枝链定向在大致垂直于改性对象物的表面的方向上,使熵减小,接枝链的分子运动降低,由此得到滑动性,因而优选。此外,作为刷密度,优选0.01链/nm2以上的准浓度及浓度刷。
此外,通过在硫化橡胶或热塑性弹性体上应用所述表面改性方法,能够制造具有至少一部分经改性的表面的注射器用密封垫片。优选至少对密封垫片表面的滑动部实施改性,也可以对整个表面实施改性。
图1是注射器用密封垫片的实施方式的侧面图的一例。图1所示的密封垫片1,其与注射器的注射筒内周面接触的外周面上具有连续的向圆周方向突出的三个环状突起部11a、11b、11c。在密封垫片1中,作为适用所述表面改性的部位,举例有:(1)环状突起部11a、11b、11c等的与注射筒接触的突起部表面、(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面部的表面13等。
同样地,通过在硫化橡胶或热塑性弹性体上应用所述表面改性方法,能够制造具有至少一部分经改性的引流管。优选至少对引流管表面与体液接触部分实施改性,也可以对整个表面实施改性。
另外,在小汽车等车辆所使用的轮胎胎面上形成的槽上应用所述表面改性方法,使聚合物刷在槽上生成,由此使得在湿地或雪上路面,槽表面的流体阻力下降,或者与水的接触角增大,所以能够提高排水或排雪,改善抓地性。
图2是充气轮胎(整体未图示)的胎面部2的展开图的一例,图3表示图2的A1-A1截面图。图2~3中,中央纵槽3a(槽深度D1)、胎肩纵槽3b(槽深度D2)由沿轮胎周向呈直线状延伸的直槽构成。这样的直槽其排水阻力小,在直线行驶时能够发挥很高的排水性能。
此外,充气轮胎设置有于胎肩纵槽3b侧沿轮胎周向延伸的细槽5(槽深度D3)、从该细槽5向中央纵槽3a倾斜地延伸的中间倾斜槽6(槽深度D4)、比细槽5还位于轮胎轴向内侧的且在轮胎周向上将相邻的中间倾斜槽6、6间连接的连接槽7(槽深度D5)、从胎肩纵槽3b朝向轮胎外部的胎肩横槽8、8a、8b(槽深度D6)等,这样的槽也能够发挥排水性能。并且,通过对这些槽应用所述方法,上述效果得以发挥。
实施例
根据实施例,对本发明进行具体说明,但本发明并不限于此。
实施例1
用三嗪将含有异戊二烯单元的氯化丁基橡胶(不饱和度:1~2%)进行交联得到硫化橡胶(在180℃下硫化10分钟),将该硫化橡胶浸渍于二苯甲酮的1wt%丙酮溶液中,使二苯甲酮吸附在硫化橡胶表面。然后,取出硫化橡胶干燥。接着,对硫化橡胶表面照射10分钟的具有365nm的波长的LED光,使二苯甲酮与其形成化学键。然后,用丙酮洗涤表面除去未反应的二苯甲酮。
将干燥后的硫化橡胶浸渍在置有丙烯酸水溶液(2.5M:18g的丙烯酸溶解在100mL水中)的玻璃反应容器中,之后加入核黄素水溶液(浓度0.0093mmol/L)。水溶液不与液态单体相溶,并且水溶液的比重轻于液态单体,故形成分离于上层的状态。然后在具有365nm波长的LED光下照射1小时紫外线进行自由基聚合,使聚合物链在橡胶表面上成长。
将得到的聚合物链表面上形成的硫化橡胶浸渍在硝酸银水溶液(0.01M)中5小时后,在水中洗涤,使其干燥,制成表面改性弹性体(聚合物刷)。
实施例2
将得到的聚合物链表面上形成的硫化橡胶浸渍在氨水(0.01M)中2小时后,在水中洗涤,使其浸渍在硝酸银水溶液中,实施与实施例1同样的方式,制作表面改性弹性体(聚合物刷)。
实施例3
除了将硝酸银水溶液变更为碳酸银的氨·稀硝酸水溶液之外,实施与实施例1同样的方式,制作表面改性弹性体(聚合物刷)。
实施例4
除了将硝酸银水溶液变更为氯化银的氨水溶液之外,实施与实施例1同样的方式,制作表面改性弹性体(聚合物刷)。
实施例5
用三嗪将含有异戊二烯单元的氯化丁基橡胶(不饱和度:1~2%)进行交联得到硫化橡胶(在180℃下硫化10分钟),将该硫化橡胶浸渍于二苯甲酮的1wt%丙酮溶液中,使二苯甲酮吸附在硫化橡胶表面。然后,取出硫化橡胶干燥。接着,对硫化橡胶表面照射10分钟的具有365nm的波长的LED光,使二苯甲酮与其形成化学键。然后,用丙酮洗涤表面除去未反应的二苯甲酮。
将干燥后的硫化橡胶浸渍在置有丙烯酸水溶液(2.5M:18g的丙烯酸溶解在100mL水中)的玻璃反应容器中,之后加入核黄素水溶液(浓度0.0093mmol/L)。水溶液不与液态单体相溶,并且水溶液比重轻于液态单体,故形成分离于上层的状态。然后在具有365nm波长的LED光下照射1小时紫外线进行自由基聚合,使聚合物链在橡胶表面上成长。
得到的聚合物链的表面上形成的硫化橡胶中,聚合表面的丙烯酸的侧链的羧基(COOH基),与1H,1H-全氟庚基胺(CF3(CF2)5CH2NH2),在硫酸存在下进行酰胺化反应(6小时),然后,对其洗涤,制作表面改性弹性体(聚合物刷)。
比较例1
使用用三嗪将氯化丁基橡胶进行交联得到的硫化橡胶(在180℃下硫化10分钟)。
采用以下的方法对实施例、比较例制作的表面改性弹性体进行评价。
(聚合物链的长度)
关于硫化橡胶表面形成的聚合物链的长度,使用SEM,在加速电压15kV、1000倍的条件下,对形成有聚合物链的改性橡胶截面进行测定。将拍摄的聚合物层的厚度作为聚合物链的长度。
(静摩擦系数及动态摩擦系数)
依据ASTM D 1894规定的方法,测定表面改性弹性体的表面的静摩擦系数、动态摩擦系数,以及分别滴下200μL水的样品表面的静摩擦系数、动态摩擦系数。另外,使样品与硼硅酸盐玻璃接触,测定与硼硅酸盐玻璃之间的摩擦力。另外,在以下条件下进行测定,测定摩擦系数用的负荷为200g,拉伸速度为600mm/min,跑道距离为10cm。装置使用HEIDON型号14(新东科学(株)制)。
(银的分析)
对于在实施例中制作的聚合物刷,通过SEM-EDX进行元素分析来调查银的引入。
表1
实施例的表面改性弹性体表面,静摩擦系数、动态摩擦系数大幅下降,确定其得到良好的滑动性。同时,因为只对表面进行了改性,其密封性与比较例1相同。进一步地,对于实施例,可确认银的引入。
因此,用于注射器的柱塞的密封垫片时,具有充分的密封性,同时柱塞对于注射筒的摩擦力减轻,能够容易且正确地进行注射器的处理(操作)。另外,由于静摩擦系数与动态摩擦系数之差小,所以开始按压柱塞和之后的柱塞进入的动作能够顺利地进行,而没有跳动。另外,用热塑性弹性体制作注射器的注射筒,使聚合物链在其内表面生长时,与上述一样,也能够容易地进行注射器的处理。
同时,用于引流管时,不仅有滑动性,还得到银的抗菌性。进一步地,转换为盐后,少有对药液或体内的不良影响。
此外,通过在小汽车等使用的轮胎胎面形成的槽、胎侧、隔膜、滑雪板或滑雪板的滑走面、泳衣、道路标识、看板等的表面形成聚合物链,也能够期待上述效果。
Claims (27)
1.一种表面改性方法,以具有与双键邻接的碳原子即烯丙位碳原子的硫化橡胶或者热塑性弹性体为改性对象物,该方法包含:
工序1,在上述改性对象物表面上,通过使光敏剂吸附,并对改性对象物的表面照射300~400nm的LED光,由上述表面上的光敏剂形成聚合引发点,
和工序2,以上述聚合引发点为起点,照射300~400nm的LED光使单体进行自由基聚合,从而使聚合物链在上述改性对象物表面生长,
和工序3,功能化处理上述聚合物链,
所述光敏剂是下述式(1)表示的二苯甲酮系化合物,
【化1】
式(1)中,R1~R5及R1′~R5′相同或不同,表示氢原子、烷基、卤素、羟基、伯~叔胺基、巯基或者含有氧原子、氮原子或硫原子的烃基,相邻的任意两个相互连结,与同它们键合的碳原子一起形成环结构。
2.根据权利要求1所述的表面改性方法,所述工序2中,在上述单体自由基聚合时,添加还原剂或者抗氧化物质。
3.根据权利要求2所述的表面改性方法,所述还原剂或者抗氧化物质是选自由核黄素、抗坏血酸、α-生育酚、β-胡萝卜素及尿酸所构成群中的至少1种。
4.根据权利要求1~3任一项所述的表面改性方法,在进行所述光照射时或照射前,将非活性气体导入反应容器及反应液中,将其置换成非活性气体气氛,使之聚合。
5.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,将所述聚合物链的侧链转换为盐。
6.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,将所述聚合物链的侧链使用碱金属盐或者抗菌性金属盐转换为盐。
7.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,所述聚合物链的侧链经过与氨水接触后转换为盐。
8.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,将所述聚合物链的侧链使用碱性盐转换为盐。
9.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,将所述聚合物链的侧链使用硝酸盐、碳酸盐或者卤化盐转换为盐。
10.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,将所述聚合物链的侧链使用硝酸银、碳酸银或者氯化银转换为盐。
11.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,使所述聚合物链的侧链中的羧酸基与胺化合物反应形成酰胺键,导入功能性基团。
12.根据权利要求1~3任一项所述的表面改性方法,所述工序3中,使所述聚合物链的侧链中的羧酸基与具有羟基的化合物反应形成酯键,导入功能性基团。
13.根据权利要求11所述的表面改性方法,所述功能性基团为氟代烷基。
14.根据权利要求12所述的表面改性方法,所述功能性基团为氟代烷基。
15.根据权利要求11所述的表面改性方法,所述胺化合物为下式所示化合物,
CF3(CF2)n-(CX2)p-NH2-m((CF2)nCF3)m
式中,X表示氢或氟,n表示相同或者不同的1~10的整数,m表示0~2的整数,p表示0~4的整数。
16.根据权利要求13或14所述的表面改性方法,所述胺化合物为下式所示化合物,
CF3(CF2)n-(CX2)p-NH2-m((CF2)nCF3)m
式中,X表示氢或氟,n表示相同或者不同的1~10的整数,m表示0~2的整数,p表示0~4的整数。
17.根据权利要求1~3、13~15任一项所述的表面改性方法,所述自由基聚合性单体液体或者其溶液含有聚合抑制剂,在该聚合抑制剂存在下使其聚合。
18.根据权利要求17所述的表面改性方法,所述聚合抑制剂为4-甲基苯酚。
19.根据权利要求1~3、13~15、18任一项所述的表面改性方法,所述聚合物链的长度为10~50000nm。
20.一种表面改性弹性体,通过权利要求1~19任一项所述的表面改性方法得到。
21.一种表面改性弹性体,通过权利要求1~19任一项所述表面改性方法得到,要求具有在水存在下或干燥状态下的滑动性、低摩擦或低的水阻力。
22.一种表面改性弹性体,通过权利要求1~19任一项所述的表面改性方法得到,要求具有抗菌性。
23.一种表面改性弹性体,其三维形状的固体表面的至少一部分被权利要求1~19任一项所述的表面改性方法改性。
24.根据权利要求20~23任一项所述的表面改性弹性体,其为聚合物刷。
25.一种注射器用密封垫片,其具有至少一部分由权利要求1~19任一项所述的表面改性方法改性的表面。
26.一种引流管,其具有至少一部分由权利要求1~19任一项所述的表面改性方法改性的表面。
27.一种轮胎,其具有至少一部分由权利要求1~19任一项所述的表面改性方法改性的轮胎的槽表面。
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EP2623335B1 (en) | 2018-03-14 |
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