CN101379168A - 纳米颗粒组合物、其制备方法及用途 - Google Patents
纳米颗粒组合物、其制备方法及用途 Download PDFInfo
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- CN101379168A CN101379168A CNA2007800050530A CN200780005053A CN101379168A CN 101379168 A CN101379168 A CN 101379168A CN A2007800050530 A CNA2007800050530 A CN A2007800050530A CN 200780005053 A CN200780005053 A CN 200780005053A CN 101379168 A CN101379168 A CN 101379168A
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Abstract
本发明揭露了包括固体润滑剂纳米颗粒和有机介质的组合物。还揭露了包括层状材料的纳米颗粒。提供了一种通过研磨层状材料制造纳米颗粒的方法。还揭露了一种制造润滑剂的方法,该方法包括研磨层状材料以形成纳米颗粒和将纳米颗粒掺入基体以形成润滑剂。
Description
技术领域
相关申请的交互参考
本申请要求2006年1月12日提交的美国临时申请No.60/758,307的优先权,该专利文献全文并入此处作为参考。
联邦赞助的研究或开发声明
有关该申请主题的努力得到国家科学基金(National ScienceFoundation)(NSF/DMI 0115532)准予的部分支持。政府对该申请的任何专利具有确定的权利。
背景技术
在过去很多年中,花费了相当大的力气研制可用作润滑剂、涂料、或输送剂(delivery mechanism)的纳米结构。探寻改进纳米组合物、其制造方法及用途的新途径。
发明内容
概述
一方面,描述了组合物,其包含固体润滑剂纳米颗粒和有机介质。
另一方面,揭露了包括层状材料的纳米颗粒。
在进一步的方面中,提供了制造包含研磨层状材料(milling layeredmaterial)的纳米颗粒的方法。
再一方面,揭露了制造润滑剂的方法,其中该方法包括研磨层状材料以形成纳米颗粒,并将纳米颗粒掺入基体以形成润滑剂。
参考详细说明和附图,其它方面将会变得很清楚。
附图说明
图1是图示说明制造固体润滑剂纳米颗粒的方法的图。
图2是图示说明一种制备纳米颗粒基润滑剂的方法的图。
图3显示二硫化钼颗粒的透射电子显微镜(TEM)照片。图3(A)显示典型地可获得的约几微米至亚微米大小的二硫化钼。图3(B)显示在空气中球磨48小时的二硫化钼。图3(C)是显示在空气中球磨48小时的二硫化钼的高分辨电子显微镜照片。图3(D)是显示在空气中球磨48小时,然后在油中球磨48小时的二硫化钼的高分辨透射电子显微镜(HRTEM)照片。
图4是显示二硫化钼颗粒的XRD光谱的图。图4(A)是在空气中球磨48小时,然后在油中球磨48小时的二硫化钼的XRD光谱。图4(B)是在空气中球磨48小时的二硫化钼的XRD光谱。图4(C)是未进行球磨的二硫化钼的XRD光谱。
图5是显示二硫化钼颗粒的XPS光谱的图。显示了未进行球磨的二硫化钼的碳峰,以及在空气中球磨48小时,然后在油中球磨48小时的二硫化钼的碳峰。
图6显示描述了石蜡油中不同添加剂的摩擦试验数据的图和条形图。图6(A)显示了基油(石蜡油)、具有微尺寸MoS2的石蜡油、具有在空气中研磨48小时的MoS2的石蜡油、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油的平均磨斑直径。图6(B)显示了不含纳米颗粒添加剂的石蜡油、具有微尺寸MoS2的石蜡油、具有在空气中研磨48小时的MoS2的石蜡油、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油的负荷磨损指数。图6(C)显示了不含纳米颗粒添加剂的石蜡油、具有微尺寸MoS2的石蜡油(c-MoS2)、具有在空气中研磨48小时的MoS2的石蜡油(d-MoS2)、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油(n-MoS2)的COF。图6(D)显示了具有微尺寸MoS2的石蜡油(c-MoS2)、具有在空气中研磨48小时的MoS2的石蜡油(d-MoS2)、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油(n-MoS2)的极压数据。在每次试验中,固体润滑剂纳米颗粒添加剂的量为1重量%。
图7是显示二硫化钼纳米颗粒(15-70nm平均尺寸)结构的TEM图像。图7(A)显示了在空气中球磨48小时的密闭笼致密椭圆形结构的二硫化钼纳米颗粒。图7(B)显示了在空气中球磨48小时然后在菜子油中球磨48小时的开放的端口椭圆形结构的二硫化钼纳米颗粒。
图8是描述石蜡油中不同添加剂的磨斑直径的对比的图。一种添加剂是结晶二硫化钼(c-MoS2)。另一种添加剂是在空气中球磨的二硫化钼纳米颗粒(n-MoS2)。再一种添加剂是在空气中球磨然后在菜子油中球磨的二硫化钼纳米颗粒,并在其中添加磷脂乳化剂(n-MoS2+乳化剂)。
图9显示使用能量分散x射线分析(EDS)形成的照片和图像,其描述了纳米颗粒基润滑剂在四球摩擦试验中的磨斑直径的化学分析。图9(A)显示不含任何纳米颗粒组合物添加剂的石蜡油。图9(B)显示具有在空气中球磨48小时然后在油中球磨48小时并用磷脂乳化剂处理的二硫化钼纳米颗粒的石蜡油。
详细描述
在详细说明任何实施方案前,应理解本发明不限于其结构细节的应用以及在下述描述中或下述图示说明中设定的组分的配置。本发明可以是以多种方式实践或实施的其它实施方案。而且,应理解在本文中使用的词语和术语是用作说明的目的,而不应理解为用于限制本发明。
本文中引用的任何数值范围包括从下限值到上限值的所有值。例如,如果浓度范围表述为1%至50%,其意指例如2%至40%,10%至30%,或1%至3%等值被表述列举在本说明书中。这些只是特别举出的例子,所有可能的数值间的组合和包括列出的最低值和最高值都被认为表述在本申请中。
本文描述了包含固体润滑剂纳米颗粒和有机介质的组合物及其制备方法。也描述了包含层状材料的纳米颗粒。纳米颗粒可以是固体润滑剂纳米颗粒。纳米颗粒可以由原料或固体润滑剂原料制得。固体润滑剂的例子包括,但不限于,层状材料,合适的硫属化合物,更合适地,二硫化钼,二硫化钨,或其组合。其它层状材料是石墨或嵌入石墨。其它可单独使用或与层状材料组合使用的固体润滑剂是聚四氟乙烯(),氮化硼(合适的六方氮化硼),软金属(例如银、铅、镍、铜),氟化铈,氧化锌,硫酸银,碘化镉,碘化铅,氟化钡,硫化锡,磷酸锌,硫化锌,云母,硝酸硼,硼砂,氟化碳,磷化锌,硼,或其组合。氟化碳可以是,但不限于,碳基材料,例如被氟化以改善其美学特征的石墨。所述材料可包括,例如CF.sub.x的材料,其中x为从约0.05至约1.2。该材料由Allied Chemical生产,商标为Accufluor。
方法可包括研磨固体润滑剂进料。在一个实施方案中,固体润滑剂进料可以被研磨成包含约500纳米(亚微米尺寸)至约10纳米平均尺寸的颗粒。合适地,该颗粒可以具有小于或等于约500纳米的平均颗粒尺寸,合适地小于或等于约100纳米,合适地小于或等于约80纳米,和更合适地小于或等于约50纳米。可选择地,球磨可导致得到包含混合物的研磨固体润滑剂颗粒,所述混合物包含具有小于或等于约500纳米的平均颗粒尺寸的颗粒,以及较大的颗粒。在它事情中,研磨可包括球磨和化学机械研磨。球磨的例子可包括干球磨、湿球磨、和其组合。球磨可以指包括两个相互作用物体的碰撞过程,其中一个物体可以是球、棒、4点针(千斤顶(jack)形状)、或其它形状。化学机械研磨可以指可在有机介质和纳米颗粒之间形成络合物的碰撞过程。作为化学机械研磨的结果,有机介质可以包覆、包裹、或***纳米颗粒。
在另一个实施方案中,固体润滑剂进料可以被干研磨,然后湿研磨。可以将乳化剂与基体混合,并添加到湿研磨的颗粒中。干研磨粉(dry milling)可以是指在真空、气体、或其组合存在下研磨的颗粒。湿磨粉(wet milling)可以是指在液体存在下研磨的颗粒。
固体润滑剂纳米颗粒组合物可进一步包含有机介质。有机介质的例子包括,但不限于,油介质、油脂介质、醇介质、或其组合。有机介质的特殊例子包括,但不限于,复合油,菜子油,植物油,大豆油,玉米油,菜子油的乙酯和甲酯,蒸馏的单甘酯,单甘酯,甘油二酯,单甘酯的乙酸酯,单甘酯的有机酸酯,脱水山梨糖醇,脂肪酸的脱水山梨糖酯,脂肪酸的丙二醇酯,脂肪酸的聚甘油酯,正十六烷,烃油,磷脂,或其组合。这些许多有机介质是可以被环境接受的。
组合物可以包含乳化剂、表面活性剂、或分散剂。乳化剂的例子可包括,但不限于,具有约2至约7的亲水-亲油平衡(HLB)的乳化剂;可选择地,约3至约5的HLB;或可选择地,约4的HLB。乳化剂的其它例子包括,但不限于,卵磷脂,大豆卵磷脂,磷脂卵磷脂,洗涤剂,蒸馏的单甘酯,单甘酯,甘油二酯,单甘酯的乙酸酯,单甘酯的有机酸酯,脂肪酸的脱水山梨糖酯,脂肪酸的丙二醇酯,脂肪酸的聚甘油酯,含磷的化合物,含硫的化合物,含氮的化合物,或其组合。
描述了制造润滑剂的方法。组合物可被用作分散在基体中的添加剂。基体的例子包括,但不限于,油、油脂,塑料,凝胶,喷雾(sprays),或其组合。基体的特定例子可包括,但不限于,烃油,植物油,玉米油,花生油,菜子油,大豆油,矿物油,石蜡油,合成油,石油凝胶,石油油脂,烃凝胶,烃油脂,锂基油脂,氟醚基油脂,乙烯基双硬脂酰胺,蜡,硅氧烷,或其组合。
本文描述了润滑或涂覆物体的方法,所述物体为组合物最终应用的一部分,所述组合物包括至少一种固体润滑剂纳米颗粒和有机介质。进一步描述了通过使用组合物润滑物体的方法,所述组合物包括固体润滑剂颗粒和作为输送剂的有机介质。
本文公开了组合物以及制备纳米颗粒基润滑剂的方法,在各种优点中,该润滑剂显示了提高的分散稳定性和抗团聚性。图1图示说明了制备纳米颗粒基润滑剂或组合物的方法。通过管线210,固体润滑剂进料被引至球磨加工机械215。在加工机械215中进行球磨,将固体润滑剂进料研磨成具有小于或等于约500纳米平均颗粒尺寸的颗粒,合适地小于或等于约100纳米,合适地小于或等于约80纳米,和更合适地小于或等于约50纳米。可选择地,球磨可导致得到包含混合物的研磨的固体润滑剂颗粒,所述混合物包含具有小于或等于约500纳米的平均颗粒尺寸的颗粒,以及较大的颗粒。球磨可以是高能球磨,中能球磨,或其组合。此外,在各个实施方案中,球磨在真空下,气体存在下,在液体存在下,在第二固体存在下,或其组合下实施。可将纳米颗粒组合物通过管线220从加工机械中移出。纳米颗粒组合物可以是纳米颗粒基润滑剂。
在可选择的实施方案中,球磨可包括第一球磨和至少一个以上的后续球磨,或球磨和/或其它合适的加工方法。合适地,球磨可包括干研磨,然后湿研磨。图2图示说明制备纳米颗粒基润滑剂的进一步的方法100,其中干研磨后进行湿研磨。进料装置110将固体润滑剂进料引至球磨加工机械115,其中在例如真空或空气中的干球磨将固体润滑剂进料减小至具有上述尺寸的平均尺寸的颗粒。管线120将干研磨的颗粒输送至湿研磨加工机械125。在进入湿研磨加工机械125前,通过管线160,干研磨颗粒与复合油或有机介质结合。可选择地,有机介质和干研磨颗粒可在湿研磨加工机械125中结合。在进一步的可选择的实施方案中(未显示),干研磨和湿研磨可在单个加工机械中实施,其中在初始进行干研磨后,将有机介质供应至单个加工机械用于湿研磨。在其它的可选择的实施方案中,球磨装置中的球可以用有机介质涂覆以将有机介质掺入固体润滑剂纳米颗粒中。
在湿研磨后,管线130将湿研磨的颗粒输送至容器135中,该容器可以是超声设备。可选择地,管线130可输送包含固体润滑剂纳米颗粒、有机介质的混合物,和包含与有机介质结合的固体润滑剂纳米颗粒的络合物。
在另一个实施方案中,将湿研磨的颗粒引入容器135之前,可通过管线150将基体进料至容器135。可选择地,将基体供应至湿研磨加工机械125中,和在湿研磨加工机械125中进行混合(其包括超声)。在该实施方案中,固体润滑剂纳米颗粒组合物可用作添加剂并分散在基体中。根据基体和固体润滑剂纳米颗粒组合物的能力,可将基体与固体润滑剂纳米颗粒组合物配对以进行合适掺合。在该情况下,固体润滑剂纳米颗粒组合物可提高基体的性能。
在进一步的实施方案中,乳化剂可与基体混合。乳化剂可进一步提高固体润滑剂纳米颗粒组合物在基体中的分散性。可选择乳化剂以提高纳米颗粒组合物在基体中的分散稳定性。也可以通过管线140将乳化剂供应至容器135中。在许多实施方案中,在引入湿研磨颗粒前,乳化剂和基体在容器135中结合。在通过均质分散/溶解络合物/纳米颗粒添加固体润滑剂纳米颗粒和有机介质的络合物和/或固体润滑剂纳米颗粒,乳化剂与基体的优先混合可提高分散性。在一些实施方案中,乳化剂与基体的混合可包括超声。可选择地,可将乳化剂供应至湿研磨加工机械125中,且在湿研磨加工机械125中进行混合(其包括超声)。通过管线120从容器135中移出的润滑剂可以是包含湿研磨颗粒、有机介质、和基体的掺合物。该掺合物可进一步包含乳化剂。在其它可选择的实施方案中,在与配合面的相互作用过程中可将添加剂添加至纳米颗粒基润滑剂中。
在进一步的实施方案中,可将抗氧化剂或抗腐蚀剂与固体润滑剂纳米颗粒一起研磨。抗氧化剂的例子包括,但不限于,受阻酚,烷基化酚,烷基胺,芳基胺,2,6-二-叔丁基-4-甲基酚,4,4’-二-叔辛基二苯胺,叔丁基对苯二酚,三(2,4-二-叔丁基苯基)磷酸酯,亚磷酸酯,硫酯,或其组合。抗腐蚀剂的例子包括,但不限于,碱土金属双烷基酚磺酸盐,二硫代磷酸盐,烯基琥珀酸半酰胺,或其组合。在另一个实施方案中,可将杀虫剂与固体润滑剂纳米颗粒研磨。杀虫剂的例子包括,但不限于,烷基或羟胺苯并***,烷基、烯基琥珀酸的部分烷基酯的胺盐,或其组合。
在另一个实施方案中,湿研磨颗粒的进一步加工可包括将不是作为固体润滑剂纳米颗粒的络合物的一部分的油移除。该方法适合于利用固体润滑剂的干颗粒用途的应用,例如涂料应用。可将油和/或其它液体从湿研磨颗粒中移除以得到基本上干的固体润滑剂颗粒和络合物。该湿研磨并接着干研磨方法可得到固体润滑剂,其具有减少团聚的趋势。在特定的实施方案中,可添加例如丙酮的试剂,其溶解不是络合物部分的油,接着通过干燥方法例如超临界干燥,得到基本上干的固体润滑剂,其包含通过在有机介质中研磨处理的颗粒。
球磨条件可以改变,以及特别地,可以操纵如温度、研磨时间、和球和瓶的尺寸和材料的条件。在各个实施方案中,可在约12小时至约50小时,合适地在约36小时至约50小时,合适地在约40小时至约50小时,和更合适地以约48小时进行球磨。合适地,在室温下进行球磨。增加研磨时间的好处至少包括一种增加有机介质与固体润滑剂纳米颗粒相互作用的时间;和得到更细的尺寸,更好的纳米颗粒产量,更均匀的形状,和更钝化表面。适合于上述研磨的球磨装置的例子包括SPEX CertiPrep 8000D型号,其具有坚硬的不锈钢瓶和坚硬的不锈钢研磨球,但是可以使用任意类型的球磨装置。在一个实施方案中,可使用600-650MPa的压力,14.9牛顿的负荷,和每秒10-3-10-4的应变。
纳米颗粒基润滑剂中的组分比例可对润滑剂的性能有贡献,例如润滑剂的分散稳定性和抗团聚的能力。在湿研磨中,固体润滑剂纳米颗粒对有机介质的合适比例可为约1重量份颗粒比约4重量份有机介质,合适地,约1重量份颗粒比约3重量份有机介质,合适地,约3重量份颗粒比约8重量份有机介质,合适地,约2重量份颗粒比约4重量份有机介质,合适地,约1重量份颗粒比约2重量份有机介质,和合适地,约1重量份颗粒比约1.5重量份有机介质。
在包括固体润滑剂纳米颗粒的润滑剂中,有机介质对乳化剂的合适比例可为约1重量份有机介质比小于或等于约1重量份的乳化剂,合适地,约1重量份有机介质比约0.5重量份乳化剂,或合适地,约0.4至约1重量份的份乳化剂对约1重量分的有机介质。
在基体中超声或分散的固体润滑剂纳米颗粒组合物的量(以重量计)可为约0.25%至约5%,合适地0.5%至约3%,合适地0.5%至约2%,和更合适地0.75%至约2%。
在基体中超声或溶解的乳化剂的量(以重量计),依赖于最终应用、保质期等等,可为约0.5%至约10%,合适地约4%至约8%,合适地约5%至约6%,和合适地约0.75%至约2.25%。
固体润滑剂纳米颗粒组合物可无限制地用作润滑剂、涂料、输送剂、或其组合的。固体润滑剂纳米颗粒组合物可无限制用作分散在基油中的添加剂。也可以无限制地使用组合物润滑边界润滑状态(boundary lubrication regime)。边界润滑状态可以是其中平均油膜厚度可小于组合物表面粗糙度和表面粗糙可在相对运动中彼此接触的润滑状态。在各种应用中,两个表面与润滑剂的相对运动过程中,可出现三种不同的润滑阶段,边界润滑状态在温度、压力和速度上的条件最严格。配合部分可接受高负荷、低速度、极压(例如,1-2GPa)、和高的局部温度(例如,150-300℃)的严格接触条件。边界润滑状态还可以在较低压力和低滑动速度或高温下存在。在边界润滑状态下,配合面可以直接物理接触。该组合物可进一步不受限用作在机械应用、制造应用、矿业应用、航空应用、汽车应用、药物应用、医疗应用、牙齿应用、化妆品应用、食品应用、营养应用、健康相关的应用、生物燃料应用、或其组合应用中的润滑剂或涂料。在最终应用中的用途的特定例子包括,但不限于,机械工具,轴承,齿轮,凸轮轴,泵,传输装置,活塞环,引擎,发电机,针连接(pin-joints),航空***,开矿设备,制造设备,或其组合。用途的进一步的特定例子可以用作,但不限于,润滑剂、油脂、凝胶、化合的塑料部件、浆、粉末、乳液、分散体、或其组合中的添加剂。该组合物也可以用作润滑剂,所述的润滑剂利用固体润滑剂纳米颗粒组合物作为药物应用、医疗应用、牙齿应用、化妆品应用、食品应用、营养应用、健康相关的应用、生物燃料应用、或其组合应用中的输送剂。也可以在杂化无机-有机材料中无限制地使用各种组合物和方法。使用无机-有机材料的应用例子包括,但不限于,光,电,离子,机械,能量,环境,生物,医药,智能薄膜,分离设备,功能智能涂料,光伏和燃料电池,光催化剂,新型催化剂,感应器,智能微电子器件,纳米光子的微光学及光子元件和***,新型化妆品,结合靶向、成像、治疗和活性分子的可控释放的智能治疗载体,和用于汽车或包装工业的纳米陶瓷-聚合物复合材料。
在一些实施方案中,球磨方法可形成密闭笼致密椭圆形结构(类似于足球形状或富勒烯(fullerene)型结构)。当在气体或真空下研磨二硫化钼时,可出现这种情况。图7(A)显示了在空气中球磨48小时的二硫化钼纳米颗粒的密闭笼致密椭圆形结构。
在其它实施方案中,球磨方法可形成开放端口椭圆形结构(类似于椰子形状)的二硫化钼纳米颗粒,其被有机介质和磷脂***和包覆。当在空气或真空中研磨然后在有机介质中研磨二硫化钼时,可出现这种情况。图7(B)显示了在空气中球磨48小时然后在菜子油中球磨48小时的二硫化钼纳米颗粒的开放的端口椭圆形结构。
如在实施例中所示,纳米颗粒基润滑剂的摩擦性能可被改进。摩擦性能可以通过评估不同的性能来测量。抗磨性能为使用工业标准四球摩擦磨损(Four-Ball Wear)(ASTM D4172)试验测得的润滑液性能。四球摩擦磨损试验可评估压力和滑动条件下油提供的保护。将三个固定的钢球放置在试验润滑剂的池子中,使这些钢球与预设试验条件下滚动接触的相同级别的第四个球接触。通过比较三个固定球上的平均磨斑可测得润滑剂磨损保护性能。平均磨斑越小,保护越好。极压性能是使用工业标准四球摩擦磨损(ASTM D2783)试验测得的润滑液性能。该试验方法可适用润滑液的载荷性能的测定。可进行下述两种测定:1)负荷磨损指数(以前的Mean-Hertz负荷)和2)烧结负荷值(kg)。该负荷磨损指数可以是润滑剂的载荷性能。其可以是最小化应用载荷的磨损的润滑剂能力的指数。烧结负荷值可以是滚动球烧结在三个静止球时的最低应用负荷(kg),表示润滑剂所承受的极压水平。烧结点分值和负荷磨损指数越高,润滑剂的抗磨和极压性能越好。摩擦系数(COF)为使用工业标准四球摩擦磨损(ASTM D4172)试验测得的润滑液性能。COF是描述两个物体间的摩擦力比和使其压在一起的力的无因次标量。摩擦系数取决于所用的材料。例如,在金属上的冰具有低的COF,而在公路上的橡胶具有高的COF。减小摩擦的普通方法是使用润滑剂,例如油或水,其被放置在两个表面之间,这样往往显著减小COF。
组合物可具有约0.4mm至约0.5mm的磨斑直径。组合物可具有约0.06至约0.08的COF。组合物可具有约150kg至约350kg的烧结负荷值。组合物可具有约20至约40的负荷磨损指数。这些摩擦性能的值可根据在基体中超声或溶解的固体润滑剂纳米颗粒组合物的量而变化。
具体实施方式
在下面的实施例中阐明了本发明的各种特征和方面,其用于解释说明,而不在于限制本发明。
实施例
实施例1
在SPEX 8000D机器中使用坚硬的不锈钢瓶和球进行球磨。使用MoS2(Alfa Aesar,纯度98%,平均颗粒尺寸700nm)和菜子油(Crisco)作为原料,其比例为1份MoS2(10克)比2份菜子油(20克)。球对粉末的比例为2:1。换言之,容器中的球重量为2重量%,MoS2样品的重量为1重量%。在空气中将MoS2球磨48小时,然后在室温下的菜子油中研磨48小时。球磨后纳米颗粒为约50nm。表1总结了研磨条件和得到的颗粒形态。观察发现研磨介质对球磨的纳米颗粒的形状具有很强的影响。在颗粒尺寸从微米尺寸减小至纳米尺寸时,干研磨显示出平面(plane)的压曲和折叠。然而,此处使用的干研磨条件造成嵌入数个纳米颗粒的微簇。另一方面,湿研磨没有显示出压曲,但是观察到解团聚。
表1:研磨条件和参数对颗粒尺寸和形状的影响
干研磨 | 颗粒形状 | 簇形状 |
12小时 | 具有锐利边的碟形 | 锐利而无规则 |
24小时 | 具有圆边的碟形 | 或多或少的圆形 |
48小时 | 球形 | 球状簇 |
湿研磨 | 颗粒形状 | 簇形状 |
12小时 | 具有锐利边的薄碟 | 具有锐利边的薄碟 |
24小时 | 具有锐利边的薄碟 | 具有锐利边的薄碟 |
48小时 | 具有锐利边的薄碟 | 具有锐利边的薄碟 |
表2:研磨介质对颗粒所得尺寸(亚微米开始尺寸)、形状、和团聚的影响
性能 | 干 | 醇 | 油 | 干研磨和油研磨 |
簇尺寸(nm) | 100 | 300 | 200 | 100 |
颗粒尺寸(nm) | 30 | 80 | 80 | 30 |
团聚 | 高 | 非常少 | 非常少 | 非常少 |
颗粒形状 | 球状 | 小盘状 | 小盘状 | 球状 |
图3显示了如此可获得的(700nm)空气研磨和混合研磨(在空气介质中研磨48小时,然后在油介质中研磨48小时)MoS2纳米颗粒的TEM显微照片。图3(A)表示获得的保持期外(offthe shelf)的MoS2样品的微尺寸颗粒大块。这些显微照片,特别是图3(B),表示在空气介质中研磨时的润滑剂纳米颗粒的团聚。图3(B)清楚地表明空气研磨MoS2的尺寸减小。更高的分辨率(圆圈区域)揭示了在空气介质中研磨后的碟形纳米颗粒。从图3(C)至3(D)可以得出结论,在空气和混合条件下研磨后,颗粒尺寸减小至小于30nm。尽管偶尔观察到簇,但是簇的平均尺寸小于或等于200nm。
混合研磨的样品分散在石蜡油中(来自Walmart),保持悬浮而不下沉。但是,在数周后分散体是不均匀的。为了稳定分散体和增加抗磨性能,添加磷脂。在基油中添加约2重量%的大豆卵磷脂磷脂(来自American Lecithin)。
图4和图5分别显示了在球磨之前和之后的MoS2的XRD和XPS光谱。XRD光谱揭示出无相变以及未观察到研磨后的MoS2中的非晶化。该观察结果与研磨材料的TEM分析中的整个纳米颗粒基体观察到的连续小盘形状一致。在空气和混合介质中球磨的MoS2的XRD光谱中分别观察到峰(FWHM)变宽。该峰变宽可归于颗粒尺寸的减小。估计的颗粒尺寸是6nm。这遵循球磨的主题,其中簇由10nm数量级的颗粒和亚颗粒组成。进行XPS分析来研究由此获得的和混合研磨的MoS2纳米颗粒的表面化学。如图3所示,在由此获得的MoS2样品中的285eV处观察到的碳(C)峰移至286.7eV。286eV和287.8eV的结合能分别对应于C-O和C=O键的形成。观察到的结合能水平可表明含混合的C-O和C=O链的薄层包覆在MoS2颗粒上。
在四球机器上通过ASTM 4172对合成纳米颗粒进行初步的四球摩擦试验。所用的球由AISI 52100不锈钢制造,且被高度抛光。在下述试验条件下使用ASTM D4172进行四球磨斑(Four Ball Wear Scar)试验:
试验温度,℃ | 75(±1.7) |
试验时间,分钟 | 60(±1) |
锭子速度,rpm | 1,200(±60) |
负荷,kg | 40(±0.2) |
在垂直和水平方向测量每个静止球的磨斑直径(WSD,mm)。报道了3个独立试验的WSD的平均值,其精确度在±0.03mm之内。
在下述试验条件下利用ASTM D2783进行四球极压(Four BallExtreme Pressure)试验:
试验温度,℃ | 23 |
试验时间,分钟 | 60(±1) |
锭子速度,rpm | 1,770(±60) |
负荷,kg | 变化,10秒/阶段 |
球材料 | AISI-E52100 |
硬度 | 64-66 |
级别 | 25EP |
作为石蜡油中的添加剂,评估了三种不同颗粒(w/w比)的抗磨性能。图6(A)显示了不含纳米颗粒添加剂的石蜡油、具有微尺寸MoS2的石蜡油、具有在空气中研磨48小时的MoS2的石蜡油、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油的平均磨斑测量。图6(B)显示了不含纳米颗粒添加剂的石蜡油、具有微尺寸MoS2的石蜡油、具有在空气中研磨48小时的MoS2的石蜡油、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油的负荷磨损指数。图6(C)显示了不含纳米颗粒添加剂的石蜡油、具有微尺寸MoS2的石蜡油、具有在空气中研磨48小时的MoS2的石蜡油、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油的COF。图6(D)显示了具有微尺寸MoS2的石蜡油、具有在空气中研磨48小时的MoS2的石蜡油、和具有在空气中研磨48小时然后在菜子油中研磨48小时的MoS2的石蜡油的极压数据。在每次试验中,纳米颗粒添加剂的量为1重量%。
基油中纳米颗粒组合物添加剂的试验数据
使用能力分散x-射线分析(EDS)研究的磨斑中的转移膜识别除钼和硫之外的磷酸盐信号。图9(a)描述了不含纳米颗粒添加剂的石蜡油的基本情况。图9(b)描述了含有二硫化钼纳米颗粒和乳化剂的石蜡油。其显示了磨痕中钼(Mo)-硫(S)-磷(P)的早期迹象。在图9(a)和图9(b)中发现铁(Fe),因为其是四球摩擦试验中球的材料(52100钢)。因为具有相同的结合能,钼和硫的峰一致,无法分辨。元素分布图也显示了相似的结果。
预言的实施例:
使用与实施例1相似的方法进行实施例2-23,除非另有说明。
实施例2
来自ADM的MoS2(Alfa Aesar,纯度98%,700nm平均颗粒尺寸)和菜子油用作原料。在不同的时间条件,变化的球/粉末比,和在不同的环境条件,开始时用空气,菜子油和接下来的在空气然后在菜子油中组合的研磨条件下球磨MoS2粉末。也在不同类型的有机介质中球磨。例如,使用的一种有机介质是菜子油甲酯。该过程类似于上述的实施例。
可以使用不同类型的球磨方法。例如,第一步,在空气中使用低温球磨,然后在有机介质中使用高温球磨。
球磨后,使用与基油(例如石蜡油)混合的磷脂处理活性EP-EA(极压-环境可接受的)颗粒。
实施例3
使用硼球磨二硫化钼,使用1份二硫化钼对1份硼的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-硼-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例4
使用铜球磨二硫化钼,使用1份二硫化钼对1份金属的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-铜-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例5
球磨1:1比例的二硫化钼/石墨(来自AlfaAesar)混合物。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-石墨-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例6
球磨1:1比例的二硫化钼/氮化硼(AlfaAesar)混合物。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-氮化硼-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例7
球磨1:1:1比例的二硫化钼/石墨/氮化硼混合物。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-石墨-氮化硼-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例8
球磨1:1:1比例的二硫化钼/石墨混合物。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-石墨-硼-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例9
使用铜球磨1:1比例的二硫化钼/石墨混合物,使用1份二硫化钼/石墨对1份金属的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-石墨-铜-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例10
使用硼球磨1:1比例的二硫化钼/氮化硼混合物,使用1份二硫化钼/氮化硼对1份金属的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-氮化硼-硼-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例11
使用铜球磨1:1比例的二硫化钼/氮化硼混合物,使用1份二硫化钼/氮化硼对1份金属的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-氮化硼-铜-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例12
使用硼球磨1:1:1比例的二硫化钼/氮化硼/石墨混合物,使用1份二硫化钼/氮化硼/石墨对1份金属的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-氮化硼-石墨-硼-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例13
使用铜球磨1:1:1比例的二硫化钼/氮化硼/石墨混合物,使用1份二硫化钼/氮化硼/石墨对1份金属的比例。然后使用植物油(菜子油)球磨该混合物,使用1份固体润滑剂纳米颗粒对1.5份菜子油的比例。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-氮化硼-石墨-铜-菜子油)对2份乳化剂的比例。将其添加至基油(石蜡油)。
实施例14
实施例15
实施例16
以1份二硫化钼对1份金属添加剂的比例,使用金属添加剂(如铜,银,铅等)球磨二硫化钼。在植物油基酯(菜子油甲酯)中以1份固体润滑剂纳米颗粒对1.5份酯的比例进一步球磨该混合物。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-酯)对2份磷脂乳化剂的比例。将其添加至基油(石蜡油)。
实施例17
以1份二硫化钼对1份金属添加剂的比例,使用金属添加剂(如铜,银,铅等)球磨二硫化钼。在植物油基酯(菜子油甲酯)中以1份固体润滑剂纳米颗粒对1.5份酯的比例进一步球磨该混合物。将其添加至基油(石蜡油)。
实施例18
球磨二硫化钼。在植物油基酯(菜子油甲酯)中以1份固体润滑剂纳米颗粒对1.5份酯的比例进一步球磨该固体润滑剂纳米颗粒。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-酯)对2份磷脂乳化剂的比例。将其添加至基油(石蜡油)。
实施例19
球磨二硫化钼。在植物油基酯(菜子油甲酯)中以1份固体润滑剂纳米颗粒对1.5份酯的比例进一步球磨该固体润滑剂纳米颗粒。将其添加至基油(石蜡油)。
实施例20
以1份二硫化钼对1份金属添加剂的比例,使用金属添加剂(如铜,银,铅等)球磨二硫化钼。在脂肪酸(油酸)中以1份固体润滑剂纳米颗粒对1.5份脂肪酸的比例进一步球磨该混合物。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-油酸)对2份磷脂乳化剂的比例。将其添加至基油(石蜡油)。
实施例21
以1份二硫化钼对1份金属添加剂的比例,使用金属添加剂(如铜,银,铅等)球磨二硫化钼。在脂肪酸(油酸)中以1份固体润滑剂纳米颗粒对1.5份脂肪酸的比例进一步球磨该混合物。将其添加至基油(石蜡油)。
实施例22
球磨二硫化钼。在脂肪酸(油酸)中以1份固体润滑剂纳米颗粒对1.5份脂肪酸的比例进一步球磨该固体润滑剂纳米颗粒。添加乳化剂,使用1份固体润滑剂纳米颗粒组合物(MoS2-油酸)对2份磷脂乳化剂的比例。将其添加至基油(石蜡油)。
实施例23
球磨二硫化钼。在脂肪酸(油酸)中以1份固体润滑剂纳米颗粒对1.5份脂肪酸的比例进一步球磨该固体润滑剂纳米颗粒。将其添加至基油(石蜡油)。
Claims (70)
1、一种组合物,其包括:
固体润滑剂纳米颗粒;和
有机介质。
2、根据权利要求1所述的组合物,其中固体润滑剂纳米颗粒包括球磨的纳米颗粒、化学机械研磨的纳米颗粒、或其组合。
3、根据权利要求1所述的组合物,其中组合物是纳米颗粒基润滑剂。
4、根据权利要求1所述的组合物,其中有机介质包括油介质、油脂介质、醇介质、或其组合。
5、根据权利要求1所述的组合物,其中有机介质包括复合油、菜子油、植物油、大豆油、玉米油、菜子油的乙酯和甲酯、蒸馏的单甘酯、单甘酯、甘油二酯、单甘酯的乙酸酯、单甘酯的有机酸酯、脱水山梨糖醇、脂肪酸的脱水山梨糖酯、脂肪酸的丙二醇酯、脂肪酸的聚甘油酯、烃油、正十六烷、磷脂、或其组合。
6、根据权利要求1所述的组合物,其中有机介质包括复合油。
7、根据权利要求1所述的组合物,其中纳米颗粒包括二硫化钼、二硫化钨、石墨、聚四氟乙烯、氟化铈、氧化锌、氮化硼、六方氮化硼、硫酸银、碘化镉、碘化铅、氟化钡、硫化锡、磷酸锌、银、铅、镍、硫化锌、云母、硝酸硼、硼砂、氟化碳、嵌入石墨、磷化锌、铜、硼、或其组合。
8、根据权利要求1所述的组合物,其进一步包括微尺寸颗粒。
9、根据权利要求1所述的组合物,其进一步包括乳化剂。
10、根据权利要求9所述的组合物,其中乳化剂具有约2至约7的亲水-亲油平衡。
11、根据权利要求9所述的组合物,其中乳化剂包括卵磷脂、磷脂卵磷脂、大豆卵磷脂、洗涤剂、蒸馏的单甘酯、单甘酯、甘油二酯、单甘酯的乙酸酯、单甘酯的有机酸酯、脂肪酸的脱水山梨糖酯、脂肪酸的丙二醇酯、脂肪酸的聚甘油酯、或其组合。
12、根据权利要求1所述的组合物,其进一步包括基体。
13、根据权利要求12所述的组合物,其中基体包括油、油脂、喷雾、塑料、凝胶、或其组合。
14、根据权利要求12所述的组合物,其中基体包括烃油、植物油、玉米油、花生油、菜子油、大豆油、矿物油、石蜡油、合成油、石油凝胶、石油油脂、烃凝胶、烃油脂、锂基油脂、氟醚基油脂、乙烯基双硬脂酰胺、蜡、硅氧烷、或其组合。
15、根据权利要求1所述的组合物,其具有约1重量份有机介质比小于或等于约1重量份的乳化剂。
16、根据权利要求1所述的组合物,其具有约1重量份有机介质比小于或等于约0.4重量份的乳化剂。
17、根据权利要求1所述的组合物,其具有约1份固体润滑剂纳米颗粒比约3份的有机介质。
18、根据权利要求1所述的组合物,其具有约1份固体润滑剂纳米颗粒比约4份的有机介质。
19、根据权利要求1所述的组合物,其具有约3份固体润滑剂纳米颗粒比约8份的有机介质。
20、根据权利要求1所述的组合物,其具有约2份固体润滑剂纳米颗粒比约4份的有机介质。
21、根据权利要求1所述的组合物,其具有约1份固体润滑剂纳米颗粒比约2份的有机介质。
22、根据权利要求1所述的组合物,其中固体润滑剂纳米颗粒包括密闭结构。
23、根据权利要求1所述的组合物,其中固体润滑剂纳米颗粒包括开放结构。
24、一种润滑或涂覆为最终应用的一部分的物体的方法,该方法包括用权利要求1所述组合物润滑或涂覆物体。
25、根据权利要求24所述的方法,其中物体包括边界润滑状态。
26、根据权利要求24所述的方法,其中在包括机械应用、制造应用、矿业应用、航空应用、和汽车应用的应用中使用该方法。
27、根据权利要求24所述的方法,其中在包括药物应用、医疗应用、牙齿应用、化妆品应用、食品应用、营养应用、健康相关的应用、生物燃料应用、或其组合应用中使用该方法。
28、根据权利要求24所述的方法,其中物体包括机械工具、轴承、齿轮、凸轮轴、泵、传输装置、活塞环、引擎、发电机、针连接、航空***、开矿设备、制造设备、无机-有机材料、或其组合。
29、根据权利要求24所述的方法,其中组合物被添加至润滑剂、油脂、喷雾、凝胶、化合的塑料部件、浆、粉末、乳液、分散体、或其组合中。
30、根据权利要求24所述的方法,其中润滑物体包括使用包含固体润滑剂纳米颗粒和作为输送剂的有机介质的组合物。
31、根据权利要求30所述的方法,其中在包括药物应用、医疗应用、牙齿应用、化妆品应用、食品应用、营养应用、健康相关的应用、生物燃料应用、或其组合应用中使用该方法。
32、根据权利要求30所述的方法,其中在包括无机-有机材料应用中使用该方法。
33、根据权利要求32所述的方法,其中无机-有机材料应用包括光,电,离子,机械,能量,环境,生物,医药,智能薄膜,分离设备,功能智能涂料,光伏和燃料电池,光催化剂,新型催化剂,感应器,智能微电子器件,纳米光子的微光学及光子元件和***,新型化妆品,结合靶向、成像、治疗和活性分子的可控释放的智能治疗载体,和用于汽车或包装工业的纳米陶瓷-聚合物复合材料。
34、一种纳米颗粒,其包括层状材料。
35、根据权利要求34所述的组合物,其中层状材料包括硫属化合物。
36、根据权利要求34所述的组合物,其中层状材料包括二硫化钼、二硫化钨、石墨、嵌入石墨、或其组合。
37、根据权利要求34所述的组合物,其进一步包括聚四氟乙烯、氮化硼、六方氮化硼、或其组合。
38、根据权利要求37所述的组合物,其进一步包括软金属、银、铅、镍、铜、氟化铈、氧化锌、硫酸银、碘化镉、碘化铅、氟化钡、硫化锡、磷酸锌、硫化锌、云母、硝酸硼、硼砂、氟化碳、磷化锌、硼、或其组合。
39、一种制造纳米颗粒的方法,所述纳米颗粒包括研磨层状材料。
40、根据权利要求39所述的方法,其中研磨包括球磨、化学机械研磨、或其组合。
41、根据权利要求39所述的方法,其中颗粒被研磨至小于或等于约500纳米的平均尺寸。
42、根据权利要求39所述的方法,其中颗粒被研磨至小于或等于约100纳米的平均尺寸。
43、根据权利要求39所述的方法,其中层状材料包括硫属化合物。
44、根据权利要求39所述的方法,其中层状材料包括二硫化钼、二硫化钨、石墨、嵌入石墨、或其组合。
45、根据权利要求39所述的方法,其进一步包括结合聚四氟乙烯、氮化硼、六方氮化硼、或其组合研磨层状材料。
46、根据权利要求45所述的方法,其进一步包括结合软金属、银、铅、镍、铜、氟化铈、氧化锌、硫酸银、碘化镉、碘化铅、氟化钡、硫化锡、磷酸锌、硫化锌、云母、硝酸硼、硼砂、氟化碳、磷化锌、硼、或其组合研磨层状材料。
47、根据权利要求40所述的方法,其中球磨包括高能球磨、中能球磨、或其组合。
48、根据权利要求40所述的方法,其中球磨包括在真空、气体、液体、在第二固体存在下、或其组合下研磨层状材料。
49、根据权利要求48所述的方法,其中球磨包括在空气、醇、油、或其组合中研磨层状材料。
50、根据权利要求40所述的方法,其中球磨包括第一球磨和至少一个以上的后续球磨。
51、根据权利要求50所述的方法,其中第一球磨包括干研磨和至少一个以上包括湿研磨的后续球磨。
52、根据权利要求51所述的方法,其中在空气中球磨,然后在有机介质中研磨。
53、根据权利要求52所述的方法,其中有机介质包括醇、油、或其组合。
54、根据权利要求52所述的方法,其中有机介质包括复合油、菜子油、植物油、大豆油、玉米油、菜子油的乙酯和甲酯、蒸馏的单甘酯、单甘酯、甘油二酯、单甘酯的乙酸酯、单甘酯的有机酸酯、脱水山梨糖醇、脂肪酸的脱水山梨糖酯、脂肪酸的丙二醇酯、脂肪酸的聚甘油酯、烃油、正十六烷、或其组合。
55、根据权利要求52所述的方法,其中有机介质包括复合油。
56、根据权利要求40所述的方法,其中在约12小时至约50小时之间进行球磨。
57、根据权利要求39所述的方法,其中研磨包括研磨含有抗氧化剂的层状材料。
58、根据权利要求39所述的方法,其中研磨包括研磨含有抗腐蚀剂的层状材料。
59、根据权利要求57所述的方法,其中抗氧化剂包括受阻酚、烷基化酚、烷基胺、芳基胺、2,6-二-叔丁基-4-甲基酚、4,4’-二-叔辛基二苯胺、叔丁基对苯二酚、三(2,4-二-叔丁基苯基)磷酸酯、亚磷酸酯、硫酯、或其组合。
60、根据权利要求58所述的方法,其中抗腐蚀剂包括碱土金属双烷基酚磺酸盐、二硫代磷酸盐、烯基琥珀酸半酰胺、或其组合。
61、一种制备润滑剂的方法,该方法包括研磨层状材料以形成纳米颗粒;和将纳米颗粒掺入基体以形成润滑剂。
62、根据权利要求61所述的方法,其进一步包括结合聚四氟乙烯、氮化硼、六方氮化硼、或其组合的研磨层状材料。
63、根据权利要求62所述的方法,其进一步包括结合软金属、银、铅、镍、铜、氟化铈、氧化锌、硫酸银、碘化镉、碘化铅、氟化钡、硫化锡、磷酸锌、硫化锌、云母、硝酸硼、硼砂、氟化碳、磷化锌、硼、或其组合的研磨层状材料。
64、根据权利要求61所述的方法,其中乳化剂与基体混合。
65、根据权利要求64所述的方法,其中乳化剂在添加纳米颗粒前与基体混合。
66、根据权利要求64所述的方法,其中混合包括超声。
67、根据权利要求61所述的方法,其中在基体中超声或分散约0.5重量%至约2重量%的纳米颗粒。
68、根据权利要求61所述的方法,其中在基体中超声或分散约0.25重量%至约5重量%的纳米颗粒。
69、根据权利要求64所述的方法,其中在基体中超声或溶解约0.75重量%至约2.25重量%的乳化剂。
70、根据权利要求64所述的方法,其中在基体中超声或溶解约0.5%至约10%的乳化剂。
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US20140364348A1 (en) | 2014-12-11 |
CA2636932A1 (en) | 2007-07-19 |
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JP5603013B2 (ja) | 2014-10-08 |
US20080312111A1 (en) | 2008-12-18 |
US8492319B2 (en) | 2013-07-23 |
US20140212587A1 (en) | 2014-07-31 |
MX2008009032A (es) | 2008-09-26 |
EP1973998A2 (en) | 2008-10-01 |
US9650589B2 (en) | 2017-05-16 |
JP6023745B2 (ja) | 2016-11-09 |
CA2636932C (en) | 2014-03-25 |
WO2007082299A2 (en) | 2007-07-19 |
JP2016153505A (ja) | 2016-08-25 |
JP2009523863A (ja) | 2009-06-25 |
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