CN110382568A - 烯丙基封端的聚异丁烯的硼氢化/氧化 - Google Patents
烯丙基封端的聚异丁烯的硼氢化/氧化 Download PDFInfo
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Abstract
一种由二烯丙基聚异丁烯制备聚异丁烯二醇的方法。所述方法包括:将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,和将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
Description
相关申请的交叉引用
本申请要求于2017年3月7日提交的临时申请No.62/468,316的优先权,其通过引用整体并入本文。
技术领域
本发明涉及制备聚异丁烯二醇的方法。更具体地,本发明涉及由二烯丙基聚异丁烯制备聚异丁烯二醇的方法。
背景技术
基于双官能遥爪软段的热塑性弹性体具有格外理想的特性。可用于这种热塑性弹性体中的双官能遥爪软段的实例包括基于聚异丁烯的软段。存在仅由聚异丁烯和聚异丁烯基材料提供的许多独特且理想的物理和机械特性,包括热稳定性、生物相容性和不透气性,等等。这些特性可以在共聚策略中用其它材料调节以及进一步改性,例如合成基于聚异丁烯(PIB)软段的聚氨酯。通过碳正离子聚合制备基于聚异丁烯的软段的方法采用双官能引发剂分子开始并产生聚异丁烯二醇。
用于所述制备聚异丁烯二醇的方法中的材料中的一些昂贵、有害且难以处理。需要更安全且更低成本的材料。
发明内容
实施例1是一种由二烯丙基聚异丁烯制备聚异丁烯二醇的方法。所述方法包括:将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,和将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例2是如实施例1所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例3是如实施例1或2所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例4是如实施例1或2所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
实施例5是如实施例1-4中任一项所述的方法,其中所述硼烷配位溶剂包括四氢呋喃、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例6是如实施例1-5中任一项所述的方法,其中所述将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇包括将碱和氧化剂与聚异丁烯二烷基硼烷结合。
实施例7是如实施例6所述的方法,其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例8是如实施例6或7所述的方法,其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例9是一种制备聚异丁烯二醇的方法,所述方法包括:提供聚异丁烯二氯化物,使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯,将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,和将碱和氧化剂与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例10是如实施例9所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例11是如实施例9或10所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例12是如实施例9或10所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
实施例13是如实施例9-12中任一项所述的方法,其中所述硼烷配位溶剂包括四氢呋喃、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例14是如实施例9-13中任一项所述的方法,其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例15是如实施例9-14中任一项所述的方法,其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例16是一种制备聚异丁烯二醇的方法,所述方法包括:提供二烯丙基聚异丁烯,将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,和将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例17是如实施例16所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例18是如实施例16或17所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例19是如实施例16或17所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
实施例20是如实施例16-19中任一项所述的方法,其中所述硼烷配位溶剂包括四氢呋喃、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例21是如实施例16-20中任一项所述的方法,其中所述提供二烯丙基聚异丁烯包括:提供聚异丁烯二氯化物,和使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯。
实施例22是如实施例16所述的方法,其中所述将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇包括将碱和氧化剂与聚异丁烯二烷基硼烷结合。
实施例23是如实施例22所述的方法,其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例24是如实施例22或23所述的方法,其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例25是一种制备聚异丁烯二醇的方法,所述方法包括:提供聚异丁烯二氯化物,使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯,将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,和将碱和氧化剂与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例26是如实施例25所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例27是如实施例25或26所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例28是如实施例25或26所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
实施例29是如实施例25-28中任一项所述的方法,其中所述硼烷配位溶剂包括四氢呋喃、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例30是如实施例25-29中任一项所述的方法,其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例31是如实施例25-30中任一项所述的方法,其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例32是一种制备聚异丁烯二醇的方法,所述方法包括:提供聚异丁烯二氯化物,使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯,将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,和将过氧化氢以及氢氧化钠和氢氧化钾中的至少一种与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与四氢呋喃、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例33是如实施例32所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例34是如实施例32所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
实施例35是如实施例32-34中任一项所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
尽管公开了多个实施方案,但是通过以下详细描述,本发明的其他实施方案对于本领域技术人员将变得明显,以下详细描述示出并描述了本发明的说明性实施方案。因此,附图和详细描述应被认为是说明性的而非限制性的。
附图说明
图1示出了根据本公开内容的实施方案的聚异丁烯二氯化物的形成。
图2示出了根据本公开内容的实施方案的由图1的聚异丁烯二氯化物形成二烯丙基聚异丁烯。
图3示出了根据本公开内容的实施方案的由图2的二烯丙基聚异丁烯形成聚异丁烯二烷基硼烷。
图4示出了根据本公开内容的实施方案的由图3的聚异丁烯二烷基硼烷形成聚异丁烯二醇。
尽管本发明可以进行各种修改和替换形式,但是在附图中通过实例的方式示出了具体实施方案,并且在下面详细描述。然而,其目的不是将本发明限制于所描述的具体实施方案。相反,本发明旨在覆盖落入由所附权利要求限定的本发明的范围内的所有修改方案、等同方案和替代方案。
具体实施方式
在本公开内容的实施方案中,制备聚异丁烯二醇可能需要将二烯丙基聚异丁烯硼氢化然后进行氧化步骤。本领域中通常用于提供用于硼氢化的硼烷的试剂是9-硼双环(3.3.1)壬烷(9-BBN)。然而,9-BBN是难以处理和储存的昂贵材料。另外,9-BBN是可燃的。
本公开内容的实施方案可以使用在硼烷配位溶剂中与酸结合的硼氢化物的碱金属盐以提供用于硼氢化的硼烷源。在本公开内容的实施方案中,将硼氢化物的碱金属盐和酸与二烯丙基聚异丁烯原位结合并彼此独立地添加至二烯丙基聚异丁烯。即,硼氢化物的碱金属盐和酸在添加至二烯丙基聚异丁烯之前不相互结合。以此方式,硼烷仅在含有二烯丙基聚异丁烯的反应容器中形成,这使得硼烷在其与二烯丙基聚异丁烯反应之前向水分的暴露最小化。这是有益的,因为硼烷易于与水分反应形成硼酸,最终必须以额外的成本将硼酸从聚异丁烯二醇中除去。此外,任何与水分反应的硼烷都不能用于硼氢化,因此需要额外的材料来生成硼烷并与二烯丙基聚异丁烯反应,这增加了硼氢化的成本。
与9-BBN相反,一些硼氢化物的碱金属盐,如硼氢化钠,是不可燃的并且更容易储存。硼氢化钠用于硼氢化可以导致比使用9-BBN节省约95%的成本。
图1-4示出了根据本公开内容的实施方案的聚异丁烯二醇的生产。如图1所示,异丁烯可以与双官能阳离子引发剂化合物如受阻二枯基醚和甲基氯化物在四氯化钛的存在下反应,以使异丁烯聚合并产生聚异丁烯二氯化物。应理解,这仅是生产聚异丁烯二氯化物的一种方法,并且可以使用其它方法。
一旦产生聚异丁烯二氯化物,烯丙基端基可被加到聚异丁烯链上。在图2所示的实施方案中,将烯丙基三甲基硅烷添加至聚异丁烯二氯化物。然后,聚异丁烯二氯化物可以与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯,如图2所示。二烯丙基聚异丁烯的烯丙基端基导致近定量取代,引起高度遥爪聚合物的产生。高度遥爪聚合物允许具有有益特性的较高分子量聚合物链。
一旦产生二烯丙基聚异丁烯,就将硼氢化物的碱金属盐和硼烷配位溶剂原位添加至二烯丙基聚异丁烯。在一些实施方案中,在添加硼烷配位溶剂之后添加硼氢化物的碱金属盐。在其它实施方案中,在添加硼氢化物的碱金属盐之后添加硼烷配位溶剂。在添加硼氢化物的碱金属盐和硼烷配位溶剂之后,将酸原位添加至二烯丙基聚异丁烯。如上所述,硼氢化物的碱金属盐和酸在添加至二烯丙基聚异丁烯之前不进行结合。
在一些实施方案中,所述硼氢化物的碱金属盐可包括硼氢化钠、硼氢化钾和/或硼氢化锂。在一些实施方案中,所述酸可包括强无机酸,如硫酸、氢氯酸、氢碘酸、氢溴酸或其混合物。在一些实施方案中,所述酸可包括元素卤化物,如碘、溴或其混合物。在一些实施方案中,所述酸可包括强路易斯酸,如三氯化硼、三氯化铝、三氟化铝或其混合物。在一些实施方案中,所述硼烷配位溶剂可包括四氢呋喃(THF)、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚、四甘醇二甲醚或其混合物。
在一些实施方案中,硼烷配位溶剂与硼氢化物的碱金属盐的摩尔比为至少1:1,以使硼烷配位并稳定,从而防止副反应。在一些实施方案中,硼烷配位溶剂与硼氢化物的碱金属盐的摩尔比低至1.1:1、1.2:1、1.3:1、1.4:1或1.5:1,或高至1.6:1、1.7:1、1.8:1、1.9:1或2:1,或在限定于任何两个前述值之间的任何值之间,例如1.1:1至2:1、1.2:1至1.9:1、1.3:1至1.8:1、1.4:1至1.7:1或1.5:1至1.6:1。
在硼烷配位溶剂的存在下将硼氢化物的碱金属盐和酸结合可以产生硼烷络合物。例如,在一些实施方案中,将硼氢化钠(NaBH4)和无机酸如硫酸(H2SO4)与THF原位结合以产生硼烷络合物,如下面反应式1所示:
反应式1 2NaBH4+H2SO4+2THF→2BH3:THF+Na2SO4+H2
产生的氢气(H2)可以用惰性气体如氮气稀释并安全地排出。硫酸钠(Na2SO4)可通过随后的水洗除去。
在一些其它实施方案中,将硼氢化钠和路易斯酸如三氯化硼(BCl3)与THF原位结合以产生硼烷络合物,如下面反应式2所示:
反应式2 3NaBH4+BCl3+4THF→4BH3:THF+3NaCl
如图3所示,硼烷络合物可以与二烯丙基聚异丁烯原位反应以产生聚异丁烯二烷基硼烷。已经发现硼烷络合物的反应性足以将二烯丙基聚异丁烯的烯丙基端基硼氢化。这是令人惊讶的,因为烯丙基端基R-CH2-CH=CH2比其它亚乙烯基端基(如R–C(CH3)=CH2或R–CH=CH2,其中R是聚异丁烯链)的活性低。
然后可以将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。在一些实施方案中,可以通过加入氧化剂例如过氧化氢、过乙酸、高锰酸钾或过氧化苯甲酰来氧化聚异丁烯二烷基硼烷。图4示出了由聚异丁烯二烷基硼烷通过用过氧化氢氧化形成聚异丁烯二醇。在一些实施方案中,所述氧化在通过添加碱(例如氢氧化钠或氢氧化钾)所产生的碱性环境中进行。
在不脱离本发明的范围的情况下,可以对所讨论的示例性实施方案进行各种修改和添加。例如,尽管上述实施方案涉及特定特征,但本发明的范围还包括具有不同特征组合的实施方案和不包括所有所述特征的实施方案。因此,本发明的范围旨在包含落入权利要求范围内的所有这种替代方案、修改方案和变化方案,以及其所有等同方案。
实施例
聚异丁烯(PIB)二醇的合成
将受阻二枯基醚与无水己烷和2,6-二叔丁基吡啶在反应器中结合。通过冷却至-80℃的冷却盘管将甲基氯化物(MeCl)和异丁烯添加至反应器。将溶液搅拌并通过反应器中的液氮冷却套或盘管保持在-80℃。通过向反应器添加四氯化钛引发聚合,以形成聚异丁烯二氯化物(图1)。30分钟后,向反应器添加烯丙基三甲基硅烷,以在封端反应中向聚合物链末端引入烯丙基(图2)。2小时后,通过在-80℃下添加甲醇(MeOH)来终止反应。将所得溶液在25℃下搅拌过夜,直到MeCl完全蒸发。用氯化钠水溶液洗涤所得聚合物。排出反应器中来自底层的含水废物,然后进行多次去离子水洗涤,直到水层的pH为中性。最终洗涤后,向反应器添加大量的MeOH以使聚合物沉淀。将所得聚合物转移至蒸馏烧瓶,与甲苯混合,并通过干甲苯的共沸蒸馏进行干燥,以制备二烯丙基聚异丁烯(遥爪烯丙基封端的聚异丁烯)。
在装有磁力搅拌器、干燥氮气层、冰浴、橡胶隔片和数字热电偶的2000mL三颈圆底烧瓶中,将10.66g二烯丙基聚异丁烯(0.005摩尔,分子量为2000Da)溶解在605mL无水THF中。将0.605g(0.016摩尔)硼氢化钠添加至烧瓶中的二烯丙基聚异丁烯,并借助于搅拌使其溶解。在所得溶液在0℃平衡后,使用注射器将0.8523g(0.016摩尔)浓硫酸的等分试样逐滴添加至烧瓶中的溶液,导致氢气的逸出和聚异丁烯二烷基硼烷的形成(图3)。将溶液升至室温,然后用16mL 3N NaOH水溶液(0.016摩尔)猝灭。然后用1.81mL 30%H2O2(0.016摩尔)处理包括聚异丁烯二烷基硼烷的猝灭溶液,并使其反应12小时以形成聚异丁烯二醇(图4)。然后用500mL己烷和50mL包括3.326g亚硫酸氢钠(0.031摩尔)的溶液萃取所述溶液以猝灭任何未反应的过氧化物。将混合物转移至分液漏斗,并除去水层。将己烷溶液用去离子水洗涤三次。然后采用旋转蒸发将有机溶液提出,产生透明粘性油。
透明粘性油的质子核磁共振光谱证实了1-羟丙基封端的端基的存在,从而证实了聚异丁烯二醇的合成。
Claims (15)
1.一种由二烯丙基聚异丁烯制备聚异丁烯二醇的方法,所述方法包含:
通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合而将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,其中在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合;和
将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。
2.根据权利要求1所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
3.如权利要求1或2中任一项所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
4.如权利要求1或2中任一项所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
5.如权利要求1-4中任一项所述的方法,其中所述硼烷配位溶剂包括四氢呋喃、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
6.如权利要求1-5中任一项所述的方法,其中所述将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇包括将碱和氧化剂与聚异丁烯二烷基硼烷结合。
7.根据权利要求6所述的方法,其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
8.如权利要求6或7中任一项所述的方法,其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
9.一种制备聚异丁烯二醇的方法,所述方法包含:
提供聚异丁烯二氯化物;
使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯;
通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合而将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷,其中在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合;和
将碱和氧化剂与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。
10.根据权利要求9所述的方法,其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
11.如权利要求9或10中任一项所述的方法,其中所述酸是强无机酸,所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
12.如权利要求9或10中任一项所述的方法,其中所述酸包括强路易斯酸、卤化物或其组合;所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种;并且所述卤化物包括碘和溴中的至少一种。
13.如权利要求9-12中任一项所述的方法,其中所述硼烷配位溶剂包括四氢呋喃、二***、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
14.如权利要求9-13中任一项所述的方法,其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
15.如权利要求9-14中任一项所述的方法,其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
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CN110382568B (zh) | 2022-03-04 |
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US20180258196A1 (en) | 2018-09-13 |
US10526429B2 (en) | 2020-01-07 |
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