CN110139708B - 用于提取锂、汞和钪的分子印迹聚合物珠粒 - Google Patents
用于提取锂、汞和钪的分子印迹聚合物珠粒 Download PDFInfo
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- CN110139708B CN110139708B CN201780071722.8A CN201780071722A CN110139708B CN 110139708 B CN110139708 B CN 110139708B CN 201780071722 A CN201780071722 A CN 201780071722A CN 110139708 B CN110139708 B CN 110139708B
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Images
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Abstract
本公开提供了用于从化学混合物中选择性地隔绝一种或更多种靶标分子的分子印迹聚合物(MIP)技术。本文也公开了MIP珠粒以及制备和使用它们的方法。
Description
相关申请的交叉引用
本申请要求2016年11月3日提交的美国临时申请号62/417,164的优先权,其内容已通过引用整体并入本文。
背景技术
提取和回收工艺例如在水纯化、采矿和废物处理中是常见的。尽管这些工艺的具体单元操作和工艺化学可能不同,但基本途径是相同的-精细机械、浮法浓缩、化学分离、化学沉淀、加热和其他化学工艺,这些工艺通常是冗长、能量密集且昂贵的。替代工艺可以利用吸收剂来除去靶标或预浓缩靶标用于提取。用于除去或隔绝溶解物质的活性炭或离子交换吸收剂、膜、反渗透、液/液提取方法是常见的。
已开发对“靶标”分子具有大幅度改进的特异性的分子印迹聚合物(“MIP”),所述“靶标”分子将需要从工艺流(例如在废物处理应用中)除去或由于它的价值而需要从工艺流隔绝(例如隔离)出来。MIP是被设计为对特定靶标分子具有高选择性的聚合物。MIP是通过使与靶标分子配位或“结合”的可聚合配体聚合来制备。将靶标分子和可聚合配体掺合成预聚合混合物,使其形成络合物,然后进行聚合(通常在一种或更多种非配体单体和交叉联接单体存在下)。因此,靶标分子充当用于界定聚合基体内对靶标分子具有特异性(例如具有对应于靶标分子的形状或尺寸)的空腔或吸收位点的“模板”。然后,在将MIP用作吸收剂之前,从MIP上除去靶标分子。
然而,尽管对期望靶标分子具有高选择性,但MIP具有显著缺点。例如,如果靶标分子具有高度的价值(例如贵金属)或危险性(例如有毒或有放射性),那么相较于选择性较小但便宜很多的吸收剂,在制备MIP时需要使用靶标分子自身作为模板,可由于例如靶标分子的成本或为处理靶标分子所需的预防措施而极其昂贵。此外,因为在聚合物合成期间靶标分子必须保持与可聚合配体络合,所以如果靶标分子/可聚合配体络合物不稳定或以其他方式与聚合条件(例如催化剂、其他单体、低溶解性等)不相容,那么可能根本不可能制备MIP,或需要复杂或困难的反应条件。因此,期望制备具备有利的选择性和常规MIP材料的其他特征,但不具有使用靶标分子作为模板制备MIP时所固有的劣势的吸收剂。本公开的方法和材料提供对常规MIP材料和工艺的此类改进。
发明内容
本公开一般地涉及分子印迹聚合物。更特别地,本公开涉及用于结合复杂混合物中有时存在的靶标分子的离子型分子印迹聚合物珠粒,其在各个实施方案中利用包括二价阴离子和三价阴离子在内的无机或有机阴离子,作为具有类似电荷和分子结构的阴离子靶标金属络合物的替代物。在某些实施方案中,本公开涉及用于选择性地结合混合物中存在的阴离子靶标金属络合物的阳离子靶标金属组分的阴离子分子印迹聚合物珠粒。在此类MIP珠粒中,设计或选择MIP结合空腔中的阴离子配体(一种或多种),使其与阴离子靶标金属络合物的阴离子配体相比,对该络合物的靶标金属阳离子具有更高的亲和力。在另一些其他实施方案中,本公开涉及高表面积的MIP珠粒。因此,本公开涉及化学、聚合物和材料科学领域。
本公开部分地提供大网络聚合物珠粒以及制备方法和使用它们的方法。本公开还提供从一种或更多种靶标金属离子或金属离子络合物与其他离子掺混的溶液中选择性地隔绝出一种或更多种靶标金属离子或靶标金属离子络合物的方法。例如,本公开提供了在Au(CN)2 -存在下选择性地隔绝Hg(CN)4 2-以及在其他金属盐类例如钠盐、镁盐、钙盐、铁盐等存在下选择性地隔绝Li+和Sc(CO3)3 3-的方法。本公开进一步解决了对这样的新MIP技术(包括MIP材料、生产此类MIP材料的方法以及使用此类MIP材料的方法)的需求,所述新MIP技术可用来以良好收率选择性隔绝期望靶标分子、离子和/或络合物,且对靶标离子或离子络合物的除去效率高,对靶标离子或络合物有良好容量,且如果特定行为应用的要求有此需求时可以再生。此外,本公开提供了用于制备高表面积MIP以允许高选择性和高容量的独特方法。这对于大量低质量离子或分子的隔绝和/或除去特别重要。此外,这种方法允许使用悬浮聚合方法进行生产,所述方法生产的产品具有允许在广泛的应用和工艺条件下使用的质量(硬度、稳定性、pH值耐受性等)。
本公开的一个实施方案涉及多个大网络聚合物珠粒,其包含具有多个选择性地结合靶标金属离子络合物的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)一种或更多种与非金属替代二价阴离子或三价阴离子络合的阳离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子络合物的电荷相反,和
(ⅱ)非金属替代二价阴离子或三价阴离子具有与靶标金属离子络合物基本相同的形状和电荷。
在另一个实施方案中,本公开涉及多个大网络聚合物珠粒,其包含具有多个选择性地结合与一种或更多种阴离子配体络合的靶标金属离子的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)一种或更多种与替代阳离子络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子的电荷相反,
(ⅱ)替代阳离子具有与靶标金属离子基本相同的形状和电荷,和
(ⅲ)靶标金属离子对配体单体的结合亲和力高于替代阳离子。
在另一个实施方案中,本公开涉及多个大网络聚合物珠粒,其包含具有多个选择性地结合靶标金属离子的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)一种或更多种与靶标金属离子络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中该共聚物包含多于约50mol%的阴离子配体单体。
另一个实施方案涉及制备如本文所述的大网络分子印迹聚合物珠粒的方法,其包括使以下物质聚合:
(a)一种或更多种与非金属替代二价阴离子或三价阴离子络合的阳离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体,
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子络合物的电荷相反,和
(ⅱ)非金属替代二价阴离子或三价阴离子具有与靶标金属离子络合物基本相同的形状和电荷。
另一个实施方案涉及制备大网络分子印迹聚合物珠粒的方法,其包括使以下物质聚合:
(a)一种或更多种与替代阳离子如Ca2+络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子的电荷相反,
(ⅱ)替代阳离子具有与靶标金属离子基本相同的形状和电荷,和
(ⅲ)靶标金属离子对配体单体的结合亲和力高于替代阳离子。
另一个实施方案涉及制备如本文所述的大网络分子印迹聚合物珠粒的方法,其包括使以下物质聚合:
(a)一种或更多种与靶标金属离子络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)该共聚物含有多于约50mol%的阴离子配体单体。
一些实施方案涉及从一种或更多种靶标金属离子与其他离子掺混的溶液中选择性地隔绝出一种或更多种靶标金属离子的方法,其包括首先使大网络聚合物珠粒与洗提溶液接触,借此从大网络聚合物珠粒中除去非金属替代离子,然后使经洗提的珠粒与溶液接触,从而选择性地将靶标离子隔绝在大网络聚合物珠粒中。
除非另有定义,本文使用的所有技术和科学术语都具有与本公开所属领域的普通技术人员通常理解相同的含义。在发生冲突的情况下,将以本说明书(包括定义)为准。在说明书中,单数形式也包括复数形式,上下文另有外明确规定的除外。尽管与本文所述的那些方法和材料类似或等效的方法和材料可用于本公开的实施或测试,但下文描述了适合的方法和材料。本文提及的所有出版物、专利申请、专利和其他参考文献都出于所有目的以引用的方式并入本文。不承认本文引用的参考文献是所要求保护的发明的先前技术。此外,材料、方法和实例仅为说明性的而非意图进行限制。
从以下具体实施方式和权利要求书看,本公开的其他特征和优点将显而易见。
附图说明
图1是MIP生产工艺的示意图。
具体实施方式
本公开在各实施方案中涉及用于制备分子印迹聚合物(“MIP”)吸收剂或材料的改进方法、通过此类工艺制备的MIP吸收剂或材料,以及利用本公开的MIP吸收剂或材料的改进工艺。
基于吸收的工艺常常被设计用于从混合物中分离、提取或隔绝出特定分子物质或“靶标”分子,以隔离出靶标分子(例如由于它的价值),从混合物中除去特定物质(例如由于它的毒性或其他危险性质),或检测靶标分子(或与靶标分子相关的分子)。分子印迹聚合物是具有高选择性的吸收剂,其具有专门为结合特定靶标分子而定制的吸收位点。已知MIP以及制备和使用MIP的方法的实例包括美国专利号7,067,702、7,319,038、7,476,316、7,678,870、8,058,208、8,591,842和美国序列号15/176,758中公开的那些实例,所述美国专利都出于所有目的以引用的方式整体并入本文。这些MIP是通过使靶标分子的可聚合配体(即“配体单体”)在由一种或更多种非配体单体(例如苯乙烯或其他不与靶标分子形成络合物的单体)和一种或更多种交联剂组成的聚合物基体中聚合来制备的共聚物。按照惯例,MIP特有的“模板化”吸收位点通过如下方式制备:形成配体单体与靶标分子的适当络合物,然后使所得靶标分子-配体单体络合物在一种或更多种非配体单体和至少一种交叉联接试剂存在下在合适的聚合条件下聚合。所得聚合物结构包含具有分散的结合位点或空腔(“络合空腔”)的聚合的非配体单体(一种或多种)的基体,所述结合位点或空腔含有仍然与(现时是聚合的)配体单体络合的靶标分子。因为聚合是在靶标分子存在下进行,所以靶标分子形成“模板”,使得络合空腔的尺寸和形状是特定靶标分子所特有的,从而导致相对于其他分子,与靶标分子具有高选择性的结合。用于制备MIP材料的模板化工艺的示意图在图1中示出。
如上所讨论,尽管利用靶标分子作为分子模板提供了对于结合靶标分子而言最优的高选择性络合空腔,但常规MIP制造工艺由于在制造时需要使用靶标分子自身而造成了显著的制造和/或按比例放大问题。大规模制造因此将需要使用大量靶标分子,如果靶标分子是昂贵的、相对难以获得的的、有毒的、有放射性的、干扰MIP的聚合等,或这些因素的任何组合,那么这可能是一个特殊的问题(甚至在小规模制造的情况下亦是如此)。
令人惊讶的是,申请人已发现通过用适当选择的“替代”分子替代靶标分子,常规MIP的选择性优势可被保留而不需要使用靶标分子自身作为结合位点的模板。如本文将例示,对靶标分子“A”具有选择性的MIP可通过使适合的替代分子“B”与配体单体(一种或多种)的络合物、非配体单体(一种或多种)和交联单体(一种或多种)聚合来制备,前提是“A”和“B”使用相同物理化学机理与配体单体络合,具有类似尺寸和/或形状,并且“B”相较于“A”具有一个或多个以下特点:价格较低廉,危险性(即毒性、放射性)较小,或与聚合条件更加相容。所得“替代”模板化MIP,尽管也许对靶标分子的选择性稍微小于使用常规工艺(其中靶标分子充当分子模板)制备的那些,但价格更低廉,制备更安全,更容易制造和按比例放大等,还在例如分离或提取应用中具有足够的选择性从而在性能上类似于常规MIP,但成本显著较低。此外,本公开的“替代”模板化MIP由于以相对低廉成本组合了高性能而在总体分离工艺成本方面提供大幅度的改进。
尽管本文公开的MIP材料和方法的各种例示实施方案涉及阳离子MIP,但是可根据靶标分子的化学结构和特征,采用用于结合特定靶标分子的任何合适的物理化学相互作用。可用来制备根据本公开的MIP材料的介于配体单体与靶标分子之间的各种不同物理化学相互作用包括共价、离子、离子-偶极、氢键合、偶极-偶极、诱导偶极或瞬时偶极-诱导偶极(即伦敦分散(London dispersion))吸引性相互作用,以及使库仑和立体排斥性相互作用最小化。当靶标分子是离子(例如“靶标离子”,如本文所述的任何金属二价阴离子和三价阴离子络合物)时,可以方便地通过选择具有携带互补电荷的离子官能团的配体单体来利用离子相互作用。例如,当靶标离子是阳离子时,配体单体包括能够与阳离子靶标离子形成络合物的阴离子官能团(例如羧酸根、磺酸根、膦酸根或其他酸式盐),并且当靶标离子是阴离子(例如二价阴离子或三价阴离子)时,配体单体包括阳离子官能团(例如季铵离子),或由1-(4-乙烯基吡啶-2-基)甲亚胺或类似可聚合亚胺类(亚胺氮原子上任选地被本文所述的烷基取代)制备的且能够与阴离子靶标离子络合的不带电荷的配体,或可聚合冠醚,例如二苯并-14-冠-4或苯并-12-冠-4(其中可聚合部分可包括本文所述的任何可聚合部分,例如丙烯酸酯类、甲基丙烯酸酯类、乙烯基团等,如果需要,可带有任何合适的连接基团)。当靶标分子为中性(即,没有有效电荷)时,合适的不带电荷的配体单体包括但不限于包括诸如亚胺类(如本文所述)、胺类、膦类、酯类、醚类、穴醚类、硫醚类、席夫碱类等官能团的单体。中性靶标分子通常包括例如小有机分子,诸如但不限于杀虫剂、药物分子、放射性示踪剂等。在使配体单体与一种或更多种不带电荷的单体和一种或更多种交叉联接单体聚合形成MIP珠粒之前,将配体单体与替代离子(或在某些情况下,靶标离子)混合,这允许配体单体“自组装”或与替代离子(或靶标离子)配位,以便在聚合期间将替代离子(或靶标离子)掺合到聚合的MIP珠粒中。根据需要,替代离子(或靶标伴侣)可在使用前通过用适当的可替换离子置换而从珠粒中除去,或者可在使用前保持在原位。
适合的替代物可通过首先表征靶标分子的尺寸、形状和相关物理化学特性来进行选择。具有类似分子形状和尺寸以及类似物理化学特性的候选替代分子然后可以通过例如使用可商购获得的分子建模程序诸如 Ultra 14.0进行分子建模来鉴定。例如,如果靶标分子是离子性的,那么将选择与靶标离子具有类似尺寸、形状和电荷的替代离子。有利的是,替代物应相对廉价,无毒,并且不干扰聚合(即不应与配体单体形成高度不稳定的络合物,使聚合催化剂中毒,抑制引发剂,与其他单体或聚合溶剂反应,不溶于聚合溶剂等)。这些各种因素的平衡使得适合于各种靶标分子和分离过程的替代物选择变得无法预测。
可聚合配体,例如4-乙烯基苄基三正丁基氯化铵和如本文所述的其他阳离子配体,已被设计用于从水溶液中提取阴离子金属盐。此类可聚合配体可在水中溶解,直至与阴离子,例如二价阴离子如2,2'-(1,4-亚苯基)二乙酸根(也称为1,4-亚苯基二乙酸根)或三价阴离子如三甲磺酸根反应或络合,然后从溶液中沉淀出来。所得沉淀可溶于有机溶剂。该阴离子模拟特定靶标金属阴离子如Sc(CO3)3 2-或Au(S2O3)2 3-的分子形状和电荷。然后,使所得配体/阴离子络合物聚合到疏水性聚合物基体,例如苯乙烯中,以形成多孔珠粒或颗粒,然后可利用所得珠粒或颗粒从水溶液中选择性地除去期望的金属阴离子(例如,Sc(CO3)3 2-或Au(S2O3)2 3-)。
在另一个实施方案中,根据本公开的MIP可在结合空腔中包括这样的单体配体,该单体配体对靶标阴离子络合物的金属阳离子组分的亲和力大于靶标离子络合物的阴离子配体的亲和力。例如,各种采矿工艺流形成Hg(CN)4 2-络合物。尽管Hg(CN)4 2-可被视为“靶标离子络合物”,且可以制备对四氰酸根络合物具有选择性的MIP,替代途径是制备具有比CN-更强地与Hg2+结合或配位的配体单体的MIP。在此类MIP中,替代离子将是阳离子(而不是阴离子),并且配体单体的配体部分将为阴离子(而不是阳离子),对该阴离子进行选择从而使其比CN-更强地与Hg2+结合以及与替代阳离子相比更强地与Hg2+结合。对于Hg2+,此类配体单体可以包括可聚合的二硫代氨基甲酸盐,例如4-乙烯基苄基二硫代氨基甲酸盐,并且替代物可以是二价阳离子,例如Ca2+。在使用中,具有此类二硫代氨基甲酸根络合位点的MIP将在Hg(CN)4 2-络合物存在下选择性地结合Hg2+,因为二硫代氨基甲酸根部分比CN-更强地与Hg2+配位。
使用配体/替代物(例如二价阴离子、三价阴离子、羧酸根或二硫代氨基甲酸根)络合物生产离子选择性MIP树脂,提供了一种优于现有离子交换树脂的材料,所述材料例如提高了对靶标离子的选择性,在使用期间维持更好的活性,减少了对用于使靶标离子与其他竞争离子交换结合位点的物质分离的多个工艺步骤的需要,并改善了再生性能。在制备MIP时使用此类“替代物”而非靶标离子还降低了用于开发和按比例放大分子印迹聚合物树脂的总成本,以及减少了潜在危险废物的量和/或对靶标分子的回收(供进一步使用)和它们的相关处理成本。
根据本公开的MIP珠粒可具有在从近似球形至细长不规则形状(例如类似于松软干酪凝块的不规则形状)的范围内的任何合适的形状,或形成为特定的期望形状。
在各实施方案中,期望分子印迹聚合物呈珠粒形式,特别是具有足够的孔隙率以便使进出珠粒的质量输送容易进行的多孔珠粒。
术语“珠粒”是指平均粒度在约250μm至约1.5mm的范围内的多个颗粒。在一些实施方案中,珠粒的平均粒度可为约250μm、约300μm、约350μm、约400μm、约450μm、约500μm、约550μm、约600μm、约650μm、约700μm、约750μm、约800μm、约850μm、约900μm、约950μm、约1000μm、约1050μm、约1100μm、约1150μm、约1200μm、约1250μm、约1300μm、约1350μm、约1400μm、约1450μm或约1500μm,包括介于这些值中的任何一者之间的任何范围。在具体的实施方案中,平均粒度范围是约0.3mm至1.1mm。
在一些实施方案中,本公开的MIP珠粒具有基本单峰的粒度分布。在其他实施方案中,期望MIP珠粒具有双峰或其他多峰的粒度分布。
在许多工艺中,材料处理或质量流量要求决定了细颗粒的百分比低。因此,在具体实施方案中,少于约10%的本公开的MIP珠粒具有小于约250μm的粒度。在其他实施方案中,少于约5%或少于约1%的珠粒具有小于约250μm的粒度。珠粒的平均粒度可通过包括例如ASTM D 1921-06在内的本领域中一般已知的各种分析方法测量。
在大多数实施方案中,期望本公开的珠粒是多孔的,以促进质量流进出珠粒。在具体实施方案中,本公开的MIP珠粒的特征是“大网络”或“大孔”,其指的是存在平均孔隙直径大于100nm的孔隙的网络。在各实施方案中,制备平均孔隙直径在100nm至2.4μm范围内的聚合物珠粒。
在一些实施方案中,平均孔隙直径可为约100nm、约200nm、约300nm、约400nm、约500nm、约600nm、约700nm、约800nm、约900nm、约1000nm、约1100nm、约1200nm、约1300nm、约1400nm、约1500nm、约1600nm、约1700nm、约1800nm、约1900nm、约2000nm、约2100nm、约2200nm、约2300nm或约2400nm,包括介于这些值中的任何一者之间的范围。
珠粒还可为中孔的,或包括中孔(除包括大孔之外)。术语“中孔”是指平均孔隙直径为10nm至100nm的多孔网络。在一些实施方案中,中孔平均孔隙直径可为约10nm、约15nm、约20nm、约25nm、约30nm、约35nm、约40nm、约45nm、约50nm、约55nm、约60nm、约65nm、约70nm、约75nm、约80nm、约85nm、约90nm、约95nm或约100nm,包括介于这些值中的任何一者之间的任何范围。
此外,珠粒还可为微孔的,或者除包括大孔和/或中孔之外还包括微孔。术语“微孔”是指平均孔隙直径小于10nm的多孔网络。在一些实施方案中,微孔平均孔隙直径可为约0.5nm、约1nm、约1.5nm、约2nm、约2.5nm、约3nm、约3.5nm、约4nm、约4.5nm或约5nm或约5.5nm、约6nm、约6.5nm、约7nm、约7.5nm、约8nm、约8.5nm、约9nm、约9.5nm或约10nm,包括介于何这些值中的任何一者之间的范围。
大网络聚合物珠粒具有约0.1至约500m2/g,例如约0.1、约0.5、约1、约5、约10、约15、约20、约30、约40、约50、约60、约70、约80、约90、约100、约150、约200、约250、约300、约350、约400、约450或约500m2/g(包括介于其间的所有范围和子范围)的表面积。
珠粒的结构和孔隙率主要由聚合条件决定。期望的珠粒孔隙率可通过挑选替代物/配体单体络合物、非配体单体和交联试剂以及它们的量,以及反应溶剂(一种或多种)的组成和任选的孔形成添加剂或触变剂来获得。孔隙率决定可进入特定结构的物质、分子或离子的尺寸以及它们的扩散和交换速率,以及质量流进出珠粒结构的速率。
触变剂可显著改进对珠粒形成和基本均一珠粒或粒度的控制。本文采用的合适触变剂取决于所采用的单体的类型和量以及悬浮介质。触变剂还可在悬浮聚合工艺期间有利地充当悬浮剂。此类触变剂的代表性实例包括但不限于纤维素醚类(如羟乙基纤维素(可以商标名“CELLOSIZE”商购获得))、交叉联接的聚丙烯酸(如以商品名“CARBOPOL”而为人所知的那些)、聚乙烯醇类(如以商品名“RHODOVIOL”而为人所知的那些)、硼酸、胶类(如黄原胶)等,以及它们的混合物,触变剂的量可影响树脂的尺寸(即,使用较大量的触变剂常常导致形成较小的树脂粒子)。
基于单体混合物中单体的重量,触变剂的量一般是约1.5至约5重量百分比。在一些实施方案中,基于单体混合物中一种单体或多种单体(单体的组合)的重量,触变剂的量是约1.5至约2.5重量百分比。
本公开的珠粒可通过各种聚合技术来制备。聚合物基体可然后通过合适的聚合技术在替代物/配体单体络合物存在下来形成以形成印迹树脂。然后,可以回收树脂产品。合适的聚合技术的非限制性实例可包括水相悬浮聚合、反相悬浮聚合(例如在全氟化碳中)、非水相分散聚合、两阶段溶胀聚合、气溶胶聚合、乳胶种子乳液聚合、电聚合和在多孔珠粒基底上进行的本体聚合。在一个实施方案中,聚合方法是以下两者的可共聚混合物的水相悬浮聚合:含有非配体单体、任选交联剂和替代物/配体单体络合物的有机相与含有至少一种或更多种触变剂的水相。
根据本公开的非共价电聚合分子印迹聚合物(E-MIP)可用作用于检测药物和其他化学物质的具有高选择性的化学敏感性超薄膜。电聚合是一种用于制备MIP改性电极的策略。将具有特殊选择性的MIP膜沉积在可例如用于分析生物流体中的蛋白质或用于药物、农业、食品和环境(例如水处理)分析中的检测器的表面上。
在本公开的某些实施方案中,MIP是通过使替代物/配体单体络合物和如本文所述的其他单体悬浮聚合来制备。在悬浮聚合程序中,可在开始反应之前单独彻底混合各个相,然后将该各个相添加到聚合反应容器中。尽管这个成分混合可在除反应容器以外的容器中进行,但该混合可供替代地在聚合反应容器中在惰性氛围下进行,特别是在所采用的单体易受氧化影响时。此外,为改进最终树脂产物的产率和选择性,期望配体单体在聚合条件下以及在最终产物中具有水解稳定性。例如,配体单体可在悬浮聚合配方中以及在水处理环境下具有水解稳定性,以使得在聚合和树脂的有用期限期间基本上避免水解。
可使本公开的可聚合配体/替代物络合物在悬浮聚合条件下聚合,在所述悬浮聚合条件中,水相含有在水中的触变剂诸如聚乙烯醇和硼酸,并且有机相包含例如可聚合配体/替代物络合物、苯乙烯(非配体单体)、二乙烯基苯(交叉联接单体)、有机溶剂和AIBN(引发剂)。例如用搅拌器搅拌两相混合物。通过改变温度、搅拌、可聚合配体/替代物负载量、溶剂比率和交叉联接程度,可获得不同的珠粒结构和性质。例如,具有期望尺寸的球形和多孔珠粒可通过控制聚合过程中的搅拌或搅动来获得。当搅拌聚合混合物以使溶解于有机反应介质中的单体以液滴形式分散在水相内时,适合的是所述液滴具有这样的尺寸,其使得当转化成聚合物珠粒时,它们是基本球形和多孔的,并且具有期望的尺寸。不适合的反应条件可导致不形成珠粒或形成极小珠粒,替代物在水相中的损失高,总产率低,以及孔隙率不足以致存在向络合空腔的不良质量传递。在具体实施方案中,配体单体是可聚合铵盐,诸如一种本文公开的可聚合铵盐,并且替代物是阴离子,例如一种本文公开的阴离子。在更具体的实施方案中,配体单体是可聚合的4-乙烯基苄基铵盐,并且替代物是硫氰酸根、连五硫酸根、间苯二甲酸根、磷酸根或琥珀酸根。
聚合可在任何合适温度下进行。在一些实施方案中,该反应在高温例如高于约50℃下在任选引发剂的存在下进行。可使用的适合的引发剂包括但不限于过氧化苯甲酰、过氧化二乙酰和偶氮二异丁腈(AIBN)。基于被聚合的单体的重量,采用的引发剂的量可在约0.005至约1.00重量%的范围内。在引发剂存在下,使反应温度维持在引发剂变得具有活性所处的温度以上。如果施加高能辐射来引发聚合,那么可采用较低的温度例如约-30℃至约200℃。苯乙烯聚合可以加热引发。
在整个聚合中进行的适当和足够搅拌或搅动通常提供具有期望尺寸的基本球形的多孔珠粒。例如,可搅拌聚合混合物以通过剪切作用来使单体(溶解于溶剂有机相中)分散在水性溶剂相中,由此形成液滴。通过选择适当的搅拌水平,所述液滴可具有这样的尺寸,其使得当转化成聚合物珠粒时,它们是基本球形和多孔的,并且将具有如本文讨论的期望尺寸。
有多种工具可用来维持适当的搅拌。当在由不锈钢制成的反应器中进行聚合时,此种反应器可配备有具有一个或多个搅拌器叶片的可旋转轴。当圆底烧瓶用作反应器时,可利用顶置式搅拌器搅拌反应介质。为获得期望结果所必需的搅拌量将随着被聚合的特定单体以及期望的特定聚合物珠粒尺寸而变化。因此,可在某一限度内调控搅拌速度诸如rpm(每分钟转数)。根据单体的反应性,聚合时间可在约3小时至约72小时间变化。
当聚合完成时,可从通常交叉联接的聚合物珠粒中除去替代物而不大幅度地影响络合空腔。替代分子的除去提供了例如具有其中具有互补分子空腔的多孔结构的珠粒,其对靶标分子(或离子)具有高结合亲和力。例如,当替代物是连四硫酸根、连五硫酸根或连六硫酸根;己基二酮酸根、庚基二酮酸根或辛基二酮酸根,1,4-亚苯基二醋酸根,或丁烷二磺酸根、戊烷二磺酸根或己烷二磺酸根(用于提供Au(S2O3)2 3-选择性空腔)时,通过用10M HCl溶液冲洗,可从珠粒中的结合位点除去(“洗提”)替代物以提供适合于隔绝来自例如采矿浸出工艺的Au(S2O3)2 3-的配体/硫酸根络合物。类似地,当替代物是苯均三酸的三碱盐(用于提供Sc(CO3)3 3-选择性空腔)时,通过用浓盐酸和醇如甲醇冲洗,可以从珠粒中的结合位点上除去相应替代物,以提供适合于隔绝如本文所述的相应离子的MIP。在其他实施方案,例如含Ca2+替代物和二硫代氨基酸根配体(用于提供Hg2+选择性空腔以处理含Hg(CN)4 2-的混合物)的MIPS中,则不需要除去替代离子,因为在使用时Hg2+对二硫代氨基甲酸根配体的强且优选的结合将实现Ca2+的置换。
根据特定树脂和经处理的液体介质,本公开的各种MIP材料可再次使用(再生)一次以上,并且常常再次使用多达约30次或更多次。再生可以以与原始印迹离子的除去几乎相同的方式实现,例如用适当溶液洗提或洗涤来实现。
在其他实施方案中,未对MIP材料进行再生。例如,在产生Hg(CN)4 2-废物流的采矿工艺中,一旦Hg选择性MIP(如本文所述)达到Hg2+容量的期望水平,即可根据相关的环境和其他监管标准处置Hg饱和的MIP。类似地,如果靶标离子具有足够的价值(例如,Au(S2O3)2 3-或Sc(CO3)3 3-),与再生Au-或Sc-选择性MIP相比,在氧化条件下通过燃烧从MIP“破坏性地”回收Au或Sc金属可能更经济。
大网络MIP珠粒特别可用于从溶液中选择性地除去或吸附靶标溶解物质,所述溶液例如是水流,例如饮用水、湖泊、溪流、工业流出物流、采矿提取流和废物流等。在一个实施方案中,本公开的MIP珠粒由配体单体制备,所述配体单体是离子性的例如阳离子性(用于与阴离子络合)或阴离子性(用于与阳离子络合)。
在具体实施方案中,本公开的MIP珠粒可用于选择性地从采矿作业隔绝金属,例如汞。此类金属的开采通常涉及:将金和/或银矿石(含汞杂质)破碎,然后用浓氰化物溶液从破碎的矿石中提取金属,形成含有可溶性氰化物络合物,例如Hg(CN)4 2-和尤其其他各种铜盐、镍盐、锌盐、钴盐、铬盐和铁盐的水溶液。由于汞盐的毒性,期望选择性地除去汞盐而不影响贵金属(金和银)的收率。
每年生产的所有金中约60%是通过金-氰化物工艺(GCP)的一些变化形式来获得。对于合适的GCP溶液,活性炭是用于除去二氰合金酸根的最常见隔绝衬底,占提取的所有金的一半以上(或在2004年超过1250吨)。活性炭制造成本低廉,易于吸收金,对金具有相当的选择性,并且具有大的金负载容量。不幸的是,活性炭也对四氰化汞(II)具有高亲和力,并且在一些条件下,四氰化汞(II)可实际上从活性炭置换二氰合金酸根。从活性炭洗脱时,四氰化汞(II)与二氰合金酸根一起解吸。四氰化汞(II)也在分离金属金的电解沉积工艺期间被还原成元素汞。在这两种情况下,元素汞都会产生健康和环境危害,并且补救成本高昂。此外,对于活性炭,洗脱工艺不是100%高效,并且有一些微量的汞残留在活性炭上。随后,在对活性炭进行热再活化后,汞被热还原成汞金属,其接着挥发并逃逸至大气中。再活化步骤不可避免,因为活性炭也吸收可结垢并大幅度地降低它的容量的有机物质。
因此,用于汞提取工艺的更高效的选择性吸收剂,可用作现有采矿活动或废液处理的预滤器(它们在排除贵金属靶标例如金和银时对汞有高亲和力),将显著降低贵金属采矿(及后续提取)工艺中的资金和操作成本。本公开的MIP吸收剂提供此类改进的吸收剂。
汞是已在黄金开采和石化行业的各种地下资源中发现的一种不期望的元素。由于环境原因以及特别是石化领域的腐蚀问题,它的存在对于这两个行业来说是一个令人头疼的问题。在黄金开采过程中期望专门除去汞而不会意外地除去金,因此根据本发明的方法用二硫代氨基甲酸钙络合物(见下文)制备的MIP,适合于从各种组合物中专门除去汞而不影响在下游吸收车间金的吸收。合适的R基团包括C4-C24烷基,包括直链和支链饱和烷基,例如C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23或C24支链或直链烷基。在制备MIPS期间钙的作用是充当占位元素(与汞的电荷相同、离子半径几乎相同),直到所得MIP中形成吸收空腔。钙可以通过酸洗除去,或者如上文所讨论按原样简单地使用,因为二硫代氨基甲酸根对汞具有非常高的亲和力。此类MIP树脂将是“只用一次的(oneand done)”材料而不需要再生,因此可以大幅度增加活性位点的数量以提高总容量。合适的容量,汞容量范围为每克MIP至少约15、20、25、30、35、40或更多克汞。此类一次性材料的结构完整性相对于MIPS对汞的整体亲和力和容量而言是次要的。
4-乙烯基苄基二硫代氨基甲酸钙络合物
钪是一种需求不断增长的金属,因为它能够显著增加轻质合金如铝的强度。钪目前采用高酸性浸滤剂进行开采。在此类条件下,在浸滤剂中发现元素形式的金属,包括钪和其他金属。离子交换树脂在此类情况下不具有选择性,因为在钪矿床中发现的许多金属具有三个电荷(如钪)。因此,用于获得钪的常规工艺包括一组复杂的提取、分离和沉淀步骤,以获得纯度甚至适中的钪。在混合物中各种金属之间的区别可能仅依赖于大小和形状的此类情况下,本发明的钪选择性MIP材料提供了钪的选择性提取。
通常,含钪矿石用酸处理,酸除了溶解钪外还溶解矿石中包含的其他金属。这些金属中有许多,例如铁和铝像钪一样也是三价的。因此,使用常规的非选择性吸收介质难以将它们与钪分离。然后,例如用碱式碳酸盐将酸性混合物或金属盐制成碱性物质,并将钪阳离子转化为三碳酸钪。虽然形成沉淀的铁和铝是碱性溶液,但其他金属(例如,稀土金属、铀、钛、钨、镍、钽和/或铌,取决于矿石)被带入其中。使用设计用于选择性地结合Sc(CO3)3 3-的配体单体和替代物制备的本文所述的MIP组合物,能够从此类混合物中以高选择性和容量除去Sc(CO3)3 3-。
在一个实施方案中,本公开的MIP可用于在存在其他REMS的情况下检测和/或选择性地除去稀土金属(REM)如Sc(CO3)3 3-或稀土元素(REE)。由于REE的理化性质非常相似这一事实,使用常规分离方法将它们彼此分离可能非常困难。然而,使用如本文所公开的本发明MIPS可以高效地进行Sc与REM的此类分离。
本公开的REM或REE被定义为周期表中一组17种化学元素之一,特别是十五种镧系元素(例如,铈(Ce)、镝(Dy)、铒(Er)、铕(Eu)、钆(Gd)、钬(Ho)、镧(La)、镥(Lu)、钕(Nd)、镨(Pr)、钷(Pm)、钐(Sm)、铽(Tb)、铥(Tm)、镱(Yb)以及钪(Sc)和钇(Y)。
锂开采是以各种方式完成。其中一种比较流行的方法包括将水注入含锂的盐矿床中,然后在大块土地上蒸发所得的含锂水以通过蒸发除去水。沉降后,接着例如通过经由一系列膜、过滤器和吸收介质从溶液中提取锂来进一步加工锂盐和许多其他组分的混合物。在此类情况下,使用对锂有选择性的MIP提供了一种基本上瞬时收集高纯度锂的方法,并且需要少很多的加工和使用水来获得商业上可用的纯度水平的锂。
大型锂矿床和其他金属矿床也与被开发用来提供地热能的热卤水相关。在此类情况下,高压和热卤水被泵送到地面。利用换热器将地热能转换为蒸汽,以驱动蒸汽涡轮机产生电力,并且必须保持卤水在足够的压力和温度下,以防止盐类和其他溶解的物质沉淀并允许将冷却后的卤水注回地层。目前没有提取技术可用于提取这些热卤水溶液中的溶解金属,同时保持主要地热能生产过程的完整性。本发明的锂选择性MIP材料能够在这种环境中运作,并且可以提取商业上有用、有价值的数量的足够的锂;每年实现高达2万吨锂的生产水平。
由于锂的低原子质量和作为商品的适中价值,为锂创造经济的MIP具有挑战性。为了使基于MIP的工艺成本具有成本竞争力,实际上整个MIP需要包含配体单体组分。一种制备成本有效的锂选择性MIP的方式是通过反相悬浮聚合(RPSP)制备此类MIP。总的来说,RPSP的工作原理与“常规”悬浮聚合几乎相同,只是在RSPS中,所有聚合都发生在水相(而不是有机相)中,而有机相(而不是水相)充当载体。水相包含水、印迹离子(在本实例中为Li+)、一种或更多种水溶性配体单体、一种或更多种水溶性交叉联接剂和水溶性引发剂(如Wake VA-44)。在一些实施方案中,可根据需要加入少量非配体单体,例如以对所得MIP的物理性质进行改性。有机相(载体相)可与煤油一样简单。RPSP用于制备例如锂用极高容量MIP的优势在于,水溶性配体单体不需要庞大的有机基团(像烃溶性配体单体那样)来保持它溶解在发生聚合的悬浮聚合混合物的相中。
根据本发明的此类锂选择性MIPS具有至少约15、20、25或30mg Li+/g MIP的容量。
在大多数实施方案中,使用替代物作为模板而不是靶标分子制备的本公开的MIP材料,与常规离子交换树脂相比提供了更好的性能。常规的离子交换材料可以为靶标分子(例如本文所述的锂盐、钪盐或汞盐)提供相对高的初始负载,但是在使用中容量迅速降低,在相对少量的洗脱循环后需要更换且在使用期间提取容量下降。常规离子交换树脂很容易因洗脱循环期间未除去的其他金属如铜的存在而“中毒”。此外,常规离子交换树脂可能对pH值变化敏感。由于树脂珠粒在再生期间结合并释放离子,因此珠粒在使用中也会膨胀和收缩。随着时间的推移和在特定的外部条件(例如,再生过程中的水力冲击、氯和氯胺降解、结垢(颗粒和有机物)、氧化、渗透冲击以及反洗产生的基本损耗)下,等等,珠粒会弱化和分解。
相反,本公开的MIP材料对靶标金属具有高选择性。尽管一些常规离子交换树脂与本公开的MIPS相比可能具有较高的总容量,但由于本发明的MIPS对靶标离子具有较高的选择性,因此本公开的MIPS与常规离子交换树脂相比每单位重量吸收更多的靶标离子(达到约25mg Li+/g MIP、约5-15mg Sc3+/g MIP、约10-35mg Hg2+/g MIP),在使用期间具有更好的容量保持和较低的吸收变化性以及较低的再生/洗脱成本。另外,本公开的MIP材料制造成本大幅度低于用靶标分子本身作为络合空腔模板的MIP材料,并且与常规离子交换树脂相当或略微更昂贵。因此,本公开的MIP材料与围绕常规吸收剂(例如,活性炭、常规离子交换树脂、含靶标分子的常规MIP树脂模板等)设计的常规工艺相比,可以提供大幅度降低的资金和工艺成本。
已提出用于提取贵金属和其他金属的常规MIP珠粒(例如美国专利号7,746,316),因为相较于常规离子交换树脂(或炭),对贵金属离子的较高选择性允许MIP珠粒的床体积较小,但因为常规MIP珠粒使用靶标贵金属离子作为MIP珠粒的模板加以制备,所以制备大量MIP珠粒需要的成本过高。此外,很多金属络合物是有毒的,并且单体配体/络合物难以大量操作或大量操作时不稳定。因此,尚无实际或商业上可行的方式来在满足商业应用要求所需的规模上制备使用上述专利的MIP珠粒。
虽然美国序列号15/176,758中已描述了使用替代离子来制备MIPS,但选择合适的替代离子和/或配体单体以制备商业上可接受的且有用的选择性、耐用性MIPS材料是不可预测和复杂的,因为这需要鉴定具有适当电荷和分子形状的替代物以模拟期望的靶标离子,该靶标离子与配体单体(一种或多种)形成与聚合条件相容的稳定络合物,形成具有适宜孔隙率和机械特性的珠粒,并提供在使用条件下最终将与靶标离子强烈络合的MIPS。鉴定满足这些各种要求的替代物和配体单体是困难的。在一些情况下,鉴定出具有适当电荷和分子形状的替代离子,但是它们与所需的聚合条件或与MIP珠粒中使用的其他单体不相容。在其他情况下,对其他方面合适的配体进行改性以使其可聚合(例如,添加可聚合的乙烯基),得到聚合时不再与期望的靶标离子结合的配体单体。因此,尽管使用替代物制备MIP珠子的概念在理论上似乎是简单直接的,但是鉴定适合于特定应用的配体单体(和其他单体)和替代离子的组合的实际问题需要相当多的实验。
此外,即使使用如本文公开的替代物制备的MIP珠理论上比使用靶标离子作为模板制备的MIP珠选择性差,但与常规吸收剂如活性炭或常规离子交换树脂相比,本公开的MIP珠粒提供大幅度的成本节约。在采矿作业中,本公开的MIP珠粒可以使总提取率增加(3)%至(5)%,并且可以使运行成本降低多达60%。在有些情况下,所提出的MIP可提供唯一可行的提取技术。这些树脂珠粒基本上可被加塞置入工厂的当前操作中,而不进行工厂重新设计。此外,由于它们相较于常规MIP材料具有较低制造成本,所以本公开的“替代”MIP材料对于提取较低价值的金属(例如铜、锂等)(在这种情况下常规MIP材料将极其昂贵)具有成本效益。
出于类似原因,在通过使用这些靶标离子对MIP珠粒模板化来制备的常规MIP珠粒的情况下,用MIP珠粒处理废水流以除去有毒的金属络合物(例如Hg(CN)4 2-)同样是不切实际且在商业上不可行的,因为相应处理工艺的规模将在MIP生产工艺中需要相应大量的这些危险金属络合物。
在制备MIP吸收剂方面的此类按比例放大问题可通过如下方式来规避:在制备MIP时用仔细选择的与靶标离子具有近似相同形状、尺寸和电荷的替代离子替代作为模板的相应靶标离子,以便在MIP中产生与将已使用靶标离子自身作为模板产生的那些络合空腔类似的络合空腔。然而,相比于靶标离子,替代物的花费更少且更可易于获得,毒性较小,与配体单体形成足够稳定的络合物,并且另外不损害使MIP聚合的能力。例如,用于制备适合于选择性地结合分子印迹用双-二硫代硫酸金(Au(S2O3)2 3-)的分子印迹聚合物的合适替代物包括无机或有机二价阴离子,例如(但不限于)连四硫酸根、连五硫酸根或连六硫酸根,己基二酮酸根、庚基二酮酸根、辛基二酮酸根,1,4-亚苯基二乙酸根,或丁烷二磺酸根、戊烷二磺酸根、己烷二磺酸根。用于制备适合于选择性地结合Hg(CN)4 2-的分子印迹聚合物的合适替代物是用钙作为反离子的间苯二甲酸盐或二硫代氨基甲酸盐(见上文)。用于制备适合于选择性地结合三碳酸钪的分子印迹聚合物的合适替代物包括苯均三酸的三碱盐(苯-1,3,5-三羧酸盐)或苯-1,3,5-三基三羧酸的三碱盐。
锂既不是非常昂贵的金属,也不是非常有毒的金属,并且其本身可以用作传统的分子印迹模板。然而,锂的原子质量非常低(6.9g/mol)并且锂的价值适中,这将需要MIP具有大量活性位点以便在经济上可行。此类MIP可以具有1-(4-乙烯基吡啶-2-基)甲亚胺配体单体,且具有很少或没有惰性单体或交叉联接试剂。在常规MIP组合物中,非配体单体与配体单体的摩尔比通常为约50:1,而在本公开的高容量锂选择性MIP材料中,非配体单体与配体单体的摩尔比要低得多,低于约10:1、9:1、8:1、7:1、6:1、5:1、4:1、3:1、2:1或约1:1。在一些实施方案中,锂选择性MIP中配体单体的重量百分比为约99%、约95%、约90%、约85%、约80%、约75%、约70%、约65%、约60%、约55%或约50%,包括其间的所有范围和子范围。在一些实施方案中,1-(4-乙烯基吡啶-2-基)甲亚胺配体单体可构成全部或几乎全部的MIP。1-(4-乙烯基吡啶-2-基)甲亚胺配体单体也可以被官能化以包括与配体的甲亚胺官能团附连的长烷基(R基团),从而改善双(1-(4-乙烯基吡啶-2-基)甲亚胺)配体单体络合物在悬浮聚合条件下的溶解度。合适的R基团包括C4-C24烷基,包括直链和支链饱和烷基,例如C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15、C16、C17、C18、C19、C20、C21、C22、C23或C24支链或直链烷基。在一些实施方案中,1-(4-乙烯基吡啶-2-基)甲亚胺配体单体可为此类用不同R基团官能化的配体单体的混合物。在其他实施方案中,1-(4-乙烯基吡啶-2-基)甲亚胺配体单体全部具有相同的R基团。
在常规方法中,目标通常是使吸收剂对待除去或待隔绝的期望靶标物质的选择性最大化。这对于使用MIP材料作为吸收剂的工艺尤其如此,因为MIP材料对MIP材料制备中用作模板的靶标分子显示出极高的选择性。然而,由以靶标分子作为模板制备的MIP材料(即常规MIP材料)提供的额外选择性不能转化成显著工艺优势,特别是用于对MIP材料模板化的靶标分子昂贵、有毒、难以获得或干扰MIP材料自身的聚合时。此类因素可急剧增加制造MIP材料的成本,并且由此抵消由较高选择性所带来的任何加工优势。
本发明申请人已发现在许多工艺中,它足以提供对期望靶标分子的选择性显著高于溶液中其他物质的MIP材料,或换句话说,足以提供对待分离混合物中的非靶标物质的选择性显著较小或排斥所述非靶标物质的MIP材料。
使用合适替代物而非靶标分子(例如离子)制备的MIP材料(例如珠粒或大网络珠粒)对靶标分子(例如离子)具有选择性。MIP材料结合“A”和物质“B”的混合物中的物质“A”的选择性,可通过使用以下关系式的“选择性系数”来表征:
其中:“[A]”和“[B]”是指溶液中A和B的摩尔浓度,并且“[A’]”和“[B’]”是指MIP材料中络合的“A”和“B”的浓度。
对于通过使用靶标分子对络合空腔模板化制备的常规MIP材料,对靶标分子的选择性系数将高于其他物质,因为络合空腔是针对靶标分子的形状、尺寸、电荷等进行最佳地配置的。对于使用替代分子而非靶标分子对MIP材料模板化,根据本公开制备的MIP材料,对替代分子的选择性系数将高于例如靶标分子,但MIP材料对靶标分子的选择性将仍然显著高于对待分离混合物中的其他溶解物质。对于大多数分离,相对于对待分离混合物中的其他物质,对靶标离子的选择性系数应为至少约10、至少约11、至少约12、至少约13、至少约14、至少约15、至少约20、至少约25、至少约30、至少约35、至少约40、至少约45、至少约50、至少约55、至少约60、至少约70、至少约80、至少约90、至少约100、至少约200、至少约300、至少约400、至少约500,包括介于这些值中的任一者之间的范围。
如本文所用,术语“结合(bind)”、“结合(binding)”、“键(bond)”、“键合(bonded)”或“键合(bonding)”是指通过电子或质子的共享和交换,原子间相互吸引,从而使化学物质合成一体的物理现象。该术语包括键类型,例如:离子键、配位键、氢键、共价键、极性共价键或配位共价键。用于键的其他术语,例如香蕉键、芳族键或金属键,也包括在该术语的含义内。选择性结合相互作用是指如本文所述的由MIP对离子(阴离子或阳离子)展现的优先和可逆结合。
本公开的一个实施方案涉及多个大网络聚合物珠粒,其包含具有多个选择性地结合靶标金属离子络合物的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)一种或更多种与非金属二-或三阴离子络合的配体单体,
(b)一种或更多种不带电荷(非配体)单体,和
(c)一种或更多种交联单体;
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子络合物的电荷相反,和
(ii)非金属替代二价阴离子或三价阴离子具有与靶标金属离子络合物基本相同的形状和电荷。
在另一个实施方案中,本公开涉及多个大网络聚合物珠粒,其包含具有多个选择性地结合与一种或更多种阴离子配体络合的靶标金属离子的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)一种或更多种与替代阳离子络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子的电荷相反,
(ⅱ)替代阳离子具有与靶标金属离子基本相同的形状和电荷,和
(ⅲ)靶标金属离子对配体单体的结合亲和力高于替代阳离子。
在另一个实施方案中,本公开涉及a多个大网络聚合物珠粒,其包含具有多个选择性地结合靶标金属离子的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)一种或更多种与靶标金属离子络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中共聚物包含多于[50mol%?]的阴离子配体单体。
另一个实施方案涉及制备如本文所述的大网络分子印迹聚合物珠粒的方法,其包括使以下物质聚合:
(a)一种或更多种与非金属替代二价阴离子或三价阴离子络合的阳离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体,
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子络合物的电荷相反,和
(ⅱ)非金属替代二价阴离子或三价阴离子具有与靶标金属离子络合物基本相同的形状和电荷。
另一个实施方案涉及制备大网络分子印迹聚合物珠粒的方法,其包括使以下物质聚合:
(a)一种或更多种与替代阳离子如Ca2+络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)络合空腔中共聚物的电荷与靶标金属离子的电荷相反,
(ⅱ)替代阳离子具有与靶标金属离子基本相同的形状和电荷,和
(ⅲ)靶标金属离子对配体单体的结合亲和力高于替代阳离子。
另一个实施方案涉及制备如本文所述的大网络分子印迹聚合物珠粒的方法,其包括使以下物质聚合:
(a)一种或更多种与靶标金属离子络合的阴离子配体单体,
(b)一种或更多种不带电单体,和
(c)一种或更多种交联单体;
其中:
(i)该共聚物含有多于50mol%的阴离子配体单体。
本公开的配体单体包括单齿、双齿和多齿配体,例如N,N,N-三戊基-N'-乙烯基苄基铵。给定阳离子或阴离子分子印迹聚合物珠粒所需的配体的量和类型,将取决于靶标化合物和相关配体上可用的配位点的数量。
在其他实施方案中,配体单体是可聚合的亚胺,例如1-(4-乙烯基吡啶-2-基)甲亚胺以及如本文所述的它的烷基化衍生物。
靶标阳离子配体络合物可通过提供整体稳定的络合物的配体与靶标化合物的组合来形成。本公开的方法包括限制聚合期间的氧化/还原(氧化还原)副反应的靶标阳离子配体络合物。在一个实施方案中,相对于SCE(标准甘汞电极),靶标阳离子配体络合物具有至少0.3eV的氧化还原电势。另外,靶标阳离子配体络合物可在各种pH范围下形成。在一个实施方案中,靶标阳离子配体络合物可在1至13的pH值范围内形成。在另一实施方案中,靶标阳离子配体络合物可在5至9的pH值范围内聚合。
在一些实施方案中,配体分子是硬碱配体,该配体的特征在于具有可聚合基团,例如乙烯基。
配体单体的可聚合基团可包括本领域中的任何常规可聚合基团,例如乙烯基、苯乙烯基、丙烯酰基、甲基丙烯酰基等,或任何本文公开的任何单体的任何可聚合基团。在一些实施方案中,非金属替代离子是有机阴离子。本公开的非金属或有机替代二价阴离子或三价阴离子,具有与靶标金属离子基本相同的形状和电荷。
基本相同的尺寸和形状意指,如果叠加在彼此上以使在由空间填充模型限定的体积之间的重叠最大化(例如借助于商业分子建模程序如 Ultra 14.0所确定),那么靶标分子(例如靶标阴离子)的空间填充模型和替代物(例如非金属替代离子/有机阴离子)的空间填充模型将相差不多于约50%,例如不多于约50%、不多于约45%、不多于约40%、不多于约35%、不多于约30%、不多于约25%、不多于约20%、不多于约15%、不多于约10%或不多于约5%,包括介于其之间的所有范围和子范围。
替代地,尺寸和形状与靶标分子基本相同的替代物可通过所得MIP材料对靶标分子(例如靶标离子)的选择性进行功能上的定义。由于本发明MIP材料的络合空腔由替代分子而非靶标分子加以模板化,所以该MIP材料对替代物质的选择性将高于对靶标分子的选择性。然而,就替代分子的尺寸和形状将与靶标分子的尺寸和形状基本相同而言,所得MIP材料将对靶标分子具有相对较高的选择性系数。因此,对靶标分子的选择性较高将指示靶标的尺寸和形状与替代分子的尺寸和形状基本类似。在一些实施方案中,用替代分子进行模板化的本公开的MIP材料对靶标分子的选择性系数大于约10。在其他实施方案中,本公开的MIP材料的选择性系数大于:约15、约20、约25、约30、约35、约40、约45、约50、约100、约150、约200、约300、约400、约500、约600、约700、约800、约900或约1000,包括介于其之间的所有范围。
Au(S2O3)2 3-的具体而非限制性的非金属替代离子可包括连四硫酸根、连五硫酸根或连六硫酸根,己基二酮酸根、庚基二酮酸根、辛基二酮酸根,1,4-亚苯基二乙酸根,或丁烷二磺酸根、戊烷二磺酸根、己烷二磺酸根。Hg(CN)4 2-的具体而非限制性的替代离子是Ca2+。钪的具体而非限制性的非金属替代离子是苯均三酸的三碱盐(苯-1,3,5-三羧酸盐)或苯-1,3,5-三基三羧酸的三碱盐。。
申请人惊讶地发现,用于选择性地除去锂盐的商业上可用的MIPS可以在不使用替代离子的情况下制备。锂的具体而非限制性的配体单体是1-(4-乙烯基吡啶-2-基)甲亚胺或可聚合的冠醚。
在一些实施方案中,大网络聚合物珠粒包含具有多个选择性地结合靶标金属离子的络合空腔的共聚物,并且其中所述共聚物由阳离子配体单体制备。
在一些实施方案中,靶标金属离子是Hg(CN)4 2-,替代离子是Ca2+,并且配体单体是可聚合的二硫代氨基甲酸盐。
在一些实施方案中,靶标金属离子是三碳酸钪,并且非金属替代离子是苯均三酸(苯-1,3,5-三羧酸根)或苯-1,3,5-三基三羧酸根。
在一些实施方案中,靶标金属离子是Au(S2O3)2 3-,非金属替代物是连四硫酸根、连五硫酸根或连六硫酸根,己基二酮酸根、庚基二酮酸根、辛基二酮酸根,1,4-亚苯基二乙酸根,或丁烷二磺酸根、戊烷二磺酸根或己烷二磺酸根。
在一些实施方案中,靶标金属离子是Li(盐?),并且配体单体是1-(4-乙烯基吡啶-2-基)甲亚胺,其任选地被如本文所述的C4-C24支链或直链烷基取代。如本文所述选择用于锂的MIPS是在不与替代离子形成络合物的情况下制备的。
多种多样的单体可用作非配体单体用于合成根据本公开的MIP。可用于制备本公开MIP的非配体单体的合适的非限制性实例包括甲基丙烯酸甲酯、其他甲基丙烯酸烷基酯、丙烯酸烷基酯、丙烯酸烯丙酯或丙烯酸芳酯和甲基丙烯酸烯丙酯或甲基丙烯酸芳酯、氰基丙烯酸酯、苯乙烯、取代的苯乙烯、甲基苯乙烯(多取代的),包括1-甲基苯乙烯;3-甲基苯乙烯;4-甲基苯乙烯等;乙烯基酯,包括乙酸乙烯酯、氯乙烯、甲基乙烯基酮、偏二氯乙烯、丙烯酰胺、甲基丙烯酰胺、丙烯腈、甲基丙烯腈、2-乙酰胺基丙烯酸;甲基丙烯酸2-(乙酰氧基乙酰氧基)乙酯;1-乙酰氧基-1,3-丁二烯;2-乙酰氧基-3-丁烯腈;4-乙酰氧基苯乙烯;丙烯醛;丙烯醛二乙基缩醛;丙烯醛二甲基缩醛;丙烯酰胺;2-丙烯酰胺基乙醇酸;2-丙烯酰胺基-2-甲基丙烷磺酸;丙烯酸;丙烯酸酐;丙烯腈;丙烯酰氯;1-α-丙烯酰基氧基-β,β-二甲基-γ-丁内酯;N-丙烯酰氧基丁二酰亚胺丙烯酰氧基三(羟甲基)氨基-甲烷;N-丙烯酰氯;N-丙烯酰基吡咯烷酮;N-丙烯酰基-三(羟甲基)氨基甲烷;甲基丙烯酸2-氨基乙酯;N-(3-氨基丙基)甲基丙烯酰胺;(邻、间或对)-氨基-苯乙烯;甲基丙烯酸叔戊酯;甲基丙烯酸2-(1-氮杂环丙烷基)乙酯;4-苯甲基氧基-3-甲氧基苯乙烯;2-溴丙烯酸;4-溴-1-丁烯;3-溴-3,3-二氟丙烷;6-溴-1-己烯;3-溴-2-甲基丙烯腈;2-(溴甲基)丙烯酸;8-溴-1-辛烯;5-溴-1-戊烯;顺-1-溴-1-丙烯;-溴苯乙烯;对溴苯乙烯;溴三氟乙烯;(±)-3-丁烯-2-醇;1,3-丁二烯;1,3-丁二烯-1,4-二甲酸3-丁烯醛二乙基缩醛;1-丁烯;3-丁烯-2-醇;氯甲酸3-丁烯酯;2-丁基丙烯醛;叔丁基丙烯酰胺;丙烯酸丁酯;甲基丙烯酸丁酯;(邻、间、对)-溴苯乙烯;丙烯酸叔丁酯;1-香芹酮;(S)-香芹酮;乙酸(-)-香芹酯;3-氯丙烯酸;2-氯丙烯腈;2-氯乙基乙烯醚;2-氯甲基-3-三甲基甲硅烷基-1-丙烯;3-氯-1-丁烯;3-氯-2-氯甲基-1-丙烯;3-氯-2-甲基丙烯;2,2-双(4-氯苯基)-1,1-二氯乙烯;3-氯-1-苯基-1-丙烯;间氯苯乙烯;邻氯苯乙烯;对氯苯乙烯;乙酸1-氰基乙烯酯;1-环丙基-1-(三甲基甲硅烷氧基)乙烯;2,3-二氯-1-丙烯;2,6-二氯苯乙烯;1,3-二氯丙烯;2,4-二乙基-2,6-庚二烯醛;1,9-癸二烯;1-癸烯;1,2-二溴乙烯;1,1-二氯-2,2-二氟乙烯;1,1-二氯丙烯;2,6-二氟苯乙烯;二氢香芹醇;(±)-二氢香芹酮;乙酸(-)-二氢香芹酯;3,3-二甲基丙烯醛;N,N’-二甲基丙烯酰胺;3,3-二甲基丙烯酸;3,3-二甲基丙烯酰氯;2,3-二甲基-1-丁烯;3,3-二甲基-1-丁烯;甲基丙烯酸2-二甲基氨基乙酯;1-(3-丁烯基)-4-乙烯基苯;2,4-二甲基-2,6-庚二烯-1-醇;2,4-二甲基-2,6-庚二烯醛;2,5-二甲基-1,5-己二烯;2,4-二甲基-1,3-戊二烯;2,2-二甲基-4-戊烯醛;2,4-二甲基苯乙烯;2,5-二甲基苯乙烯;3,4-二甲基苯乙烯;1-十二碳烯;3,4-环氧基-1-丁烯;2-乙基丙烯醛;丙烯酸乙酯;2-乙基-1-丁烯;丙烯酸(±)-2-乙基己酯;甲基丙烯酸(±)-2-乙基己酯;2-乙基-2-(羟甲基)-1,3–丙二醇三丙烯酸酯;2-乙基-2-(羟甲基)-1,3–丙二醇三甲基丙烯酸酯;甲基丙烯酸乙酯;乙基乙烯基醚;乙基乙烯基酮;乙基乙烯基砜;(1-乙基乙烯基)三丁基锡;间氟苯乙烯;邻氟苯乙烯;对氟苯乙烯;乙二醇甲基丙烯酸酯(甲基丙烯酸羟乙酯);GA GMA;1,6-庚二烯;1,6-庚二烯酸;1,6-庚二烯-4-醇;1-庚烯;1-己烯-3-醇;1-己烯;六氟丙烯;1,6-己二醇二丙烯酸酯;1-十六碳烯;1,5-己二烯-3,4-二醇;1,4-己二烯;1,5-己二烯-3-醇;1,3,5-己三烯;5-己烯-1,2-二醇;5-己烯-1-醇;丙烯酸羟丙酯;3-羟基-3,7,11-三甲基-1,6,10-十二碳三烯;甲基丙烯酸异戊酯;甲基丙烯酸异丁酯;异戊二烯;2-异丙烯基苯胺;氯甲酸异丙烯酯;二甲基丙烯酸4,4’-亚异丙酯;异氰酸3-异丙基-a-a-二甲基苯;异蒲勒醇;衣康酸;衣康酰氯;(±)-里哪醇;乙酸里哪酯;对薄荷-1,8-二烯;对薄荷-6,8-二烯-2-醇;亚甲基氨基乙腈;甲基丙烯醛;[3-(甲基丙烯酰基氨基)-丙基]三甲基氯化铵;甲基丙烯酰胺;甲基丙烯酸;甲基丙烯酸酐;甲基丙烯腈;甲基丙烯酰氯;乙酰乙酸2-(甲基丙烯酰基氧基)乙酯;(3-甲基-丙烯酰氧基丙基)三甲氧基甲硅烷;2-(甲基丙烯酰基氧基)乙基三甲基甲基硫酸铵;2-甲氧基丙烯(异丙烯基甲基醚);2-(溴甲基)丙烯酸甲酯;5-甲基-5-己烯-2-酮;甲基丙烯酸甲酯;N,N’亚甲基双丙烯酰胺;2-亚甲基戊二腈;2-亚甲基-1,3-丙二醇;3-甲基-1,2-丁二烯;2-甲基-1-丁烯;3-甲基-1-丁烯;3-甲基-1-丁烯-1-醇;2-甲基-1-丁烯-3-炔;2-甲基-1,5-庚二烯;2-甲基-1-庚烯;2-甲基-1-己烯;3–甲基-1,3-戊二烯;2-甲基-1,4-戊二烯;(±)-3-甲基-1-戊烯;(±)-4-甲基-1-戊烯;(±)-3-甲基-1-戊烯-3-醇;2-甲基-1-戊烯;甲基乙烯基醚;甲基-2-乙烯基环氧乙烷;甲基乙烯基砜;4-甲基-5-乙烯基噻唑;香叶烯;t-硝基苯乙烯;3-硝基苯乙烯;1-十九碳烯;1,8-壬二烯;1-十八碳烯;1,7–辛二烯;7–30辛烷-1,2-二醇(7–30ctane-1,2-diol);1-辛烯;1-辛烯-3-醇;1-十五碳烯;1-戊烯;1-戊烯-3-醇;t-2,4-戊烯酸;1,3-戊二烯;1,4-戊二烯;1,4-戊二烯-3-醇;4-戊烯-1-醇;4-戊烯-2-醇;4-苯基-1-丁烯;苯基乙烯基硫醚;乙烯基磺酸苯酯;2-丙烯-1-磺酸钠盐;苯基乙烯基亚砜;1-苯基-1-(三甲基甲硅烷氧基)乙烯;丙烯;黄樟素(safrole);苯乙烯(乙烯基苯);4-苯乙烯磺酸钠盐;苯乙烯磺酰氯;3-磺丙基丙烯酸钾盐;3-磺丙基甲基丙烯酸钠盐;四氯乙烯;四氰乙烯;反3-氯丙烯酸;2-三氟甲基丙烯;2-(三氟甲基)丙烯酸;2,4,4’-三甲基-1-戊烯;3,5-双(三氟甲基)苯乙烯;2,3-双(三甲基甲硅烷氧基)-1,3-丁二烯;1-十一碳烯;乙酸乙烯酯;乙烯基乙酸;4-乙烯基苯甲醚;9-乙烯基蒽;山嵛酸乙烯酯;苯甲酸乙烯酯;乙酸乙烯基苯甲酯;乙烯基苯甲醇;3-乙烯基氯甲苯;3-(乙烯基苯甲基)-2-氯乙基砜;4-(乙烯基苯甲基)-2-氯乙基砜;N-(对乙烯基苯甲基)-N,N’-二甲基胺;4-乙烯基联苯(4-苯基苯乙烯);溴乙烯;2-乙烯基丁烷;乙烯基丁基醚;9-乙烯基咔唑;乙烯基甲醇;乙烯基鲸蜡基醚;氯乙酸乙烯酯;氯甲酸乙烯酯;巴豆酸乙烯酯;乙烯基过氧环己烷;4-乙烯基-1-环己烯;4-乙烯基环己烯二氧化物;乙烯基环戊烯;乙烯基二甲基氯甲硅烷;乙烯基二甲基乙氧基甲硅烷;乙烯基二苯基膦;2-乙基己酸乙烯酯;乙烯基2-乙基己基醚;乙烯基醚酮;乙烯基乙烯;乙烯基亚乙基三羰基铁;乙烯基二茂铁;甲酸乙烯酯;乙烯基十六基醚;偏二氟乙烯;1-乙烯基喹啉;碘乙烯;月桂酸乙烯酯;乙烯基溴化镁;乙烯基均三甲苯;乙烯基2-甲氧基乙基醚;乙烯基甲基二氯甲硅烷;乙烯基甲基醚;乙烯基甲基酮;2-乙烯基萘;5-乙烯基-2-降冰片烯;壬酸乙烯酯;苯基乙酸乙烯酯;乙烯基膦酸、双(2-氯乙基)酯;丙酸乙烯酯;4-乙烯基吡啶;2-乙烯基吡啶;1-乙烯基-2-吡咯烷酮;2-乙烯基喹啉;1-乙烯基杂氮硅三环;乙烯基砜;乙烯基磺酸钠盐;a-乙烯基甲苯;对乙烯基甲苯;乙烯基三乙酰氧基甲硅烷;乙烯基三丁基锡;三氯乙烯;乙烯基三氯甲硅烷;乙烯基三氯甲硅烷(三氯乙烯基甲硅烷);乙烯基三乙氧基甲硅烷;乙烯基三乙基甲硅烷;三氟乙酸乙烯酯;乙烯基三甲氧基甲硅烷;乙烯基三甲基壬基醚;乙烯基三甲基甲硅烷;乙烯基三苯基溴化膦鎓(三苯基乙烯基溴化膦鎓);乙烯基三-(2-甲氧基乙氧基)甲硅烷;2-戊酸乙烯酯等。
丙烯酸酯封端或以其他方式不饱和的氨基甲酸酯、碳酸酯和环氧树脂也可用于MIP中。不饱和碳酸酯的实例是烯丙基二乙二醇碳酸酯。不饱和环氧树脂包括但不限于丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、烯丙基缩水甘油醚和1,2-环氧基-3-烯丙基丙烷。
对MIP赋予刚性或结构完整性的交叉联接(也叫交联)试剂或交叉联接单体为本领域技术人员所知,并且包括二官能性、三官能性和四官能性丙烯酸酯或甲基丙烯酸酯、二乙烯基苯(DVB)、亚烷基二醇和聚亚烷基二醇二丙烯酸酯和甲基丙烯酸酯,包括乙二醇二甲基丙烯酸酯(EGDMA)和乙二醇二丙烯酸酯、丙烯酸乙烯酯或丙烯酸烯丙酯或甲基丙烯酸乙烯酯或甲基丙烯酸烯丙酯,二乙烯基苯、二烯丙基二甘醇二碳酸酯、马来酸二烯丙酯、富马酸二烯丙酯、衣康酸二烯丙酯、乙烯基酯诸如草酸二乙烯酯、丙二酸二乙烯酯,丁二酸二烯丙酯、异氰脲酸三烯丙酯、双酚A或乙氧基化双酚A的二甲基丙烯酸酯或二丙烯酸酯、亚甲基或聚亚甲基双丙烯酰胺或铋-丙烯酰胺,包括六亚甲基双丙烯酰胺镧化物或六亚甲基双甲基丙烯酰胺,二(烯)叔胺、三甲醇丙烷三丙烯酸酯、季戊四醇四丙烯酸酯、二乙烯基醚、二乙烯基砜、苯二甲酸二烯丙酯、三烯丙基蜜胺、甲基丙烯酸2-异氰酸基乙酯、丙烯酸2-异氰酸基乙酯、丙烯酸3-异氰酸基丙酯、甲基丙烯酸1-甲基-2-异氰酸基乙酯、丙烯酸1,1-二甲基-2-异氰酸基乙酯、四乙二醇二丙烯酸酯、四乙二醇二甲基丙烯酸酯、三乙二醇二丙烯酸酯、三乙二醇二甲基丙烯酸酯、己二醇二甲基丙烯酸酯、己二醇二丙烯酸酯、二乙烯基苯;1,3-二乙烯基四甲基二硅氧烷;8,13-二乙烯基-3,7,12,17-四甲基-21H,23H-卟吩;8,13-二乙烯基-3,7,12,17–四甲基-21H,23H-丙酸;8,13-二乙烯基-3,7,12,17-四甲基-21H,23H-丙酸二钠盐;3,9-二乙烯基-2,4,8,10-四氧杂螺[5,5]十一烷;二乙烯基二氯化锡等。
MIP必须具有足够刚性以使靶标离子可易于除去而不影响聚合物的完整性。在聚合物基体没有足够的刚性的此类情况下,可引入交联剂或其他硬化剂。在印迹MIP中,交叉联接剂(交叉联接试剂或单体)实现三个主要功能:1)交叉联接剂在控制聚合物基体的形态方面是重要的,无论其是凝胶型、大孔或微凝胶粉末;2)它起到稳定印迹结合位点(络合空腔)的作用;和3)它赋予聚合物基体机械稳定性。在具体实施方案中,一般期望高的交叉联接率,以便提供具有足够的机械稳定性的永久多孔材料。
可使用有效地使本公开的单体聚合从而产生MIP而不使配体/替代物络合物解离的任何合适的条件。本公开的单体可通过自由基聚合等来聚合。本领域技术人员所知的任何UV或热自由基引发剂都可用于优选的自由基聚合中。UV和热引发剂的实例包括过氧化苯甲酰、过氧化乙酰、过氧化月桂酰、偶氮基双异丁腈(AIBN)、过乙酸叔丁酯、过氧化异丙苯、叔丁基过氧化物;叔丁基氢过氧化物、过氧基-二碳酸双(异丙基)酯、安息香甲基醚、2,2'-偶氮双(2,4-二甲基-戊腈)、过氧辛酸叔丁酯、邻苯二甲酸过氧化物、二乙氧基苯乙酮、过氧化新戊酸叔丁酯、二乙氧基苯乙酮、1-羟基环己基苯基酮、2,2-二甲基氧基-2-苯基苯乙酮和吩噻嗪、磺原酸二异丙酯二硫化物、2,2'-偶氮双-(2-脒基丙烷);2,2'-偶氮基双异丁腈-;4,4'-偶氮双-(4-氰基戊酸);1,1’-偶氮双-(环己烷甲腈)-;2,2'-偶氮双-(2,4-二甲基戊腈);等及其混合物。
单体和交叉联接试剂的挑选将由聚合物所期望的化学(亲水性、化学稳定性、交叉联接程度、接枝于其他表面的能力、与其他分子的相互作用等)和物理(孔隙率、形态、机械稳定性等)性质决定。应挑选配体单体/替代物络合物、单体和交联剂的量,以提供表现出期望的结构完整性、孔隙率和亲水性的交联聚合物。根据所选配体/替代物络合物、单体和交联剂的具体性质/反应性以及聚合物将最终应用的具体应用和环境,该量可广泛变化。可改变每种反应物的相对量,以达到期望的配体/替代物络合物在聚合物载体结构中的浓度。通常,配体替代物络合物的量将大约为单体的约0.01mmol%至约100mmol%,包括:单体的约0.02、0.05、0.1、0.2、0.3、0.5、1、2、3、4、5、10、15、20、25、30、35、40、45、50、55、60、65、70、75、80、85、90、95或100mmol%。交叉联接剂的量通常大约为单体的约1.0至约10mol%,包括约1.5、2、3、4、5、6、7、8或9mol%。自由基引发剂的量可为单体的约0.005至1mol%,包括约0.01、0.05、0.1、0.5、0.6、0.7、0.8或0.9mol%。(摩尔百分比是指相对于在聚合之前单体总量的百分比。)
在一些情况下,期望的待提取金属具有极低的质量,例如锂。商业上可用于大量提取该金属的MIP必须具有庞大数量的收集位点。因此,如本文所述的配体包括所有或几乎所有用于制备具有很少或没有支撑聚合物骨架和交联的MIP的单体。此类配体单体必须被官能团化并且能在悬浮聚合条件下溶解,并且必须仍得到保持适合于商业用途的聚合物质量(刚性、选择性、再利用能力、温度和耐pH能力)的最终聚合形式。本发明的MIP材料在约0-13的pH值范围(包括约0、1、2、3、4、5、6、7、8、9、10、11、12和13,包括其间的所有范围)、约0-100℃的温度范围(包括约0、10、20、30、40、50、60、70、80、90、100℃,包括其间的所有范围)内是稳定的(物理上和化学上稳定的),其质量损耗小于约20wt.%(包括少于约20、15、10、9、8、7、6、5、4、3、2、1、0.5或约0wt.%,包括其间的所有范围),能稳定到至少约20个you周期(包括约2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19或20,包括其间的所有范围)并且对期望靶标离子的选择性系数(如本文所述)为至少约40(包括至少约40、45、50、55、60、65、70、75、80、85、90、95或100,包括其间的所有范围)。可改变溶剂、温度和聚合方式以便获得具有最优物理或化学特征例如孔隙率、稳定性和亲水性的聚合材料。溶剂也将基于它溶解反应混合物的所有各种组分和形成期望的聚合物形态的能力加以挑选。
交联程度可在约1%至约95%的范围内。在一些实施方案中,交联程度是约5%至约80%。
可使用提供合适的溶解性并且可与形成本公开的MIP材料的条件所需的反应相容的任何溶剂。在通过悬浮聚合条件制备MIP材料的一些实施方案中,溶剂可为有机溶剂的混合物。例如,溶剂可包括长链脂族醇诸如戊醇、己醇、庚醇、辛醇、壬醇、癸醇、十一醇、十二醇(包括其饱和和不饱和异构体(例如甲基和乙基戊醇、甲基和乙基己醇、甲基和乙基庚醇等))、脂族烃(例如丁烷、戊烷、己烷、庚烷等)、芳族烃(例如苯、甲苯、二甲苯等)及其组合。
由此获得的树脂呈多孔珠粒形式。多孔珠粒可具有开放的孔眼结构,使得珠粒内的大部分开放体积彼此之间以及与珠粒表面上的外部开口相互连接。
在一个实施方案中,本公开提供了从一种或更多种靶标金属离子与其他离子掺混的溶液中选择性地隔绝出所述一种或更多种靶标金属离子的方法,其包括首先使本公开的大网络聚合物珠粒与洗提溶液接触,借此从所述大网络聚合物珠粒中除去非金属替代离子,然后使经洗提珠粒与所述溶液接触,由此选择性地将所述靶标离子隔绝在所述大网络聚合物珠粒中。然后用能够置换靶标离子的离子溶液从珠粒中洗提经隔绝的靶标离子,由此使珠粒再生以再次用于隔绝靶标离子。
本公开提供了MIP的制备方法。MIP可通过对已知技术进行修改来制备,所述技术包括但不限于美国专利号4,406,792、4,415,655、4,532,232、4,935,365、4,960,762、5,015,576、5,110,883、5,208,155、5,310,648、5,321,102、30 5,372,719、5,786,428、6,063,637和6,593,142以及美国申请号15/176,158中所述的那些,所述美国专利及美国申请中每一篇的整个内容出于所有目的以引用的方式整体并入本文。
使用MIP技术制备的本公开的大网络珠粒也可用于从水性介质例如饮用水、湖泊、溪流、灌溉径流、工业流出物、采矿废物等中除去污染物。
在整个说明书中,当将方法或工艺描述为具有、包括或包含具体工艺步骤时,该工艺也基本上由所述加工步骤组成,或由所述加工步骤组成。此外,应了解,步骤的顺序或执行某些动作的顺序是不重要的,只要方法保持可操作即可。此外,两个或更多个步骤或动作可同时进行。
实施例
实施例1大网络珠粒的制备
配体的示例性合成
双(N-(4-乙烯基苄基)-N-癸基-N,N-二甲基铵)连五硫酸盐的示例性合成:
在配备有微型搅拌棒的20mL小瓶中将N-(4-乙烯基苄基)-N-癸基-N,N-二甲基氯化铵(1.08g,3.2mmol)溶解于去离子(DI)水(3mL)中。也将硫代硫酸钠(1g,4mmol)溶解于DI水(0.67mL)中,并且向其中加入配体溶液。溶液立即变稠、变黏,添加额外的DI水(3mL)以使该溶液变稀。在搅拌下用冰浴使溶液冷却至0℃。历经一分钟的过程逐滴添加浓盐酸(0.67mL)。白色物质快速形成,其接着被黄色油状物所替代,将所述黄色油状物从溶液分离。使混合物在4℃下沉降过夜。次日,轻轻倒出水相,并且用水(5ml)洗涤残余物。使残余物真空干燥以产生在0℃以下变为蜡状的油状物(1.30g,94%产率)。产物在4℃下稳定储存数周而无可觉察的降解。NMR(400MHz,CDCl3,估计值7.54-7.36(dd,8H);6.68–6.60(dd,2H);5.78–5.73(d,2H);5.31–5.28(d,2H);4.78(s,4H);3.30–3.28(t,4H);3.15(s,12H);1.70(bs,4H);1.25–1.19(m,28H);0.84(t,6H)。
N-(4-乙烯基苄基)-N,N,N-三正戊基硫氰酸铵的示例性合成:
使配备有侧臂的圆底烧瓶脱气,加热至80℃,并且维持在惰性氛围下。添加10mL乙腈,接着添加4-乙烯基苄基氯和三正戊基胺(用分子筛干燥)(11.37g,50mmol,TCIAmerica),并且保持在惰性氛围下。使混合物在80℃下反应六(6)小时。在真空下除去乙腈,并且将残余物溶解于25mL乙醚中。产物(N-(4-乙烯基苄基)-N,N,N-三正戊基氯化铵)是白色固体。通过将乙醚添加至产物中并使用5.5cm中等快速定性滤纸(Medium FastQualitative filter)过滤来用25mL乙醚洗涤产物两次。产物是白色蓬松固体,使其在真空下干燥3小时。
将N-(4-乙烯基苄基)-N,N,N-三正戊基氯化铵(7.60g,20mmol)溶解于水(50mL)中。将含硫氰酸钾(1.94g,20mmol)的水(30mL)以5mL/min的速率添加至配体溶液中。形成白色沉淀,并且有油状物从溶液沉降。将油状物冷藏过夜。轻轻倒出水溶液,并且用50mL水洗涤残余物。使残余物真空干燥以产生油状物(N-(4-乙烯基苄基)-N,N,N-三正戊基硫氰酸铵),其在0℃以下变为玻璃状(定量产率:8.05g)。
示例性悬浮聚合
制备水相
通过温和加热至80℃来将聚乙烯醇(PVOH,平均Mw 89,000-98,000,99+%水解,10.26g)溶解于水(540mL)中。将4.42g硼酸溶解于135mL水中,并且当PVOH冷却至50℃时缓慢添加。
制备有机相和聚合
使5g络合物与48.75mL乙基己醇和1.25mL二甲苯在配备有搅拌棒的100mL锥形瓶中合并,并且使其搅拌直至完全溶解。使35.88mL苯乙烯和13.68mL二乙烯基苯与络合物的溶液合并,并且在环境条件下,使其搅拌,用隔膜覆盖。将0.5g AIBN添加至溶液中,并且使其完全溶解。当溶解时,将溶液添加至加料漏斗中,并且进行脱气直至反应温度达到75℃。当温度达到80℃时,以1mL/s的速率向溶液中添加水相。使反应在连续搅拌下进行约8小时。
反应后珠粒清理
在反应完成后,通过过滤从水溶液中回收珠粒。接着将珠粒浸渍在去离子水(200mL)中10分钟,接着过滤。将在去离子水中浸渍和过滤重复两次。将珠粒在甲醇中洗涤两次,并且在丙酮中洗涤两次。期望时,可使用适当网筛根据尺寸对珠粒进行分级。然后在活化之前在5至50℃的温度下可将珠粒无限期地储存在水中。
珠粒活化
将湿珠粒放置到大型备有夹套的玻璃柱中,并且除去所有夹带的空气。然后将柱加热至50℃,并且以0.1个床体积/分钟的速率添加硫酸铁水合物溶液(0.22M),持续15个床体积。然后在环境温度至50℃下用水(10个床体积)冲洗珠粒。本发明的锂选择性MIP可利用酸洗进行活化。本发明的钪选择性MIP可在50℃下用酸/醇洗(1M盐酸或硫酸/甲醇)进行活化。本发明的汞选择性MIP可以用酸洗活化,或者可以按生产原样使用而不作活化。
Claims (14)
1.多个大网络聚合物珠粒,其包含具有多个选择性地结合Au(S2O3)2 3-的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)与选自由以下离子组成的组的非金属替代离子络合的阳离子配体单体:连四硫酸根、连六硫酸根,己基二酮酸根、庚基二酮酸根、辛基二酮酸根,1,4-亚苯基二乙酸根,丁烷二磺酸根、戊烷二磺酸根和己烷二磺酸根,
(b)非配体单体,和
(c)交联单体;
其中所述络合空腔中共聚物的电荷与所述靶标金属离子的电荷相反。
2.多个大网络聚合物珠粒,其包含具有多个选择性地结合三碳酸钪的络合空腔的共聚物,其中所述共聚物由以下物质制备:
(a)与苯-1,3,5-三基-三羧酸的三碱盐络合的阳离子配体单体,
(b)非配体单体,和
(c)交联单体;
其中所述络合空腔中共聚物的电荷与所述靶标金属离子的电荷相反。
3.如权利要求1或2所述的大网络珠粒,其中所述阳离子配体单体是选自由以下组成的组的可聚合阳离子:铵、吡啶鎓、吡咯烷鎓、咪唑鎓、胍鎓、膦鎓和硫鎓。
4.如权利要求3所述的大网络珠粒,其中所述阳离子配体单体是4-乙烯基苄基铵。
5.如权利要求4所述的大网络珠粒,其中所述配体单体是N-(4-乙烯基苄基)-N,N,N-三正戊基铵或N-(4-乙烯基苄基)-N-癸基-N,N-二甲基铵。
6.如权利要求4所述的大网络珠粒,其中所述配体单体是N-(4-乙烯基苄基)-N,N,N-三正戊基铵。
7.如权利要求4所述的大网络珠粒,其中所述配体单体是N-(4-乙烯基苄基)-N-癸基-N,N-二甲基铵。
8.如权利要求1或2所述的大网络珠粒,其中所述珠粒的表面积为0.1-500m2/g。
9.一种制备如权利要求1所述的大网络珠粒的方法,其包括使以下物质聚合:
(a)与选自由以下离子组成的组的非金属替代离子络合的阳离子配体单体:连四硫酸根、连六硫酸根,己基二酮酸根、庚基二酮酸根、辛基二酮酸根,1,4-亚苯基二乙酸根,丁烷二磺酸根、戊烷二磺酸根和己烷二磺酸根,
(b)非配体单体,和
(c)交联单体。
10.一种制备如权利要求2所述的大网络珠粒的方法,其包括使以下物质聚合:
(a)与苯-1,3,5-三基-三羧酸的三碱盐络合的阳离子配体单体,
(b)非配体单体,和
(c)交联单体。
12.如权利要求11所述的大网络珠粒,其中所述容量为10-35mg Hg2+/g大网络珠粒。
14.一种从一种或更多种靶标金属离子与其他离子掺混的溶液中选择性地隔绝出所述一种或更多种靶标金属离子的方法,其包括首先使如权利要求1至8或11至12中任一项所述的大网络聚合物珠粒与洗提溶液接触,借此从所述大网络聚合物珠粒中除去所述络合离子,然后使所述经洗提珠粒与所述溶液接触,由此选择性地将所述靶标离子隔绝在所述大网络聚合物珠粒中。
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CN110734079B (zh) * | 2019-11-22 | 2022-04-05 | 安徽工业大学 | 一种锂辉石中锂的提取方法、其提取用吸附材料及制备方法 |
RU2765188C1 (ru) * | 2020-11-03 | 2022-01-26 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Способ получения селективного сорбента для твердофазной экстракции |
CN113509912B (zh) * | 2020-11-25 | 2022-06-10 | 中国科学院青海盐湖研究所 | 一种用于液体锂资源提取的锂离子筛吸附剂颗粒制备方法 |
CN115869898B (zh) * | 2022-07-15 | 2023-06-02 | 中国科学院青海盐湖研究所 | 锂吸附剂、其制备方法及锂离子的提取方法 |
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BR112019009018A2 (pt) | 2019-09-10 |
CN110139708A (zh) | 2019-08-16 |
EP3535054A4 (en) | 2020-12-16 |
MX2019005280A (es) | 2019-09-09 |
EP3535054A1 (en) | 2019-09-11 |
WO2018085626A1 (en) | 2018-05-11 |
MX2024009022A (es) | 2024-08-06 |
AU2017353993A1 (en) | 2019-05-30 |
RU2019115932A3 (zh) | 2020-12-08 |
US20180117564A1 (en) | 2018-05-03 |
RU2019115932A (ru) | 2020-12-03 |
AU2017353993B2 (en) | 2022-07-21 |
PE20190853A1 (es) | 2019-06-18 |
US11389782B2 (en) | 2022-07-19 |
CA3042533A1 (en) | 2018-05-11 |
RU2748350C2 (ru) | 2021-05-24 |
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