CN1175268A - 与重氮盐反应的碳材料 - Google Patents

与重氮盐反应的碳材料 Download PDF

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CN1175268A
CN1175268A CN95197591A CN95197591A CN1175268A CN 1175268 A CN1175268 A CN 1175268A CN 95197591 A CN95197591 A CN 95197591A CN 95197591 A CN95197591 A CN 95197591A CN 1175268 A CN1175268 A CN 1175268A
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詹姆斯·A·贝尔蒙特
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Abstract

制备具有机基团的碳产品的方法,该有机基团连到碳材料上。该碳材料选自石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品。在一个方法中,在没有足以还原重氮盐的外加电流下,至少一种重氮盐与碳材料反应。在另一个方法中,在质子性反应介质中至少一种重氮盐与碳材料反应。

Description

与重氮盐反应 的碳材料
本发明涉及碳产品的制备方法。该方法涉及重氮盐与碳材料反应，生成具有连到该碳材料上的有机基团的碳产品。该碳材料选自石墨粉、石墨材料、碳纤维、碳织物、玻璃碳产品和活性碳产品。
碳材料用于各种工业和产品中。这些碳材料包括：例如，石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品，这些碳材料的许多用途讨论如下。
石墨粉，除了它在铅笔中用作“铅”外，还用于许多领域中，包括电子、化学、冶金和火箭元件。由石墨制成的电极用于炼钢炉和电解制备氯、氯酸盐、镁和钠中。石墨也用来制备冶金模具、坩锅和化学反应容器。在火箭领域，石墨用作火箭电动机喷嘴和导弹鼻锥。
石墨纤维和碳纤维类似地用于各种领域中。短或碎的纤维经常用作注塑件及汽车刹车(这些地方需要良好的耐磨性能)中的增强剂。高性能石墨或碳纤维用于结构复合材料，特别是那些航空领域用的复合材料。这些纤维也广泛地用于运动商品，如鱼杆、高尔夫球棍和网球球拍。
碳织物或毯片是由碳或石墨的长纤维制备的简单织物。它们可用于如下这些领域：地毯或涉及计算机的家俱中的静电损耗、电磁屏蔽和片料成型汽车部件的静电印刷。这种低热传导性也可用于火箭元件领域。
玻璃碳用于电子产品如电极和机械产品(如坩锅)的制备。
活性碳具有优良的吸附性，因此用来改进制得的化学品、油和脂肪的颜色，控制水、饮料和食品的颜色、气味和味道。这些气体吸附碳也用于气体分离操作、溶剂蒸气的回收、空调系统和气体护罩。
在过去几十年里已作过许多努力来改变碳材料的表面化学。当有可能把已吸附的材料物理地沉积到碳材料表面上时，永久改变其表面化学实际上是更困难了。
PCT专利申请WO 92/13983介绍了一种由重氮盐电化学还原来对含碳材料表面进行改性的方法。据报道，该方法可用于，特别是复合材料的碳板和碳纤维。也介绍了由这种方法改性的含碳材料。在Delmar等人的“美国化学家协会”(J.Am.Chem.Soc.)1992，114，5883-5884，也介绍了电化学还原含官能化芳基的重氮盐来用共价键改性碳表面。
根据WO 92/13983，对含碳材料表面改性的方法包括通过电化学还原含有一个芳族基团的重氮盐来把这个芳基接枝到这种材料的表面上。把这种含碳材料在非质子传递溶剂中与重氮盐接触，并相对于也与该重氮盐溶液接触的阳极使其带负电荷。报道使用质子性溶剂使该电化学方法不能生成所要的产物，结果还原了重氮三键，生成了肼。
尽管有上面所讨论的工艺，仍需要改性炭黑的表面化学并赋予炭黑所需要的性能。
因此，本发明涉及制备含有一个有机基团的碳产品的方法，该有机基团连到选自下列的碳材料上：石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品。连接到该炭黑上。一个方法包括在没有足以还原该重氮盐的外加电流条件下至少一个重氮盐与碳材料反应的步骤。
另外一个方法包括在质子反应介质中至少一种重氮盐与碳材料反应。
下面的说明书介绍了本发明另外一些特征和优点。这些作用通过该说明书介绍更明显，或通过所述的本发明的实施可理解这些作用。通过特别是在下面说明书中和所附的权利要求书中指出的方法、产品和组合物，将理解和实现本发明的目的和其他优点。制备炭黑产品的方法
本发明的第一个实施方案提供了制备含有一个有机基团的碳产品的方法，该有机基团连到该碳材料上。该碳材料选自石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品。
一个方法包括在没有足以还原重氮盐的外加电流下至少一种重氮盐与碳材料反应。即，在重氮盐和碳材料之间的反应是在没有足以还原该重氮盐的外部电子源的条件下进行的。不同重氮盐的混合物可用于本发明的这种方法中。可在各种反应条件下、在任何类型的反应介质中(包括质子和非质子传递溶剂体系或淤浆)进行该方法。
在另外一种方法中，在质子反应介质中至少一种重氮盐与碳材料反应。可在本发明的这种方法中使用不同重氮盐的混合物。也可在各种反应条件下进行该方法。
优选，在两个方法中，现场形成该重氮盐。如果需要的话，在任何一个方法中，可用本领域已知的方法分离和干燥该碳产品。另外，可用已知工艺处理该生成的碳产品来除去杂质。这些方法的优选实施方案讨论如下并于实施例中。
用于本发明方法的碳材料是选自石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品的碳材料。该生成的炭黑产品可用于未处理碳材料的已知用途中。更重要的是，可用本发明的方法来制备未处理碳材料所没有的优良性能的碳产品。
可在各种条件下进行该发明的方法，并通常不局限于任何具体的条件。反应条件一定是这样的，使得该具体的重氮盐足够稳定以让它与碳材料反应。因此，可在重氮盐是短时间存在的反应条件下进行这些方法。重氮盐和碳材料之间的反应，例如在很宽的pH范围和温度范围内进行。可在酸性、中性和碱性pH下进行这些方法。优选该pH在约1-9间变化。该反应温度优选在0℃-100℃范围内。本领域中已知的重氮盐可通过例如伯胺和亚硝酸水溶液的反应来制备。重氮盐和其制备方法的一般性讨论见Morrison和Boyd的“有机化学”(Organic Chemistry)，第五版，第937-983页，(Allyn andBacon，Inc.1987)，和March的“高等有机化学：反应、机理和结构”(AdvancedOrganic Chemistry：Reactions，Mechanisms and Structures)，第四版，(Wiley，1992)。根据本发明，重氮盐是具有一个或多个重氮基团的有机化合物。
在本发明的方法中，该重氮盐可在与碳材料反应之前制得，或更优选使用本领域的已知工艺现场制得。“现场”制备也允许使用不稳定的重氮盐如烷基重氮盐，并避免了对该重氮盐进行不必要的处理或操作。在本发明特别优选的方法中，亚硝酸和重氮盐两个都是现场制备的。
本领域中已知的重氮盐，可通过伯胺、亚硝酸盐和酸反应来制备。该亚硝酸盐可以是任何亚硝酸金属盐，优选是亚硝酸锂、亚销酸钠、亚硝酸钾或亚硝酸锌，或任何有机的亚硝酸酯，如亚硝酸异戊酯或亚硝酸乙酯。该酸可以是在生成该重氮盐中有效的任何无机的或有机的酸。优选的酸包括硝酸HNO3、氢氯酸HCl和硫酸H2SO4。
该重氮盐也可以通过伯胺与二氧化氮水溶液反应来制备。该二氧化氮的水溶液NO2/H2O，提供了生成该重氮盐所需的亚硝酸。
在过量HCl存在下生成重氮盐相比于其他方法来说是不太优选的，因为HCl对不锈钢腐蚀。用NO2/H2O来生成重氮盐具有对通常用于反应容器的不锈钢或其他金属腐蚀性较小的附加优点。用H2SO4/NaNO2或HNO3/NaNO2制备的腐蚀性也相对小一些。
一般来说，从伯胺、亚硝酸盐和酸生成重氮盐需要基于所用的胺两当量的酸。在一个“现场”法中，可用一当量酸来生成该重氮盐。当该伯胺含有一个强酸基时，在本发明的方法中没必要加入另外的酸。伯胺的一个酸基或多个酸基可提供一个或两个所需的酸的等价物。当该伯胺含有一个强酸基团时，优选向本发明的方法不加入另外的酸或加入最高达一个当量的其他酸，来现场生成该重氮盐。可使用稍稍过量的其他酸。这种伯胺的一个例子是对-氨基苯磺酸(磺胺酸)。
一般地，重氮盐是热不稳定的。它们通常是在低温(如0-5℃)溶液中制备的并在盐不分离的情况下使用。加热一些重氮盐的溶液可放出氮气并在酸性介质中形成相应的醇或在碱性介质中形成有机自由基。
然而，为了实施本发明的方法，该重氮盐仅需要足够稳定来与碳材料反应就行。因此，本发明的方法可用一些在其他情况下认为是不稳定并易于分解的重氮盐来进行。一些分解过程可与该碳材料和重氮盐之间的反应竞争，并可减少连接到该碳材料上的有机基团的总数。另外，该反应可在较高的温度下进行，这时许多重氮盐易于分解。较高的温度也可有利地增加该重氮盐在反应介质中的溶解性并提高在其该方法中的加工性。然而，由于其他的分解过程，较高的温度可导致一些重氮盐的损失。
本发明方法可通过向在反应介质(如水)中的碳材料的混合物或悬浮液中加入反应剂现场形成重氮盐来实施。因此，在本发明的方法中待使用的混合物或悬浮液可已经包括一种或多种反应剂来形成重氮盐，且通过加入其余的反应剂就可实施本发明的方法。
在有机化合物中常见的大量官能团适合于形成重氮盐的反应。因此，仅有与碳材料反应的重氮盐的可获得性限制了本发明的方法。
本发明的方法可在任何允许重氮盐与碳材料之间进行反应的反应介质中进行。优选，该反应介质是基于溶剂的体系。该溶剂可以是质子性溶剂、非质子传递溶剂、或溶剂的混合物。质子性溶剂是如水或甲醇的溶剂，含有连接到氧原子或氮原子的氢原子，并因此有足够的酸性形成氢键。非质子传递溶剂是不含有酸性氢原子的溶剂。非质子传递溶剂包括：例如，如己烷、四氢呋喃(THF)、乙腈和苄腈的溶剂。对质子和非质子溶剂的讨论，参见Morrison和Boyd的“有机化学”(Organic Chemistry)，第五版，第228-231页(Allyn and Bacon，Inc.1987)。
本发明的方法优选在一种质子性反应介质中进行，即在单独一种质子性溶剂中或含有至少一种质子性溶剂的溶剂混合物中进行。优选的质子性介质包括，但不局限于：水、含有水和其他溶剂的水性介质、醇、和含有醇的任何介质或这些介质的混合物。
一般来说，本发明的方法产生了无机副产物，如盐。在一些目标用途中，如下面讨论的那些用途，这些副产物可能是不希望有的且是成问题的。根据本发明的方法，一些制备碳产品而又没有不想要的无机副产物或盐的可行方法如下：
首先，用本领域中的已知手段在使用前除去不希望要的无机副产物，来纯化该重氮盐。第二，用有机亚硝酸酯作为产生相应醇的重氮化试剂，而不是用无机盐，来生成该重氮盐。第三，当从具有酸基的胺和水性NO2生成重氮盐时，没有形成无机盐。其他一些方法对本领域的熟练技术人员是熟知的。
除了生成无机副产物外，本发明的方法也可产生有机副产物。这些有机副产物可通过用有机溶剂萃取除去。其他方法对于本领域熟练技术人员是熟知的。碳产品
本发明方法中的重氮盐与碳材料之间的反应形成了具有一个有机基团的碳产品，该有机基团连接到选自石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品的碳材料上。该重氮盐可含有待连接到炭黑上的有机基团。该有机基团可以是脂族基、环状有机基、或具有脂族部分和环状部分的有机化合物。如上所述，本发明方法中所使用的重氮盐可以从这样一种伯胺来制备，该伯胺具有一个这样的基团并能形成(甚至非稳定地形成)，一种重氮盐。该有机基可以是取代或非取代的、支化或非支化的。脂族基包括：例如，从烷烃、链烯烃、醇类、醚类、醛类、酮类、羧酸类和糖类衍生的基。环状有机基团包括，但不局限于：脂环烃基(如环烷基、环烯基)、杂环烃基(如吡咯烷基、吡咯啉基、哌啶基、吗啉基等)、芳基(如苯基、萘基、蒽基等)、和杂芳基(如咪唑基、吡唑基、吡啶基、噻吩基、噻唑基、呋喃基、吲哚基等)。当取代的有机基团的空间位阻增加时，从该重氮盐与碳材料反应连接到该碳材料上的有机基团的数目可能减少。
当该有机基团被取代时，它可含有任何适宜于重氮盐形成的官能团。优选的官能团包括、但不局限于：OR、COR、COOR、OCOR、COONa、COOK、COO-NR4 +、卤素、CN、NR2、Sn、SO3H、SO3Na、SO3K、SO3 -NR4 +、NR(COR)、CONR2、NO2、PO3H2、PO3HNa、PO3Na2、N＝NR、NR3 +X-和PR3 +X-。R独立地是氢原子、C1-C20烷基(支化或未支化的)或芳基。整数n在1-8内变化，并优选在2-4间变化。阴离子X-是卤化物或从矿物酸或有机酸衍生的阴离子。
优选的有机基团是式AyAr-的芳族基，其相当于式AyArNH2的伯胺。在该式中，变量的意思如下：Ar是芳族基，选自苯基、萘基、蒽基、菲基、二苯基、吡啶基；A是芳族基上的取代基，独立选自上述优选官能团，或A是线性、支化或环状的烃基(优选含有高达1-20个碳原子)、未取代或用一个或多个那些官能团取代；且当Ar是苯基时，y是1-5的整数，当Ar是萘基时，y是1-7的整数，当Ar是蒽基时、菲基或二苯基时，y是1-9的整数，或当Ar是吡啶基时，y是1-4的整数。
另外一组可连接到该碳材料上的有机基团是被作为官能团的一个离子或可离子化基团所取代的有机基团。可离子化基团在所使用的介质能形成离子基团。该离子基团可以是阴离子基团或阳离子基团，该可离子化的基团可形成阴离子或阳离子。
形成阴离子的可离子化官能团包括：例如，酸基或酸基的盐。因此，该有机基团包括从有机酸衍生的基团。优选当它含有一个形成阴离子的可离子化基团时，这样的一个有机基团具有a)一个芳族基团，和b)至少一个具有pKa小于11的酸基，或至少一个具有pKa小于11的酸基的盐，或至少一个具有pKa小于11的酸基和至少一个具有pKa小于11的酸基的盐的混合物。该酸基的pKa是指整个有机基团的pKa，而不只是该酸基取代基的。更优选，该pKa小于10，且最优选小于9。优选该有机基团的芳族基直接连到该炭黑上。该芳族基可进一步被取代或未取代，如用烷基。更优选，该有机基团是苯基或萘基，且该酸基是磺酸基、亚磺酸基、膦酸基或羧酸基。这些酸基和它们的盐的例子介绍如上。最优选，该有机基团是取代的或未取代的磺苯基或其盐；取代的或未取代的(多磺基)苯基或其盐；取代的或未取代的磺萘基或其盐；取代的或未取代的(多磺基)萘基或其盐。优选取代的磺苯基是羟基磺苯基或其盐。
具体的具有形成阴离子(和在本发明方法中使用的相应的伯胺)的可离子化官能团的有机基团是：对-磺苯基(对-磺胺酸)、4-羟基-3-磺苯基(2-羟基-5-氨基-苯磺酸)和2-磺乙基(2-氨基乙磺酸)。
胺表示形成阳离子基团的可离子化官能团的例子。例如，胺在酸性介质中可质子化形成铵基。优选，具有胺基取代基的有机基团的pKb小于5。季铵基(-NR3 +)和季磷鎓基(-PR3 +)也表示阳离子基团的例子。优选，该有机基团含有一个如苯基或萘基的芳基和一个季铵基或一个季磷鎓基。该芳基优选直接连到炭黑上。季环状胺、甚至季芳香胺，也可用作该有机基团。因此，N-取代的吡啶鎓化合物，如N-甲基-吡啶基，可用在这方面。
具有用离子或可离子化基团取代的连有有机基团的碳材料的一个优点是：相对于相应的未处理碳材料，该碳产品可提高水分散性。除了其水分散性外，具有被离子或可离子化基团取代的有机基团的碳产品，也可分散在极性有机溶剂中，如二甲基亚砜(DMSO)和甲酰胺中。
碳产品的水分散性随着连接到碳材料上具有可离子化基团上的有机基团的数目的增加而增加，或随着连接到指定有机基团上的可离子化基团的数目的增加而增加。因此，增加连到该碳产品上的可离子化基团的数目应提高其水分散性。应注意：通过酸化水性介质，也可提高含有胺作为连接到该碳材料上的有机基团的碳产品的水分散性。由于该碳产品的水分散性在某种程度上取决于电荷的稳定性，所以优选该水性介质的离子强度小于0.1摩尔浓度。更优选，该离子强度小于0.01摩尔浓度。
当由本发明的方法制备这样一种水分散性碳产品时，优选在该反应介质中离子化该离子或可离子化的基团。另外，该碳产品可用常规碳材料所用的工艺进行干燥。然而，过度干燥可引起水分散性程度的损失。
芳族硫化物是另外一组优选的有机基团。具有芳族硫化物基团的碳产品特别适宜于橡胶组合物或其它具有反应性烯属基团的组合物。这些芳族硫化物可由式ArSnAr′或ArSnAr″表示，其中Ar和Ar′独立地是亚芳基，Ar″是芳基，k是1-8。优选的亚芳基包括亚苯基，特别是对-亚苯基。优选的芳基包括苯基和萘基。存在的硫原子数，由n表示的，优选在2-4范围内。特别优选的芳族硫代物基团是双-对-(C6H4)-S2-(C6H4)-和对-(C6H4)-S2-(C6H5)。这些芳族硫化物基团的重氮盐可从其相应的伯胺H 2 N-Ar-Sn-Ar′-NH2或H2N-Ar-Sx-Ar″常规制备。碳产品的用途
本发明的碳产品可用于与相应的未处理碳材料相同的用途。然而，连到该碳材料上的有机基团可用来改变和提高用于特殊用途的给定碳材料的性能。也可选择有机基团来连到指定碳材料所用的基材上。这种连接可采取通过这样一种方法与基质反应的形式来进行，这种方法如硫化、中和、配合或聚合。一个例子是具有NH2基的碳材料用于基于环氧树脂的材料。
下面实施例是用来说明，但不限制本发明。
用S.J.Gregg，K.S.W Sing在“吸附、表面积和孔隙度”(Absorption，SurfaceArea and Porosity)(学术出版社，1982)所述的方法，来测定表面积和孔隙容量。根据第90-97所述的方法测定活性碳的表面积、非孔隙表面积和孔隙容量。根据第84-86页所述的方法用阶梯状等温线来测定碳织物的表面积。通过BET法用氪测定石墨纤维的表面积。
                         实施例1
                     石墨粉产品的制备
该实施例介绍了用本发明方法制备石墨粉产品。把表面积为11.5m2/g的石墨粉样品2.0g搅拌入14g水中。加入0.11g六氟磷酸4-氯重氮苯在7g水中的溶液，放出大量汽泡。搅拌20分钟后，把该产品过滤收集、用四氢呋喃(THF)进行Soxhlet萃取过夜、并在烘箱中干燥。产品分析表明：与未处理石墨粉含有23ppm氯相比较，它含有597ppm氯。因此，该产品每平方纳米表面积含有0.85氯苯基。ESCA(化学分析用电子能谱法)分析表明该产品含有1.4原子百分数氯。用ESCA在未反应石墨粉的表面上未检测到氯。
                        实施例2
                    石墨粉产品的制备
该实施例介绍了用本发明方法制备石墨粉产品。把0.095g四氟硼酸4-硝基重氮苯在10g水中的溶液加到2.0g实施例1的石墨粉在10g水中的搅拌悬浮液中。搅拌15分钟后，该产品在烘箱中125℃下干燥、用四氢呋喃进行Soxhlet萃取过夜并干燥。ESCA分析表明：在406.1eV处有一个N1s信号，在400.5eV处有一个信号，相对面积为5.9∶1。该406.1eV信号是由NO2基引起的，400.5eV信号可能是偶氮基团引起的。没有发现对应于重氮基的403eV处的信号。合并的氮含量为4.0原子百分数。用ESCA在未反应石墨粉上未检测到氮。这表明硝基苯基连到石墨粉产品上。
                      实施例3
                  石墨粉产品的制备
该实施例介绍了用本发明方法制备石墨粉产品。如下制备对-NH3C6H4N2Cl2溶液：把0.028gNaNO2在3g水中的冷溶液加到0.16ml浓HCl、0.043g对-苯二胺和5g水(在冰浴中搅拌)的溶液中。把该冷的重氮物溶液加到2.0g实施例1的石墨粉和18g在室温下搅拌的水的悬浮液中。搅拌1小时后，该产品在烘箱中125℃下干燥，用THF进行Soxhlet萃取过夜、并且干燥。该产物的ESCA分析表明氮的浓度为4.6原子百分数。由ESCA在未反应的石墨粉上未检测到任何氮。这表明氨基苯基连到该石墨粉产品上。
                         实施例4
                    石墨纤维产品的制备
该实施例介绍用本发明方法制备石墨纤维产品。在氮气氛中165℃下干燥表面积为0.43m2/g、直径为8微米的石墨纤维两小时。把该纤维放置在0.1M无水苄腈中的四氟硼酸硝基重氮苯溶液中2分钟。把该纤维取出，用无水苄腈漂洗两次，用THF进行Soxhlet萃取过夜，并在烘箱中干燥。ESCA分析表明：在406.5eV处有N1s信号，在400.5eV处有一信号，相对面积为4.1∶1。该406.5eV信号是由NO2基引起的，400.5eV信号是由原始样品中的氮和偶氮基团引起的。在对应于重氮基的403eV处没有发现信号。合并的氮含量为2.4原子百分数。使用0.01M四氟硼酸硝基重氮苯溶液，用同样方法制得样品的ESCA分析表明有0.9原子百分量的氮。未反应纤维的ESCA分析表明有0.2原子百分量的氮。这表明这两种纤维产品已连有硝基苯基。
                          实施例5
                      碳纤维产品的制备
该实施例介绍了用本发明方法制备石墨纤维产品。把0.095g四氟硼酸4-硝基重氮苯在10g水中的溶液加到2.0g实施例4的石墨纤维在100g水中的搅拌悬浮液中。搅拌15分钟后，把该纤维从该溶液中取出，在烘箱中125℃下干燥，用四氢呋喃进行Soxhlet萃取过夜并干燥。ESCA分析表明：在406.7eV处有一个N1s信号，在400.5eV处有一个信号，相对面积约1∶1。该406.7eV信号是由NO2基引起的，400.5eV信号是由原始样品中的氮和偶氮基团引起的。对应于重氮基的403eV处没有发现信号。与未反应纤维上为0.2原子百分数相比较，合并的氮含量为1.0原子百分数。这表明硝基苯基连到石墨纤维产品上。
                       实施例6
                  石墨纤维产品的制备
该实施例介绍了用本发明方法制备石墨纤维产品。如下制备对-NH3C6H4N2Cl2溶液：把0.028g NaNO2在3g水中的冷溶液加到0.16ml浓HCl、0.043g对-苯二胺和5g水(在冰浴中搅拌)的溶液中。把该冷的重氮物溶液加到2.0g实施例4的石墨纤维和100g在室温下搅拌的水的悬浮液中。搅拌20分钟后，把该产品从溶液中取出，在烘箱中125℃下干燥，用THF进行Soxhlet萃取过夜且干燥。ESCA分析表明：与在未反应纤维上有0.2原子百分数氮相比较，该产物的氮的浓度为1.7原子百分数。这表明氨基苯基连到该石墨纤维产品上。
                         实施例7
                    石墨纤维产品的制备
该实施例介绍用本发明方法制备石墨纤维产品。如下制备硝酸4-氯苯基重氮物的溶液：把0.014g NaNO2在3g水中的溶液加到0.025g 4-氯苯胺、0.070g 90％硝酸和3g水的搅拌溶液中。搅拌10分钟后，把该重氮物溶液加到1g实施例4的石墨纤维和50g水的搅拌混合物中。搅拌30分钟后，从该溶液中取出该纤维，把该纤维在烘箱中110℃下干燥，用THF进行Soxhlet萃取过夜、并干燥。ESCA分析表明该产物的氯的浓度为0.4原子百分数。由ESCA在未反应的石墨纤维上未检测到氯。这且明氯苯基连到了该石墨纤维产品上。
                         实施例8
                    石墨纤维产品的制备
该实施例介绍了用本发明的方法制备石墨纤维产品。把约0.2g实施例4的石墨纤维加到0.025g 4-氯苯胺、0.07g 90％硝酸和70g水的搅拌溶液中。加入0.014g NaNO2在2g水中的溶液，并把该混合物搅拌30分钟。现场生成硝酸4-氯重氮苯，该重氮物与石墨纤维反应。从该溶液中取出该纤维，把该纤维在烘箱中110℃下干燥，用THF进行Soxhlet萃取过夜、并且干燥。该产物的ESCA分析表明氯的浓度为0.4原子百分数。用ESCA在未反应的石墨纤维上未检测到氯。这表明氯苯基连到了该石墨纤维产品上。
                        实施例9
                    碳织物产品的制备
该实施例介绍了用本发明的方法制备碳织物产品。用实施例1的方法把表面积为5.3m2/g的碳织物与六氟磷酸重氮氯苯反应。已用THF进行Soxhlet萃取过夜并干燥的这种材料样品，用ESCA分析，与未反应碳织物含有0.03原子百分数的氯相比较，该产物含有0.4原子百分数的氯。这表明氯苯基连到该碳织物产品上。
                        实施例10
                    玻璃碳产品的制备
该实施例介绍了用本发明的方法制备玻璃碳产品。把一小片玻璃碳板(约0.5g)搅拌入0.047g四氟硼酸4-硝基重氮苯在30g水中的溶液中30分钟。取出该玻璃碳板、干燥、用THF进行Soxhlet萃取过夜且干燥。ESCA分析表明：与未反应的玻璃碳板有0.6原子百分数的氮相比较，该产物的氮的浓度为2.4原子百分数。这表明硝基苯基连到该玻璃碳产品上。
                      实施例11
                  活性碳产品的制备
该实施例介绍用本发明的方法制备活性碳产品。用实施例1的方法，让氮气BET表面积为762m2/g、无孔表面积为266m2/g、孔隙容量为0.20ml/g的活性碳与六氟磷酸重氮氯苯反应。与未反应碳含有0.02％氯相比较，已用THF进行了Soxhlet萃取过夜并干燥的该材料样品含有0.43％氯。因此，该活性碳产品含有0.12mmol/g氯苯基，或每平方纳米含有0.09个氯苯基。这表明氯苯基连到该活性碳产品上。
                        实施例12
                    活性碳产品的制备
该实施例介绍使用本发明方法制备活性碳产品。把1.66g四氟硼酸4-硝基重氮苯在100g水中的溶液加到7g实施例11的活性碳和70g水的搅拌悬浮液中。放出汽泡。搅拌15分钟后，该混合物在烘箱中125℃下干燥。该产物用THF进行Soxhlet萃取过夜并干燥。ESCA分析表明在406.1eV处有一个N1s信号，在400.9eV处有一个信号，相对面积为3.2∶1。该406.1eV处的信号是由NO2基引起的，400.9eV处的信号是由初始样品中的氮和偶氮基团引起的。与未反应活性碳有0.3原子百分数相比较，合并的氮的含量为5.6原子百分数。这表明硝基苯基连到该活性碳产品上。
                      实施例13
                   制备活性碳产品
该实施例介绍了用本发明方法制备活性碳产品。如下制备对-NH3C6H4N2Cl2：把0.483g NaNO2在10g水中的溶液加到2.87ml浓HCl、0.758g对-苯二胺和30g在冰浴中搅拌的水的溶液中。把该冷的重氮物溶液加到7.0g实施例11的活性碳和63g在室温下搅拌的水中的悬浮液中。搅拌15分钟后，该产品在125℃下干燥1小时，用THF进行Soxhlet萃取过夜、并干燥。ESCA分析表明：与未反应活性碳的0.3原子百分数的氮相比较，该产物的氮的浓度为3.5原子百分数。这表明氨基苯基连到该活性碳产品上。

Claims (19)

1.一种制备具有有机基团碳产品的方法，该有机基团连到碳材料上，该方法包括步骤：
在没有足以还原重氮盐的外加电流条件下，至少一种重氮盐与选自下列的碳材料反应：石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品。
2.权利要求1的方法，其中该反应步骤是在非质子介质中进行的。
3.权利要求1的方法，其中该反应步骤是在质子介质中进行的。
4.权利要求1的方法，其中该重氮盐是现场制备的。
5.一种制备具有有机基团的碳产品的方法，该有机基团连到碳材料上，该方法包括步骤：
在质子反应介质中，至少一种重氮盐与选自下列的碳材料反应：石墨粉、石墨纤维、碳纤维、碳织物、玻璃碳产品和活性碳产品。
6.权利要求5的方法，其中该重氮盐是从伯胺现场制备的。
7.权利要求6的方法，其中该重氮盐是由伯胺、亚硝酸盐和酸反应现场制备的。
8.权利要求7的方法，其中该亚硝酸盐是亚硝酸金属盐，并使用一当量的酸。
9.权利要求6的方法，其中该重氮盐是由该伯胺与亚硝酸盐反应现场制备的，且该伯胺含有一个强酸基。
10.权利要求6的方法，其中该重氮盐是由该伯胺与二氧化氮的水溶液反应现场制备的。
11.权利要求6的方法，其中该质子介质是水性介质，且该伯胺是式AyArNH2的胺，其中：
Ar是选自下列的芳基：苯基、萘基、蒽基、菲基、二苯基和吡啶基；
A独立地是一个选自下列的芳基上的取代基：
一个选自下列的官能团：OR、COR、COOR、OCOR、COONa、COOK、COO-NR4 +、卤素、CN、NR2、Sn、SO3H、SO3Na、SO3K、SO3 -NR4 +、NR(COR)、CONR2、NO2、PO3H2、PO3HNa、PO3Na2、N＝NR、N2 +X-、NR3 +X-和PR3 +X；和
一个线性的、支化的或环状的烃基，未取代或用一个或多个所说的官能团所取代；
R独立地是氢、C1-20烷基或芳基；
n是1-8的整数；
X-是卤化物或从矿物酸或有机酸衍生的阴离子；和
y是下列的整数：当Ar是苯基时为1-5，当Ar是萘基时为1-7，当Ar是蒽基、菲基或二苯基时为1-9，或当Ar是吡啶基时为1-4。
12.权利要求5的方法，其中该重氮盐是现场制备的。
13.权利要求5的方法，其中该重氮盐是由独立于该反应步骤从伯胺制备的。
14.权利要求5的方法，其中该质子反应介质是水性介质。
15.权利要求5的方法，其中该重氮盐的有机基是取代或未取代的，并选自脂族基、环状有机基、或具有脂族部分和环状部分的有机化合物。
16.权利要求5的方法，其中该质子反应介质是水。
17.权利要求5的方法，其中该质子反应介质是基于醇的介质。
18.一种根据权利要求1的方法制备的碳产品。
19.一种根据权利要求5的方法制备的碳产品。
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CN101027367B (zh) * 2004-03-15 2012-05-02 卡伯特公司 改性碳产品及其应用
CN102259848A (zh) * 2010-05-26 2011-11-30 东丽纤维研究所（中国）有限公司 一种具有导电性能的纳米石墨片及其制备方法
CN102259848B (zh) * 2010-05-26 2014-08-20 东丽纤维研究所（中国）有限公司 一种具有导电性能的纳米石墨片及其制备方法
CN102491322A (zh) * 2011-12-12 2012-06-13 福建农林大学 表面固定有机官能团的活性炭的制备方法
CN108793138A (zh) * 2017-04-26 2018-11-13 中国科学院理化技术研究所 一种功能化石墨烯浆料的制备方法

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