CN113185491A - 凝胶剂修饰的多孔海绵疏水材料及制备方法及用途 - Google Patents
凝胶剂修饰的多孔海绵疏水材料及制备方法及用途 Download PDFInfo
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Abstract
本发明公开了凝胶剂修饰的多孔海绵疏水材料及制备方法及用途,其制备方法为:将缩醛取代的葡萄糖酰胺与甲醇混合,在搅拌下加热至溶解制成缩醛取代的葡萄糖酰胺甲醇溶液,简称溶液一,将海绵浸入溶液一中,8‑12分钟取出干燥,得到凝胶剂修饰的多孔海绵疏水材料。本发明开发了一种简便而经济的浸涂法来制备凝胶剂修饰的多孔海绵疏水材料,工艺简单、成本低廉。实验证明凝胶剂修饰的多孔海绵疏水材料具有良好的吸油性能,能够快速地选择性吸收各种油类和/或有机溶剂,通过简单的挤压即可收集被吸收的物质,凝胶剂修饰的多孔海绵疏水材料可以重复利用,具有出色的可循环性。在油水分离方面有很大的应用价值。
Description
技术领域
本发明属于精细化工技术领域,具体涉及一种凝胶剂修饰的多孔海绵疏水材料及制备方 法及用途。
背景技术
超分子凝胶是由低分子量凝胶因子(分子量小于3000)通过自组装形成的一种介于液体 和固体之间的典型软材料,凝胶因子通过各种非共价相互作用(例如氢键,π-π作用,静电作 用和范德华力)在溶剂中自组装形成纤维状、棒状、带状或球状聚集体,聚集体进一步缠绕 形成三维网状结构,并通过表面张力和毛细作用将溶液束缚于其中。由于非共价键在一定程 度上动态可逆,超分子凝胶相对于聚合物凝胶具有可逆性、刺激响应性、自修复性和一定的 生物相容性等优势(Chem.Soc.Rev.2016,45(15):4226-4251.)。
频繁发生的海洋溢油和有机污染物泄漏事故对海洋生态环境具有持久的严重负面影响, 并且会带来巨大的经济损失。常规的溢油处理方法包括围油栏、原位燃烧、物理吸附和使用 化学分散剂等(Small.2015,11(39):5222-5229)。在这些方法中,使用吸附剂不仅对环境无害, 还能回收油品,被认为是一种更理想的选择。常见的吸附材料有改性粘土、片状石墨和纤维 素材料等,这些材料通常有吸油率低、可回收性差和成本高等缺点,限制了它们的实际应用 (J.Porous Mater.2003,10(3):159-170)。近年来,低密度高孔隙率的多孔海绵在油水分离领 域引起了人们的关注。商业海绵都是两亲性的,为了使海绵在油水分离过程中具有高吸油能 力和良好的疏水性,目前已经开发了许多方法对商业海绵进行表面改性。用SiO2(J Ind Eng Chem.2016,40:47-53),Ag(Chempluschem.2014,79(6):850-856),Fe3O4(Mater.Lett.2017, 190:119-122)等无机纳米颗粒作为表面涂层的方法需要对颗粒进行复杂的预处理,石墨烯 (ACS Appl.Mater.Interfaces.2013,5(20):10018-10026)和碳纳米管(Colloids Surf.A Physicochem.Eng.Asp.2018,551:9-16)等碳材料也常用于海绵的表面改性,但制备工艺繁琐, 成本较高。因此,寻找一种低成本、无污染、制备工艺简单的疏水材料对开发新型高效吸油 材料来说十分有意义。
发明内容
本发明的目的在于克服现有技术的不足,提供一种缩醛取代的葡萄糖酰胺。
本发明的第二个目的是提供一种缩醛取代的葡萄糖酰胺的制备方法。
本发明的第三个目的是提供凝胶剂修饰的多孔海绵疏水材料。
本发明的第四个目的是提供凝胶剂修饰的多孔海绵疏水材料的制备方法。
本发明的第五个目的是提供凝胶剂修饰的多孔海绵疏水材料在吸附油类和有机溶剂的用 途。
本发明的技术方案概述如下:
一种缩醛取代的葡萄糖酰胺,如式I所示:
其中,n=8、10或12。
一种缩醛取代的葡萄糖酰胺的制备方法,包括如下步骤:
缩醛取代的葡萄糖酸甲酯Ⅱ与脂肪族二元胺反应,得到缩醛取代的葡萄糖酰胺,反应式 如下:
其中,n=8、10或12。
一种凝胶剂修饰的多孔海绵疏水材料的制备方法,包括如下步骤:将缩醛取代的葡萄糖 酰胺与甲醇混合,在搅拌下加热至溶解制成浓度为1-10毫克/毫升的缩醛取代的葡萄糖酰胺甲 醇溶液,简称溶液一,将海绵浸入溶液一中,8-12分钟取出干燥,得到凝胶剂修饰的多孔海 绵疏水材料。
所述海绵为三聚氰胺海绵、聚氨酯海绵或聚醚海绵。
上述制备方法制备的凝胶剂修饰的多孔海绵疏水材料。
上述凝胶剂修饰的多孔海绵疏水材料在吸附油类或有机溶剂的用途。
本发明的优点:
本发明使用一种缩醛取代的葡萄糖酰胺(超分子凝胶剂)作为海绵的表面改性材料,开 发了一种简便而经济的浸涂法来制备凝胶剂修饰的多孔海绵疏水材料,工艺简单、成本低廉。 本发明将海绵在热的缩醛取代的葡萄糖酰胺甲醇溶液中浸渍,干燥,实验证明凝胶剂修饰的 多孔海绵疏水材料具有良好的吸油性能,能够快速地选择性吸收各种油类和/或有机溶剂,通 过简单的挤压即可收集被吸收的物质,凝胶剂修饰的多孔海绵疏水材料可以重复利用,具有 出色的可循环性。在油水分离方面有很大的应用价值。
附图说明
图1为一种凝胶剂修饰的多孔海绵疏水材料在空气中的水接触角。其中a为实施例4制 备;b为实施例5制备;c为实施例3制备;
图2为实施例3制备的凝胶剂修饰的多孔海绵疏水材料循环使用过程中的吸附容量变化 图。
具体实施方式
下面结合具体实施例对本发明作进一步的说明。
实施例1
在10℃的水浴条件下,向装有机械搅拌器、温度计的1L四口瓶中加入50wt%的D-葡萄 糖酸水溶液(172.62g)、甲醇(100mL)和浓盐酸(200mL),搅拌10min。将59.04g的3,4-二甲基 苯甲醛溶于200mL甲醇中,将3,4-二甲基苯甲醛的甲醇溶液滴加到四口瓶中,随着反应进行 体系有白色固体析出,持续搅拌24h。反应完毕后向体系中加入100mL水,搅拌2h后抽滤, 滤饼用蒸馏水洗涤至中性,然后滤饼在二氯甲烷中加热回流洗涤三次,烘干得到产品93.71g, 产率为65.3%;熔点为175.3-176.9℃;1H NMR(400MHz,DMSO-d6,TMS,25℃):δ7.31(s,1H,Ar-H),7.23(dd,J=7.7,1.7Hz,1H,Ar-H),7.17(d,J=7.8Hz,1H,Ar-H),5.57(s,1H, OCHO),4.91(d,J=8.3Hz,1H,OH),4.77(d,J=6.0Hz,1H,OH),4.72(d,J=1.8Hz,1H, CH),4.46(t,J=5.8Hz,1H,OH),4.03(d,J=8.2Hz,1H,CH),3.80(m,1H,CH),3.71(m,3H,CH3),3.68(m,1H,CH),3.58(m,1H,CH2),3.42(dt,1H,CH2),2.26(d,J=4.0Hz, 6H,CH3);13C NMR(100MHz,DMSO-d6):δ169.33,137.15,136.06,129.32,128.04,124.45, 100.31,79.35,79.15,69.44,63.54,62.92,52.00,19.82,19.66。得到2,4-(3,4-二甲基苯亚 甲基)-D-葡萄糖酸甲酯(Ⅱ)。
实施例2
缩醛取代的葡萄糖酰胺(Ⅰ-1)的制备方法,包括如下步骤:
向装有磁力搅拌的100mL三口瓶中加入2,4-(3,4-二甲基苯亚甲基)-D-葡萄糖酸甲酯(Ⅱ) 3.27g、甲醇50mL、催化剂4-二甲氨基吡啶0.03g,于40℃下加热搅拌30min后加入十二二 胺6.01g,加热搅拌反应12h。反应结束后将产物抽滤,滤饼用甲醇洗涤抽干得到粗品。将粗 品用甲醇重结晶,烘干得到白色固体3.06g,产率为62%;熔点为;1H NMR(400MHz,MeOD) δ7.39(s,1H),7.31(d,J=7.7Hz,1H),7.15(d,J=7.8Hz,1H),5.65(s,1H),4.88(s,9H),4.45(s, 1H),4.21(s,1H),3.89(s,2H),3.79(d,J=10.8Hz,1H),3.67(d,J=10.5Hz,1H),3.34(dd,J= 9.3,7.8Hz,4H),2.70–2.57(m,2H),2.30(d,J=7.5Hz,6H),1.60–1.41(m,4H),1.31(s,15H). 得到缩醛取代的葡萄糖酰胺Ⅰ-1。
反应式如下:
用辛二胺或癸二胺替代本实施例的十二二胺,其它同本实施例,依次分别得到缩醛取代 的葡萄糖酰胺(I-2)和缩醛取代的葡萄糖酰胺(I-3)。
实施例3
凝胶剂修饰的多孔海绵疏水材料的制备方法,包括如下步骤:将缩醛取代的葡萄糖酰胺 (Ⅰ-1)与甲醇混合,在搅拌下加热至65℃溶解,制成浓度为5mg/mL的缩醛取代的葡萄糖 酰胺(Ⅰ-1)甲醇溶液,简称溶液一,将切成1cm3的三聚氰胺海绵预处理(用丙酮和去离子 水洗涤并干燥),浸入溶液一中,10分钟取出干燥,得到凝胶剂修饰的多孔海绵疏水材料(简 称A12)。
实施例4
凝胶剂修饰的多孔海绵疏水材料的制备方法,包括如下步骤:将缩醛取代的葡萄糖酰胺 (Ⅰ-2)与甲醇混合,在搅拌下加热至50℃溶解,制成浓度为1mg/mL的缩醛取代的葡萄糖 酰胺(Ⅰ-2)甲醇溶液,简称溶液一,将切成1cm3的三聚氰胺海绵预处理(用丙酮和去离子 水洗涤并干燥),浸入溶液一中,12分钟取出干燥,得到凝胶剂修饰的多孔海绵疏水材料(简 称A8)。
实施例5
凝胶剂修饰的多孔海绵疏水材料的制备方法,包括如下步骤:将缩醛取代的葡萄糖酰胺 (Ⅰ-3)与甲醇混合,在搅拌下加热至80℃溶解制成浓度为10mg/mL的缩醛取代的葡萄糖酰 胺(Ⅰ-3)甲醇溶液,简称溶液一,将切成1cm3的三聚氰胺海绵预处理(用丙酮和去离子水 洗涤并干燥),浸入溶液一中,8分钟取出干燥,得到凝胶剂修饰的多孔海绵疏水材料简称 (A10)。
用聚氨酯海绵或聚醚海绵替代本实施例的三聚氰胺海绵,其它同本实施例,制备出相应 的凝胶剂修饰的多孔海绵疏水材料。
实施例6
凝胶剂修饰的多孔海绵疏水材料的油水分离性能测试如下:
(1)疏水性:使用JC2000D1接触角测量仪(中国上海POWEREACH)在室温下测量凝胶剂修饰的多孔海绵疏水材料的水接触角。
普通海绵在空气中的水接触角为0°。
A8的水接触角为128.3°(图1a);
A10的水接触角为127.9°(图1b);
A12的水接触角为129°(图1c)。
凝胶剂修饰的多孔海绵疏水材料具有良好的疏水性,不会吸收水。
其中,Q为饱和吸附能力,g/g;m为凝胶剂修饰的多孔海绵疏水材料吸附后的质量,g; m0为凝胶剂修饰的多孔海绵疏水材料吸附前的质量,g。测试结果如表1所示,凝胶剂修饰 的多孔海绵疏水材料具有出色的吸附性能。
表1凝胶剂修饰的多孔海绵疏水材料对不同有机溶剂和油品的吸附能力
(3)循环使用性能:以A12为例,表现出优异的重复使用性能,在50次吸附-挤压循环之后, 其吸附容量保持率在90%以上(图2)。
Claims (6)
3.一种凝胶剂修饰的多孔海绵疏水材料的制备方法,其特征是包括如下步骤:将权利要求1的缩醛取代的葡萄糖酰胺与甲醇混合,在搅拌下加热至溶解制成浓度为1-10毫克/毫升的缩醛取代的葡萄糖酰胺甲醇溶液,简称溶液一,将海绵浸入溶液一中,8-12分钟取出干燥,得到凝胶剂修饰的多孔海绵疏水材料。
4.根据权利要求3所述的制备方法,其特征在于所述海绵为三聚氰胺海绵、聚氨酯海绵或聚醚海绵。
5.权利要求3或4的制备方法制备的凝胶剂修饰的多孔海绵疏水材料。
6.权利要求5的凝胶剂修饰的多孔海绵疏水材料在吸附油类或有机溶剂的用途。
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