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化学进展 2020, Vol. 32 Issue (2/3): 147-161 DOI: 10.7536/PC190804   后一篇

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基于铜催化叠氮-炔环加成反应的聚氨酯功能化

章强1, 黄文峻1, 王延斌1, 李兴建1,**(), 张宜恒2   

  1. 1. 临沂大学材料科学与工程学院　临沂 276000
    2. 青岛科技大学化学与分子工程学院　青岛 266042
  • 收稿日期:2019-08-05 出版日期:2020-02-15 发布日期:2019-12-19
  • 通讯作者: 李兴建
  • 基金资助:
    国家自然科学基金项目(21176128); 国家自然科学基金项目(51172116)
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Functionalization of Polyurethane Based on Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction

Qiang Zhang1, Wenjun Huang1, Yanbin Wang1, Xingjian Li1,**(), Yiheng Zhang2   

  1. 1. School of Materials Science and Engineering, Linyi University, Linyi 276000, China
    2. School of Chemical and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
  • Received:2019-08-05 Online:2020-02-15 Published:2019-12-19
  • Contact: Xingjian Li
  • About author:
    ** e-mail:
  • Supported by:
    National Natural Science Foundation of China(21176128); National Natural Science Foundation of China(51172116)

聚氨酯(PU)作为一种重要的工业材料,具有诸多独特优异的性能,这使得PU材料在众多领域内具有极其广泛的应用。由于PU骨架上缺乏进一步修饰的功能基团,限制了PU材料的高附加值化,在高科技领域广泛应用受到阻碍。因此,PU的改性和功能化是学术界和工业界热门的课题之一。当前PU材料的改性和功能化方法较多,其中,叠氮化物与末端炔在铜(Ⅰ) 催化下生成反式1, 2, 3-三唑化合物的Huisgen 1, 3-偶极环加成(CuAAC)反应具有操作简单方便和灵活高效的特点,是点击化学反应的精髓,在PU材料的功能化改性研究中占有独特而重要的地位。本文简要介绍了基于CuAAC反应PU材料功能化改性的设计思路,重点综述了基于CuAAC反应,PU材料的生物相容性、疏水性、荧光性、抗菌性、阻燃性、形状记忆效应、机械性能和热稳定性的功能化改性研究和应用,最后总结了CuAAC反应在改性PU上存在的主要问题,并对其研究方向进行了展望。

关键词： 聚氨酯, 点击化学, 铜(Ⅰ)催化叠氮-炔环加成反应, 功能化

As an important industrial material, polyurethane(PU) has many unique and excellent properties, which makes PU materials possess a wide range of applications in many fields. Due to the lack of further modified functional groups on the PU backbone, the high value-addition of PU materials is limited, and its widespread application in high-tech fields is hindered. Therefore, the modification and functionalization of PU is one of the hot topics in academia and industry. At present, there are many methods for modification and functionalization of PU materials. Among them, the Cu(Ⅰ) catalyzed Huisgen 1, 3-dipolar cycloaddition(CuAAC) between an azide and an alkyne compound forming trans 1, 2, 3-triazole compounds, which is the essence of click chemistry reaction, has the characteristics of simple operation, flexibility and high efficiency. It plays a unique and important role in the functional modification research of PU materials. This paper briefly introduces the design idea of functional modification of PU materials based on CuAAC reaction. The functional modification research and application of biocompatibility, hydrophobicity, fluorescence, antibacteria, flame retardancy, shape memory effect, mechanical properties and thermal stability of PU materials based on CuAAC reaction are highlighted. Finally, the main problems of the modified PU via CuAAC reaction are summarized, and the research direction is prospected.

Key words: polyurethane, click chemistry, Cu(I) catalyzed azide-alkyne cycloaddition;, functionalization
()
图1 (a)点击化学反应模型;(b)Cu(Ⅰ)催化的叠氮-炔环加成机理
Fig.1 (a) The model of click reaction. (b) Mechanism for Cu(Ⅰ) catalyzed azide-alkyne cycloaddition
图2 炔基和叠氮基功能化PU的合成策略
Fig.2 Synthesis strategy of alkynyl and azido functionalized polyurethanes
图3 在铜催化下炔基功能化WPU和Rf-N3之间的CuAAC反应[40]
Fig.3 The copper catalyzed CuAAC reaction between the alkyne-functionalized WPU and Rf- N 3 [ 40 ]
图4 (a)叠氮基功能化PU纳米囊和炔基荧光颜料之间的表面点击化学反应;(b) 炔基荧光颜料的分子结构;(c)经过点击反应后的纳米微囊扫描电镜图[44]
Fig.4 (a)Surface click chemistry reaction between azide-functionalized PU nanocapsules and alkyne fluorescent dye. (b) The molecular structure of alkyne fluorescent dye.(c)SEM image of nanocapsules made after the reactions[44]
图5 (a)PTFM的合成示意图;(b)蓖麻油基PU泡沫的实验室规模燃烧测试;(c)PU三唑泡沫的实验室规模燃烧测试[55]
Fig.5 (a) Schematic representation of the synthesis of PTFM. (b) Lab-scale flame test of castor polyol based polyurethane foams. (c) Lab-scale flame test of polyurethane triazole foams[55]
图6 (a)叠氮基官能化GO片合成的示意图;(b)和(c)基于CuAAC反应制备的PU/GO纳米复合材料的热响应和光响应形状回复图[71]
Fig.6 (a)Schematic representation of the synthesis of the azide-functionalized GO sheets. (b) and (c) images of thermo-responsive and photo-responsive shape recovery of the PU/GO nanocomposites using CuAAC[71]
图7 富含三唑的超支化多元醇不同代数的合成路线[79]
Fig.7 Synthetic route for different generations of triazole-rich hyperbranched polyols[79]
图8 (a)叠氮基和炔基功能化WPU的CuAAC点击交联; (b)可点击WPU的微粒相互扩散和成膜机制[83]
Fig.8 (a) A typical CuAAC click cross-linking of WPU functionalized by azide and alkyne. (b) Microparticle interdiffusion and film-forming mechanism of clickable WPU[83]
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