基于Ugi多组分反应的海藻酸酰胺衍生物改性二氧化硅纳米粒子的制备

doi:10.7503/cjcu20150831

高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (5): 1018.doi: 10.7503/cjcu20150831

• 高分子化学 • 上一篇

基于Ugi多组分反应的海藻酸酰胺衍生物改性二氧化硅纳米粒子的制备

颜慧琼¹, 陈秀琼¹, 李嘉诚²(), 冯玉红², 伍剑博², 林强¹(), 史载峰¹, 王向辉¹

1. 海南师范大学化学化工学院, 海口 571158
2. 海南大学材料与化工学院, 海口 570228

收稿日期:2015-10-30 出版日期:2016-05-10 发布日期:2016-04-21
作者简介:联系人简介: 林强, 男, 博士, 教授, 博士生导师, 主要从事精细化学品分子设计、化工工艺、有机合成和生物材料方面的研究. E-mail:linqianggroup@163.com
李嘉诚, 男, 博士, 教授, 主要从事胶体界面化学方面的研究. E-mail: ljcfyh@263.net
基金资助:
国家自然科学基金 (批准号: 21366010, 21566009)和海南省重点科技计划项目(批准号: ZDXM2014037)资助

Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction^†

YAN Huiqiong¹, CHEN Xiuqiong¹, LI Jiacheng^2,^*(), FENG Yuhong², WU Jianbo², LIN Qiang^1,^*(), SHI Zaifeng¹, WANG Xianghui¹

1. College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China
2. College of Materials and Chemical Engineering, Hainan University, Haikou 570228, China

Received:2015-10-30 Online:2016-05-10 Published:2016-04-21
Contact: LI Jiacheng,LIN Qiang E-mail:ljcfyh@263.net;linqianggroup@163.com
Supported by:
† Supported by the National Natural Science Foundation of China(Nos.21366010, 21566009) and the Key Projects in the Hainan Provincial Science & Technology Program, China(No.ZDXM2014037)

摘要/Abstract

摘要：

采用海藻酸酰胺衍生物通过Ugi多组分反应制备了新颖的聚合物-二氧化硅(Oct-Alg-SiO₂)纳米粒子. 通过氢核磁共振波谱(¹H NMR)和X射线光电子能谱(XPS)对Oct-Alg-SiO₂的结构和表面元素组分进行了表征. 采用透射电子显微镜(TEM)、 Zeta电位和激光粒度分析仪对Oct-Alg-SiO₂的形貌、粒径和胶体性能进行了探索. 结果表明, 海藻酸酰胺衍生物共价接枝到氨基二氧化硅(SiO₂-NH₂)纳米粒子的表面, 提高了其平均直径, 调控了其Zeta电位, 在水介质中能够表现出良好的分散稳定性. 以10%的液体石蜡为油相, 采用Oct-Alg-SiO₂制备了Pickering乳液. 在油水界面能够形成液滴粒径为5.7 μm的稳定Pickering乳液. 随着水相pH值的增大, 乳液体积分数增大, 稳定性增强. 细胞相容性实验结果表明, Oct-Alg-SiO₂纳米粒子具有极好的生物相容性.

关键词: Ugi多组分反应, 二氧化硅纳米粒子, 两亲性, Pickering乳液, 海藻酸酰胺衍生物

Abstract:

To wider applications of silica(SiO₂) nanoparticles, the Ugi multicomponent reaction was proposed to prepare the novel polymers-silica(Oct-Alg-SiO₂) nanoparticles using amidic alginate derivatives. The structure and surface elemental composition of Oct-Alg-SiO₂ were confirmed by ¹H Nuclear Magnetic Resonance(¹H NMR) spectrometer and X-ray photoelectron spectroscopy(XPS). Additionally, the morpho-logy, size and colloid stability of Oct-Alg-SiO₂ were also investigated via transmission electron microscope(TEM), zeta potential and laser particle size analyzer. The characterization of the materials revealed that Oct-Alg-SiO₂ nanoparticles were successfully fabricated via the Ugi reaction. The amidic alginate derivatives were covalently bonded onto the surface of amino-functionalized silica(SiO₂-NH₂) nanoparticles, increasing their average diameter and tuning their zeta potential, which could exhibit good dispersion stability performance in the aqueous media. The Pickering emulsions were prepared by Oct-Alg-SiO₂ using 10% liquid paraffin as the oil phase. It is worth noting that the stable Pickering emulsions with an average size of 5.7 μm could form between the oil-water interfaces. With the increase of pH value, the volume fraction of the emulsions increased and the stability of the emulsions also improved. The cytocompatibility experimental results showed that Oct-Alg-SiO₂ nanoparticles possessed excellent biocompatibility. Oct-Alg-SiO₂ nanoparticles combined excellent colloid stability performance of SiO₂ nanoparticles and good biological properties of amidic alginate derivatives, possessing great potentials in biomedical applications.

Key words: Ugi multicomponent reaction, Silica nanoparticles, Amphipathic, Pickering emulsions, Amidic alginate derivatives

中图分类号:

TrendMD:

颜慧琼, 陈秀琼, 李嘉诚, 冯玉红, 伍剑博, 林强, 史载峰, 王向辉. 基于Ugi多组分反应的海藻酸酰胺衍生物改性二氧化硅纳米粒子的制备. 高等学校化学学报, 2016, 37(5): 1018.

YAN Huiqiong, CHEN Xiuqiong, LI Jiacheng, FENG Yuhong, WU Jianbo, LIN Qiang, SHI Zaifeng, WANG Xianghui. Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction^†. Chem. J. Chinese Universities, 2016, 37(5): 1018.

图/表 8

Scheme 1 Schematic illustration of the preparation of Oct-Alg-SiO2

Scheme 2 Synthetic routes of Oct-Alg-SiO2

Fig.1 1H NMR spectrum of Oct-Alg-SiO2

Fig.2 XPS spectrum of Oct-Alg-SiO2

Fig.3 TEM image(A), size distribution derived from the TEM image(B), hydrodynamic diameter distribution(C) and zeta potential distribution(D) of Oct-Alg-SiO2

Table 1 Characteristics of silica nanoparticles

Sample	Average diameter^a/nm	Hydrodynamic diameter/nm	PDI^b	Zeta potential/mV
SiO₂	65.1	92.4	0.17	-20.2
SiO₂-NH₂	73.2	159.9	0.26	13.9
Oct-Alg-SiO₂	91.8	215.7	0.31	-31.6

Fig.4 Micrographs of the Pickering emulsions stabilized by Oct-Alg-SiO2(A) Before emulsification; (B, C) 48 h after emulsification; (D) 7 d after emulsification.

Fig.5 Effect of pH value on the zeta potential and volume fraction of the Pickering emulsion

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基于Ugi多组分反应的海藻酸酰胺衍生物改性二氧化硅纳米粒子的制备

Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction^†

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基于Ugi多组分反应的海藻酸酰胺衍生物改性二氧化硅纳米粒子的制备

Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction†

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Synthesis of Amidic Alginate Derivatives Modified Silica Nanoparticles via Ugi Multicomponent Reaction^†