Page 85 - 201811

第 35 卷第 11 期 精 细 化 工 Vol.35, No.11
2018 年 11 月 FINE CHEMICALS Nov. 2018

功能材料
基于双分子亲核取代反应海藻酸苄酯

衍生物的制备与性能

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冯美西 1,2 ，陈秀琼 ，林良泉 ，胡继森 ，颜慧琼 1,2* ，林 强 1,2*
（1. 海南师范大学 热带药用植物化学教育部重点实验室，海南 海口 571158；2. 海南省水环境污染治理
与资源化重点实验室，海南 海口 571158）

摘要：以溴化苄(BnBr)为疏水改性剂，采用双分子亲核取代反应（SN2）制备了海藻酸苄酯衍生物（BAD）。通
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过 FTIR、 HNMR、TGA、UV-Vis、GPC、DLS 和 Zeta 电位分析表征了 BAD 的结构和性能。结果表明：所得
产物取代度接近于溴化苄与糖醛酸的投料比，说明 SN2 反应活性高、取代度大。改性后，BAD 相对分子质量（M w ）
由 91544 降低至 79819。在水热驱动作用下 BAD 形成的胶束聚集体水动力学粒径（d H ）为 423.4 nm，Zeta 电位
值为36.4 mV。并且随 pH 的增大，其 Zeta 电位有不断降低的趋势，而 d H 先升高后降低。随离子强度的增大，
d H 和 Zeta 电位都出现先升高后降低的趋势，因此，BAD 有一定的胶体界面活性。
关键词：双分子亲核取代反应；海藻酸苄酯衍生物；取代度；胶体界面活性；功能材料
中图分类号：TQ 453.292 文献标识码：A 文章编号：1003-5214 (2018) 11-1871-07

Preparation and Performances of a Benzyl Alginate Derivative via a
Bimolecular Nucleophilic Substitution Reaction

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FENG Mei-xi , CHEN Xiu-qiong , LIN Liang-quan , HU Ji-sen ,
YAN Hui-qiong 1,2* , LIN Qiang 1,2*
（1. Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou
571158, Hainan, China; 2. Key Laboratory of Water Pollution Treatment and Resource Reuse of Hainan Province, Haikou
571158, Hainan, China）
Abstract: Benzyl alginate derivative (BAD) was prepared by a bimolecular nucleophilic substitution
reaction (SN2) using benzyl bromide (BnBr) as hydrophobic modifier. Its structure and performances were
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characterized by FTIR, HNMR, TGA, UV-Vis, GPC, DLS and Zeta potential. Experimental results showed
that the degree of substitution of the obtained product was close to the molar ratio of benzyl bromide to
uronic acid, indicating that the activity of SN2 reaction was high and the degree of substitution of BAD was
large. After modification, the molecular weight (M w) of BAD decreased from 91544 to 79819. BAD could
form micellar aggregates under hydrothermal driving forces. The hydrodynamic diameter (d H) and Zeta
potential value of BAD micelles were 423.4 nm and 36.4 mV, respectively. Furthermore, with the increase
of pH, the Zeta potential tended to decrease, while the d H initially increased and then decreased. Meanwhile,
when the ionic strength increased, both d H and Zeta potential showed a tendency to increase first and then
decrease. Therefore, BAD exhibited certain colloidal and interfacial activity.
Key words: bimolecular nucleophilic substitution reaction; benzyl alginate derivative; degree of
substitution; colloidal and interfacial activity; functional materials
Foundation items: Natural Science Foundation of Hainan Province (218QN233); National Natural Science
Foundation of China (21566009)

收稿日期：2018-03-23; 定用日期：2018-05-22; DOI: 10.13550/j.jxhg.20180207
基金项目：海南省自然科学基金项目（218QN233）；国家自然科学基金项目（21566009）
作者简介：冯美西（1991—），女，硕士研究生。联系人：颜慧琼（1986—），讲师，博士，E-mail：yanhqedu@163.com；林 强（1962—），
教授，博士生导师，电话：0898-65884995，E-mail：linqianggroup@163.com。