羧酸甜菜碱酯的合成及其水解条件优化.docVIP

  羧酸甜菜碱酯的合成及其水解条件优化# 史素青，张琴，马泽环，赵洋，宫永宽* （合成与天然功能分子化学教育部重点实验室,西北大学化学与材料科学学院,西安 710069） 5 10 摘要：合成了末端酯键可水解型羧酸甜菜碱酯甲基丙烯酸酯单体 (CBMA-1C2)，并研究了 CBMA-1C2 在不同条件下的水解情况，用 1H NMR 计算羧酸甜菜碱酯酯键的水解率。结果 发现，当 NaOH 水溶液浓度为 0.2 mol/L、水解时间为 1 h、水解温度为 37 时，羧酸甜菜 碱酯酯键的水解率可高达 88~95%，且不会破坏甲基丙烯酸酯酯键。其它条件不变，当氨水 浓度为 0.1 mol/L、0.2 mol/L、0.3 mol/L 和 0.4 mol/L 时, 羧酸甜菜碱酯酯键的水解率依次为 6%、43%、56%和~100%，呈现较强的浓度依赖性，这为后续设计水解可控结构切换聚合物 刷表面，构建同时具有抗粘附和杀菌功能的功能性涂层提供了契机。 关键词：羧酸甜菜碱酯; 水解; 优化; 碱液 中图分类号：O631 15 Synthesis and hydrolysis optimization of hydrolysable carboxybetaine ester methacrylate SHI Suqing, ZHANG Qin, MA Zehuan, ZHAO Yang, GONG Yongkuan (Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, 20 25 30 35 40 College of Chemistry Materials Science, Northwest University, Xian 710069, China) Abstract: A hydrolysable cationic carboxybetaine ester (CBMA-1C2) is synthesized and used to optimize its hydrolysis process. The 1H NMR is used to calculate the degree of hydrolysis (DH) for terminal carboxybetain ester bond. The results show that when the concentration of sodium hydroxide , the hydrolysis time and hydrolysis temperature is 0.2mol/L, 1h and 37 ℃ , respectively, DH of terminal carboxybetaine ester bond can reach 88~95% and the ester bond of methalcrylate does not be affected. If the CBMA-1C2 is hydrolyzed in ammonium water, the good relationship between DH of terminal carboxybetaine ester and concentration of ammonium water can be obtained, which provides the new possibilities for design and fabricate the hydrolysis controllable polymer brushes with antebacterial and antifouling properties simultaneously. Key words: carboxybetaine ester; hydrolysis; optimization; alkaline solution 0 引言 两性离子物质是指结构中同时含有正（阳）离子和负（阴）离子的物质，这类物质因能 形成高度水化层而显示出良好的生物相容性，常用的两性离子物质主要包括磷酰胆碱（PC）、 羧基甜菜碱甲基丙烯酸酯（CBMA）、硫代甜菜碱甲基丙烯酸酯（SBMA）及其聚合物等[1-5]。 近年来,羧酸甜菜碱酯因其末端酯键可水解的特性备受关注[6-10]。美国江绍毅课题组利用羧 酸甜菜碱酯甲基丙烯酸酯（CBMA-1C2）等对材料表面进行化学修饰，所得表面在碱性溶液中 水解后可形成两性离子结构，具有良好的生物相容性和抗污能力[7-10]。 虽然 CBMA-1C2 中羧酸甜菜碱酯酯键