以不同结构的氨基酸、醛、叔丁基异腈为单体,以无水甲醇为溶剂,在室温条件下通过Ugi反应制备出一系列聚酰胺.利用FTIR、1H NMR、13C NMR和GPC等技术系统地表征了聚酰胺的结构,考查了单体投料比、单体浓度、反应时间以及不同结构氨基酸和醛等因素对聚合反应的影响.结果表明,在Ugi反应中,随着聚合时间的延长,聚酰胺的收率逐渐增加,而摩尔质量变化不明显.当氨基酸、醛和叔丁基异腈的投料比(物质的量比)为1∶1.1∶1.1时,聚酰胺的收率较高,摩尔质量最大;同时,5-氨基戊酸和6-氨基己酸分别与异丁醛、叔丁基异腈组成聚合体系时,聚酰胺的摩尔质量分别达到2.02×104 和1.96×104 g/mol,且收率均超过93.0%.总之,Ugi聚合反应为不同结构与性能聚酰胺材料的制备提供了一种便捷高效的合成方法.
In this work, a series of polyamides were successfully synthesized at room temperature via Ugi reaction, using amino acids, aldehyde and t-butylisocyanide as monomers in methanol.The structures of the polyamide were characterized by FTIR, 1H NMR, 13C NMR and GPC.The effects of monomer feed ratio, monomer concentration, reaction time and different amino acids and aldehydes on the polymerization were investigated.It was found that the yield of polyamide increases gradually with the polymerization time, while the molecular weight did not change significantly.When the molar ratio of amino acids, aldehyde and t-butylisocyanide is equal to 1∶1.1∶1.1, the yield of polyamides and its molecular weight were the largest.When 5-aminovaleric acid and 6-aminocaproic acid were polymerized with isobutylaldehyde and t-butylisocyanide, respectively, the molecular weights of polyamides were 2.02×104 and 1.96×104 g/mol, their yields are 93%.In conclusion, Ugi reaction provides a convenient and efficient synthetic strategy for the preparation of polyamides with different structures and properties.- DOI:10.3969/j.issn.1000-1565.2019.04.007基于Ugi反应聚酰胺的制备张朋飞1,2,刘娜1,赵荣慧1,3,张琪1,秦斐1,邓奎林1(1.河北大学 化学与环境科学学院临床药学办公室,河北 保定 071002;2.保定学院 生物化工与环境工程学院,河北 保定 071000;3.河北大学附属医院 临床药学办公室,河北 保定 071000)摘 要:以不同结构的氨基酸、醛、叔丁基异腈为单体,以无水甲醇为溶剂,在室温条件下通过Ugi反应制备出一系列聚酰胺.利用FTIR、1H NMR、13C NMR和GPC等技术系统地表征了聚酰胺的结构,考查了单体投料比、单体浓度、反应时间以及不同结构氨基酸和醛等因素对聚合反应的影响.结果表明,在Ugi反应中,随着聚合时间的延长,聚酰胺的收率逐渐增加,而摩尔质量变化不明显.当氨基酸、醛和叔丁基异腈的投料比(物质的量比)为1∶1.1∶1.1时,聚酰胺的收率较高,摩尔质量最大;同时,5-氨基戊酸和6-氨基己酸分别与异丁醛、叔丁基异腈组成聚合体系时,聚酰胺的摩尔质量分别达到2.02×104 和1.96×104 g/mol,且收率均超过93.0%.总之,Ugi聚合反应为不同结构与性能聚酰胺材料的制备提供了一种便捷高效的合成方法.关键词:Ugi反应;氨基酸;聚酰胺中图分类号:O633.2 文献标志码:A 文章编号:1000-1565(2019)04-0372-07Preparation of polyamides based on Ugi reactionZHANG Pengfei1,2, LIU Na1, ZHAO Ronghui1, ZHANG Qi1, QIN Fei1, DENG Kuilin1(1.College of Chemistry & Environmental Science, Hebei University,Baoding 071002, China; 2.College of Biochemical Engineering& Environmental Engineering, Baoding University, Baoding 071000, China;3.Clinical Pharmacy Office, Affiliated Hospital of Hebei University, Baoding 071000,China)Abstract: In this work, a series of polyamides were successfully synthesized at room temperature via Ugi reaction, using amino acids, aldehyde and t-butylisocyanide as monomers in methanol.The structures of the polyamide were characterized by FTIR, 1H NMR, 13C NMR and GPC.The effects of monomer feed ratio, monomer concentration, reaction time and different amino acids and aldehydes on the polymerization were investigated.It was found that the yield of polyamide increases gradually with the polymerization time, while the molecular weight did not change significantly.When the molar ratio of amino acids, aldehyde and t-butylisocyanide is equal to 1∶1.1∶1.1, the yield of polyamides and its molecular weight were the largest.When 5-aminovaleric acid and 6-aminocaproic acid were polymerized with isobutylaldehyde and t-butylisocyanide, respectively, the molecular weights of polyamides were 2.02×104 and 1.96×104 g/mol, their yields are 93%.In conclusion, Ugi reaction provides a convenient and efficient synthetic strategy for the preparation of polyamides with different structures and properties.- 收稿日期:2018-10-18 基金项目:河北大学大学生创新创业训练计划项目(201810075090);河北省重点研发计划自筹项目(18211241) 第一作者:张朋飞(1984—),男,河北保定人,保定学院讲师,河北大学在读博士研究生,主要从事智能聚合物的设计、制备及性能研究.E-mail:zhangpengfei-1984@163.com 通信作者:邓奎林(1968—),男,河北遵化人,河北大学教授,主要从事智能聚合物的设计、制备及性能研究. E-mail:dengkl_hbu@163.com第4期张朋飞等:基于Ugi反应聚酰胺的制备
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