含萘酰亚胺和烷基疏水基的新型表面活性剂合成及性能  

Synthesis and properties of novel surfactants containing naphthalimide and alkyl segments

作　　者：邢环宇 贾丽华[1] 赵振龙 杨瑞[1] 郭祥峰[1,2] Huanyu Xing;Lihua Jia;Zhenlong Zhao;Rui Yang;Xiangfeng Guo(College of Chemistry and Chemical Engineering,Qiqihar University,Qiqihar,Heilongjiang 161006,China;College of Chemistry,Guangdong Institute of Petrochemical Technology,Maoming,Guangdong 525000,China)

机构地区：[1]齐齐哈尔大学化学与化学工程学院,黑龙江齐齐哈尔161006 [2]广东石油化工学院化学学院,广东茂名525000

出　　处：《日用化学工业（中英文）》2023年第7期742-747,共6页China Surfactant Detergent & Cosmetics

基　　金：国家自然科学基金(21176125);黑龙江省属本科高校基本科研业务费(145109102)。

摘　　要：为获得高效多功能表面活性剂,设计并合成了一系列萘酰亚胺和长链烷基为疏水基的新型季铵盐阳离子表面活性剂(C_(n)NDA,n=10,12,14,16代表长链烷基链长),并利用红外光谱(FT-IR)、核磁氢谱(^(1)H NMR)、核磁碳谱(^(13)C NMR)和质谱(HRMS)对其结构进行了表征。研究了C_(n)NDA的表面活性、胶束性质、泡沫及抗菌性能。结果表明,C_(n)NDA具有优异的表面活性和泡沫性能。当疏水烷基链长碳数从10增加到16,其cmc值从1.01降至0.026 mmol/L;0.10 g/L的C14NDA水溶液的泡沫半衰期可达16 h。同时C_(n)NDA具有良好的抗菌活性,C_(16)NDA对大肠杆菌和金黄色葡萄球菌的最低杀菌质量浓度分别为3.0和1.2μg/mL。另外,^(1)H NMR和荧光光谱研究表明,C_(n)NDA能够形成分子间氢键,且萘酰亚胺基团间形成了π-π堆积。C_(n)NDA的优异性能与上述分子间的相互作用密切相关。该类表面活性剂在杀菌和泡沫等领域具有潜在的应用前景。A series of novel cationic quaternary ammonium surfactants(C_(n)NDA,n=10,12,14 and 16)were designed and synthesized,whose structure had both naphthalimide and long hydrocarbon chain as hydrophobic moieties.Their structures were characterized by FT-IR,^(1)H NMR,^(13)C NMR and ESI-MS,and all the synthesized compounds were target products.The surface activity,micellization behavior,foaming ability,foam stability and antibacterial properties were tested.The results showed that,C_(n)NDA showed excellent surface activity and foaming properties.When the carbon number of hydrocarbon chain was increased from 10 to16,the cmc decreased from 1.01 to 0.026 mmol/L;the foam volume of 10 mL aqueous solution of 0.10 g/L C14NDA was 28 mL at 0 min and 26.5 mL at 5 min,and the half-life was 16 h.In addition,C_(n)NDA showed excellent antibacterial activities against E.coli and S.aureus,and the minimum bactericidal mass concentrations for C_(16)NDA were 3.0 and 1.2μg/mL,respectively.The results of ^(1)H NMR of C12NDA in DMSO-d6 revealed that,the chemical shift of amide proton shifted to the low field by 0.13 with the concentration increased from 3.0 mmol/L to 9.0 mmol/L,indicative of the formation of hydrogen bond by the amido groups.From the fluorescence spectra of different concentrations of C_(16)NDA,it could be found that the fluorescence intensity was decreased and the emission peak was red-shifted by 2 nm when the concentration exceeded cmc,indicative of theπ-πstacking between naphthalimide segments.The excellent properties of C_(n)NDA were mainly attributed to the hydrophobic interactions from naphthalimide segments and long alkyl chains,π-πstacking of the adjacent naphthalimide segments,hydrogen bonding of amides groups,and electrostatic interactions.Therefore,they might have potential applications in foam and bactericidal fields.

关 键 词：新型表面活性剂 萘酰亚胺 表面活性 泡沫 抗菌 

分 类 号：TQ423[化学工程]