Synthesis,micellization and cytotoxic studies of ester-functionalized imidazolium gemini surfactants

The fatty acid-based imidazolium gemini surfactants containing hydroxy-substituted spacers were synthesized and characterized by different spectral techniques. The micellization behavior of product compounds was studied by determining their critical micelle concentration (cmc) values from steady state fluorescence and conductivity measurements. The thermodynamic parameters of micellization of synthesized gemini surfactants confirmed that the micelle formation is a thermodynamically favorable, endothermic and an entropy driven phenomenon. The surfactants were further analyzed for their cytotoxic nature by treating them upon human embryonic kidney cell (HEK-293) line and were found to be significantly low cytotoxic. The interesting features like low cmc values, non-cytotoxic and eco-friendly nature of the gemini surfactants may offer new and more efficient substitutes to the conventional drug delivery systems. Thus the gemini surfactants may serve as promising candidates in the biomedical and pharmaceutical fields.     

双子表面活性剂的综述

双子表面活性剂是一类新型的表面活性剂,它是由联结基团通过化学键将两个或多个单体表面活性剂连接在一起形成的表面活性剂。由于其优异的性质越来越受到国内外学者的重视。与传统表面活性剂相比较,双子表面活性剂在降低表面张力、聚集生成胶团、Krafft点和临界胶束浓度(CMC)等性能上都明显更加的优异。文章就它的性能和应用等方面进行介绍。     

季铵盐型gemini表面活性剂的合成及性能研究

以N,N-二甲基十二烷基叔胺与2,2′-二氯乙醚为原料,合成了季铵盐型gemini表面活性剂QAGS;采用IR和元素分析对合成产物进行了结构表征;研究了反应时间、溶剂类型及用量以及反应物物质的量比对产率的影响;并考察了QAGS的表面活性。结果表明:当N,N-二甲基十二烷基叔胺和2,2′-二氯乙醚的物质的量比为3.0∶1、反应介质为乙腈、乙腈用量为45mL、反应时间为72h时,QAGS的产率最高达22.76%;QAGS水溶液的表面张力随其浓度的增大而急剧减小,浓度达到1.054mmol·L-1时,表面张力基本不变;QAGS的饱和吸附量为1.597×10-6 mol·m-2,分子截面积为1.04nm2。     

The Effects of the Organic Groups Attached at the Silicone Atoms of the Organosilane-Based Gemini Nonionic Surfactants on Their Surface Activities

A novel trisiloxane gemini nonionic surfactant was synthesized by the reaction of 3-(diethoxy(methyl)silyl)propan-1-amine with hexamethyldisiloxane to get 3-(trisiloxane)propan-1-amine, which was further reacted with glutaroyl dichloride to form the surfactant molecule, N ¹,N ⁵-bis(3-(trisiloxane)propyl)glutaramide (3). Some related compounds were also prepared, including N ¹,N ⁵-bis (3-(trimethoxysilyl)propyl) glutaramide (1), and N ¹,N ⁵-bis(3-(diethoxy(methyl)silyl)propyl)glutaramide (2). All prepared compounds were analyzed by IR, ¹H-NMR and ¹³C-NMR to confirm their structures. Their interfacial activities, including surface tension and wetting ability, were measured. These surface activities were compared each other and a discussion was carried out on how the organic groups attached on the silicone atoms affect their surface tension and wetting ability. To explain the superior surface activities of the molecules 3, a hypothesis was proposed about a cyclic hydrophobic core area that could be formed by the two hydrophobic chains and the linker of the gemini molecule due to the dispersion force (Van der Waals force) between the two trisiloxane moieties, which close the hydrophobic cycle inside the molecule.     

二氯-双(N,N-二甲基-N-十四烷基)-2-羟基-1,3-丙二铵的合成与性能研究

以十四烷基胺、1,3-二氯丙醇合成标题化合物.采用正交实验,研究了物料比、反应时间、反应温度对合成的影响,并对产品的一些理化性质进行评定.结果表明:合成双十四烷基季铵盐的最佳工艺条件为:以丙酮为溶剂,N,N-二甲基十四烷基叔胺与1,3-二氯丙醇的物料比为2.2∶1,反应温度为60 ℃,反应时间为20 h.DBHD在25 ℃下的表面张力为36.7 mN/m,临界胶束浓度(CMC)为9.5×10~(-4) mol/L和DTAB的相比具有较低的CMC;当DBHD浓度为80 mg/L对异氧菌的杀菌时间为4 h时达到最大值为96%,当杀菌时间为48 h时杀菌率还保持85%,杀菌性能明显优于传统杀菌剂1227;DBHD在50 ℃的5% H_2SO_4+0.1 mol/L NaCl溶液中投加量为100 mg/L对A3钢片的缓蚀率达82%,所合成的DBHD是一种高效的酸洗缓蚀剂.     

以阳离子Gemini表面活性剂为模板合成介孔氧化硅

以阳离子Gemini表面活性剂——双十六烷基三甲基溴化铵[C16H33N+(CH3)2(CH2)2N+(CH3)2C16H33].2Br-(G16-2-16)为模板剂,正硅酸乙酯为硅源,在n(SiO2)∶n(G16-2-16)∶n(NH3)∶n(H2O)=1∶0.1∶9∶110的条件下,在弱碱性环境中用水热法合成了平均孔径3.1 nm、比表面积906.71 m2/g、孔容0.93 cm3/g、具有二维六角结构且高度有序的介孔氧化硅MCM-41。采用小角XRD、高分辨透射电镜(HRTEM)、N2吸附-脱附分析和热重-微分热重法(TG-DTG)对其结构进行了考察,分析了不同模板剂浓度对材料结构有序度的影响。结果表明,n(G16-2-16)/n(TEOS)=0.1时,合成的材料有序度最高。     

一种环境友好型水基多功能油污清洗剂的研制

以新型阴离子双生表面活性剂、可生物降解非离子表面活性剂、无磷助洗剂、复合缓蚀剂、杀菌剂等复配制成弱碱性水基多功能油污清洗剂.通过正交试验及对产品多种性能的检测,确定了清洗剂的配方.试验结果表明,该清洗剂稳定性好,室温下5min去油污能力可达100%,能有效地清洗物体表面的油污,对金属的腐蚀率几乎为零,并有良好的杀菌性能,不含ODS物质,对环境友好.     

VES自转向盐酸液变粘特性研究

实验研究了未指名孪二连型粘弹性表面活性剂(VES)自转向盐酸液的变粘特性。5%VES HCl CaCl2模拟酸液的粘度在pH值高于-0.57后迅速上升,pH值1~2时有最大值,这与前人的实验结果略有不同。将2%~6%VES 1%HCl 18.25?Cl2模拟酸液的pH值调至~2,得到的凝胶粘度随VES浓度增大而增大,随温度升高(25~70℃)经历不同的极大值(30~50℃)。5%VES 20%HCl酸液与CaCO3完全反应、pH升至4~5时,形成的凝胶粘度也随温度升高而经历极大值(67℃),但在30~40℃区间粘度急剧波动。G′和G″的频率关系曲线表明0.1%HCl 5%VES 18.25?Cl2模拟酸液的弹性和粘性均大于含0.01%和1.0%HCl的模拟酸液。pH值改变(0.17~13.0)不会使6%VES溶液增粘;加入56~219 g/L CaCl2不会使20%HCl 6%VES酸液增粘;加入3.4mol/L Na 并调pH值至中性或加入2.3 mol/L Ca2 并调pH值至弱酸性,使0.1%HCl 5%VES酸液粘度增大至78~80 mPa.s;因此同时加大pH值和阳离子(Ca2 或Na )浓度,才能使VES酸液增粘。图7表2参10。     

一种阴离子型双子表面活性剂的合成与表征

以乙二胺、2-溴乙基磺酸钠、月桂酸等为主要原料制备了阴离子型双子(gemini)表面活性剂N,N′-乙撑双[(N-乙磺酸钠)-十二酰胺](DTM-12),以IR和1HNMR对其结构进行了表征。该目标产物水溶液的cmc(5.0×10-4mol/L)是十二烷基磺酸钠和十二烷基硫酸钠的1/20和1/16,γcmc(29.7 mN/m)比它们低8 mN/m~10 mN/m。DTM-12分别与DTAB和Triton X-100组成的复配体系在摩尔比为3∶7时,cmc达到1.06×10-4mol/L和0.49×10-4mol/L,γcmc达到25.4 mN/m和31.7 mN/m,DTM-12表现出较好的协同效应。DTM-12还具有良好的润湿力。     

离子液体双子咪唑表面活性剂的合成

为了提高传统表面活性剂在溶液中的表面活性,合成了以亚甲基链为联接基团、具有对称结构的系列双子咪唑离子液体型表面活性剂.对目标产物结构进行核磁共振氢谱表征.测定了25℃下双子咪唑离子液体表面活性剂水溶液的表面张力.结果表明:合成的系列双子咪唑表面活性剂均为目标产物;在联接基团长度一定的情况下,疏水基团碳原子数增加,分子在空气/水界面吸附的趋势增大,其临界胶束浓度和吸附量逐渐减小,吸附面积和pc20逐渐增大,而表面张力受疏水链长影响较小,表现出较高的表面活性;此外,在疏水基团链长一定的情况下,联接基团长度较短的双子咪唑表面活性剂具有较高的降低表面张力的效率和能力,更容易在空气/水界面发生吸附.