糖基双子阳离子表面活性剂的合成及其性能研究
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摘要
以葡萄糖为原料,制备了十六烷基葡萄糖酯丁二醇季铵盐双子表面活性剂(7a)、十六烷基葡萄糖酯己二醇季铵盐双子表面活性剂(7b)和十六烷基葡萄糖酯辛二醇季铵盐双子表面活性剂(7c),并对三种表面活性剂的表面活性和聚集性能进行了检测。结果表明:这三种表面活性剂均具有良好的表面活性,其中7c的cmc=1.32×10~(-5)mol/L,γ_(cmc)=29.14mN/m。连接基长度对双子表面活性剂的cmc有较大影响,随着连接基长度逐渐增加,cmc显著降低。而且,这类表面活性剂在水中均能自发形成胶束或囊泡,主要和连接基长度有关。连接基越长,则越容易形成囊泡;胶束和囊泡的形成与表面活性剂的浓度也存在一定的关系,浓度越高,越容易形成囊泡。
Three quaternary ammonium gemini surfactants based on glucose ester structure(7a, 7b and 7c)were prepared with glucose as one of the raw materials, in which the hydrophobic tails were all hexadecyl but the lengths of the methylene chains residing in the centre of the spacers were 4, 6 and 8 CH_2 units, respectively. The surface activity and aggregation properties of these three gemini surfactants were determined. The results show that these three surfactants have good surface activities, among which 7c has the best surface properties(cmc =1.32×10~(-5) mol/L, γ_(cmc) = 29.14 mN/m). The length of the methylene chain in the spacer of a gemini surfactant has a great influence on the cmc, that is, the cmc is significantly decreased with the increase of the methylene chain length. Moreover, these surfactants can spontaneously form micelles or vesicles in water, which is mainly related to the length of the spacer. The longer the spacer is, the easier vesicles will be formed. The formation of micelles and vesicles also has a certain relationship with the concentration of the surfactant. The formation of vesicles will be facilitated at higher concentrations of surfactants.
Three quaternary ammonium gemini surfactants based on glucose ester structure(7a, 7b and 7c)were prepared with glucose as one of the raw materials, in which the hydrophobic tails were all hexadecyl but the lengths of the methylene chains residing in the centre of the spacers were 4, 6 and 8 CH_2 units, respectively. The surface activity and aggregation properties of these three gemini surfactants were determined. The results show that these three surfactants have good surface activities, among which 7c has the best surface properties(cmc =1.32×10~(-5) mol/L, γ_(cmc) = 29.14 mN/m). The length of the methylene chain in the spacer of a gemini surfactant has a great influence on the cmc, that is, the cmc is significantly decreased with the increase of the methylene chain length. Moreover, these surfactants can spontaneously form micelles or vesicles in water, which is mainly related to the length of the spacer. The longer the spacer is, the easier vesicles will be formed. The formation of micelles and vesicles also has a certain relationship with the concentration of the surfactant. The formation of vesicles will be facilitated at higher concentrations of surfactants.
引文
[1]Hill K,Rhode O.Sugar-based surfactants for consumer products and technical applications[J].European Journal of Lipid Science&Technology,1999,101(1):25-33.
[2]Zana R,Xia J.Gemini surfactants:synthesis,interfacial and solutionphase behavior,and applications[J].Journal of Colloid&Interface Science,2003,272(2):502.
[3]Zana R,Talmon Y.Dependence of aggregate morphology on structure of dimeric surfactants[J].Nature,1993,362(6417):228-230.
[4]Zana R.Dimeric and oligomeric surfactants.Behavior at interfaces and in aqueous solution:a review[J].Advances in Colloid&Interface Science,2002,97(1):205-253.
[5]Kang P,Xu H J,Song C L.Properties of binary surfactant system of alkyl polyglycosides and alpha-sulphonated fatty acid methyl ester[J].Tenside Surfactants Detergents,2013,50(3):192-198.
[6]Han Z,Yang X,Yong L,et al.Physicochemical properties and phase behavior of didecyldimethylammonium chloride/alkyl polyglycoside surfactant mixtures[J].Journal of Surfactants&Detergents,2015,18(4):641-649.
[7]Warwel S,Brüse F,Schier H.Glucamine-based gemini surfactants I:Gemini surfactants from long-chain-alkyl glucamines andα,ω-diepoxides[J].Journal of Surfactants&Detergents,2004,7(2):181-186.
[8]Fielden M L,Perrin C,Kremer A,et al.Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro[J].Febs Journal,2010,268(5):1269-1279.
[9]Wilk K A,Syper L,Domagalska B W,et a1.Aldonamide-type gemini surfactants:synthesis,structural analysis,and biological properties[J].Journal of Surfactants and Detergents,2002,5(3):235-244.
[10]Yoshimura T,Umezawa S,Fujino A,et al.Equilibrium surface tension,dynamic surface tension,and micellization properties of lactobionamide-type sugar-based gemini surfactants[J].Journal of Oleo Science,2013,62(6):353-362.
[11]Liu S,Sang R,Hong S,et al.A novel type of highly effective nonionic gemini alkyl O-glucoside surfactants:a versatile strategy of design[J].Langmuir,2013,29(27):8511-8516.
[12]Wang G,Zhang D,Du Z,et al.Spontaneous vesicle formation from trisiloxane-tailed gemini surfactant[J].Journal of Industrial and Engineering Chemistry,2014,20(4):1247-1250.
[13]Rosen M J,Kunjappu J T.Surfactants and interfacial phenomena[M].4th Edition.Hoboken:John Wiley&Sons,Inc.,2012,347-352.
[14]Li P,Wang W,Du Z,et al.Adsorption and aggregation behavior of surface active trisiloxane room-temperature ionic liquids[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2014,450:52-58.
[15]Li R,Yan F,Zhang J,et al.The self-assembly properties of a series of polymerizable cationic gemini surfactants:Effect of the acryloxyl group[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2014,444:276-282.
[16]Maozhang T,Yaxun F,Gang J,et al.Spontaneous aggregate transition in mixtures of a cationic gemini surfactant with a double-chain cationic surfactant[J].Langmuir the Acs Journal of Surfaces&Colloids,2012,28(33):12005-12014.
[17]Wang G,Qu W,Du Z,et al.Adsorption and aggregation behavior of tetrasiloxane-tailed surfactants containing oligo(ethylene oxide)methyl ether and a sugar moiety[J].Journal of Physical Chemistry B,2011,115(14):3811-3818.
[18]Ren S J,Zheng L Q,Sun J C.Self-assembly of surfactants regulated by weak interaction(Ⅰ):The classification of weak interactions[J].China Surfactant Detergent&Cosmetics,2018,48(11):611-616.
[2]Zana R,Xia J.Gemini surfactants:synthesis,interfacial and solutionphase behavior,and applications[J].Journal of Colloid&Interface Science,2003,272(2):502.
[3]Zana R,Talmon Y.Dependence of aggregate morphology on structure of dimeric surfactants[J].Nature,1993,362(6417):228-230.
[4]Zana R.Dimeric and oligomeric surfactants.Behavior at interfaces and in aqueous solution:a review[J].Advances in Colloid&Interface Science,2002,97(1):205-253.
[5]Kang P,Xu H J,Song C L.Properties of binary surfactant system of alkyl polyglycosides and alpha-sulphonated fatty acid methyl ester[J].Tenside Surfactants Detergents,2013,50(3):192-198.
[6]Han Z,Yang X,Yong L,et al.Physicochemical properties and phase behavior of didecyldimethylammonium chloride/alkyl polyglycoside surfactant mixtures[J].Journal of Surfactants&Detergents,2015,18(4):641-649.
[7]Warwel S,Brüse F,Schier H.Glucamine-based gemini surfactants I:Gemini surfactants from long-chain-alkyl glucamines andα,ω-diepoxides[J].Journal of Surfactants&Detergents,2004,7(2):181-186.
[8]Fielden M L,Perrin C,Kremer A,et al.Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro[J].Febs Journal,2010,268(5):1269-1279.
[9]Wilk K A,Syper L,Domagalska B W,et a1.Aldonamide-type gemini surfactants:synthesis,structural analysis,and biological properties[J].Journal of Surfactants and Detergents,2002,5(3):235-244.
[10]Yoshimura T,Umezawa S,Fujino A,et al.Equilibrium surface tension,dynamic surface tension,and micellization properties of lactobionamide-type sugar-based gemini surfactants[J].Journal of Oleo Science,2013,62(6):353-362.
[11]Liu S,Sang R,Hong S,et al.A novel type of highly effective nonionic gemini alkyl O-glucoside surfactants:a versatile strategy of design[J].Langmuir,2013,29(27):8511-8516.
[12]Wang G,Zhang D,Du Z,et al.Spontaneous vesicle formation from trisiloxane-tailed gemini surfactant[J].Journal of Industrial and Engineering Chemistry,2014,20(4):1247-1250.
[13]Rosen M J,Kunjappu J T.Surfactants and interfacial phenomena[M].4th Edition.Hoboken:John Wiley&Sons,Inc.,2012,347-352.
[14]Li P,Wang W,Du Z,et al.Adsorption and aggregation behavior of surface active trisiloxane room-temperature ionic liquids[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2014,450:52-58.
[15]Li R,Yan F,Zhang J,et al.The self-assembly properties of a series of polymerizable cationic gemini surfactants:Effect of the acryloxyl group[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2014,444:276-282.
[16]Maozhang T,Yaxun F,Gang J,et al.Spontaneous aggregate transition in mixtures of a cationic gemini surfactant with a double-chain cationic surfactant[J].Langmuir the Acs Journal of Surfaces&Colloids,2012,28(33):12005-12014.
[17]Wang G,Qu W,Du Z,et al.Adsorption and aggregation behavior of tetrasiloxane-tailed surfactants containing oligo(ethylene oxide)methyl ether and a sugar moiety[J].Journal of Physical Chemistry B,2011,115(14):3811-3818.
[18]Ren S J,Zheng L Q,Sun J C.Self-assembly of surfactants regulated by weak interaction(Ⅰ):The classification of weak interactions[J].China Surfactant Detergent&Cosmetics,2018,48(11):611-616.