Surface Tension and Aggregation Properties of Novel Cationic Gemini Surfactants with Diethylammonium Headgroups and a Diamido Spacer

Zhang, Qi; Gao, Zhinong; Xu, Feng; Tai, Shuxin; Liu, Xueguo; Mo, Shaobo; Niu, Fei

doi:10.1021/la3011212

Cited by 113 publications

(78 citation statements)

References 42 publications

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“…max A min 1 Γ × = N A (2) Where, N A is Avogadro's number. 32 It is also quite clear that surface tension values of these surfactants (n = 12, 14, 16) are lower than the corresponding gemini surfactants of large diethyl ammonium headgroups, 14 which indicates the gemini surfactants (a, b and c) with higher surface activity. 31 With the hydrocarbon chain length increasing, the gemini surfactant molecules pack more loosely, thus the γ CMC of c compound is more than that of a or b compound.…”

Section: Surface Activitymentioning

confidence: 99%

Synthesis and physiochemical properties of novel gemini surfactants with phenyl-1,4-bis(carbamoylmethyl) spacer

et al. 2015

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A series of novel gemini surfactants, namely phenyl-1,4-bis [(carbamoylmethyl) N,N-dimethylalkyl ammonium chloride)] (a, b and c) were synthesized systematically and characterized by FT IR, 1 H NMR, 13 C NMR and MS. Their surface and bulk properties were evaluated by surface tension, conductivity, viscosity, dynamic light scattering (DLS) and transmission electron microscopy (TEM) measurements. These surfactants have been found to have low surface tension (γ γ γ γCMC) values as compared to other categories of gemini cationic surfactants and to form vesicles in solution at low concentration. The DLS and TEM studies showed that the aggregations of the above surfactants changed from larger globule vesicles and smaller globule micelles to network aggregates and then to globule vesicles with the increase of the surfactant concentration. It is assumed that this unusual aggregation behavior is related to the transformation of molecular conformation, phenyl-1,4-bis(carbamoylmethyl) spacer with rigidity and a hydrogen-bonding capability. The thermodynamic parameters of micellization process, namely, standard Gibbs free energy (∆Gºm), enthalpy (∆Hºm) and entropy (∆Sºm) were derived from conductivity measurement at different temperatures. Krafft points of three gemini surfactants are very low.Gemini surfactants are amphiphilic molecules containing two hydrophilic head groups and two hydrophobic tails connected by a spacer at two head groups. Many studies have been carried out on gemini surfactants, focusing on their unique surface and bulk properties such as high surface activity, low critical micelle concentration(CMC), and more abundant self-assembly morphologies than the corresponding traditional single-chain surfactants. 1-4 Owing to these unique properties, gemini surfactants have been widely used in industrial detergency, the construction of high-porosity materials, templates for the synthesis of nanoparticles, nanorods, etc. 5-10 So, aggregation behavior of surfactants attract great attention in academic research. The chemical structures of the gemini surfactants play an important role in their aggregation behavior. 11, 12 Especially, the nature of the spacer group (length, flexibility, polarity) has been shown to be of the utmost importance in determining the solution properties of aqueous gemini surfactants. 13, 14 These effects lead to the synergism of two alkyl tails of a gemini molecule, the change in the charge density of its headgroup, the variation of its molecule geometry by which rich structures and morphologies of aggregates yield, etc. More detailed, the flexible spacer influences the above functions of the gemini mainly depending on its length. 6,15 Too long flexible spacer can bend toward the alkyl tails so as to meet the chemical environment around the molecule, by which the molecule self-assembly is influenced. The effect of the short rigid spacer is almost identical with that of the flexible spacer having a similar length. 16 However, the long rigid spacer yields quite different effects from the flex...

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Section: Surface Activitymentioning

confidence: 99%

Synthesis and physiochemical properties of novel gemini surfactants with phenyl-1,4-bis(carbamoylmethyl) spacer

et al. 2015

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“…38,39 Following that, 2-chloro-N-dodecylacetamide was subsequently quaternized by different heterocyclic amines (N-methyl piperidine, N-methyl pyrrolidine, N-methyl imidazole and N-methyl morpholine) in the second step to get amide-functionalized SAILs. The detailed methodology of synthesis and characterization data (NMR and mass) are provided in Annexure 1 (ESI †).…”

Section: Synthesis and Thermal Stabilitymentioning

confidence: 99%

Effect of cationic head group on micellization behavior of new amide-functionalized surface active ionic liquids

Kamboj

Bharmoria

Chauhan

et al. 2014

Phys. Chem. Chem. Phys.

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Amide-functionalized surface active ionic liquids (SAILs), 1-methyl-1-dodecyl piperidinium chloride, [C12APip][Cl]; 1-methyl-1-dodecyl pyrrolidinium chloride, [C12APyrr][Cl]; 1-methyl-3-dodecyl imidazolium chloride, [C12Amim][Cl], and 1-methyl-1-dodecyl morpholinium chloride, [C12AMorph][Cl], have been synthesized, characterized and investigated for thermal stability, and micellization behavior in aqueous medium. The introduction of an amide moiety in the alkyl chain decreased the thermal stability of the functionalized SAILs compared to non-functionalized SAILs bearing a simple alkyl chain. A variety of state of the art techniques, viz. tensiometry, conductometry, steady-state fluorescence, isothermal titration calorimetry (ITC), dynamic light scattering (DLS) and atomic force microscopy (AFM), have been employed to investigate the micellization behavior. Amide-functionalized SAILs have shown much lower critical micelle concentration, cmc, and better surface active properties as compared to homologous non-functionalized SAILs. Steady-state fluorescence has provided information about cmc, aggregation number (Nagg) and polarity of the cybotactic region of the micelles, whereas ITC has provided insights into the thermodynamics of micellization. Furthermore, the size and shape of the micelles have been investigated using DLS and AFM techniques.

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“…The y values considerably and continu ously decreased with increasing concentration when c ex ceeded the CMC value for 14-B-14. Provided that the interface was saturated at CMC, Zhang et al [18] thought that this result was attributed to the decreased portion of y caused by increasing the counterion activity was greater than the in creased portion of y caused by decreasing the surfactant ion and increasing the aggregate activity. Provided that the inter face was unsaturated at CMC [19], they ascribed this phenom enon to the continued filling of the interface above the CMC.…”

Section: Synthesis O F C Ationic G E M In I Surfactantsmentioning

confidence: 99%

“…Moreover, I1/I3 also reflected the compactness of the surfactant aggregates. When the surfactant concentra tion was above the CMC value, I1/I3 remains constant be cause of the compactness of the aggregate structures and the unchanged microenvironment [18]. h / k for 14-B-14 gradually decreased with increasing concentration when the surfactant concentration is above CMC, indicating that 14-B-14 formed loosely bound aggregates in solution [18].…”

Section: 2 Steady-state Fluorescencementioning

confidence: 99%

Synthesis and Properties of Alkyl Dibenzyl Ether Quaternary Ammonium Gemini Surfactant

Zhu¹,

Hu²,

Wang³

et al. 2015

Tenside Surfactants Detergents

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Three g e m in i surfactants w ith d ib e nzyl e th e r spacer (1 0 -B -1 0 ,12-B-12, and 14-B-14) w e re synthesized and characterized. The su r face a ctivity and th e rm o d y n a m ic p ro p e rtie s o f m ice lliza tio n w e re d e te rm in e d by surface te n sio n , steady-state flu o re sce n ce m icroscopy, and c o n d u c tiv ity m e th o d s. The th e rm o d y n a m ic pa ra m eters o f m ic e lliz a tio n (AmicG°, AmicH°, and AmicS°) derived fro m th e electrical c o n d u c tiv ity m e a s u re m e n t im p lie d th a t th e m ic e lliz a tio n o f th e se surfactants w as d rive n by e n thalpy. The e n th a lp y -e n tro p y c o m p e n s a tio n o f m ic e lliz a tio n sh o w e d th a t th e s ta b ility o f m ice lle s increased w ith in creasing alkyl chain le n g th . Finally, w e e valuated th e effects o f alkyl chain le n g th on th e in te rfa cia l te n s io n , fo a m a b ility, and th e e m u ls io n stability. Key w o rd s : G e m in i su rfa cta n t, critical m ice lle co n ce n tra tio n , degree o f c o u n te rio n association, th e rm o d y n a m ic param eters, e n th a lp y -e n tro p y c o m p e n s a tio n S yn th ese u nd E ig e n s c h a fte n vo n q u a te rn ä re n A lk y ld ib e nz y le th e r a m m o n iu m -C e m in ite n s id e n . Es w u rd e n d rei G e m in i te n s id e m it e in e m D ib e n zyle th e rsp a ce r (10-B-10, 12-B-12 u nd

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Surface Tension and Aggregation Properties of Novel Cationic Gemini Surfactants with Diethylammonium Headgroups and a Diamido Spacer

Cited by 113 publications

References 42 publications

Synthesis and physiochemical properties of novel gemini surfactants with phenyl-1,4-bis(carbamoylmethyl) spacer

Synthesis and physiochemical properties of novel gemini surfactants with phenyl-1,4-bis(carbamoylmethyl) spacer

Effect of cationic head group on micellization behavior of new amide-functionalized surface active ionic liquids

Synthesis and Properties of Alkyl Dibenzyl Ether Quaternary Ammonium Gemini Surfactant

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