Synthesis and surface properties of new dicephalic saccharide‐derived surfactants

Abstract

alkyl: n-C 12 H 25 , n-C 16 H 33 , n-C 18 H 37 ) were synthesized and characterized. Their structure and purity were confirmed by means of 1 H and 13 C nuclear magnetic resonance analysis and electrospray ionization mass spectrometry. Carbon spectra were verified using a DEPT experiment. The surface and interfacial properties such as critical micelle concentration (CMC), standard free energy of micellization, ∆G CMC , surface excess concentration, Γ CMC , and surface area demand per molecule, A CMC , were determined. The tertiary nitrogen atom seems to have a surprising effect on surfactant packing at the interface.Materials. D(+)-Glucose δ-lactone, α-D-glucoheptonic γ-lactone, lactobionic acid, and alkylamines (n-dodecyl, n-hexadecyl, n-octadecyl) were purchased from Aldrich Chemical Co. (Milwaukee, WI). Other reagents and solvents were of commercial grade and were not additionally purified before use. Water used for all experiments was doubly distilled and purified by means of a Millipore (Bedford, MA) Milli-Q purification system.Synthesis of N-alkyl-N,N-bis(2-cyanoethyl)amines: typical procedure. To n-dodecylamine (92.7 g, 0.5 mol) in methanol

Preparation and properties of new lactose‐based surfactants

“…This observation confirms a reported common feature of so-called sugar surfactants (6,8,11,13,14,16). As indicated by the Krafft temperature values (Table 2) , the surface excess concentration Γ CMC was calculated from the Gibbs adsorption isotherm.…”

“…As a continuation of our studies (8,12,15,16) related to nonionic surfactants comprising various carbohydrate hydrophilic groups, we present here a new family of compounds derived from lactose-N-alkanoyl-N-methyllactitolamines. These have the general formula shown (together with abbreviations) in Scheme 1.…”

“…Because of these valuable features, many research groups have directed their studies to various aspects of synthetic methodologies and properties of a wide range of saccharide surfactants that vary in their molecular architecture, such as single-chain, single-head entities (5)(6)(7)(8)(9)(10)(11)(12), di-chained (13,14) and dicephalic compounds (15,16) as well as bolaamphiphiles and gemini structures (17,18). Accordingly, all of these saccharide-derived materials exhibit similar general trends in surface-active behavior as reported for polyoxyethylene-based nonionics.…”

Review on chemically bonded geminis with cationic heads: second-generation interfactants

“…4 Zn(II) mediated cleavage of a phosphate diester in the stern layer of cationic gemini 16-2-16 [43] stronger hydrophilicity as compared with surfactants with oligo ethylene oxide head groups, and the hydrophobic part could consist of one, two, or even more chains such as hydrocarbon chains of fatty acids, long-chain fatty amines, or alcohols [44][45][46][47][48][49][50][51][52][53][54]. Novel green geminis derived from glucose and glucitol are able to show thermotropic behavior [55].…”

Photo-oxidative action in MCF-7 cancer cells induced by hydrophobic cyanines loaded in biodegradable microemulsion-templated nanocapsules

“…Co., (Taiwan). Surfactants, namely dicephalic N-dodecyl-N, Nbis[(3-D-glucoheptonylamido)propyl]amine (C12DGHA) and N-dodecyl-N,N-bis[(3-D-gluconylamido)propyl]amine (C12DGA), as well as gemini N,N'-bisdodecyl-N,N'-bis[ (3-glucoheptonylamido)propyl]ethylenediamine (bis(C12GHA)) and N,N'-bisdodecyl-N,N'-bis[(3-gluconylamido)propyl] ethylenediamine (bis(C12GA)), were synthesized as previously described (23,25,26) (for structures see Fig. 1B and C).…”