Bifunctional N-Oxides of Alkyldiamidoamines
Tóm tắt
A homologous series of new surface-active 1,1-bis{[3-(N,N-dimethylamino)ethyl]-amido}alkane-di-N-oxides were synthesized in the reaction of an appropriate diethyl 2-alkylmalonate with N,N-dimethylethylenediamine followed by oxidation with an aqueous solution of hydrogen peroxide. The adsorption isotherms of their aqueous solutions were measured and evaluated to obtain adsorption parameters: critical micelle concentration (CMC), surface excess concentration (ΓCMC), equilibrium surface tension at the CMC (γ
CMC), cross-sectional area of the adsorbed surfactant molecule (A
CMC), standard free energies of adsorption
$$\left({\Updelta G_{\text{ads}}^{\text{o}} } \right),$$
and micellization
$$ \left( {\Updelta G_{\text{CMC}}^{\text{o}}} \right).$$
Tài liệu tham khảo
Sommerdijk NAJM, Hoeks TL, Booy KJ, Feiters MC, Nolte RJM, Zwanenburg B (1998) Dicephalic surfactants. Chem Commun 7:743–744
Czichocki G, Engler G, Ulsperger E (1974) D-Gluconsaure-δ-lacton als Baustein von Tensiden. J Prakt Chem 316:895–900
Hill K-H, Kuester H, Biermann M, Fabry B, Hensen H, Wegener I, Weuthen M (1993) Fatty acid bis-sorbityl amide(s) and their prepn. Useful for the prepn. of washing, rinsing or cleaning agents and hair or body care prods. Ger Patent 4,238,210
Blease TG, Bevinakatti HS, Reekmans SIJ, Scovell EG, Davies SJ (2002) Agrochemical compositions and surfactant compounds. US Appl Patent 0168417
Schmidt RR, Jankowski K (1996) New types of nonionic surfactants with sugar head groups. Liebigs Ann 4:867–869
Pitt AR, Newington IM (1994) Non-ionic surface active compounds. US Patent 5,298,191
Burczyk B, Syper L, Wilk KA (1999) New surface active aldonamides and their preparation. Polish Appl Patent P-331294
Wilk KA, Syper L, Burczyk B, Sokołowski A, Domagalska BW (2000) Synthesis and surface properties of new dicephalic saccharide-derived surfactants. J Surfactant Deterg 3:185
Neimert-Andersson K, Blomberg E, Somfai P (2004) Stereoselective synthesis of polyhydroxyl surfactants. Stereochemical influence on langmuir monolayers. J Org Chem 69:3746–3752
Neimert-Andersson K (2005) Synthesis of polyhydroxylated surfactants. Comparison of surfactant stereoisomers and investigation of hemolytic activity. Doctoral Thesis, Royal Institute of Technology KHT, Stockholm
Sauer JD (1990) Amine oxides. In: Richmond JM (ed) Cationic surfactants: organic chemistry. Surfactant Science Series, vol 34. Marcel Dekker, Inc., New York, pp 275–295
Piasecki A, Karczewski S, Maliszewska I (2007) Synthesis and properties of 1, 1-bis{[3-(N, N-dimethylamino)propyl]amido}alkane-di-N-oxides. J Surfactant Deterg 10:93–101
Simon J, Le Moigne J, Markovitsi D, Dayantis J (1980) Annelides. 3. Complexation of dioxygen in organized cobaltous complex assemblies. A new approach to kinetic studies in micellar phases. J Am Chem Soc 102:7247–7252
Piasecki A, Wójcik B, Łuczyński J (2003) New di-amidoamines derivatives of N,N-dimethylethylenediamine and method of their manufacture. Polish Appl Patent 361368
Piasecki A, Wójcik B, Łuczyński J (2003) New di-amidoamines N-oxides derivatives of N,N-dimethylethylenediamine and method of their manufacture. Polish Appl Patent 361369
Myers D (2006) Surfactant science and technology, 3rd edn. Wiley, Hoboken, p 102
Rosen MJ (2004) Surfactants and interfacial phenomena, 3rd edn. Wiley, Hoboken
Lunkenheimer K, Haage K, Hirte R (1999) Novel results on the adsorption properties of n-alkyldimethylphosphine oxides at the air/water interface. Langmuir 15:1052–1058
Lunkenheimer K, Barzyk W, Hirte R, Rudert R (2003) Adsorption properties of soluble, surface-chemically pure n-alkanoic acids at the air/water interface and the relationship to insoluble monolayer and crystal structure properties. Langmuir 19:6140–6150
Klevens HB (1953) Structure and aggregation in dilute solutions of surface-active agents. J Am Oil Chem Soc 30:74–80
Birnie ChR, Malamud D, Schnaare RL (2000) Antimicrobial evaluation of N-alkyl betaines and N-alkyl-N, N-dimethylamine oxides with variation in chain length. Antimicrob Agents Chemother 44:2514–2517