New urea-based surfactants derived from alpha,omega-amino acids.
New anionic urea-based surfactants derived from alpha,omega-amino acids and in particular from beta-alanine were synthesized and their solution properties characterized by electrical conductivity, equilibrium surface tension, and steady-state fluorescence spectroscopy techniques. Double-chain surfactants and the single-chain surfactant containing a sulfate head group exhibited the lowest critical micelle concentration (cmc) values and superior efficiency in lowering surface tension. All surfactants promoted adsorption relative to micellization, and micellar parameters were sensitive to the hydrophobicity of the amino acid residue. The polarity of the interfacial region, measured with the solvatochromic probe E(T)(30) (Reichardt's betaine dye), was similar to sodium dodecyl sulfate (SDS) micelles.
Faustino
Célia M C
CM
University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal. cfaustino@ff.ul.pt
Calado
António R T
AR
Garcia-Rio
Luís
L
D000409:Alanine / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002151:Calorimetry; D004553:Electric Conductivity; D004983:Ethanolamines / Q000737:chemistry; D005998:Glycine / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry*; D014508:Urea; D014631:Valerates / Q000737:chemistry
C526585:2-aminoethyl phosphate; D000596:Amino Acids; D004983:Ethanolamines; D010755:Organophosphates; D013501:Surface-Active Agents; D014631:Valerates; D014508:Urea; C020619:ethanolamine O-sulfate; D000409:Alanine; D005998:Glycine