Synthesis and surface‐active properties of trimeric‐type anionic surfactants derived from tris(2‐aminoethyl)amine

Abstract

Trimeric-type anionic surfactants (3C n taAm, where n is a hydrocarbon chain length of 8, 10, or 12) with three hydrocarbon chains and three carboxylate headgroups were synthesized from tris(2-aminoethyl)amine, and their properties were investigated by surface tension, electrical conductivity, dynamic and static light-scattering, fluorescence of pyrene, and emulsification power techniques. The critical micelle concentrations (CMC) of 3C n taAm were 0.00092-0.00834 mmol dm −3 , and the surface tensions at the CMC were 33.3-39.9 mN m −1 . The areas per molecule occupied by 3C 10 taAm and 3C 12 taAm were extremely small, showing they were highly compact at the air/water interface. In addition, adsorption or micellization behavior of 3C n taAm was estimated by parameters such as pC 20 (the efficiency of surface adsorption), CMC/C 20 (the ease of adsorption relative to the ease of micellization), and ∆G M o (Gibbs energy of micellization). Dynamic and static light-scattering measurements of 3C n taAm showed a hydrodynamic radius of 45-61 nm above the CMC and aggregation numbers of 10-82 at the CMC, respectively. The fluorescence intensity ratio of the first to the third band in the emission spectra of pyrene started to lower from far above the CMC for 3C 8 taAm and 3C 10 taAm, and below the CMC for 3C 12 taAm. This suggests that loose micelles or premicellar aggregates are formed in solutions. Mixtures of aqueous solutions of 3C n taAm and toluene formed oil-in-water-type emulsions, and the stabilizing abilities were in the order of 3C 8 taAm > 3C 10 taAm > 3C 12 taAm. The degree of emulsification of 3C 8 taAm remained at 69% after 24 h of standing. Thus, 3C n taAm exhibited unique properties superior to monomeric or dimeric surfactants that were significantly influenced by their hydrocarbon chain lengths.

Physicochemical properties of anionic triple-chain surfactants in alkaline solutions

“…Recently, we have reported the synthesis of ringtype triple-chain surfactants from cyanuric chloride [10] and amide-type triple-chain surfactants from tris(2-aminoethyl)amine [11], revealing unique and unusual properties Scheme 1. such as very low cmc and formation of large aggregates. We have synthesized two anionic triple-chain surfactants [12,13], disodium 2,10-dialkyl-6-alkyl-3,6,9-triazaundecanedioate (referred to as 3C n dtda, where n is hydrocarbon chain length) and trisodium tris(N -2-ethylamino-N -2-alkylcarboxylato)-azane (3C n tata).…”

Synthesis, Surface‐Active Properties, and Emulsification Efficiency of Trimeric‐Type Nonionic Surfactants Derived From Tris(2‐aminoethyl)amine

“…Synthesis of Tris(alkanoyl-2-aminoethyl)amine [13] In a 1-L, three-neck flask fitted with a condenser, mechanical stirrer, and thermometer, about 29.2 g (0.2 mol) of tris(2-aminoethyl)amine dissolved in 70 mL toluene was placed. n-octanoyl, n-decanoyl, or n-dodecanoyl chloride (0.6 mol) dissolved in excess triethylamine (2.4 mol) was added dropwise.…”

Recent Advances in the Synthesis of Sulfonate Gemini Surfactants

“…The Gemini surfactants generally have two amphiphilic components and they are referred to as dimeric surfactants (Menger & Keiper, ). If the Gemini surfactants have three or four amphiphilic components, they are called trimeric surfactants (Yoshimuraa, Kimurab, Onitsukab, Shosenji, & Esumi, ; Zhou, Luo, Wang, Zhang, & Wang, ) or tetrameric surfactants (Menger & Migulin, ). They have similar properties to the dimeric surfactants.…”