Synthesis, Characterization and Properties of New Lauryl Amidopropyl Trimethyl Ammoniums

Abstract

A new lauryl amidopropyl trimethyl ammonium methyl carbonate with the formula CH3(CH2)10CONH(CH2)3N+(CH3)3CH3CO3− was synthesized via a high pressure process with tertiary amines and dimethyl carbonate, and its chemical structure was confirmed using 1H‐NMR spectra, mass spectral fragmentation, and FTIR spectroscopic analysis. In addition, several quaternary ammonium salts with new counterions X− (X−=HCO3−, HCOO−, CH3COO−, CH3CH(OH)COO−) were also synthesized by the ion exchange reaction of methyl carbonate quaternary ammoniums with corresponding acids. The surface activities of these compounds were measured, including surface tension (γ), critical micelle concentration and minimum surface area (Amin) at 25 °C. Adsorption and micellization free energies of these quaternary ammonium salts in their solutions showed a good tendency towards adsorption at interfaces. The antimicrobial activities are reported for the first time against representative bacteria and fungi for lauryl amidopropyl trimethyl ammoniums. It was found that the antimicrobial potency was Gram‐positive bacteria > fungi > Gram‐negative bacteria.

Synthesis and Characteristics of Dodecyl Isopropylolamine and Derived Surfactants

“…The plots of the surface tension (c) vs the molar concentration on the natural logarithmic scale (lnC) for the salts at 25°C are shown in Figs. 3, 4 [17], cetyltrimethylammonium [18], 1-dodecylammonium [19], decyltrimethylammonium [20] and other type surfactants [21][22][23]. Table 2 indicates that the counterions are important for maximum values of surface excess concentration-C max , as well as the minimal surface area per molecule of surfactant-A min at the border of aqueous solution with air.…”

Undecanoic and 10‐Undecenoic Acid‐Based Amidobetaines and Amidoamine Oxides

“…Synthesis of 10-UDA Amidopropyl Amine Oxide (10-UDAAO) N-oxide derivative was prepared by stirring a cold solution of N-[3-(dimethylamino) propyl]undec-10-enamide (1a, 5 g, 0.0186 m) in 200 ml of acetone in a 250-ml round-bottomed flask kept in an ice bath. In this stirred solution, 30 % aqueous H 2 O 2 (0.061 m) solution was added drop by drop over a period of 30 min [18]. After completion of the addition, the reaction mixture was allowed to come to room temperature and stirred for 24 h. Progress of the reaction was monitored by TLC.…”

“…All these surfactants are designed to have an amide moiety in the hydrophobic part in order to increase their biodegradability [17,18]. All these surfactants are designed to have an amide moiety in the hydrophobic part in order to increase their biodegradability [17,18].…”

“…The present research work reports the synthesis of three types of 10-UDA-based surfactants, such as amphoteric amidobetaine, cationic amidobetaine chloride and nonionic amidoamine oxide, and evaluates their surface properties. All these surfactants are designed to have an amide moiety in the hydrophobic part in order to increase their biodegradability [17,18]. Undecanoic acid (UDA), the saturated analog of 10-UDA, has also been taken up for the synthesis of these three types of surfactants.…”

Preparation and Antimicrobial Activity of Rosin-based Carbamate Group-containing Quaternary Ammonium Salt Derivatives

“…As a result, the development of compounds that are environmentally friendly and biodegradable has gained much attention (Lim et al 2012). Furthermore, it has been reported that the water-solubility and biodegradability of compounds could be improved by adding new polar groups, such as ethers, esters, and amides, into the molecular structure (Liu et al 2012a).…”