Synthesis and Properties of Three N‐Alkyl Bis‐Quaternary Ammonium Salt Surfactants

Abstract

Three N-alkyl bis-quaternary ammonium salt surfactants were synthesized by using epichlorohydrin, trimethylamine hydrochloride, and N,N-dimethylalkyl amine as raw materials in a two-step manner. The products were characterized by 1 H NMR and MS, confirming the successful synthesis of 2-Hydroxy-N 1 ,N 1 ,N 3 ,N 3-tetramethyl-N 3dodecylpropane-1,3-diammonium chloride (HPDDC), 2-Hydroxy-N 1 ,N 1 ,N 3 ,N 3-tetramethyl-N 3-tetradecylpropane-1,3-diammonium chloride (HPTDC), and 2-Hydroxy-N 1 , N 1 , N 3 , N 3-tetramethyl-N 3-hexadecylpropane-1,3-diammonium chloride (HPHDC). Moreover, the influence of carbon chain length on surface-active properties, foaming properties, and paraffin liquid emulsion stability was investigated. Results indicated that critical micelle concentrations (cmc) decreased with increasing carbon chain length from 12 to 16, and the cmc and γ cmc were lower than those of Dodecyl trimethyl ammonium chloride (DTAC). The products exhibited better foam properties and worse emulsifying performance than those of DTAC. The Krafft points of all products were determined to be below 0 C. Moreover, the products also demonstrated outstanding antibacterial properties.

Quaternary Ammonium Compounds and Their Composites in Antimicrobial Applications

“…[121][122][123][124] Liu et al used an organic reaction to synthesize 2-Hydroxy-N 1 ,N 1 ,N 3 ,N 3 -tetramethyl-N 3 -dodecylpropane-1,3-diammonium chloride (HPDDC), 2-Hydroxy-N, 1 N 1 ,N 3 ,N 3 -tetramethyl-N 3 -tetradecylpropane-1,3-diammonium chloride (HPTDC), and 2-Hydroxy-N, 1 N, 1 N 3 ,N 3 -tetramethyl-N 3 -hexadecylpropane-1,3-diammonium chloride (HPHDC), generating a QAC-hybrid derived from epichlorohydrin and trimethylamine hydrochloride. [124] The inherent surfactant properties of QACs afforded the QAC-hybrid HPHDC diminished repulsive forces between ionic groups, resulting in a more compact surfactant arrangement at the air/liquid interface. Consequently, the surface area conducive to foam stability was increased, presenting a novel approach to formulating next-generation household antiseptics.…”

“…Furthermore, addition reaction has been employed to conjugate QACs with small molecules or additional QACs, thereby enhancing antibacterial activity. [ 121–124 ] Liu et al used an organic reaction to synthesize 2‐Hydroxy‐N 1 ,N 1 ,N 3 ,N 3 ‐tetramethyl‐N 3 ‐dodecylpropane‐1,3‐diammonium chloride (HPDDC), 2‐Hydroxy‐N, 1 N 1 ,N 3 ,N 3 ‐tetramethyl‐N 3 ‐tetradecylpropane‐1,3‐diammonium chloride (HPTDC), and 2‐Hydroxy‐N, 1 N, 1 N 3 ,N 3 ‐tetramethyl‐N 3 ‐hexadecylpropane‐1,3‐diammonium chloride (HPHDC), generating a QAC‐hybrid derived from epichlorohydrin and trimethylamine hydrochloride. [ 124 ] The inherent surfactant properties of QACs afforded the QAC‐hybrid HPHDC diminished repulsive forces between ionic groups, resulting in a more compact surfactant arrangement at the air/liquid interface.…”

Highly Effective and Broad-Spectrum Antimicrobial Quaternary Ammonium Salts Containing Camphene Structure: Preparation, Surface-Active Properties, and Bioassay

“…With the lucubrating of research, the development of modern QASs has been in rapid progress over the past 2 decades. The types of cations have evolved from the simplest alkyl chain to diverse organic skeleton, and the change of the anions has also varied from halogen ions to other inorganic anions, such as hydrogen sulfate, tetrafluoroborate, hexafluorophosphate, etc. – Moreover, the number of carbon chain present has upgraded from single-chain to double-chain QASs, and the number of positive charges present can be divided into mono-, bis (gemini)-, and multi-QAS. , These led to the enhancement of broad-spectrum antimicrobial properties of the following developed QASs.…”

“… 5 – 7 Moreover, the number of carbon chain present has upgraded from single-chain to double-chain QASs, and the number of positive charges present can be divided into mono-, bis (gemini)-, and multi-QAS. 8 , 9 These led to the enhancement of broad-spectrum antimicrobial properties of the following developed QASs.…”