Synthesis and Performance of Double-Chain Quaternary Ammonium Salt Glucosamide Surfactants

Abstract

A series of double-chain quaternary ammonium salt surfactants N-[N′[3-(gluconamide)] propyl-N′-alkyl]propyl-N, N-dimethyl-N-alkyl ammonium bromide (CnDDGPB, where n represents a hydrocarbon chain length of 8, 10, 12, 14 and 16) were successfully synthesized from D (+)-glucose δ-lactone, N, N-dimethyldipropylenetriamine, and bromoalkane using a two-step method consisting of a proamine-ester reaction and postquaternization. Their surface activity, adsorption, and aggregation behavior in aqueous solution were investigated via measurements of dynamic/static surface tension, contact angle, dynamic light scattering, and transmission electron microscopy. An analysis of their application performance in terms of wettability, emulsifying properties, toxicity, and antibacterial properties was conducted. The results show that with increasing the carbon chain length of the CnDDGPB surfactants, their critical micelle concentration (CMC) increased and the pC20 and efficiency in the interface adsorption of the target product gradually decreased. Moreover, the influence of the hydrophobic carbon chain length on the surface of polytetrafluoroethylene (PTFE) was even greater for the wetting effect, reducing the contact angle to 32° within the length range of C8–C14. The results of the contact angle change and the wettability experiments proved that C10DDGPB exhibited the best wettability. The liquid paraffin and soybean oil emulsification ability of CnDDGPB showed an upward trend followed by a downward trend with the growth of the carbon chain, with C12DDGPB exhibiting the best emulsification performance. The Dlong/Dshort ratio was far lower than 1, which indicates mixed-kinetic adsorption. The surfactants formed spherical micelles and showed a unique aggregation behavior in aqueous solution, which showed an increase–decrease–increase trend with the change in concentration. A cell toxicity and acute oral toxicity experiment showed that the CnDDGPB surfactants were less toxic than the commonly used surfactant dodecyldimethylbenzyl ammonium chloride (1227). In addition, at a concentration of 150 ppm, CnDDGPB exhibited the same bacteriostatic effect as 1227 at a concentration of 100 ppm. The results demonstrate that sugar-based amide cationic surfactants are promising as environmentally friendly disinfection products.

Quaternary Ammonium Salts: Insights into Synthesis and New Directions in Antibacterial Applications

“…For instance, Li et al synthesized a series of N -[ N ′(3-gluconamide)­propyl- N ′-alkyl]­propyl- N , N -dimethyl- N -alkyl ammonium bromide (CDDGPB) and compared the antibacterial activity of the QASs by changing the length of the grafted alkane segment. The synthesized CDDGPB had a similar antibacterial activity to DDBAC, while the toxicity was greatly reduced …”

“…The synthesized CDDGPB had a similar antibacterial activity to DDBAC, while the toxicity was greatly reduced. 55 2.3. Synthesis of Heterocyclic QASs.…”

Structural Significance of Hydrophobic and Hydrogen Bonding Interaction for Nanoscale Hybridization of Antiseptic Miramistin Molecules with Molybdenum Disulfide Monolayers

“…The dominant role of hydrophobic interactions in the MR intermolecular bonding that typifies the MR crystals [ 27 ] is thus preserved in the LCs despite of somewhat lesser density of MR packing (LC1) and reduced number of nearby molecules (LC2) in the interlayer as compared to the crystal packing. It is worth noting that hydrophobic intermolecular interaction is often of great significance for binding of surfactant molecules among themselves and with other organic species including peptides and DNA [ 34 , 35 , 36 ]. The contribution of other intermolecular bonds, the CH…O, CH… C π ones, is lower, though also significant, for stabilization of the MR layer.…”

Magnetic CuFe2O4 Nanoparticles with Pseudocapacitive Properties for Electrical Energy Storage

“…Colloidal methods offer many benefits for the fabrication of supercapacitor electrodes. The success in the application of colloidal methods is inevitably related to the development of advanced dispersant molecules and advanced dispersion mechanisms [33,34]. Colloidal strategies have a high potential for the development of supercapacitor electrodes.…”