Synthesis and antibacterial activities of quaternary ammonium salts with different alkyl chain lengths grafted on polyvinyl alcohol-formaldehyde sponges

Abstract N,N-Dialkyl Ammonium Salts of Saturated Heterocyclic Amines, Antimicrobial Activity Antimicrobial activity of N-alkyl-N-dodecylpiperidinium bromides and N-ethyl-N-dodecylheterocycloalkyl ammonium bromides (pyrrolidine, morpholine, perhydroazepine) deter mined on grampositive and gramnegative bacteria, yeasts and moulds, presented as minimum inhibition concentration (MIC). Comparison of the effect of change of structure: lenghtening of alkyl chain, change of heterocyclic ring. Change in the lenght of alkyl chain markedly affects the antimicrobial activity, change of heterocyclic ring has no substantial effect. The most active compounds were N-heptyl-and N-hexyl-N-dodecylpiperidinium bromides.

Download Full-text

Relationship Between Triboelectric Charging and Surface Modification of Human Hair: Polymeric Versus Monomeric Long Alkyl Chain Quaternary Ammonium Salts

Textile Research Journal ◽

10.1177/004051758705700910 ◽

1987 ◽

Vol 57 (9) ◽

pp. 543-548 ◽

Cited By ~ 2

Author(s):

J. Jachowicz ◽

M. Garcia ◽

G. Wis-Surel

Keyword(s):

Surface Modification ◽

Quaternary Ammonium ◽

Human Hair ◽

Alkyl Chain ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Triboelectric Charging ◽

Long Alkyl Chain

Download Full-text

The influence of cation and anion structure of new quaternary ammonium salts on adsorption and leaching

Holzforschung ◽

10.1515/hf.2005.030 ◽

2005 ◽

Vol 59 (2) ◽

pp. 190-198 ◽

Cited By ~ 8

Author(s):

Jadwiga Zabielska-Matejuk

Keyword(s):

Scots Pine ◽

Quaternary Ammonium ◽

Chemical Structure ◽

Alkyl Chain ◽

Chloride Ion ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Physical Processes ◽

Water Leaching ◽

Pine Wood

Abstract This study examined the effect of cation and anion chemical structure of new quaternary ammonium and imidazolium compounds (QAC, bis-QAC, IC, bis-IC) on the adsorption onto Scots pine wood (Pinus sylvestris L.) and resistance to water leaching. The group of copper (II) modified QACs, containing copper-chloro-acetate complexes in the anion structure, was also examined. The length of alkyl hydrophobic substituents in the cation structure significantly influences adsorption. The adsorption characteristics were statistically related to the alkyl chain length of new quaternary ammonium salts (quantitative correlations between CMC and adsorption values). Bis-ICs adsorb onto Scots pine wood with the greatest difficulty and the slowest and are also leached to the greatest degree. A varied adsorption of chloride ion cations and a several times higher leaching of chlorides than cations of the examined salts from the saturated wood were observed. The anion modification of bis-QAC and bis-IC of copper-chloro-acetate complexes causes decreased adsorption and resistance to the leaching of these salts. As a result of the performed regression analysis of Langmuir and Freundlich adsorption isotherms, it was found that the adsorption of the examined compounds onto wood was governed by both chemical and physical processes. New quaternary ammonium and imidazolium compounds represent potential wood preservatives.

Download Full-text

Safety Assessment of Trimoniums as Used in Cosmetics

International Journal of Toxicology ◽

10.1177/1091581812467378 ◽

2012 ◽

Vol 31 (6_suppl) ◽

pp. 296S-341S ◽

Cited By ~ 9

Author(s):

Lillian C. Becker ◽

Wilma F. Bergfeld ◽

Donald V. Belsito ◽

Ronald A. Hill ◽

Curtis D. Klaassen ◽

...

Keyword(s):

Quaternary Ammonium ◽

Safety Assessment ◽

Alkyl Chain ◽

Expert Panel ◽

Safety Data ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Entire Group ◽

Product Usage ◽

Cosmetic Product

Quaternary ammonium salts, including alkyl chain, alkanol, and polymer derivatives (trimoniums) are used in cosmetics mainly as surfactant-cleansing agents, hair-conditioning agents, and antistatic agents. The Cosmetic Ingredient Review Expert Panel reviewed the relevant animal and human data and noted gaps in the available safety data for some of the trimomiums. The available data on many of the trimoniums are sufficient, however, and similar structural activity relationships, functions in cosmetics, and cosmetic product usage supported extending these data to the entire group. These ingredients were determined to be safe in the present practices of use and concentration when formulated to be nonirritating.

Download Full-text

Synthesis and Surfactant Studies of Dialkyl Dimethyl Quaternary Ammonium Bromide Formulations

American Journal of Undergraduate Research ◽

10.33697/ajur.2006.019 ◽

2006 ◽

Vol 5 (3) ◽

Cited By ~ 1

Author(s):

Rocky Barney ◽

Tony Stark ◽

Dru Delaet

Keyword(s):

Quaternary Ammonium ◽

Carbon Chain ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Ammonium Bromide ◽

Tertiary Amines ◽

Alkyl Bromide ◽

Component Systems ◽

Multiple Component ◽

Chain Lengths

Quaternary ammonium salts (otherwise known as quats) are commonly used active ingredients in biocide formulations used in the anti-microbial industry. Although quats have been established to be effective biocides, there are few studies investigating the maximization of biocidal efficacy in multiple component formulations using various carbon chain lengths. Reported here is the synthesis based on the Sn2 reaction of tertiary amines with alkyl bromide. Surfactant studies of the single and dual component systems were conducted, and the evaluation is explored.

Download Full-text

Design, Synthesis, Antibacterial, and Antitumor Activity of Linear Polyisocyanide Quaternary Ammonium Salts with Different Structures and Chain Lengths

Molecules ◽

10.3390/molecules26185686 ◽

2021 ◽

Vol 26 (18) ◽

pp. 5686

Author(s):

Hongguang Zhang ◽

Lijia Liu ◽

Peng Hou ◽

Jun Liu ◽

Shuang Fu

Keyword(s):

Antibacterial Activity ◽

Quaternary Ammonium ◽

Main Chain ◽

Quaternary Ammonium Salts ◽

Polymer Materials ◽

Ammonium Salts ◽

Organic Polymer ◽

Side Chain ◽

E Coli ◽

Chain Lengths

The development of organic polymer materials for disinfection and sterilization is thought of as one of the most promising avenues to solve the growth and spread of harmful microorganisms. Here, a series of linear polyisocyanide quaternary ammonium salts (L-PQASs) with different structures and chain lengths were designed and synthesized by polymerization of phenyl isocyanide monomer containing a 4-chloro-1-butyl side chain followed by quaternary amination salinization. The resultant compounds were characterized by 1H NMR and FT-IR. The antibacterial activity of L-PQASs with different structures and chain lengths against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was evaluated by determining the minimum inhibitory concentrations (MICs). The L-POcQAS-M50 has the strongest antimicrobial activity with MICs of 27 μg/mL against E. coli and 32 μg/mL against S. aureus. When the L-PQASs had the same polymerization degree, the order of the antibacterial activity of the L-PQASs was L-POcQAS-Mn > L-PBuQAS-Mn > L-PBnQAS-Mn > L-PDBQAS-Mn (linear, polyisocyanide quaternary ammonium salt, monomer, n = 50,100). However, when L-PQASs had the same side chain, the antibacterial activity reduced with the increase of the molecular weight of the main chain. These results demonstrated that the antibacterial activity of L-PQASs was dependent on the structure of the main chain and the length of the side chain. In addition, we also found that the L-POcQAS-M50 had a significant killing effect on MK-28 gastric cancer cells.

Download Full-text

Unprecedented and Readily Tunable Photoluminescence from Aliphatic Quaternary Ammonium Salts

10.33774/chemrxiv-2021-3w14l ◽

2021 ◽

Author(s):

Saixing Tang ◽

Zihao Zhao ◽

Tianjia Yang ◽

Yunzhong Wang ◽

Xiaohong Chen ◽

...

Keyword(s):

Quaternary Ammonium ◽

Alkyl Chain ◽

Phase Transfer ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Excitation Wavelength ◽

Mechanical Stimuli ◽

Dual Emission ◽

Phase Transfer Catalysts ◽

Counter Ions

Compounds bearing aliphatic amines could be emissive under proper conditions. Their ionized counterparts, quaternary ammonium salts (QASs), which are widely used as phase-transfer catalysts, ionic liquids, disinfectants and surfactants, however, are known as luminescence quenchers and thought to be nonemissive. Here we report the unprecedented intrinsic fluorescence-phosphorescence dual emission from a diversity of QASs, which can also be finely regulated by excitation wavelength, alkyl chain length, counter ions, mechanical stimuli, etc. The bright photoluminescence along with distinct afterglow and tunable multicolor emissions enables advanced multimode anticounterfeiting for QAS solids. This finding refreshes the cognition of QASs and would inspire emerging applications by utilizing their intrinsic luminescence. Furthermore, it opens opportunities for the investigation of QAS related processes and functions in a photophysical approach and affords strong implications for the fabrication of novel nonconventional luminophores.

Download Full-text