5454-48-8Relevant articles and documents
Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles. Incorporation of multiple head groups leads to impressive antibacterial activity
Haldar, Jayanta,Kondaiah, Paturu,Bhattacharya, Santanu
, p. 3823 - 3831 (2005)
Two sets of novel multiheaded cationic amphiphiles bearing one, two, and three trimethyl-ammonium headgroups (T1, T2, and T3) and pyridinium headgroups (P1, P2, and P3), have been synthesized and tested for antimicrobial activities against both Gram-positive and Gram-negative bacteria. The multicationic headgroups in these amphiphiles were attached covalently via scissile ester-type linkages. The results were compared with those for known surface-active, nonhydrolyzable compounds cetyltrimethylammonium bromide (CTAB) and cetylpyridinium bromide (CPB). The killing effects of the new single-headed amphiphiles (T1 and P1) were lower than those of CTAB and CPB, but with an increase in the number of headgroups in the amphiphiles, the killing effects increased for both sets of compounds. It was found that amphiphiles with triple headgroups (T3 and P3) were most active among all the amphiphiles, whereas amphiphile P1 had a very poor killing effect on both types of bacteria. The multiheaded pyridinium amphiphiles were more active compared to their trimethylammonium counterparts. The time needed to kill bacteria with multiheaded amphiphiles was significantly less than that of single-headed amphiphiles. Owing to the presence of a cleavable ester moiety, these new amphiphiles are hydrolyzed spontaneously at physiological conditions. This property enables them to be readily metabolized and therefore have the potential to be superior disinfectants and antiseptics for food and body surfaces.
Synthesis of novel oil-soluble fluorinated surfactants via Wittig-Horner reaction
Zhang, Ding,Sha, Min,Xing, Ping,Pan, Renming,Lin, Xiangyang,Jiang, Biao
, p. 1652 - 1657 (2019/02/06)
In this paper, the synthesis and characterization of novel oil-soluble fluorinated surfactants were reported. Both Wittig and Wittig-Horner reaction were used for constructing the perfluorinated branch-chain structure, and the latter provided a better method through a three-step synthesis route which was easy worked up and low cost. The surface tension of novel products in toluene, n-hexane and nitromethane with concentrations of 0.1 mol/L, 0.05 mol/L, 0.025 mol/L, 0.0125 mol/L, 0.00625 mol/L and 0 mol/L were examined. The surface tension research of these surfactants showed that they can reduce the surface tension of organic reagents dramatically. For example, compound 1e can reduce the surface tension of nitromethane from 36.6 mN/m to 24.2 mN/m in the concentration of 0.1 mol/L, and the surface tension of toluene was reduced from 28.0 mN/m to 22.7 mN/m when the concentration of compound 1a was 0.1 mol/L.
Synthesis, Characterization, and Surface Activities of Polymeric Cationic Thiol Surfactants in Aqueous Medium
Zaky, Mohamed F.,Sabbah, Ibrahim A.,Hendawy, Mostafa E.,Abdel Hameed, Reda S.,Negm, Nabel A.
, p. 265 - 274 (2018/11/27)
A series of cationic polyurethane surfactants [PQ8-18] were synthesized by the reaction of alkyl bromoacetate (namely: octyl-, decyl-, dodecyl-, tetradecyl-, hexadecyl-, and octadecyl bromoacetate) as quaternizing agents and modified polyurethane contains tertiary amine species. Modified polyurethane was prepared by the reaction of toluene diisocyanate (TDI) and triethanol amine monomercaptoacetate. The chemical structures of the prepared surfactants were confirmed using elemental analysis, Fourier transform infrared spectroscopy (FTIR), and Proton nuclear magnetic resonance (1H NMR) spectroscopy. The molecular weight measurements of the prepared polymers showed that the segments of each polymer contain average 10 units of the urethane-triethanol amine mercaptoacetate. The surface activities of the prepared surfactants including: surface tension (γ), effectiveness (πcmc), concentration at micelle formation (CMC), efficiency (Pc20), maximum concentration at the interface (Γmax), and the average area occupied by each surfactant molecule at the interface at equilibrium (Amin) of surfactants solutions were established at 25°C. The surface tension and the critical micelle concentration values of the prepared surfactants were gradually decreased by the gradual increase of their alkyl chain length. The prepared cationic surfactants showed efficient activity as inhibitors for dissolution of carbon steel in an acidic medium and also as a biocide against the growth of bacteria, fungi, and yeast.
Biocidal activity and corrosion inhibition of some cationic surfactants derived from thiol polyurethane
Zaky, Mohamed F.,Sabbah,Negm,Hendawy
, p. 45 - 60 (2018/06/18)
S IX series of cationic polyurethane surfactants [PQ10-20] were synthesized by the reaction between different six esters (which prepared by condensation of fatty alcohols namely: octanol, decanol, dodecanol, tetradecanol, hexadecanol and octadecanol with bromoacetic acid) and polyurethane as quaternizing agent. The chemical structures of these surfactants were confirmed using elemental analysis, FTIR spectra,+HNMR and UV analysis. The surface activities of the synthesized cationic thiol polyurethane surfactants showed their tendency towards adsorption at the air/water interface. The adsorption tendency was estimated from the values of surface tension and the depression of surface tension at the critical micelle concentration. The studied surfactants were evaluated as antimicrobial agents against pathogenic and sulfur reducing bacteria using inhibition zone diameters and minimum inhibition concentration values. The synthesized cationic thiol polyurethane surfactants showed good antimicrobial activities against the tested microorganisms including Gram positive, Gram negative as well as fungi. The synthesized compounds were tested for the activity as corrosion inhibitors against carbon steel corrosion in 2N H2SO4 at 50, 100, 200, 400 and 600 ppm. The inhibition efficiencies of the tested compounds showed good inhibition and protection of the carbon steel. The corrosion inhibition tendency correlated to the surface activity and chemical structure of the compounds.
Phase Transfer Catalysis with Quaternary Ammonium Type Gemini Surfactants: O-Alkylation of Isovanillin
Boz, Mesut,Ba?türk, Sedat Semih
, p. 663 - 671 (2016/07/06)
In this paper, O-alkylation of isovanillin with unusual phase transfer catalysts alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants (also known as gemini surfactants) is described. Some dimeric surfactants with simple hydrophobic alkyl chains and others with hydrophobic alkyl chains containing ester functionalities with different lengths were synthesized and characterized in our laboratory. The alkylation of isovanillin with alkyl halide was successively carried out in the presence of potassium carbonate and a phase transfer catalyst in tetrahydrofuran. The same reactions were also performed with both the traditional phase transfer catalyst tetrabutylammonium bromide and without any catalyst. The results were compared with those of dimeric surfactants. Consequently, it was expressed that alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants successively exhibit the character of phase transfer catalysts through environmentally friendly procedures under mild conditions. The most significant feature of this work is that dimeric surfactants have been determined to act as phase transfer agents.
Synthesis of ester based cationic pyridinium gemini surfactants and appraisal of their surface active properties
Patial, Pankaj,Shaheen, Arifa,Ahmad, Ishtiaque
, p. 49 - 56 (2013/03/13)
New pyridinium gemini surfactants have been synthesized by esterification of halogenated carboxylic acids with long chain fatty alcohols furnishing respective esters (dodecyl-2-chloroacetate, tetradecyl-2-chloroacetate, hexadecyl-2-chloroacetate, dodecyl-2-bromoacetate, tetradecyl-2-bromoacetate and hexadecyl-2-bromoacetate) followed by their subsequent treatment with 4,4′-trimethylene dipyridine resulting in the formation of title Gemini surfactants: 4,4′-(propane-1,3-diyl)bis1-{2-(dodecyloxy)-2-oxoethyl}; 4,4′-(propane-1,3-diyl)bis{1-(2-(tetradecyloxy)-2-oxoethyl}; 4,4′-(propane-1,3-diyl)bis{1-(2-(hexadecyloxy)-2-oxoethyl} dipyridinium chlorides; 4,4′-(propane-1,3-diyl)bis{1-(2-(dodecyloxy)-2-oxoethyl}; 4,4′-(propane-1,3-diyl)bis{1-(2-(tetradecyloxy)-2-oxoethyl} and 4,4′-(propane-1,3-diyl)bis{1-(2-(hexadecyloxy)-2-oxoethyl} dipyridinium bromides. Their identifications are based on IR, 1H-NMR, 13C-NMR, DEPT, COSY and Mass spectral studies. Their surface active properties were also evaluated on the basis of surface tension and conductivity measurements.
Structure and biological behaviors of some metallo cationic surfactants
Adawy, Ahmed I.,Khowdiary, Mnal M.
, p. 709 - 715 (2013/09/02)
In this study, different cationic surfactants were prepared by esterification with bromoacetic acid of different fatty alcohols, i.e., dodecyl, tetradecyl and hexadecyl species. The products were then reacted with diphenyl amine, and the resulting tertiary amines were quaternized with benzyl chloride to produce a series of quaternary ammonium salts. The metallocationic surfactants were prepared by complexing the cationic surfactants with nickel and copper chlorides. Surface tension of these surfactants were investigated at different temperatures. The surface parameters including critical micelle concentration (CMC), maximum surface excess (Γ max), minimum surface area (A min), efficiency (PC20) and effectiveness (π CMC) were studied. The thermodynamic parameters such as the free energy of micellization (δ Gmic°) and adsorption (δ Gads°), enthalpy (δ H m°), (δ Hads°) and entropy (δ Sm), (δ Sads°) were calculated. FTIR spectra and 1H-NMR spectra were obtained to confirm the compound structures and purity. In addition, the antimicrobial activities were determined via the inhibition zone diameter of the prepared compounds, which were measured against six strains of a representative group of microorganisms. The results indicate that these metallocationic surfactants exhibit good surface properties and good biological activity on a broad spectrum of microorganisms.
Novel cationic schiff base surfactants: Surface studies and biocidal activities against bacteria fungi and sulfate reducing bacteria
Zaky,Badawi,Ead,Aboulimoud
, p. 201 - 211 (2014/04/03)
Novel series of cationic Schiff base surfactants were synthesized and characterized using microelemental analysis, FTIR and 1H-NMR spectra. The properties of the synthesized surfactant solutions such as critical micelle concentration (CMC), effectiveness (πCMC), surface excess concentration (Γmax), surface area (Amin) and free energy of micellization (δGmic) were determined using surface tension measurements. These Schiff base surfactants were evaluated for their antibacterial activity against Gram positive and Gram negative bacteria and fungi. The results of the biocidal activities revealed high potent action of the Schiff bases towards bacteria and fungi. The biocidal activity of the tested compounds against sulfur (sulfate) reducing bacteria (SRB) showed promising results in the area of oil field applications.
Synthesis, characterization and surface activity of new eco-friendly schiff bases vanillin derived cationic surfactants
Negm, Nabel A.,Kandile, Nadia G.,Mohamad, Mohamad A.
experimental part, p. 325 - 331 (2012/07/14)
Three eco-friendly cationic surface active agents were synthesized from the chemical modification of vanillin. The chemical structures of these surfactants were confirmed using elemental analysis, IR and NMR spectra. The surface activity measurements showed their high tendency towards adsorption and micellization and their good surface tension reduction, low interfacial tension. The emulsion stability measurements showed acceptable efficiency as emulsifying agents for short term emulsions. The biodegradability tests revealed that these compounds are eco-friendly and had completely degraded in 30 days. AOCS 2011.
Screening for potential antimicrobial activities of some cationic uracil biocides against wide-spreading bacterial strains
Negm, Nabel A.,Aiad, Ismail A.,Tawfik, Salah M.
experimental part, p. 503 - 511 (2012/01/14)
Eight novel uracil-based cationic surfactants containing Schiff base species were synthesized and characterized using elemental analysis, FTIR, 1H-NMR and 13C-NMR spectroscopy. The surface activities of the synthesized Schiff bases and their cationic derivatives were determined based on interfacial tension measurements and partition coefficient values in water/octanol system. The synthesized Schiff bases and their cationic derivatives were evaluated as novel biocides against different bacteria and fungi strains. The results showed that the biocidal activity of the synthesized Schiff bases was considerably increased by quaternization. The influence of the cationic surfactants as biocides was increased by increasing the hydrophobic chain length and the presence of the methoxy groups. The biocidal activity was also increased by increasing the partition coefficient inwater/octanol system.The structure and surface activity/ biocidal activity of the different compounds were discussed. AOCS 2010.
