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1.
In the present work, a two-step method was adopted to synthesize a series of novel Gemini surfactants using N,N-dimethylalkyl amines (alkyl length = C12, C16 and C18), epichlorohydrin, and n-phenyllenediamine as starting materials. The products were characterized using mass spectroscopy (MS) and nuclear magnetic resonance spectroscopy (1H NMR). Systematic experiments were conducted to evaluate their surface activity, foaming properties, and antibacterial performance. Results showed the critical micelle concentrations (CMC) of the C12-based, C16-based, and C18-based phenylenediamine surfactants were 3.295 × 10−3, 2.532 × 10−4, and 3.140 × 10−4 mol L−1 at 298 K, respectively, with corresponding surface tension (γcmc) values of 28.24, 31.95, and 35.06 mN m−1 under the same conditions. The Gemini surfactants showed not only good surface activity and foaming properties, but also demonstrated good antimicrobial performance against Gram-positive and Gram-negative bacteria and fungi. 相似文献
2.
Preparation,Characterization and Properties of Novel Cationic Gemini Surfactants with Rigid Amido Spacer Groups 下载免费PDF全文
Dongqing Xu Banghua Qi Di Fang Xuemei Zhang Ting Zhang 《Journal of surfactants and detergents》2016,19(1):91-99
A series of novel cationic gemini surfactants with rigid amido groups inserted as the spacers, named C 12 ‐PPDA‐C 12 , C 14 ‐PPDA‐C 14 and C 16 ‐PPDA‐C 16 , were synthesized by a two‐step reaction with dimethyl terephthalate, N,N‐dimethyl propylene diamine and alkyl bromide as raw materials. The chemical structures of the prepared compounds were confirmed by IR, 1H and 13C NMR and element analysis. Surface activity properties of the synthesized compounds were investigated by surface tension, electrical conductivity and fluorescence. Increasing the number of carbon atoms in the hydrophobic alkyl chain, decreased the critical micelle concentration (CMC), surface tension at the CMC and the minimum surface area. Other relevant properties including foaming ability and emulsion stability were investigated. The results indicated that the synthesized gemini surfactants possess good surface properties, emulsifying properties and steady foam properties. 相似文献
3.
Preparation,Surface-Active Properties and Antimicrobial Activities of Bis(Ester Quaternary Ammonium) Salts 总被引:3,自引:0,他引:3
Joanna Węgrzyńska Jan Chlebicki Irena Maliszewska 《Journal of surfactants and detergents》2007,10(2):109-116
New cationic surfactants, bis-quaternary ammonium salts, were prepared from N,N-dimethylaminoalkyl esters of saturated fatty acids and products of the reactions of epichlorohydrin with primary amines:
pentyl-, hexyl- and octylamine. The bis (ester–ammonium) salts obtained were examined in respect to their surface-active properties:
critical micelle concentration (CMC), effectiveness of surface tension reduction (γCMC), and adsorption efficiency (pC20). All these surfactants showed good water solubility and low critical micelle concentrations of more than two orders of magnitude
lower than these of corresponding mono-alkylammonium salts. They also showed good wetting capability, but worse foaming properties.
All the surfactants tested were nontoxic to gram-negative bacteria, but some of them inhibited the growth of gram-positive
bacteria and yeast.
相似文献
Jan ChlebickiEmail: |
4.
Shuichi Matsumura Yasushi Kawamura Sadao Yoshikawa Kazuo Kawada Tsuyoshi Uchibori 《Journal of the American Oil Chemists' Society》1993,70(1):17-22
Three series of D-glucosamine derivatives containing an alkyl chain with 8 to 14 atoms, methyl 2-acylamino-2-deoxy-D-glucopyranosides,n-alkyl 2-acetylamino-2-deoxy-D-glucopyranosides andn-alkyl 2-amino-2-deoxy-D-glucopyranoside hydrochlorides, were synthesized, and their surface properties (such as surface tension,
critical micelle concentration (CMC), dynamic surface tension and foaming properties), biodegradability and antimicrobial
activities were evaluated.n-Alkyl 2-amino-2-deoxy-D-glucopyranoside hydrochlorides containing C8 to C12 carbon chains showed surface activities, a CMC
and excellent foaming properties. The α-anomers showed a slightly lower CMC than the β-anomers, indicating less hydrophilicity
of the α-anomers. On the other hand, glucosamine derivatives containing amide groups showed poor surface activities in water
due to their lower solubilities in water. All glucosamine derivatives containing alkyl chains were biodegraded as well as
conventional ethoxylated nonionics by activated sludge from the municipal sewage treatment plant. Methyl 2-acylamino-2-deoxy-D-glucopyranosides
andn-alkyl 2-amino-2-deoxy-D-glucopyranoside hydrochlorides showed a broader spectrum of antimicrobial activity than the correspondingn-alkyl glucopyranosides. Among them the C12 derivatives showed the best results. 相似文献
5.
Surface activities,biodegradability and antimicrobial properties of n-alkyl glucosides,mannosides and galactosides 总被引:1,自引:0,他引:1
Shuichi Matsumura Kazuyasu Imai Sadao Yoshikawa Kazuo Kawada Tsuyoshi Uchibor 《Journal of the American Oil Chemists' Society》1990,67(12):996-1001
n-Alkyl α-and β-glucopyranosides, α-D-mannopyranosides and β-D-galactopyranosides with alkyl chains having from 8 to 12 carbon
atoms were synthesized and their surface properties-such as static surface tension (γ), critical micelle concentration (CMC),
occupation area of molecule, dynamic surface tension and foaming properties, biodegradability and antimicrobial activities—were
evaluated. Alkyl glycosides containing C8 to C12 carbon chains showed surface activities and critical micelle concentrations.
D-Glucoside, D-mannoside and D-galactoside having the same alkyl chain showed similar surface tension lowering at CMC (γCMC) and occupation area of the molecule at the surface. Among the alkyl glucosides, α-anomers were less hydrophilic than β-anomers.
All alkyl glycosides tested in this study were readily biodegraded by activated sludge of a municipal sewage plant compared
to those of ethoxylated nonionic alcohols. The difference of the hydrophilic glycopyranoside group in biodegradability was
not seen clearly. n-Alkyl glycosides containing C8 to C12 alkyl chains showed a broad spectrum of increasing antimicrobial
activity. n-Dodecyl α-D-mannopyranoside was the most effective, the order of antimicrobial activity being mannopyranoside
> glucopyranoside > galactopyranoside group. Members of this class of compounds exhibit the physicochemical and biological
properties needed both for a wide range of applications and for environmental acceptance. 相似文献
6.
S. Y. Mhaskar G. Lakshminarayana L. Saisree 《Journal of the American Oil Chemists' Society》1993,70(1):23-27
The effect of structural variation in the fatty acid chain on the antibacterial activity ofN-acyl-L-leucines was investigated. PureN-acyl leucines of some structurally different and biologically active uncommon fatty acids were synthesized for the first
time and tested for antimicrobial activity.N-Stearoyl-,N-oleoyl- andN-ricinoleoyl leucines were also evaluated for comparison. TheN-acyl leucines exhibited greater activity in acid form than the methyl ester form and against gram positive bacteria than
gram-negative bacteria. The presence of a cyclopropane or a hydroxy group or unsaturation in the acyl chain increased the
antibacterial activity. Shifting the hydroxyl group toward the amide linkage resulted in a diminished effect on the antibacterial
activity. 相似文献
7.
Preparation,surface-active properties,and antimicrobial activities of bis-quaternary ammonium salts from amines and epichlorohydrin 总被引:1,自引:1,他引:1
A series of new cationic surfactants, bis-quaternary ammonium salts, were prepared from tert-alkylamine and a product of the reaction of epichlorohydrin with decyl- and dodecylamine, and their surface-active properties
were measured. Specifically, the critical micelle concentration (CMC), effectiveness of surface tension reduction (γCMC), surface excess concentration (Γ), area per molecule at the interface (A), and standard free energies of adsorption (ΔG
ads
o) and of micellization (ΔG
mic
o) were determined. All these surfactants showed good water solubility and low CMC, more than one order of magnitude lower
than those of corresponding mono-alkylammonium salts. They also showed good foaming properties but worse wetting capabilities.
Many of these compounds had antimicrobial activities against gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis) and yeast (Candida albicans), but they were not active against molds. 相似文献
8.
Synthesis,Surface-Active Properties,and Antimicrobial Activities of New Neutral and Cationic Trimeric Surfactants 总被引:3,自引:1,他引:2
Marcelo C. Murguía Mariano D. Cristaldi Ayelén Porto José Di Conza Ricardo J. Grau 《Journal of surfactants and detergents》2008,11(1):41-48
Neutral and cationic series of new trimeric β-hydroxy amino or ammonium surfactants were synthesized via a two-step process
involving the Williamson etherification and regioselective oxirane ring opening with primary and tertiary amines, which afforded
good to excellent yields. The synthesized compounds were obtained in high purity by a simple purification procedure on column
chromatography. The critical micelle concentration (CMC), effectiveness of surface tension reduction (γ
CMC), surface excess concentration (Γ), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation
properties. The antimicrobial activities are reported for the first time against representative bacteria and fungi for trimeric
compounds. The antimicrobial potency was found to be dependent on the target microorganism (Gram-positive bacteria > fungi > Gram-negative
bacteria), as well as both the neutral or ionic nature (cationic > neutral) and alkyl chain length (tri-C12 > tri-C18 > tri-C8) of the compounds. The tri-C8 and tri-C18 compounds were found to be almost inactive and the tri-C12 compounds, the most potent antimicrobial surface-active agents from the synthesized series. The trimeric C12 cationic compound was found to be comparable to benzalkonium chloride against Gram-positive bacteria and fungi, in vitro.
The antimicrobial effectiveness of this new compound and the facile two-step procedure for synthesizing it with an excellent
overall yield (92%) provide a cost effective trimeric gemini surfactant.
相似文献
Ricardo J. GrauEmail: |
9.
Caroline Rondel Isabelle Alric Zéphirin Mouloungui Jean-François Blanco Françoise Silvestre 《Journal of surfactants and detergents》2009,12(3):269-275
The acylation of amino acids by acid chlorides with from 8 to 12 carbon atoms in alkaline aqueous medium following Schotten–Baumann reaction results in sodium salts of a N α-acylamino acid and fatty acid mixture. The latter are present in a proportion from 40 to 60%. These compositions represent mixtures of amphiphilic anionic surfactants. Together they contribute to the properties of the formulation. Measurements of the surface-active properties of these formulations, such as critical micelle concentration (CMC), surface tension at the CMC (ST), foaming capacity (FC) and foaming stability (FS), show that surfactant mixtures with the longest chain have the most desirable properties. They are comparable to commercial petroleum-based surfactants. Thus, the CMC, ST and CM values of the formulation obtained starting from leucine and dodecanoyl chloride (310 mg/l, 30.1 mN/m and 200%, respectively) are similar to, and even better than, sodium dodecylsulfate (290 mg/l, 39.1 mN/m and 230%, respectively). 相似文献
10.
Hans-Josef Altenbach Rachid Ihizane Bernd Jakob Karsten Lange Manfred Schneider Zeynep Yilmaz Sukhendu Nandi 《Journal of surfactants and detergents》2010,13(4):399-407
The reaction of hydroxycarboxylic acids, such as citric, malic and tartaric species with an excess of fatty acid chlorides
produces the corresponding O-acylated hydroxycarboxylic anhydrides in one step and in a near quantitative yield. These molecules are excellent electrophiles
which react readily with a variety of nucleophiles including alcohols, diols and polyols. Their reaction with triethylene
glycol and triethylene glycol monomethyl ether leads to two series of novel anionic surfactants, which are unsymmetrical gemini
surfactants. The determination of their properties (CMC, foaming, HLB) revealed that these molecules are—depending on the
chain length of the fatty acid—excellent emulsifiers, and that they also display interesting antimicrobial activity. These
novel functional surfactants are of interest for applications in food and personal care products and for the formulation of
pharmaceuticals. 相似文献
11.
J. Molinero M. R. Julia P. Erra M. Robert M. R. Infante 《Journal of the American Oil Chemists' Society》1988,65(6):975-978
In order to obtain protein-based amphoteric surfactants with antimicrobial properties, N
α
-lauroyl arginine dipeptides have been prepared by condensation between N
α
-lauroyl arginine and amino acids which come from a collagen hydrolysate. Some surfactant properties and the minimum inhibitory
concentration against Gram positive and Gram negative bacteria have been evaluated. All types of compounds presented a surfactant-like
behavior. Furthermore, the compounds described in this paper may be considered as mild preservative or protective substances. 相似文献
12.
In this paper, the second part of a systematic study whose aim deals with the influence of the terminal amino acid side chain
on the properties of Nα-lauroyl arginyl dipeptides is reported. Nα-lauroyl arginyl dipeptides that contain an acidic amino
acid (glutamic acid) or a basic amino acid (lysine) as terminal amino acid have been prepared by peptide synthesis methods.
These compounds have been synthesized as methyl esters (cationic surfactants) and free α-carboxylic acids (amphoteric surfactants),
and their fundamental surfactant properties and antimicrobial activity have been evaluated. The properties of these compounds
have been compared to the properties of the cationic monomer derivative methyl ester of Nα-lauroyl arginine and of the amphoteric
monomer derivative Nα-lauroyl arginine reported earlier.
The compounds are soluble in water and show surface activity, although in the case of the amphoteric Nα-lauroyl arginyl dipeptide
containing glutamic acid these two properties depend on the solution pH. The cationic Nα-lauroyl arginyl dipeptides are antimicrobial
agents. However, only the amphoteric compound containing lysine may be considered antimicrobial. 相似文献
13.
Synthesis and Characterization of Cationic Surfactants Based on N‐Hexamethylenetetramine as Active Microfouling Agents 下载免费PDF全文
Rafat M. Mohareb Abdelfatah M. Badawi Mahmoud R. Noor El‐Din Nesreen A. Fatthalah Marian R. Mahrous 《Journal of surfactants and detergents》2015,18(3):529-535
Four cationic surfactants of quaternary hexammonium silane chloride based on hexamethylenetetramine and alkyl chloride were synthesized. The chemical structures of the prepared cationic surfactants were elucidated using Fourier transform infrared (FT‐IR) spectroscopy and mass spectrometry analysis. The surface and thermodynamic properties of the prepared surfactants were also studied. The performance of these cationic surfactants as microfouling agents against two strains of Gram‐negative bacteria, namely, Pseudomonas aeruginosa and Escherichia coli, and two strains of Gram‐positive bacteria, namely, Staphylococcus aureus and Bacillus subtilis, were evaluated as antimicrobial agents. The results showed that the maximum antimicrobial activity was detected for N‐hexamethylenetetramine‐N‐ethyl silane ammonium trichloride (Ah). The maximum and minimum antimicrobial activities were 73 and 60 % against S. aureus and E. coli, respectively, at a concentration of 5 mg/l, pH 7, and 37 °C. 相似文献
14.
Symmetrical gemini surfactants of cationic series α,ω-alkanediyl bis (dimethyl ammonium bromide) commonly referred as “m–s–m” have been synthesized. Spectral analysis was performed to confirm compound structures and purity. Conductivity and surface
tension measurements provide better understanding of the micellization process. Their self-assembly behavior in aqueous solution
is also discussed in detail. The antimicrobial efficacy was measured by bacterial and fungal growth inhibition expressed as
minimal inhibitory concentration values against five strains of a representative group of microorganisms viz. Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumonia, Salmonella paratyphi B and Aspergillus niger. All of the synthesized surfactants showed antimicrobial activity against them, but at different levels depending on their
structures. The surfactants possessing longer alkyl chains (more hydrophobic environment) demonstrated better antimicrobial
functionality. The antimicrobial potency was found to be dependent on the representative target microorganism (Gram-positive
bacteria > fungi > Gram-negative bacteria), as well as on the ionic nature of the surfactant (cationic), alkyl chain length
(m = 12, 16) and spacer length (s = 2, 4, 6) of the synthesized compounds. Gemini surfactants such as 12-2-12 and 12-4-12 were found to be weakly active whereas
16-2-16 and 16-4-16 compounds proved to be the most potent antimicrobial surface-active agents among the synthesized gemini
homologues. 相似文献
15.
Xianyou He Liyan Wang Jianglei Wu Jia Yang Wenhui Ma Liming Bai Bing Zhao Bo Song 《Journal of surfactants and detergents》2019,22(2):315-325
The cationic surfactants containing aromatic rings and amide bonds, N,N-dimethyl-N-dodecyl-2-pyrimidinylcarbamoylmethyl ammonium chloride ( a ), N,N-dimethyl-N-dodecyl-2-thiazolylcarbamoylmethyl ammonium chloride ( b ), and N,N-dimethyl-N-dodecyl-phenylcarbamoylmethyl ammonium chloride ( c ), were synthesized and characterized. The surface tension and conductivity values were employed to investigate the absorption and micellization behavior of the three cationic surfactants. The results showed that the synthesized surfactants have shown a low critical micelle concentration (CMC) and a high adsorption efficiency (pC20) compared with the traditional cationic surfactant of N,N-dimethyl-N-dodecyl-N-benzyl ammonium chloride ( BAC-12 ). The aromatic rings of the a , b , and c molecular structures were analyzed using the 1H NMR spectra for electrostatic repulsion effects between hydrophilic headgroups. The size distribution of the micelles was derived using dynamic light scattering (DLS) techniques. In addition, the foaming ability of a , b , c , and BAC-12 was investigated and the antimicrobial activity of a , b , c , and BAC-12 against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis was examined. The effects of amide bonds and aromatic rings on the surface properties and antimicrobial activity of a , b , and c were analyzed and compared with BAC-12 of the same alkyl chain length. The synthesized surfactants exhibited a high surface ability and better antibacterial activity compared with BAC-12 . 相似文献
16.
Jianwei Zhang Kun Huang Xuetong Fan Gary D. Strahan Alberto Nuńez Majher I. Sarker Helen Ngo 《European Journal of Lipid Science and Technology》2023,125(11):2300012
Typically, short- and long-chain lipids from oils exhibit different antimicrobial activities and therefore have been used in agriculture and aquaculture, biomedical therapeutic and antibacterial fields. However, these fatty acids have limitations in terms of bioactive efficacy, thermostability and aqueous solubility. In this study, water-soluble iso-fatty acid arginate hydrochloride derivatives with antimicrobial properties were produced by introducing branched (iso-) chain and other linear- (n-) chain fatty acids to the “arginine” amino acid molecule. The two-step synthetic route was straightforward and provided an efficient 88% and 76% product yields for ethyl n-oleoyl arginate hydrochloride and ethyl iso-oleoyl arginate hydrochloride, respectively. ATR-FT-IR, NMR, and LC-MS-Q-TOF techniques were used to thoroughly characterize and confirm the products. These arginate products had strong antimicrobial activities against Listeria innucua, a Gram-positive bacterium with minimum inhibitory concentrations and minimum bactericidal concentrations ranging from 1.8 µg mL−1 to 29.1 µg mL−1. Therefore, the study demonstrated the development of a novel class of antimicrobial compounds from iso-fatty acids and arginates. 相似文献
17.
Quaternized carboxymethyl chitosan (QCMC) was prepared from which carboxymethyl chitosan (CMC) was prepared from chitosan first, then N-quaternary ammonium group was introduced by the reaction of CMC with 2, 3-epoxypropyl trimethylammonium. The structures of the derivatives were characterized by FT-IR, XRD, 13C NMR, 1H NMR and gel permeation chromatography. In vitro antimicrobial activities of QCMC were evaluated against Escherichia coli, which is a Gram-negative bacterium, and Staphylococcus aureus, which is a Gram-positive bacterium. In compared with carboxymethyl chitosan (CMC) and quarternary chitosan (QC) of the same degree of substitusion (DS), we found that QCMC has stronger antimicrobial activity. Then we went deep into study of the relationship between their structure and antimicrobial activity, found that the DS of CMC do little effect to their antimicrobial activity, but as the increase of their DS of quaternization or the decrease of their molecular weight, the antimicrobial activity of QCMC become stronger. QCMC was complexed with calcium hydroxide as pulp-cap. Animal experiment results indicated that QCMC can strongly induce reparative dentine formation and showed a better ability in dentin inducing compared with calcium hydroxide. 相似文献
18.
Ping Zeng Chen Xu Qipeng Cheng Jun Liu Wei Gao Xuemei Yang Prof. Kwok-Yin Wong Prof. Sheng Chen Dr. Kin-Fai Chan 《ChemMedChem》2019,14(16):1547-1559
Phenol-soluble modulins (PSMs) are a large family of cytolytic peptide toxins produced by Staphylococcus aureus. Based on their amino acid sequences, we have constructed a small library of cationic isoleucine-rich peptides for antimicrobial evaluation. Relative to the parent PSMs, peptide zp3 (GIIAGIIIKIKK-NH2) was found to possess greatly improved physicochemical properties (soluble in water) and antibacterial activity (MIC=8 μm for E. coli, B. subtilis, and C. freundii) while maintaining low hemolytic activity (<5 % at 256 μm ) and cytotoxicity (HEK293 cells IC50>80 μm ). We reasoned that the selective activity of zp3 toward bacterial cells is due to its amphiphilic nature and positive net charge. Moreover, it is difficult for bacteria to develop resistance against zp3 . Through microscopic studies of E. coli, we demonstrated that zp3 can penetrate the bacterial membrane, thereby causing leakage of the bacterial cytoplasm. Our findings present a promising antimicrobial peptide lead, which has great potential for further chemical modification. 相似文献
19.
Over 40 natural or synthetic lipophilic compounds were screened for antimicrobial activity. Gram (+) bacteria and yeasts but
not Gram (−) bacteria were affected by these agents. Epimino and selena fatty acids are more active than their corresponding
straight chain unsubstituted fatty acids. The position of selenium influenced the antimicrobial activity of the fatty acid.
The presence and position of a double or triple bond, usually an important factor in long chain fatty acids (>C14) had little or no effect in C11 fatty acids. Optimum antimicrobial activity was found for fatty acids and their corresponding monoglycerides when the chain
length was C12. The dilaurin derivative was not active. 相似文献
20.
Sanjit Kanjilal Kaki Shiva Shanker Kotte Sagar Rao Kunduru Konda Reddy Bhamidipati V. S. K. Rao Kota B. Shiva Kumar Mannepalli L. Kantam Rachapudi B. N. Prasad 《European Journal of Lipid Science and Technology》2008,110(12):1175-1182
An efficient chemo‐enzymatic synthesis of ferulic acid‐based structured lipids mimicking triacylglycerol with a pendant phenolic moiety was carried out for the first time. Initially, ferulic acid was reduced to coniferyl alcohol, followed by its esterification with fatty acids. The key step in the synthesis was dihydroxylation of the olefinic side chain of coniferyl ester, which was eventually esterified with fatty acids to generate phenolic structured lipids. Two such compounds of varying fatty acid chain lengths were synthesized in good yield. Structural confirmation of both compounds is based on IR, 1H and 13C NMR, and MS techniques. The synthesized compounds were tested for in vitro antioxidant and antimicrobial activities. Both compounds exhibited moderate to good antioxidant activity. The phenolic structured lipid with only shorter‐chain fatty acids showed antibacterial activity. Both compounds did not show any antifungal activity. 相似文献