39669-97-1Relevant articles and documents
Synthesis and surface active properties of novel carbohydrate-based cationic surfactants
Nowicki, Janusz,Sokolowski, Adam,Reksa, Dagmara
, p. 179 - 184 (2011)
The synthesis of new cationic carbohydrate surfactants is presented in this paper. The obtained surfactants have structures that are typical for saponins, which contain fatty amide hydrophobic chains and hydrophilic heads with cationic carbohydrate units. Their surface active properties and biodegradability have been studied. For two types, the biodegradability was above 85% and comparable to standard carbohydrate surfactants. AOCS 2010.
Adsorption and micellization behavior of synthesized amidoamine cationic surfactants and their biological activity
Shaban, Samy M.,Fouda,Elmorsi,Fayed,Azazy
, p. 284 - 292 (2016)
The adsorption and micellization behavior at aqueous surface of synthesized amido-amine cationic surfactants was studied using surface tension and conductometric measurements at three different temperatures of 25, 40 and 60 °C. The chemical structure of the synthesized cationic surfactants was confirmed using Fourier transform infrared and proton nuclear magnetic resonance spectroscopy. The synthetic route is simple and comprises two steps. The first is amidation between palmitic acid and dimethyl amino propyl amine, while the second step is quaternization of the first step product with different alkyl bromides. The study evaluated the effect of temperature and the hydrophobic chain length of the synthesized amidoamine cationic surfactants on the studied surface parameters. In aqueous system the adsorption tendency of the synthesized cationic surfactants is higher than micellization and both increase by increasing the hydrophobic character and the solution temperatures. The synthesized surfactants were found to have good antibiotic effect against gram positive and negative bacteria and fungi.
In-Situ Formation of Viscoelastic Wormlike Micelles in Mixtures of Non-Surface-Active Compounds
Zhang, Yongmin,Zhou, Dapeng,Feng, Yujun
, p. 189 - 198 (2015)
Viscoelastic fluids based on surfactant self-assembled wormlike micelles have been in focus over the past decade. In this work, we report wormlike micellar solutions formed in situ by simply mixing two non-surface-active compounds, N-(3-(dimethylamino)propyl)palmitamide (C16AMPM) and salicylic acid (HSal), without specialized organic synthesis of a surfactant. In the absence of HSal, C16AMPM is poorly soluble in pure water; after introducing HSal, C16AMPM is protonated into quaternary ammonium, behaving like a cationic surfactant with a low critical micellar concentration (0.25 mM) and a small area per molecule, which favors the formation of long cylindrical wormlike micelles. Above the overlapping concentration (～28 mM), the wormlike micelles formed entangle each other into viscoelastic networks, enhancing the viscosity by several orders of magnitude. In contrast to the worms formed by a single ultra-long-chain surfactant, the current system shows the advantages of a smaller flow activation energy and end-cap energy, simpler formulation and lower cost, which make it more suitable for practical use.
Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids
Agafonova, Mariya N.,Chirkova, Milana N.,Druk, Anastasia Y.,Grishaev, Denis Y.,Kayumov, Airat R.,Kazakova, Renata R.,Krylova, Elena S.,Nikishova, Tatyana V.,Nikitina, Elena V.,Sabirova, Alina E.,Sapozhnikov, Sergey V.,Shtyrlin, Nikita V.,Shtyrlin, Yurii G.
, (2021/01/06)
A diverse series of 43 novel “soft antimicrobials” based on quaternary ammonium pyridoxine derivatives which include six-membered acetals and ketals of pyridoxine bound via cleavable linker moieties (amide, ester) with a fragment of fatty carboxylic acid was designed. Nine compounds exhibited in vitro promising antibacterial activity against Gram-positive and Gram-negative bacterial strains with MIC values comparable with reference antiseptics miramistin, benzalkonium chloride and chlorohexidine. On various clinical isolates, the lead compounds 6i and 12a exhibited antibacterial activity comparable with that of benzalkonium chloride while higher than that of miramistin. Moreover, 6i and 12a were able to kill bacteria embedded into the matrix of mono- and dual species biofilms. The treatment of bacterial cells by either 6i and 12a lead to fast depolarization of the membrane suggesting that the membrane is an apparent molecular target of compounds. 6i and 12a were non mutagenic neither in SOS-chromotest nor in Ames test and non-toxic in vivo at acute oral (LD50 > 2000 mg/kg) and cutaneous administration (LD50 > 2500 mg/kg) on mice. Taken together, our data allow suggesting described active compounds as promising starting point for the new antibacterial agents development.
A high yield method for the direct amidation of long-chain fatty acids
Wang, Man-Yu,Gang, Hong-Ze,Zhou, Lei,Liu, Jin-Feng,Mu, Bo-Zhong,Yang, Shi-Zhong
, p. 99 - 108 (2019/12/12)
The amidation of long-chain fatty acids is the key step for preparing surfactants with excellent interfacial activity. Gas chromatography–mass spectrometry was employed to detect the reactants and products in the direct amidation reactions. The conversion and the concentration of the amides in the reaction process were also investigated to determine the best catalyst, the reaction rate constants, and activation energy. It was identified that the amidation reaction of the long-chain phenyl fatty acid was a zero-order reaction and 3,4,5-trifluorophenylboronic acid was the most effective catalyst by which the activation energy reduced to 55.79 kJ/mol from 95.44 kJ/mol. The method can be applied to other long-chain fatty acids, saturated or unsatureated. The turning-over-temperature was 156°C, over which high yields can be achieved without any catalyst. These provide a reference for the preparation of long-chain fatty acid amides.
A lycine amphoteric surface active agent and its preparation method
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Paragraph 0051; 0052; 0053; 0065; 0069; 0073; 0077, (2018/10/02)
The invention discloses a glycine betaine-type ampholytic surfactant and a preparation method thereof. The preparation method of the glycine betaine-type ampholytic surfactant comprises the following steps of (1) amidation reaction: carrying out amidation reaction on natural fatty acid and 3-dimethylaminopropylamine under the action of a catalyst, and timely removing water generated through reaction by using a 4A molecular sieve to obtain alkylamid-propyl dimethyl tertiary amine; and (2) quaterisation reaction: carrying out quaterisation reaction on alkylamid-propyl dimethyl tertiary amine and sodium chloroacetate in a solvent to obtain the glycine betaine-type ampholytic surfactant. The ampholytic surfactant group contains an amido bond, the performance of the molecule is changed, the glycine betaine-type ampholytic surfactant has better foam stability and mild performance, and the emulsifiability is obviously superior to that of the glycine betaine-type ampholytic surfactant. The preparation method is simple in process and low in production cost; the raw materials are green and natural; the water generated in the amidation reaction process is absorbed through the 4A molecular sieve; and the yield is improved.
Cationic anti-oxidization corrosion inhibitor and preparation method thereof
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Paragraph 0018; 0019, (2018/12/05)
The invention provides a cationic anti-oxidization corrosion inhibitor and a preparation method thereof. A structural formula of the cationic anti-oxidization corrosion inhibitor is shown in the description, wherein R is selected from one or multiple of CnH2n+1 and CnH2n-1 type aliphatic hydrocarbon chains, phenyl, methoxyphenyl, styrene, methoxystyrene, phenylpropylene and methoxyphenylpropylene;n is 6 to 22. The prepared cationic anti-oxidization corrosion inhibitor has the advantages that the environment-friendly effect is realized, and the preparation is simple; the good dissolvability isrealized in highly-mineralized stratum water and acid solutions, the good corrosion inhibition property is also realized at high temperature, and the obvious inhibition function is realized on the oxygen corrosion of carbon steel in the highly-mineralized stratum water.
N-(3-(Dimethyl benzyl ammonio)propyl)alkanamide chloride derivatives as corrosion inhibitors for mild steel in 1 M HCl solution: Experimental and theoretical investigation
Shaban, Samy M.
, p. 39784 - 39800 (2016/05/24)
The effects of N-(3-(dimethyl benzyl ammonio)propyl)lauramide chloride (DMBL), N-(3-(dimethyl benzyl ammonio)propyl)myristamide chloride (DMBM) and N-(3-(dimethyl benzyl ammonio)propyl)palmitamide chloride (DMBP) on the corrosion of mild carbon steel in acidic medium (1.0 M HCl) were investigated using weight loss and electrochemical measurements. The inhibition efficiency was found to be hydrophobicity- and temperature-dependent. Increasing the hydrophobic chain length increased the efficiency due to greater adsorption on the metal surface. The inhibition efficiency is directly proportional to the tested temperature. The electrochemical polarization study revealed that the tested cationic surfactants are mixed-type inhibitors. The Villamil adsorption isotherm is the better-fitted model for describing the adsorption process on the selected steel in 1.0 M HCl medium. The change in the free energy of adsorption of the synthesized cationic surfactants on the metal surface indicates that the adsorption process is chemisorption. Double-layer capacitance values obtained from electrochemical impedance spectroscopy decrease in the presence of the synthesized surfactant. Quantum chemical calculations support the experimental data and the adsorption on the metal surface.
Surface Parameters and Biological Activity of N-(3-(Dimethyl Benzyl Ammonio) Propyl) Alkanamide Chloride Cationic Surfactants
Shaban, Samy M.,Aiad, Ismail,Ismail, Abdallah R.
, p. 501 - 510 (2016/05/02)
Three cationic surfactants containing amide groups were prepared by quaternization of dimethylaminopropylamine with benzyl chloride. FTIR and 1H-NMR spectroscopy were used to confirm the chemical structure of the prepared cationic surfactants. The surface parameters were estimated using surface tension measurements at three different temperatures. The prepared cationic surfactant showed a lower CMC than conventional cationic surfactants. Thermodynamic parameters of adsorption and micellization depend mainly of alkyl chain length and temperature. The adsorption process is more favorable than micellization. The biological activity of the three surfactants was estimated using inhibition zone showing that amidoamine cationic surfactants have good activity and the surfactants C12Bn is the most effective one.
Amidoamine Gemini surfactants based dimethylamino propyl amine: Preparation, characterization and evaluation as biocide
Shaban, Samy M.,Aiad,Moustafa,Hamed, Ahmed
, p. 907 - 914 (2015/11/16)
The chemical structures of three prepared amidoamine Gemini surfactant were confirmed using FTIR and 1HNMR spectroscopic methods. The synthetic routes passed through two steps, the first one is the formation of the amide and the second one is the quaternization of the prepared amide with dibromo propane. The surface and thermodynamic parameters were determined from surface tension and conductivity measurements. The obtained critical micelle concentrations from both techniques are similar. The values of CMC were found to depend on both solution temperature and hydrophobic character. The change in free energy of micellization and adsorption showed a tendency of synthesized Gemini surfactants to adsorb at the interface first then forming micelle in the bulk. The prepared Gemini surfactants act as good antibiotic against some tested bacteria and fungi.
