3179-80-4Relevant academic research and scientific papers
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)
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.
METHOD FOR PREPARING A FATTY AMIDOALKYLDIALKYLAMINE
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Page/Page column 7-8, (2021/12/08)
The present invent ion concerns a method for preparing a fatty amidoalkyldialkylamine by reacting a fatty acid with a dialkylaminoalkylamine, using a molar ratio of said dialkylaminoalkylamine to said fatty acid of more than 1 and up to 1.5, in the presence of Candida antarctica lipase as catalyst.
The surface properties of amine oxides with a fluoroether chain
Chen, Qing-Yun,Dai, Longhao,Guo, Yong,Huang, Meiwei,Shen, Qing,Su, Qin,Su, Zhaoben,Wu, Chengying,Zhao, Zhi-Gang
, (2021/06/12)
Persistent organic pollutants (POPs) includes long-chained fluorosurfactants, for instance, perfluorooctanonate (PFOA) and perfluorooctanesulfonate (PFOS). In order to find out alternative fluorosurfactants, we synthesized eight amine oxides with a fluoroether chain. Their surface properties were evaluated and compared with perfluoroalkyl and hydrocarbon analogues. The surface tensions at critical micelle concentration (γcmc) for the eight amine oxides with a fluoroether chain were at a range from 15.5 to 23.0 mN/m, and γcmc of four fluoroether amine oxides were below 17 mN/m comparable to perfluorooctyl analogues (16.4 mN/m) and much lower than perfluorohexyl (20.5 mN/m) and hydrocarbon analogues (24.2 and 24.7 mN/m). The critical micelle concentration (cmc) for the eight amine oxides with a fluoroether chain were 3 to 535 × 10?4 mol/L. The cmc of four fluoroether amine oxides were 3 to 21 × 10?4 mol/L (0.2 to 1.0 g/L) comparable to perfluorooctyl (0.4 g/L) and hydrocarbon analogues (4 and 10 × 10?4 mol/L) and much lower than perfluorohexyl analogue (36.9 g/L). The surface excesses, the limiting molecule areas and the free energies of micellization of amine oxides were calculated. Fluoroether surfactants are promising alternatives for PFOA and PFOS.
Novel quaternary ammonium salt compound, and preparation method and applications thereof
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Paragraph 0030-0032, (2019/10/01)
The invention provides a novel degradable quaternary ammonium salt compound, and a preparation method and applications thereof. The novel degradable quaternary ammonium salt compound is prepared through following steps: a C8-C11 alkyl carboxylic acid, a cycloalkyl carboxylic acid, and a substituted alcohol and a substituted primary amine are subjected to condensation in the presence of a condensing agent to generate an ester; the ester, an amide, and epoxy chloropropane are reacted to obtain a single quaternary ammonium salt; the single quaternary ammonium salt, an ester, and an amide are subjected to ring opening reaction to obtain a biquaternary ammonium salt; and the biquaternary ammonium salt is subjected to reaction with a substituted alkyl silicon in the presence of a catalyst so as to obtain the novel degradable quaternary ammonium salt compound. The novel degradable quaternary ammonium salt compound possesses excellent water solubility, biological degradability, and sterilizing performance; the preparation method is simple; and industrialized applications are convenient to realize.
Preparing method for fatty acid amide propyl tertiary amine
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Paragraph 0004; 0034; 0035; 0036; 0037-0054; 0067-0069, (2017/05/26)
The invention relates to a preparing method for fatty acid amide propyl tertiary amine. Preparation is carried out with pipeline reactors and devolatiligation equipment. The preparing method comprises the following steps that fatty acid, an N,N'-Dimethyl-1,3-propyldiamine aqueous solution and a catalyst are mixed and then enter the first pipeline reactor for a reaction; then a reaction product is put into a first devolatiligation kettle, and low-boiling-point substances are removed; then, the product obtained after devolatiligation is mixed with a small amount of pure N,N'-dimethyl-1,3-propyldiamine and then enters the second pipeline reactor for a reaction; finally, the product is put into a second devolatiligation kettle, low-boiling-point substances are removed, and fatty acid amide propyl tertiary amine is obtained. According to the preparing method, the pipeline reactors and a two-step method are adopted for synthesizing fatty acid amide, the synthesizing efficiency is greatly improved, the synthesizing time can be shortened to be 4 h or shorter, the conversion rate of fatty acid can reach 98% or above, and energy consumption is greatly reduced; besides, the preparing method is convenient to control and safe, and continuous mass production can be achieved.
Synthesis and Evaluation of Novel Amido-Amine Cationic Gemini Surfactants Containing Flexible and Rigid Spacers
Hussain, S. M. Shakil,Kamal, Muhammad Shahzad,El Ali, Bassam,Sultan, Abdullah S.
, p. 777 - 788 (2017/07/05)
New amido-amine-based cationic gemini surfactants with flexible and rigid spacers and different hydrophobic tails were synthesized and characterized. These gemini surfactants were prepared by a modified procedure through amidation of long chain carboxylic acids using 3-(dimethylamino)-1-propylamine followed by treatment with halohydrocarbons. The effect of the trans and cis conformation of the spacer double bond was investigated by means of critical micelle concentration, surface tension reduction, and thermal stability. The short-term thermal stability of the gemini surfactants was assessed using thermogravimetric analysis (TGA) and the long-term thermal stability was examined by a unique approach based on structure characterization techniques including NMR (1H and 13C) and FTIR analysis. TGA results demonstrated excellent short-term thermal stability since no structure degradation was observed up to 200?°C. Structural characterization revealed impressive long-term thermal stability of the gemini surfactants with no structure decomposition after exposing them to 90?°C for 10?days. The critical micelle concentration of gemini surfactants was found to be in the range of 0.77?×?10?4–3.61?×?10?4?mol?L?1 and corresponding surface tension (γCMC) ranged from 30.34 to 38.12?mN?m?1. The surfactant with the trans conformation of spacer double bond showed better surface properties compared to the surfactant with the cis conformation of spacer double bond. Similarly, increasing surfactant tail length and spacer length resulted in decreasing CMC values. Moreover, bromide counterion showed improved surface properties compared to chloride counterion.
A method for reducing betaine free acid in the process method of the (by machine translation)
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Paragraph 0024; 0025; 0026; 0041-0042, (2017/11/08)
This invention discloses a method for reducing free acid betaine in the process, firstly on the fatty acid with a batch of reaction distilled N, N - dimethyl - 1, 3 - propanediamines waste liquid reaction, then in the system by adding pure N, N - dimethyl - 1, 3 - propylene diamine reaction, to obtain the intermediate alkyl amide propyl dimethylamine, then the alkyl amide propyl dimethylamine and chloroethyl acid reaction, to prepare amide propyl betaine, reduces the betaine in the free acid. Compared with the prior art, the present invention through improved technology, the repeated use of reflux, the raw material is improved N, N - dimethyl - 1, 3 - propanediamines utilization rate, through the added raw materials under high temperature conditions N, N - dimethyl - 1, 3 - propylene diamine, reflux circulating reflux use, not only promote the condensation reaction degree, reduce the consumption of the raw materials, so that the content of free acid in the product is reduced, improving the product quality, and reduce environmental pollution, and improves the economic problem of cost-effectiveness, favorable to commercial production. (by machine translation)
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.
Fatty acid amide propyl betaine foam scrubbing agent as well as preparation method and application thereof
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Paragraph 0032; 0033, (2016/10/17)
The invention relates to a foaming agent developed for foam drainage of a gas well, in particular to a fatty acid amide propyl betaine foam scrubbing agent as well as a preparation method and an application thereof. The fatty acid amide propyl betaine foam scrubbing agent is adaptable to the highly-mineralized and high-oil-bearing extreme environment with the mineralization degree higher than 25*10 mg/L and the content of condensate oil higher than 30%. According to the technical scheme, lauric acid, coconut fatty acid, oleic acid (cis-9-octadecenoic acid) and other fatty acids are added to a reactor in a certain mole ratio and have a condensation reaction with N,N-dimethyl-1,3-propane diamine at the temperature of 140-160 DEG C for 3-4 h, and an intermediate product, namely, long-chain alkyl tertiary amine, is obtained; the intermediate product and sodium chloroacetate have a nucleophilic substitution reaction at the temperature of 60-90 DEG C for 3-6 h, the content of free amine is tested to be smaller than 0.5%, fatty acid amide propyl betaine is obtained after the reaction, and fatty acid amide propyl betaine is a main agent of the foam scrubbing agent for the gas well. The prepared foam scrubbing agent has good foaming and foam stabilizing performance, foams carry a large quantity of liquids, and the foam scrubbing agent has excellent foam flooding performance in various extreme environments and has wide prospect.
