- The surface properties of amine oxides with a fluoroether chain
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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.
- Chen, Qing-Yun,Dai, Longhao,Guo, Yong,Huang, Meiwei,Shen, Qing,Su, Qin,Su, Zhaoben,Wu, Chengying,Zhao, Zhi-Gang
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- Synthesis, Characterization, and Viscosification of Amidosulfobutaine and Zwitterionic Gemini Surfactants
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The viscoelastic surfactants (VES)-based acid diverters are frequently used to divert acid flow from high-permeability layers into low-permeability for enhanced overall productivity of the treated well. In general, an optimum VES-based system possesses advantages of decrease in absorption loss, damage of reservoir, and improved adaptability of active agents to high salinity. Herein, we report the synthesis of three new zwitterionic gemini surfactants (1–3) and previously known amidosulfobutaine (C18AMP3SB) has been accomplished for the investigation of diverting acid performance. The synthesis of these surfactants was achieved by the amidation of the acid chlorides of commercially available fatty acids with 3-(dimethylamino)-1-propylamine followed by subsequent reactions with appropriate sultone or ethyl 4-bromobutanoate. The synthesized surfactants were well characterized by spectroscopic methods including IR and NMR spectroscopy. The thermogravimetric analysis (TGA) results suggested that surfactants (1–3) and C18AMP3SB possess excellent thermal stability, with no appreciable loss of mass up to 300°C. The viscosity measurements of the neat surfactants (1–3) and C18AMP3SB were performed under various temperatures, in the presence of different concentration of calcium chloride salt with the aid shear viscosimetry. The analysis revealed that the viscosity of neat C18AMP3SB increases with increase in concentration of CaCl2. With 10% CaCl2 solution, the viscosity was increased from 7.5 to 33.55 cPs, whereas in 20% CaCl2 the viscosity reached to 102 cPs with rise in temperature from ambient to 90°C. Moreover, the viscosity of neat surfactants (1–3) did not exhibit any appreciable viscosity change under the experimental conditions. However, the mixture of surfactants (1–3) each in combination with C18AMP3SB (1:1) displayed significant upsurge in the viscosity, up to more than 10 folds.
- Mansha, Muhammad,Ullah, Nisar,Kalgaonkar, Rajendra A.,Baqader, Nour
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p. 697 - 706
(2020/12/01)
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- CATIONIC LATEX EMULSION INCLUDING DIQUATERNARY AMMONIUM SURFACTANT
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Various aspects of the present invention relate to cationic latex emulsions, methods of making the same, various materials including the cationic latex emulsion such as asphalt emulsions, and methods of making the asphalt emulsions. A cationic latex emulsion includes latex particles. The cationic latex emulsion includes an aqueous liquid emulsified with the latex particles. The cationic latex emulsion also includes a cationic surfactant that is a diquaternary ammonium surfactant.
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Paragraph 00096; 00099
(2021/08/13)
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- METHOD FOR PREPARING A FATTY AMIDOALKYLDIALKYLAMINE
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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.
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Page/Page column 9-10
(2021/12/08)
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- Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids
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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.
- 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.
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- A high yield method for the direct amidation of long-chain fatty acids
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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.
- Wang, Man-Yu,Gang, Hong-Ze,Zhou, Lei,Liu, Jin-Feng,Mu, Bo-Zhong,Yang, Shi-Zhong
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- Method for preparing fatty acid amide dimethyl tertiary amine compounds from solid superbase
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The invention discloses a method for preparing fatty acid amide dimethyl tertiary amine compounds from solid superbase, and belongs to the field of organic chemical synthesis. According to the method,one or several kinds of fatty acids and N,N-dimethylamino compounds are used as raw materials; solid superbase with the advantages of high catalysis activity, cyclic use and environment-friendly effect is used as a catalyst for preparing the fatty acid amide dimethyl tertiary amine compounds. The method has the advantages that the operation is simple and convenient; the post treatment is simple;the reaction conditions are mild; the yield is high; the method belongs to a green novel method for synthesizing the fatty acid amide dimethyl tertiary amine compounds.
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Paragraph 0015-0016
(2018/03/01)
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- HAIR TREATMENT AGENT
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PROBLEM TO BE SOLVED: To provide a hair treatment agent that can impart, even to damaged hair, excellent finger's running through properties, smoothness, and a coat feeling, both under wetness and after dryness. SOLUTION: A hair treatment agent comprises a compound or salt thereof. The compound has 1 or more and 5 or less amino group in a molecule, the amino group binds to a predetermined quaternary ammonium cation-containing group, the total of the number of the amino group(s) in the molecule and the number of the quaternary ammonium cation(s) are 2 or more and 10 or less, and the number of carbon in the molecule excluding carbon included in the quaternary ammonium cation-containing group is 0 or more and 24 or less. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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Paragraph 0093
(2017/05/03)
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- A method for reducing betaine free acid in the process method of the (by machine translation)
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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)
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Paragraph 0033; 0034; 0035
(2017/11/08)
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- Preparation and hydrophobizing properties of carboxylic acid N-[3-(dimethylamino)propyl]amide hydrochlorides
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Carboxylic acid N-[3-(dimethylamino)propyl]amides were prepared in 90–95% yield by the reaction of carboxylic acid esters with N,N-dimethyl-1,3-diaminopropane in the presence of zeolites as catalysts. Hydrochlorides of these amides show promise as cationic surfactants for hydrophobization of the bottomhole formation zone of oil fields.
- Vlasova,Latypova,Akhmet’yanova,Gibadullina,Ratner,Telin,Dokichev
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p. 1102 - 1106
(2017/11/22)
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- Antistatic agent, formed product comprised of insulator polymer material, and manufacturing method thereof
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The present invention provides a donor-acceptor antistatic agent, which has high reproducibility and continuously prevents insulator polymer materials from being charged. The present invention provides an antistatic agent, which is used for an insulator polymer material comprising a donor-acceptor type molecular compound represented by the following formula (1), in which the donor-acceptor type molecular compound are obtained by mixing, melting and reacting a semipolar organoboron compound (a component of the donor) which is represented by the upper part of the following formula (1) with a basic nitrogen compound (a component of the acceptor) which is represented by the lower part of the following formula (1). In the formula (1), R1and R2 are respectively CH3(CH2)16-CO-OCH2 or HOCH2, and at least one of them is CH3(CH2)16-CO-OCH2; R3 and R4 are respectively CH3, C2H5, HOCH2, HOC2H4 or HOCH2CH(CH3); R5 is C2H4 or C3H6.
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Paragraph 0026
(2017/02/24)
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- ANTISTATIC AGENT, MOLDED ARTICLE COMPRISING AN INSULATING POLYMER MATERIAL, AND METHOD OF PRODUCING THE MOLDED ARTICLE
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An object of the present invention is to provide an antistatic agent composed of a donor-acceptor type molecular compound that can prevent static charge on an insulating polymer material surely with good persistency and reproducibility. The antistatic agent of the present invention is an antistatic agent for an insulating polymer material composed of a donor-acceptor type molecular compound represented by the general formula (1) below and obtained by mixing, melting and reacting a semi-polar organoboron compound (donor component) of the upper part in the general formula (1) below with a basic nitrogen compound (acceptor component) of the lower part in the general formula (1) below, wherein R1 and R2 are each independently CH3(CH2)16—CO—OCH2 or HOCH2 and at least one thereof is CH3(CH2)16—CO—OCH2; R3 and R4 are each independently CH3, C2H5, HOCH2, HOC2H4, or HOCH2CH(CH3); and R5 is C2H4 or C3H6.
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Paragraph 0055
(2017/01/02)
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- Synthesis and antibacterial activity of novel amido-amine-based cationic gemini surfactants
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A series of novel cationic gemini surfactants were synthesized from corresponding amido-amines in a single step reaction. The amido-amines were obtained from long chain carboxylic acids and 3-N,N-dimethylamino-1-propyl-amine with excellent isolated yield (up to 95 %). All the synthesized quaternary ammonium compounds (QACs) were further investigated for surface active properties. The critical micelle concentration (CMC) and the effectiveness of surface tension reduction were determined. The surface tension measurements of newly synthesized gemini surfactants showed good water solubility, and low CMC values, had great efficiency in lowering the surface tension and a strong adsorption at the air/water interface than the corresponding monomeric surfactants. Further, the antibacterial activity of the synthesized QACs against both Gram-positive and Gram-negative bacteria was also investigated.
- Ghumare, Anant K.,Pawar, Balu V.,Bhagwat, Sunil S.
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- Synthesis and surface active properties of novel carbohydrate-based cationic surfactants
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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.
- Nowicki, Janusz,Sokolowski, Adam,Reksa, Dagmara
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experimental part
p. 179 - 184
(2012/04/17)
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- A facile route towards the preparation of ultra-long-Chain amidosulfobetaine surfactants
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A series of novel, ultra-long-chain amidosulfobetaine surfactants were prepared by amidation of ultra-long-chain fatty acids directly with N,N-dimethyl-1,3-propanediamine in the absence of solvents, followed by quaternization of the intermediates with 1,3-propanesultone in ethyl acetate.
- Chu, Zonglin,Feng, Yujun
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experimental part
p. 2655 - 2658
(2010/01/07)
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- Dimer poly-quaternary compounds
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The present invention relates to a novel class of polymeric compounds having specific quaternized amine based upon a dimer acid reacted with an dimethyl amino propyl amine to make an amido amine, which is subsequently reacted to make a polymeric quaternary compound. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight cationic compound which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications.
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Page/Page column 9
(2008/06/13)
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- Production process for carboxylic amide and derivatives thereof
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A production process for a carboxylic amide compound in which color tone stability after the passage of time is good and in order to provide production processes for betaine, a quaternary ammonium salt and an amine salt using the above carboxylic amide compound, a production process for carboxylic amide and derivatives thereof characterized by reacting higher fatty acid or an ester thereof represented by the following Formula (1) with diamine represented by the following Formula (2) under the presence of an organic phosphonic acid compound represented by the following Formula (3) or adding the organic phosphonic acid compound after the reaction or after removing excess diamine after the reaction: [in-line-formulae]R1—COOR2 ??(1) [/in-line-formulae]wherein each of the R and Z groups and n are defined.
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Page/Page column 7
(2008/06/13)
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- Personal care compositions
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A concentrate including, by weight (a) 10% to 60%, preferably 25% to 35%, of a saturated fatty acid selected from stearic or palmitic acid, or mixtures thereof, in an adduct of an amidopropyldimethyl-2-hydroxyethyl ammonium halide, with substantially no free acid present, and (b) 40% to 90%, preferably 65% to 75%, of a low molecular weight alcohol or saturated fatty alcohol or alcohols, for use in personal care products, including hair care and skin care compositions.
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Page/Page column 2
(2008/06/13)
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- Softener composition
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A softener composition that can impart a high softening effect to clothes irrespective of the state of rinsing water, which contains (a) a compound of formula (1) below, (b) a compound of formula (3) below, and (c) a specific anionic surfactant, wherein the mole ratios between the components (a), (b) and (c) satisfy the following relationship: [(a)+(b)]/(c)=9/1 to 4/6; and wherein R1 represents a C13-36 alkyl group or the like, R10 and R12 respectively represent a C8-36 alkyl group or the like, R2, R11 and R13 respectively represent a C1-6 alkylene group, R3, R4, and R14 respectively represent a C1-3 alkyl group or the like, A, D and E respectively represent —COO—, —CONH— or the like, and “a”, “c” and “d” respectively denote 0 or 1.
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Page/Page column 6
(2008/06/13)
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- Functional alcohol releasing substance
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This invention discloses a substance which is a betaine ester of a functional alcohol that has an amido bond in its molecule and releases the functional alcohol.
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- Rapid Synthesis and Interconversions of Fatty 4,5-Dihydroimidazoles and Fatty 1,4,5,6-Tetrahydropyrimidines. Thermal Cyclizations of Fatty Amides Involving Phenyl Phosphorodiamidate
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Brief heating of ethane-1,2- and propane-1,3-bis-fatty amides at 235-250 deg C with phenyl phosphorodiamidate gave routes to high yields of 2-fatty alkyl-4,5-dihydroimidazoles and 1,4,5,6-tetrahydropyrimidines.Ready interconversions of fatty dihydroimidazoles and tetrahydropyrimidines, involving diamine exchange with solvent, were observed on brief heating of these materials in ethylenediamine and trimethylenediamine as solvents.
- Butler, Richard N.,Thornton, John D.,O'Regan, C.B.
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p. 2197 - 2200
(2007/10/02)
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