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1.
Synthesis and Surface Active Properties of tri[(N‐alkyl‐N‐ethyl‐N‐Sodium carboxymethyl)‐2‐Ammonium bromide ethylene] Amines
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Ming Zhou Gang Luo Xingwen Wang Ze Zhang Gang Wang 《Journal of surfactants and detergents》2015,18(5):837-844
Trimeric betaine surfactants tri[(N‐alkyl‐N‐ethyl‐N‐sodium carboxymethyl)‐2‐ammonium bromide ethylene] amines were prepared with raw materials containing tris(2‐aminoethyl) amine, alkyloyl chloride, lithium aluminium hydride, sodium chloroacetate, and bromoethane by alkylation, Hoffman degradation reaction, carboxymethylation and quaternary amination reaction. The chemical structures of the prepared compounds were confirmed by FTIR, 1H NMR, MS and elemental analysis. With the increasing length of the carbon chain, the values of their critical micelle concentration initially decreased. Surface active properties of these compounds were superior to general carboxylate surfactants C10H21CHN+(CH3)2COONa. The minimum cross‐sectional area per surfactant molecule (Amin), standard Gibbs free energy adsorption (ΔGads) and standard Gibbs free energy micellization (ΔGmic) are notably influenced by the chain length n, and the trimeric betaine surfactants have greater ability to adsorb at the air/water interface than form micelles in solution. The efficiency of adsorption at the water/air interface (pC20) of these surfactants increased with the increasing length of the alkyl chain. Their foaming properties, wetting ability of a felt chip, and lime‐soap dispersing ability were also investigated. 相似文献
2.
Yun-peng Zhu Araki Masuyama Yoh-ichi Kirito Mitsuo Okahara 《Journal of the American Oil Chemists' Society》1991,68(7):539-543
Bis(sulfonate) types of amphipathic compounds with three long- chain alkyl groups were prepared by the reaction ofN- (long- chain acyl)diethanolamine diglycidyl ethers with long- chain fatty alcohols, followed by the reaction with propanesultone.
The diglycidyl ethers were easily obtained from the correspondingN- acyldiethanolamines and epichlorohydrin in the presence of a phasetransfer catalyst. The same types of compounds with two
longchain alkyl groups were also prepared from Nacetyldiethanolamine according to similar procedures. All these new double-
or triple- chain surfactants were soluble in water and showed much better micelle forming and ability to lower surface tension
than general types of single- chain surfactants with one sulfonate group. The critical micelle concentration (CMC) and γCMC values of the triple- chain compounds were still much smaller than those of the corresponding double- chain compounds with
two common alkyl groups. The efficiency of adsorption at the water/air interface (pC20) of these surfactants was very high. Their foaming properties, wetting ability toward a felt chip, and lime- soap dispersing
ability were measured.
To whom correspondence should be addressed at Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamadaoka
2-1, Suita, Osaka 565, Japan. 相似文献
3.
Synthesis and Surface Properties of a Novel Sodium 3‐(3‐Alkyloxy‐3‐oxopropoxy)‐3‐oxopropane‐1‐sulfonate at the Air–Water Interface
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Pandari Phani Kumar Rati Ranjan Nayak Sanjit Kanjilal 《Journal of surfactants and detergents》2015,18(4):689-695
The present paper describes the synthesis and evaluation of surface properties of a novel series of anionic surfactant, namely sodium 3‐(3‐alkyloxy‐3‐oxopropoxy)‐3‐oxopropane‐1‐sulfonate with varying alkyl chain length (C8–C16). Synthesis involves initial formation of the 3‐alkyloxy‐3‐oxopropyl acrylate along with fatty acrylate during the direct esterification of fatty alcohol with acrylic acid in the presence of 0.5 % NaHSO4 at 110 °C followed by sulfonation of the terminal double bond of the 3‐alkyloxy‐3‐oxopropyl acrylate. Synthesized compounds were evaluated for surface and thermodynamic properties such as critical micelle concentration (CMC), surface tension at CMC (γcmc), efficiency of surface adsorption (pC20), surface excess (Γmax), minimum area per molecule at the air–water interface (Amin), free energy of adsorption (?G°ads), free energy of micellization (?G°mic), wetting time, emulsifying properties, foaming power and calcium tolerance. Effect of chain length on CMC follows the classic trend, i.e. decrease in CMC with the increase in alkyl chain length. High pC20 (>3) value indicates higher hydrophobic character of the surfactant. These surfactants showed very poor wetting time and calcium tolerance, but exhibited good emulsion stability and excellent foamability. Foaming power and foam stability of C14‐sulfonate were found to be the best among the studied compounds. Foam stability of C14‐sulfonate was also studied at different concentrations over time and excellent foam stability was obtained at a concentration of 0.075 %. Thus this novel class of surfactant may find applications as foam boosters in combination with other suitable surfactants. 相似文献
4.
Preparation,Characterization and Properties of Novel Cationic Gemini Surfactants with Rigid Amido Spacer Groups
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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
5.
Linear homopolymers of N‐acryloyl‐N′‐alkyl piperazine (N′‐alkyl: methyl, ethyl, or propyl) and their corresponding crosslinked hydrogels were prepared. The polymers showed good responses to changes in the pH of the medium due to the presence of tertiary amine functions that could be protonated at a low pH. The nature of the N′‐alkyl group attached to the piperazine amino nitrogen greatly affected the pKa of the amino group. This in turn influenced the solution behavior of the polymers and was studied with light scattering, potentiometry, and viscosity measurements. The basicity of the polymers increased with an increase in the chain length of the N′‐alkyl substituent. The intrinsic viscosity of the polymers in a good polar organic solvent such as dimethylformamide decreased slightly with increasing temperature because of decreased thermodynamic affinity (interaction) at high temperatures. The viscosity behavior of the polymers in sodium chloride solutions was similar to that of classical polyelectrolytes. The swelling property of the hydrogels was studied with water sorption measurements, and the swelling was by anomalous (non‐Fickian) transport. The diffusion coefficient of the gels in solutions of pH 2.6 increased with increasing N′‐alkyl chain length, whereas at neutral pH, the effect was reversed. This behavior was attributed to the increase in both the basicity and hydrophobicity of the gels with an increase in the chain length of the N′‐alkyl groups. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008 相似文献
6.
Shuxin Tai Zhinong Gao Xueguo Liu Qi Zhang 《European Journal of Lipid Science and Technology》2012,114(9):1062-1069
Four anionic gemini surfactants of the sulfate type C12CnC12, where n is the spacer chain length (n = 3, 4, 6, and 10) were synthesized. The structures of these surfactants were confirmed by FT‐IR, 1H NMR, ESI mass spectra (ESI‐MS), and elemental analysis. The surface‐active properties of these compounds were investigated by means of surface tension, electrical conductivity, and fluorescence measurements. Premicellar aggregations were found for the four gemini surfactants, as revealed by the conductivity measurement. The formation of premicellar aggregates may account for the discrepancy between the critical micelle concentration (cmc) obtained by the surface tension and conductivity measurement. The cmc values of these gemini surfactants were much lower than that of sodium dodecylsulfate (SDS) and decreased monotonously with the increase of spacer chain length from 3 to 10. The effect of spacer chain length on the performance properties like foaming, emulsion stability, and lime soap dispersing ability were also studied and discussed. Practical applications : Alkyl sulfate surfactants are one of the most widely used surfactants. The new alkyl sulfate gemini surfactants synthesized in our study are more surface‐active than sodium dodecylsulfate. These gemini surfactants possess low critical micelle concentrations, high emulsion stability, and excellent lime soap dispersing ability. They have potential applications in the fields of cosmetics, detergents, etc. 相似文献
7.
Weihong Qiao Zhibo Zheng Huan Peng 《European Journal of Lipid Science and Technology》2011,113(7):841-847
Five long‐chain alkyl amidines were synthesized by condensation of N,N‐dimethylacetamide with octylamine, decylamine, dodecylamine, tetradecylamine, and hexadecylamine, respectively. Synthesis conditions including solvent, pH, temperature, and ratio of reactants were studied. The series of long‐chain alkyl amidine compounds reacted with dry ice to produce amidinium bicarbonates cationic amphipathic molecules. The critical micelle concentration (cmc) and surface tension at cmc (γcmc) measured by drop volume method show that these amphipathic molecules have excellent surface activity. The changes of cationic content measured by two‐phase titration and conductivity before and after bubbling CO2, show different properties between amidines and amidinium bicarbonates cationic amphipathic molecules. The switchable function of the amidinium bicarbonate cationic amphipathic molecule in emulsification and demulsification was studied. Practical applications : Our innovative work is synthesizing switchable amphipathic molecules, N′‐alkyl‐N,N‐dimethylacetamidines, by carbonyl‐amine condensation. Compared with a former way of synthesis, our work shows great potential advantages in industrial application. Our synthesis route is simpler with higher yield and is carried out at ambient temperature. Moreover, the products are environmentally friendly. Compared with traditional amphipathic molecules, our products, N′‐alkyl‐N,N‐dimethylacetamidines, show good switchable properties, which can be switched on and off, trigged by CO2.This means these products can be reused for several times, which is significant for environmental protection. 相似文献
8.
Sanjit Kanjilal Sadula Sunitha Paidimarla S. Reddy Koochana P. Kumar Upadyayula S. N. Murty Rachapudi B. N. Prasad 《European Journal of Lipid Science and Technology》2009,111(9):941-948
The synthesis of two types of imidazole‐based surfactants, [(ROCOCH2MIm)Br] and [(RNHCOCH2MIm)Br], of varying chain lengths (C10, C12 and C16), was conducted in the present work. The synthesis involves an initial reaction of bromoacetic acid with fatty alcohols or fatty amines, followed by quaternization with N‐methyl imidazole. The micellar properties of all the synthesized compounds were determined using surface tensiometry and compared with [(RMIm)Br], a well‐studied alkyl‐substituted imidazole‐based surfactant. Within the same homologous series, a decrease in critical micelle concentration (cmc) was observed with increasing alkyl chain length in all three types of cationic surfactants. Introduction of an ester [(ROCOCH2MIm)Br] or an amide group [(RNHCOCH2MIm)Br] in the alkyl chain lowers the cmc when compared to a cationic surfactant without functional group, [(RMIm)Br]. The synthesized surfactants were also assayed for antimicrobial activities and found to possess good activities against selected strains. 相似文献
9.
A new method for the preparation of new heterocyclic amine surfactants based on sulfobetaines is proposed. Interfacial activities of the surfactants obtained in aqueous solution were studied by surface tension measurements. The critical micelle concentration, surface excess concentration, minimum area per surfactant molecule, and standard Gibbs energy of adsorption were determined. The adsorption properties of these compounds depend significantly on the alkyl chain length. Alkyl chain length also affects biological properties of the new surfactants, determining the minimum inhibitory concentration and size of inhibited growth zone. The compounds have high antimicrobial activity. 相似文献
10.
Alkyl Xylosides: Physico‐Chemical Properties and Influence on Environmental Bacteria Cells
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Wojciech Smułek Ewa Kaczorek Zuzana Hricovíniová 《Journal of surfactants and detergents》2017,20(6):1269-1279
A group of four selected non‐ionic surfactants based on carbohydrates, namely octyl d ‐xyloside (C8X), nonyl d ‐xyloside (C9X), decyl d ‐xyloside (C10X) and dodecyl d ‐xyloside (C12X), have been investigated to accomplish a better understanding of their physico‐chemical properties as well as biological activities. The surface‐active properties, such as critical micelle concentration (CMC), emulsion and foam stability, the impact of the compounds on cell surface hydrophobicity and cell membrane permeability together with their toxicity on the selected bacterial strains have been determined as well. The studied group of surfactants showed high surface‐active properties allowing a decrease in the surface tension to values below 25 mN m?1 for dodecyl d ‐xyloside at the CMC. The investigated compounds did not have any toxic influence on two Pseudomonas bacterial strains at concentrations below 25 mg L?1. The studied long‐chain alkyl xylosides influenced both the cell inner membrane permeability and the cell surface hydrophobicity. Furthermore, the alkyl chain length, as well as the surfactant concentration, had a significant impact on the modifications of the cell surface properties. The tested non‐ionic surfactants exhibited strong surface‐active properties accompanied by the significant influence on growth and properties of Pseudomonas bacteria cells. 相似文献
11.
Preparation and properties of new lactose-based surfactants 总被引:1,自引:0,他引:1
Kazimiera A. Wilk Ludwik Syper Bogdan Burczyk Irena Maliszewska Marek Jon Beata W. Domagalska 《Journal of surfactants and detergents》2001,4(2):155-161
A new group of nonionic saccharide-based surfactants, N-alkanoyl-N-methyllactitolamines (alkanoyl: decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl), were synthesized and characterized. Surface
properties such as critical micelle concentration, standard free energy of adsorption, standard free energy of micellization,
surface tension reduction efficiency, effectiveness of surface tension reduction, surface excess concentration, and surface
area demand per molecule as well as foaming properties (i.e., foam volume and foam stability), contact angle, antiraicrobial
activity, and biodegradability were determined. The selected performance properties were evaluated in relation to commercially
available alkyl polyglucosides (Glukopon 600 EC(HH)-a Henkel product), and oligooxyethylenated decyl (C10E4) and dodecyl (E12E5) alcohols. The foaming-stabilizing effect and contact angle suggest that the lactose-derived surfactants that were studied
share some common properties with alkyl polyglucosides that are different from those with an oligooxyethylene grouping. All
tested N-alkanoyl-N-methyllactitolamines were practically nontoxic to bacteria and yeasts. These compounds are readily biodegradable in the Closed
Bottle test inoculated with activated sludge. N-Alkanoyl-N-methyllactitolamines with lower chain lengths (C10–C14) biodegraded at a slightly faster rate. Biological properties showed that this class of compounds fulfills all requirements
needed for environmental acceptance. 相似文献
12.
Sulfated Zirconium Catalyst for Synthesis of Dialkylated Diphenylether Disulfonate Gemini Surfactants
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Tiliu Jiao Xiaochen Liu Xiaoyu Wang Jinping Niu 《Journal of surfactants and detergents》2015,18(6):1067-1072
Dialkylated diphenylether disulfonate with different alkyl chain lengths (Cn‐DADS, n = 8, 10 and 12) has been synthesized by Friedel‐Crafts alkylation of olefins (C8, C10 and C12) and diphenyl oxide, followed by sulfonation and neutralization with fuming sulfuric acid. Sulfated zirconia solid acids were prepared and used to catalyze the alkylation reaction. The structure of sulfated zirconia solid acids was identified by infrared spectroscopy. The title compounds were confirmed by infrared spectroscopy and electrospray ionization‐mass spectrometry. Equilibrium surface tension measurements show that the critical micelle concentration (CMC) decreases with an increase in chain length, and the surface tension at CMC (γcmc) of C8‐DADS is the lowest. The minimum area per molecule (Amin) values of Cn‐DADS increase, while the surface excess concentration (Γmax) values decrease with the increase of the alkyl chain length. C10‐DADS has the highest pC20 and CMC/C20 among Cn‐DADS. 相似文献
13.
Bis[N,N′-(alkylamideethyl)ethyl] triethylenediamine surfactants are quaternary ammonium salt Gemini surfactants with amide, which
are synthesized from fatty acid (dodecanoic, hexadecanoic, tetradecanoic and octadecanoic) methyl esters, triethylene tetramine
and ethyl bromide. The chemical structures of the prepared compounds were characterized by elemental analysis, FTIR and 1H-NMR spectra, melting point and Krafft point. Several properties of the synthesized surfactants were studied including surface
tension, critical micelle concentration, interfacial tension, emulsification power, salt effect, corrosion inhibition efficiency
and biological activity. The results show that the surface activity, critical micelle concentration and interfacial activity
are correlated to their chemical structures. The emulsification power measurements of these surfactants show their low emulsifying
tendency towards Tazhong’s crude oil from Tarim Oilfield. The synthesized surfactants also exhibit high biocidal activity
towards Gram-positive and Gram-negative bacteria and fungi. This activity increases with the increase of alkyl chain length.
The corrosion measurement of these surfactants in acidic media with a weight loss technique show good protection of mild steel
alloys against acidic environments. These properties suggest that the synthesized compounds have potential for application
in the oilfield area. 相似文献
14.
Brahim Lakhrissi Loubna Lakhrissi Mohamed Massoui El Mokhtar Essassi Francesc Comelles Jordi Esquena Conxita Solans Carlos Rodríguez-Abreu 《Journal of surfactants and detergents》2010,13(3):329-338
The surface and self-aggregation properties in water of a new series of amphiphilic homologues, bis-benzimidazolone derivatives
of d-glucose, were investigated. Parameters such as the maximal surface excess concentration, minimal area per molecule at the
interface, and critical micelle concentration (CMC) were found to be significantly dependent on the hydrophobic alkyl chain
length. The synthesized compounds form micelles at remarkably low concentrations, and CMCs derived from surface tension measurements
show a minimum as a function of the alkyl chain length; this unusual trend can be attributed to the formation of submicellar
aggregates in compounds with long alkyl chains, as evidenced from fluorescence probe spectroscopy data. At high surfactant
concentrations, lyotropic liquid crystalline phases with hexagonal structure are formed. Small angle X-ray scattering measurements
indicate that the characteristic nanoscopic lengths increase with water swelling and alkyl chain length. 相似文献
15.
A Novel Alkyl Sulphobetaine Gemini Surfactant Based on S‐triazine: Synthesis and Properties
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Ruixia Niu Chao Wang Zhigang Sun Biao Long Hua Song Weidong Ren Daqiang Wang Junyao He 《Journal of surfactants and detergents》2017,20(6):1255-1262
A series of alkyl sulphobetaine Gemini surfactants Cn‐GSBS (n = 8, 10, 12, 14, 16) was synthesized, using aliphatic amine, cyanuric chloride, ethylenediamine, N,N′‐dimethyl‐1,3‐propyldiamine and sodium 2‐chloroethane sulfonate as main raw materials. The chemical structures were confirmed by FT‐IR, 1H NMR and elemental analysis. The Krafft points differ markedly with different carbon chain length, for C8‐GSBS, C10‐GSBS and C12‐GSBS are considered to be below 0 °C and C14‐GSBS, C16‐GSBS are higher than 0 °C but lower than room temperature. Surface‐active properties were studied by surface tension and electrical conductivity. Critical micelle concentrations were much lower than dodecyl sulphobetaine (BS‐12) and decreased with increasing length of the carbon chain from 8 to 16, and can reach a minimum as low as 5 × 10?5 mol L?1 for C16‐GSBS. Effects of carbon chain length and concentration of Cn‐GSBS on crude oil emulsion stability were also investigated and discussed. 相似文献
16.
Zhigang Xu Pengfei Li Weihong Qiao Zongshi Li Lubo Cheng 《Journal of surfactants and detergents》2006,9(3):245-248
Surface properties of two series of anionic arylalkyl surfactants, containing different aromatic rings in the straight aliphatic
chain, sodium N-aryloleyl-N-methyl-2-aminoethanesulfonates and sodium N-aryloleyl p-methoxyanili-nesulfonates, were investigated. An increase of the aromatic ring size in the alkyl chain increases the critical
micelle concentration (CMC) and surface tension at CMC. However, this also decreases the efficiency and effectiveness in reducing
water surface tension. The dominant factor of the decrease of efficiency and effectiveness is attributed to the function of
the hydrophilic segment and hydrophobic segment for arylalkyl surfactants, respectively. The same results are found in the
standard free energy of adsorption (ΔG
o
ads) and the standard free energy of micellization (ΔG
o
mic) values. Moreover, with the increase of the aromatic ring size, the adsorption and micellization of arylalkyl surfactants
begin to weaken. The data indicate that some parts of surface properties for arylalkyl surfactants are affected by the bulkiness
of the arylalkyl chain. The results provide opportunities for further detailed examination of surface properties of arylalkyl
surfactants with other branched alkyl chains. 相似文献
17.
E A M Gad Z Abdel‐Hamid D A Ismail R A El‐Adly 《Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986)》1999,74(4):345-348
N‐[(octyloxycarbonylmethyl)‐ N‐triethanol ammonium chloride] (C8 ), N ‐[(dodecyl‐oxycarbonylmethyl)‐ N‐triethanol ammonium chloride] (C12 ) and N ‐[(hexadecyloxycarbonylmethyl)‐N ‐triethanol ammonium chloride] (C16 ) were synthesized. Surface tension was measured in aqueous solution for different concentrations at 28, 38 and 48°C. Various surface properties of the synthesized surfactants were evaluated, particularly critical micelle concentration (CMC), efficiency (ΠCMC) as well as maximum surface excess (Γmax) and minimum surface area (Amin). Micellization and adsorption in both liquid/air and liquid/solid interfaces thermodynamics were investigated. These products have pronounced surface activity and satisfactory corrosion inhibition of C‐steel in hydrochloric acid at 28, 38 and 48°C. © 1999 Society of Chemical Industry 相似文献
18.
New amphoteric surfactants of N-(3-alkoxy-2-hydroxypropyl)-N-(2-hydroxyethyl)-β-alanine (APA) have been synthesized. The fundamental surface-active properties (critical micelle concentration
and isoelectric point) and hemolysis tests were also investigated to examine the effects of differences in chain length of
the alkoxy moiety. The hemolysis result of APA exhibited low constant values irrespective of the alkyl chain length. The amphoteric
APA surfactant was confirmed to have a mild effect on human microorganisms and to possess excellent surface-active properties.
In addition, a speculative model of micelle configuration was estimated by semiempirical molecular orbital simulations. 相似文献
19.
N-Dodecyl N-trimethylsilane ammonium chloride, N-tetradecyl-N-trimethylsilane ammonium chloride, N-hexadecyl-N-trimethylsilane ammonium chloride, and N-octadecyl-N-trimethylsilane ammonium chloride were prepared. Surface properties, particularly critical micelle concentration (CMC), effectiveness,
maximum surface excess, and minimal surface area, were determined at different concentrations at 20, 35, 50, and 65°C, respectively.
From electrical conductivity data, degrees of dissociation and dissociation constants at various concentrations were determined.
Free energies, enthalpies, and entropies of micellization and adsorption of the surfactants in aqueous solution were studied. 相似文献
20.
Bifunctional aminoalkyldimethylpropylammonium salts (N‐(3‐aminopropyl)‐N,N‐dimethylpentylammonium chloride, N‐(3‐aminopropyl)‐N,N‐dimethyloctylammonium chloride, N‐(3‐aminopropyl)‐N,N‐dimethyldecylammonium chloride, N‐(3‐aminopropyl)‐N,N‐dimethyldodecylammonium chloride) are synthesized and their structure‐dependent antibacterial effect against Gram‐negative Escherichia coli and Gram‐positive Lactococcus lactis is investigated. To this end, resins prepared from bisphenol A diglycidyl ether (2,2‐bis[4‐(glycidyloxy)phenyl]propane) and diethylenetriamine (2,2′‐diaminodiethylamine) as matrix and the bifunctional aminoalkyldimethylpropylammonium salts in a ratio of 6 mol% compared to epoxy components are used. A dependence of antibacterial effect on alkyl chain length of the quaternary ammonium compounds is observed for both species. Furthermore, resins with N‐(3‐aminopropyl)‐N,N‐dimethyldecylammonium chloride in varying concentrations up to 16 mol% for both organisms show a concentration‐dependent antibacterial effect of the quaternary ammonium salt. The antibacterial materials are characterized by differential scanning calorimetry, infrared spectroscopy and rheological studies. © 2013 Society of Chemical Industry 相似文献