Synthesis and Surface Active Properties of Novel Nonionic Aryl Oleic Diethanolamide Surfactants

Xu, Zhisheng; Liu, Dongliang; Qiao, Wenxiao; Li, Zongshi; Liu, Cheng

doi:10.1080/10916460500292717

Cited by 6 publications

(3 citation statements)

References 11 publications

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“…In previous articles (11)(12)(13)(14)(15), the synthesis of arylalkyl surfactants was reported. Since the reaction of oleoyl chloride with N-methyltaurine has been industrialized, the key of synthesizing these compounds is the alkylation, which is the introduction of the aromatic ring compounds to oleic acid.…”

Section: Resultsmentioning

confidence: 99%

Effect of aromatic ring in the alkyl chain on surface properties of arylalkyl surfactant solutions

Qiao

et al. 2006

J Surfact & Detergents

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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-methoxyanilinesulfonates, 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 (∆G°a ds ) and the standard free energy of micellization (∆G°m ic ) 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.Paper no. S1529 in JSD 9, 245-248 (Qtr. 3, 2006).The traditional methods of altering hydrophobicity of a surfactant are to vary the length of the straight alkyl chain or the different hydrophilic groups. It is well known that an increase of the straight alkyl chain length of conventional alkyl surfactants can decrease the critical micelle concentration (CMC) and increase the efficiency and effectiveness in reducing water surface tension (1,2). However, the branched aliphatic chain of the surfactants exhibits complicated effects on their CMC and surface tensions (3-6). The relationship between the structure of the hydrophobic chain and surface properties has already been studied by Matsuoka and Moroi (7) and Aksenenko and colleagues (8). The effects of alkylbenzenesulfonate molecules with different branched aliphatic chains on adsorption and surface tension were also reported (3). For these surfactants, the aromatic rings are usually attached by hydrophilic groups. Arylalkyl surfactants, differing from the existing surfactants, having the sulfonate group attached to the alkyl chain rather on the aromatic ring, exhibited better solubility in water and better thermal stability than the conventional alkyl or alkyl-aryl sulfonate surfactants (9,10). In this study, the effects of increasing the arylalkyl chain size from phenyl to naphthyl on their surface properties are reported. The values of CMC and surface tensions (γ cmc ) for these arylalkyl surfactants increase with an increase of arylalkyl chain size. Thus, the effect of structural features on their surface behavior is analyzed through changes in surface properties, including the surface excess concentration at surface saturation (Γ m ), the effectiveness of adsorption, the area per surfactant molecule at the air/water interface at surface saturat...

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Section: Resultsmentioning

confidence: 99%

Effect of aromatic ring in the alkyl chain on surface properties of arylalkyl surfactant solutions

Qiao

et al. 2006

J Surfact & Detergents

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“…Because self-assembled materials are used in a variety of different applications including detergency, catalysis, model biomembranes, protein crystallization, and drug delivery, among others, the ability to control their self-assembly behavior is highly desirable [5][6][7][8][9][10][11][12][13]. Diethanolamides, in particular, constitute some of the best and most commonly used foam boosters for aqueous solutions [14,15]. Amphiphiles in aqueous solutions can self-assemble into a variety of structures based on the local constraints imposed by the effective shape of the molecule combined with the influence imposed by the competing interactions of the polar head-groups and the alkyl chains.…”

Section: Introductionmentioning

confidence: 99%

Nonionic diethanolamide amphiphiles with saturated hydrocarbon chains: Neat crystalline and lyotropic liquid crystalline phase behavior

Sagnella

Conn

Krodkiewska

et al. 2012

Journal of Colloid and Interface Science

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“…In addition, Yan et al 18 also found that heterodouble-chained N -acyltaurate surfactants that possessed good solubility and low CMC values had similar properties to some Gemini surfactants. Xu et al 19 synthesized aryl oleic diethanolamide surfactants with different hydrophobic groups, and it was reported that the introduction of the aromatic ring in the long alkyl chain could significantly reduce the surface tension. Yang et al 20 prepared multi-alkylated aromatic amides with different numbers of alkyl side chains, and it was validated that they could stabilize the associated asphaltene particles effectively in crude oil via hydrogen bonding, π–π interaction, and acid–base interaction.…”

Section: Introductionmentioning

confidence: 99%

The effect of aromatic side chains on the dilational rheological properties of N-acyltaurate amphiphiles at water–decane interfaces

Zhu,

Xu,

Zhang

et al. 2024

Soft Matter

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Synthesis and Surface Active Properties of Novel Nonionic Aryl Oleic Diethanolamide Surfactants

Cited by 6 publications

References 11 publications

Effect of aromatic ring in the alkyl chain on surface properties of arylalkyl surfactant solutions

Effect of aromatic ring in the alkyl chain on surface properties of arylalkyl surfactant solutions

Nonionic diethanolamide amphiphiles with saturated hydrocarbon chains: Neat crystalline and lyotropic liquid crystalline phase behavior

The effect of aromatic side chains on the dilational rheological properties of N-acyltaurate amphiphiles at water–decane interfaces

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