Synthesis and Properties of Bis (taurine) Types of Double-chain Surfactants

Masuyama, Araki; Hirono, T.; Zhu, Yunpeng; Okahara, Mitsuo; Rosen, Milton J.

doi:10.5650/jos1956.41.301

Cited by 21 publications

(9 citation statements)

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“…So far, the various gemini surfactants containing different spacers, for example, a flexible hydrophilic [2][3][4][5], flexible hydrophobic [6,7], or rigid hydrophobic [8][9][10][11], have been investigated. Among a class of cationic gemini surfactants containing hydroxyl substituted spacer interests us [12][13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Adsorption and aggregation of 2-hydroxyl-propanediyl-α,ω-bis(dimethyldodecyl ammonium bromide) in aqueous solution: Effect of intermolecular hydrogen-bonding

Pei

You

Zhao

et al. 2010

Journal of Colloid and Interface Science

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Section: Introductionmentioning

confidence: 99%

Adsorption and aggregation of 2-hydroxyl-propanediyl-α,ω-bis(dimethyldodecyl ammonium bromide) in aqueous solution: Effect of intermolecular hydrogen-bonding

Pei

You

Zhao

et al. 2010

Journal of Colloid and Interface Science

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“…The unique surfactant properties of gemini surfactants have prompted investigations by a number of researchers. Those that have been studied in greatest depth, in terms of their physicochemical behavior, have been the cationic gemini surfactants (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), although research on anionic (14-24), zwitterionic (25), and nonionic (26)(27)(28)(29)(30)(31)(32)(33)(34)(35) dimeric surfactants also has been conducted.…”

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confidence: 99%

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Zhang

2004

J Surfact & Detergents

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A new family of glucosamide-based trisiloxane gemini surfactants of the general formula (CH 2 OCH 2 ) n (Me 3 SiOSiMeR 1 OSiMe 3 ) 2 (where R 1 = (CH 2 ) 3 NR 2 (CH 2 ) 2 NHCO (CHOH) 4 CH 2 OH; R 2 = CH 2 CH(OH)CH 2 OCH 2 ; and n = 0, 1, or 2) was prepared and characterized, both structurally and as aqueous surfactants. The monomer was prepared by amidation of the precursor amine functional trisiloxane with D-gluconic acid δ-lactone. Gemini surfactants were then prepared by the alkylation of the precursor secondary amine with oligoethylene glycol diglycidyl ethers. They were structurally characterized by proton and 13 C nuclear magnetic resonance and elemental analysis. Members of this family reduced the surface tension of water to approximately 21 mN/m at concentration levels of 10 −5 mol/L. These gemini compounds showed two critical aggregation concentration values. This behavior resulted from the formation of premicellar aggregates before true micelles were formed.In recent years, silicone surfactants have attracted considerable interest because of their many technical applications. Owing to their unique molecular structure compared with that of normal hydrocarbon surfactants, they have excellent surface-active properties for special purposes. They can also reduce the surface tension of water to lower values than can be obtained using traditional organic surfactants. Furthermore, because of their bulkiness and molecular structure, the adhesion forces between the individual molecules in interfacial films are small; for this reason, the compounds act as good wetting agents. Silicone surfactants are also known for their low physiological risk in cosmetic applications.In contrast, sugar-based surfactants have been known for many years. In recent years, they have begun to be produced on an industrial scale and their use has gradually increased because of their valuable properties, such as good dermatological compatibility, excellent biodegradability, and the absence of toxic effects.Over a decade ago, gemini (dimeric) surfactants, a new class of surfactants consisting of two hydrophobic chains and two hydrophilic headgroups connected by a relatively short (rigid or flexible) spacer, were developed. These dimeric compounds show improved surfactant properties compared with monomeric surfactants. Gemini surfactants have attracted considerable interest, since these compounds have much smaller critical micelle concentration (CMC) values, much greater efficiency in reducing surface tension than expected, and better aggregation behavior. Gemini surfactants have been generating increasing interest owing to their tunable molecular geometry and their superior performance in applications (the CMC of the gemini is very low, so less gemini may be needed to reduce the surface tension of the solution).The unique surfactant properties of gemini surfactants have prompted investigations by a number of researchers. Those that have been studied in greatest depth, in terms of their physicochemical behavior, have been the cationic gemin...

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“…In the past decade, a new type of surfactant called gemini surfactants has attracted considerable interest (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19), since these compounds have much smaller cmc values and much greater efficiency in reducing surface tension than expected. They have two hydrophobic chains and two hydrophilic head groups in the molecule.…”

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Micelle ionization degree of anionic gemini surfactant having N,N‐dialkylamide and carboxylate groups

Tsubone¹,

Ghosh

2003

J Surfact & Detergents

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The critical micelle concentration (cmc) behavior in aqueous NaCl solutions of the anionic gemini surfactant N, N'-ethylenebis(sodium N-dodecanoyl-β-alanate), (CH 2 ) 2 [N-(COC 11 H 23 )CH 2 CH 2 (CO 2 Na)] 2 (212), having N,N-dialkylamide and carboxylate groups in a molecule was investigated to measure the value of micelle ionization degree (α). For comparison, the behavior of sodium N-dodecanoyl-N-methyl-β-alanate (SDMA), a monomer corresponding to 212, also was investigated. The α value obtained from the Corrins-Harkins plot for 212 is 0.97 when [Na + ] ≤ 0.025 M and the value for SDMA is 0.51 when [Na + ] ≤ 0.1 M. That the α for 212 is larger than that for SDMA reflects the higher pK a1 value for 212 than the pK a value of SDMA. For 212, when [Na + ] ≤ 0.025 M the amount of Na + released during micellization is so large that the Na + concentration above the cmc is almost equal to that below the cmc, and therefore 212 nearly behaves as a nonionic surfactant.Paper no. S1330 in JSD 6, 225-229 (July 2003).KEY WORDS: Anionic gemini surfactant, Corrin-Harkins plot, degree of counter-ion binding, micelle ionization degree.Unusual interfacial behaviors are shown by two anionic surfactants, sodium N-dodecanoyl-N-methyl-β-alanate (SDMA) and sodium N-dodecanoylsarcosinate (SDSA), having N,Ndialkylamide and carboxylate groups, in comparison with those of sodium N-dodecanoyl-N-methyltaurate (SDMT), having a sulfonate group instead of a carboxylate group, and sodium decyloxyacetate (SDOA), containing an ether oxygen instead of an N-methyl adjacent to the methylenecarboxylate group (1). The unusual behaviors were found to be due to the simultaneous presence of the N,Ndialkylamide and carboxylate groups in the same molecule. Namely, the increasing order of conductance/surface tension critical micelle concentration (cmc) ratios is SDOA < SDMT < SDSA < SDMA. This order is the same as those of the parameters, A min (the minimum area occupied by the surfactant molecule at the air/water interface) and cmc/C 20 ratio (a measure of the factors inhibiting micellization relative to adsorption at the air/water interface), implying that there is a steric factor inhibiting micellization for the compounds having N,N-dialkylamide and carboxylate groups. The same order of increase in pH with surfactant concentration in the vicinity of the cmc appears to indicate H-bonded interaction between amide and protonated carboxylate groups. Thus, anionic surfactants having N,N-dialkylamide and carboxylate groups release Na + in micellization.In the past decade, a new type of surfactant called gemini surfactants has attracted considerable interest (2-19), since these compounds have much smaller cmc values and much greater efficiency in reducing surface tension than expected. They have two hydrophobic chains and two hydrophilic head groups in the molecule. The gemini surfactants are the subject of more studies, because of the extraordinary surface activity (3,9,13,14,19,20).For several years, Tsubone and coworkers have studied the anionic gemini surfa...

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Synthesis and Properties of Bis (taurine) Types of Double-chain Surfactants

Cited by 21 publications

References 0 publications

Adsorption and aggregation of 2-hydroxyl-propanediyl-α,ω-bis(dimethyldodecyl ammonium bromide) in aqueous solution: Effect of intermolecular hydrogen-bonding

Adsorption and aggregation of 2-hydroxyl-propanediyl-α,ω-bis(dimethyldodecyl ammonium bromide) in aqueous solution: Effect of intermolecular hydrogen-bonding

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Micelle ionization degree of anionic gemini surfactant having N,N‐dialkylamide and carboxylate groups

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