Preparation and surface‐ active properties of new amphipathic compounds with two phosphate groups and two long‐ chain alkyl groups

Zhu, Yun; Masuyama, Araki; Okahara, Mitsuo

doi:10.1007/bf02657622

Cited by 55 publications

(37 citation statements)

References 19 publications

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“…Synthesis of phosphodiesters with rigid spacer and polar spacer also involve a multistep but routine procedure which are described in Scheme 2 (8) and Scheme 3 (9). Synthesis of anionic geminis with sulfonate head groups is described in Scheme 4 (10)(11).…”

Section: Structurementioning

confidence: 99%

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Anionic Gemini Surfactants: A Distinct Class of Surfactants

Shukla

Tyagi

2006

J. Oleo Sci.

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Anionic gemini surfactants are a new class of surfactants that comprise of two anionic head groups and two hydrophobic tails separated by a spacer group. Anionic gemini surfactants have low cmc values and show extraordinary surface activity. These surfactants have good water solubility and their ability to form micelles and lowering surface tension characteristics are fairly good as compared to conventional anionic surfactants. These surfactants have excellent lime soap dispersing ability (LSDA) too. Because of their higher surface activity these surfactants are used as promising surfactants in industrial detergency and emulsification. These surfactants are cost effective in area such as laundry detergent compositions, soil clean up, enhanced oil recovery and hydrotropic agents. This review deals with structure, synthesis, critical micelle concentration, surface active properties, performance properties, uses and biodegradability of anionic geminis.

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Section: Structurementioning

confidence: 99%

“…For surfactant to be considered soluble their Krafft point temperature has to be below room temperature (32). The Krafft point of several disulfonate (33,34), disulfate (12) and diphosphate (9) anionic geminis have been reported below those of comparable conventional surfactants.…”

Section: Solubilizationmentioning

confidence: 99%

Anionic Gemini Surfactants: A Distinct Class of Surfactants

Shukla

Tyagi

2006

J. Oleo Sci.

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“…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)(15)(16)(17)(18)(19)(20)(21)(22)(23)(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 1990, Zhu et al [23] synthesized sulfate anionic Gemini surfactants by the reaction of glycol diglycidyl ethers with long-chain alcohols, followed by sulfation with chlorosulfonic acid and found these compounds superior in surface active properties to general anionic ones. In 1991 and 1993, they reported double-chain surfactants with two phosphate groups and two carboxylate groups, respectively [24,25]. Menger [26] and Duivenvoorde [27] synthesized two phosphate Gemini surfactants in 1991 and 1997, respectively.…”

Section: Introductionmentioning

confidence: 97%

Effects of Spacers on Surface Activities and Aggregation Properties of Anionic Gemini Surfactants

Cao¹,

Li²,

Song³

et al. 2009

J Surfact & Detergents

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This present article employs four anionic Gemini surfactants with different spacer groups and investigates their physicochemical and aggregation properties. The critical micelle concentration (CMC), surface tension at CMC (c CMC ) and C 20 of these surfactants have been investigated using the du Nouy ring method. The aggregation number (N) was determined with intrinsic fluorescence quenching method using pyrene as a fluorescence probe and benzophenone as a quencher. Results show that these anionic Gemini surfactants have lower CMC and C 20 values compared with those conventional ones and show higher surface activity. As expected, the spacer plays an important role in the aggregation properties of Gemini surfactants. Under experimental conditions, Gemini B-D with an alkoxylated group as spacer has a lower CMC and a higher aggregation number than Gemini A with methylene as spacer. For Gemini B-D, the CMC and aggregation number values decrease with the increasing flexible spacer length. The micropolarity also affects the aggregation of the present anionic Gemini surfactants. The micropolarity of micelle becomes low when the concentration of surfactants increases. Aggregation numbers of surfactants increase and fluorescence intensities decrease with the increasing concentration of NaCl. These results will help us to understand the relationship between the architectures of Gemini surfactants and their various properties in aqueous solution.

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Preparation and surface‐ active properties of new amphipathic compounds with two phosphate groups and two long‐ chain alkyl groups

Cited by 55 publications

References 19 publications

Anionic Gemini Surfactants: A Distinct Class of Surfactants

Anionic Gemini Surfactants: A Distinct Class of Surfactants

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Effects of Spacers on Surface Activities and Aggregation Properties of Anionic Gemini Surfactants

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