Synthesis and characterization of zwitterionic silicone sulfobetaine surfactants

Snow, Steven A.; Fenton, William N.; Owen, Michael J.

doi:10.1021/la00092a017

Cited by 60 publications

(45 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The value of c CAC is significantly lower than those reported for organic glycosides [55] which are in the range of 30-40 mN m -1 and is comparable to those reported for other trisiloxane surfactants [1][2][3][4][5][6][7][8][9][10].…”

Section: Equilibrium Surface Tension Measurementssupporting

confidence: 72%

“…Most of the studies to date report critical micelle concentrations (CMC) values from surface tension versus log surfactant concentration plots. Although the structure of the micelles formed was investigated in past few years, no conclusion was drawn on the tendency of these surfactants to form welldefined micelles [1][2][3][4][5][6][7][8][9][10].…”

Section: Equilibrium Surface Tension Measurementsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Characterization of Glycoside‐Based Trisiloxane Surfactant

Chen

Zhou

et al. 2011

J Surfact & Detergents

View full text Add to dashboard Cite

The synthesis of glycoside-based trisiloxane surfactants of the general formula Me 3 SiOSiMeR 1 OSiMe 3 (R 1 = (CH 2 ) 3 (OCH 2 CH 2 ) 2 OR 2 , R 2 = glycosyl) is described, and the surface activity properties of the surfactant are studied. Diethylene glycol monoallyl ether glycoside is synthesized by reacting the diethylene glycol monoallyl ether with glucose. The glycoside-based trisiloxane surfactant is prepared by hydrosilylation of the precursor glycoside with hydrogen-containing trisiloxane. The product is structurally characterized by IR, 1 H NMR and MS. The surface tension of an aqueous solution is reduced to approximately 20 mN m -1 at concentration level of 10 -4 mol L -1 .

show abstract

Section: Equilibrium Surface Tension Measurementssupporting

confidence: 72%

Section: Equilibrium Surface Tension Measurementsmentioning

confidence: 99%

Synthesis and Characterization of Glycoside‐Based Trisiloxane Surfactant

Chen

Zhou

et al. 2011

J Surfact & Detergents

View full text Add to dashboard Cite

show abstract

“…The values of the minimum surface tension (where CAC refers to critical aggregation concentration) (γ CAC ) are significantly lower than those reported for organic glucosamide gemini surfactants (33,34) and are comparable to those reported for other low molecular weight silicone surfactants, many of which contain the trisiloxane backbone (43)(44)(45)(46)(47). However, the γ CAC values are not much lower than those of the corresponding monomer.…”

Section: Resultsmentioning

confidence: 50%

Synthesis and characterization of glucosamide‐based trisiloxane gemini surfactants

Zhang

2004

J Surfact & Detergents

View full text Add to dashboard Cite

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...

show abstract

“…The same is true for cationic [9][10][11][12][13] and zwitterionic surfactants of the sulfobetaine 14,15 and carbobetaine [16][17][18] types. The interest in these substances stems from their superior properties as fabric-conditioning agents, wetting agents on low-energy surfaces, paint additives and adjuvants in cosmetic and agrochemical formulations.…”

Section: Introductionmentioning

confidence: 83%