Thermotropic liquid-crystalline properties of some novel hexuronic acid derivatives bearing a single or two alkyl chains

Auvray, X.; Labulle, B.; Petipas, C.; Bertho, Jean-Noël; Benvegnu, Thierry; Plusquellec, Daniel

doi:10.1039/a607305k

Cited by 9 publications

(5 citation statements)

References 19 publications

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“…It is noteworthy that the variability of the hydrophilic part of 11a – d can be obtained using different amines. For instance, the use of fatty amines provides surfactants like 11a having potential applications in shampoos and detergents, , and the thermotropic properties of the product obtained with octylamine have been studied . Use of taurine can also provide the anionic surfactant 11b, and cationic surfactants 11c can be obtained by the use of N , N -dimethylethylene diamine followed by quaternarization .…”

Section: Introductionmentioning

confidence: 99%

“…For instance, the use of fatty amines provides surfactants like 11a having potential applications in shampoos and detergents, 17,18 and the thermotropic properties of the product obtained with octylamine have been studied. 19 Use of taurine can also provide the anionic surfactant 11b, 20 and cationic surfactants 11c can be obtained by the use of N,Ndimethylethylene diamine followed by quaternarization. 21 This study has also reported the use of ethanolamine to give 11d with decyl, undecyl, and dodecyl alkyl chains, but no physicochemical characterizations were reported for these compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

Lebeuf

Liu

Pierlot

et al. 2018

ACS Sustainable Chem. Eng.

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A series of 13 well-defined alkylglucuronamides [AGUA] surfactants with hydrophobic chains consisting of fatty alcohols (C8, C12, or C16) involved in a glucosidic bond has been synthesized in two steps from glucuronic acid or glucuronolactone. The nonionic polar heads are a sugar unit with an amide function derived from five different amines, i.e., methylamine, ammonia, ethanolamine, ethoxyethanolamine, and aminopropanediol. Their CMC values present variations from 0.03 to 29 mM, and their hydrophilic/lipophilic behaviors have been compared to conventional dodecyl polyethoxylated surfactants (C12E j ) using the PIT-slope methodology. They cover a large scale of the corresponding C12E j with j varying from 5 to 8. Regarding functional properties, the novel alkylglucuronamides exhibit good foaming properties. Last but not least, two of them could be classified as easily biodegradable according to respirometric tests.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

Lebeuf

Liu

Pierlot

et al. 2018

ACS Sustainable Chem. Eng.

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“…-a hydrophilic head consisting of cyclic or acyclic sugar residues based on one or more rings of 5 or 4 carbons bearing different functional groups [9][10][11][12]; -a hydrophobic part; -a linkage between the two parts: an oxygen or sulphur atom [13], a group with various degrees of ionization or polarizability [14,15]. The head and the chain may also be in either the α or β orientation [16].…”

Section: Introductionmentioning

confidence: 99%

“…The non-ionic surfactant properties of the alkylglucosides and alkylpolyglucosides can be compared with those of the n-alkylpolyethylene glycol ethers (C n EO m ) or other surfactants [5,6]. Functional groups may be linked to the sugar moiety [7][8][9] producing surfactants with highly specific properties. The sugar-based derivatives, which can be produced in a number of molecules, are more complex than conventional surfactants: the effects of oligosaccharide stereochemistry on the physical properties of aqueous synthetic glycolipids have been the subject of study over recent years [10].…”

Section: Introductionmentioning

confidence: 99%

Small-angle X-ray diffraction study of the thermotropic and lyotropic phases of five alkyl cyclic and acyclic disaccharides: Influence of the linkage between the hydrophilic and hydrophobic moieties

Auvray

Petipas

Dupuy

et al. 2001

The European Physical Journal E

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We present a comparative study of the thermotropic and lyotropic phases of 5 surfactants with an aliphatic chain of 12 carbon atoms and a cyclic or acyclic sugar head with different linkages between the two moieties. These linkages can concern different chemical groups or different orientations between the head and the chain. The compounds included the α-and β-N dodecyl-D-maltosides, N-dodecylamino-1-deoxylactitol, N-dodecyl lactobionamide and N-acetyl N-dodecyl lactosylamine. The influence of the polar head (with closed-and opened-type sugars) and the linkage with the hydrocarbon chain on the phases obtained by the heating of the anhydrous compounds and after addition of water was studied by X-ray diffraction and optical microscopy. In the anhydrous state, the surfactants were either crystalline or amorphous. On heating, they went through a liquid crystal smectic phase which, in some cases, was preceded by solid-to-solid transitions. On addition of water, the sequence of phases from the micellar phase to the lamellar phase was accounted for in terms of the geometric model of Sadoc and Charvolin. However, with certain surfactants this sequence was not complete, and the domains of existence of phases were altered. PACS. 61.30.Eb Experimental determination of smactic, nematic, cholesteric and other structures -61.10.Nz Single crystal and powder diffraction -64.70.Md Transitions in liquid crystals

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“…Glucuronic acids or their lactone derivatives are useful resources for the preparation of carbohydrate esters, by reaction with fatty alcohols. Both chemical and enzymatic procedures towards amphiphilic glucuronates have been reported (Figure 18) [148][149][150][151][152][153][154][155][156]. Though very close in structure compared to acylated sugars, this change in the OCOR vs COOR linkage has some influence on the properties [157].…”

Section: Glycosidesmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

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GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

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Thermotropic liquid-crystalline properties of some novel hexuronic acid derivatives bearing a single or two alkyl chains

Cited by 9 publications

References 19 publications

Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

Small-angle X-ray diffraction study of the thermotropic and lyotropic phases of five alkyl cyclic and acyclic disaccharides: Influence of the linkage between the hydrophilic and hydrophobic moieties

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

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