Structures of micelles formed by synthetic alkyl glycosides with unsaturated alkyl chains

Milkereit, Götz; Garamus, Vasil M.; Veermans, K.; Willumeit‐Römer, Regine; Vill, V.

doi:10.1016/j.jcis.2004.10.039

Cited by 35 publications

(25 citation statements)

References 29 publications

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“…39,40 Nevertheless, a 40% difference as observed in SL is too large to be explained by chain conformation, packing or curvature differences, as usually done.…”

Section: E-mentioning

confidence: 95%

“…These discrepancies are too large to be neglected. Typical cross-sectional radius reported in litterature for sodium oleate micelles is 26 Å 54 while for an oleic-acid based glycolipid, whose polar head is constituted by a disaccharide and referred to as OM, 40,55 is 25 Å. It is very interesting to note that almost no discrepancy exists between the cross-section sizes of sodium oleate and OM, despite the additional disaccharide group in the last compound.…”

Section: E-mentioning

confidence: 97%

“…[31][32][33][34][35][36][37][38] Furthermore, in the specific case of alkylpolyglucosides (APG), no pH-driven long-range ordering of micelles is found until concentration values reach at least 10-20 wt%. 12,[39][40][41] On the contrary, long-range intermicellar interactions for these systems can be controlled at lower concentrations by adding specific electrical charges at the micellar outer surface using ionic surfactants. 42 In SL-based systems, electrical charges are autogenerated by pH (deprotonation of COOH group).…”

Section: E-mentioning

confidence: 99%

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Unusual, pH-Induced, Self-Assembly Of Sophorolipid Biosurfactants

et al. 2012

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International audienceAn increasing need exists for simple, bioderived, nontoxic, and up-scalable compounds with stimuli-responsive properties. Acidic sophorolipids (SL) are glucose-based biosurfactants derived from the yeast broth of Candida bombicola (teleomorph: Starmerella bombicola). The specific design of this molecule, a sophorose head with a free end-COOH group at the end of the alkyl chain, makes it a potentially interesting pH-responsive compound. We have specifically investigated this assumption using a combination of small angle neutron scattering (SANS), transmission electron microscopy under cryogenic conditions (Cryo-TEM), and nuclear magnetic resonance (NMR) techniques and found a strong dependence of SL self-assembly on the degree of ionization, α, of the COOH group at concentration values as low as 5 and 0.5 wt %. At least three regimes can be identified where the supramolecular behavior of SL is unexpectedly different: (1) at low α values, self-assembly is driven by concentration, C, and micelles are mainly identified as nonionic objects whose curvature decreases (sphere-to-rod) with C; (2) at mid α values, the formation of COO– groups introduces negative charges at the micellar surface inducing an increase in curvature (rod-to-sphere transition). Repulsive electrostatic long-range interactions appear at this stage. In both regimes 1 and 2, the cross-section radius of the micelles is below 25 Å. This behavior is concentration independent. (3) At α = 1, individual micelles seem to favor the formation of large netlike tubular aggregates whose size is above 100 nm. Such a complex behavior is very unique as it is generally not observed for common alkyl-based surfactants in concentration ranges below 5–10 wt %

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“…39,40 Nevertheless, a 40% difference as observed in SL is too large to be explained by chain conformation, packing or curvature differences, as usually done.…”

Section: E-mentioning

confidence: 95%

Section: E-mentioning

confidence: 97%

Section: E-mentioning

confidence: 99%

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Unusual, pH-Induced, Self-Assembly Of Sophorolipid Biosurfactants

et al. 2012

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“…The derivative with an unsaturated chain migrates faster at the airwater interface, and reduces readily the dynamic surface tension, compared to the saturated one. It is attributed to the "shortening effect" of the double bond inclusion (Milkereit et al 2005), reducing the hydrophobicity of the surfactant, and therefore, its adsorption time. derivatives.…”

Section: Unsaturationmentioning

confidence: 99%

Carbohydrate-Based Surfactants: Structure-Activity Relationships

Razafindralambo¹,

Blecker²,

Paquot³

2012

Advances in Chemical Engineering

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“…15 Alquil poliglicosídeos podem diferenciar-se de acordo com a quantidade de anéis de glicose presentes em sua cadeia. A maioria dos APGs apresentados na literatura possuem de um a três anéis de glicose [16][17][18][19] e há ainda trabalhos com os alquil poliglicosídeos superiores sintetizados com cinco ou mais anéis de glicose, 20 no entanto, nenhum com cinco anéis de glicose derivados a partir do amido. Neste trabalho, os APGs sintetizados possuem cinco anéis de glicose por cadeia alquílica, derivados da degradação da amilose como partes hidrofílicas, e utilizam alcoóis com cadeias de 10, 16 e 18 átomos de carbono como partes hidrofóbicas.…”

Section: Introductionunclassified

Novos surfactantes alquil poliglicosídicos à base de amilose extraída da batata inglesa (Solanum tuberosum l.)

et al. 2017

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NEW ALKYL POLYGLYCOSIDES SURFACTANTS BASED ON AMYLOSE EXTRACTED FROM ENGLISH POTATO (SOLANUM TUBEROSUM L.).Alkyl polyglycosides (APGs) are new biodegradable surfactants, non-toxic, synthesized from abundant renewable sources, potentially more appropriate than anionic surfactants. A range of glycosides denoted APG-Cy was synthesized by the Köenig-Knorr reaction using C 10 , C 16 and C 18 alcohols and derived from the degradation of amylose from English potato. The molecular structures of the glycosides were characterized by Nuclear Magnetic Resonance ( 1 H and 13 C NMR) together with Infrared Spectroscopy (FTIR) and Gel Permeation Chromatography (GPC). The study by NMR allowed the junctions between hydrophilic head groups and hydrophobic tail-groups to be characterized in detail. Conformation of the glycosidic units is 4 C 1 type with a b anomeric configuration. The formation of glycosides with five glucose rings linked to the alkyl chain was confirmed by 1 H NMR and GPC. Liquid crystals identified by the presence of double melting points were observed by Differential Scanning Calorimetry (DSC) showing thermotropic properties. The surface tension (g) and critical micelle concentration (cmc) were determined by du Noüy method, noting that increasing the length of alkyl chain led to the expected reduction in the cmc. The energies of adsorption and micellization processes calculated from isotherms g versus ln c (g.dm -3 ) indicate cooperativeness of hydrophilic and hydrophobic groups.Keywords: synthesis; characterization; alkyl polyglycosides surfactants; amylose; fatty alcohols. INTRODUÇÃOO consumo de agentes tensoativos não iônicos cresceu no mercado nos últimos 50 anos, devido sua baixa toxicidade e sua vasta utilização em produtos de limpeza, cosméticos, farmacêuticos e alimentícios, atingindo a marca de 30% de toda a produção de surfactantes em nível mundial, porém, concomitantemente, cresceu a preocupação relacionada com possíveis impactos ambientais. 1 Surfactantes podem ser derivados de carboidratos e álcoois graxos. 2 Alquil poliglicosídeos (APGs) são surfactantes não iônicos de interesse especial por serem produzidos a partir de recursos renováveis, 3 tais como a amilose do amido da batata inglesa, tornando-se substitutos de outros surfactantes que são potencialmente prejudiciais à saúde e ao meio ambiente. 4 A batata (Solanum tuberosum L.), também conhecida como batatinha ou batata-inglesa, é nativa da América do Sul, da Cordilheira dos Andes. Ocupa o 4º lugar entre os alimentos mais consumidos do mundo, sendo superada apenas pelo trigo, arroz e milho. No Brasil, é considerada a principal hortaliça, tanto em área cultivada como em preferência alimentar. 5-6 O amido é o principal polissacarídeo do milho, arroz, trigo e batata inglesa, que, por sua vez, são as principais fontes de amido. Estes se apresentam na forma de grânulos e diferem significativamente nas propriedades de composição, morfologia, propriedades térmicas, reológicas e retrogradação. 7 O amido da batata inglesa exibe maior poder de inchamento...

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Structures of micelles formed by synthetic alkyl glycosides with unsaturated alkyl chains

Cited by 35 publications

References 29 publications

Unusual, pH-Induced, Self-Assembly Of Sophorolipid Biosurfactants

Unusual, pH-Induced, Self-Assembly Of Sophorolipid Biosurfactants

Carbohydrate-Based Surfactants: Structure-Activity Relationships

Novos surfactantes alquil poliglicosídicos à base de amilose extraída da batata inglesa (Solanum tuberosum l.)

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