Tailor‐made carbohydrate surfactants? Systematic investigations into structure‐property relationships of N‐Acyl N‐Alkyl 1‐Amino‐1‐Deoxy‐D‐Glucitols

Doren, V. E. Van

doi:10.1002/9783527614899.ch14

Cited by 9 publications

(8 citation statements)

References 31 publications

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“…This Kraft temperature depends on the polarity of the solvent as well as the nonpolar chain of the surfactant. 24 With increase in reaction temperature, the solubility of CTAB increases, resulting in enhanced probability of micelle formation. The second reason for the increase in the rate of reaction with temperature is the activation energy.…”

Section: Resultsmentioning

confidence: 99%

Surfactant-Induced Anion Exchange and Morphological Evolution for Composition-Controlled Caesium Lead Halide Perovskites with Tunable Optical Properties

2019

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Environmentally stable lead halide perovskite nanostructures with engineered composition and morphology are attractive because of their exotic optical properties. Here, we report the synthesis of monodispersed (∼20 nm) CsPbI 3 cubic perovskite nanocrystals (NCs) using edible olive oil as a solvent as well as a chelating reagent. Thereafter, bromide anion exchange reaction using the cetyl trimethyl ammonium bromide surfactant in hexane is carried out at relatively lower temperatures to synthesize caesium lead halide perovskites with variable halide compositions and tunable band gaps. Interestingly, because of the formation of micelles, continuous morphology evolution varying from NCs of different sizes to nanowires (NWs) and nanosheets is observed. The anion exchange temperature has a distinct effect on the morphology of the CsPbBr 3 nanostructure and the anion exchange reaction rate. Finally, an easy solution-processed photoconductive device is demonstrated using as-grown CsPbBr 3 NWs, indicating its potential for optoelectronic applications.

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Section: Resultsmentioning

confidence: 99%

Surfactant-Induced Anion Exchange and Morphological Evolution for Composition-Controlled Caesium Lead Halide Perovskites with Tunable Optical Properties

2019

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“…Since the development of the technology of manufacturing alkyl glucamides by the Procter & Gamble Company (3,4), glucamides were used in consumer products and generated intensive interest both in academic and industrial organizations. van Doren (5) reported his work on N-acyl-N-alkyl-1-amino-1-deoxy-D-glucitols (number of carbon atoms in the acyl group: n = 0-5) and constructed a model based on the relationship between the total number of hydroxyl/ carbonyl groups, the total number of carbon atoms in the acyl and alkyl chain, and the lyotropic mesophase for predicting behavior of these compounds such as Krafft temperature, critical micelle concentration (CMC), and toxicity. Other work investigated their solid and liquid crystal structures and gel formation in aqueous solution (6)(7)(8)(9).…”

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confidence: 99%

Surface properties of N‐alkanoyl‐N‐methyl glucamines and related materials

Zhu

Rosen

Vinson

et al. 1999

J Surfact & Detergents

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The surface properties [effectiveness of surface tension reduction (γ CMC ), critical micelle concentration (CMC), efficiency of surface tension reduction (pC 20 ), maximal surface excess concentration (Γ max ), minimal area/molecule at the interface (A min ), and the (CMC/C 20 ) ratio] of some well-purified N-alkanoyl-N-methyl glucamines and related polyol-based Nmethyl amide-type surfactants, having the structural formula RC(O)N(Me)CH 2 (CHOH) x CH 2 OH, where RC(O) = undecanoyl, lauroyl, tridecanoyl, myristoyl, and x = 1, 3, and 4, were investigated at 25°C in distilled water and 0.1 M NaCl. Water solubility of these compounds does not simply depend on the number of hydroxyl groups in the molecule but is associated with the balance between intermolecular hydrogen bonds and hydrogen bonds formed with water molecules. The fundamental interfacial properties, such as CMC and γ CMC , and two thermodynamic parameters, standard free energy of adsorption and standard free energy of micellization, were found to be significantly dependent on the hydrophobic acyl chain rather than on the number of CHOH groups in the hydrophilic moieties. By contrast, the practical performance properties were greatly dependent on the nature of the hydrophilic group. As a whole, these surfactants had desirable foaming properties and efficient wetting abilities. Furthermore, synergism in foaming and wetting abilities was observed in a binary mixture of these surfactants with an alkyloxyethylene sulfate.

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“…For noncyclic polar heads, T K increases with the number of alcohol units and the stereoregularity of the alcohols (Laughlin et al, ). An increase in the size of the polar headgroup was found to decrease the T K in most of the cases (Burczyk et al, ; Van Doren, ) but, in some specific cases, can increase the T K (Hato, ). While these trends are already a useful qualitative guide to target water‐soluble surfactants, no predictive method is available to help rationalization and prescreening of sugar‐based surfactants prior to any synthesis.…”

Section: Introductionmentioning

confidence: 99%

Anticipating Dissolution Issues of Sugar‐Based Surfactants through a Decision Tree Approach

Gaudin

Fayet

Rotureau

et al. 2018

J Surfact & Detergents

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Sugar‐based surfactants are renewable alternatives to petroleum‐based surfactants in many applications such as detergents and cosmetics. However, their molecular structure often gives rise to relatively stable crystals, which can lead to difficulties in dissolving them in water. This phenomenon is characterized by the Krafft temperature (T K), above which the surfactant solubility becomes high enough to induce self‐association into micelles. Small changes in the molecular structure can result in large T K differences, which make rationalization and prediction of T K challenging. Few models were proposed in the literature, but none of them are applicable to sugar‐based surfactants. In this article, we propose two decision tree models to estimate whether sugar‐based surfactants exhibit potential dissolution issues at room temperature (i.e., T K above 25 °C or not). The first one, based on the descriptors of the whole molecule including quantum‐chemical ones, was able to correctly classify 86% of the surfactants in the validation set. The second one, built from simple structural counts of the polar headgroup and the alkyl chain, could predict the right class for 78% of the surfactants in the validation set. These classification models account for experimentally known trends between the molecular structure and T K, such as the impact of the polar headgroup size, the alkyl chain length, and the presence of an amide linkage. To the end, our models were applied to a practical case to show how they can help in designing synthesis procedures of new surfactants.

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Tailor‐made carbohydrate surfactants? Systematic investigations into structure‐property relationships of N‐Acyl N‐Alkyl 1‐Amino‐1‐Deoxy‐D‐Glucitols

Cited by 9 publications

References 31 publications

Surfactant-Induced Anion Exchange and Morphological Evolution for Composition-Controlled Caesium Lead Halide Perovskites with Tunable Optical Properties

Surfactant-Induced Anion Exchange and Morphological Evolution for Composition-Controlled Caesium Lead Halide Perovskites with Tunable Optical Properties

Surface properties of N‐alkanoyl‐N‐methyl glucamines and related materials

Anticipating Dissolution Issues of Sugar‐Based Surfactants through a Decision Tree Approach

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