Structure/function correlation of thixotropic additives based on three leaf-like triamide derivatives containing three alkyl-chains

Nakagawa, Yuto; Watahiki, Kaede; Okano, Rei; Satou, Eiichi; Shibasaki, Yuji; Fujimori, Atsuhiro

doi:10.1016/j.colsurfa.2019.04.094

Cited by 9 publications

(26 citation statements)

References 45 publications

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“…1 C 18 (OH)‐Fc‐A synthesized based on R ‐12‐HSA is a promising candidate for a thixotropic additive/gelling agent. A comparative study with 2 C 18 (OH)‐Hx‐dA and 3 C 18 (OH)‐Pb‐tA evaluated in a previous study provided useful information [44,45] . In particular, the comparison in the extremely thin structure of a monolayer clearly showed the hydrogen bonding position, crystallinity, and nanofiber formation characteristics of the corresponding molecules.…”

Section: Resultsmentioning

confidence: 80%

“…Figure 1(b) shows the surface morphology observation results obtained by atomic force microscopy (AFM) measurement when these monolayers on the water surface were transferred onto a solid substrate by the upstroke process of the LB method. In a previous report, monolayers of 2 C 18 (OH)‐Hx‐dA and 3 C 18 (OH)‐Pb‐tA showed mesoscopic nanofiber morphology due to the influence of intermolecular hydrogen bonds [44,45] . The 1 C 18 (OH)‐Fc‐A monolayer transferred at 30 mN⋅m –1 showed a densely assembled morphology of nanofibers and formed an aggregated structure of homogeneous height.…”

Section: Resultsmentioning

confidence: 80%

“…It undulates like a spiral form and takes a twisted state. The diamide with two‐chain and triamide with three‐chain derivatives formed clear helical fibers when observed using AFM or transmission electron microscopy (TEM) [44,45] . 1 C 18 (OH)‐Fc‐A shows an undulating morphology similar to that of the raw material R ‐12‐HSA, but the individual fibers appear to be more separated.…”

Section: Resultsmentioning

confidence: 99%

“…The horizontal axis value in this figure is standardized to the average limiting area per hydrophobic chain. Because the hydrophobic tris(4‐aminophenyl) benzene core part of the triamide derivative with three hydrocarbons is bulky, the collapsed surface pressure is as low as 10 mN⋅m −1 and the limiting area is 130 Å 2 [45] . The diamide derivative with two hydrocarbons exhibits stable condensed monolayer behavior because the hexamethylenediamine linker moiety is flexible, and the limiting area is maintained at 50 Å 2 [44] .…”

Section: Resultsmentioning

confidence: 99%

“… (a) π‐A isotherms of a monolayer on the water surface of 1 C 18 (OH)‐Fc‐A, 2 C 18 (OH)‐Hx‐dA, and 3 C 18 (OH)‐Pb‐tA (15 °C). (b) AFM images of a monolayer on solid of 1 C 18 (OH)‐Fc‐A, 2 C 18 (OH)‐Hx‐dA, [44] and 3 C 18 (OH)‐Pb‐tA [45] …”

Section: Resultsmentioning

confidence: 99%

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Characterization of Molecular Arrangement of Long‐chain Ferrocenyl Derivatives Having Asymmetric Carbon by Method of Organized Molecular Films and Formation of Its Helical Nanofibers

et al. 2021

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Formation of organized molecular film and helical nanofibers of ferrocene derivatives having R‐12‐hydroxystearyl chains with asymmetric carbon was investigated. The 12‐hydroxystearyl chain, which induces “thixotropy” due to the formation and breakage of intermolecular hydrogen bonds, was introduced into the ferrocenyl unit. The structure of this derivative as a monolayer on the water surface and its Langmuir‐Blodgett (LB) film properties were analyzed. The monolayer showed a two‐dimensional phase transition, corresponding to the formation of fibrous morphology. In the LB multilayers, intermolecular hydrogen bonding between hydroxyl groups at the 12‐position of the chain and crystalline packing was observed. Raman mapping revealed the difference in surface morphology of each derivative depending on the number of 12‐hydroxystearyl chains. The derivative having the single chain showed a right‐handed helical morphology in the film and this behavior is similar to those having two and three chains. In circular dichroism spectra, the film showed a positive Cotton effect. Since the helical chains easily entangle with each other to form a sponge‐like organization, it was expected that the solvent uptake was the origin of gelation induction to its contact solvent.

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Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Characterization of Molecular Arrangement of Long‐chain Ferrocenyl Derivatives Having Asymmetric Carbon by Method of Organized Molecular Films and Formation of Its Helical Nanofibers

et al. 2021

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Correlation between Chirality and Spherical Particle Formation Related to the Loss of Function of Thixotropic Additive Molecules

2022

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The relationship between chirality and loss of function of thixotropic additive molecules with asymmetric carbon and helical fiber growth under high‐temperature exposure was investigated. Among the thixotropic additive molecules that impart gelation/fluidization ability during pressurization of the solvent, derivatives with high‐performance, helical fiber growth ability became mesoscopic spherical particles upon high‐temperature exposure. Conversely, derivatives that lost their fiber growth ability could not achieve solvent gelation. The growth pattern was such that the helical fibers were transformed into straight fibers. The right‐handed helical signal of the circular dichroism spectrum, which is indicative of chirality by structure formation, was inactivated upon high‐temperature exposure. Therefore, a low‐temperature process or heat treatment in an inert state under a N2 atmosphere is essential for maintaining chirality and helical fibrosis.

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Characterization of Coating Films of Thixotropic Solvent Gel Containing Organo‐modified Nanodiamonds

et al. 2023

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A gelation solvent containing a diamide-based thixotropic additive with two hydrocarbons and organo-modified nanodiamonds was prepared and evaluated herein as a coating film. Nanodiamonds were introduced into a solvent containing diamide-based thixotropic additive molecules with 12-hydroxystearyl chains which were uniformly dispersed due to organic chain modification on the outermost layer surface. In addition to common solvents including toluene, ethyl cetyl hexanoate, a cosmetic emollient, forms nanodiamond-containing gels. The helical nanofibers formed by the diamide-based thixotropic additive molecule with two hydrocarbons in the gel showed affinity for the organo-modified nanodiamonds, and the contact morphology between the nanofibers and nanodiamond particles was confirmed. Nanodiamonds exhibited a denaturation effect on biomolecules adsorbed on their surfaces. Overall, nanodiamond-containing emollient gels are expected to exhibit antibacterial properties against viruses and malodorous bacteria on skin as part of thixotropic immobilization films for cosmetic powders.

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Structure/function correlation of thixotropic additives based on three leaf-like triamide derivatives containing three alkyl-chains

Cited by 9 publications

References 45 publications

Characterization of Molecular Arrangement of Long‐chain Ferrocenyl Derivatives Having Asymmetric Carbon by Method of Organized Molecular Films and Formation of Its Helical Nanofibers

Characterization of Molecular Arrangement of Long‐chain Ferrocenyl Derivatives Having Asymmetric Carbon by Method of Organized Molecular Films and Formation of Its Helical Nanofibers

Correlation between Chirality and Spherical Particle Formation Related to the Loss of Function of Thixotropic Additive Molecules

Characterization of Coating Films of Thixotropic Solvent Gel Containing Organo‐modified Nanodiamonds

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