Stabilization of Flavylium Dye by Incorporation into Bentonite Clay

Kohno, Yoshiumi; Hoshino, Ryo; Ikoma, Shuji; Shibata, Masashi; Matsushima, Ryoka; Tomita, Yasumasa; Maeda, Yoichiro; Kobayashi, Kenkichiro

doi:10.4011/shikizai.83.103

Cited by 9 publications

(9 citation statements)

References 22 publications

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“…It is reported that various dyes could be stabilized by their adsorption into the interlayer of clays 7,8,12,13) or pores of MPS 3,9,10) . However, AD dyes tend to decompose more easily than AN dyes as the sugar chain from anthocyanin has been removed by hydrolysis in the former.…”

mentioning

confidence: 99%

Anthocyanidin Dye and Al/Fe-Containing Mesoporous Silica Composites and their Color Properties

Lin

Saotome

Kohno

et al. 2013

Journal of the Japan Society of Colour Material

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confidence: 99%

Anthocyanidin Dye and Al/Fe-Containing Mesoporous Silica Composites and their Color Properties

Lin

Saotome

Kohno

et al. 2013

Journal of the Japan Society of Colour Material

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“…Thus, adsorption of the dyes onto the clay does not markedly reduce their photostability. On the other hand, there was substantial improvement in the thermal stability of both FL1 and FL2 adsorbed on palygorskite, as has been reported for flavylium cations adsorbed on other types of clay (Kohno et al, 2007(Kohno et al, , 2010 or protonated zeolites . A temperature of 120 o C. was chosen for the thermal stability tests since temperatures up to 120-150 o C have been used for the thermal analysis sepiolite/indigo and PAL/indigo hybrid materials and, in the case of PAL (Guggenheim and Koster van Gross, 2001), this temperature is just above the range where most of the weakly adsorbed water has been lost and where the more strongly adsorbed water only begins to be lost.…”

Section: Stability Tests Of the Hybrid Pigmentssupporting

confidence: 72%

“…In order to prevent the hydration-dependent loss of color of anthocyanins, as well as improve photo and thermal stabilities, researchers have tried to isolate or encapsulate the anthocyanins in an environment that prevents external contacts. Indeed, the inclusion of synthetic analogues of anthocyanins (flavylium cations) in inorganic matrices such as mesoporous materials (Kohno et al, 2011), zeolites (Kohno et al, 2008) and clays (Kohno et al, 2010(Kohno et al, , 2007, as well as in supramolecular and colloidal systems, such as cucurbiturils and anionic micelles (Lima et al, 2002), represent promising alternatives for preventing the undesirable chemistry of these dye molecules.…”

Section: Anthocyaninsmentioning

confidence: 99%

“…The inclusion and/or adsorption of anthocyanins and flavylium cations in/on inorganic substrates such as mesoporous materials (Kohno et al, , 2011(Kohno et al, , 2015Gago et al, 2017) and clays (Lima et al, 2007;Kohno et al, 2007Kohno et al, , 2010Ogawa et al, 2017;Ribeiro et al, 2018) previous studies of the group and the syntheses have been previously reported . The palygorskite used in this work was the Source Clay PFl-1 from the Clay Minerals Society.…”

Section: Introductionmentioning

confidence: 98%

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Hybrid pigments from fibrous clays and chromophores inspired by the color of fruits, flowers and wine

Silva¹

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Features such as color, brightness, fluorescence and stability are extremely important in applications of pigments. Anthocyanins, the natural pigment responsible for most of the purple, blue and red colors of flowers and fruits, have great potential for practical applications as dyes or antioxidants. However, these applications are limited by their chemical reactivity, which is affected by several factors, including pH, temperature, light, and oxygen, among others. Hybrid materials inspired by the ancient Maya Blue pigment are a promising alternative to improve the properties and applicability of natural and synthetic dyes. Flavylium cations serve as models for the chemical and photochemical reactivity of anthocyanins. Likewise, pyranoflavylium cations serve as models of the fundamental chromophoric moiety of pyranoanthocyanins, molecules that can form from reactions of the grape anthocyanins in red wines during their maturation. Fibrous clays, constituents responsible by the excellent stability of Maya blue pigment, have channels that can potentially allow partial or full insertion of these dyes molecules. Therefore, in the present thesis, hybrid pigments were prepared by the adsorption of a series of synthetic flavylium cations and synthetic pyranoflavylium cations on the fibrous clays palygorskite and sepiolite and their photophysical properties and stability were evaluated. The observation of biexponential fluorescence decays is consistent with emission from dye molecules adsorbed at two distinct sites on the fibrous clays. The fluorescence properties of dye molecules can be improved, depending on the amount of dyes adsorbed on the clay, by the formation of dye/clay hybrids. The color of the adsorbed dye molecules was somewhat more resistant to changes in external pH, photochemical stability was maintained and the thermal lability was markedly improved. Besides the development of novel hybrid flavylium cation/fibrous clay, we have achieved advances in the stabilization of these dye molecules, with regard mainly to the pH-dependent equilibrium and thermal treatment. In addition, the present work represents the first systematic study of hybrid materials prepared from pyranoflavylium cations. Therefore, the results obtained here definitively point to flavylium cations and pyranoflavylium cations as promising chromophores and fibrous clays as promising substrates for the development of novel, highly fluorescent hybrid pigments with attractive colors and marked chemical and thermal stability.

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“…Besides, there are many studies that have reported the stability enhancement of the dye by complexing with an inorganic host such as clays 5 ) , mesoporous silica 6 ) or zeolite 7 ) . We have also investigated the stability enhancement of natural dyes by complexing with several inorganic substances having layered structure, such as hydrotalcite and montmorillonite 8,9) . The stability of dyes improved by intercalating the dye between the layers of the host materials.…”

Section: ．Introductionmentioning

confidence: 99%

Stabilization of Cu-Chlorophyllin by Incorporation into Hydrotalcite Interlayer

Katsura

Shibata

Kohno

et al. 2020

Journal of the Japan Society of Colour Material

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The stability of copper chlorophyllin dye, a derivative of the naturally occurring chlorophyll, was improved by the intercalation into the interlayer space of a layered inorganic host material. As the layered inorganic compounds, hydrotalcite was used. The copper chlorophyllin could be inserted between the layers either by the reconstruction method or by the ion exchange method. We found the preparation condition for the composite materials that successfully included the dye molecules between the layers. The obtained composite samples showed high durability under visible light irradiation. The intercalation of the copper chlorophyllin into the hydrotalcite layers effectively suppressed the elution of the dye molecules by water or ethanol. We proposed the potential application of these highly stable composite materials as environmentally friendly natural dye-based colorants.

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Stabilization of Flavylium Dye by Incorporation into Bentonite Clay

Cited by 9 publications

References 22 publications

Anthocyanidin Dye and Al/Fe-Containing Mesoporous Silica Composites and their Color Properties

Anthocyanidin Dye and Al/Fe-Containing Mesoporous Silica Composites and their Color Properties

Hybrid pigments from fibrous clays and chromophores inspired by the color of fruits, flowers and wine

Stabilization of Cu-Chlorophyllin by Incorporation into Hydrotalcite Interlayer

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