‘Naturalization’ of textile disperse dyes through glycoconjugation: the case of a bis(2-hydroxyethyl) group containing azo dye

Bianchini, Roberto; Catelani, Giorgio; Cecconi, Riccardo; D’Andrea, Felicia; Frino, Elena; Isaad, Jalal; Rolla, Massimo

doi:10.1016/j.carres.2008.02.009

Cited by 28 publications

(22 citation statements)

References 8 publications

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“…By this approach, the above-mentioned selectivity trend in chromogenic anion sensing is altered and thus selective choromogenic probe of a cyanide anion in pure water is demonstrated. The water solubility of the organic chemosensor is given by its glycoconjugation with the usual saccharides [29][30][31][32][33]. Cyanide is expected to be detectable by nucleophilic attack toward hydrazone functional group, which is activated by an intramolecular hydrogen-bond.…”

Section: Introductionmentioning

confidence: 99%

A novel glycoconjugated N-acetylamino aldehyde hydrazone azo dye as chromogenic probe for cyanide detection in water

Isaad

Achari

2011

Analytica Chimica Acta

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confidence: 99%

A novel glycoconjugated N-acetylamino aldehyde hydrazone azo dye as chromogenic probe for cyanide detection in water

Isaad

Achari

2011

Analytica Chimica Acta

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“…The results of a correlated, contemporary study of this compound have been reported in the literature. [9] As described in our previous papers, we proceeded to glycoconjugate the azo dyes with lactose or with its monosaccharidic components, glucose and galactose, through ester [10,11] or ether [12,13] spacers bonded between the glycosidic moiety and the dye. The different glycol-azo dyes (GADs) synthesised are soluble in water and are multipurpose as they dye all the fabrics that we tested: wool, silk, nylon, polyester, acrylic and acetate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Water‐Soluble Large Naturalised Dyes Through Double Glycoconjugation

2009

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Recently we started to develop a new class of dyes based upon the glycoconjugation of disperse dyes with mono-or disaccharides. We used the term "naturalised" to describe these dyes because we used natural lactose in the glycoconjugation process, and also because they are similar to real natural dyes, the hydrosolubility of which is based upon the saccharidic moiety attached to the chromophore, as in carminic acid or carthamin. Synthetic dyes submitted to the process of naturalisation consist of small chromophoric molecules, prevalently azoic, whereas larger dye molecules with a higher mass did not show appreciable solubility in water

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“…8 The reaction mixture was stirred at room temperature overnight, then water (20 mL) and ether (20 mL) were added to the crude solution and the aqueous phase was separated and extracted with Et 2 O (2 Â 20 mL). The organic phases were combined and dried over Na 2 SO 4 , filtered, and concentrated under reduced pressure.…”

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“…The subsequent S N 2 displacement with sodium azide and the final hydrogenolysis afforded 6 0 -amino-lactose-triacetonide 4 in 80% yield over three steps (Scheme 2). 8 The coupling of the elaborated dye and saccharide moieties was carried out using as the acid activating reagent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM), prepared in situ by reaction of 2-chloro-4,6-dimethoxy-1,3,5-triazine with N-methyl morpholine.…”

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“…Both glutamic diester derivatives 1d and 2d were hydrolysed to dicarboxylic acids 1e and 2e completing the elaboration of dyes 1a and 2a (Scheme 1). The naturalising lactose derivative 4 was prepared through a straightforward elaboration 8 of lactose-triacetonide 3, synthesised from lactose according to a well established protocol. 9 Toluensulfonyl chloride was employed to regioselectively introduce a good leaving group on the primary hydroxyl group of 3.…”

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Efficient double glycoconjugation to naturalize high molecular weight disperse dyes

Bianchini

Rolla

Isaad

et al. 2012

Carbohydrate Research

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a b s t r a c tCommercially available Disperse Orange 29 (1a) and Disperse Red 1 (2a) were elaborated to glycoconjugated species, following a new version of a previously-described 'naturalisation' procedure. Glutamic acid was chosen to achieve a double glycoconjugation, which is essential to give to the original disperse dye a water solubility suitable for reaching optimal dyeing conditions. UV-vis plot of the 'naturalised' species showed negligible differences when compared to those of the commercial dyes.Ó 2011 Elsevier Ltd. All rights reserved.The naturalisation of dyes 1 (i.e., the conjugation of dyes to saccharide species) has proven to be a valid method to prepare novel dyeing agents. The main characteristics of these dyes are not only their solubility in water, but also their ability to dye the majority of synthetic and natural (wool, cotton) textiles. 2 Moreover this property is accompanied by the environmentally sound characteristic: the overall process of dyeing does not require surfactants, mordants, dispersing agents or other additives, generally required to yield a good permeation of the dye into the fabrics. 3A limitation of the solubilising power of the saccharidic unit when conjugated with the dye, is that the molecular weight of the two portions must remain similar. 4 We have observed that large molecular sized dyes do not reach an acceptable hydrosolubility when glycoconjugated with a single lactose unit, despite the presence of a variety of linkers such as esters, ethers, amides, alkylamino derivatives and mixed ethereal-esters, or amido-esters. 4 To extend the field of application of this new type of dyeing agent, we studied a double glycoconjugation with lactose, bonded through a difunctional linker to the chromophore. This should enhance the solubilising power of the saccharide according to the molecular weight of the dye.As a first example of this approach we recently prepared malonic acid derivatives.1c,d Herein, we highlight that glutamic acid is a particularly convenient functionality to link chromophoric moieties to saccharides in the form of water soluble dyes. The procedure allows the preparation of new materials able to dye and to reduce the environmental impact of the waste produced by dyeing.

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‘Naturalization’ of textile disperse dyes through glycoconjugation: the case of a bis(2-hydroxyethyl) group containing azo dye

Cited by 28 publications

References 8 publications

A novel glycoconjugated N-acetylamino aldehyde hydrazone azo dye as chromogenic probe for cyanide detection in water

A novel glycoconjugated N-acetylamino aldehyde hydrazone azo dye as chromogenic probe for cyanide detection in water

Synthesis of Water‐Soluble Large Naturalised Dyes Through Double Glycoconjugation

Efficient double glycoconjugation to naturalize high molecular weight disperse dyes

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