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Gewählte Publikation:

Jaxel, J; Amer, H; Bacher, M; Roller, A; Guggenberger, M; Zwirchmayr, NS; Hansmann, C; Liebner, F.
(2020): Facile synthesis of 1-butylamino- and 1,4-bis(butylamino)-2-alkyl-9,10-anthraquinone dyes for improved supercritical carbon dioxide dyeing
DYES PIGMENTS. 2020; 173, 107991 FullText FullText_BOKU

Supercritical carbon dioxide (scCO(2)) has recently been conquering both material sciences and process engineering owing to its intriguing properties like high diffusivity and tuneable (de)solubilizing performance. However, except for impregnation with biocidal preservatives, utilization of scCO(2) for modification of wood including dyeing has been hitherto less explored. Therefore, we recently proposed a green wood dyeing approach that relies on the excellent carrier medium properties of CO2 for non-polar disperse dyes in supercritical conditions and their reversion when leaving the supercritical state. However, using a common disperse dye of the 9,10-anthraquinone family (Disperse Blue, DB-134) without the addition of co-solvent, only a moderate colour change was obtained for the interior of small wood cuboids (1 cm x 1 cm x 2 cm) even after extensive variation of scCO(2) process conditions. Insufficient solubility of the dye in scCO(2) was assumed to be a major hindrance for homogeneous wood dyeing. Therefore, we synthesized a variety of 1-n-butylamino- and 1,4-bis(n-butylamino)-9,10-anthraquinone derivatives carrying different alkyl moieties in 2-position, which was confirmed to improve scCO(2) solubility. Instead of a previously reported seven-step synthesis affording moderate yields only (60% on average), we propose an alternate much simpler synthesis comprising of Marschalk alkylation (2-position) and a sequence of tosylation and n-alkylamination (1-position). The latter proved to pave way to a wide variety of colours and disperse dyes of improved solubility in scCO(2). Moreover, all products were characterized by various techniques including liquid-state H-1 and C-13 NMR and X-ray crystallography. Complementing X-ray diffraction, quantum-mechanical simulations were performed to predict or confirm conformation and colour of selected compounds.
Autor/innen der BOKU Wien:
Amer Hassan
Bacher Markus
Guggenberger Matthias
Hansmann Christian
Liebner Falk
Zwirchmayr Nele Sophie
BOKU Gendermonitor:

Find related publications in this database (Keywords)
Supercritical carbon dioxide dyeing
Anthraquinone disperse dyes
Colouring of massive wood
Marschalk alkylation
Alkylamination of 1-hydroxy- and 1,4-dihydroxyanthraquinone derivatives

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