Development of a mild method for the extraction of anthraquinones from their aluminum complexes in madder lakes prior to HPLC analysis

Sanyova, Jana; Reisse, Jacques

doi:10.1016/j.culher.2006.06.003

Cited by 76 publications

(42 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Milder extraction method which would minimize unwanted effects such as acid hydrolysis, decarboxylation or methylation, but still extract alizarin, purpurin and other colourants as quantitatively as possible were desirable. The use of hydrofluoric acid solutions for the extraction of anthraquinones from their aluminium complexes in madder lakes fulfilled the hope of non-destructive extraction of pseudopurpurin, glycosides and other labile molecules, and it proved to be at least as efficient as HCl for alizarin and purpurin [25].…”

Section: Introductionmentioning

confidence: 99%

“…In the same period, Kirby and White [23] suggested a method involving the use of a boron trifluoride/MeOH mixture for the extraction of lake pigment dyestuffs from paintings, and the same procedure was used a few years later [24] to extract dyestuffs from purple samples in a fifteenth century velvet panel. As Sanyova and Reisse [25] pointed out, one drawback of this method is the esterification of carboxyl-containing colourants, such as pseudopurpurin and munjistin. Milder extraction method which would minimize unwanted effects such as acid hydrolysis, decarboxylation or methylation, but still extract alizarin, purpurin and other colourants as quantitatively as possible were desirable.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Extracting natural dyes from wool—an evaluation of extraction methods

et al. 2011

View full text Add to dashboard Cite

The efficiency of eight different procedures used for the extraction of natural dyes was evaluated using contemporary wool samples dyed with cochineal, madder, woad, weld, brazilwood and logwood. Comparison was made based on the LC-DAD peak areas of the natural dye's main components which had been extracted from the wool samples. Among the tested methods, an extraction procedure with Na 2 EDTA in water/DMF (1:1, v/v) proved to be the most suitable for the extraction of the studied dyes, which presented a wide range of chemical structures. The identification of the natural dyes used in the making of an eighteenth century Arraiolos carpet was possible using the Na 2 EDTA/DMF extraction of the wool embroidery samples and an LC-DAD-MS methodology. The effectiveness of the Na 2 EDTA/DMF extraction method was particularly observed in the extraction of weld dye components. Nine flavone derivatives previously identified in weld extracts could be identified in a single historical sample, confirming the use of this natural dye in the making of Arraiolos carpets. Indigo and brazilwood were also identified in the samples, and despite the fact that these natural dyes were referred in the historical recipes of Arraiolos dyeing, it is the first time that the use of brazilwood is confirmed. Mordant analysis by ICP-MS identified the widespread use of alum in the dyeing process, but in some samples with darker hues, high amounts of iron were found instead.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Extracting natural dyes from wool—an evaluation of extraction methods

et al. 2011

View full text Add to dashboard Cite

show abstract

“…The study of historical red and yellow lakes (organic dyes precipitated on inert substrates or as insoluble complexes with suitable metal salts, in order to act as pigments) was pioneered in the 1990s at the National Gallery of Art in London [4] and more recently tackled at the KIK-IRPA in Brussels [12]. Interest in the characterisation of modern organic pigments has only gained momentum in the scientific literature in the last 10 years.…”

Section: Introductionmentioning

confidence: 99%

HPLC-DAD and HPLC-ESI-Q-ToF characterisation of early 20th century lake and organic pigments from Lefranc archives

et al. 2017

View full text Add to dashboard Cite

The characterisation of atelier materials and of the historical commercial formulation of paint materials has recently gained new interest in the field of conservation science applied to modern and contemporary art, since modern paint materials are subjected to peculiar and often unpredictable degradation and fading processes. Assessing the composition of the original materials purchased by artists can guide not only their identification in works of art, but also their restoration and conservation. Advances in characterisation methods and models for data interpretation are particularly important in studying organic coloring materials in the transition period corresponding to the late 19th-early 20th century, when many such variants or combinations were hypothetically possible in their formulations. There is thus a need for reliable databases of materials introduced in that period and for gaining chemical knowledge at a molecular level related to modern organic pigments, by state-of-the-art protocols. This paper reports on the results of a study on 44 samples of historical colorants in powder and paint tubes, containing both lake pigments and synthetic organic pigments dating from 1890 to 1926. The samples were collected at the Lefranc Archive in Le Mans (France) as a part of Project Futurahma "From Futurism to Classicism (1910Classicism ( -1922. Research, Art History and Material Analysis", (FIRB2012, Italian Ministry of University and Research), and were investigated using an analytical approach based on chromatographic and mass spectrometric techniques. The focus of the chemical analyses was to reveal the composition of the historical organic lake pigments including minor components, to discriminate between different recipes for the extraction of chromophore-containing molecules from the raw materials, and ultimately to distinguish between different formulations and recipes. High performance liquid chromatography (HPLC) with diode array detector (DAD) or electrospray-Quadrupole-Time of Flight tandem mass spectrometry detector (ESI-Q-ToF) were chosen given their considerable capacity to identify such complex and widespread organic materials. Although the inorganic components of the pigments were not taken into account in this survey, the specific molecular profiles provided invaluable information on the extraction procedures or synthetic strategy followed by the different producers, at different times. For instance, the use of Kopp's purpurin and garancine was highlighted, and synthetic by-products were identified. The results provided evidence that the addition of synthetic organic pigments to paint mixtures started from 1910 onwards, but they also suggest that in the formulation of high quality (surfin) colorants, natural products were still preferred. Moreover, in one of the samples the use of murexide as the colouring material was confirmed. This paper presents the first systematic and comprehensive survey on organic lakes and pigments belonging to an historical archive, by both HPLC-DAD and HPLC-ES...

show abstract

“…Naturalne barwniki organiczne w farbach istnieją bowiem w postaci tak zwanych laków, będących kompleksami substancji barwiących z metalami osadzonymi na nośnikach nieorganicznych 10,11 . W celu identyfikacji substancji barwiących należy najpierw wyizolować je z laku oraz ze spoiwa malarskiego, tak aby nie spowodować zmian w ich pierwotnej strukturze 12 . Tradycyjna metoda ekstrakcji substancji barwiących z farb i laków opierała się na zastosowaniu mieszaniny metanolu z wodnymi roztworami silnych kwasów nieorganicznych, takich jak kwas siarkowy (VI) lub kwas solny oraz prowadzeniu procesu w wysokiej temperaturze 13 ,…”

unclassified