Mass spectrometric analysis of sulphonated dyes based on diaminobiphenyls

Volná, Kateřina; Holčapek, Michal; Suwanruji, Potjanart; Freeman, Harold S.

doi:10.1111/j.1478-4408.2006.00001.x

Cited by 9 publications

(7 citation statements)

References 16 publications

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“…The full scan mass spectra cannot provide enough information for identification and they may be also influenced by the different type and relative abundances of adducts due to varying content of salts in the solution and differences among the geometries of ion sources from different vendors. The full scan mass spectra library provides supplementary information for the confirmation of MW determination, especially for polysulfonated/polysulfated dyes, because their full scan mass spectra are rather complex,1, 2, 28, 29 containing series of multiply charged ions [M–xH] x− and [M–(x+y)H+yNa] x− . The second library also contains supplementary information, such as MWs, Color Index (C.…”

Section: Resultsmentioning

confidence: 99%

Comparison of negative ion electrospray mass spectra measured by seven tandem mass analyzers towards library formation

Volná

Holčapek

Kolářová

et al. 2007

Rapid Comm Mass Spectrometry

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A library of negative ion electrospray ionization mass spectra and tandem mass spectra (MS/MS) of sulfonated dyes has been developed for fast identification purposes. The uniform protocol has been elaborated and applied to the measurements of more than 50 anionic dyes. Three collision energies are selected in our protocol which ensures that at least one of them provides a suitable ratio of product ions to the precursor ion. The robustness is investigated with altered values of tuning parameters (e.g. the pressure of the nebulizing gas, the temperature and the flow rate of drying gas, and the mobile phase composition). The results of the inter-laboratory comparison of product ion mass spectra recorded on seven different tandem mass spectrometers (three ion traps, two triple quadrupoles and two hybrid quadrupole time of flight instruments) are presented for four representative anionic dyes--azo dye Acid Red 118, anthraquinone dye Acid Violet 43, triphenylmethane dye Acid Blue 1 and Al(III) metal-complex azo dye. The fragmentation patterns are almost identical for all tandem mass analyzers, only the ratios of product ions differ somewhat which confirms the possibility of spectra transfer among different mass analyzers with the goal of library formation.

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Section: Resultsmentioning

confidence: 99%

Comparison of negative ion electrospray mass spectra measured by seven tandem mass analyzers towards library formation

Volná

Holčapek

Kolářová

et al. 2007

Rapid Comm Mass Spectrometry

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“…The reactive dyes were analysed using negative‐ion electrospray ionisation (ESI)‐MS. As indicated in Scheme 6, the spectra obtained were characterised by signals arising from [M − x Na]/ z ions plus fragment ions produced by cleavage at C–N bonds adjacent to the azo linkage [20]. In the case of dye 1 , the loss of both sodium ions from the parent structure gave m/z = 561 ( z = 2) as the pseudo‐molecular ion.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and application of easy wash‐off reactive dyes

Suwanruji

Freeman²

2006

Coloration Technology

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New dyes that not only give good fixation levels but also relatively low substantivity in the hydrolysed form were the targets of this research. Our approach involved lowering the substantivity of the hydrolysed dye by reducing the planarity that is required for dyes to have high substantivity on cotton. In this regard, bifunctional bis‐dichlorotriazine (bis‐DCT) and tetrafunctional bis‐monochlorotriazine/bis‐sulphatoethyl sulphone [bis‐(MCT/SES)] reactive dyes were made, using selected diaminobiphenyls. Bis‐DCT bifunctional reactive dyes were applied to cotton by a pad–batch method, while bis‐(MCT/SES) tetrafunctional reactive dyes were applied to cotton by a pad–dry–cure. Following dye application, it was found that the resultant hydrolysed dyes easily washed off the fibre surface and that the dyed cotton fabrics had colour fastness to rubbing and laundering properties that were comparable with the commercial prototypes used in this study. However, it is also apparent that the combination of relatively low water solubility and large molecular size has an adverse effect on fibre penetration.

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“…Liquid chromatography‐mass spectrometry (LC‐MS) is a very sensitive technique for the analysis of anionic dyes, and negative electrospray ionisation (ESI) is considered the best method of ionisation . In liquid chromatography, a reversed phase medium with an ion‐pairing reagent is mainly used for the retention and separation of sulphonated dyes.…”

Section: Introductionmentioning

confidence: 99%

Dimerised heterobifunctional reactive dyes. Part 1: characterisation using quadrupole time‐of‐flight mass spectrometry

Sultana

Liu

Szymczyk

et al. 2018

Coloration Technology

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As part of an approach to enhancing the efficiency of reactive dye adsorption on cellulosic fibres at low electrolyte levels, commercially available dyes were dimerised using hexamethylenediamine (HMDA) as a linking group. A key component of this work involved using high-resolution mass spectrometry (HRMS) to characterise a group of polysulphonated heterobifunctional monochlorotriazine/vinyl sulphone reactive dyes (CI Reactive Yellow 176, CI Reactive Red 239, CI Reactive Blue 221, CI Reactive Red 194 and CI Reactive Blue 222) and their dimeric analogs. In this respect, dimeric dye ions of differently charged states were observed using HRMS-negative electrospray ionisation in combination with quadrupole time-of-flight mass spectrometry. For example, HRMS showed that the HMDA-linked reaction products were mixtures of the target (unhydrolysed) dimers, hydrolysed dimers, monoreacted products and hydrolysed unreacted dyes, with CI Reactive Yellow 176 and CI Reactive Red 194 producing the desired unhydrolysed dimers.

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Mass spectrometric analysis of sulphonated dyes based on diaminobiphenyls

Cited by 9 publications

References 16 publications

Comparison of negative ion electrospray mass spectra measured by seven tandem mass analyzers towards library formation

Comparison of negative ion electrospray mass spectra measured by seven tandem mass analyzers towards library formation

Design, synthesis and application of easy wash‐off reactive dyes

Dimerised heterobifunctional reactive dyes. Part 1: characterisation using quadrupole time‐of‐flight mass spectrometry

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