1,5‐Dihydroxy‐4,8‐diamino‐ and 1,8‐dihydroxy‐4,5‐diaminoanthraquinone‐β‐ethers and thioethers. Blue dyes for synthetic polymer fibres

Peters, A. T.

doi:10.1002/jctb.280480204

Cited by 4 publications

(2 citation statements)

References 11 publications

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“…Thus, various anthraquinone derivatives can be used as dyes, e.g., mordant, vat dyes or in the printing processes. Anthraquinone derivatives like β-thio or β-phenol substituted 1,8-dihydroxy-4,5-diaminoanthraquinone exhibited a high affinity for polymer fibers like polyesters and produce a blue-greenish color [94]. Their high color fastness and also their stability against heat and oxidizing agents make anthraquinone dyes no longer conceivable.…”

Section: Paintings and Textilesmentioning

confidence: 99%

Polymers and Dyes: Developments and Applications

2015

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Amongst functional macromolecules, the combination of polymers and dyes is a research field of great potential with regard to high-performance materials. Accordingly, colored polymers have become increasingly important as materials for miscellaneous technical applications in recent years while also being a major part of everyday life. For instance, dye-containing polymers are nowadays widely applied in medicine, painting industries, analytics and gas separation processes. Since these applications are obviously connected to the dye's nature, which is incorporated into the corresponding polymers, the affinity of certain polymers to dyes is exploited in wastewater work-ups after (textile) dyeing procedures. In this review, we wish to point out the great importance of dye-containing polymers, with a comprehensive scope and a focus on azo, triphenylmethane, indigoid, perylene and anthraquinone dyes. Since a large number of synthetic approaches towards the preparation of such materials can be found in the literature, an elaborated overview of different preparation techniques is given as well.

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Section: Paintings and Textilesmentioning

confidence: 99%

Polymers and Dyes: Developments and Applications

2015

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“…Anthraquinone dyes play an important role in textile dyeing, plastics, biology, medicine and electrochemistry and photochemistry, not least due to their relatively high thermal, chemical and light stability. Depending on the position and nature of substituents, a broad colour spectrum can be achieved .…”

Section: Introductionmentioning

confidence: 99%

Click‐coupling of anthraquinone dyes with β‐cyclodextrin: formation of polymeric superstructures

Lievenbrück

Hartlaub

Ritter

2016

Polymer International

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Two novel cyclodextrin-modified anthraquinone dyes were synthesized and investigated for their complexation behaviour and formation of superstructures. Therefore, 1-fluoro-4-N-(propargylamino)anthraquinone and 1,4-bis(propargyloxy)anthraquinone were prepared via nucleophilic aromatic displacement and subsequently covalently 'click-coupled' in a copper(I)-catalysed azide-alkyne cycloaddition with -cyclodextrin monoazide. Both the propargyl-modified precursor and the click-coupled anthraquinone dyes were evaluated as hosts and guests, respectively, in -cyclodextrin interactions. The anthraquinone dye bearing two cyclodextrins, compound 1-fluoro-4-(((1--cyclodextrin-1H-1,2,3-triazol-5-yl)methyl)amino)anthraquinone can be supramolecularly linked to 11 resulting in coloured polymers. These features of -cyclodextrin-linked anthraquinone dyes can be verified with either 1 H 1 H NMR rotating frame nuclear Overhauser effect spectroscopy or the naked eye. 1,4-bis((1--cyclodextrin-1H-1,2,3-triazol-5-yl)methoxy)anthraquinone, enables the reversible formation of supramolecular crosslinked poly[(N,N-dimethyl acrylamide)-co-(N-(ferrocenoylmethyl)acrylamide)] (11), whereas the monofunctionalized

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ChemInform Abstract: 1,5‐Dihydroxy‐4,8‐diamino‐ and 1,8‐Dihydroxy‐4,5‐diaminoanthraquinone β‐Ethers and Thioethers. Blue Dyes for Synthetic Polymer Fibers.

Peters

1990

ChemInform

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267ChemInform Abstract Mono-and dibrominated 4,8-diamino-1,5-dihydroxyanthraquinones or 4,5-diamino-1,8-dihydroxyanthraquinones react with nucleophiles such as phenols (VII) or thiophenols (II) to give ethers or thioethers as outlined in the reaction scheme (32 examples given in the original paper). While the introduction of a thioether group results in a bathochromic shift, the phenoxy group causes a hypsochromic shift. On polyester material, the S-ethers give greenish-blue dyeings, while the O-ethers give reddish-blue ones. The fastness to light or sublimation is determined.

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1,5‐Dihydroxy‐4,8‐diamino‐ and 1,8‐dihydroxy‐4,5‐diaminoanthraquinone‐β‐ethers and thioethers. Blue dyes for synthetic polymer fibres

Cited by 4 publications

References 11 publications

Polymers and Dyes: Developments and Applications

Polymers and Dyes: Developments and Applications

Click‐coupling of anthraquinone dyes with β‐cyclodextrin: formation of polymeric superstructures

ChemInform Abstract: 1,5‐Dihydroxy‐4,8‐diamino‐ and 1,8‐Dihydroxy‐4,5‐diaminoanthraquinone β‐Ethers and Thioethers. Blue Dyes for Synthetic Polymer Fibers.

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