- Brilliant blue disperse dye and application thereof
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The invention discloses a brilliant blue disperse dye which is synthesized by anthraquinone acid dye and comprises more than one component shown as a structural formula (I), and in the formula, R1, R2 and R3 are -H,-CH3,-NHCOCH3 and -SO2CH2CH2OH. The brilliant blue disperse dye is energy-saving, emission-reducing, high in productivity and simple in synthesis process, while other anthraquinone brilliant blue disperse dyes such as 60 blue and 56 blue disperse dyes are complex in process, low in yield and much in wastewater.
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Paragraph 0031-0034
(2021/09/08)
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- Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes
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Novel 1-amino-4-(ar)alkylaminoanthraquinone derivatives bearing different substituents (Br, CH2OH, CN, or CH3) at the 2-position of the anthraquinone scaffold were synthesized by copper-catalyzed Ullmann condensation. The 2-substituted 1-amino-4-bromoanthraquinone derivatives (bromaminic acid analogues) were reacted with a variety of alkyl-, aryl-, and aralkylamines. Different reaction conditions were applied depending on the physical state of the amine and the nature of the substituent at the 2-position of the anthraquinone scaffold. A solvent-free synthetic procedure was developed for reactions with liquid amines. Condensation with solid amines required the addition of a solvent, and reaction conditions had to be optimized for each of the anthraquinone derivatives. Our results emphasize that copper-catalyzed reactions are highly variable depending on the molecules and anions present in the medium, since different reaction mechanisms apply. The synthesized anthraquinone derivatives may be useful as new dyes, or may show biological activity and could be employed as tool compounds in experimental pharmacology.
- Malik, Enas M.,Rashed, Mahmoud,Wingen, Lukas,Baqi, Younis,Müller, Christa E.
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- 35. Ueber die Dicyanierung der 1,4-Diaminoanthrachinone und die Reactivitaet der 1,4-Diamino-9,10-dioxo-9,10-dihydroanthracen-2,3-dicarbonitrile gegenueber nucleophilen Reagenzien
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The reaction of 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2-sulfonic acid (1, R=C6H5) with cyanide in water yields a mixture of 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2-carbonitrile (3, R=C6H5) and 1-amino-4-(phenylamino)anthraquinone (4, R=C6H5) under the usual reaction conditions (Scheme 1).In dimethylsulfoxide, however, a second cyano group is introduced, and 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2,3-dicarbonitrile (7) is formed (Scheme 2).The cyano groups are very reactive towards nucleophiles.The cyano group in 2-position can be substituted by hydroxide and aliphatic amines (Schemes 5 and 6).The cyano group in 3-position can be eliminated by aliphatic amines and hydrazine (Scheme 7).Nucleophilic attack at the cyano C-atom of the 2-cyano group by suitable reagents leads to ring formation, yielding e.g. 2-(Δ2-1,3-oxazolin-2-yl)-, 2-(benzimidazol-2-yl)- and 2-(1H-tetrazol-5-yl)anthraquinones (Schemes 8 and 10).
- Adam, Jean-Marie,Winkler, Tammo
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p. 411 - 421
(2007/10/02)
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