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Anthrapyridone azo dyes, their preparation and use

An anthrapyridone azo, dye technology, applied in the direction of anthraquinone-azo dyes, azo dyes, anthracene dyes, etc.

Inactive Publication Date: 2018-08-31
DFI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Dyes of type (II) do not meet other required requirements such as good photostability and good resistance to ozone degradation

Method used

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  • Anthrapyridone azo dyes, their preparation and use
  • Anthrapyridone azo dyes, their preparation and use
  • Anthrapyridone azo dyes, their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0051]Prepared dyes of formula (III), where M is designated, are listed in Table 1 .

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] The prepared dyes of structural formula (III) are listed in Table 1 together with their maximum absorption positions in aqueous solution (buffer pH 7.0):

[0065] Table 1

[0066]

[0067]

[0068] The compound of formula (III) may exist in the form of the free acid or its inorganic salt.

[0069] Preferably, these compounds are present in the form of their alkali metal or ammonium salts, where the ammonium cation may be substituted.

[0070] Examples of such substituted ammonium cations are 2-hydroxyethylammonium, bis-(2-hydroxyethyl)ammonium, tris-(2-hydroxyethyl)ammonium, bis-(2-hydroxyethyl)-methylammonium hydroxy-ammonium, tris-[2-(methoxyethoxy)-ethyl-ammonium, 8-hydroxy-3,6-dioxoctyl ammonium and tetraalkylammonium such as tetra...

Embodiment 1

[0095] Example 1: The anthrapyridone dyes (10A) of Table 1, where R = H and M is Na, were prepared in the following manner:

[0096] The preparation of the brominated anthrapyridone compound of structural formula (X):

[0097] 75.5g (0.25Mol) 1-amino-4-bromoanthraquinone (available from Sigma-Aldrich GmbH, Buchs, Switzerland), 59.5g (0.3Mol) ethyl benzoyl acetate 97% (available from Sigma-Aldrich GmbH, Buchs, Switzerland), 3.9 g (0.04 Mol) of potassium acetate and 125 ml of 1,2-dichlorobenzene were stirred at a temperature of 140° C. for 22 hours in a nitrogen atmosphere. About 12 ml of ethanol was removed from the reaction mixture by distillation.

[0098] Subsequently, the resulting dispersion was cooled to room temperature, the product was sucked off, washed well with ethanol and dried.

[0099] 70.2 g of product of formula (X) are obtained in this way.

[0100]

[0101] Preparation of dyes of structural formula (XI):

[0102] 34.4 g (0.08 Mol) bromoanthrapyridone...

Embodiment 2

[0117] Example 2: Anthrapyridone azo dyes (10B) in Table 1 were prepared as in Example 1, wherein M is Na. However, in the preparation of (X), the 1-amino-4-bromoanthraquinone (CAS81-62-9) in Example 1 was replaced with 1-methylamino-4-bromoanthraquinone (CAS 128-93-8) .

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PUM

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Abstract

Azo anthrapyridone dye of general formula (III) wherein A, R1, R2, B, M and n are as described in the specification, are excellent magenta dyes for dyeing and printing of paper, other cellulose containing materials and textiles materials and, in particular, for the preparation of recording fluids for ink jet printing and for writing utensils.

Description

technical field [0001] The present invention relates to novel anthrapyridone azo dyes and their salts, their preparation and their use in dyeing and printing operations. The present invention also relates to liquid dye formulations containing at least one monoazo dye, in particular to aqueous recording fluids for inkjet printing and writing implements. Background technique [0002] Inkjet printing replaces or complements classical methods of image reproduction in many fields. Although inkjet printing is quite mature, further improvements are still needed, especially in the graphic and photographic fields. Modern inkjet printers need to provide optimum prints in these areas on recording papers such as polymer-based recording papers or fast-drying nanoporous recording papers. In these areas, the stability against light and oxidizing gases (ozone, nitrogen oxides) as well as against large color spaces (gamuts) of printed images is primitive. This can only be achieved by usin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B56/12C09B56/00C09D11/328D06P3/60C09B5/14
CPCC09B56/00C09D11/328D06P3/6008C09B67/0041C09B56/12C09B67/0046C09D11/36
Inventor 达米安·穆瓦尼奥库尔特·贝迪格
Owner DFI CHEM
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