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Preparation of 1-amino-4-hydroxy anthraquino

A technology of hydroxyanthraquinone and amino, which is applied in the field of preparing 1-amino-4-hydroxyanthraquinone, can solve the problems of low space-time yield and dye not very bright, and achieve improved product quality and excellent space-time yield. The effect of high efficiency and excellent thermal stability

Inactive Publication Date: 2003-04-02
BAYER AG
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For all methods, the usual drawbacks are low space-time yields and the resulting dyes are not very bright

Method used

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  • Preparation of 1-amino-4-hydroxy anthraquino

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0046] Embodiment 11-p-toluidino-4-hydroxyl anthraquinone:

[0047] In a 1000ml four-necked bottle, in 413 parts of N-methylpyrrolidone, add 271 parts (1.13mol) of quinizarin, 17 parts (0.07mol) of dihydroquinizarin, 157 parts (1.47mol) under vigorous stirring p-Phenylenediamine, 4 parts (0.065 mol) of boric acid, 4.5 parts of water and 35.5 parts (0.355 mol) of 90% lactic acid. The mixture was heated to 90°C and maintained at this temperature for 12 hours, then cooled and filtered. The resulting product was washed with 500 parts of hot methanol at 60°C and dried. 370 parts (94% yield) of a dark purple product were obtained which, when used to dye polystyrene, give a very bright purple color.

Embodiment 2

[0048] Example 21-anilino-4-hydroxyanthraquinone:

[0049] Example 1 was repeated except that 157 parts of p-toluidine were replaced by 136 parts (1.46 mol) of aniline. 312 parts (83% yield) of a dark purple product were obtained which, when used to dye polystyrene, provided a purple shade of similar color strength to the dye described in Example 1, but significantly redder Some.

Embodiment 31

[0050] Example 31-P-acetamidoanilino-4-hydroxyanthraquinone:

[0051] Example 1 was repeated again, except that 220 parts (1.47 mol) of p-amino-acetanilide was used instead of 157 parts of p-toluidine, and 600 parts of NMP was used instead of 400 parts. 312 parts of a deep purple product were obtained which when used to dye polystyrene give a very bright purple. This shade has similar color strength to the dye described in Example 1, but is slightly bluer.

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Abstract

The present invention relates to a process for preparing 1-amino-4-hydroxyanthraquinones of the formula (I) wherein R is an aliphatic or aromatic radical, by reacting 1,4-dihydroxyanthraquinone, with aliphatic or aromatic amines in the presence of N-methyl-2-pyrrolidone.

Description

technical field [0001] The present invention relates to a method for preparing 1-amino-4-hydroxyanthraquinone and the use of the compound prepared by the method in plastic body dyeing. Background technique [0002] 1-Amino-4-hydroxyanthraquinone is known, for example, as a dye for plastics and synthetic fibers and as an intermediate for the preparation of wool dyes. These compounds have hitherto been obtained by reacting 1,4-dihydroxyanthraquinone (quinizarin), optionally with 2,3-dihydro-1,4-dihydroxyanthraquinone, in the presence or absence of condensation assistants (Leucoquinone) mixed and reacted with amines in the system. [0003] In US-A-1931264, for example, the formation of bis-adducts can be suppressed by using aqueous solvents, but at the same time an excess of amine needs to be used in order to obtain good yields. In GB-A-2013701, the reaction is carried out in the presence of a surfactant. DE-A-1619646 and US-A-2419405 describe the use of alcohols as solvents...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07C221/00C07C225/36C07C231/12C07C233/43C09B1/514
CPCC07C2103/24C07C231/12C07C221/00C09B1/5145C07C2603/24C07C225/36C07C233/43
Inventor C·蒂贝斯J·-W·施塔维茨
Owner BAYER AG
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