Azo pigments, coloring compositions, coloring method and colored articles

A technology for coloring compositions and azo pigments, applied in the directions of azo dyes, monoazo dyes, dyeing methods, etc., can solve the problems of insufficient heat resistance, insufficient heat resistance or solvent resistance, etc.

Active Publication Date: 2011-09-14
DAINICHISEIKA COLOR & CHEM MFG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As a method to solve these problems, as a black pigment with infrared reflectivity, there is a conventionally known color index (C.I.) coupling component 25 (2-hydroxy-11H-benzo[a]carbazole-3-carboxy- (2'-methyl)-p-methoxyaniline) or C.I. coupling component 13 (2-hydroxy-11H-benzo[a]carbazole-3-car

Method used

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  • Azo pigments, coloring compositions, coloring method and colored articles
  • Azo pigments, coloring compositions, coloring method and colored articles
  • Azo pigments, coloring compositions, coloring method and colored articles

Examples

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Embodiment

[0048] Hereinafter, synthesis examples, examples, and comparative examples are given to further specifically explain the present invention. Among them, "parts" or "%" in the text are quality standards unless otherwise specified.

Synthetic example 1

[0050] (a) Synthesis of coupling component "coupling agent K"

[0051] Add 2,000ml of chlorobenzene, 170.5g (0.57 mol) of sodium 2-hydroxy-11H-benzo[a]carbazole-3-carboxylate and 5-aminobenzimidazolone at 80~85℃ for 1 hour Add 52.4g (0.38mol) of phosphorus trichloride to 56.7g (0.38mol) of the mixture, and then stir at the same temperature for 2 hours, and then at 128-130°C for 25 hours, and then adjust it to alkaline state The solvent was removed by steam distillation, filtered and dried at 50-60°C to obtain the crude 2-hydroxy-11H-benzo[a]carbazole-3-carboxy-N-benzimidazolone-5-amide Things. The crude product was dissolved in 3,000 ml of methanol in which 23 g of sodium hydroxide was dissolved, and after filtering the insoluble components, 68 g of acetic acid was added to precipitate (2 times). The precipitate was filtered, washed with methanol, washed with water, and dried to obtain a coupling agent (hereinafter referred to as "coupling agent K") (melting point: 449°C).

[00...

Synthetic example 2

[0060] 2.23 g (0.01 mol) of 1-aminoanthraquinone as an aromatic amine was suspended in 11.3 g of glacial acetic acid, and 3.7 g of concentrated hydrochloric acid was added thereto and stirred. 2.6 g of water was added thereto, maintained at a temperature of 0 to 5°C, 2.0 g of a 40% sodium nitrite aqueous solution was added, and stirred at the same temperature for about 30 minutes to obtain a yellow diazonium salt solution. 4.8 g of sodium acetate trihydrate was added thereto to prepare a diazonium salt solution. Coupling with 4.08 g (0.01 mol) of coupling agent K was carried out in the same manner as in Synthesis Example 1(b) to synthesize a black azo pigment of the following formula. Hereinafter, it is referred to as "black pigment-2".

[0061]

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Abstract

Dark-color azo pigments characterized by being represented by general formula (I). The azo pigments have properties of reflecting or transmitting infrared rays or solar heat rays as optical characteristics and exhibit excellent fastness, particularly excellent heat resistance, as pigment characteristics.

Description

Technical field [0001] The present invention relates to a novel dark to black (hereinafter referred to as dark color system) azo pigment, a coloring composition, a coloring method, and a colored article. In more detail, it relates to a novel dark-colored azo pigment obtained as follows, a coloring composition containing the dark-colored azo pigment, a coloring method using them, and a colored article obtained by using the novel dark-colored azo pigment The specific coupling component is 2-hydroxy-11H-benzo[a]carbazole-3-carboxy-N-benzimidazolone-5-amide as the coupling component, and a known diazo compound is used as the diazo component, and Obtained by the coupling reaction of the two. Background technique [0002] Conventionally, carbon black has been generally used as a black-based pigment, and iron oxide black (ferric oxide), black composite oxide pigments, and the like have also been used. Since these pigments exhibit black color and absorb light of wavelengths from the vi...

Claims

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Application Information

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IPC IPC(8): C09B29/22B05D5/06C08K5/3447C08L101/00C09B67/20C09B67/46C09D11/02D06P1/04C08K5/23C09B29/20C09B67/02C09B67/08C09B67/22C09D7/12C09D11/037C09D17/00C09D201/00D06P5/00
CPCD06P1/04C09B29/20C09D11/037C09B29/22B05D5/06C08K5/3447C08L101/00
Inventor 西胜宏明冈本久男浅川久纪富田研二郎中村道卫
Owner DAINICHISEIKA COLOR & CHEM MFG CO LTD
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