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Anthrapyridone compound and salt thereof, magenta ink composition containing such anthrapyridone compound, and colored body

An anthrapyridone and compound technology, applied in the field of magenta ink composition, can solve the problems of light fastness, gas resistance, poor sharpness, poor light fastness, etc., and achieve good fastness, good filterability, good storage stability sexual effect

Inactive Publication Date: 2008-07-16
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although xanthene pigments are excellent in hue and vividness, they are very poor in light fastness
In addition, the azo pigments using H acid have good evaluations in terms of hue and water resistance, but are inferior in light resistance, gas resistance, and clarity.
In this category, although magenta dyes with excellent vividness and light fastness are also being researched, they are still poor in light fastness compared to dyes of other hues such as cyanine dyes represented by copper phthalocyanines or yellow dyes.
[0007] Magenta pigments with excellent vividness and lightfastness have anthrapyridone-based pigments as their pigment skeletons (for example, refer to Patent Documents 1 to 8), but they can satisfy hue, vividness, lightfastness, water resistance, gas resistance, and solution stability. sexual all conditions hitherto undiscovered

Method used

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  • Anthrapyridone compound and salt thereof, magenta ink composition containing such anthrapyridone compound, and colored body
  • Anthrapyridone compound and salt thereof, magenta ink composition containing such anthrapyridone compound, and colored body
  • Anthrapyridone compound and salt thereof, magenta ink composition containing such anthrapyridone compound, and colored body

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156] (1) To 375.0 parts of N,N-dimethylformamide, while stirring, add the compound (R 1 =H) 381.0 parts, the compound (R 2 =4-phenyl)(4-hydroxybiphenyl) 44.6 parts, and 19.0 parts of pulverized (100 mesh) potassium carbonate, and raised temperature, reacted at 130 to 140° C. for 3 hours. The obtained reaction solution was cooled with water, 450 parts of methanol was added thereto, and after stirring for 30 minutes, the reaction product was filtered, separated, washed successively with 700 parts of methanol and 300 parts of warm water at about 80°C, and dried to obtain 65.9 parts of the above The compound of formula (12) (R 1 = H, R 2 =4-phenyl) as yellow-brown crystals.

[0157] (2) To 120 parts of xylene, while stirring, add 65.8 parts of the compound (R 1 = H, R 2 =4-phenyl), 1.4 parts of potassium carbonate, 67.2 parts of ethyl benzoylacetate (compound of formula (13), R 3 =H), and raise the temperature. The reaction was carried out at a temperature of 142 to 144° ...

Embodiment 2

[0175](1) The reaction solution containing the compound represented by the formula (17) was obtained by performing the operations of (1) to (5) in Example 1. Add an aqueous solution consisting of 3.2 parts of anthranilic acid, 3.7 parts of 25% caustic soda aqueous solution and 15 parts of water to the reaction solution, and add 25% caustic soda dropwise at a temperature of 27 to 30°C. Aqueous solution, while keeping the pH at 4.8 to 5.2, carry out the secondary condensation reaction for 30 minutes to obtain the reaction solution containing the compound represented by formula (19).

[0176]

[0177] (2) Add an appropriate amount of 25% caustic soda aqueous solution to the reaction liquid containing the compound of formula (19) obtained in the operation of the above (1), while maintaining the pH at 10.8 to 11.2, and at a temperature of 90 to 95° C. The reaction was carried out for 2 hours. After the reaction, water was added to the reaction liquid to adjust the liquid volume...

Embodiment 3

[0182] (1) The reaction solution containing the compound represented by the formula (17) was obtained by performing the operations of (1) to (5) in Example 1. To this reaction solution, add an aqueous solution consisting of 4.4 parts of 5-aminoisophthalic acid, 7.7 parts of 25% caustic soda aqueous solution and 15 parts of water, and drop 25% of Aqueous caustic soda solution, while maintaining the pH at 5.8 to 6.2, carried out the secondary condensation reaction for 30 minutes to obtain a reaction solution containing the compound shown in the following formula (20).

[0183]

[0184] (2) Add an appropriate amount of 25% caustic soda aqueous solution to the reaction liquid containing the compound of formula (20) obtained in the operation of the above (1), while maintaining the pH at 10.8 to 11.2, and at a temperature of 90 to 95° C. React for 2 hours. After the reaction, water was added to the reaction liquid to adjust the liquid volume to 250 parts, and the insoluble matte...

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Abstract

The present invention relates to a novel anthrapyridone compound in free acid form represented by the following formula (1), an ink composition containing the compound, and a colored body using the composition (in the above formula (1), R1 represents a hydrogen atom, Alkyl, etc., R2 represents a hydrogen atom, alkyl, phenyl, phenoxy, etc., R3 represents a hydrogen atom or methoxy group, X represents an anilino group that may have a substituent such as a sulfonic acid group, naphthalene that may be substituted by a sulfonic acid group Amino group, mono- or dialkylamino group which may have substituents such as sulfonic acid group, aralkylamino group, cycloalkylamine group, phenoxy group which may have substituents such as sulfonic acid group, hydroxyl group, amino group, etc. , Y represents a chlorine atom, a hydroxyl group, an amino group, etc.), the image recorded by the inkjet recording ink containing the compound of the present invention has high definition, and exhibits excellent light resistance and ozone resistance.

Description

technical field [0001] The present invention relates to a novel anthrapyridone compound, a magenta ink composition containing the anthrapyridone compound, and a colored body obtained by using the composition. Background technique [0002] Among the various color recording methods, the recording method of inkjet printing, which is one of the representative methods, although various inkjet methods of ink are being studied, but ink droplets are produced and then attached to various recording methods. recording on a material (such as paper, film, cloth, etc.). Since this method does not contact the recording head with the recording material, there is almost no sound and it is very quiet, and it has the advantages of easy miniaturization, high speed, and colorization. big development. [0003] In the past, inks such as fountain pens and felt pens and inks for inkjet recording have used water-based inks obtained by dissolving water-soluble dyes in water-based solvents. In these ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B5/14B41J2/01B41M5/00C07D401/12C09D11/00
CPCC07D401/12C09B5/14C09B67/0083C09D11/32C09D11/328Y10T428/24802B41J2/01B41M5/00
Inventor 松本弘之梶浦典子
Owner NIPPON KAYAKU CO LTD
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