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Carbonyl propyl sulfuryl anthracene pyridone sulfonic acid compound, preparation method and application thereof

A compound, sulfonic acid technology, applied in the direction of benzo-azabenzoxanthrone dyes, applications, household appliances, etc., can solve the problem that dyes have not yet met the color tone, vividness, light resistance, water resistance, ozone resistance and dissolution. problems such as stability and solution stability, insufficient dye solubility stability, insufficient long-term stability, etc., to achieve the effects of high long-term stability, image light fastness, and cost reduction

Active Publication Date: 2013-11-20
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] However, the dyes disclosed in these patents have not yet met all the requirements for hue, vividness, light fastness, water fastness, ozone fastness, solubility and solution stability.
Although some of these dyes have improved light fastness and ozone fastness, the solubility of the dyes and their stability in inkjet inks are not enough, especially the long-term stability is not enough
The long-term stability of the dye in the ink is related to the solubility of the dye, especially the solubility of the dye in water, which is not ideal in many cases

Method used

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  • Carbonyl propyl sulfuryl anthracene pyridone sulfonic acid compound, preparation method and application thereof
  • Carbonyl propyl sulfuryl anthracene pyridone sulfonic acid compound, preparation method and application thereof
  • Carbonyl propyl sulfuryl anthracene pyridone sulfonic acid compound, preparation method and application thereof

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preparation example Construction

[0145] The preparation of the ink composition of the present invention is: the dye compound represented by the general formula (I) or (III) or its salt or their mixture is dissolved in water or the above-mentioned aqueous solvent (water containing a water-soluble organic solvent) Or in a water-miscible organic solvent, it can be prepared by dissolving it together with the above-mentioned ink control agent and the like as needed.

[0146] In the above production method, there is no particular limitation on the order in which the components are dissolved. The dye may be dissolved in water or the above-mentioned aqueous solvent (water containing a water-soluble organic solvent), and the ink control agent may be added to dissolve the dye, or an aqueous solvent or an ink preparation agent may be added after dissolving the dye in water. The order may be different from this. Furthermore, an ink composition can be produced by adding an aqueous solvent and an ink preparation agent to ...

Embodiment 1

[0158] (1) In 350 parts of o-dichlorobenzene, add 100 parts of dimethyl sulfoxide, and add 160 parts of (C.I. Reactive Blue 19) derivative (sodium salt, formula V'-RB19), 10 parts in sequence while stirring Parts of sodium carbonate, 250 parts of ethyl benzoyl acetate and heating. Carried out the reaction at 175 to 180°C for 4 hours, during which the by-product ethanol and water generated in the reaction were discharged from the reaction system by azeotropic distillation, and the color gradually changed from blue to purple, and the liquid chromatograph detected that the reaction was complete (about 4 Hour). Cooling, at M -H] -1 ). The most abundant and accurate molecular mass of the intermediate dye product V-RB19 (in the form of free sulfonic acid) M for 804.1.

[0159]

[0160] (2) In 450.0 parts of 95.0% sulfuric acid, under cooling and stirring, add 380.0 parts of 50% oleum to prepare 830 parts of 10% oleum. After cooling, at a temperature not higher than 40°C, add...

Embodiment 2

[0171] The sodium salt of intermediate V-RB19 was prepared in the same manner as in step 1 of Example 1. Then 10% SO in the 2nd step sulfonation 3 h 2 SO 4 Replaced with 12% SO 3 h 2 SO 4 , Reaction temperature is brought up to 85-90 ℃, by the same method of embodiment 1 step 2, desalination obtains 2600 parts of solutions containing 185 parts of mixed dyes (M2, sodium salt form), and the maximum absorption wavelength in water is 533nm.

[0172] Adopt reverse-phase ion-pair liquid chromatography, according to the same separation device and method as in Example 1, the dye compound in the above-mentioned dye mixture M2 is separated, and what is washed out at first is the Dm6 pure compound of six charges; Then The five-charged Dm2 pure compound and Dm4 pure compound are washed out in sequence; then the four-charged dye Dm8 pure compound and Dm10 pure compound are sequentially washed out.

[0173] In the high-performance liquid chromatography HPLC analysis, according to the ...

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Abstract

The present invention relates to compounds shown in the general formula (I) or (III), the salts thereof or their mixtures, as well as their preparation method and application. In the general formula (I), X1 is H or CO2H; X2 is OH or phenyl group with 0-2 sulfonic acid substituents, and the sulfonic acid substituents are located at random positions of a benzene ring; when X2 is OH, X1 is H; when X2 is phenyl group with 0-2 sulfonic acid substituents, X1 is H or CO2H; n is an integer of 0-2; and in the general formula (III), n and m are respectively an integer of 0-2. The compounds and the mixtures not only have improved light resistance, ozone resistance and water resistance, but also have excellent water solubility and long-term stability in ink-jet ink.

Description

technical field [0001] The present invention relates to a novel anthrapyridone sulfonic acid compound and its preparation method and application. In particular, it relates to an anthrapyridone sulfonic acid compound having a carbonyl sulfone group, a salt thereof, or a mixture thereof, and use thereof as a magenta colorant. Background technique [0002] Among various color recording methods, the inkjet printing method is one of typical methods thereof. So far, a variety of ink ejection methods have been researched and developed to form small droplets of ink, which are adsorbed on various recording materials (such as paper, film, fabric, etc.) to achieve recording. Because the nozzle of inkjet printing is not in contact with the recording material, it is silent and quiet, and it is easy to achieve miniaturization, high speed, and colorization. As a result, it has developed rapidly in recent years. [0003] The traditional ink is prepared in this way: the water-soluble dye ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B5/14C09D11/02C09D7/12
CPCC09B67/0038C09D11/328C09D5/00C09D5/028C09D7/007C09B5/14C07D221/18C09D11/00C09B67/0034C09D7/41
Inventor 彭孝军吴金河龙志张蓉王力成王风李少磊樊江莉宋锋玲孙世国
Owner DALIAN UNIV OF TECH
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