Binuclear anthracene pyridone sulfonic acid compounds or salts thereof, and preparation method and application thereof

A technique for binuclear anthrapyridone sulfonic acid and compounds, which is applied in the field of structure of binuclear anthrapyridone sulfonic acid compounds, and can solve problems such as unsatisfactory solubility

Inactive Publication Date: 2012-06-27
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the other hand, the long-term stability of dyes in ink is related to the solubility of dyes, especially the solubility of dyes in water, and the solubility of dyes in the prior art is not ideal enough. Therefore, it is also urgent to find dye compounds with better solubility

Method used

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  • Binuclear anthracene pyridone sulfonic acid compounds or salts thereof, and preparation method and application thereof
  • Binuclear anthracene pyridone sulfonic acid compounds or salts thereof, and preparation method and application thereof
  • Binuclear anthracene pyridone sulfonic acid compounds or salts thereof, and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0067] The preparation method of the dinuclear anthrapyridone sulfonic acid compound of the general formula I, using the mononuclear compound III as the basic raw material, forms a ring in an organic solvent to form the compound IV of the general formula, and then sulfonates and hydrolyzes the compound of the general formula with an amino group The general formula V, then forms the intermediate VI with cyanuric chloride, then reacts with the compound RH to form the general formula VII, and finally connects with the linker H-L-H to form the general formula I. Salt is then converted into salt.

[0068] In the ring-forming reaction of formula III, the reaction condition of the reaction of blue anthraquinone sulfonic acid compound (general formula III) and benzoyl acetate to form compound IV is: 1. compound III and benzoyl acetate (such as formosyl acetate) ester, ethyl ester, propyl ester, isopropyl ester) in an organic solvent at a molar ratio of 1:2-5 at 175-180°C.

[0069] Th...

Embodiment 1

[0104] Example 1. Preparation of Compound E-1

[0105] (1) Add 60 parts of dimethyl sulfoxide to 210 parts of o-dichlorobenzene, and then add 142.2 parts of C.I. acid blue 324 (sodium salt), 3.6 parts of sodium carbonate, and 135.0 parts of ethyl benzoyl acetate under stirring and heat up. React at a temperature of 175 to 180°C for 6 hours. The ethanol and water generated in the reaction are evaporated out of the reaction system through azeotropic distillation, and the color gradually changes from blue to purple. The liquid chromatograph detects that the reaction is complete (it takes about 6 Hour). After cooling, add 300 parts of isopropanol at 30°C and stir for 30 minutes, filter and separate the solid, and wash the resulting filter cake with 400 parts of isopropanol, dry to obtain 155 parts of lavender crystal E1-1 sulfonic acid, sodium salt). Maximum absorption in water at 535 and 560nm, mass spectrum (EI-MS) m / z (-): 578.1 ([ M -H] -1 ). Intermediate dye E1-1 (with ...

Embodiment 2

[0115] Example 2. Preparation of compound E-2

[0116] Compound E1-C1 was prepared according to steps (1)-(3) in Example 1 2

[0117] (4) Containing the above-mentioned E1-C1 2 To the reaction solution, ice was added to adjust the temperature to 5°C. 25% sodium hydroxide aqueous solution was added dropwise to adjust the pH to 5-6. In addition, 13.4 parts of sodium p-hydroxybenzenesulfonate and 25% aqueous sodium hydroxide solution were added to 40 parts of water to adjust the pH to 9 to form an aqueous solution. The aqueous solution of sodium p-hydroxybenzenesulfonate was added dropwise to the above reaction solution at 5° C. over 30 minutes. Continuously add ice and aqueous sodium hydroxide solution, maintain the pH value at 9.0±0.3, raise the temperature to 27-30°C, react at this temperature and pH value for 1 hour, and then react at 40-45°C for 1 hour. After completion of the reaction, water was added to adjust the liquid volume to about 350 parts, and then the insolub...

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Abstract

The invention relates to a binuclear anthracene pyridone sulfonic acid compounds disclosed as general formula I or salts thereof, and a preparation method and application thereof. A fuchsin ink composition prepared from the compounds and salts thereof appears distinct color tone with high brightness when being applied on ink jet recording paper, and has excellent water solubility; and the ink composition has good filterability for the filter membrane in the manufacturing process. After being stored for a long time, the ink composition prepared by the compounds does not precipitate crystals, does not have physical changes, color changes or the like, and thus, has high storage stability. The printing object using the fuchsin ink composition can trustily display the color image tones of the photo without selecting the recorded material, and has the advantages of high light fastness, high ozone resistance, high moisture resistance and high image long-term storage stability.

Description

technical field [0001] The invention relates to the structure of a kind of dinuclear anthrapyridone sulfonic acid compound, the synthesis method of the dinuclear anthrapyridone sulfonic acid compound, and the magenta ink containing the dinuclear anthrapyridone sulfonic acid compound used for inkjet printing. Background technique [0002] The inkjet printing method is one of typical color recording methods. Since the nozzle does not come into contact with the recording material, it is quiet without sound, and it is easy to miniaturize, speed up, and colorize, so it has developed rapidly in recent years. [0003] In the prior art, inks for inkjet printing are usually prepared by dissolving water-soluble dyes in aqueous media and adding water-soluble organic solvents that can prevent ink clogging of pen tips and inkjet nozzles. These inks are required to have high-density printed images, no clogging of the pen tip or nozzle, good drying on the recorded material, less penetrati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09B5/14C09D11/02C09D11/328
Inventor 彭孝军吴金河樊江莉孟凡明宋锋玲孙世国张蓉王静月龙志王力成
Owner DALIAN UNIV OF TECH
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