ODB-2 dye impurity and preparation method thereof

A technology of ODB-2 and dyes, which is applied in the field of preparation of ODB-2 impurities of fluoran-based thermal pressure-sensitive dyes, can solve the problems of undisclosed and other issues, and achieve the effects of easy-to-obtain raw materials, high yield, and high purity

Inactive Publication Date: 2020-07-24
UNIV OF JINAN
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Problems solved by technology

[0007] ODB-2 dye impurity is extremely important for dye quality research. The inventor accidentally discovered this impurity during production and found that it widely exists in heat and pressure sensitive dyes that use 2-methyl-4-methoxydiphenylamine as raw materials In the prior art, there is no document disclosing this impurity

Method used

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  • ODB-2 dye impurity and preparation method thereof
  • ODB-2 dye impurity and preparation method thereof
  • ODB-2 dye impurity and preparation method thereof

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preparation example Construction

[0022] The specific examples of the preparation method provided by the present invention are as follows to further describe the technical solution of the present invention, but the protection scope of the present invention is not limited to these examples. All changes or equivalent substitutions that do not depart from the concept of the present invention are included within the protection scope of the present invention.

[0023] The structural formula of the new ODB-2 dye impurity of the present invention is following formula I:

[0024]

[0025] The synthetic method of new ODB-2 dye impurity in the present embodiment is as follows:

Embodiment 1

[0027] Put 50 g of 100% concentrated sulfuric acid into a 100 ml three-necked flask at room temperature, start stirring, add 10 g of 2-methyl-4-methoxydiphenylamine solid to it in small amounts, slowly raise the temperature to 50 ° C, and all the solids are dissolved. The process of the reaction was controlled in the middle. After 0.5 h of reaction, the raw material point disappeared, and the reaction solution was slowly dropped into 500 ml of distilled water, all dissolved, and 13.5 g of solid precipitated after cooling, which was the target product ODB-2 dye impurity, with a yield of 98.47% and a purity of 99.41%. Perform mass spectrometry analysis on the generated impurities, as shown in the attached figure 2 ; HPLC analysis of purity, as attached image 3 .

Embodiment 2

[0029] Under the same environment as in Example 1, take a 100 ml three-necked bottle, add 30 g of 100% concentrated sulfuric acid thereinto, start stirring, and add 10 g of 2-methyl-4-methoxydiphenylamine solid to it in small amounts for several times, slowly Raise the temperature to 50°C, all the solids are dissolved, and the reaction process is controlled centrally. After 0.5 h of reaction, most of the raw materials remain, continue to heat up to 80°C, and react again for 0.5 h, and about 20% of the raw materials remain. Drop it into 500 ml of distilled water to form White flocculent insoluble matter, the reaction solution was taken for high-performance liquid chromatography analysis, the purity was 79.37%.

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Abstract

The invention relates to a novel fluorane thermal pressure sensitive dye 2-phenylamino-3-methyl-6-dibutylaminofluorane (ODB-2) impurity and a preparation method thereof. The impurity is named as 2-methoxy-4-methyl-5-phenylamino-benzenesulfonic acid, and the structural formula of the impurity is shown in the specification. Belongs to the field of organic dyes, the content of the impurity in the synthesis of the ODB-2 dye is high, the impurity has obvious influence on the quality of a finished product, the impurity refining effect is poor in the refining process, and the ODB-2 dye impurity is easily caused to exceed the standard, so that the research on the production way of the impurity and the directional synthesis of the impurity have important significance on the quality control of the ODB-2; the synthetic method of the ODB-2 impurity provided by the invention has the advantages of short reaction steps, easily available raw materials, the high yield and high purity.

Description

technical field [0001] The invention belongs to the field of organic dyes, and in particular relates to a preparation method of ODB-2 impurity of fluorane-type heat and pressure sensitive dyes. Background technique [0002] ODB-2 is currently the most widely used thermal dye for thermal and pressure-sensitive recording paper in the world. Its chemical name is 2-anilino-3-methyl-6-dibutylaminofluorane, and its structural formula is as follows: Formula III. In 1969, it was developed by the NCR company of the United States. In recent years, the demand has continued to increase. The annual demand in the world has reached 10,000 tons. Inexpensive, widely used in thermal and pressure-sensitive recording paper such as labels and faxes, and high-speed fax paper, etc. In addition, it can also be used as a thermochromic dye temperature-indicating material for electrical equipment, mechanical equipment, vehicles, and heating equipment. [0003] [0004] ODB-2 can be made of 2-methy...

Claims

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Application Information

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IPC IPC(8): C07C309/49C07C303/06
CPCC07C309/49C07C303/06
Inventor 李敏郑庚修武海潮高令峰郑广兵崔中倩
Owner UNIV OF JINAN
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