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Preparation method of fluorane dye for thermal-sensitive printing

A fluorane dye, thermal printing technology, applied in the field of thermal dyes, to achieve the effect of high conversion rate, convenient for large-scale industrial production, and strong color rendering ability

Inactive Publication Date: 2017-07-21
沈阳感光化工研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Introducing different substituent groups on the amino group of fluorane can obtain fluorane with different colors and properties, but so far, there are not many domestic researches, and foreign countries are only in the development stage. The introduction of heterocyclic rings into fluorane There are fewer reports, which may be the potential focus and hotspot of fluorane research in the future

Method used

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  • Preparation method of fluorane dye for thermal-sensitive printing
  • Preparation method of fluorane dye for thermal-sensitive printing
  • Preparation method of fluorane dye for thermal-sensitive printing

Examples

Experimental program
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Embodiment 1

[0027] In this embodiment, the preparation method of fluoran dyes for thermal printing, the specific steps are as follows:

[0028] 1, the synthesis of intermediate A, its reaction formula is as follows:

[0029]

[0030] Add 50g (0.15mol) fluorescein (C 20 h 12 o 5 ), 1.46g (0.02mol) dimethylformamide (DMF) and 200ml sulfolane (C 4 h 8 o 2 S), was added to a 500ml reactor, stirred and heated to 60°C, and 70.8g (0.60mol) of thionyl chloride (SOCl 2 ), the dropwise addition is completed in about 30 minutes, continue to heat up to 80°C, keep warm for 2 hours, and the reaction is completed, cool it to about 30°C, then pour it into 250ml of acetone and water mixture with a volume ratio of 1:1, stir and precipitate After 2 hours of filtration, the filter cake was rinsed with 50ml of acetone and water mixed solution with a volume ratio of 1:1, and dried to obtain 50g of light yellow intermediate A with a yield of 90.5wt% and a content of about 96.5wt%.

[0031] The spectru...

Embodiment 2

[0047] The difference from Example 1 is that in this example, the preparation method of fluoran dyes for thermal printing, the specific steps are as follows:

[0048] (1) In the reaction bottle, add 50g (0.15mol) fluorescein (C 20 h 12 o 5 ), 2.09g (0.03mol) DMF and 300ml sulfolane (C 4 h 8 o 2 S), stirring and heating to 60 ° C, dropwise added 106.2g (0.90mol) thionyl chloride (SOCl 2 ), the dropwise addition is completed in about 30 minutes, continue to heat up to 100°C, keep the temperature for 4 hours, and the reaction is completed, cool it to about 30°C, then pour it into 250ml of acetone and water mixture with a volume ratio of 1:1, stir and precipitate After 3 hours of filtration, the filter cake was rinsed with 70ml of acetone and water mixed solution with a volume ratio of 1:1, and dried to obtain a light yellow solid, 48.1g of 3,6-dichlorofluorane, with a yield of 86.90wt%. The content is about 98.4wt%.

[0049] (2) In the reactor, add 100ml DMF, 36.9g (0.10mo...

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Abstract

The present invention relates to the field of thermal-sensitive dyes, particularly to a preparation method of a fluorane dye for thermal-sensitive printing. According to the preparation method, fluorescein is adopted as a starting raw material, and substitution and condensation are performed to obtain the final product 3'-[octyl(2-ethylphenyl)amino]-6'-(2-methylphenyl)amino-spiro[isobenzofuran-1(3H),9'-[9H]xanthene-3-one, wherein the fluorescein is fluorescein isothiocyanate, tetraethyl rhodamine or tetramethyl isothiocyanate rhodamine. According to the present invention, the method has advantages of simple operation, high conversion rate and low cost, and suitable for large-scale industrial production; the obtained fluorane dye has strong color rendering ability, can realistically, clearly and rapidly reduce the image; the fluorane dye is used in the new inkless printing technology, wherein the three coating materials such as yellow, magenta and cyan and including C are coated on the picture paper through dispersion coating in the new inkless printing technology, and the high quality image is obtained by heating the picture paper; and the built-in ink box is not required, such that the small size printer can be produced, and even the printer can be built in the digital camera or camera mobile phone.

Description

technical field [0001] The invention relates to the field of thermal dyes, in particular to a preparation method of fluoran dyes for thermal printing. Background technique [0002] Thermosensitive agent recording material is a new type of digital image recording material, which has many advantages such as fast recording speed, good imaging quality, simple supporting device, fast processing, no chemical treatment, and no environmental pollution. Thermosensitive dyes came out in 1950, and NCR Corporation of the United States developed the first thermosensitive recording paper, and thermosensitive dyes have developed rapidly in the past 50 years. With the revolutionization of office automation and information transmission, the variety and application range of thermosensitive dyes are constantly expanding. [0003] So far, countries around the world have developed more than 60 kinds of thermosensitive dyes, the main chemical structures of which are phthaloketones, phenothiazine...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07D493/10
CPCC09B57/00C07D493/10
Inventor 刘景宋昱李响洪百欣
Owner 沈阳感光化工研究院有限公司
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