Method for preparing black fluorane thermal-pressure sensitive dye by virtue of one-step method

A fluorane-based, thermal and pressure-sensitive technology, which is applied in the direction of azo dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of cumbersome production process, large discharge of waste acid and waste alkali, and long time consumption, so as to avoid Local temperature is too high, the amount of sulfuric acid is reduced, and the effect of reducing energy consumption

Active Publication Date: 2016-08-10
ZHEJIANG HONGSHENG CHEM IND +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The technical problem to be solved by the present invention is to provide a one-step method for preparing black fluoran thermal pressure-sensitive dyes. The method of the present invention can overcome the large amount of waste acid and waste alkali in the existing production process, and the production process is cumbersome and time-consuming. Defects

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  • Method for preparing black fluorane thermal-pressure sensitive dye by virtue of one-step method
  • Method for preparing black fluorane thermal-pressure sensitive dye by virtue of one-step method
  • Method for preparing black fluorane thermal-pressure sensitive dye by virtue of one-step method

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Embodiment 1

[0059] Embodiment 1, the method for preparing black fluoran class thermal pressure-sensitive dye by one-step method, carries out following steps successively:

[0060]1). Add 150mL of dichloromethane, 55.4g (0.15mol) of 2-carboxy-4'-dibutylamino-2'-hydroxybenzophenone and 2-methyl-4-methoxy into a 500mL four-neck flask 32g (0.15mol) of diphenylamine, and slowly add 40mL (about 73.5g) of 98% sulfuric acid dropwise under stirring conditions until all the materials are dissolved, and the temperature is kept below 35°C. After the dropwise addition, the temperature was raised to 40° C. for reflux reaction for 4.5 hours.

[0061] 2). Continue to stir after the reaction, slowly drop 150ml of water into the four-necked flask, and recover dichloromethane by exothermic, that is, control the temperature of the reaction solution at 65-70°C to distill and recover dichloromethane, and keep it warm for 30 minutes. Add 150mL of toluene, continue to heat up to 85-90°C and stir for 30 minutes,...

Embodiment 2

[0064] The dichloromethane in Example 1 was replaced with 1,1-dichloroethane, and the temperature was raised to 58° C. for reflux reaction for 3 hours. The rest was the same as in Example 1 to obtain 73.4 g of a white solid with a yield of 92%. As detected by HPLC, the content of the compound of formula IV in the product is >99.5%.

[0065] R in the benzophenone derivatives described in this example 1 , R 2 Both represent butyl. That is, the benzophenone derivative is 2-carboxy-4'-dibutylamino-2'-hydroxybenzophenone; the black fluoran-based heat pressure sensitive dye is 3-dibutylamino-6-methyl-7 -anilinofluorane.

Embodiment 3

[0067] The dichloromethane in Example 1 was replaced with chloroform, and the temperature was raised to 62° C. for reflux reaction for 2.5 hours. The rest was the same as in Example 1 to obtain 71.8 g of white solid with a yield of 90%. Checked by HPLC, the content of the compound of formula IV in the product is >99.5%.

[0068] R in the benzophenone derivatives described in this example 1 , R 2 Both represent butyl. That is, the benzophenone derivative is 2-carboxy-4'-dibutylamino-2'-hydroxybenzophenone; the black fluoran-based heat pressure sensitive dye is 3-dibutylamino-6-methyl-7 -anilinofluorane.

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Abstract

The invention discloses a method for preparing a black fluorane thermal-pressure sensitive dye by virtue of a one-step method. The method comprises the following steps: (1) acid-catalysis cyclic condensation: adding a diphenyl ketone derivative and 2-methyl-4-methoxydiphenylamine into an organic solvent I with a relatively low boiling point, adding a sulfuric acid solution while stirring, and heating to a reflux temperature to react for 1.5-4.5 hours; and (2) post-processing refining: adding water into reaction liquid obtained in the step (1), recycling the organic solvent I with the relatively low boiling point by virtue of heat release, then adding a nonpolar solvent II into the recycled reaction liquid, carrying out heating reflux to separate a water phase so as to obtain an organic phase, carrying out cooling, crystallization, filtering and solvent washing on the organic phase, and drying, so as to obtain the black fluorane thermal-pressure sensitive dye.

Description

technical field [0001] The invention relates to a method for preparing an organic dye, in particular to a method for preparing a black fluoran thermosensitive dye. Background technique [0002] The black fluoran-based thermal pressure-sensitive dye is a compound with a xanthene type as the parent structure, and its structural formula is shown in formula IV. It is usually a colorless or light-colored crystal. When it contacts with a color developer (acid clay, bisphenol A, POB, etc.), it develops color with the cracking of the lactone ring inside the molecule. Because of its high sensitivity, high color density and good stability, different colors can be displayed by introducing different substituents on the fluorane matrix, and it is widely used in the manufacture of thermal recording paper. Black is currently one of the most important thermal pressure sensitive dyes. Variety. [0003] [0004] Formula S-1, R 1 , R 2 Represent different substituents, such as methyl, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C07D493/10
CPCY02P20/582C09B57/00C07D493/10
Inventor 孔明贡晗刘玉枫陶建国彭文博万德贵
Owner ZHEJIANG HONGSHENG CHEM IND
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