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Method for preparing 3-dibutylamino-6-methyl-7-anilinfluorane

A technology of anilinofluoran and dibutylamino, which is applied in the field of preparation of heat-sensitive dyes, can solve the problems of many wastes, unstable quality, low yield and the like

Inactive Publication Date: 2011-07-06
李俊辉
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the disadvantages of low product yield, many wastes, high impurities, unstable quality, high cost of ethylene glycol solvent, and difficult process control, etc., and through actual verification, it cannot form a large-scale factory production
The small test products produced also failed to pass the customer's use verification
[0006] At present, the existing process technology of the thermal dye ODB2 is directly scaled up and produced only based on the small-scale test technology in the laboratory, so its product quality cannot meet the existing international strict requirements for it, and cannot compete in the international market. For example, in the product Appearance, content, impurity requirements, etc. are quite different from international standards
Moreover, the process is cumbersome and unstable, such as complicated refining procedures, difficult removal of by-products, poor product quality, low yield, high price, coloring matter pollutes equipment and the environment, needs to be cleaned, and resinous matter is not suitable for removal

Method used

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  • Method for preparing 3-dibutylamino-6-methyl-7-anilinfluorane
  • Method for preparing 3-dibutylamino-6-methyl-7-anilinfluorane
  • Method for preparing 3-dibutylamino-6-methyl-7-anilinfluorane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Add 760g of 98% concentrated sulfuric acid to a 1000mL three-neck flask, slowly add 208.2g of BBA to the flask under stirring, and finish adding in 1.5 hours. After the BBA is completely dissolved, slowly add 62.5g of DPA, and finish adding in 2 hours The process temperature is kept between 15-20°C and kept warm for 4-5 hours. Then the reactant was slowly added dropwise to a large amount of ice-water mixture to solidify for 1.5 hours, stirred for another 3-4 hours, and suction filtered to obtain the solidified substance.

[0014] Get solidification 200g and join in the 500mL three-necked flask, slowly add dropwise the lye formed by the NaOH of 50 grams of water and 30g, and add toluene 150g, stir, heat, along with the carrying out of reaction, pH value raises gradually, material The color deepens, and finally the pH is greater than or equal to 11, and the color becomes reddish black, and is refluxed for 1 hour. Cool down, let stand to separate and remove the water laye...

Embodiment 2

[0016] Add 760g of 90% concentrated sulfuric acid to a 1000mL three-neck flask, start stirring, slowly add 208.2g of BBA to the flask, and finish adding in 1 hour. The process temperature was kept between 5-15°C and kept warm for 3 hours. Then the reactant was slowly added dropwise to a large amount of water at 10° C. to solidify for 2 hours, stirred for 2 hours, and suction filtered to obtain the solidified substance.

[0017] Take 200g of the cured product and add it to a 500mL three-necked flask, slowly add 50g of water, 20g of Na 2 CO 3 The lye formed with 20g of NaOH, and 150g of toluene was added, stirred and heated. As the reaction progressed, the pH value gradually increased, and the color of the material deepened. Finally, when the pH was greater than or equal to 11, the color became reddish black, and refluxed for 1 hour. Cool down, stand still to separate and remove the water layer, add 80g of toluene to wash, then add water to distill to remove the toluene, filte...

Embodiment 3

[0019] Add 760g of 102% concentrated sulfuric acid to a 1000mL three-neck flask, start stirring, slowly add 208.2g of BBA to the flask, and finish adding in 2 hours. After the BBA is completely dissolved, slowly add 104.1g of DPA and finish adding in 3 hours. The temperature is kept between 20-40°C and kept warm for 5-6 hours. Then the reactant was slowly added dropwise to a large amount of water at 20° C. to solidify for 2 hours, stirred for 4-6 hours, and then suction filtered to obtain the solidified substance.

[0020] Take 200g of the cured product and add it to a 500mL three-necked flask, slowly add 80g of water, 30g of Na 2 CO 3 The lye formed with the NaOH of 20g, and add 200g of toluene, stir, heat, along with the carrying out of reaction, pH value increases gradually, and material color deepens, and finally pH ≥ 10, color becomes reddish black, reflux 2 hours. Cool down, let stand to separate and remove the water layer, add 150g of toluene to wash, add activated ca...

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Abstract

The invention provides a preparation method of a heat sensitive dyestuff 3-dibutylamino-6-methyl-7-phenylaminofluoran (ODB2) and 2-methyl-4-methoxyl- diphenylamine (DPA) is adopted as raw material. ODB2 produced via the preparation method of the invention has high yield, high content, far lower impurity content compared with that of like products and good color, and can meet the requirements of international market and significantly reduce the production cost.

Description

technical field [0001] The invention relates to a preparation method of thermosensitive dyes, in particular to a preparation method of 3-dibutylamino-6-methyl-7-anilinofluorane (ODB2). Background technique [0002] Thermosensitive dyes are important functional dyes, mainly used in color couplers for thermosensitive recording paper. The thermosensitive dye itself is a colorless color base, which must be treated with a sensitive material to obtain a microcapsule coated with a layer of sensitive material, which acts on the sensitive material under changes in environmental conditions, such as temperature. When activated, the capsule ruptures, releasing the chromogen, which then reacts with the developer to produce the actual colored dye. [0003] In 1950, the crystal violet lactone CVL developed by NCR Corporation of the United States was the earliest thermosensitive dye. In 1969, the company developed the black fluoran compound ODB1, creating a new generation of thermosensitiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09B11/24
Inventor 李俊辉
Owner 李俊辉