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A kind of synthetic method of perylene red dye perylene red 620

A synthesis method and red dye technology, which are applied in the field of synthesis of perylene red dye perylene red 620, can solve the problems of long synthesis time, affecting the production and application of perylene red 620, and high reaction temperature, and achieve low cost, strong practicability, and high-quality products. The effect of high purity

Active Publication Date: 2020-11-24
SOUTHWEAT UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the synthesis method of perylene red 620 in the prior art: 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride and 2,6-diisopropylaniline are used to synthesize intermediates Propionic acid needs to be used as a solvent, and it needs to be refluxed at 140°C for 24 hours. There are disadvantages such as high reaction temperature, long synthesis time, and the product needs to be purified by column chromatography; in the existing synthesis of perylene red 620, the purification method mainly remains Problems such as the use of new steaming solvent quinoline or toxic solvent nitrobenzene, high reaction temperature, and column chromatography purification, the purity of perylene red 620 obtained by the existing synthesis and purification method is 84.5%, and these problems have seriously affected the performance of perylene red 620 production and application

Method used

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  • A kind of synthetic method of perylene red dye perylene red 620
  • A kind of synthetic method of perylene red dye perylene red 620
  • A kind of synthetic method of perylene red dye perylene red 620

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Effect test

Embodiment 1

[0038] A method for synthesizing perylene red dye perylene red 620, namely a method for efficiently synthesizing and purifying perylene red dye perylene red 620, is carried out according to the following steps:

[0039]a. Efficient preparation of N,N'-bis(2,6-diisopropyl)phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide :

[0040] Under the protection of inert gas, 10mmol 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride, 40mmol 2,6-diisopropylaniline and 0.1mmol zinc chloride were added to In 1300mmol propionic acid, react at 120°C for 8 hours, stand at 25°C for 12 hours, filter with suction, wash with water until the filtrate is neutral, and dry at 80°C to obtain orange powder N,N'-bis(2,6-diisopropyl Base) phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide 7.2g, the yield was 85%, and the purity was 91%;

[0041] b. Preparation and efficient purification of perylene red 620:

[0042] 10mmol N,N'-bis(2,6-diiso...

Embodiment 2

[0045] A method for synthesizing perylene red dye perylene red 620, namely a method for efficiently synthesizing and purifying perylene red dye perylene red 620, is carried out according to the following steps:

[0046] a. Efficient preparation of N,N'-bis(2,6-diisopropyl)phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide :

[0047] Under the protection of inert gas, add 10mmol 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride, 40mmol 2,6-diisopropylaniline and 0.1mmol anhydrous zinc acetate Add 1300mmol propionic acid, react at 125°C for 8 hours, stand at 25°C for 12 hours, filter with suction, wash with water until the filtrate is neutral, and dry at 80°C to obtain N,N'-bis(2,6-diiso Propyl)phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide 7.5g, yield 88%, purity 92%;

[0048] b. Preparation and efficient purification of perylene red 620:

[0049] 10mmol N,N'-bis(2,6-diisopropyl)phenyl-1,6,7,12-tetrachloro-3,4...

Embodiment 3

[0052] A method for synthesizing perylene red dye perylene red 620, namely a method for efficiently synthesizing and purifying perylene red dye perylene red 620, is carried out according to the following steps:

[0053] a. Efficient preparation of N,N'-bis(2,6-diisopropyl)phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide :

[0054] Under the protection of inert gas, add 10mmol 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride, 40mmol 2,6-diisopropylaniline and 0.1mmol zinc acetate dihydrate Add 1300mmol propionic acid, react at 115°C for 8 hours, stand at 25°C for 12 hours, filter with suction, wash with water until the filtrate is neutral, and dry at 80°C to obtain N,N'-bis(2,6-diiso Propyl)phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide 7.3g, yield 86%, purity 92%;

[0055] b. Preparation and efficient purification of perylene red 620:

[0056] 10mmol N,N'-bis(2,6-diisopropyl)phenyl-1,6,7,12-tetrachloro-3,4...

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Abstract

The invention discloses a synthetic method of perylene red 620 as perylene red dye. The method is characterized by comprising the following steps: 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylicdianhydride is taken as a raw material and subjected to a reaction with 2,6-diisopropylanilineby catalysis of a catalyst under protection of inert gas, and the intermediate N,N'-bis(2,6-diisopropyl)phenyl-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic diimide is obtained; the intermediate is subjected to a reaction with phenol, and a crude perylene red 620 product is obtained; the crude product is washed and subjected to other processing, and perylene red 620 with higher purity is obtained. After introduction of the catalyst, synthetic reaction temperature of the intermediate is reduced, and reaction time is shortened by 2 / 3; the original column chromatographic process is replaced with a cooling, standing and suction filtration method, and accordingly, purity of the intermediate isimproved; the method has the characteristics of safe and reasonable process, simple processing steps, high yield, low cost, high product purity and the like.

Description

technical field [0001] The invention belongs to the preparation of dyes, and relates to a synthesis method of perylene red dye perylene red 620. The perylene red dye perylene red 620 prepared by the invention is especially suitable for the original finish paint and repair paint of high-temperature processing plastics and automobiles. Background technique [0002] Perylene-based pigments are vat dyes with superior dyeing performance, strong chemical stability, high weather fastness, strong penetration resistance, and high temperature resistance. They have been widely used in high-temperature processing plastics and original topcoats and repair paints for automobiles. [0003] Perylene Red 620 is a fluorescent dye invented by BASF. Due to its high quantum fluorescence yield and large Stokes shift, it is a potential material for organic solar energy and organic light-emitting diodes. [0004] In the synthesis method of perylene red 620 in the prior art: 1,6,7,12-tetrachloro-3,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B5/62C09K11/06
CPCC09B5/62C09K11/06C09K2211/1029
Inventor 李鸿波陈明龙王小旭吴金婷孟俞富
Owner SOUTHWEAT UNIV OF SCI & TECH
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