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Dihydroxy fluorescence chain extender based on carbazole derivative and preparation and application thereof

A carbazole derivative and dihydroxyl technology, applied in the field of synthesizing copolymerized fluorescent WPU, can solve the problems of poor light fastness and scrub fastness, poor compatibility, uneven color distribution, etc., and achieve stable and long-lasting fluorescent performance. , excellent solvent resistance, simple preparation process

Active Publication Date: 2017-06-13
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Colored water-based polymer products prepared by blending polymer emulsions with pigments or dyes have been widely used in water-based paints, water-based inks and other fields, but due to the poor compatibility between pigments or dyes and water-based polymers , often lead to many problems, such as the precipitation of pigments during storage, uneven color distribution during use, poor color fastness to light and washing fastness to washing, etc.

Method used

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  • Dihydroxy fluorescence chain extender based on carbazole derivative and preparation and application thereof
  • Dihydroxy fluorescence chain extender based on carbazole derivative and preparation and application thereof
  • Dihydroxy fluorescence chain extender based on carbazole derivative and preparation and application thereof

Examples

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Effect test

Embodiment 1

[0051](1) Mix 5g of carbazole, 5.36g of 3-bromopropyne, 1.8g of sodium hydroxide and 100ml of DMF solvent, stir and dissolve until the system becomes a transparent solution, heat the oil bath to 50°C and stop it after 24 hours of constant temperature reaction;

Embodiment 2

[0055] (1) 5 g of intermediate 9-propynyl carbazole, 1.81 g of bishydroxy azide (dihydroxy azide compound of formula I) (the molar ratio of 9-propynyl carbazole and bis hydroxyl azide is 2.5 : 1), cuprous chloride solid 0.610g and sodium ascorbate 0.725g are dissolved in the mixed solvent of 100ml (the volume ratio of DMF and distilled water is 9:1), vacuumize, pass nitrogen to replace air several times, and keep nitrogen flow Rate, under nitrogen atmosphere, magnetic stirring at room temperature by click reaction 1h;

[0056] (2) Distilled water was added to precipitate after the reaction, and a light yellow solid was precipitated. After washing with distilled water and filtering three times, cyclohexane was added for recrystallization and filtered to obtain a light yellow solid, which was dried in a blast oven at 75°C (18h), and obtained based on The dihydroxy fluorescent chain extender of carbazole derivatives is 4.89g, the theoretical yield is 5.80g, and the yield is 84.3%...

Embodiment 3

[0059] (1) Intermediate 9-propynyl carbazole 5g, bishydroxy azide (dihydroxy azide compound of formula I) 2.27g (9-propynyl carbazole and bis hydroxyl azide molar ratio is 2 : 1), 0.610g of cuprous chloride solid and 0.725g of sodium ascorbate are dissolved in 100ml of mixed solvent (the volume ratio of DMF and distilled water is 9:1), vacuumize, replace the air with nitrogen several times, and maintain the nitrogen flow Rate, under nitrogen atmosphere, magnetic stirring at room temperature by click reaction 1h;

[0060] (2) Distilled water was added after the reaction, and a light yellow solid precipitated out. After washing with distilled water and filtering three times, cyclohexane was added to recrystallize and filtered to obtain a light yellow solid, which was dried in a blast oven at 75°C (18h) to obtain a carba-based The dihydroxy fluorescent chain extender of azole derivatives is 6.13g, the theoretical yield is 7.27g, and the yield is 84.3%.

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Abstract

The invention belongs to the technical field of organic materials and discloses a dihydroxy fluorescence chain extender based on a carbazole derivative and preparation and application thereof. The method comprises the following steps: (1) under alkaline condition, an organic solvent is used as a reaction medium, carbazole and propargyl bromide react and subsequent processing is carried out to obtain an intermediate 9-propynyl carbazole; the molar ratio of carbazole to propargyl bromide is 1: 1.1-2; and (2) in the atmosphere of inert gas and in the presence of a catalyst and a reducing agent, the intermediate 9-propynyl carbazole and dihydroxy azide react in a solvent, and subsequent processing is carried out to obtain the dihydroxy fluorescence chain extender based on the carbazole derivative. The chain extender has high yield, has high fluorescence intensity and good anti-ultraviolet stability, and is used in manufacturing of a fluorescence WPU emulsion.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and relates to a dihydroxy fluorescent chain extender based on carbazole derivatives and a preparation method thereof, as well as a method for synthesizing copolymerized fluorescent WPU using it as a chain extender. Background technique [0002] Polyurethane (PU), as a synthetic resin with excellent performance, has a very wide range of applications. Traditional PU materials are usually dissolved and diluted with organic solvents. When the film is formed and solidified, a large amount of organic solvents volatilize, causing serious environmental pollution. The PU is dispersed in water and exists in the form of emulsion, which has excellent environmental performance. Moreover, fluorescent materials based on waterborne polyurethane are also frequently used in anti-counterfeiting technology, printing ink, life science, information storage and national defense. [0003] Although fluoresce...

Claims

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Application Information

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IPC IPC(8): C08G18/48C08G18/66C08G18/75C08G18/10C08G18/34C08G18/38C07D403/14C07D403/06C09K11/06
Inventor 胡剑青丁伟涂伟萍彭开美邹滔王若男
Owner SOUTH CHINA UNIV OF TECH
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