Water-soluble photochromic compound as well as preparation method and application thereof

A photochromic and compound technology, applied in the field of dyeing and finishing chemistry, can solve the problems of lack of photochromic dyes, poor color fastness to washing, low solubility, etc., to reduce the harm to human health, good soaping fastness, Enhanced Solubility Effect

Inactive Publication Date: 2021-11-12
JIANGNAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the existing organic photochromic dyes are insoluble in water or have low solubility in water. Dyeing needs to rely on organic solvents, and the cost is high. The volatilization of organic solvents during the dyeing process and the residual solvents after washing after dyeing will cause certain harm to the human body.
For a small amount of water-soluble organic photochromic dyes, the color fastness to washing after dyeing by conventional methods is very poor
Existing photochromic dyes dye wool by means of mordant dyeing process or microcapsule coating and adhesion, and there is a lack of photochromic dyes that can directly dye wool at low temperature

Method used

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  • Water-soluble photochromic compound as well as preparation method and application thereof
  • Water-soluble photochromic compound as well as preparation method and application thereof
  • Water-soluble photochromic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A water-soluble photochromic compound and a preparation method thereof, using phenylhydrazine-4-sulfonic acid, 3-methyl-2-butanone, potassium hydroxide, 5-nitrosalicylaldehyde and methyl iodide as raw materials, including Follow the steps below:

[0038] 1. Dissolve phenylhydrazine-4-sulfonic acid (4.0g, 20mmol) and 3-methyl-2-butanone (3.4g, 40mmol) in glacial acetic acid, heat to 120°C in a round bottom flask, nitrogen atmosphere Reflux under protection and react for 14h.

[0039] 2. Ethyl acetate was added to wash twice and the pink solid powder was filtered out and dried in vacuum.

[0040] 3. Dissolve the powder in methanol, add saturated potassium hydroxide solution in isopropanol dropwise, stir in a beaker at room temperature for 2 hours, filter, and dry indole sulfonate.

[0041] 4. Indole sulfonate (4.0g, 14mmol) and methyl iodide (3.0g, 21mmol) were dissolved in acetonitrile, heated to 80°C in a round bottom flask, refluxed for 48h under nitrogen atmosphere,...

Embodiment 2

[0044] A water-soluble photochromic compound and a preparation method thereof, using phenylhydrazine-4-sulfonic acid, 3-methyl-2-butanone, potassium hydroxide, 5-nitrosalicylaldehyde and bromooctane as raw materials, Including the following steps:

[0045] 1. Dissolve phenylhydrazine-4-sulfonic acid (4.0g, 20mmol) and 3-methyl-2-butanone (3.4g, 40mmol) in glacial acetic acid, heat to 120°C in a round bottom flask, nitrogen atmosphere Reflux under protection and react for 14h.

[0046] 2. Ethyl acetate was added to wash twice and the pink solid powder was filtered out and dried in vacuum.

[0047] 3. Dissolve the powder in methanol, add saturated potassium hydroxide solution in isopropanol dropwise, stir in a beaker at room temperature for 2 hours, filter, and dry indole sulfonate.

[0048] 4. Dissolve indole sulfonate (4.0g, 14mmol) and bromooctane (4.1g, 21mmol) in acetonitrile, heat to 80°C in a round bottom flask, reflux for 48h under nitrogen atmosphere, filter and dry t...

Embodiment 3

[0052] A water-soluble photochromic compound and a preparation method thereof, using phenylhydrazine-4-sulfonic acid, 3-methyl-2-butanone, potassium hydroxide, 5-nitrosalicylaldehyde and hexadecane bromide as Raw materials, including the following steps:

[0053] 1. Dissolve phenylhydrazine-4-sulfonic acid (4.0g, 20mmol) and 3-methyl-2-butanone (3.4g, 40mmol) in glacial acetic acid, heat to 120°C in a round bottom flask, nitrogen atmosphere Reflux under protection and react for 14h.

[0054] 2. Ethyl acetate was added to wash twice and the pink solid powder was filtered out and dried in vacuum.

[0055] 3. Dissolve the powder in methanol, add saturated potassium hydroxide solution in isopropanol dropwise, stir in a beaker at room temperature for 2 hours, filter, and dry indole sulfonate.

[0056] 4. Indole sulfonate (4.0g, 14mmol) and hexadecane bromide (6.4g, 21mmol) were dissolved in acetonitrile, heated to 80°C in a round bottom flask, refluxed for 48h under nitrogen atmo...

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Abstract

The invention relates to a water-soluble photochromic compound as well as a preparation method and application thereof, and belongs to the field of dyeing and finishing chemistry. The water-soluble photochromic compound is prepared by dissolving a phenylhydrazine derivative and a ketone compound in an organic solvent, heating, and adding alkali, halogenated alkane and a salicylaldehyde derivative after complete reaction. According to the water-soluble photochromic compound, sulfonate ions having extremely high water solubility are introduced into spiropyrane molecules, so that the solubility of the spiropyrane molecules in water is greatly improved, use of organic solvents is avoided in the dyeing process, and the production cost and harm to human health are reduced. The dyeing rate of the water-soluble photochromic compound at the low temperature of 60 DEG C can reach 85%, and after the water-soluble photochromic compound is washed according to the national standard, the staining grade of lining cloth is higher than 4, and the color fastness is high.

Description

technical field [0001] The invention relates to the technical field of dyeing and finishing chemistry, in particular to a water-soluble photochromic compound and its preparation method and application. Background technique [0002] Photochromic materials refer to certain compounds A that are subjected to a certain wavelength λ 1 The action of light, the molecular structure will change to generate another compound B, another wavelength λ 2 Under the action of light or heat, compound A is reversely generated, and the absorption spectra of compounds A and B have obvious differences and show different colors. [0003] Organic photochromic materials include fulgid anhydrides, diarylethenes, azobenzenes, spiropyrans, and naphthoquinones, which are widely used in anti-counterfeiting, computer storage, textiles, clothing, construction, molecular switches, etc. field. Among them, spiropyran compounds are widely used. After a certain light stimulation, the carbon-oxygen bond at the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K9/02D06P3/14
CPCC07D491/107C09K9/02D06P3/14C09K2211/1033
Inventor 孙昌薛惊理柳赟雯金光王潮霞陈文浩
Owner JIANGNAN UNIV
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