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2-(2-Hydroxyphenyl) benzothiazole derivatives and their preparation methods and their application in fluorescent anti-counterfeiting

A benzothiazole and hydroxyphenyl technology, which is applied in the field of fluorescent materials and anti-counterfeiting applications, can solve the problems of high fluidity of fluorescent ink, fast attenuation of fluorescent intensity, low viscosity of fluorescent ink, etc., and is convenient for large-scale application and promotion. Stable and fast response

Active Publication Date: 2022-08-09
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For anti-counterfeiting fluorescent materials, rare earth metal complexes are the most researched at present, and these compounds have the following defects: 1) The fluorescence intensity decays quickly after being placed for a long time; 2) Organic rare earth fluorescent complexes have low viscosity due to the low viscosity of fluorescent inks It is very easy to cause emulsification during printing, resulting in floating dirt or ink roller deinking, especially colorless transparent ink, which needs to be checked frequently to prevent missing printing due to deinking, and the effect of offset printing is not ideal. This kind of fluorescent ink is generally not used in lithographic printing, and its application range is narrow; 3) Fluorescent ink has high fluidity and slow drying, which is extremely inconvenient
In addition, most of the fluorescent anti-counterfeiting materials currently used are monochromatic fluorescent
Therefore, the effectiveness and safety of traditional fluorescent anti-counterfeiting are facing serious challenges

Method used

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  • 2-(2-Hydroxyphenyl) benzothiazole derivatives and their preparation methods and their application in fluorescent anti-counterfeiting
  • 2-(2-Hydroxyphenyl) benzothiazole derivatives and their preparation methods and their application in fluorescent anti-counterfeiting
  • 2-(2-Hydroxyphenyl) benzothiazole derivatives and their preparation methods and their application in fluorescent anti-counterfeiting

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1. Preparation of 2-(2-hydroxyphenyl) benzothiazole derivatives

[0047] In a 25 mL round bottom flask, 306 mg (1 mmol) of 2-benzothiazolyl-4-bromophenol was dissolved in 10 mL of tetrahydrofuran, and then 2 mL of potassium carbonate aqueous solution (concentration 2 mM) was added under nitrogen atmosphere. Next, 288 mg (1 mmol) of 4-(9-carbazolyl) benzeneboronic acid was added to the reaction mixture, and after stirring at room temperature for 10 minutes, Pd(PPh 3 ) 4 (58 mg, 0.05 mmol) was added to the reaction solution. After the mixture was stirred at 80°C for 8 hours, 5 mL of purified water was added to quench the reaction. Extracted with dichloromethane three times, the combined organic layers were washed with water and dried over sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and left to crystallize to obtain 270 mg of orange-yellow 2-(2-hydroxyphenyl)benzothiazole derivative solids in a yield of 270 mg. was 57.6%.

[...

Embodiment 2

[0056] Example 2. Application of 2-(2-hydroxyphenyl) benzothiazole derivatives in anti-counterfeiting

[0057] (1) preparing a tetrahydrofuran solution of 2-(2-hydroxyphenyl)benzothiazole derivative with a concentration of 50 μM to obtain an anti-counterfeiting solution;

[0058] (2) Arrange the anti-counterfeiting liquid on the anti-counterfeiting commodity, and after drying, irradiate with 365nm ultraviolet light, and the part where the anti-counterfeiting substance is arranged emits yellow fluorescence;

[0059] (3) Place the anti-counterfeiting product in an amine vapor atmosphere for 30 seconds, then irradiate it with 365nm ultraviolet light, and the part where the anti-counterfeiting substance is set emits blue-green fluorescence;

[0060] (4) The anti-counterfeiting goods are smoked in an acetic acid vapor atmosphere for 30 seconds to restore the yellow fluorescence and realize the reversible response of solid-state fluorescence.

experiment example 1

[0061] Experimental Example 1: Testing of Sensing Properties of 2-(2-Hydroxyphenyl)benzothiazole Derivatives

[0062] Test method: Add 10 μL of 50 μM tetrahydrofuran solution of 2-(2-hydroxyphenyl)benzothiazole derivatives to a 0.8cm×1.5cm filter paper strip, and then dry it in the air for 24 hours to prepare Filter paper strips loaded with fluorescent dyes.

[0063] Amine vapor was prepared by placing isopropylamine (15 μL) in a 1 cm×1 cm×4 cm quartz cuvette, sealed, and left at room temperature for 30 minutes to saturate.

[0064] The dye-loaded filter paper strips were mounted on a glass plate, which was placed in a quartz cuvette. Place the cuvette with the glass plate mounted on the solid sample holder of the fluorescence spectrometer and test its fluorescence spectrum. The filter paper strip was placed in isopropylamine vapor for 30 seconds and its fluorescence spectrum was tested. The filter paper strip was taken out, dried with a hair dryer for 1 minute, then placed...

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Abstract

The present invention relates to 2-(2-hydroxyphenyl) benzothiazole derivatives, a preparation method thereof and application in fluorescence anti-counterfeiting. The 2-(2-hydroxyphenyl) benzothiazole derivatives have formula (I) The structure shown, the 2-(2-hydroxyphenyl) benzothiazole derivative of the present invention has strong fluorescence intensity, stable material properties, can be placed for a long time, has fast and reversible response to amine vapor and acetic acid vapor, and realizes two-color fluorescence display. , The fluorescence contrast of the two colors is high, which can be distinguished by the naked eye. When used as a fluorescent anti-counterfeiting material, it can be quickly identified, and the efficiency and safety of the anti-counterfeiting technology are improved.

Description

technical field [0001] The invention relates to a 2-(2-hydroxyphenyl)benzothiazole derivative, a preparation method thereof and an application in fluorescent anti-counterfeiting, belonging to the technical field of fluorescent materials and anti-counterfeiting applications. Background technique [0002] With the continuous development of the global economy, counterfeit goods appear frequently, causing serious economic losses every year. However, consumers cannot clearly identify the authenticity of goods, resulting in more and more counterfeiting. In today's society, almost every important and expensive commodity can be counterfeited, including banknotes, securities, checks, documents, invoices, medicines, cosmetics and food. As a social phenomenon, counterfeit and shoddy goods have become a common concern of all countries in the world. Many countries in the world, especially some developed countries, have invested a lot of effort in developing various anti-counterfeiting te...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/10C09K11/06B42D25/36
CPCC07D417/10C09K11/06B42D25/36C09K2211/1029C09K2211/1037
Inventor 张大同李斌
Owner QILU UNIV OF TECH
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