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Seven-membered fluorine boron fluorescent dye and application thereof in fluorescent anti-counterfeiting film

A technology of fluorescent dyes and fluorine boron, applied in the field of fluorescent dyes, can solve the problem that the hidden technology cannot be found, and achieve the effects of high solid fluorescence quantum yield, large fluorescence quantum yield and low manufacturing cost.

Pending Publication Date: 2021-07-13
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This technology has a very high degree of concealment, and the hidden technology cannot be found by naked eyes and touch. When identifying its authenticity, testing instruments must be used
Therefore, fluorescent dyes need to have the characteristics of easy printing and high fluorescence intensity. In addition, the preparation cost of fluorescent dyes is low, the preparation method is simple, the yield is high, and green energy saving and environmental protection are also great tests for manufacturers. Existing It is difficult for anti-counterfeiting fluorescent dyes to meet all the above conditions

Method used

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  • Seven-membered fluorine boron fluorescent dye and application thereof in fluorescent anti-counterfeiting film
  • Seven-membered fluorine boron fluorescent dye and application thereof in fluorescent anti-counterfeiting film
  • Seven-membered fluorine boron fluorescent dye and application thereof in fluorescent anti-counterfeiting film

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Weigh 2,3,3-trimethylindole (632mg, 4mmol), take 100.00mL of toluene, mix and dissolve, then add 2-acetylpyrrole (436mg, 4mmol), piperidine (0.36mL, 4mmol), Acetic acid (0.24mL, 4mmol) and phosphorus oxychloride (0.44mL, 4mmol) were heated and stirred at 120°C for 24 hours to complete the reaction. ).

[0027] If the reaction raw material is 2,3,3-trimethylindole, the yield of compound 3 is extremely low, which is not conducive to the collection of compound I. If the yield of compound 3 is high, it is beneficial to the collection of compound 1.

Embodiment 2

[0029] Weigh the protonated 2,3,3-trimethylindole (640mg, 4mmol) of compound 1, take 100.00mL toluene, mix and dissolve, then add 2-acetylpyrrole (436mg, 4mmol), piperidine ( 0.36mL, 4mmol), acetic acid (0.24mL, 4mmol), phosphorus oxychloride (0.44mL, 4mmol) were heated and stirred at 120°C for 24 hours to complete the reaction, and the reactant was rotary evaporated, and purified by column chromatography to obtain light yellow solid 3 ( 120 mg, yield 12%). Take the above compound 3 (120mg, 0.48mmol), take 30ml of toluene solution, 1.00ml of triethylamine, slowly add boron trifluoride ether solution (1.00ml) dropwise under electromagnetic stirring, raise the temperature to 120°C, and reflux After 30 min, TLC plate detection, the product was washed with water, extracted, dried, rotary evaporated, filtered and purified to obtain compound I as a yellow solid (123 mg, yield 86%).

[0030]

Embodiment 3

[0032] Weigh the protonated 2,3,3-trimethylindole (960mg, 6mmol) of compound 1, mix and dissolve 100.00mL toluene, then add 2-acetylpyrrole (436mg, 4mmol) and piperidine ( 0.36mL, 4mmol), acetic acid (0.24mL, 4mmol), phosphorus oxychloride (0.44mL, 4mmol) were heated and stirred at 120°C for 20 hours to complete the reaction, the reactant was rotary evaporated, and purified by column chromatography to obtain a light yellow solid 3 ( 340 mg, yield: 34%). Take the above compound 3 (120mg, 0.48mmol), take 30ml of toluene solution, 1.50ml of triethylamine, slowly add boron trifluoride ether solution (1.50ml) dropwise under electromagnetic stirring, raise the temperature to 120°C, and reflux After 30 min, TLC plate detection, the product was washed with water, extracted, dried, rotary evaporated, filtered and purified to obtain compound I as a yellow solid (132 mg, yield 92%). When the amount of Compound 1 was increased by 1.5 times (relative to Example 1), the yield of Compound 3...

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Abstract

The invention discloses a seven-membered fluorine boron fluorescent dye and application thereof on a fluorescent anti-counterfeiting film. The structure of the dye is as shown in a formula which is described in the specification. The seven-membered fluorine boron fluorescent dye is prepared from protonated 2,3,3-trimethylindole and 2-acetylpyrrole serving as raw materials through a Knoevenagel condensation reaction under the action of acetic acid, piperidine and a phosphorus oxychloride catalyst. The dye and acrylic resin realizes film forming on a thin film; and the obtained film is yellow green under natural light, and clear fluorescence can be seen under an ultraviolet lamp. The fluorescent dye is simple and easy to obtain, low in manufacturing cost, high in solid fluorescence quantum yield, high in film forming speed with acrylic resin on the thin film and huge in potential in the aspects of fluorescent holographic anti-counterfeiting packaging films, OLDE and the like.

Description

technical field [0001] The invention relates to the field of fluorescent dyes, in particular to a seven-membered fluoroboron fluorescent dye and its application on fluorescent anti-counterfeiting films. Background technique [0002] In recent years, technology has developed very rapidly. The emergence of digital cameras, scanners, and printers has enabled counterfeiters to use personal computers to produce high-quality fakes, and they make huge profits from it. Counterfeiters not only infringe on other people's copyrights, but also cause great harm to society. Counterfeit banknotes, for example, have caused serious economic and social problems. In addition, counterfeit medicines put patients at great risk of getting sick. Fake and shoddy products, terrorist attacks, and drug trafficking have become the world's three major public hazards. It has caused great difficulties for people's identification and brought huge losses to the country. [0003] We need to develop new an...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B23/04C09D133/04C09D5/22
CPCC07F5/022C09K11/06C09B23/04C09D133/04C09D5/22C09K2211/1055C08K5/55
Inventor 张诺诺袁晓慧陈茜晏佳莹刘德保李德江
Owner CHINA THREE GORGES UNIV
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