Special fluorescent anti-counterfeit material and preparing method and application thereof

A fluorescence and product technology, applied in luminescent materials, chemical instruments and methods, applications, etc., to achieve the effects of comprehensive implied anti-counterfeiting information, broad application prospects, and stable product fluorescence performance

Active Publication Date: 2019-04-19
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, with the rapid development of luminescent material science, especially quantum dots, perovskite dots, carbon dots, graphene dots, silicon quantum, conjugated polymers, metal clusters and nanoparticles, organic metal framework compounds (MOF) With the emergence of many fluorescent materials, the anti-counterfeiting features that simply rely on the appearance of fluorescent patterns can be imitated or forged by other fluorescent materials with similar characteristics. Therefore, the effectiveness and safety of traditional fluorescent anti-counterfeiting are facing serious challenges.

Method used

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  • Special fluorescent anti-counterfeit material and preparing method and application thereof
  • Special fluorescent anti-counterfeit material and preparing method and application thereof
  • Special fluorescent anti-counterfeit material and preparing method and application thereof

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preparation example Construction

[0055] The present invention provides the preparation method of the compound shown in above-mentioned formula (I), described method comprises the steps:

[0056] 1) 3,4,9,10-perylenetetracarboxylic anhydride, R-NH 2 1. Mix the catalyst into quinoline or imidazole; or without adding quinoline or imidazole, under the protection of argon atmosphere, control the reaction temperature at 120-250°C, and stir for 4-48h;

[0057] 2) During the cooling process, before the mixture obtained from the above reaction is solidified, pour it into the precipitant, stir for 30min-6h, let stand, settle, filter, wash, dry, and finally obtain purified solid powder through silica gel column separation ; Wherein, R is as defined above.

[0058] Preferably, in the synthesis step, according to the different types of reactant organic amines, the catalyst can be diethanolamine or zinc acetate, and the stoichiometric ratio of 3,4,9,10-perylenetetracarboxylic anhydride to the catalyst is 1:0 to 1:5.

[...

preparation example 1

[0064] Preparation Example 1: Synthesis of Compound X6 (R groups are the same, selected from the above-mentioned 2,4,6-trimethylphenyl group with the number 6)

[0065]

[0066] 7.84g (20.0mmol) 3,4,9,10-perylenetetracarboxylic anhydride, 10.00g (74.0mmol) 2,4,6-trimethylaniline and 3.66g (20.0mmol) zinc acetate were miscible in 45.0mL In quinoline, the Schlenk line was used to freeze, vacuumize, and flush with argon three times. Finally, the above mixture was stirred and heated to 230° C. for 4 h under the protection of argon atmosphere to complete the reaction. After cooling, pour the above reactant into about 450mL of 75°C hot water, stir, stand still, precipitate, filter, wash with deionized water, and dry, and the solid sample obtained is separated by silica gel column (dichloromethane / methanol 2%) After purification, 9.40 g of reddish-brown solid powder was obtained, with a yield of 75%.

preparation example 2

[0067] Preparation Example 2: Synthesis of Compound X21 (R groups are the same, selected from the above-mentioned 4-adamantylphenyl group numbered 21)

[0068]

[0069] 3.92g (10mmol) of 3,4,9,10-perylenetetracarboxylic anhydride, 5.68g (25mmol) of 4-adamantyl aniline, and 60.00g (0.88mol) of imidazole were mixed uniformly, and the mixture was vacuum-puffed three times with argon. Under the protection of an argon atmosphere, stir and heat to 140° C. for 4 h to complete the reaction. After cooling, pour it into a mixed solution of 500mL ethanol / water / concentrated hydrochloric acid (volume ratio 25:10:1) while the mixture is still stirring, stir for 4.5h, let stand, settle, filter, wash with deionized water, and dry to obtain Brown solid, the crude product was separated and purified through a silica gel column (dichloromethane / methanol 2%) to obtain 4.21 g of red solid powder with a yield of 52%.

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Abstract

The invention provides a special fluorescent anti-counterfeit material and a preparing method and application thereof. The fluorescent anti-counterfeit material comprises a compound shown in the formula (I), a stabilizer and/or macromolecule resin. The raw materials involved in the preparing process of the fluorescent anti-counterfeit material are wide in source; the special fluorescent anti-counterfeit material is high in synthesis yield and stable in fluorescence performance, and can be directly printed after being mixed with commercial printing ink, large-scale application and popularization of anti-counterfeit labels are facilitated, and the application prospect is wide. The structure of the formula (I) is shown in the following description.

Description

technical field [0001] The invention relates to a special fluorescent anti-counterfeiting material and its preparation method and application, belonging to the field of organic fluorescent materials and anti-counterfeiting applications. Background technique [0002] Fluorescence anti-counterfeiting technology is an anti-counterfeiting technology widely used in current currencies, certificates, bills, securities and high-end brand-name goods. It has many characteristics such as high throughput, high recognition, simple identification, and good security. (overt), concealment (covet), judicial identification (forensic) and other modes or levels of anti-counterfeiting requirements. On this basis, combined with marking and tracking and information technology, anti-counterfeiting tracking (track and trace) and traceability can also be realized. In addition, the fluorescent material is prepared into fluorescent ink, and large-scale printing of anti-counterfeiting marks can be real...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09K11/02C09D11/101C09D11/50C08K5/3437C08L1/12C08L5/16
CPCC08K5/3437C09D11/101C09D11/50C09K11/025C09K11/06C08L1/12C08L5/16
Inventor 田卫国王舒林江恒张军
Owner INST OF CHEM CHINESE ACAD OF SCI
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