CN112745832A - Method for preparing fluorescent anti-counterfeiting material - Google Patents
Method for preparing fluorescent anti-counterfeiting material Download PDFInfo
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- CN112745832A CN112745832A CN202110164831.2A CN202110164831A CN112745832A CN 112745832 A CN112745832 A CN 112745832A CN 202110164831 A CN202110164831 A CN 202110164831A CN 112745832 A CN112745832 A CN 112745832A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
Abstract
The invention provides a preparation method of a fluorescent anti-counterfeiting material, which comprises the following steps: (1) preparing a solution of one or more fluorescent materials; (2) preparing a solution of a high molecular polymer; (3) mixing and stirring the prepared high molecular polymer solution and the prepared fluorescent dye solution uniformly to obtain a uniform solution for later use; (4) mixing the uniform solution obtained in the step (3) with a poor solvent of a high molecular polymer, so that the fluorescent dye can be encapsulated by the high molecular particles, and the fluorescent anti-counterfeiting material is obtained; the fluorescent anti-counterfeiting material prepared by the invention has the advantages of small and uniform particles, strong anti-interference capability, good encryption effect and the like, and can further improve the encryption degree by adding interferents.
Description
Technical Field
The invention belongs to the technical field of luminescence and display, and particularly relates to a method for preparing an ultrastable fluorescent anti-counterfeiting material.
Background
Counterfeiting and forgery are a global problem that poses a security threat to individuals, companies and society. The fluorescent anti-counterfeiting material has the advantages of easy identification, good operation, high encryption degree and the like, so the fluorescent anti-counterfeiting material is widely applied to the fields of currency anti-counterfeiting, file encryption, diploma and tax receipt encryption and the like.
At present, fluorescent anti-counterfeiting materials are classified into various categories, and the categories of commonly used anti-counterfeiting materials mainly comprise:
(1) anti-counterfeiting paper. Such as fiber paper, watermark paper safety line paper peeling fragile paper anti-scratch (scraping) correction paper, anti-copy paper anti-correction copy paper, anti-counterfeiting holographic paper and the like.
(2) An anti-counterfeiting film. Such as holographic anti-counterfeiting films, microporous anti-counterfeiting films, fragile anti-counterfeiting films, and the like.
(3) Anti-counterfeiting ink. Such as ultraviolet excited fluorescent anti-counterfeiting ink, optical color-changing anti-counterfeiting ink, sunlight excited color-changing anti-counterfeiting ink, infrared excited fluorescent anti-counterfeiting ink, electroluminescent ink, thermosensitive color-changing anti-counterfeiting ink, pressure-sensitive color-changing anti-counterfeiting ink, water-sensitive color-changing ink, magnetic anti-counterfeiting ink, anti-altering ink and the like.
(4) Anti-counterfeiting stamp-pad ink. Such as ultraviolet excited fluorescence anti-counterfeiting penetrating stamp-pad ink.
(5) Other anti-counterfeiting materials.
However, the anti-counterfeiting material prepared by the existing method has the defects of poor anti-counterfeiting stability, difficult ink-jet printing, non-uniform particles and high preparation cost.
An excellent anti-counterfeiting material has the characteristics of good tolerance, simple and convenient preparation method, large-scale production, high anti-counterfeiting safety, ink-jet printing of the anti-counterfeiting material, mobile phone photographing and identification, anti-decoding system and the like.
Disclosure of Invention
Aiming at the technical problems, the invention aims to provide a method for preparing a fluorescent anti-counterfeiting material with easy preparation, high encryption degree and ultra-stability.
A method for preparing a fluorescent anti-counterfeiting material with easy preparation, high encryption degree and ultra-stability comprises the following steps:
(1) preparing a solution of one or more fluorescent materials;
(2) preparing a solution of a high molecular polymer;
(3) mixing the prepared high molecular polymer solution and the prepared fluorescent dye solution, and uniformly stirring to obtain a uniform solution for later use;
(4) preparing a poor solvent for the high molecular polymer;
(5) and (4) mixing the uniform solution obtained in the step (3) with the poor solvent prepared in the step (4), so that the fluorescent dye can be encapsulated by the polymer particles, and the fluorescent anti-counterfeiting material is obtained.
Preferably, in step (3), the stirring time is 10 to 50 minutes.
Preferably, in the step (5), the mixing manner is direct mixing or mixing using a mixer.
Preferably, the fluorescent material comprises LR305, Fluorescein, rhodamine series dyes, Long Pepper, perylene, DPA, Coumarin series dyes, FITC, Calcein, 5-Carboxy Fluorescein, BODIPY series dyes, Alexa TM 546, Pyronin Y, Thiadiacarbyanine, Alexa TM, 6-Aminofluorscein, Dansyl Chloride, 4-Methylumbeferone, Aminochrome, Anthrocyte stearate, APC-Cy7, Atabrine, Aurophonine, Bisbenzamide, Catalamamine, Couchein Phalloidin, Dansyl Amine, Dansyl Chloride, Hydroxychrome, NBD, PerCP, Nile Red, Noradrenaline, Thioglein, Meexylasporin, Alaxacuminate series dyes, and 5-fluorescent dyes.
Preferably, the high molecular polymer comprises one or more of PLA, PLGA, PCL, P4VP, P2VP, PS, PVDF, PVDC, PP, PVF, PVFM, PVP, PVK, PVC, PVCA, PVCC, PVAC, PVAL, PTFE, PUR, PSU, PPA, PPE, PPO, PPs, POM, PMS, PMMA, PMP, PMCA, PISU, PIB, PI, PFF, PFA, PF, PET, PEO, PES, PETG, PEEK, PEI, PEBA, PE, PDAP, PDMS, PC, PCTFE, PBS, PBT, PBA, PBAN, PAT, PAUR, PAT, PASU, PAN, PAK, PAI, PAE, PA, CMC, PADC, ABS, ABA, AES, CA, CAB, CAP, CE, CF, and an artificially synthesized polymer.
Preferably, in the step (1), one or more fluorescent materials are dissolved in a good solvent of the fluorescent dye and stirred to obtain a solution of one or more fluorescent materials; wherein the good solvent of the fluorescent dye is one or more of acetonitrile, methanol, ethanol, acetone, DMF and THF; the mass fraction of the fluorescent dye is 0.0001-80 wt%, the stirring temperature is 30-180 ℃, and the stirring time is 10-500 min;
in the step (2), dissolving a high molecular polymer in the good solvent of the high molecular polymer, and stirring to obtain a solution of the high molecular polymer; wherein the polymer has good solubilityThe solvent is one or more of acetonitrile, methanol, ethanol, acetone, DMF and THF, and the concentration of the high molecular polymer is 0.001-180 mg mL-1Stirring at 30-180 ℃ for 10-500 min;
in the step (3), the mass ratio of the high molecular polymer to the fluorescent dye in the uniform solution is 0.00001-100000;
in the step (4), the poor solvent is water;
in the step (5), the volume ratio of the uniform solution to the poor solvent is 0.0001-100.
Preferably, in the step (1), the mass fraction of the fluorescent dye is 0.001-20 wt%; in the step (2), the concentration of the high molecular polymer is 0.01-80 mg mL-1(ii) a In the step (3), the mass ratio of the high molecular polymer to the fluorescent dye in the uniform solution is 0.001-1000; in the step (5), the volume ratio of the uniform solution to the poor solvent is 0.001-100.
Preferably, the method further comprises the steps of: in order to prevent the dye component from being cracked, a water-insoluble interfering substance can be added in the step (3), and then the mixture is heated at 40-180 ℃ and stirred for 5-500 min, so that the interfering substance is completely dissolved. The mass spectrum result of the anti-counterfeiting ink particles shows that the characteristic peak of the dye is submerged in the spectrum, and the specific components of the dye are difficult to read.
Preferably, the interferent is selected according to the type of dye and the type of polymer, provided that the anti-counterfeiting quality is not affected. The commonly used interferents may be selected from crude high molecular polymers and crude fluorescent dyes. The addition amount is 0.01 wt% -60 wt% of the polymer and fluorescent dye content originally contained in the solution.
In the crude high molecular polymer, the purity of the high molecular polymer is 75-85%, preferably 80%; in the crude fluorescent dye, the purity of the fluorescent dye is 85-95%, and preferably 90%.
Advantageous effects
1. The fluorescent anti-counterfeiting material prepared by the invention has the advantages of small particle size of 100nm, uniform particle size, convenience for filling in a printer for ink-jet printing and difficulty in causing nozzle blockage. The particle size distribution is shown in FIG. 1, and the transmission electron micrograph is shown in FIG. 2.
2. The fluorescent anti-counterfeiting material prepared by the invention has strong anti-interference capability and good stability, and is firmly combined on the surface of paper due to a large number of hydrogen bonds formed by interaction between abundant hydrogen bond sites on the surface of a polymer and paper cellulose. The anti-counterfeiting effect is still kept well even after the mixture is boiled in boiling water for 2 hours. Meanwhile, the anti-counterfeiting material has small particle size, so that the friction resistance of the anti-counterfeiting material is enhanced, and a stability test is shown in figure 3.
3. The fluorescent anti-counterfeiting material obtained by the invention has high brightness and good encryption degree, and the fluorescence spectrum is shown in figure 4. An ultraviolet (such as 254nm) LED is used as a light source, the fluorescence information of the anti-counterfeiting material can be read by a fiber optic spectrometer, and the read fluorescence spectrum is used as a spectrum fingerprint (figure 5) to achieve double anti-counterfeiting.
4. The fluorescent anti-counterfeiting material obtained by the method is not easy to decipher, on one hand, the type, the quantity and the proportion of the dye can be configured according to personal needs; alternatively, some interferents may be added to the dye solution to interfere with the translator.
5. The poor solvent used in the invention can be water, and the aqueous solution does not cause corrosion to the printer and has low toxicity.
6. The preparation process is simple, the experimental operation is simple and convenient, and expensive and complex equipment is not needed for production.
Drawings
FIG. 1 is a particle size distribution diagram of the anti-counterfeiting material prepared in example 1, wherein three measurement results are about 100 nm;
FIG. 2 is a TEM image of the particles of the anti-counterfeiting material prepared in example 1;
FIG. 3 is a stability test of a printing sample paper of the anti-counterfeiting material prepared in example 1, which is boiled in boiling water for 2 hours and the eraser is used for 100 times;
FIG. 4 is a fluorescence spectrum of the anti-counterfeiting material prepared in example 1;
FIG. 5 is a spectral fingerprint of the anti-counterfeiting material prepared in example 1;
FIG. 6 is a mass spectrum of the anti-counterfeiting material prepared in example 4.
Detailed Description
The following further describes the specific embodiments of the present invention with reference to the drawings and technical solutions.
A method for preparing a fluorescent anti-counterfeiting material with easy preparation, high encryption degree and ultra-stability comprises the following steps:
example 1
1. Weighing 0.01g of LR305 dye, and dissolving in 35.0mL of acetonitrile to form a uniform solution;
2. weighing 0.05g of polylactic acid polymer, dissolving in 10.0mL of acetonitrile, and stirring at 95 ℃ for 2h to form a uniform solution;
3. taking 0.8mL of polylactic acid solution, then adding 0.2mL of LR305 dye solution, stirring for 10 minutes, and mixing the solution for later use;
4. and adding the obtained mixed solution into 10mL of water to prepare the single-dye fluorescent anti-counterfeiting material.
Example 2
1. Weighing 0.0066g of 9, 10-diphenylanthracene dye, dissolving in 10.0mL of acetonitrile, and stirring at 85 ℃ for 2h to form a uniform solution;
2. weighing 0.05g of polylactic acid polymer, dissolving in 10.0mL of acetonitrile, and stirring at 95 ℃ for 2h to form a uniform solution;
3. taking 0.5mL of polylactic acid solution, then adding 0.5mL of 9, 10-diphenyl anthracene dye solution, stirring for 10 minutes, and mixing the solution for later use;
4. and adding the obtained mixed solution into 10mL of water to prepare the single-dye fluorescent anti-counterfeiting material.
Example 3
1. Weighing 0.0066g of 9, 10-diphenylanthracene dye, dissolving in 10.0mL of acetonitrile, and stirring at 85 ℃ for 2h to form a uniform solution; weighing 0.0025g of coumarin-6 dye, and dissolving in 250.0mL of acetonitrile;
2. weighing 0.05g of polylactic acid polymer, dissolving in 10.0mL of acetonitrile, and stirring at 95 ℃ for 2h to form a uniform solution;
3. taking 0.5mL of polylactic acid solution, then adding 0.45mL of 9, 10-diphenylanthracene dye solution and 0.05mL of coumarin-6 dye solution, stirring for 10 minutes, and mixing the solution for later use;
4. and adding the obtained mixed solution into 10mL of water to obtain the multi-dye fluorescent anti-counterfeiting material.
Example 4
1. Weighing 0.01g of LR305 dye, and dissolving in 35.0mL of acetonitrile to form a uniform solution;
2. weighing 0.05g of polylactic acid polymer, dissolving in 10.0mL of acetonitrile, and stirring at 95 ℃ for 2h to form a uniform solution;
3. taking 0.8mL of polylactic acid solution, then adding 0.2mL of LR305 dye solution, and stirring for 10 minutes;
4. 0.001g of crude polylactic acid was added to the mixed solution in 3, and stirred at 95 ℃ for 2 hours to form a uniformly mixed solution for further use.
5. And adding the obtained mixed solution into 10mL of water to prepare the single-dye fluorescent anti-counterfeiting material.
6. The obtained anti-counterfeit particles were centrifuged and then stirred at 95 ℃ for 2h to dissolve them in acetonitrile. The solution was subjected to mass spectrometry (FIG. 6), and the specific dye components could not be easily determined from the mass spectrometry results.
Claims (9)
1. A preparation method of a fluorescent anti-counterfeiting material is characterized by comprising the following steps:
(1) preparing a solution of one or more fluorescent materials;
(2) preparing a solution of a high molecular polymer;
(3) mixing the prepared high molecular polymer solution and the prepared fluorescent dye solution, and uniformly stirring to obtain a uniform solution for later use;
(4) preparing a poor solvent for the high molecular polymer;
(5) and (4) mixing the uniform solution obtained in the step (3) with the poor solvent prepared in the step (4), so that the fluorescent dye can be encapsulated by the polymer particles, and the fluorescent anti-counterfeiting material is obtained.
2. The production method according to claim 1, wherein in the step (3), the stirring time is 10 to 50 minutes.
3. The production method according to claim 1, wherein in the step (5), the mixing is direct mixing or mixing using a mixer.
4. The method of claim 1, wherein the fluorescent material comprises LR305, Fluorescein, rhodamine series dyes, Long Pepper, perylene, DPA, Coumarin series dyes, FITC, Calcein, 5-Carboxy fluorscein, BODIPY series dyes, Alexa TM 546, Pyronin Y, Thiadiacarbyanine, Alexa TM 594, 6-Aminofluorscein, Dansyl Chloride, 4-Methylolliferone, Aminoecomarin, Anthrocystearate, APC-Cy7, Atabrine, Aurophosphine, Bisbenzazepine, Catecholamine, Comarin Phalloidin, Dansyl Amorine, Danscholoy, Hydroxysmarin, HydroD, PerCP, Nile, rare, yellow, Melothrix, and synthetic dyes of the fluorescent series and the fluorescent dyes of Alexanox-5.
5. The method of claim 1, wherein the high molecular weight polymer comprises one or more of PLA, PLGA, PCL, P4VP, P2VP, PS, PVDF, PVDC, PP, PVF, PVFM, PVP, PVK, PVC, PVCA, PVCC, PVAC, PVAL, PTFE, PUR, PSU, PPA, PPE, PPO, PPS, POM, PMS, PMMA, PMP, PMCA, PISU, PIB, PI, PFF, PFA, PF, PET, PEO, PES, PETG, PEEK, PEBA, PE, PDAP, PDMS, PC, PCTFE, PBS, PBT, PBA, PBAN, PAT, PAUR, PAT, PASU, PAN, PAK, PAI, PAE, PA, PAA, PADC, MC, ABA, AES CA, CAB, CAP, CF, CMC, and artificially synthesized polymers.
6. The production method according to claim 1,
in the step (1), one or more fluorescent materials are dissolved in a good solvent of fluorescent dye and stirred to obtain a solution of one or more fluorescent materials; wherein the good solvent of the fluorescent dye is one or more of acetonitrile, methanol, ethanol, acetone, DMF and THF; the mass fraction of the fluorescent dye is 0.0001-80 wt%, the stirring temperature is 30-180 ℃, and the stirring time is 10-500 min;
in the step (2), dissolving a high molecular polymer in the good solvent of the high molecular polymer, and stirring to obtain a solution of the high molecular polymer; wherein the good solvent of the high molecular polymer is one or more of acetonitrile, methanol, ethanol, acetone, DMF and THF, and the concentration of the high molecular polymer is 0.001-180 mg mL-1Stirring at 30-180 ℃ for 10-500 min;
in the step (3), the mass ratio of the high molecular polymer to the fluorescent dye in the uniform solution is 0.00001-100000;
in the step (4), the poor solvent is water;
in the step (5), the volume ratio of the uniform solution to the poor solvent is 0.0001-100.
7. The production method according to claim 6,
in the step (1), the mass fraction of the fluorescent dye is 0.001-20 wt%;
in the step (2), the concentration of the high molecular polymer is 0.01-80 mg mL-1；
In the step (3), the mass ratio of the high molecular polymer to the fluorescent dye in the uniform solution is 0.001-1000;
in the step (5), the volume ratio of the uniform solution to the poor solvent is 0.001-100.
8. The method of manufacturing according to claim 1, further comprising the steps of: adding water-insoluble interferents in the step (3), heating at 40-180 ℃, and stirring for 5-500 min to completely dissolve the interferents.
9. The method of claim 8, wherein the interfering substance is a crude high molecular polymer and a crude fluorescent dye; in the crude high molecular polymer, the purity of the high molecular polymer is 75-85%; in the crude fluorescent dye, the purity of the fluorescent dye is 85-95%.
The addition amount of the interferent is 0.01-60 wt% of the content of the high molecular polymer and the fluorescent dye originally contained in the uniform solution.
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| CN202110164831.2A CN112745832A (en) | 2021-02-05 | 2021-02-05 | Method for preparing fluorescent anti-counterfeiting material |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101311807A (en) * | 2007-05-25 | 2008-11-26 | 施乐公司 | Core-shell particles containing fluorescent components for electrophoretic displays |
| CN104031477A (en) * | 2014-06-25 | 2014-09-10 | 吉林大学 | Panchromatic fluorescent anti-counterfeiting ink based on conjugated polymer nano-particles |
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2021
- 2021-02-05 CN CN202110164831.2A patent/CN112745832A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101311807A (en) * | 2007-05-25 | 2008-11-26 | 施乐公司 | Core-shell particles containing fluorescent components for electrophoretic displays |
| CN104031477A (en) * | 2014-06-25 | 2014-09-10 | 吉林大学 | Panchromatic fluorescent anti-counterfeiting ink based on conjugated polymer nano-particles |
Non-Patent Citations (1)
| Title |
|---|
| AUDREY MINOST等: "Nanoparticles via Nanoprecipitation Process", 《RECENT PATENTS ON DRUG DELIVERY & FORMULATION》 * |
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