Anti-counterfeiting application of digitally coded macromolecules in inks

Abstract

The application relates to the field of high polymer synthesis, in particular to a digital coding macromolecule in the anti-counterfeiting application of ink. The application provides a compound with a general formula I. The digital coding macromolecule of the application introduces a rigid structure triphenylmethyl at the end of a molecular chain, introduces different tag label information in the macromolecule, expands the information carrying capacity of the same binary coding macromolecule, and applies the macromolecule to ink, so that the function of anti-counterfeiting identification is realized.

Description

Technical Field

[0001] This application relates to the field of polymer synthesis, and in particular to the anti-counterfeiting application of a digitally encoded macromolecule in ink. Background Technology

[0002] Digitally encoded macromolecules are polymers synthesized using chemical methods, possessing precise sequence control similar to DNA and RNA molecules. They can be applied in cutting-edge fields such as information storage, catalysis, and drug development. By defining different chemical structures within these macromolecules as specific numbers, the molecules acquire the ability to store information. When used as markers in inks, they exhibit good stability and high concealment. Furthermore, polymer detection techniques such as mass spectrometry can decode the information carried within the ink layer, achieving anti-counterfeiting purposes.

[0003] Patent 201811244384.6 discloses a sequence polymer with anti-counterfeiting identification function, its preparation method, and its application. In this patent, the sequence polymer is mixed with a basic pigment according to a formula to prepare a "gene pigment." The authenticity of the gene pigment can be identified by performing macromolecular mass spectrometry testing through dissolution, extraction, and concentration. However, this sequence polymer has a low storage density per unit volume, and the information carried by the same macromolecule is relatively low. Summary of the Invention

[0004] In view of the shortcomings of the prior art described above, and to address the problems of low storage density and low information storage capacity of polymers in the prior art, making their application in ink anti-counterfeiting relatively easy, this application aims to provide an anti-counterfeiting application of digitally encoded macromolecules in inks to solve the problems in the prior art. This application introduces a rigid triphenylmethyl structure at the end of the molecular chain to further improve the thermal stability of the macromolecule; and introduces different tag information into the macromolecule to expand the information carrying capacity of the same binary encoded macromolecule; thereby increasing the storage density per unit volume; and applies this macromolecule to inks to achieve the function of anti-counterfeiting identification.

[0005] To achieve the above and other related objectives, the first aspect of this application provides a compound having the following general formula:

[0006]

[0007] Wherein, R1 is selected from or R3 is selected from substituted or unsubstituted thiols;

[0008] R2 is selected from bromine or

[0009] L is selected from octadecyl or hexyl.

[0010] The second aspect of this application provides a method for preparing the aforementioned compound, comprising the following steps:

[0011] 1) Reacting Dimer-L, trifluoroacetic acid, and triethylsilane yields Dimer-L-SH:

[0012]

[0013] 2) Dimer-L is heated in toluene to obtain Dimer-L-FU:

[0014]

[0015] 3) Under the action of triethylamine, Dimer-L-FU reacts with Dimer-L-SH to give 4mer-LXL:

[0016]

[0017] 4) Under the action of triethylamine, 4mer-LXL reacts with LH to obtain formula I:

[0018]

[0019] The third aspect of this application provides the use of the aforementioned compounds in the preparation of anti-counterfeiting ink products.

[0020] Compared with the prior art, the beneficial effects of this application are as follows:

[0021] 1. The digitally encoded macromolecule synthesized in this application uses triphenylmethyl-protected thiol groups at the ends and selects more stable side groups, which makes the whole molecule have better thermal stability.

[0022] 2. This application introduces different tags into macromolecules, which further improves information storage capacity.

[0023] 3. This application applies digitally encoded macromolecules to ink, which greatly increases the difficulty of obtaining anti-counterfeiting materials compared with existing anti-counterfeiting inks, making counterfeiting extremely difficult and highly concealed. Attached Figure Description

[0024] Figure 1 Displayed as the 1H NMR spectrum of digital polymer 101.

[0025] Figure 2 The image shown is a MALDI-TOF first-order mass spectrum of digital polymer 101 and a magnified view of a portion thereof.

[0026] Figure 3 The image shown is a MALDI-TOF primary mass spectrum of digital polymer B-101 and a magnified view of a portion thereof.

[0027] Figure 4 The image shown is a mass spectrum of digital polymer 101 extracted from ink, in which... Figure 4 A shows the first-order mass spectrum of digital polymer 101 and the structural assignments of the corresponding peaks. Figure 4 B shows the secondary mass spectrum of digital polymer 101 and the structural assignments of the corresponding peaks.

[0028] Figure 5 The image shows digital information analysis of digital polymer blend systems with "tags". The upper part of the image shows the first-order mass spectrum and the structure assignment of the corresponding peaks, while the lower part shows the second-order mass spectrum and the structure assignment of the corresponding peaks. Detailed Implementation

[0029] To make the inventive objectives, technical solutions, and beneficial effects of this application clearer, the following description, in conjunction with embodiments, further illustrates this application. It should be understood that the embodiments described are for illustrative purposes only and are not intended to limit the scope of the application. Unless otherwise specified, the experimental methods used in the following embodiments are conventional methods, and those skilled in the art can easily understand other advantages and effects of this application from the content disclosed in this description.

[0030] The inventors of this application, through extensive research and exploration, discovered the anti-counterfeiting application of a digitally encoded macromolecule in ink, and based on this discovery, completed this application. This application introduces a rigid triphenylmethyl structure at the end of the molecular chain to further enhance the thermal stability of the macromolecule; it also introduces different tag information into the macromolecule to expand the information carrying capacity of the same binary-coded macromolecule; it increases the storage density per unit volume; and it applies this macromolecule to ink to achieve anti-counterfeiting identification functions.

[0031] Generally, the nomenclature used herein (e.g., IUPAC nomenclature) and the laboratory procedures described below (including those for cell culture, organic chemistry, analytical chemistry, and pharmacology) are those well-known and commonly used in the art. Unless otherwise defined, all scientific and technical terms used herein in conjunction with the descriptions herein have the same meaning as commonly understood by those skilled in the art.

[0032] This application provides a compound having the following general formula:

[0033]

[0034] Wherein, R1 is selected from or R3 is selected from substituted or unsubstituted thiols;

[0035] R2 is selected from bromine or

[0036] L is selected from octadecyl or hexyl.

[0037] In this paper, the broken bonds indicated by the wavy lines show the connection points between the plotted groups and other parts of the molecule.

[0038] In the compounds provided in this application, R3 is selected from...

[0039] In the compounds provided in this application, R1 is selected from... R2 is selected from When L is selected from octadecyl or hexyl, the compound is of formula II:

[0040]

[0041] In the compounds provided in this application, when R1 is selected from... When R2 is selected from Br and L is selected from octadecyl or hexyl, the compound is of formula III:

[0042]

[0043] Formulas II and III provided in this application are digitally encoded macromolecules. The digitally encoded macromolecule shown in Formula II uses a triphenylmethyl-protected thiol group at the end and selects a more stable side group, giving the entire molecule better thermal stability. The digitally encoded macromolecule shown in Formula III introduces different tag labels (R3), further improving the information storage capacity.

[0044] The coding information of digitally encoded macromolecules includes the type and order of the numbers. Artificially, octadecyl groups are defined as "1", and hexyl groups are defined as "0". When R3 is selected from... When R3 is selected, the label information is defined as the letter A; when R3 is selected from... When R3 is selected, the label information is defined as the letter B; when R3 is selected from... At that time, the label information is defined as the letter C.

[0045] In the embodiments of this application, the information on the synthesized compounds is shown in Table 1:

[0046] Table 1 Summary of Synthesized Compounds

[0047]

[0048]

[0049]

[0050] Two or more three-digit polymers with introduced tags are added to the ink, and the polymer with tag-A is read in a pre-defined order, followed by those with tags-B and-C. This expands the information that can be read from the pigment. In a specific embodiment of this application, three coded polymers with different tags (A-111, B-101, and C-011, each 3 bits) in the mixture are read in a pre-defined order, for example, from A to C. This yields a "unique" information, 111101011 (9 bits). The tag order constitutes a second layer of anti-counterfeiting. Different tag reading orders result in different information, avoiding a larger synthesis workload. Simultaneously, it gives the anti-counterfeiting ink a larger information storage capacity (extending from 3 bits to 6 or 9 bits), and the reading order of the "reading sequence tag" provides another layer of encryption, thereby increasing the decryption difficulty and enhancing the security of the anti-counterfeiting ink.

[0051] Other compounds that can be deduced from Formula I within the scope of this application are all within the protection scope of this application.

[0052] This application also provides a method for preparing the aforementioned compound, comprising the following steps:

[0053] 1) Reacting Dimer-L, trifluoroacetic acid, and triethylsilane yields Dimer-L-SH:

[0054]

[0055] 2) Dimer-L is reacted with toluene by heating to obtain Dimer-L-FU:

[0056]

[0057] 3) Under the action of triethylamine, Dimer-L-FU reacts with Dimer-L-SH to give 4mer-LXL:

[0058]

[0059] 4) Under the action of triethylamine, 4mer-LXL reacts with LH to obtain formula I:

[0060]

[0061] In the preparation method provided in this application, step 1) refers to reacting Dimer-L, trifluoroacetic acid, and triethylsilane to obtain Dimer-L-SH:

[0062]

[0063] Dimer-L is dissolved in dichloromethane. After stirring until fully dissolved, trifluoroacetic acid is slowly added, and the solution changes from yellow to dark red. Then, triethylsilane is added, and the solution turns pale yellow again. The reaction is carried out at 25°C for 0.5 hours to obtain Dimer-L-SH.

[0064] The preparation process of Dimer-L is as follows:

[0065] Maleimide was dissolved in carbon tetrachloride, and liquid bromine was added dropwise under a nitrogen atmosphere at room temperature. The system was heated to 78°C and refluxed, then cooled to 25°C and stirred overnight to obtain crude product M-1.

[0066]

[0067] M-1 was dissolved in anhydrous tetrahydrofuran and stirred for 10 min under argon protection. The system was then cooled to 0°C. Triethylamine solution (dissolved in anhydrous tetrahydrofuran) was added dropwise to the system. After the addition was complete, the system was kept at 0°C and stirred for another 15 min. The temperature was then raised to 25°C and stirred for 2 h to obtain crude M-2.

[0068]

[0069] M-2, furan, and anhydrous diethyl ether were sealed and reacted at 78°C for 96 hours to obtain M-3.

[0070]

[0071] 1,8-Dibromooctane and anhydrous potassium carbonate were dissolved in N,N-dimethylformamide (DMF) under argon protection and stirred for 10 min. M-3 DMF solution was added dropwise to the system, and the reaction was carried out at 25 °C for 12 h to obtain pure FPBM-C8-Br.

[0072]

[0073] FPBM-C8-Br was dissolved in DMF, and triphenylmethanethiol and anhydrous potassium carbonate were added. The system was reacted at 25°C for 12 h to obtain pure Monomer.

[0074]

[0075] Monomer was dissolved in dichloromethane. The system was stirred for 10 minutes to ensure complete dissolution. Trifluoroacetic acid was slowly added to the system, and the solution changed from yellow to dark red. Then, triethylsilane was added, and the solution turned pale yellow again. The reaction was carried out at 25°C for half an hour to obtain crude Monomer-SH.

[0076] Monomer was dissolved in toluene, and the system was heated to 110°C and reacted for 12 hours to obtain crude Monomer-FU.

[0077] Monomer-FU was dissolved in chloroform and stirred until fully dissolved. Triethylamine was then added, and the mixture was stirred for 5 minutes under argon protection. Subsequently, 250 mL of a Monomer-SH solution in chloroform was added dropwise, and the reaction was carried out at 25°C for 12 hours to obtain Dimer-X.

[0078]

[0079] When L is selected from octadecyl, L is defined as 1. The preparation process of Dimer-1 is as follows: Dimer-X is dissolved in chloroform under argon protection. Triethylamine and octadecyl mercaptan are then added dropwise, and the system is maintained at 25°C for 12 hours to obtain Dimer-1.

[0080]

[0081] When L is chosen as its own alkyl group, L is defined as 0. The preparation process of Dimer-0 is as follows: Dimer-X is dissolved in chloroform under argon protection. Triethylamine and hexamethylenetetramine are then added dropwise, and the system is maintained at 25°C for 12 hours to obtain Dimer-0.

[0082]

[0083] In the preparation method provided in this application, step 2) refers to heating Dimer-L in toluene to obtain Dimer-L-FU:

[0084]

[0085] In some embodiments, the reaction temperature is 110°C and the reaction time is 12 hours.

[0086] In the preparation method provided in this application, step 3) refers to the reaction of Dimer-L-FU and Dimer-L-SH under the action of triethylamine to obtain 4mer-LXL:

[0087]

[0088] In some embodiments, Dimer-1-FU is dissolved in chloroform, triethylamine is added, and the mixture is stirred for 5 minutes under argon protection. Subsequently, a chloroform solution of Dimer-1-SH obtained in step 1) is added dropwise, and the system is reacted at 25°C for 12 hours to obtain 4mer-1-X-1.

[0089] In the preparation method provided in this application, step 4) refers to reacting 4mer-LXL, triethylamine, and LH to obtain formula I:

[0090]

[0091] In some embodiments, the reaction temperature is 25°C and the reaction time is 12 hours.

[0092] In the preparation method provided in this application, when R1 is selected from... R2 is selected from When L is selected from octadecyl or hexyl, step 4) yields formula II.

[0093] In the preparation method provided in this application, when R1 is selected from... When R2 is selected from Br and L is selected from octadecyl or hexyl, step 4) yields Formula III. Formula III is obtained by introducing the R3 group into the terminal succinimide skeleton of Formula II through a retro-Diels-Alder reaction and a base-catalyzed condensation reaction.

[0094] The digitally encoded macromolecular formulas II and III of this application were obtained through the aforementioned preparation method.

[0095] This application also provides the application of the aforementioned compound in the preparation of anti-counterfeiting ink products.

[0096] In the applications provided in this application, the inks include one or more combinations of engraving gravure inks, photogravure inks, offset inks, screen printing inks, and varnishes. This application applies digitally coded macromolecules to the inks, significantly increasing the difficulty of obtaining anti-counterfeiting materials and making counterfeiting extremely difficult and highly concealed compared to existing anti-counterfeiting inks. In practical applications, coded macromolecules with labels are added to the inks at a certain proportion, for example, 0.1%-10%. After printing, the information contained in the printed product is extracted through methods such as dissolution and extraction. Further testing using mass spectrometry to extract the digital coded information allows for the determination of the authenticity of the printed product.

[0097] The present application will be further illustrated by the following examples, but these examples do not limit the scope of the present application.

[0098] Example 1

[0099] Synthesis of digitally encoded macromolecule 101

[0100] In a dry, three-necked round-bottom flask equipped with a condenser and a constant-pressure dropping funnel, maleimide was added and dissolved in carbon tetrachloride. Bromine was then added dropwise under a nitrogen atmosphere at room temperature. The system was heated to 78°C and refluxed, then cooled to 25°C and stirred overnight. Crude product M-1 was obtained.

[0101]

[0102] In a round-bottom flask equipped with a constant-pressure dropping funnel, add M-1 dissolved in anhydrous tetrahydrofuran, stir for 10 min, and cool the system to 0°C under argon protection. Add triethylamine solution (dissolved in anhydrous tetrahydrofuran) dropwise to the system. After the addition is complete, maintain the temperature at 0°C and stir for another 15 min. Warm the system to 25°C and stir for 2 h. Thin-layer chromatography shows the reaction is complete, yielding crude M-2.

[0103]

[0104] In a dry, thick-walled pressure-resistant tube, M-2, furan, and anhydrous diethyl ether were added sequentially. The tube was sealed, and the system was reacted at 78°C for 96 hours to obtain M-3.

[0105]

[0106] In a dry round-bottom flask equipped with a constant-pressure dropping funnel, 1,8-dibromooctane and anhydrous potassium carbonate were added and dissolved in N,N-dimethylformamide (DMF). The mixture was stirred for 10 min under argon protection. M-3 DMF solution was then added dropwise, and the reaction was carried out at 25°C for 12 h to obtain pure FPBM-C8-Br.

[0107]

[0108] FPBM-C8-Br was added to a dry round-bottom flask and dissolved in DMF. Triphenylmethanethiol and anhydrous potassium carbonate were then added, and the system was reacted at 25°C for 12 hours to obtain pure Monomer.

[0109]

[0110] In a dry round-bottom flask, Monomer was added and dissolved in dichloromethane. The system was stirred for 10 minutes to ensure complete dissolution. Trifluoroacetic acid was slowly added to the system, and the solution changed from yellow to dark red. Then, triethylsilane was added, and the solution turned pale yellow again. The reaction was allowed to proceed for half an hour, and thin-layer chromatography showed that the reaction was complete. The crude Monomer-SH product was obtained.

[0111] In a dry 1.0L round-bottom flask, Monomer was added and dissolved in toluene. The system was heated to 110°C and reacted for 12 hours to obtain crude Monomer-FU.

[0112] In a dry round-bottom flask equipped with a constant-pressure dropping funnel, Monomer-FU was added, followed by chloroform, and stirred until fully dissolved. Triethylamine was then added, and the mixture was stirred for 5 minutes under argon protection. Subsequently, 250 mL of a Monomer-SH solution in chloroform was added dropwise, and the reaction was carried out at 25°C for 12 hours. Dimer-X was obtained.

[0113]

[0114] In a dry 1.0 L round-bottom flask, Dimer-X was added and dissolved in chloroform under argon protection. Triethylamine and octadecyl mercaptan were then added dropwise, and the reaction was maintained at 25 °C for 12 h. This yielded Dimer-1 (the compound shown in Formula I).

[0115]

[0116] In a dry 1.0 L round-bottom flask, Dimer-X was added and dissolved in chloroform under argon protection. Triethylamine and hexamethylenetetramine were then added dropwise, and the reaction was maintained at 25 °C for 12 h. This yielded Dimer-0 (the compound shown in Formula I).

[0117]

[0118] In a dry 1.0 L round-bottom flask, Dimer-1 was added and dissolved in dichloromethane. The system was stirred for 10 min to ensure complete dissolution. Trifluoroacetic acid was slowly added to the system, and the solution changed from yellow to dark red. Then, triethylsilane was added, and the solution turned pale yellow again. The reaction was continued for 0.5 h to obtain crude Dimer-1-SH.

[0119] In a dry 1.0 L round-bottom flask, Dimer-1 was added and dissolved in toluene. The system was heated to 110 °C and reacted for 12 h. Thin-layer chromatography showed that the reaction was complete, yielding crude Dimer-1-FU.

[0120] In a dry 1.0 L round-bottom flask equipped with a constant-pressure dropping funnel, Dimer-1-FU was added, followed by chloroform, and the mixture was stirred until fully dissolved. Triethylamine was then added, and the mixture was stirred for 5 min under argon protection. Subsequently, a chloroform solution of Dimer-1-SH was added dropwise, and the system was reacted at 25 °C for 12 h to obtain 4mer-1-X-1.

[0121]

[0122] In a dry 500 mL round-bottom flask, 4mer-1-X-1 was added and dissolved in chloroform under argon protection. Triethylamine and hexamethylenetetramine were then added dropwise, and the reaction was maintained at 25 °C for 12 h to obtain digital polymer 101 (Formula II).

[0123]

[0124] The proton NMR spectrum and MALDI-TOF primary mass spectrum are shown below. Figures 1-2 As shown.

[0125] Example 2

[0126] Synthesis of digitally encoded macromolecule B-101

[0127] Synthesis and characterization of pre-sequence

[0128] In a dry round-bottom flask, the Monomer prepared in Example 1 was added and dissolved in dichloromethane. The system was stirred for 10 min to ensure complete dissolution. Trifluoroacetic acid was slowly added to the system, and the solution changed from yellow to dark red. Then, triethylsilane was added, and the solution turned pale yellow again. The reaction was allowed to proceed for half an hour, and thin-layer chromatography showed that the reaction was complete. Crude Monomer-SH was obtained.

[0129] In a dry 1.0 L round-bottom flask, FPBM-C8-Br was added and dissolved in toluene. The system was heated to 110 °C and reacted for 12 h. The toluene was evaporated to dryness to obtain crude BM-Br.

[0130] In a dry 2.0L round-bottom flask equipped with a constant-pressure dropping funnel, BM-Br was added, followed by chloroform, and the mixture was stirred to dissolve. Triethylamine was then added, followed by 500mL of a Monomer-SH chloroform solution. The system was reacted at 25°C for 12 hours.

[0131] Dimer-X-Br was obtained.

[0132]

[0133] In a dry 1.0 L round-bottom flask, Dimer-X-Br was added and dissolved in chloroform under argon protection. Triethylamine and octadecyl mercaptan were then added dropwise, and the reaction was maintained at 25 °C for 12 h to obtain Dimer-1-Br.

[0134]

[0135] In a dry 1.0 L round-bottom flask, Dimer-1 was added and dissolved in dichloromethane. The system was stirred for 10 min to ensure complete dissolution. Trifluoroacetic acid was slowly added to the system, and the solution changed from yellow to dark red. Then, triethylsilane was added, and the solution turned pale yellow again. The reaction was continued for 0.5 h to obtain crude Dimer-1-SH.

[0136] In a dry 1.0 L round-bottom flask, Dimer-1-Br was added and dissolved in toluene. The system was heated to 110 °C and reacted for 12 h. The toluene was then evaporated to dryness to obtain Dimer-1-Br-FU.

[0137] In a dry 1.0 L round-bottom flask equipped with a constant-pressure dropping funnel, Dimer-1-Br-FU was added, followed by chloroform, and the mixture was stirred until fully dissolved. Triethylamine was then added, and the mixture was stirred for 5 min under argon protection. Subsequently, 200 mL of a chloroform solution of Dimer-1-SH was added dropwise, and the system was reacted at 25 °C for 12 h to yield 4mer-1-X-1-Br.

[0138]

[0139] In a dry 500 mL round-bottom flask, 4mer-1-X-1-Br was added and dissolved in 100 mL of chloroform. Triethylamine and hexamethylenetetramine were then added dropwise, and the reaction was maintained at 25 °C for 12 h. Thin-layer chromatography showed that the reaction was complete. After concentration, the residue was purified by column chromatography to obtain the digital polymer 4mer(1-0-1)-Br.

[0140]

[0141] In a dry 500 mL round-bottom flask, 4mer-1-X-1-Br was added and dissolved in 300 mL toluene. The system was heated to 110 °C and reacted for 24 h. The toluene was evaporated to dryness to give 101-Br-FU.

[0142] In a dry 200 mL round-bottom flask, 101-Br-FU was added and dissolved in 100 mL of chloroform. Triethylamine and decanethiol were then added dropwise, and the system was kept at 25 °C for 20 min to obtain B-101.

[0143]

[0144] The MALDI-TOF primary mass spectrum of digital polymer B-101 and its magnified portion are shown below. Figure 3 As shown.

[0145] Example 3

[0146] This embodiment provides an anti-counterfeiting application method for digitally coded macromolecules in ink. 30 mg of the digitally coded macromolecule containing the information "101" prepared in Example 1 was added to 3 g of engraved gravure ink. The mixture was centrifuged at 2500 rpm for 10 minutes until homogeneous. A printed sample containing the digitally coded information was obtained using a printing adaptor and allowed to air dry for 24 hours. 5 mg of solid ink layer was removed using a doctor blade. This ink layer was dissolved and extracted with 100 μL of anhydrous ethanol. After filtration, mass spectrometry analysis was performed, and the results are as follows: Figure 4 As shown.

[0147] Extracts of digital polymer 101 were sequenced using macromolecular mass spectrometry, yielding the following conclusions: Primary mass spectrometry clearly identified the molecular ion peak of digital polymer 101 ([101-Furan+Na)). + =1992.50 Da), and the experimental value is consistent with the theoretical value. The secondary mass spectrometry shows two clear fracture paths, and the corresponding fracture fragments can be assigned. Thus, the digital information 1-0-1 can be clearly read.

[0148] In summary, it is possible to embed, extract, and read stored information of digital polymer 101 in ink, thus serving as a molecular anti-counterfeiting label.

[0149] Example 4

[0150] The preparation method of Example 2 was followed, except that octadecyl mercaptan could be replaced with hexamethylene mercaptan, and decyl mercaptan could be replaced with benzyl mercaptan or phenylethyl mercaptan, yielding digital polymers A-111, B-101, and C-011. Three 3-bit digital polymers (A-111, B-101, and C-011, each with a different "reading sequence label (A, B, C, A: benzyl, B: decyl, C: phenethyl)") were mixed to prepare an anti-counterfeiting ink containing all three digital polymers. A mixed extract of digital polymers A-111, B-101, and C-011 was obtained using the same extraction method as in Example 3.

[0151] Sequencing using macromolecular mass spectrometry, such as Figure 5 As shown, molecular ion peaks ([A-111+Na)) of the digital polymers A-111, B-101, and C-011 can be clearly found in the first-order mass spectrometry. + =2007.633Da,[B-101+Na] + =1889.585 Da and [C-011+Na] + =1853.542 Da). Simultaneously, clear fracture paths can be read from the secondary mass spectrometry of each tagged digital polymer. By artificially specifying the reading order, for example, reading sequentially from A to C, a "unique" information can be obtained, namely 111101011 (9 bits).

[0152] The above embodiments are merely illustrative of the principles and effects of the present invention and are not intended to limit this application. Any person skilled in the art can modify or alter the above embodiments without departing from the spirit and scope of this application. Therefore, all equivalent modifications or alterations made by those skilled in the art without departing from the spirit and technical concept disclosed in this invention should still be covered by the claims of this application.

Claims

1. A compound, characterized in that, having the general formula: wherein R1is selected from or ; R2is selected from bromo or ; L is selected from octadecyl or hexyl; R3is selected from , or .

2. The compound of claim 1, wherein said compound is selected from formula II: wherein L is selected from octadecyl or hexyl.

3. The compound of claim 1, wherein said compound is selected from formula III: wherein L is selected from octadecyl or hexyl, R3is selected from , or .

4. The compound of claim 1, wherein said compound is selected from: 、 、 、 、 、 、 、 or .

5. Use of a compound according to any one of claims 1 to 4 for the preparation of an ink security product.

6. Use according to claim 5, wherein the compound is ###0002### said ink comprises one or more of a combination of intaglio ink, gravure ink, flexographic ink, screen ink, gloss ink.

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