A compound and a polymer having dynamic functions formed therefrom

Abstract

The present invention provides a compound and a polymer with dynamic functions formed therefrom, wherein the compound is 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester. A new compound is provided in the present application, and a novel polymer with dynamic functions is formed by polymerizing the compound. The polymer material not only has good dynamic properties, but also can realize repeated processing and recycling, and has excellent mechanical properties, ductility and optical properties, and low preparation cost.

Description

Technical Field

[0001] The invention relates to the field of compounds, in particular to a compound and a polymer with dynamic functions formed from the compound. Background Art

[0002] Dynamic covalent bond is a reversible covalent bond. Different from traditional covalent bond, it can be reversibly formed and broken by slight stimulation from the environment. This dynamic characteristic and self-healing ability make it play an important role in the preparation of new functional materials.

[0003] Based on dynamic covalent bonds, simple molecules can be used to construct porous polymer networks. These materials have important potential application value in adsorption, separation or catalysis.

[0004] How to provide or construct a low-cost material with good self-repair and recycling effects to reduce dependence on non-renewable petrochemical resources has always been a technical effect explored and pursued by researchers in the field of materials. Summary of the invention

[0005] In view of the above-mentioned shortcomings of the prior art, the purpose of the present invention is to provide a small molecule and a polymer with dynamic functions formed therefrom, which has low preparation cost and excellent self-healing and recycling properties, and is used to solve the problem of dependence of materials in the field of new materials in the prior art on traditional resources such as petrochemical resources.

[0006] To achieve the above objectives and other related objectives, the present invention is achieved through the following technical solutions.

[0007] The present invention first provides a compound, which is 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester, and the structural formula is shown in Formula I:

[0008]

[0009] The present invention also provides a method for preparing the compound as described above, wherein 2,2′-(1,2-ethylenedioxy)bisethylthiol is contacted with diketene to obtain 2,2′-(1,2-ethylenedioxy)bisethylthioacetate, and the synthesis route is as follows:

[0010]

[0011] Preferably, the reaction is carried out in a first organic solvent. More preferably, the first organic solvent is dichloromethane.

[0012] Preferably, an acid binding agent is also used in the reaction. More preferably, the acid binding agent is triethylamine.

[0013] Preferably, after the reaction is completed, a post-treatment step is further included, wherein the post-treatment includes purification and heating. More preferably, purification is performed by a silica gel column, and the eluent is a mixture of n-hexane and ethyl acetate. More preferably, the heating is rotary evaporation. The eluent is removed by heating.

[0014] The present invention also provides a polymer with dynamic functions, wherein the polymer is a dynamic cross-linked network formed by reacting 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester with tris(2-aminoethyl)amine.

[0015] Preferably, the reaction temperature is 30-150°C.

[0016] Preferably, the reaction is carried out in a second organic solvent. The second organic solvent is acetonitrile.

[0017] Preferably, the molar ratio of the acetoacetate groups of bis(1,2-ethylenedioxy)acetoacetate to the primary amine groups of tris(2-aminoethyl)amine is less than 1. That is, the primary amine groups of tris(2-aminoethyl)amine are excessive during the reaction.

[0018] Only when the primary amine groups of tri(2-aminoethyl)amine are excessive can the dynamic cross-linked material be effectively reprocessed and recycled. If the primary amine group content of tri(2-aminoethyl)amine is too low, the dynamic cross-linked material will crack after reprocessing and the dynamic performance will be poor; if the tri(2-aminoethyl)amine content is too high, the cross-linking density of the dynamic cross-linked material will decrease, resulting in a significant reduction in mechanical properties and loss of use value.

[0019] More preferably, the molar ratio of the primary amine group of tris(2-aminoethyl)amine to the acetoacetate group of bis(2,2′-(1,2-ethylenedioxy)acetoacetate is greater than 1 and less than or equal to 2. For example, the molar ratio is 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9 or 2.0.

[0020] The present application provides a new compound, and a new type of polymer with dynamic functions is formed by polymerizing this compound. This polymer material not only has good dynamic properties and can be repeatedly processed and recycled, but also has excellent mechanical properties, ductility and optical properties, and has a low preparation cost. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figure 1 The H NMR spectrum of the product of Example 1, 2,2′-(1,2-ethylenedioxy)acetoacetate, diethylthioate.

[0022] Figure 2The mass spectrum of the product of Example 1, 2,2′-(1,2-ethylenedioxy)acetoacetate, is shown.

[0023] Figure 3 Shown is the H NMR spectrum of triethylene acetoacetate, the product in Comparative Example 1.

[0024] Figure 4 Shown is the mass spectrum of triethylene acetoacetate, the product in Comparative Example 1.

[0025] Figure 5 Shown is a diagram of the stress relaxation effect of the ethyleneamine thioester dynamic cross-linked network obtained in Example 2 and Comparative Example 2.

[0026] Figure 6 Shown is a diagram showing the tensile properties of the ethyleneamine thioester dynamic cross-linked network obtained in Example 2 and Comparative Example 2.

[0027] Figure 7 The figure shows the tensile properties of the ethyleneamine thioester dynamic cross-linked network obtained in Example 2 after repeated processing.

[0028] Figure 8 Shown is a schematic diagram of the recycling process of the ethyleneamine thioester dynamic cross-linked network obtained in Example 2 when undergoing a recycling performance test.

[0029] Fig. 9 Shown is the refractive index effect diagram of the ethyleneamine thioester dynamic cross-linked network obtained in Example 2 and Comparative Example 2.

[0030] Fig.10 Shown is the H NMR spectrum of n-butylthioacetoacetate prepared in a specific embodiment.

[0031] Fig.11 Shown is a dynamic exchange kinetic diagram of n-butylthioacetoacetate prepared in a specific embodiment.

[0032] Fig.12 Shown is the H NMR spectrum of n-butyl acetoacetate prepared in a specific embodiment.

[0033] Fig.13 Shown is a dynamic exchange kinetic diagram of n-butyl acetoacetate prepared in a specific embodiment. DETAILED DESCRIPTION

[0034] The following describes the embodiments of the present invention through specific examples, and those skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and the details in this specification can also be modified or changed in various ways based on different viewpoints and applications without departing from the spirit of the present invention.

[0035] Before further describing the specific embodiments of the present invention, it should be understood that the scope of protection of the present invention is not limited to the specific embodiments described below; it should also be understood that the terms used in the examples of the present invention are intended to describe specific embodiments, rather than to limit the scope of protection of the present invention. The test methods in the following examples without specifying specific conditions are generally carried out under conventional conditions or under conditions recommended by the manufacturers.

[0036] When the embodiments give numerical ranges, it should be understood that, unless otherwise specified in the present invention, both endpoints of each numerical range and any numerical value between the two endpoints can be selected. Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those generally understood by those skilled in the art. In addition to the specific methods, equipment, and materials used in the embodiments, according to the grasp of the prior art by those skilled in the art and the record of the present invention, any methods, equipment, and materials of the prior art similar or equivalent to the methods, equipment, and materials described in the embodiments of the present invention can also be used to realize the present invention.

[0037] Example 1

[0038] The synthesis of 2,2′-(1,2-ethylenedioxy)acetoacetate (EDT-AA) is as follows:

[0039]

[0040] The specific steps are as follows: 1) Take 5g (1eq.) 2,2′-(1,2-ethylenedioxy)diethanethiol (98%) and dissolve it in 50ml anhydrous dichloromethane; 2) Slowly add 5.13g diketone (1.1eq., 97%) to the above solution. 3) Stir the above solution at room temperature and drop 300ul triethylamine (99.0%). Continue to stir the above solution at room temperature for 12 hours.

[0041] Post-treatment step: purify the solution after the reaction through a silica gel column, wherein the eluent is n-hexane:ethyl acetate in a mass ratio of 1:1; remove the eluent by rotary evaporation to obtain pure 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester.

[0042] Figure 1 This is the H NMR spectrum of the product 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester in this example.

[0043] Figure 2 This is the mass spectrum of the product 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester in this example.

[0044] The calculated yield is 91.2%.

[0045] Comparative Example 1

[0046] This comparative example is the synthesis of triethylene glycol acetoacetate, and the synthetic route is as follows:

[0047]

[0048] Specifically, 5 g (1 eq.) of triethylene glycol (99%) was dissolved in 50 ml of anhydrous dichloromethane; 6.29 g of diketone (1.1 eq., 97%) was slowly added to the above solution; the above solution was stirred at room temperature, and 300 ul of triethylamine (99.0%) was dropped, and the above solution was continued to be stirred at room temperature for 12 hours.

[0049] Post-treatment: the solution after the reaction is purified by a silica gel column, the eluent is n-hexane:ethyl acetate in a mass ratio of 2:1; the eluent is removed by rotary evaporation to obtain pure triethylene glycol acetoacetate.

[0050] The yield was 96.5%.

[0051] Figure 3 This is the H NMR spectrum of the product triethylene glycol acetoacetate in this comparative example.

[0052] Figure 4 It is the mass spectrum of triethylene glycol acetoacetate, the product in this comparative example.

[0053] Example 2

[0054] This example is the preparation of a dynamic cross-linked network of vinylamine thioester.

[0055] The specific steps are as follows:

[0056] 2 g of 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester prepared in Example 1 was dissolved in a polytetrafluoroethylene beaker containing 15 ml of acetonitrile; 0.61 g (1.1 eq.) of tris(2-aminoethyl)amine (TREN) was slowly added while the above solution was stirred; after the addition was completed, the mixture was stirred at room temperature for 30 minutes; the mixed solution after stirring was placed in an oven at 80° C. for 6 hours to evaporate the solvent and solidify; the sample was placed in a vacuum oven at 70° C. overnight to continue solidification in order to remove small molecular water, etc.

[0057] The cured sample was taken out, cut into small pieces, placed on a flat-plate hot press, and hot-pressed at 120°C for 20 minutes with a pressure of 15 MPa to obtain a rectangular sample with a thickness of about 1 mm for subsequent performance characterization.

[0058] Comparative Example 2

[0059] Dissolve 2 g of triethylene acetoacetate prepared in Comparative Example 1 in a polytetrafluoroethylene beaker containing 15 ml of acetonitrile; slowly add 0.67 g (1.1 eq.) of tri(2-aminoethyl)amine while stirring the above solution; stir at room temperature for 30 minutes after the addition is completed; put the mixed solution after stirring evenly into an oven at 80°C for 6 hours to evaporate the solvent and solidify; continue to put the sample into a vacuum oven at 70°C overnight to continue solidification and remove small molecular water, etc.

[0060] The cured sample was taken out, cut into small pieces, placed on a flat-plate hot press, and hot-pressed at 120°C for 20 minutes with a pressure of 15 MPa to obtain a rectangular sample with a thickness of about 1 mm for subsequent performance characterization.

[0061] The performance test results of the vinylamine thioester dynamic crosslinking network obtained in Example 2 and the vinylamine ester dynamic crosslinking network of Comparative Example 2 are as follows.

[0062] Stress relaxation: The stress relaxation experiment was conducted on a DMA (TA Q800), and rectangular splines with a size of 1.0 mm (T) × 5.5 mm (W) × 15 mm (L) were cut and tested at 90°C to 110°C at intervals of 10°C. The relaxation modulus G(t) obtained from the test was normalized with the initial relaxation modulus G0 and plotted as a function of time.

[0063] Specific results such as Figure 5 As shown, Figure 5 is a normalized stress relaxation diagram, from which it can be seen that at the same temperature, the dynamic exchange rate of the ethyleneamine thioester dynamic crosslinking network obtained in Example 2 is much greater than that of the ethyleneamine ester dynamic crosslinking network in Comparative Example 2. The specific relaxation time corresponding to the temperature is shown in Table 1.

[0064] Table 1

[0065] Relaxation temperature(℃) Example 2 Corresponding relaxation time (s) Comparative Example 2 Corresponding relaxation time (s) 90 188.6 2195.0 100 122.7 997.7 110 81.6 694.5

[0066] Tensile properties: The tensile stress-strain curve of a dumbbell-shaped specimen of 1.0 mm (T) × 2 mm (W) × 35 mm (L) was tested on a universal testing machine (Instron 3343) at room temperature (25°C) with a uniaxial tensile rate of 5 mm / min. The test results are shown in Figure 6 As shown, the curve results show that the ductility of the dynamic crosslinked network of vinylamine thioester obtained in Example 2 is 1.4 times that of the dynamic crosslinked network of vinylamine ester in Comparative Example 2.

[0067] Repeated processing: Cut the sample into small pieces with a mass of less than 0.05g, place them in a rectangular metal mold (about 1.0mm (T) × 10mm (W) × 35mm (L)), and heat press them on a flat hot press for 15 minutes at 120℃ and 15MPa pressure. Repeat the above operation twice to measure the tensile properties and characterize the effect of repeated processing of the sample. Figure 7 As shown, the tensile properties of the embodiment after two repeated processing are consistent with those of the initial sample, proving that the embodiment can achieve good repeated processing.

[0068] Recycling: Cut 2g of the sample in the example into small pieces with a mass of less than 0.05g, place them in a flask filled with 150ml of anhydrous tetrahydrofuran, then add 1.6ml of 12M concentrated hydrochloric acid, stir at room temperature for 24 hours and filter. The filtrate is neutralized with saturated sodium bicarbonate, washed with saturated sodium chloride solution three times, and concentrated by rotary evaporation to obtain pure 2,2′-(1,2-ethylenedioxy)acetoacetic acid diethyl thioester in Example 1. Immerse the filter residue in 5ml of methanol, add 0.5g of potassium hydroxide, stir at 40°C for 12 hours and filter, and distill the filtrate under reduced pressure to recover pure cross-linking agent tri(2-aminoethyl)amine. The recovered 2,2′-(1,2-ethylenedioxy)acetoacetic acid diethyl thioester and tri(2-aminoethyl)amine are cross-linked again through the cross-linking process of Example 2 to form a new sample. The specific recovery process is as follows Figure 8 The thermomechanical properties show that the performance of the sample after recycling is consistent with that of the initial sample, proving that the embodiment can achieve good recycling.

[0069] Refractive index: The refractive index was measured using a high-throughput spectroscopic ellipsometer (M2000V, JA Woollam Co.). The data collection range was 370-1200 nm (1.5 nm step length) and the angles were 50°, 60°, and 70°. Fig. 9 It can be seen that the refractive index of the dynamic cross-linked network of vinylamine thioester obtained in Example 2 is greater than that of the dynamic cross-linked network of vinylamine ester in Comparative Example 2. In the present application, the applicant unexpectedly discovered and constructed a small molecule compound with a structural formula as shown in Formula I in the present application during continuous research and exploration, and found that when it is applied to form a polymer with dynamic functions, the polymer has good dynamic characteristics, can be repeatedly processed and recycled, and has excellent mechanical properties, ductility and optical properties, and has a low preparation cost.

[0070] Example 3

[0071] This Example 3 is to prepare a dynamic crosslinked network of vinylamine thioester by using a higher ratio of primary amine groups of tris(2-aminoethyl)amine to acetoacetate groups of 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester.

[0072] The specific steps are as follows:

[0073] 2 g of 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester prepared in Example 1 was dissolved in a polytetrafluoroethylene beaker containing 15 ml of acetonitrile; 0.83 g (1.5 eq.) of tris(2-aminoethyl)amine (TREN) was slowly added while the above solution was stirred; after the addition was completed, the mixture was stirred at room temperature for 30 minutes; the mixed solution after stirring was placed in an oven at 80° C. for 6 hours to evaporate the solvent and solidify; the sample was placed in a vacuum oven at 70° C. overnight to continue solidification to remove small molecular water, etc.

[0074] The cured sample was taken out, cut into small pieces, placed on a flat-plate hot press, and hot-pressed at 120°C for 20 minutes with a pressure of 15 MPa to obtain a rectangular sample with a thickness of about 1 mm for subsequent performance characterization.

[0075] The tensile properties of Example 3 were tested using a universal tensile machine at room temperature. The results showed that the strain of Example 3 was 1.1 times (194.0%) that of Example 2, but the Young's modulus decreased by 4.5 times (0.32MPa). The stress relaxation experiment showed that the characteristic relaxation time at 90°C was 140.7s, which was less than that of Example 2. This is because the increase in primary amine content accelerates the dynamic exchange reaction, but at the same time it also increases the defects (primary rings, pendant chains) in the cross-linked network, resulting in a decrease in cross-linking density and a decrease in mechanical properties.

[0076] Comparative Example 3

[0077] Comparative Example 3 is a method for preparing a dynamic crosslinked network of vinylamine thioester by using a lower ratio of primary amine groups of tris(2-aminoethyl)amine to acetoacetate groups of 2,2′-(1,2-ethylenedioxy)acetoacetate.

[0078] The specific steps are as follows:

[0079] 2 g of 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester prepared in Example 1 was dissolved in a polytetrafluoroethylene beaker containing 15 ml of acetonitrile; 0.50 g (0.9 eq.) of tris(2-aminoethyl)amine (TREN) was slowly added while the above solution was stirred; after the addition was completed, the mixture was stirred at room temperature for 30 minutes; the mixed solution after stirring was placed in an oven at 80° C. for 6 hours to evaporate the solvent and solidify; the sample was placed in a vacuum oven at 70° C. overnight to continue solidification to remove small molecular water, etc.

[0080] The cured sample was taken out, cut into small pieces, and placed on a flat hot press machine and hot pressed at 120°C for 20 minutes at a pressure of 15 MPa. However, a dense and uniform sheet was not obtained as in Example 2 and Example 3, and cracks appeared on the surface of the hot-pressed material. This is because the free amine content is low, and the dynamic exchange reaction in the cross-linked network is limited, resulting in poor processability.

[0081] In fact, the test results of Example 2 and Comparative Example 2 were also unexpected by the applicant, because the applicant actually first studied the dynamic characteristics of small molecules containing only -S- and found that their dynamic exchangeability was slower than that of small molecules containing -O-. The specific description is as follows.

[0082] (I) Synthesis and confirmation of n-butyl thioacetoacetate and n-butyl-ethyleneamine thioester

[0083] The applicant first synthesized n-butyl thioacetoacetate, the structural formula of which is The specific implementation is as follows:

[0084] 1) Dissolve 3 g (1 eq.) of n-butyl mercaptan (97%) in 25 ml of anhydrous dichloromethane;

[0085] 2) Slowly add 3.07 g of diketene (1.1 eq., 97%) to the above solution;

[0086] 3) The above solution was magnetically stirred at room temperature, and 100 μl of triethylamine (99.0%) was added dropwise;

[0087] 4) Continue stirring the above solution at room temperature for 12 hours;

[0088] 5) The solution after the reaction is rotary evaporated to remove the dichloromethane solvent to obtain a crude n-butyl thioacetoacetate sample.

[0089] The synthetic route is as follows:

[0090]

[0091] The crude n-butyl thioacetoacetate is purified by passing through a silica gel column to remove excess impurities such as diketene and triethylamine.

[0092] Fig.10 Shown is the hydrogen spectrum of n-butylthioacetoacetate prepared as described above.

[0093] Secondly, the applicant synthesized n-butyl-ethyleneamine thioester, and the specific synthesis steps are as follows:

[0094] 1) 3 g (1 eq.) of n-butylthioacetoacetate and 1.33 g (1.05 eq.) of n-butylamine (99%) were added into a round-bottom flask in sequence;

[0095] 2) Mix and stir the bulk at 80°C for 4 hours;

[0096] 3) Purifying the reacted sample through a silica gel column, with ethyl acetate as the eluent;

[0097] 4) Remove ethyl acetate by rotary evaporation to obtain pure n-butyl-ethyleneamine thioester.

[0098] The synthetic route is as follows:

[0099]

[0100] Next, to study the dynamic exchange kinetics of ethylene aminothioester bonds, the steps are as follows:

[0101] 1) Dissolve 30 mg (1 eq.) of n-butyl-vinylamine thioester in 2.5 ml of deuterated DMSO in a 5 ml glass bottle;

[0102] 2) Take another 5 ml glass bottle and dissolve 70 mg (5 eq.) benzylamine in 2.5 ml deuterated DMSO;

[0103] 3) The two vials were quickly mixed at room temperature and magnetically stirred for 5 minutes;

[0104] The obtained mixed solution was divided into 10 portions (0.5 ml) and added into 10 NMR tubes respectively;

[0105] Immerse 10 NMR tubes in an oil bath at specific temperature (100, 120, 140℃), take out one NMR tube at 0h, 0.5h, 1h, 2h, 4h, 6h, 8h, 10h, 14h, and 24h respectively, and quickly quench it with liquid nitrogen.

[0106] The exchange reaction route is as follows:

[0107]

[0108] The exchange kinetics were calculated by the change in the integrated area of ​​specific peaks in the H-NMR spectrum. Fig.11 As shown. Fig.11 It can be seen that the dynamic exchange kinetics of ethylene aminothioester bonds obeys first-order kinetics, and the exchange rate increases with the increase of exchange temperature.

[0109] (II) Synthesis and confirmation of n-butyl acetoacetate and n-butyl vinylamine ester

[0110] The applicant first synthesized n-butyl acetoacetate, whose structural formula is The specific implementation is as follows:

[0111] 1) Dissolve 3 g (1 eq.) of n-butanol (99.5%) in 25 ml of anhydrous dichloromethane;

[0112] 2) Slowly add 3.84 g of diketene (1.1 eq., 97%) to the above solution;

[0113] 3) The above solution was magnetically stirred at room temperature, and 100 μl of triethylamine (99.0%) was added dropwise;

[0114] 4) Continue stirring the above solution at room temperature for 12 hours;

[0115] 5) The solution after the reaction was rotary evaporated to remove the dichloromethane solvent to obtain a crude n-butyl acetoacetate sample.

[0116] The synthetic route is as follows:

[0117]

[0118] The crude n-butyl acetoacetate is purified by passing through a silica gel column to remove excess impurities such as diketene and triethylamine.

[0119] Fig.12 Shown is the hydrogen spectrum of n-butyl acetoacetate prepared as described above.

[0120] Secondly, the applicant synthesized n-butyl-vinylamine ester by the following steps, and the specific steps are as follows:

[0121] 1) 3 g (1 eq.) of n-butyl acetoacetate and 1.47 g (1.05 eq.) of n-butylamine (99%) were added into a round-bottom flask in sequence;

[0122] 2) Mix and stir the bulk at 80°C for 4 hours;

[0123] 3) Purifying the reacted sample through a silica gel column, with ethyl acetate as the eluent;

[0124] 4) Remove ethyl acetate by rotary evaporation to obtain pure n-butyl-vinylamine ester.

[0125] The synthetic route is as follows:

[0126]

[0127] Next, to study the dynamic exchange kinetics of the ester bond of vinylamine, the steps are as follows:

[0128] 1) 30 mg (1 eq.) of n-butyl-vinylamine ester was dissolved in 2.5 ml of deuterated DMSO in a 5 ml glass vial.

[0129] 2) Take another 5 ml glass bottle and dissolve 76.2 mg (5 eq.) of benzylamine in 2.5 ml of deuterated DMSO.

[0130] 3) The two vials were quickly mixed at room temperature with magnetic stirring for 5 minutes.

[0131] The mixed solution was divided into 10 equal portions (0.5 ml) and added into 10 NMR tubes respectively; the 10 NMR tubes were immersed in an oil bath at specific temperature (100, 120, 140°C), and one NMR tube was taken out and quickly quenched with liquid nitrogen at 0h, 0.5h, 1h, 2h, 4h, 6h, 8h, 10h, 14h, and 24h respectively; the exchange kinetics was calculated by the change in the integrated area of ​​specific peaks in the NMR hydrogen spectrum.

[0132] The exchange reaction route is as follows:

[0133]

[0134] Dynamic exchange kinetics of vinylamine ester bonds Fig.13 As shown. Fig.13 It can be seen that the dynamic exchange kinetics of the vinyl urethane bond also obeys first-order kinetics, and the exchange rate increases with the increase of the exchange temperature.

[0135] Compare Fig.11 and Fig.13 It can be seen that at the same temperature, the exchange rate of vinylamine ester bonds (containing -O-) is faster than the exchange rate of vinylamine thioester bonds (containing -S-).

[0136] However, in the technical solution of the present application, the opposite results of the dynamic exchangeability of small molecules and the dynamic exchangeability after forming a cross-linked network are presented. For the dynamic cross-linked network composed of vinylamine thioester bonds (containing -S-) (Example 2), its stress relaxation time at the same temperature is much shorter than that of the dynamic cross-linked network composed of vinylamine ester bonds (containing -O-) (Comparative Example 2), proving that the exchange rate of Example 2 is faster than that of Comparative Example 2. However, in the small molecule exchange kinetics experiment, the exchange rate of vinylamine thioester bonds (containing -S-) is slower than that of vinylamine ester bonds (containing -O-).

[0137] The above embodiments are merely illustrative of the principles and effects of the present invention, and are not intended to limit the present invention. Anyone familiar with the art may modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by a person of ordinary skill in the art without departing from the spirit and technical concept disclosed by the present invention shall still be covered by the claims of the present invention.

Claims

1. A compound, characterized in that The compound is 2,2′-(1,2-ethylenedioxy)acetoacetate diethylthioester, and the structural formula is shown in Formula 1: Formula 1.

2. The method for preparing the compound according to claim 1, characterized in that: 2,2'-(1,2-ethylenediyldioxy) bisethylthiol is reacted with diketene to obtain bisethylthio 2,2'-(1,2-ethylenediyldioxy) acetoacetate.

3. The preparation method according to claim 2, characterized in that: The reaction is carried out in a first organic solvent.

4. The preparation method according to claim 2, characterized in that: An acid binding agent is also used in the reaction.

5. The preparation method according to claim 3, characterized in that: The first organic solvent is dichloromethane.

6. The preparation method according to claim 4, characterized in that: The acid binding agent is triethylamine.

7. Use of the compound according to claim 1 as a raw material for preparing a polymer with dynamic functions.

8. A polymer with dynamic functions, characterized in that: The polymer is a dynamic cross-linked network formed by reacting the compound as shown in claim 1 with tris(2-aminoethyl)amine.

9. The polymer according to claim 8, characterized in that The reaction temperature is 30-150°C.

10. The polymer according to claim 8, characterized in that The solvent in the reaction is acetonitrile.

11. The polymer according to claim 8, characterized in that The molar ratio of the acetoacetic acid groups of the compound represented by Formula I to the primary amine groups of tris(2-aminoethyl)amine is less than 1.

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