Guanidinyl-containing antibacterial polymers, methods of making, and uses thereof

Abstract

The application provides a guanidine-containing antibacterial polymer, a preparation method and application thereof, and has the structure shown in the following formula I. When a nanofiber membrane prepared from the guanidine-containing antibacterial polymer is used to filter PM in air, the nanofiber membrane has good filtering effect, and has good bacteriostatic effect on staphylococcus aureus and escherichia coli, and even has better bacteriostatic effect when stored for a long time.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis, specifically relating to a guanidine-containing antibacterial polymer, its preparation method, and its application. Background Technology

[0002] Electrospun nanofibers refer to the process of applying an electrostatic voltage to a polymer solution. Under the influence of the electrostatic voltage's electric field, the polymer solution is stretched over a very short time and a certain distance, causing the solvent to evaporate and ultimately forming nanofibers on a grounded receiving plate. This method can be used to prepare most polymer nanofibers, such as PVA, PVP, PAN, PVDF, PES, PS, and PU, and the resulting fibers have diverse morphologies and wide applications. Among these, nanofiber membranes have found widespread use in filtration due to their excellent particle blocking properties (effectively filtering out particulate pollutants such as fine particulate matter, carbon dioxide, and sulfur dioxide), high specific surface area, and good adsorption capacity.

[0003] However, existing electrospun nanofibers are made from polymers and can only intercept and electrostatically adsorb suspended particles in the air, but cannot remove bacteria, viruses, and organic pollutants. Driven by this background and application needs, research has begun on nanofiber filter materials with antibacterial functions. For example, Chinese patent document "CN102302875A" discloses a method for preparing an antibacterial air filter membrane. This method involves blending an inorganic antibacterial agent containing metal or an organic antibacterial agent containing sulfur or bromine, a polymer, additives, and a solvent into a solution; or melting the antibacterial agent and polymer to obtain a homogeneous melt; then electrospinning the blended solution or melt onto the surface of a nonwoven fabric to obtain the antibacterial air filter membrane. The resulting antibacterial air filter membrane has excellent antibacterial effects, but with prolonged use, phenomena such as deposition and delamination may occur, leading to a decrease in antibacterial performance.

[0004] In view of the problems existing in the prior art, how to provide a guanidine-containing antibacterial polymer with good filtration effect and antibacterial properties, and which still has good antibacterial properties when used for a long time, is the problem that this invention urgently needs to solve. Summary of the Invention

[0005] The purpose of this invention is to provide a guanidine-containing antibacterial polymer, its preparation method, and its application, in order to solve the problems mentioned in the background art.

[0006] To achieve the above objectives, the present invention provides the following technical solution: In one aspect, the present invention provides a guanidine-containing antibacterial polymer, which has the structure shown in Formula I:

[0007]

[0008] Wherein, R1 represents formyl, acetyl, substituted or unsubstituted aryl or carboxyl containing 1-5 carbon atoms; R2 and R3 each independently represent hydrogen, hydroxyl or methyl; R4 represents benzyl, phenyl, biphenyl, straight-chain or branched alkyl containing 1-8 carbon atoms;

[0009] x, y, a, and b all represent integers, and x:y is 3:(1-3), a represents 30-100, and b represents 20-80.

[0010] As a further improvement, the substituted or unsubstituted aryl group in R1 is... R5 represents hydrogen, methyl, or ethyl.

[0011] As a further improvement, the guanidine-containing antibacterial polymer is selected from the group consisting of compounds represented by formulas I-1 to I-3 as follows:

[0012]

[0013] R4 represents a straight-chain or branched alkyl group containing 1-8 carbon atoms.

[0014] On the other hand, the present invention provides a method for preparing a guanidine-containing antibacterial polymer, comprising the following steps:

[0015] (1) After adding acrylic monomers and styrene monomers to a volatile organic solvent and mixing them evenly, add initiator BPO and organic polymer chain transfer agent shown in formula II-C to prepare a mixed solution;

[0016] (2) After adding a volatile organic solvent to the reaction flask and heating it to 80-100℃, the mixed solution from step (1) is added dropwise over a period of 2-6 hours. After the addition is completed, the reaction is kept at the temperature for 2-4 hours. Then, the mixture is post-treated to obtain a guanidine-containing antibacterial polymer.

[0017]

[0018] As a further improvement, styrene monomers include styrene, methylstyrene, p-hydroxystyrene, etc.

[0019] As a further improvement, the method for preparing the organic polymer chain transfer agent includes the following steps:

[0020] (1.1) Hydroxyethyl acrylate and polymerizable guanidine monomers are added to ethyl acetate and mixed evenly. After mixing evenly, a thermal initiator is added to obtain a mixed solution.

[0021] (1.2) Add ethyl acetate to the reaction flask, heat the ethyl acetate in the reaction flask to 60-80℃, start adding the mixed solution from step (1.1) dropwise, the dropwise addition time is 2-6 hours, after the dropwise addition is completed, keep the reaction at the temperature for 2-4 hours, and then perform post-treatment to obtain the organic polymer;

[0022] (1.3) The organic polymer obtained in step (1.2) is added to an ether-based organic solvent, and tetrakis(triphenylphosphine)palladium, potassium carbonate, water, and 4-mercaptophenylboronic acid are added. The mixture is reacted at 70-90°C to obtain an organic polymer chain transfer agent, wherein the polymerizable guanidine monomer represents...

[0023] As a further improvement, the method for preparing the thermal initiator includes the following steps:

[0024] Sodium dodecylbenzenesulfonate and sodium carbonate were dissolved in water and mixed evenly at room temperature. A 25-40% hydrogen peroxide solution was added, and 3-bromobenzoyl chloride was added dropwise. After the addition was complete, the temperature was raised to 30-40℃. After the reaction was completed, post-treatment was performed to obtain the thermal initiator.

[0025] As a further improvement, the method for preparing the polymerizable guanidine monomer includes the following steps:

[0026] Guanidinyl monomer and triethylamine were added to a low-boiling-point organic solvent, the system was cooled to -10 to 0°C, and acryloyl chloride was added dropwise. After the addition was complete, the reaction was allowed to proceed for 2 to 4 hours. After the reaction was completed, post-treatment was performed to obtain polymerizable guanidinyl monomer.

[0027] Wherein, guanidino monomer represents

[0028] As a further improvement, the guanidinium monomers include acetylguanidine, phenyl biguanide, guanidinium propionic acid, guanidinium acetic acid, 4-guanidinium butyric acid, etc.

[0029] As a further improvement, the catalyst is a palladium catalyst, such as tetraphenylphosphine palladium.

[0030] On the other hand, the present invention also provides the use of guanidine-containing antimicrobial polymers in antimicrobial agents.

[0031] As a further improvement, the antibacterial agent is used in the preparation of antibacterial nanofiber membranes.

[0032] Compared with the prior art, the beneficial effects of the present invention are:

[0033] The nanofiber membrane made from the guanidine-containing antibacterial polymer provided in this application has a good filtration effect on PM in the air and a good antibacterial effect on Staphylococcus aureus and Escherichia coli. Even when stored for a long time, it has a better antibacterial effect. Detailed Implementation

[0034] The present invention will be described below with reference to specific embodiments. It should be noted that the following embodiments are examples of the present invention and are used only to illustrate the invention, not to limit it. Other combinations and various modifications within the scope of the present invention can be made without departing from its spirit or scope. In the following embodiments, except for compounds of formula I-1-A, II-A-1, II-B, II-C-1, I-2-A, II-A-2, II-C-1, I-3-A, II-A-3, II-C-3, I-4-A, II-C-4, I-5-A, and II-C-5, all other monomers and related reagents used are commercially available.

[0035] The preparation method of compound I-1-A is as follows:

[0036] (1) 35 mol of phenyl biguanide and 4 mol of triethylamine were added to 500 mL of toluene. The system was cooled to -10 °C and 35 mol of acryloyl chloride was added dropwise. After the addition was complete, the reaction was continued at -10 °C for 3 hours. After the reaction was completed, 300 mL of deionized water was added. The organic layer was extracted by separation and the toluene was removed by distillation to obtain the compound of formula II-A-1.

[0037]

[0038] (2) Dissolve 0.003 mol sodium dodecylbenzenesulfonate and 0.28 mol sodium carbonate in 100 mL of water, mix them evenly at room temperature, add 0.15 mol of 30% hydrogen peroxide solution (hydrogen peroxide solution is a solution composed of hydrogen peroxide and water), and add 0.1 mol of 3-bromobenzoyl chloride dropwise. After the addition is complete, heat to 40 °C and react for 3 h. Filter to collect the solid, wash the filter cake with a large amount of deionized water, and dry at low temperature (30 °C) to obtain the compound of formula II-B.

[0039]

[0040] (3) Add 10 mol of hydroxyethyl acrylate and 30 mol of compound II-A-1 to 800 mL of ethyl acetate and mix well. After mixing well, add 1.2 mol of compound II-B to obtain a mixed solution.

[0041] 800 mL of ethyl acetate was added to a reaction flask, and the ethyl acetate in the reaction flask was heated to 70 °C. The mixed solution was then added dropwise over a period of 4 hours. After the addition was completed, the mixture was reacted at 70 °C for 3 hours. After removing the ethyl acetate by distillation, the organic polymer was obtained. 1 mol of the obtained organic polymer was added to 1.5 mol of tetrahydrofuran, and 0.002 mol of tetratriphenylphosphine palladium, 0.07 mol of potassium carbonate, 40 mL of water, and 2.5 mol of 4-mercaptophenylboronic acid were added. The mixture was reacted at 80 °C to obtain the compound of formula II-C-1.

[0042]

[0043] (4) 105 mol of butyl acrylate and 105 mol of styrene were added to 1000 mL of toluene and mixed evenly. Then, 1.2 mol of initiator BPO and 1 mol of compound II-C-1 were added to prepare a mixed solution. 1500 mL of toluene was added to the reaction flask and the temperature was raised to 90 °C. The mixed solution was added dropwise over 4 hours. After the addition was completed, the reaction was kept at the temperature for 3 hours. After the toluene was removed by distillation, compound I-1-A was obtained.

[0044]

[0045] The preparation method of compound I-2-A is as follows:

[0046] (1) 32 mol of guanidinoacetic acid and 4 mol of triethylamine were added to 500 mL of toluene. The system was cooled to -8 °C and 32 mol of acryloyl chloride was added dropwise. After the addition was complete, the reaction was continued at -8 °C for 3 hours. After the reaction was completed, 280 mL of deionized water was added. The organic layer was extracted by separation and the toluene was removed by distillation to obtain the compound of formula II-A-2.

[0047]

[0048] (2) Dissolve 0.003 mol sodium dodecylbenzenesulfonate and 0.28 mol sodium carbonate in 100 mL of water, mix them evenly at room temperature, add 0.15 mol of 30% hydrogen peroxide solution (hydrogen peroxide solution is a solution composed of hydrogen peroxide and water), and add 0.1 mol of 3-bromobenzoyl chloride dropwise. After the addition is complete, heat to 40 °C and react for 3 h. Filter to collect the solid, wash the filter cake with a large amount of deionized water, and dry at low temperature (30 °C) to obtain the compound of formula II-B.

[0049]

[0050] (3) Add 15 mol of hydroxyethyl acrylate and 30 mol of formula II-A-2 to 1000 mL of ethyl acetate and mix well. After mixing well, add 1.5 mol of compound II-B to obtain a mixed solution.

[0051] 1000 mL of ethyl acetate was added to a reaction flask, and the ethyl acetate in the reaction flask was heated to 80 °C. The mixed solution was then added dropwise over a period of 5 hours. After the addition was completed, the mixture was reacted at 80 °C for 4 hours. After removing the ethyl acetate by distillation, the organic polymer was obtained. 1 mol of the obtained organic polymer was added to 2 mol of tetrahydrofuran, and 0.003 mol of tetratriphenylphosphine palladium, 0.09 mol of potassium carbonate, 60 mL of water, and 3 mol of 4-mercaptophenylboronic acid were added. The mixture was reacted at 80 °C to obtain the compound of formula II-C-2.

[0052]

[0053] (4) 105 mol of butyl acrylate and 105 mol of styrene were added to 1000 mL of toluene and mixed evenly. Then, 1.4 mol of initiator BPO and 1 mol of compound II-C-2 were added to prepare a mixed solution. 1500 mL of toluene was added to the reaction flask and the temperature was raised to 90 °C. The mixed solution was added dropwise over 4 hours. After the addition was completed, the reaction was kept at the temperature for 3 hours. After distilling to remove the toluene, compound I-1-A-2 was obtained.

[0054]

[0055] The preparation method of compound I-3-A is as follows:

[0056] (1) 32 mol of guanidinopropionic acid and 4 mol of triethylamine were added to 500 mL of toluene. The system was cooled to -10 °C and 32 mol of acryloyl chloride was added dropwise. After the addition was completed, the reaction was continued at -10 °C for 3 hours. After the reaction was completed, 280 mL of deionized water was added. The organic layer was extracted by separation and the toluene was removed by distillation to obtain the compound of formula II-A-3.

[0057]

[0058] (2) Dissolve 0.003 mol sodium dodecylbenzenesulfonate and 0.28 mol sodium carbonate in 100 mL of water, mix them evenly at room temperature, add 0.15 mol of 30% hydrogen peroxide solution (hydrogen peroxide solution is a solution composed of hydrogen peroxide and water), and add 0.1 mol of 3-bromobenzoyl chloride dropwise. After the addition is complete, heat to 40 °C and react for 3 h. Filter to collect the solid, wash the filter cake with a large amount of deionized water, and dry at low temperature (30 °C) to obtain the compound of formula II-B.

[0059]

[0060] (3) Add 20 mol of hydroxyethyl acrylate and 30 mol of formula II-A-3 to 1200 mL of ethyl acetate and mix well. After mixing well, add 1.6 mol of compound II-B to prepare a mixed solution.

[0061] 1200 mL of ethyl acetate was added to a reaction flask, and the ethyl acetate in the reaction flask was heated to 70 °C. The mixed solution was then added dropwise over a period of 5 hours. After the addition was completed, the mixture was reacted at 70 °C for 3 hours. After removing the ethyl acetate by distillation, the organic polymer was obtained. 1 mol of the obtained organic polymer was added to 2.4 mol of tetrahydrofuran, and 0.005 mol of tetratriphenylphosphine palladium, 0.09 mol of potassium carbonate, 60 mL of water, and 2.5 mol of 4-mercaptophenylboronic acid were added. The mixture was reacted at 80 °C to obtain a compound of formula II-C-3.

[0062]

[0063] (4) 105 mol of butyl acrylate and 105 mol of p-hydroxystyrene were added to 1500 mL of toluene and mixed evenly. Then, 1.8 mol of initiator BPO and 1 mol of compound II-C-3 were added to prepare a mixed solution. 1600 mL of toluene was added to the reaction flask and the temperature was raised to 90 °C. The mixed solution was added dropwise over 4 hours. After the addition was completed, the reaction was kept at the temperature for 3 hours. After distilling to remove the toluene, compound I-3-A was obtained.

[0064]

[0065] The preparation method of compound I-4-A is basically the same as that of compound I-1-A, except that steps (3) and (4) are replaced in the preparation method of compound I-1-A, as follows:

[0066] (3) Add 40 mol of hydroxyethyl acrylate and 30 mol of compound II-A-1 to 800 mL of ethyl acetate and mix well. After mixing well, add 1.2 mol of compound II-B to obtain a mixed solution.

[0067] 800 mL of ethyl acetate was added to a reaction flask, and the ethyl acetate in the reaction flask was heated to 70 °C. The mixed solution was then added dropwise over a period of 4 hours. After the addition was completed, the mixture was reacted at 70 °C for 3 hours. After removing the ethyl acetate by distillation, the organic polymer was obtained. 1 mol of the obtained organic polymer was added to 1.5 mol of tetrahydrofuran, and 0.002 mol of tetratriphenylphosphine palladium, 0.07 mol of potassium carbonate, 40 mL of water, and 2.5 mol of 4-mercaptophenylboronic acid were added. The mixture was reacted at 80 °C to obtain a compound of formula II-C-4.

[0068]

[0069] (4) 105 mol of butyl acrylate and 105 mol of styrene were added to 1500 mL of toluene and mixed evenly. Then, 1.4 mol of initiator BPO and 1 mol of compound II-C-4 were added to prepare a mixed solution. 1500 mL of toluene was added to the reaction flask and the temperature was raised to 90 °C. The mixed solution was added dropwise over 4 hours. After the addition was completed, the reaction was kept at the temperature for 3 hours. After the toluene was removed by distillation, compound I-4-A was obtained.

[0070]

[0071] The preparation method of compound I-5-A is basically the same as that of compound I-1-A, except that steps (3) and (4) are replaced in the preparation method of compound I-1-A, as follows:

[0072] (3) Add 5 mol of hydroxyethyl acrylate and 30 mol of compound II-A-1 to 800 mL of ethyl acetate and mix well. After mixing well, add 1.2 mol of compound II-B to obtain a mixed solution.

[0073] 800 mL of ethyl acetate was added to a reaction flask, and the ethyl acetate in the reaction flask was heated to 70 °C. The mixed solution was then added dropwise over a period of 4 hours. After the addition was completed, the mixture was reacted at 70 °C for 3 hours. After removing the ethyl acetate by distillation, the organic polymer was obtained. 1 mol of the obtained organic polymer was added to 50 mL of tetrahydrofuran, and 0.002 mol of tetratriphenylphosphine palladium, 0.07 mol of potassium carbonate, 40 mL of water, and 2.5 mol of 4-mercaptophenylboronic acid were added. The mixture was reacted at 80 °C to obtain the compound of formula II-C-5.

[0074]

[0075] (4) 105 mol of butyl acrylate and 105 mol of styrene were added to 1500 mL of toluene and mixed evenly. Then, 1.4 mol of initiator BPO and 1 mol of compound II-C-5 were added to prepare a mixed solution. 1500 mL of toluene was added to the reaction flask and the temperature was raised to 90 °C. The mixed solution was added dropwise over 4 hours. After the addition was completed, the reaction was kept at the temperature for 3 hours. After the toluene was removed by distillation, compound I-5-A was obtained.

[0076]

[0077] Sample preparation for Examples 1 to 3 and Comparative Examples 1 to 2:

[0078] Add 30mN,N-dimethylformamide solvent and 10mL acetone to 1.5kg of compound I, stir until evenly dispersed, spin the resulting polymer spinning solution by electrospinning, wash the obtained product with deionized water, and dry the washed product in a benchtop drying oven to obtain a nanofiber membrane.

[0079] In Example 1, the compound of Formula I used was compound I-1-A; in Example 2, the compound of Formula I used was compound I-2-A; in Example 3, the compound of Formula I used was compound I-3-A; in Comparative Example 1, the compound of Formula I used was compound I-4-A; and in Comparative Example 2, the compound of Formula I used was compound I-5-A.

[0080] Comparative Example 3 Sample Preparation: 30 mL of N,N-dimethylformamide solvent and 10 mL of acetone were added to 1.5 kg of polystyrene and stirred until evenly dispersed. The resulting polymer spinning solution was spun by electrospinning. The obtained product was washed with deionized water and dried in a benchtop drying oven to obtain a nanofiber membrane. The polystyrene was purchased from Ningbo Xinsuyuan Plastics Co., Ltd., product number 220115.

[0081] Comparative Example 4 Sample Preparation: 0.2 g g-C3N4 nanoparticles were mixed with 30 mL N,N-dimethylformamide solvent and 10 mL acetone, and then treated in an oxygen plasma atmosphere for 400 s. Polystyrene was then added and stirred until uniformly dispersed, allowing the nanoparticles to be exfoliated into nanosheets with a particle size of 30 nm. The resulting polymer spinning solution was spun by electrospinning. The obtained product was washed with deionized water and dried in a benchtop drying oven. The product was then treated in a uniform nitrogen glow discharge plasma atmosphere for 300 s. After that, a dispersion containing 0.5 wt% g-C3N4 nanosheets (particle size of 30 nm) was sprayed onto the product for 15 s and dried at room temperature to obtain a nanofiber membrane.

[0082] Test method:

[0083] Cigarette smoke filtration test: Refer to patent "CN107551831B" for cigarette smoke filtration test. The specific test method is as follows:

[0084] The nanofiber membranes prepared in Examples 1 to 3 and Comparative Examples 1 to 4 were used in a tobacco smoke particulate matter filtration test. The apparatus used is shown in Figure 5 of patent "CN107551831B". A circular fiber membrane with a diameter of 2 cm and a thickness of 400 μm was sealed and fixed at the connection between two empty bottles. A burning cigarette (with the burning end facing the outside air) was inserted into the interface of the right bottle of the apparatus. The apparatus was then sealed, and a vacuum pump was connected to the interface of the left bottle for intermittent suction. The concentration of particulate matter in the left bottle of the apparatus was measured using a handheld particulate matter detector. Test conditions: T = 23℃, RH = 50%, PM2.5 in the right bottle = 390 μg / m³. 3 PM10 = 0.8 mg / m³ 3 .

[0085] Antibacterial test: The test was conducted according to the national standard GB / T 20944.3-2008. During the antibacterial test, the antibacterial effect of the nanofiber membranes prepared in Examples 1 to 3 and Comparative Examples 1 to 4 were tested after 10 days of storage and 6 months of storage.

[0086] The test results are shown in Table 1, and are as follows:

[0087]

[0088] As can be seen from the comparison of Example 1 and Comparative Examples 3 to 4, the nanofiber membrane made of the guanidine-containing antibacterial polymer provided in this application filters PM in the air and the quality level of PM2.5 and PM10 in the air is excellent. It also has a good antibacterial effect against Staphylococcus aureus and Escherichia coli, and it still has a good antibacterial effect even when stored for a long time.

[0089] As can be seen from the comparison of Example 1 and Comparative Examples 1 to 2, when the x:y ratio in the guanidine-containing antibacterial polymer is 3:(1-3), the nanofiber membrane made of the guanidine-containing antibacterial polymer provided in this application not only has a better filtration effect when filtering PM in the air, but also has a better antibacterial effect against Staphylococcus aureus and Escherichia coli, and also has a better antibacterial effect when stored for a long time.

[0090] A comparison of Examples 1 to 3 shows that when the ratio of x to y of the guanidine-containing antibacterial polymer is 3:(1-3), where a represents 30-100 and b represents 20-80, the nanofiber membrane made from the guanidine-containing antibacterial polymer provided in this application has a good filtration effect on PM in the air and a good antibacterial effect on Staphylococcus aureus and Escherichia coli. The antibacterial effect is also better when stored for a long time.

[0091] In summary, the nanofiber membrane made from the guanidine-containing antibacterial polymer provided in this application has a good filtration effect on PM in the air, and also has a good antibacterial effect on Staphylococcus aureus and Escherichia coli. It also has a better antibacterial effect during long-term storage.

[0092] It should be noted that, in this document, relational terms such as "first" and "second" are used only to distinguish one entity or operation from another, and do not necessarily require or imply any such actual relationship or order between these entities or operations. Furthermore, the terms "comprising," "including," or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such process, method, article, or apparatus.

[0093] Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions, and variations can be made to these embodiments without departing from the principles and spirit of the invention. The scope of the invention is defined by the appended claims and their equivalents. Obviously, the embodiments described in this invention are only a part of the embodiments of the invention, and not all of them. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without inventive effort are within the scope of protection of the present invention.

Claims

1. A guanidine-containing antibacterial polymer, characterized in that: The preparation of this guanidine-containing antibacterial polymer includes the following steps: (1) After adding acrylic monomers and styrene monomers to a volatile organic solvent and mixing them evenly, add initiator BPO and organic polymer chain transfer agent shown in formula II-C to prepare a mixed solution; (2) After adding a volatile organic solvent to the reaction flask and heating it to 80-100℃, the mixed solution from step (1) is added dropwise over a period of 2-6 hours. After the addition is complete, the reaction is kept at the temperature for 2-4 hours. Then, the mixture is post-treated to obtain a guanidine-containing antibacterial polymer. Ⅱ-C； Wherein, R1 represents formyl, acetyl, substituted or unsubstituted aryl, or carboxyl containing 1-5 carbon atoms; x and y both represent integers, and x:y is 3:(1-3).

2. The guanidine-containing antibacterial polymer according to claim 1, characterized in that: The aryl group substituted in R1 is R5 represents hydrogen, methyl, or ethyl.

3. A method for preparing a guanidine-containing antibacterial polymer according to any one of claims 1-2, characterized in that: Includes the following steps: (1) After adding acrylic monomers and styrene monomers to a volatile organic solvent and mixing them evenly, add initiator BPO and organic polymer chain transfer agent shown in formula II-C to prepare a mixed solution; (2) After adding a volatile organic solvent to the reaction flask and heating it to 80-100℃, the mixed solution from step (1) is added dropwise over a period of 2-6 hours. After the addition is complete, the reaction is kept at the temperature for 2-4 hours. Then, the mixture is post-treated to obtain a guanidine-containing antibacterial polymer. Ⅱ-C。 4. The method for preparing a guanidine-containing antibacterial polymer according to claim 3, characterized in that: The preparation method of the organic polymer chain transfer agent includes the following steps: (1.1) Hydroxyethyl acrylate and polymerizable guanidine monomers are added to ethyl acetate and mixed evenly. After mixing evenly, a thermal initiator is added to obtain a mixed solution. (1.2) Add ethyl acetate to the reaction flask, heat the ethyl acetate in the reaction flask to 60-80℃, start adding the mixed solution from step (1.1) dropwise, the dropwise addition time is 2-6 hours, after the dropwise addition is completed, keep the reaction at the temperature for 2-4 hours, and then perform post-treatment to obtain the organic polymer; (1.3) The organic polymer obtained in step (1.2) is added to an ether-based organic solvent, and a catalyst, potassium carbonate, water, and 4-mercaptophenylboronic acid are added. The mixture is reacted at 70-90°C to obtain an organic polymer chain transfer agent, wherein the polymerizable guanidine monomer represents... .

5. The method for preparing a guanidine-containing antibacterial polymer according to claim 4, characterized in that: The method for preparing the thermal initiator includes the following steps: Sodium dodecylbenzenesulfonate and sodium carbonate were dissolved in water and mixed evenly at room temperature. A 25-40% hydrogen peroxide solution was added, and 3-bromobenzoyl chloride was added dropwise. After the addition was complete, the temperature was raised to 30-40℃. After the reaction was completed, post-treatment was performed to obtain the thermal initiator.

6. The method for preparing a guanidine-containing antibacterial polymer according to claim 4, characterized in that: The method for preparing the polymerizable guanidine monomer includes the following steps: Guanidinyl monomer and triethylamine were added to a low-boiling-point organic solvent, the system was cooled to -10 to 0°C, and acryloyl chloride was added dropwise. After the addition was complete, the reaction was allowed to proceed for 2 to 4 hours. After the reaction was completed, post-treatment was performed to obtain polymerizable guanidinyl monomer. Wherein, guanidino monomer represents .

7. The method for preparing a guanidine-containing antibacterial polymer according to claim 4, characterized in that: The catalyst is a palladium catalyst.

8. The use of the guanidine-containing antibacterial polymer according to any one of claims 1-2 in the preparation of antibacterial agents.

9. The application according to claim 8, characterized in that: The application of the antibacterial agent in the preparation of antibacterial nanofiber membranes.

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