Preparation method of sodium methacryloyl taurate monomer, taurine-containing polymer derived from sodium methacryloyl taurate monomer, and preparation method and application of taurine-containing polymer
By using a tetrahydrofuran system and hydrogen phosphate or bicarbonate salts to activate the taurine amino group in the acyl chloride process, converting it into an organic-solid phase reaction, the problem of low yield in the synthesis of taurine monomers by the acyl chloride process was solved. This achieved an efficient and simple preparation process, improved yield and purity, and laid the foundation for industrialization.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- UNIV OF SCI & TECH BEIJING
- Filing Date
- 2026-01-08
- Publication Date
- 2026-05-12
AI Technical Summary
The existing acyl chloride method for synthesizing taurine monomers has a low yield, mainly due to the rapid hydrolysis of small molecule acyl chlorides at the aqueous interface and the reduced nucleophilic activity caused by the amino protonation of taurine.
A tetrahydrofuran or 2-methyltetrahydrofuran system is used. A sodium/potassium salt containing hydrogen phosphate or bicarbonate is added to form a suspension, which is then reacted with methacryloyl chloride to convert it into an organic-solid phase reaction system. The hydrogen phosphate or bicarbonate is used to activate the taurine amino group, absorb the reaction byproduct hydrogen halide, and reduce the hydrolysis of acryloyl chloride.
This method improves the yield and purity of taurine monomers synthesized via the acyl chloride method, simplifies the preparation process, reduces the technical difficulty and cost of large-scale production, and promotes the industrial application of taurine-containing polymers.
Smart Images
Figure CN122010792A_ABST
Abstract
Description
Technical Field
[0001] This application belongs to the field of polymer synthesis technology, and specifically relates to a method for preparing sodium methacryloyl taurate monomer, a taurine-containing polymer derived from the monomer, its preparation method, and its application. Background Technology
[0002] Taurine-derived polymers are widely used in biomedicine, membrane modification, and chromatographic separation due to their excellent biocompatibility, hydrophilicity, and ionization ability. However, traditional preparation methods for taurine-containing polymers mainly rely on polymer grafting modification, which generally suffers from low grafting rates, poor controllability, high costs, and significant pollution, making large-scale preparation very difficult and greatly limiting the application and commercialization of taurine-containing polymers. Therefore, the preparation route using taurine-based unsaturated monomers through copolymerization has become a research hotspot in the field of taurine-containing polymer preparation.
[0003] Currently, the acyl chloride method is one of the most effective strategies for constructing taurine monomers. Its core principle is to prepare functional monomers by reacting acyl chlorides with taurine, and then synthesize taurine-containing polymers via free radical polymerization. This method does not require condensing agents, and the polymerization process is mature and controllable, making it considered an effective approach for large-scale production. For example, Christopher P. Palmer et al. prepared 10-undecenoyl taurine monomers by reacting 10-undecenoyl chloride with taurine, and then obtained the corresponding taurine-containing polymers via free radical polymerization.
[0004] However, the existing acyl chloride method for synthesizing taurine monomers generally suffers from low yields, which are mainly due to two reasons: First, taurine is only soluble in water, while small molecule acyl chlorides are easily hydrolyzed, requiring a two-phase reaction between an aqueous phase and an organic phase. However, small molecule acyl chlorides undergo rapid hydrolysis at the aqueous phase interface, reducing utilization. Second, the sulfonic acid group of taurine is significantly acidic, which easily causes its amino group to protonate and lose its nucleophilic activity. Alkali activation of the amino group is required, but the alkaline environment further exacerbates the hydrolysis of small molecule acyl chlorides. These factors together result in generally low yields (15-20%) of taurine monomers synthesized by the acyl chloride method. Summary of the Invention
[0005] This application effectively solves the technical problem of low yield in the existing acyl chloride method for synthesizing taurine monomers by disclosing a method for preparing sodium methacryloyl taurate monomer, the taurine-containing polymer derived from this monomer, its preparation method, and its application.
[0006] To achieve the above objectives, the technical solution provided in this application is as follows:
[0007] The first aspect of this application provides a method for preparing sodium methacryloyl taurate monomer, the method comprising:
[0008] After reacting taurine with sodium hydroxide in water, the reaction solution is added to tetrahydrofuran or 2-methyltetrahydrofuran, and then sodium / potassium salts containing hydrogen phosphate or bicarbonate are added to prepare a suspension.
[0009] After adding a solution of methacryloyl chloride in tetrahydrofuran or 2-methyltetrahydrofuran to the suspension for a contact reaction, the reaction solution is subjected to solid-liquid separation. The liquid phase is precipitated with diethyl ether to obtain precipitate A; the solid phase is slurried twice with dimethyl sulfoxide, the dimethyl sulfoxide phase is collected and mixed with diethyl ether, and then ethanol is added for precipitation to obtain precipitate B.
[0010] After dissolving precipitate A and precipitate B in methanol, diethyl ether was added for precipitation. The precipitates were then washed and dried sequentially to obtain sodium methacryloyl taurate monomer, whose chemical structure is shown in formula (). As shown in the image:
[0011]
[0012] ( ).
[0013] According to the disclosure of the first aspect, the molar ratio of taurine, sodium hydroxide, sodium / potassium salt containing hydrogen phosphate or bicarbonate and methacryloyl chloride is 1:(0.5~2.5):(0.7~4):(0.8~3).
[0014] According to the disclosure of the first aspect, the sodium / potassium salt containing hydrogen phosphate or bicarbonate is selected from at least one of disodium hydrogen phosphate, dipotassium hydrogen phosphate, sodium bicarbonate, and potassium bicarbonate.
[0015] According to the disclosure of the first aspect, when the tetrahydrofuran or 2-methyltetrahydrofuran solution of methacryloyl chloride is added to the suspension for contact reaction, the addition rate is 1~1.5 mL / min, wherein the molar amount of the tetrahydrofuran or 2-methyltetrahydrofuran solution of methacryloyl chloride is 1.1 mol / 30 mL.
[0016] The second aspect of this application also discloses a taurine-containing polymer derived from the sodium methacryloyl taurate monomer described above, the taurine-containing polymer comprising polymethacryloyl taurate and a methacryloyl taurate-methacrylic acid copolymer.
[0017] The chemical structure of the polymethacryloyl taurate is as follows: ( )or( As shown in the figure;
[0018] ( ) ( )
[0019] Where n1 is 10~50; n2 is 400~4000;
[0020] The methacryloyl taurate-methacrylic acid copolymer is synthesized by copolymerization of methacrylic acid monomer and sodium methacryloyl taurate monomer prepared by the preparation method described in this application. The chemical structure of the methacryloyl taurate-methacrylic acid copolymer is as follows: ( )or( As shown in the figure;
[0021]
[0022] ( ) ( )
[0023] Where n is 400~4000 and m is 400~4000.
[0024] A third aspect of this application also discloses a method for preparing the taurine-containing polymer described herein by RAFT controlled polymerization, comprising:
[0025] The monomer, azo RAFT reagent, and dithiobenzoic acid ester RAFT initiator were dissolved in a methanol / water mixture. After a freeze-evacuation-melt cycle, the RAFT polymerization reaction was carried out in a nitrogen atmosphere. After the reaction was completed, the product solution was precipitated with tetrahydrofuran, the precipitate was collected and dissolved in methanol, precipitated again with tetrahydrofuran and the precipitate was collected. Finally, the precipitate was washed and dried to obtain the taurine polymer.
[0026] Wherein, the monomer is the sodium methacryloyl taurate monomer, or a mixture of the sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide;
[0027] When the monomer is sodium methacryloyl taurate, the resulting taurate polymer has the following chemical structure ( The polymethacryloyl taurate shown is shown in the figure; when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the resulting taurate polymer has the chemical structure ( The methacryloyl taurate-methacrylic acid copolymer shown is shown in the figure.
[0028] According to the disclosure of the third aspect, the temperature of the RAFT polymerization reaction is 70~75°C and the time is 24~48h;
[0029] And / or, the molar ratio of the azo RAFT reagent to the dithiobenzoate RAFT initiator is 1:5;
[0030] And / or, when the monomer is sodium methacryloyltaurate monomer, the molar ratio of sodium methacryloyltaurate monomer to the dithiobenzoate RAFT initiator is n1 / n2:1, and the mass fraction of sodium methacryloyltaurate monomer is 10~25wt% of the mixture;
[0031] And / or, when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the molar ratio of sodium hydroxide to methacrylic acid monomer is 0.5:1, and the molar ratio of the total molar number of sodium methacryloyl taurate monomer and methacrylic acid monomer to the molar ratio of the dithiobenzoate RAFT initiator is (n+m):1.
[0032] A fourth aspect of this application also discloses a method for preparing the taurine-containing polymer described in this application by persulfate-initiated polymerization, comprising:
[0033] The monomer and persulfate initiator were dissolved in a methanol / water mixture, and the persulfate-initiated polymerization reaction was carried out under a nitrogen atmosphere. The product solution was precipitated with tetrahydrofuran, the precipitate was collected and dissolved in methanol, and then precipitated with tetrahydrofuran again and the precipitate was collected. Finally, the precipitate was washed and dried to obtain the taurine polymer.
[0034] Wherein, the monomer is sodium methacryloyl taurate monomer, or a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide;
[0035] When the monomer is sodium methacryloyl taurate, the resulting taurate polymer has the following chemical structure ( The polymethacryloyl taurate shown is shown in the figure; when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the resulting taurate polymer has the chemical structure ( The methacryloyl taurate-methacrylic acid copolymer shown is shown in the figure.
[0036] According to the disclosure of aspect 4, the temperature for the persulfate-initiated polymerization reaction is 70-75°C, and the time is 24-48 hours;
[0037] And / or, the persulfate initiator is one of K2S2O8, Na2S2O8 or (NH4)2S2O8;
[0038] And / or, when the monomer is sodium methacryloyltaurate, the mass ratio of sodium methacryloyltaurate to persulfate initiator is 100:0.2~2, and the mass fraction of sodium methacryloyltaurate monomer is 10~25 wt% of the mixture;
[0039] And / or, when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the molar ratio of sodium hydroxide to methacrylic acid monomer is 0.5:1, and the mass ratio of the total mass of the sodium methacryloyl taurate monomer and the methacrylic acid monomer to the mass of the persulfate initiator is 100:0.2~2.
[0040] The fifth aspect of this application also discloses the application of the taurine-containing polymer described in this application, specifically the use of the taurine-containing polymer in biomedical materials, cosmetic and personal care materials, sensors, water treatment materials, and antifouling coating materials, etc.
[0041] Compared with the prior art, the advantages or beneficial effects of this application include at least:
[0042] The preparation method provided in this application involves adding an aqueous sodium taurate system to tetrahydrofuran or 2-methyltetrahydrofuran, and then adding sodium / potassium salts containing hydrogen phosphate or bicarbonate to form a suspension. This suspension is then reacted with a tetrahydrofuran or 2-methyltetrahydrofuran solution of methacryloyl chloride. Firstly, this method successfully replaces the traditional aqueous-organic phase reaction system with an organic-solid phase reaction system, effectively reducing the free water content in the reaction system and minimizing the hydrolysis side reactions of small molecule acryloyl chloride. Secondly, by selecting sodium / potassium salts containing hydrogen phosphate or bicarbonate as taurine amino activators, this method ensures the good nucleophilic activity of taurine to promote the efficient synthesis of sodium methacryloyl taurate monomer, while also absorbing the reaction byproduct hydrogen halide, further inhibiting the hydrolysis side reactions of acryloyl chloride. Based on these combined technologies, the yield and purity of taurine monomers synthesized by the acryloyl chloride method are synergistically improved. Furthermore, this method has the advantages of a simple process and ease of large-scale production, laying the foundation for the industrial application of taurine-containing polymers. Attached Figure Description
[0043] To more clearly illustrate the technical solutions of the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments recorded in this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.
[0044] Figure 1 The 1H NMR spectrum of sodium methacryloyl taurate monomer prepared in Example 1 of this application;
[0045] Figure 2 The 1H NMR spectrum of polymethacryloyl taurate prepared by the RAFT controlled polymerization method in Example 6 of this application is shown.
[0046] Figure 3The above is the 1H NMR spectrum of the methacryloyl taurate-methacrylic acid copolymer prepared by the RAFT controlled polymerization method in Example 7 of this application;
[0047] Figure 4 The infrared spectrum of polymethacryloyl taurate prepared by persulfate-initiated polymerization in Example 8 of this application is shown.
[0048] Figure 5 The infrared spectrum of the methacryloyl taurate-methacrylic acid copolymer prepared by persulfate-initiated polymerization in Example 9 of this application is shown. Detailed Implementation
[0049] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some, not all, of the embodiments of this application. All other embodiments obtained by those skilled in the art based on the embodiments described in this application without creative effort are within the scope of protection of this application.
[0050] In the following description of this application, the term "and / or" is used to describe the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, B existing alone, and A and B existing simultaneously. Here, A and B can be singular or plural; the symbol " / " means "or".
[0051] In the following description of this application, the term "at least one" means one or more, and "more than one" means two or more. "At least one of the following" or similar expressions mean any combination of such items, including any combination of single or multiple items. For example, "at least one of A, B or C" or "at least one of A, B and C" can mean any one of A, B, and C, or A+B, or A+C, or B+C, or A+B+C, where A, B, and C can be single or multiple.
[0052] In the following description of this application, the sequence of numbers does not imply the order of execution. Some or all steps may be executed in parallel or sequentially. The execution order of each process should be specifically determined by its function and internal logic, and does not constitute any limitation on the execution process of this embodiment.
[0053] In the following description of this application, the numerical range should be understood to also specifically disclose each intermediate value between the upper and lower limits of the range. Any intermediate value within a stated range, as well as any other stated value or each smaller range between intermediate values within a stated range, are also included in this embodiment, and the upper and lower limits of the smaller ranges may be independently included or excluded from the range.
[0054] Unless otherwise stated, the technical / scientific terms used in this application have the meanings commonly understood by one of ordinary skill in the art. While this application describes only preferred materials and methods, similar or equivalent methods and materials may be used in specific embodiments or test cases. All references to this application are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this application shall prevail.
[0055] To address the issue of low yield in existing acyl chloride methods for synthesizing taurine monomers, this application provides a method for preparing sodium methacryloyl taurate monomer in aspect 1, preferably comprising steps S1 to S3:
[0056] S1: After reacting taurine with sodium hydroxide in water, add the reaction solution to tetrahydrofuran or 2-methyltetrahydrofuran, and then add sodium / potassium salts containing hydrogen phosphate or bicarbonate to prepare a suspension.
[0057] S2: After adding a solution of methacryloyl chloride in tetrahydrofuran or 2-methyltetrahydrofuran to the suspension for a contact reaction, the reaction solution is subjected to solid-liquid separation. The liquid phase is precipitated with diethyl ether to obtain precipitate A; the solid phase is slurried twice with dimethyl sulfoxide, the dimethyl sulfoxide phase is collected and mixed with diethyl ether, and then ethanol is added for precipitation to obtain precipitate B.
[0058] S3: After dissolving precipitate A and precipitate B in methanol, diethyl ether is added for precipitation. The precipitates are then washed and dried sequentially to obtain sodium methacryloyl taurate monomer, whose chemical structure is shown in formula (). As shown in the image:
[0059]
[0060] ( ).
[0061] This application embodiment involves directly adding an aqueous sodium taurine system to tetrahydrofuran or 2-methyltetrahydrofuran, and then adding sodium / potassium salts containing hydrogen phosphate or bicarbonate to form a suspension. This suspension is then reacted with a tetrahydrofuran or 2-methyltetrahydrofuran solution of methacryloyl chloride. Firstly, the selective extraction capability of tetrahydrofuran or 2-methyltetrahydrofuran on the aqueous phase allows for efficient transfer of the aqueous phase from the sodium taurine system to the organic phase of tetrahydrofuran or 2-methyltetrahydrofuran. This reconstructs the reaction system from a traditional aqueous-organic two-phase system to an organic-solid two-phase system, fundamentally reducing the reaction between small molecule acryloyl chloride and water. The first step involves contact, which significantly reduces the side reactions of hydrolysis of small molecule acyl chlorides. The second step involves introducing sodium / potassium salts containing hydrogen phosphate or bicarbonate into the organic-solid two-phase system formed above. These salts can act as specific activators for taurine amino groups, ensuring good nucleophilic activity of taurine to promote the efficient synthesis of sodium methacryloyl taurate monomer. They can also absorb hydrogen halide byproducts of the reaction, further inhibiting the side reactions of hydrolysis of acyl chlorides. Based on the synergistic effect of the above two technologies, the yield and purity of taurine monomers synthesized by the acyl chloride method are greatly improved, resulting in an average yield of sodium methacryloyl taurate monomers of over 42%, while the NMR purity also reaches over 90.2%. Furthermore, the preparation method of this application is simple, requiring only the construction of a suspension system using tetrahydrofuran or 2-methyltetrahydrofuran and sodium / potassium salts containing hydrogen phosphate or bicarbonate, followed by contact reaction with a solution of methacryloyl chloride in tetrahydrofuran or 2-methyltetrahydrofuran. This eliminates the need for complex and cumbersome intermediate processing steps, and the reaction system is stable with mild and controllable reaction conditions, further reducing the technical difficulty and cost of large-scale production. Combining process advantages with high yield and high purity products, this method effectively promotes the industrialization of taurine-containing polymers and possesses significant industrial application value.
[0062] In possible public examples, the molar ratio of taurine, sodium hydroxide, disodium hydrogen phosphate, and methacrylamide chloride described in this application is 1:(0.5~2.5):(0.7~4):(0.8~3). The molar ratio of 1:1:1.1:1.1 is chosen as an example in this application because this ratio yields the highest amount and purity of sodium methacrylamide taurate monomer, providing a comprehensive and intuitive verification of the technical effect and facilitating understanding by those skilled in the art. However, this does not constitute any limitation on the scope of protection of this application. Any other ratio falling within the above range is within the scope of protection of this application, and will not be listed individually.
[0063] In possible public examples, the sodium / potassium salt containing hydrogen phosphate or bicarbonate is preferably at least one of disodium hydrogen phosphate (Na2HPO4), dipotassium hydrogen phosphate (K2HPO4), sodium bicarbonate (NaHCO3), and potassium bicarbonate (KHCO3).
[0064] In possible public examples, when the tetrahydrofuran or 2-methyltetrahydrofuran solution of methacryloyl chloride is added to the suspension for contact reaction as described in this application, the addition rate is preferably 1~1.5 mL / min, wherein the molar amount of the tetrahydrofuran or 2-methyltetrahydrofuran solution of methacryloyl chloride is 1.1 mol / 30 mL.
[0065] In a second aspect, embodiments of this application also provide a taurine-containing polymer derived from the sodium methacryloyl taurate monomer described above, wherein the taurine-containing polymer comprises polymethacryloyl taurate and a methacryloyl taurate-methacrylic acid copolymer. The polymethacryloyl taurate is polymerized from sodium methacryloyl taurate monomer prepared by the preparation method described above, and its chemical structure is as follows: ( )or( As shown in the image:
[0066] The chemical structure of the polymethacryloyl taurate is as follows: ( )or( As shown in the figure;
[0067]
[0068] ( ) ( )
[0069] Where n1 is 10~50; n2 is 400~4000;
[0070] The methacryloyl taurate-methacrylic acid copolymer is synthesized by polymerization of methacrylic acid monomer and sodium methacryloyl taurate monomer prepared by the preparation method described above, and its chemical structure is as follows: ( )or( As shown in the figure;
[0071] ( ) ( )
[0072] Where n is 400~4000 and m is 400~4000.
[0073] A third aspect of this application also discloses a method for preparing the taurine-containing polymer described herein by RAFT controlled polymerization, comprising:
[0074] The monomer, azo RAFT reagent, and dithiobenzoic acid ester RAFT initiator were dissolved in a methanol / water mixture. After a freeze-evacuation-melt cycle, the RAFT polymerization reaction was carried out in a nitrogen atmosphere. After the reaction was completed, the product solution was precipitated with tetrahydrofuran, the precipitate was collected and dissolved in methanol, precipitated again with tetrahydrofuran and the precipitate was collected. Finally, the precipitate was washed and dried to obtain the taurine polymer.
[0075] Wherein, the monomer is the sodium methacryloyl taurate monomer, or a mixture of the sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide;
[0076] When the monomer is sodium methacryloyl taurate, the resulting taurate polymer has the following chemical structure ( The polymethacryloyl taurate shown is shown in the figure; when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the resulting taurate polymer has the chemical structure ( The methacryloyl taurate-methacrylic acid copolymer shown is shown in the figure.
[0077] In possible public examples, the RAFT polymerization reaction is preferably carried out at a temperature of 70-75°C for 24-48 hours.
[0078] In a possible public example, the molar ratio of the azo RAFT reagent to the dithiobenzoate RAFT initiator is 1:5.
[0079] In possible disclosed examples, when the monomer is sodium methacryloyltaurate monomer, the molar ratio of the sodium methacryloyltaurate monomer to the dithiobenzoate RAFT initiator is n1 / n2:1, and the mass fraction of the sodium methacryloyltaurate monomer is 10~25wt% of the mixture;
[0080] In a possible disclosed example, when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the molar ratio of sodium hydroxide to methacrylic acid monomer is 0.5:1, and the molar ratio of the total molar number of sodium methacryloyl taurate monomer and methacrylic acid monomer to the molar ratio of the dithiobenzoate RAFT initiator is (n+m):1.
[0081] A fourth aspect of this application also discloses a method for preparing the taurine-containing polymer described in this application by persulfate-initiated polymerization, comprising:
[0082] The monomer and persulfate initiator were dissolved in a methanol / water mixture, and the persulfate-initiated polymerization reaction was carried out under a nitrogen atmosphere. The product solution was precipitated with tetrahydrofuran, the precipitate was collected and dissolved in methanol, and then precipitated with tetrahydrofuran again and the precipitate was collected. Finally, the precipitate was washed and dried to obtain the taurine polymer.
[0083] Wherein, the monomer is sodium methacryloyl taurate monomer, or a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide;
[0084] When the monomer is sodium methacryloyl taurate, the resulting taurate polymer has the following chemical structure ( The polymethacryloyl taurate shown is shown in the figure; when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the resulting taurate polymer has the chemical structure ( The methacryloyl taurate-methacrylic acid copolymer shown is shown in the figure.
[0085] In possible public examples, the preferred temperature for the persulfate-initiated polymerization reaction is 70-75°C, and the preferred time is 24-48 hours.
[0086] In possible disclosed examples, the persulfate initiator is one of K2S2O8, Na2S2O8 or (NH4)2S2O8;
[0087] In possible disclosed examples, when the monomer is sodium methacryloyltaurate, the mass ratio of sodium methacryloyltaurate to persulfate initiator is 100:0.2~2, and the mass fraction of sodium methacryloyltaurate monomer is 10~25 wt% of the mixture;
[0088] In a possible disclosed example, when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the molar ratio of sodium hydroxide to methacrylic acid monomer is 0.5:1, and the mass ratio of the total mass of the sodium methacryloyl taurate monomer and the methacrylic acid monomer to the mass of the persulfate initiator is 100:0.2~2.
[0089] The fifth aspect of this application also discloses the applications of the taurine-containing polymer described herein. Given that the taurine-containing polymer possesses strong hydrophilicity, good biocompatibility and ionization ability, can electrostatically interact with biomolecules, and can copolymerize or crosslink with other monomers to form hydrogels, it can be used in multiple fields such as biomedical materials, cosmetic and skincare materials, sensors, water treatment materials, or antifouling coating materials. Specifically, firstly, based on the high hydrophilicity, oxygen permeability, excellent moisturizing properties (reducing dry eyes), and potential anti-protein adsorption ability (reducing lens dirt) of the taurine-containing polymer described herein, and its potential to mimic tear components, it can be used to prepare biomedical materials including soft contact lenses (especially silicone hydrogel lenses), artificial corneas, intraocular implant coatings, eye drop carriers, hydrogel scaffolds, and wound dressings, and can also be used to manufacture high-end moisturizers, skin feel modifiers, antistatic agents, stabilizers, or thickeners in cosmetics and skincare materials; secondly, based on the sulfonic acid groups of the taurine-containing polymer interacting with specific cations (such as H... + Na + K + Ca 2+ It is sensitive to heavy metal ions and can effectively adsorb cationic heavy metal pollutants (such as Pb) in aqueous solutions. 2+ Cd 2+ Cu 2+ The characteristics of taurine-containing polymers can be used to develop electrochemical / optical ion sensors for detecting proteins, DNA, glucose, etc., and can also be made into membranes, resins or hydrogels for wastewater treatment. Fourth, based on the strong hydrophilicity of taurine-containing polymers, which can form hydration layers, it is expected to be used in medical devices (such as catheters), marine antifouling (inhibiting biofouling), membrane separation (reducing membrane fouling) and other fields as a coating material against protein, bacteria or biofouling.
[0090] The technical solution of this application will be further described below with reference to specific embodiments.
[0091] Example 1
[0092] This example provides a method for preparing sodium methacryloyl taurate monomer, the specific steps of which include:
[0093] S1: After reacting 1 mol of taurine and 1 mol of NaOH in 5 mL of water, the reaction solution is directly added to tetrahydrofuran (THF, THF diluted to 30 mL), and then 1.1 mol of disodium hydrogen phosphate is added in batches to prepare a suspension.
[0094] S2: Dissolve 1.1 mol of methacryloyl chloride in 30 mL of tetrahydrofuran (THF) to prepare a solution, and add the solution to the suspension at a rate of 1.5 mL / min using a constant pressure funnel. Let the mixture stand at room temperature to react and obtain an intermediate solution.
[0095] S3: The intermediate liquid is centrifuged and the resulting liquid phase is precipitated with diethyl ether to collect precipitate A; the resulting solid phase is pulped twice with DMSO and centrifuged to separate the DMSO phase. The DMSO phase is placed in a beaker and diethyl ether equivalent to 5 times its volume is added. The mixture is stirred vigorously and then ethanol is slowly added until the DMSO phase just disappears. The precipitate is collected by filtration and then washed with a mixture of diethyl ether and ethanol to collect precipitate B.
[0096] S4: After dissolving precipitates A and B in methanol, the solution was volatilized until it became turbid and then precipitated with diethyl ether. The solid phase was separated by centrifugation and dried under vacuum at room temperature for 5 hours to obtain sodium methacryloyl taurate monomer powder.
[0097] Example 2
[0098] This example provides a method for preparing sodium methacryloyl taurate monomer, the specific steps of which include:
[0099] S1: After reacting 1 mol of taurine and 1 mol of NaOH in 5 mL of water, the reaction solution was directly added to 2-methyltetrahydrofuran (2-Me-THF, 2-Me-THF diluted to 30 mL), and then 1.1 mol of disodium hydrogen phosphate was added in batches to prepare a suspension.
[0100] S2: Dissolve 1.1 mol of methacrylamide chloride in 30 mL of 2-methyltetrahydrofuran (2-Me-THF) to prepare a solution, and add the solution to the suspension at a rate of 1.5 mL / min using a constant pressure funnel. Let the mixture stand at room temperature to react and obtain an intermediate solution.
[0101] S3: The intermediate liquid is centrifuged and the resulting liquid phase is precipitated with diethyl ether to collect precipitate A; the resulting solid phase is pulped twice with DMSO and centrifuged to separate the DMSO phase. The DMSO phase is placed in a beaker and diethyl ether equivalent to 5 times its volume is added. The mixture is stirred vigorously and then ethanol is slowly added until the DMSO phase just disappears. The precipitate is collected by filtration and then washed with a mixture of diethyl ether and ethanol to collect precipitate B.
[0102] S4: After dissolving precipitates A and B in methanol, the solution was volatilized until it became turbid and then precipitated with diethyl ether. The solid phase was separated by centrifugation and dried under vacuum at room temperature for 5 hours to obtain sodium methacryloyl taurate monomer powder.
[0103] Example 3
[0104] This example provides a method for preparing sodium methacryloyl taurate monomer, the specific steps of which include:
[0105] S1: After reacting 1 mol of taurine and 1 mol of NaOH in 5 mL of water, the reaction solution was directly added to tetrahydrofuran (THF, diluted to 30 mL), and then 1.1 mol of dipotassium hydrogen phosphate was added in batches to prepare a suspension.
[0106] S2: Dissolve 1.1 mol of methacryloyl chloride in 30 mL of tetrahydrofuran (THF) to prepare a solution, and add the solution to the suspension at a rate of 1.5 mL / min using a constant pressure funnel. Let the mixture stand at room temperature to react and obtain an intermediate solution.
[0107] S3: The intermediate liquid is centrifuged and the resulting liquid phase is precipitated with diethyl ether to collect precipitate A; the resulting solid phase is pulped twice with DMSO and centrifuged to separate the DMSO phase. The DMSO phase is placed in a beaker and diethyl ether equivalent to 5 times its volume is added. The mixture is stirred vigorously and then ethanol is slowly added until the DMSO phase just disappears. The precipitate is collected by filtration and then washed with a mixture of diethyl ether and ethanol to collect precipitate B.
[0108] S4: After dissolving precipitates A and B in methanol, the solution was volatilized until it became turbid and then precipitated with diethyl ether. The solid phase was separated by centrifugation and dried under vacuum at room temperature for 5 hours to obtain sodium methacryloyl taurate monomer powder.
[0109] Example 4
[0110] This example provides a method for preparing sodium methacryloyl taurate monomer, the specific steps of which include:
[0111] S1: After reacting 1 mol of taurine and 1 mol of NaOH in 5 mL of water, the reaction solution is directly added to tetrahydrofuran (THF, diluted to 30 mL), and then 1.1 mol of sodium bicarbonate is added in batches to prepare a suspension.
[0112] S2: Dissolve 1.1 mol of methacryloyl chloride in 30 mL of tetrahydrofuran (THF) to prepare a solution, and add the solution to the suspension at a rate of 1.5 mL / min using a constant pressure funnel. Let the mixture stand at room temperature to react and obtain an intermediate solution.
[0113] S3: The intermediate liquid is centrifuged and the resulting liquid phase is precipitated with diethyl ether to collect precipitate A; the resulting solid phase is pulped twice with DMSO and centrifuged to separate the DMSO phase. The DMSO phase is placed in a beaker and diethyl ether equivalent to 5 times its volume is added. The mixture is stirred vigorously and then ethanol is slowly added until the DMSO phase just disappears. The precipitate is collected by filtration and then washed with a mixture of diethyl ether and ethanol to collect precipitate B.
[0114] S4: After dissolving precipitates A and B in methanol, the solution was volatilized until it became turbid and then precipitated with diethyl ether. The solid phase was separated by centrifugation and dried under vacuum at room temperature for 5 hours to obtain sodium methacryloyl taurate monomer powder.
[0115] Example 5
[0116] This example provides a method for preparing sodium methacryloyl taurate monomer, the specific steps of which include:
[0117] S1: After reacting 1 mol of taurine and 1 mol of NaOH in 5 mL of water, the reaction solution is directly added to tetrahydrofuran (THF, diluted to 30 mL), and then 1.1 mol of potassium bicarbonate is added in batches to prepare a suspension.
[0118] S2: Dissolve 1.1 mol of methacryloyl chloride in 30 mL of tetrahydrofuran (THF) to prepare a solution, and add the solution to the suspension at a rate of 1.5 mL / min using a constant pressure funnel. Let the mixture stand at room temperature to react and obtain an intermediate solution.
[0119] S3: The intermediate liquid is centrifuged and the resulting liquid phase is precipitated with diethyl ether to collect precipitate A; the resulting solid phase is pulped twice with DMSO and centrifuged to separate the DMSO phase. The DMSO phase is placed in a beaker and diethyl ether equivalent to 5 times its volume is added. The mixture is stirred vigorously and then ethanol is slowly added until the DMSO phase just disappears. The precipitate is collected by filtration and then washed with a mixture of diethyl ether and ethanol to collect precipitate B.
[0120] S4: After dissolving precipitates A and B in methanol, the solution was volatilized until it became turbid and then precipitated with diethyl ether. The solid phase was separated by centrifugation and dried under vacuum at room temperature for 5 hours to obtain sodium methacryloyl taurate monomer powder.
[0121] To illustrate the practical effects of the preparation methods in Examples 1-5 above, this application also provides Comparative Examples 1-10.
[0122] Comparative Example 1
[0123] This comparative example provides a method for preparing sodium methacryloyltaurate monomer, which differs from Example 1 only in that 1,4-dioxane is used instead of tetrahydrofuran (THF), and is otherwise identical.
[0124] Comparative Example 2
[0125] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that chloroform is used instead of tetrahydrofuran (THF), otherwise it is exactly the same.
[0126] Comparative Example 3
[0127] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that toluene is used instead of tetrahydrofuran (THF), otherwise it is exactly the same.
[0128] Comparative Example 4
[0129] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that petroleum ether is used instead of tetrahydrofuran (THF), otherwise it is exactly the same.
[0130] Comparative Example 5
[0131] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that hexane is used instead of tetrahydrofuran (THF), otherwise it is exactly the same.
[0132] Comparative Example 6
[0133] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that sodium carbonate is used instead of disodium hydrogen phosphate; otherwise, they are completely identical.
[0134] Comparative Example 7
[0135] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that potassium carbonate is used instead of disodium hydrogen phosphate; otherwise, they are completely identical.
[0136] Comparative Example 8
[0137] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that sodium hydroxide is used instead of disodium hydrogen phosphate; otherwise, they are completely identical.
[0138] Comparative Example 9
[0139] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that triethylamine is used instead of disodium hydrogen phosphate; otherwise, they are identical.
[0140] Comparative Example 10
[0141] This comparative example provides a method for preparing sodium methacryloyl taurate monomer, which differs from Example 1 only in that pyridine is used instead of disodium hydrogen phosphate; otherwise, they are completely identical.
[0142] The average yield and NMR purity of sodium methacryloyl taurate monomers prepared in Examples 1-5 and Comparative Examples 1-10 were calculated, and the results are recorded in Table 1.
[0143] Table 1: Average yield and NMR purity of sodium methacryloyltaurate monomer
[0144]
[0145] As shown in Table 1, the average yield and NMR purity of Examples 1-5 are higher than those of Comparative Examples 1-8. Although the average yield of Comparative Examples 9-10 is relatively high, their NMR purity is extremely low. Therefore, considering both the average yield and NMR purity, the preparation method provided in this application has the effect of significantly increasing the yield and NMR purity of sodium methacryloyl taurate monomer.
[0146] in, Figure 1 The 1H NMR spectrum of sodium methacryloyl taurate monomer prepared in Example 1 (solvent: heavy water, 400MHz).
[0147] according to Figure 1 It is known that this application has successfully prepared sodium methacryloyltaurate monomer, the chemical structure of which is as follows:
[0148] .
[0149] Example 6
[0150] This example provides a method for preparing polymethacryloyl taurate via RAFT controlled polymerization, the specific steps of which include:
[0151] S1: 5 mol of sodium methacryloyltaurate monomer, 0.02 mol of 4,4'-azobis(4-cyanopentanoic acid) and 0.1 mol of 4-cyanopentanoic acid dithiobenzoic acid were dissolved in a methanol / water mixture (volume ratio 1:1). The mixture was subjected to three freeze-evacuation-melt cycles and then reacted in a nitrogen atmosphere at 70°C for 24 h. The mass fraction of sodium methacryloyltaurate monomer in the mixture was 15%.
[0152] S2: After the reaction is complete, the polymer solution is poured into 10 times its volume of THF for precipitation, and the precipitate is collected by filtration. The precipitate is dissolved in methanol and precipitated again in THF. The precipitate is collected, washed three times with THF, and then washed with ether to remove THF. Then it is vacuum dried at room temperature for 12 h to obtain a light pink polymer powder, namely polymethacryloyl taurate with a degree of polymerization of 50.
[0153] in, Figure 2 The above is the 1H NMR spectrum of polymethacryloyl taurate prepared by the RAFT controlled polymerization method (solvent: heavy water, 400MHz).
[0154] according to Figure 2 It is evident that this application successfully prepared polymethacryloyl taurate, the chemical structure of which is as follows:
[0155] .
[0156] Example 7
[0157] This example provides a method for preparing methacryloyl taurate-methacrylic acid copolymers via RAFT controlled polymerization, including the following steps:
[0158] S1: Mix 2.5 mol of methacrylic acid monomer with 1.25 mol of sodium hydroxide until homogeneous to obtain a mixture;
[0159] S2: 7.5 mol sodium methacryloyl taurate monomer, a mixture, 0.02 mol 4,4'-azobis(4-cyanopentanoic acid) and 0.1 mol 4-cyanopentanoic acid dithiobenzoic acid were dissolved in a methanol / water mixture (volume ratio 1:1). The mixture was subjected to three freeze-evacuation-melt cycles, and then reacted at 70°C for 24 h under a nitrogen atmosphere. The total mass fraction of sodium methacryloyl taurate monomer and methacrylic acid monomer in the mixture was 15%.
[0160] S3: After the reaction is complete, the polymer solution is poured into 10 times its volume of THF for precipitation, and the precipitate is collected by filtration. The precipitate is dissolved in methanol and precipitated again in THF. The precipitate is collected, washed three times with THF, and then washed with ether to remove THF. Then, it is vacuum dried at room temperature for 12 h to obtain a light pink polymer powder, which is a methacryloyl taurate-methacrylic acid copolymer with a degree of polymerization of 100 and a molar ratio of carboxyl groups to taurate groups of 1:3.
[0161] in, Figure 3 The 1H NMR spectrum of the methacryloyl taurate-methacrylic acid copolymer prepared by the RAFT controlled polymerization method (solvent: heavy water, 400 MHz) is shown.
[0162] according to Figure 3 It is evident that this application successfully prepared a methacryloyl taurate-methacrylic acid copolymer, the chemical structure of which is as follows:
[0163] .
[0164] Example 8
[0165] This example provides a method for preparing polymethacryloyl taurate via persulfate-initiated polymerization, the specific steps of which include:
[0166] A solution was prepared by dissolving 10 mol of sodium methacryloyl taurate monomer and 0.05 mol of potassium persulfate in water, and the solution was reacted at 75°C for 24 h under a nitrogen atmosphere. After the reaction, the polymer solution was poured into 10 times its volume of THF for precipitation, and the precipitate was collected by filtration. The precipitate was dissolved in methanol and precipitated again in THF. The precipitate was collected, washed three times with THF, and then washed with diethyl ether to remove THF. The precipitate was then dried under vacuum at room temperature for 12 h to obtain a white polymer powder, which is polymethacryloyl taurate. The mass concentration of sodium methacryloyl taurate monomer in the solution was 25%.
[0167] in, Figure 4 The infrared spectrum of polymethacryloyl taurate prepared by persulfate-initiated polymerization is shown.
[0168] according to Figure 4 The presence of amide bonds and sulfonic acid structures on the polymer indicates that polymethacryloyl taurate was successfully synthesized.
[0169] Example 9
[0170] This example provides a method for preparing methacryloyl taurate-methacrylic acid copolymers via persulfate-initiated polymerization, the specific steps of which include:
[0171] S1: Mix 2.5 mol of methacrylic acid monomer with 1.25 mmol of sodium hydroxide to form a mixture;
[0172] S2: Dissolve 7.5 mmol of sodium methacryloyl taurate monomer, the mixture, and 0.05 mol of potassium persulfate in a mixture of methanol and water at a volume ratio of 1:1, and react at 75 °C for 24 h under a nitrogen atmosphere. The total mass concentration of sodium methacryloyl taurate monomer and methacrylic acid monomer in the mixture is 25%.
[0173] S3: After the reaction is complete, the polymer solution is poured into 10 times its volume of THF for precipitation, and the precipitate is collected by filtration. The precipitate is dissolved in methanol and precipitated again in THF. The precipitate is collected, washed three times with THF, and then washed with ether to remove THF. Then it is dried under vacuum at room temperature for 12 h to obtain a white polymer powder, namely methacryloyl taurate-methacrylic acid copolymer.
[0174] in, Figure 5 The infrared spectrum of the methacryloyl taurate-methacrylic acid copolymer prepared by persulfate-initiated polymerization is shown.
[0175] according to Figure 5 The presence of amide bonds, carboxyl groups, and sulfonic acid structures on the polymer indicates that the copolymer was successfully synthesized.
[0176] The various embodiments in this application are described in a progressive manner. The same or similar parts between the various embodiments can be referred to each other. Each embodiment focuses on describing the differences from other embodiments.
[0177] The above embodiments are only used to illustrate the technical solutions of this application, and are not intended to limit this application. Although this application has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features therein. Such modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of this application.
Claims
1. A method for preparing sodium methacryloyltaurate monomer, characterized in that, Include: After reacting taurine with sodium hydroxide in water, the reaction solution is added to tetrahydrofuran or 2-methyltetrahydrofuran, and then sodium / potassium salts containing hydrogen phosphate or bicarbonate are added to prepare a suspension. After adding a solution of methacryloyl chloride in tetrahydrofuran or 2-methyltetrahydrofuran to the suspension for a contact reaction, the reaction solution is subjected to solid-liquid separation. The liquid phase is precipitated with diethyl ether to obtain precipitate A; the solid phase is slurried twice with dimethyl sulfoxide, the dimethyl sulfoxide phase is collected and mixed with diethyl ether, and then ethanol is added for precipitation to obtain precipitate B. After dissolving precipitate A and precipitate B in methanol, diethyl ether was added for precipitation. The precipitates were then washed and dried sequentially to obtain sodium methacryloyl taurate monomer, the chemical structure of which is shown in formula (i). (i)。 2. The preparation method according to claim 1, characterized in that, The molar ratio of taurine, sodium hydroxide, sodium / potassium salts containing hydrogen phosphate or bicarbonate and methacryloyl chloride is 1:(0.5~2.5):(0.7~4):(0.8~3).
3. The preparation method according to claim 1, characterized in that, The sodium / potassium salt containing hydrogen phosphate or bicarbonate is selected from at least one of disodium hydrogen phosphate, dipotassium hydrogen phosphate, sodium bicarbonate, and potassium bicarbonate.
4. The preparation method according to claim 1, characterized in that, When adding a solution of methacryloyl chloride in tetrahydrofuran or 2-methyltetrahydrofuran to the suspension for a contact reaction, the addition rate is 1~1.5 mL / min, wherein the molar amount of the solution of methacryloyl chloride in tetrahydrofuran or 2-methyltetrahydrofuran is 1.1 mol / 30 mL.
5. A taurine-containing polymer, characterized in that, Contains polymethacryloyl taurate and methacryloyl taurate-methacrylic acid copolymer; The polymethacryloyl taurate is synthesized by self-polymerization of sodium methacryloyl taurate monomer prepared by any of the preparation methods described in claims 1 to 4; The chemical structure of the polymethacryloyl taurate is shown in formula (ii) or (iii); (ii) (iii) Where n1 is 10~50; n2 is 400~4000; The methacryloyl taurate-methacrylic acid copolymer is synthesized by copolymerizing sodium methacryloyl taurate monomer and methacrylic acid monomer prepared by any of the preparation methods described in claims 1 to 4; The chemical structure of the methacryloyl taurate-methacrylic acid copolymer is shown in formula (iv) or (v); (iv) (v) Where n is 400~4000 and m is 400~4000.
6. A method for preparing the taurine-containing polymer of claim 5 by RAFT controlled polymerization, characterized in that, Include: The monomer, azo RAFT reagent, and dithiobenzoic acid ester RAFT initiator were dissolved in a methanol / water mixture. After a freeze-evacuation-melt cycle, the RAFT polymerization reaction was carried out in a nitrogen atmosphere. After the reaction was completed, the product solution was precipitated with tetrahydrofuran, the precipitate was collected and dissolved in methanol, precipitated again with tetrahydrofuran and the precipitate was collected. Finally, the precipitate was washed and dried to obtain the taurine polymer. Wherein, the monomer is the sodium methacryloyl taurate monomer, or a mixture of the sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide; When the monomer is sodium methacryloyltaurate monomer, the resulting taurine polymer is polymethacryloyltaurate as shown in chemical structure (ii); when the monomer is a mixture of sodium methacryloyltaurate monomer and methacrylic acid monomer with sodium hydroxide, the resulting taurine polymer is methacryloyltaurate-methacrylic acid copolymer as shown in chemical structure (iv).
7. The method according to claim 6, characterized in that, The RAFT polymerization reaction is carried out at a temperature of 70-75°C for 24-48 hours. And / or, the molar ratio of the azo RAFT reagent to the dithiobenzoate RAFT initiator is 1:5; And / or, when the monomer is sodium methacryloyltaurate monomer, the molar ratio of sodium methacryloyltaurate monomer to the dithiobenzoate RAFT initiator is n1 / n2:1, and the mass fraction of sodium methacryloyltaurate monomer is 10~25wt% of the mixture; And / or, when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the molar ratio of sodium hydroxide to methacrylic acid monomer is 0.5:1, and the molar ratio of the total molar number of sodium methacryloyl taurate monomer and methacrylic acid monomer to the molar ratio of the dithiobenzoate RAFT initiator is (n+m):
1.
8. A method for preparing the taurine polymer of claim 4 by sulfate-initiated polymerization, characterized in that, Include: The monomer and persulfate initiator were dissolved in a methanol / water mixture, and the persulfate-initiated polymerization reaction was carried out under a nitrogen atmosphere. The product solution was precipitated with tetrahydrofuran, the precipitate was collected and dissolved in methanol, and then precipitated with tetrahydrofuran again and the precipitate was collected. Finally, the precipitate was washed and dried to obtain the taurine polymer. Wherein, the monomer is sodium methacryloyl taurate monomer, or a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide; When the monomer is sodium methacryloyltaurate monomer, the resulting taurine polymer is polymethacryloyltaurate as shown in chemical structure (iii); when the monomer is a mixture of sodium methacryloyltaurate monomer and methacrylic acid monomer with sodium hydroxide, the resulting taurine polymer is methacryloyltaurate-methacrylic acid copolymer as shown in chemical structure (v).
9. The method according to claim 8, characterized in that, The polymerization reaction initiated by persulfate is carried out at a temperature of 70-75°C for 24-48 hours. And / or, the persulfate initiator is one of K2S2O8, Na2S2O8 or (NH4)2S2O8; And / or, when the monomer is sodium methacryloyltaurate, the mass ratio of sodium methacryloyltaurate to persulfate initiator is 100:0.2~2, and the mass fraction of sodium methacryloyltaurate monomer is 10~25 wt% of the mixture; And / or, when the monomer is a mixture of sodium methacryloyl taurate monomer and methacrylic acid monomer with sodium hydroxide, the molar ratio of sodium hydroxide to methacrylic acid monomer is 0.5:1, and the mass ratio of the total mass of the sodium methacryloyl taurate monomer and the methacrylic acid monomer to the mass of the persulfate initiator is 100:0.2~2.
10. The application of the taurine-containing polymer of claim 4 in biomedical materials, cosmetic care materials, sensors, water treatment materials, and antifouling coating materials.