CN117069389A - Application of multifunctional silane coupling agent in surface modification of bioactive glass - Google Patents

Application of multifunctional silane coupling agent in surface modification of bioactive glass Download PDF

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CN117069389A
CN117069389A CN202311027220.9A CN202311027220A CN117069389A CN 117069389 A CN117069389 A CN 117069389A CN 202311027220 A CN202311027220 A CN 202311027220A CN 117069389 A CN117069389 A CN 117069389A
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coupling agent
silane coupling
bioactive glass
multifunctional silane
formula
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骆昱晖
李�杰
周子林
谭雪琪
贾雪梦
张田林
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Jiangsu Ocean University
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Abstract

The invention takes commercial 3-aminopropyl silane coupling agent, diallylamine polyether acrylate, alkylating agent, gamma-propane sultone or gamma-butyrolactone as raw materials, and prepares a multifunctional silane coupling agent with more than one quaternary ammonium cation, sulfobetaine or carboxyl betaine in a molecular structure through aza-Michael addition reaction and quaternary ammonium salt reaction, which is used for surface modification of bioactive glass, and obtains the effects of enhancing biocompatibility, antibacterial and bacteriostasis and hydrophilicity after the surface modification of the bioactive glass.

Description

Application of multifunctional silane coupling agent in surface modification of bioactive glass
Technical Field
The invention relates to application of a multifunctional silane coupling agent in surface modification of bioactive glass, in particular to application of the multifunctional silane coupling agent containing diallyl quaternary ammonium cations, sulfobetaines or carboxybetaines in a molecular structure in surface modification of bioactive glass, and belongs to the field of functional materials.
Technical Field
The bioactive glass is prepared from SiO 2 -CaO-P 2 O 5 -Na 2 The inorganic material composed of O quaternary chemical components mainly has biological activity mainly because alkaline earth metal and alkali metal ions connected by non-bridging oxygen in the three-dimensional network of the biological activity glass are in aqueous medium, ca 2+ Or Na (or) + Is readily water soluble and releases to form a hydrogel layer of hydrous silicic acid, and is therefore referred to as bioactive glass. For decades, a number of studies have demonstrated that bioactive glass has good osteogenic properties, good biocompatibility and self-degrading properties. When the bioactive glass is used as a bone defect repairing material, the bioactive glass can quickly regenerate bone tissues, and the structure and mechanical properties of regenerated bone are well matched with the bone defect part; also, the research shows that the bioactive glass can promote the regeneration of soft tissues such as skin and the like, and has the function of obviously promoting the healing of skin wound surfaces. The biologically active glass was cultured with intestinal epithelial cells by a learner and found that the biologically active glass can promote proliferation of intestinal epithelial cells. However, the dispersibility of the bioactive glass particles in human bodies or organic polymers is poor, and the combination of the bioactive glass and the organic phase is loose, so that the mechanical property and the use function of the composite material are affected. In order to solve the problems, related researches such as CN201210358478.2, CN201611163396.7, CN201811478997.6 and CN201911356221.1 and the like at home and abroad have been reported to modify the surface of bioactive glass by using a silane coupling agent, improve the interfacial compatibility of the bioactive glass and an organic polymer in a chemical bonding mode, improve the bonding capability and dispersibility of the bioactive glass and the organic polymer and enhance the mechanical property of the composite material.
The silane coupling agent is an organosilicon compound having a molecular structure containing a hydrolyzable group and a functional group, and the structure is generally represented by Y n SiX (4-n) Wherein X represents a hydrolyzable group including an alkoxy group, an acyl group, a chlorine atom and the like; the molecular structure of the silane coupling agent is Y which represents a functional group, including alkenyl, epoxy, amino, mercapto, hydroxyl, isocyanate, halogenated alkyl and the like; n is selected from integers from 1 to 3; when the X groups are hydrolyzed, si-X is converted into Si-OH, hydroxyl groups in the Si-OH can be dehydrated and condensed to generate Si-O-Si bonds, and can be combined with Si-OH on the surfaces of glass, silicon dioxide, ceramics and some metal materials or in other molecules to form Si-O-Si bonds, so that functional groups such as alkenyl groups, epoxy groups, amino groups, mercapto groups, hydroxyl groups, isocyanate groups, halogen atoms and the like which can be subjected to chemical reaction can be introduced on the surfaces of the glass, the silicon dioxide, the ceramics or some metal materials. So the silane coupling agent is mainly applied to surface modification of silica materials or ceramics and the like or improves the interface compatibility of composite materials thereof. According to the characteristics of functional groups of the existing silane coupling agent, the surface characteristics of materials to be treated, the modification requirements and the application requirements of some new fields, importance is attached to the re-functionalization of the silane coupling agent. The re-functionalization of the existing silane coupling agent is mainly realized by bonding a structural unit with stronger function through the functional group, so that new functions and applications of materials to be modified are given, for example, CN201010503258.5, CN201610807720.8, CN202010940152.5, CN202110914812.7, CN201610766177.1, CN202010446615.2, CN201910559445.6, CN201811365280.0, CN201310134973.X and the like disclose silane coupling agents carrying quaternary ammonium cations, zwitterions or polyether chains, copolymers containing zwitterionic olefin monomers and olefin silane coupling agents and the like as surface modifying agents of inorganic materials such as glass or silica gel and the like, and positive effects are obtained.
In view of this, in combination with previous research results of the subject groups ZL201910993648.6, ZL2021107850204, ZL201910994314.0, ZL201811189217, CN2023100519084, CN202310116727.5, CN 202310116725.6, etc., the present inventors have made a re-functionalization design of commercially available 3-aminopropyl silane coupling agents, creating a multifunctional silane coupling agent with novel molecular structure. The hydrolyzable group in the molecular structure of the multifunctional silane coupling agent is still a traditional trialkoxy group; the amino group in the 3-aminopropyl silane coupling agent is subjected to almost quantitative aza-Michael addition reaction with diallylamino polyether acrylate, and then is subjected to quaternization reaction with an alkylating agent, propane sultone or gamma-butyrolactone, so that the multifunctional silane coupling agent has more than one quaternary ammonium cation, or sulfobetaine or carboxyl betaine in a molecular structure. Therefore, the multifunctional silane coupling agent is used for surface modification of bioactive glass, so that the enhancement effects of biocompatibility, antibacterial property and hydrophilicity of the surface modified bioactive glass can be obtained; meanwhile, the diallylammonium which is remained on the surface modified bioactive glass has the characteristic of participating in the copolymerization reaction of olefin monomers.
Disclosure of Invention
The invention provides an application of a multifunctional silane coupling agent in the surface modification of bioactive glass, which is characterized by being realized through the following processes: sequentially weighing methanol or ethanol, the multifunctional silane coupling agent and water according to the mass ratio of the multifunctional silane coupling agent to the methanol or ethanol to the water of 2-20:5-50:5-50, preparing a multifunctional silane coupling agent solution at room temperature, stirring, adding bioactive glass, and heating to 50-90 ℃ for reacting for 2-20 hours; and (3) ending the reaction process, cooling the reaction product to room temperature, filtering, washing, sending the filter cake into a vacuum drying oven, and vacuum drying at the temperature of 25-65 ℃ to constant weight to obtain the surface modified bioactive glass.
Wherein the dosage of the multifunctional silane coupling agent is 5-500% of the mass of the bioactive glass particles.
The multifunctional silane coupling agent has a structure shown in a general formula (A), a general formula (A ') or a general formula (A').
Wherein R in formula (A), formula (A' ") or formula (A" ") is selected from C 1 ～C 18 Hydrocarbyl radicals, R 1 Selected from H or methyl, n being selected from natural numbers between 1 and 2000, when Y is selected from C 1 ～C 18 Hydrocarbon radicals or radicalsWhen X is - Selected from Cl - 、Br - 、I - Or p-CH 3 C 6 H 4 SO 3 - When Y is selected from-CH 2 CH 2 CH 2 SO 3 - or-CH 2 CH 2 CH 2 CO 2 - When X is - Any counter anions are not selected; wherein R is 2 Selected from C 1 ～C 18 Hydrocarbyl groups, m is selected from natural numbers between 0 and 2000.
Relevant research results and application experiments have taught us: the structural unit in the multifunctional silane coupling agent can be used for N according to the action and the performance of the functional unit and the actual application requirement + Upper Y, R 1 And R is 2 The purpose optimization selection can be performed. If the hydrophilic function is emphasized, Y of the multifunctional silane coupling agent is preferably CH 3 、R 1 And R is 2 Preferably H or CH 3 N is preferably 1 to 3; if the functions of hydrophilicity, antibiosis and sterilization are emphasized, the Y of the multifunctional silane coupling agent is C 12 H 25 Or C 7 H 8 N is preferably 1 to 3, R 1 And R is 2 Preferably H or CH 3 The method comprises the steps of carrying out a first treatment on the surface of the If the modification such as hydrophilicity, antibiosis, antifouling, biocompatibility and anticoagulation is the main purpose, Y is preferableC 12 H 25 Or C 7 H 8 ，R 2 CH selection 3 N is preferably 8 to 25. In addition, compared with the prior art, one molecule of multifunctional silane coupling agentCan endow the surface of the bioactive glass with a plurality of hydrophilic groups, and is more effective for surface modification of the bioactive glass.
The preparation method of the multifunctional silane coupling agent comprises the steps of dissolving a 3-aminopropyl silane coupling agent in a solvent, controlling the temperature to be 5-35 ℃, and slowly adding diallylamine polyether acrylate by starting stirring under the protection of N2, wherein the dosage of the diallylamine polyether acrylate is 2.0-2.2 times of the molar quantity of the 3-aminopropyl silane coupling agent; after the material addition of the diallylamine polyether acrylate is finished, slowly raising the temperature of a reaction system to 35-90 ℃ for reaction for 2-20 hours, and ending the Michael addition reaction process; maintaining the reaction temperature, adding an alkylating reagent or propane sultone or gamma-butyrolactone into a reaction system, wherein the dosage of the alkylating reagent or propane sultone or gamma-butyrolactone is 1.0-3.5 times of the molar quantity of the 3-aminopropyl silane coupling agent, and after the reaction is continued for 2-20 hours, ending the quaternization reaction process; and then removing part of the solvent by rotary evaporation, cooling the reaction product system to room temperature, separating out a crude product, and purifying the crude product to obtain the multifunctional silane coupling agent with the structure shown in the general formula (A).
Wherein the 3-aminopropyl silane coupling agent has a structure shown in a general formula (B):
wherein R in formula (B) is selected from C 1 ～C 18 A hydrocarbon group.
The solvent refers to one or more than two of methanol, ethanol, propanol, tetrahydrofuran, 1, 4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dimethyl sulfoxide, N-methylpyrrolidone, N-dimethylformamide, N-diethylformamide or hexamethylphosphoramide; the amount of the solvent is 1 to 10 times the mass of the general formula (B).
The diallylamine polyether acrylate has a structure shown in a general formula (C):
wherein R in the formula (C) 1 Selected from H or methyl, and n is selected from natural numbers between 1 and 2000.
The alkylating agent has a structure shown in a general formula (D):
Y-X
general formula (D)
Wherein Y in the formula (D) is selected from C 1 ～C 18 Hydrocarbon radicals or radicalsX is selected from Cl, br, I or p-CH 3 C 6 H 4 SO 3 Wherein m is selected from natural numbers between 0 and 2000, R 2 Selected from C1-C18 hydrocarbyl groups.
The invention provides the beneficial effects of application of a multifunctional silane coupling agent in the surface modification of bioactive glass, which are as follows:
(1) the multifunctional silane coupling agent has the advantages of novel structure, simple preparation method, most of preparation raw materials are commercial products, the product yield in each step of preparation process is high, the purification technology of the multifunctional silane coupling agent is simple and reliable, and the process is simple and easy to implement.
(2) The multifunctional silane coupling agent is easy to dissolve in water and soluble in large amount of methanol or ethanol, and has simple use method and almost no volatile toxic organic matters.
(3) The multifunctional silane coupling agent is used for carrying out surface modification on bioactive glass, and has simple technical process and remarkable modification effect.
Detailed Description
For a further understanding of the present invention, it is to be understood that the present invention is specifically described by way of examples, and is for the purpose of better understanding of the present invention. Therefore, the surface modification of bioactive glass by the multifunctional silane coupling agent is not listed in the examples and should not be construed as limiting the scope of the invention.
Example 1 preparation of surface-modified bioactive glass (A-1)
Step one, preparation of a multifunctional silane coupling agent of the formula (A-1):
78 g (about 0.202 mol) of diallylamino polyether methacrylate of the formula (C-1) is dissolved in 320 g of methanol to be put into a reaction kettle, stirring is started, 22 g (about 0.1 mol) of commercially available KH-550 brand aminosilane coupling agent is slowly added under the protection of N2 at the temperature of 10-15 ℃, after the KH-550 aminosilane coupling agent is completely added, the reaction temperature is raised to 35-45 ℃ for reaction for 12 hours, 44 g (about 0.349 mol) of benzyl chloride is added into the reaction kettle after the reaction temperature is raised to 70-90 ℃ for reaction for 20 hours, part of methanol is removed by rotary evaporation, the temperature of a reaction product system is reduced to room temperature, white solid matters are separated out, and the multifunctional silane coupling agent of the formula (A-1) is prepared by filtering, washing by dehydrated acetone and vacuum drying.
KH-550 is a commodity abbreviation of 3-aminopropyl triethoxysilane, and the yield of intermediate tertiary amine is about 98.3% and the yield of the multifunctional silane coupling agent of formula (A-1) is about 89.7% through sampling, separating and purifying the aza-Michael addition reaction product of the diallylaminopolyether methacrylate of formula (C-1). The IR spectrogram of the multifunctional silane coupling agent also shows strong absorption peaks near 1726nm and 1108 nm; c61.45 (62.00), H8.03 (8.47), N3.01 (3.10) as a result of elemental analysis (theoretical value%) shows a formula C with the design of formula (A-1) 70 H 114 Cl 3 N 3 O 14 Si is identical. The multifunctional silane coupling agent product of the formula (A-1) is subjected to nuclear magnetic resonance and mass spectrometry analysis, and the chemical structure of the product in the preparation process is confirmed to be consistent with the theoretical design.
Step two, preparing surface modified bioactive glass (A-1): 86 g of ethanol, 14 g of a multifunctional silane coupling agent of the formula (A-1) and 100 g of water are weighed, sequentially added into a reaction flask at room temperature, and uniformly stirred to prepare a multifunctional silane coupling agent solution. Then 30 g of calcium phosphorus silicon bioactive glass (purchased from Wohan gram biomedical technology Co., ltd.) with the particle size less than or equal to 10 μm is put into the glass, after ultrasonic treatment for 0.5 hour, the temperature is raised to 70-80 ℃ and stirred for 6 hours, the reaction process is finished, the temperature is reduced and filtered, the filter cake is washed three times by ethanol, and the constant weight is dried in vacuum at the temperature of 50-55 ℃ to prepare 40.8 g of surface modified bioactive glass (A-1).
29.2 g of a blank sample of bioactive glass is prepared by the same method and procedure, and the net weight gain of the surface modified bioactive glass (A-1) can be calculated to be 11.6 g, so that the reaction efficiency of the multifunctional silane coupling agent of the formula (A-1) on the surface of the bioactive glass is estimated to be 91.7%.
In the IR spectrum diagram of the surface modified bioactive glass (A-1) relative to a bioactive glass blank sample, the intermediate strong absorption peaks and the strong absorption peaks are added at 2932nm, 2873nm, 1724nm, 1164nm and the like, and the vibration absorption peaks respectively belong to methyl, methylene, ester carbonyl and C-O-C, so that the surface modified bioactive glass (A-1) has the structural characteristics of carboxylate and ether bond.
Comparative example 1 preparation of surface-modified bioactive glass (A-1')
According to the method and procedure of example 1, 14 g of the aza-Michael addition reaction product of KH-550 aminosilane coupling agent and diallylaminopolyether methacrylate of the formula (C-1) in step one of example 1 was weighed and surface-treated with 30 g of calcium phosphorus silicon based bioactive glass frit having a particle size of 10 μm or less, manufactured by WU Han Ke Mike biomedical technology Co., ltd, to obtain 40.4 g of surface-modified bioactive glass (A-1').
By calculating a net gain of 11.2 grams for the surface modified bioactive glass (A-1') relative to the bioactive glass blank, the efficiency of the reaction of the aza-Michael addition product on the bioactive glass surface was 90.3%. Analytical characterization of the surface-modified bioactive glass (A-1 ') using an analytical instrument demonstrated that the surface-modified bioactive glass (A-1') has structural units of carboxylate and ether linkages.
Example 2 preparation of surface-modified bioactive glass (A-2)
According to the procedure of step one of example 1, the diallylaminopolyether methacrylate of the formula (C-1) is converted into 2- (N, N-diene) methacrylatePropylamino) ethyl ester and benzyl chloride are changed into omega-methoxy polyethylene glycol-400 p-toluenesulfonate to prepare the multifunctional silane coupling agent of formula (A-2) with the yield of 91.4%. IR spectrum of multifunctional silane coupling agent of formula (A-2), 1 Results of H-NMR, mass spectrometry and elemental analysis (theoretical value%): C53.09 (55.50), H7.93 (8.80), N1.64 (1.72), indicate the formula C with formula (A-2) 114 H 213 N 3 O 44 S 2 Si is basically consistent, thereby judging that the chemical structure of the multifunctional silane coupling agent product of the formula (A-2) is consistent with the theoretical design.
The procedure of the second step of example 1 was followed, using a multifunctional silane coupling agent of the formula (A-2) for surface modification treatment of calcium-phosphorus-silicon-based bioactive glass powder having a particle diameter of 10 μm or less, which was produced by Wohan Kemi biomedical technology Co., ltd, to obtain a surface-modified bioactive glass (A-2). By using IR spectrum analysis means, it was confirmed that the surface-modified bioactive glass (A-2) had structural characteristics of carboxylate and ether bond.
Example 3 preparation of surface-modified bioactive glass (A-3)
According to the method and the operation steps of the embodiment 1, the calcium phosphorus silicon bioactive glass powder with the particle diameter less than or equal to 10 mu m produced by the Wuhan Ke Mike biomedical technology Co., ltd in the second embodiment 1 is changed into SiO produced by Hebei excellent solid biotechnology Co., ltd 2 Content of 45%, caO 2 Content of 24.5%, na 2 O content 24.5%, P 2 O 5 The bioactive glass with the content of 6.0 percent is named as euonyolin, and the particle size is less than or equal to 45 mu m powder, so as to prepare the surface modified bioactive glass (A-3). And adopting an infrared spectrum analysis means to judge that the surface modified bioactive glass (A-3) has the structural characteristics of carboxylate and ether bond.
Comparative example 2 preparation of surface-modified bioactive glass (A-3')
According to the procedure of step two of example 1, KH-550 aminosilane coupling agent and formula (II) of step one of example 1 were taken(C-1) Aza-Michael addition reaction product of diallylaminopolyether methacrylate to SiO from Hebei's Excellent Biotechnology Co., ltd 2 Content of 45%, caO 2 Content of 24.5%, na 2 O content 24.5%, P 2 O 5 The bioactive glass with the content of 6.0 percent is subjected to surface modification treatment to prepare the surface modified bioactive glass (A-3').
Example 4 preparation of surface-modified bioactive glass (A-4)
According to the method and the operation procedure of example 1, KH-550 amino silane coupling agent in the first step was changed to KH-540 amino silane coupling agent, diallylaminopolyether methacrylate of the formula (C-1) was changed to 2- (N, N-diallylamino) ethyl methacrylate, and benzyl chloride was changed to bromododecane, to prepare a multifunctional silane coupling agent of the formula (A-4) in 73.3% yield. IR spectrum of multifunctional silane coupling agent of formula (A-4), 1 Results of H-NMR, mass spectrometry and elemental analysis (theoretical value%): C53.18 (55.69), H9.38 (10.00), br17.61 (19.50), indicate the design formula C with formula (A-4) 57 H 122 Br 3 N 3 O 7 Si is substantially identical, thereby confirming that the chemical structure of formula (A-4) is identical to the theoretical design.
According to the method and the operation steps of the embodiment 1, the calcium phosphorus silicon bioactive glass powder with the particle size less than or equal to 10 mu m produced by the Wuhank biomedical technology Co., ltd in the second step is changed into nano bioactive glass (the nano bioactive glass is self-made according to the ZL02110586.3 published technology). And (3) carrying out surface modification treatment on the nano bioactive glass by using a multifunctional silane coupling agent shown in the formula (A-4) to obtain the surface modified nano bioactive glass (A-4). The infrared spectrum analysis means is adopted to prove that the surface modified nanometer bioactive glass (A-4) has the structural characteristics of carboxylate and ether bond.
Example 5 characteristics of bioactive glass before and after surface modification in examples 1 to 4
1.5 g of the surface-modified bioactive glass in examples 1 to 4 was taken and pressed by a pressing machine, and the contact angle of pure water of each pressed sheet was measured under static conditions by a contact angle meter, and the results are shown in Table 1.
Table 1 results of measuring water contact angle of each bioactive glass in examples 1 to 4
Examples 1 2 3 4 Comparative example 1 Comparative example 2 Blank space
Water contact angle (°) 0 0 0 0 23.4 25.2 10.7
The results in Table 1 prove that the hydrophilicity of the bioactive glass is obviously improved after the bioactive glass is subjected to surface treatment by the multifunctional silane coupling agent; the silane coupling agent of organic amine is used for modifying bioactive glass, and the hydrophilicity of the bioactive glass is reduced.

Claims (7)

1. The application of the multifunctional silane coupling agent in the surface modification of the bioactive glass is characterized by comprising the following steps: sequentially weighing methanol or ethanol, the multifunctional silane coupling agent and water according to the mass ratio of the multifunctional silane coupling agent to the methanol or ethanol to the water of 2-20:5-50:5-50, preparing the multifunctional silane coupling agent solution at room temperature, stirring, adding bioactive glass, heating to 50-90 ℃ and reacting for 2-20 hours; ending the reaction process, cooling the reaction system to room temperature, filtering, washing a filter cake by using methanol or ethanol, then sending the filter cake into a vacuum drying oven, and vacuum drying to constant weight at the temperature of 25-65 ℃ to obtain the surface modified bioactive glass;
wherein the dosage of the multifunctional silane coupling agent is 5-500% of the mass of the bioactive glass particles.
2. The use of a multifunctional silane coupling agent according to claim 1 for modifying the surface of bioactive glass, wherein the multifunctional silane coupling agent has a structure represented by one of the general formula (a), the general formula (a' ") or the general formula (a" "):
wherein R in formula (A), formula (A' ") or formula (A" ") is C 1 ～C 18 Hydrocarbyl radicals, R 1 Selecting H or methyl, n is selected from natural numbers between 1 and 2000, when Y is C 1 ～C 18 Hydrocarbon radicals or radicalsWhen X is - Selecting Cl - 、Br - 、I - Or p-CH 3 C 6 H 4 SO 3 - When Y is selected from-CH 2 CH 2 CH 2 SO 3 - or-CH 2 CH 2 CH 2 CO 2 - When X is - Any counter anions are not selected;
wherein R is 2 Selecting C 1 ～C 18 Hydrocarbyl groups, m is selected from natural numbers between 0 and 2000.
3. The application of the multifunctional silane coupling agent in the surface modification of bioactive glass according to claim 1, which is characterized in that the preparation method of the multifunctional silane coupling agent is that the 3-aminopropyl silane coupling agent is dissolved in a solvent, the temperature is controlled to be 5-35 ℃, under the protection of N2, the stirring is started, the diallylamine polyether acrylate is slowly added, and the dosage of the diallylamine polyether acrylate is 2.0-2.2 times of the molar quantity of the 3-aminopropyl silane coupling agent; after the material addition of the diallylamine polyether acrylate is finished, slowly raising the temperature of a reaction system to 35-90 ℃ for reaction for 2-20 hours, and ending the Michael addition reaction process; maintaining the reaction temperature, adding an alkylating reagent or propane sultone or gamma-butyrolactone into a reaction system, wherein the dosage of the alkylating reagent or propane sultone or gamma-butyrolactone is 1.0-3.5 times of the molar quantity of the 3-aminopropyl silane coupling agent, and after the reaction is continued for 2-20 hours, ending the quaternization reaction process; then removing part of solvent by rotary evaporation, cooling to room temperature, separating out a crude product, and purifying the crude product to obtain the multifunctional silane coupling agent with the structure shown in the general formula (A);
wherein the dosage of the solvent is 1 to 10 times of the mass of the 3-aminopropyl silane coupling agent.
4. The use of a multifunctional silane coupling agent according to claim 3 for modifying the surface of bioactive glass, wherein said 3-aminopropyl silane coupling agent has the structure of formula (B):
wherein R in the general formula (B) is C 1 ～C 18 A hydrocarbon group.
5. The method for modifying the surface of bioactive glass using a multifunctional silane coupling agent as claimed in claim 3, wherein said solvent is one or more of methanol, ethanol, propanol, tetrahydrofuran, 1, 4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dimethyl sulfoxide, N-methylpyrrolidone, N-dimethylformamide, N-diethylformamide, and hexamethylphosphoramide.
6. The use of a multifunctional silane coupling agent according to claim 3 for modifying the surface of bioactive glass, wherein said diallylamine polyether acrylate has the structure of formula (C):
wherein R in the formula (C) 1 H or methyl is selected, and n is selected from natural numbers between 1 and 2000.
7. The use of a multifunctional silane coupling agent according to claim 3 for modifying the surface of bioactive glass, wherein said alkylating agent has the structure of formula (D):
Y-X
general formula (D)
Wherein Y in the general formula (D) is C 1 ～C 18 Hydrocarbon radicals or radicalsWhen X is Cl, br, I or p-CH 3 C 6 H 4 SO 3 One of the following;
wherein m is selected from natural numbers between 0 and 2000, R 2 Selecting C 1 ～C 18 A hydrocarbon group.
CN202311027220.9A 2023-08-16 2023-08-16 Application of multifunctional silane coupling agent in surface modification of bioactive glass Pending CN117069389A (en)

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