CN111588907A - Preparation method of multifunctional heterostructure microfiber - Google Patents

Preparation method of multifunctional heterostructure microfiber Download PDF

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CN111588907A
CN111588907A CN202010505504.4A CN202010505504A CN111588907A CN 111588907 A CN111588907 A CN 111588907A CN 202010505504 A CN202010505504 A CN 202010505504A CN 111588907 A CN111588907 A CN 111588907A
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microfiber
heterostructure
phase
preparation
fluid
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陈苏
黄秋
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Nanjing Tech University
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Nanjing Tech University
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    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
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    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/20—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/60—Materials for use in artificial skin
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/06—Wet spinning methods
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/28—Formation of filaments, threads, or the like while mixing different spinning solutions or melts during the spinning operation; Spinnerette packs therefor
    • D01D5/30—Conjugate filaments; Spinnerette packs therefor
    • D01D5/34—Core-skin structure; Spinnerette packs therefor
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/10—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one other macromolecular compound obtained by reactions only involving carbon-to-carbon unsaturated bonds as constituent
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/14—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyester as constituent
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/18—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from other substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104—Silver, e.g. silver sulfadiazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
    • A—HUMAN NECESSITIES
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    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/30—Compounds of undetermined constitution extracted from natural sources, e.g. Aloe Vera
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/412—Tissue-regenerating or healing or proliferative agents
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    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/418—Agents promoting blood coagulation, blood-clotting agents, embolising agents
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    • A61L2400/00—Materials characterised by their function or physical properties
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Abstract

The invention relates to a preparation method of multifunctional heterostructure microfiber; the hydrophobic polymer solution dissolved by an organic solvent and the hydrophilic polymer solution dissolved by water are respectively used as an internal phase fluid and an external phase fluid, and the rapid continuous preparation of the multifunctional heterostructure microfiber can be realized by a simple microfluid device by utilizing the principle that the hydrophilic polymer and calcium ions generate ionic crosslinking effect and the hydrophilic polymer wraps the hydrophobic fluid in the spinning process. The heterostructure microfiber prepared by the invention has a double drug loading function, researches show that the double drug loading microfiber has good hemostatic and blood coagulation performance, and the artificial skin scaffold woven by the double drug loading microfiber has a good promotion effect on wound healing, so that the heterostructure microfiber is expected to provide an important technical support for the development of the fields of novel wound dressings, artificial skin and the like.

Description

Preparation method of multifunctional heterostructure microfiber
Technical Field
The invention relates to a preparation method of multifunctional heterostructure microfiber, in particular to a rapid continuous preparation method of multifunctional microfiber by adopting a microfluid wet spinning technology.
Background
The heterostructure microfiber is widely concerned due to the advantages of the structure and the performance, the functional heterostructure microfiber can be constructed by means of electrostatic spinning, microfluidic wet spinning and the like, and the prepared heterostructure microfiber has a plurality of applications in the fields of sensing technology, photoelectric device, photocatalysis, biotechnology and the like. At present, how to apply the heterostructure microfiber to the biomedical field becomes a hot research focus of the heterostructure microfiber. The microfluid wet spinning technology is an ideal reactor platform for producing the microfibers with the multilevel structure, and the morphology, the size and the composition of the microfibers can be accurately regulated and controlled by the microfluid wet spinning technology. Therefore, ordered heterostructure microfibers with stable structures can be constructed by microfluidic wet spinning techniques. The invention combines the ionic crosslinking principle to realize the rapid solidification of the external phase polymer fluid, and continuously prepares the functional microfiber with the heterostructure through the wrapping effect of the external phase polymer fluid on the internal phase polymer fluid.
Disclosure of Invention
The invention aims to solve the technical problems that the research of the heterostructure fiber material in the biomedical field is not deep enough, the multifunctional heterostructure microfiber is rapidly and continuously prepared by a simple microfluid wet spinning technology and is successfully applied to the biomedical field. The functional material has simple preparation method and low cost, and can be successfully applied to the fields of blood coagulation and hemostasis and wound healing promotion. In order to achieve the above purpose, a method for preparing multifunctional heterostructure microfiber is provided, a simple microfluidic device is designed, and functional heterostructure microfiber is obtained by continuously adjusting spinning process parameters.
The technical scheme of the invention is as follows: a preparation method of multifunctional heterostructure microfiber comprises the following specific steps:
A. uniformly dissolving a hydrophobic polymer in an organic solvent and doping an oil-soluble drug to obtain an internal phase spinning solution;
uniformly dissolving a hydrophilic polymer in water and adding a water-soluble drug to obtain an external phase spinning solution;
B. injecting the two prepared spinning solutions into a microfluid device as an internal phase fluid and an external phase fluid respectively, and finally introducing the two prepared spinning solutions into a receiving device filled with a curing agent for curing and forming; by continuously adjusting the parameters of the spinning process, such as:
the diameters of the outlets of the inner phase and the outer phase of the microchip and the flow rates of the fluid of the inner phase and the outer phase are used for obtaining the functional heterostructure microfiber.
Preferably, the hydrophobic polymer in the step A is polylactic acid or polylactic acid-glycolic acid copolymer; the hydrophilic polymer is sodium alginate or sodium polyacrylate; the organic solvent is dichloromethane; the oil-soluble medicine is emu oil or tetrahydrocurcumin; the water-soluble medicine is nano silver or fibrinogen.
Preferably, the mass fraction of the hydrophobic polymer in the internal phase spinning solution is 2-5%, and the mass fraction of the oil-soluble drug is 0.03-0.05%; the mass fraction of the hydrophilic polymer in the external phase spinning solution is 1-2.5%, and the mass fraction of the water-soluble drug is 0.02-0.03%.
Preferably, the curing agent in the step B is CaCl2The mass concentration of the solution is 5-10%.
Preferably, the spinning process parameters in the step B are as follows: the inner phase outlet diameter of the microchip in the microfluidic device is 140-; the flow rate of the fluid of the inner phase is 3-7mL/h, and the flow rate of the fluid of the outer phase is 5-15 mL/h.
Has the advantages that:
1. the heterostructure microfiber prepared by the invention has the double-medicine double-speed release function and has the effects of quickly stopping bleeding and promoting wound healing.
2. The preparation method is simple in preparation process and low in production cost, and can realize rapid macro preparation of the multifunctional heterostructure microfiber.
3. The heterostructure dual-drug loaded microfiber prepared by the method lays a foundation for researches on artificial skin, novel medical materials and the like.
Drawings
FIG. 1 is a schematic representation of the preparation of a multifunctional heterostructure microfiber according to the present invention; in the figure, 1-a two-channel microflow pump, 2-a first injection pump, 3-a second injection pump, 4-a 1 capillary, 5-a 2 capillary, 6-a core-shell microchip, 7-a 3 capillary and 8-a receiving device are arranged.
Detailed Description
The present invention is further illustrated by the following specific examples, but the present invention is not limited to only the following examples. A schematic of the preparation of a multifunctional heterostructure microfiber is shown in figure 1.
Example 1
Adding 2.0g of polylactic acid particles and 30mg of oil-soluble drug emu oil into an organic solvent dichloromethane, and uniformly mixing to obtain 100g of internal phase spinning solution; adding 2.0g of sodium alginate powder and 20mg of water-soluble drug nano-silver into water, and uniformly mixing to obtain 100g of external phase spinning solution. As shown in figure 1, two solutions are respectively added into a second injection pump 3 and a first injection pump 2 as internal and external phase fluids, then the flow rate of the two-phase fluid is controlled by a double-channel microflow pump, the two-phase solution is respectively guided into a microflow control chip 6 through a No. 2 capillary 5 and a No. 1 capillary 4, unformed heterostructure fibers are guided into a receiving device 8 through a No. 3 capillary 7 to be solidified and formed, the flow rate of the external phase is 5mL/h, the flow rate of the internal phase is 3mL/h, and the generated unformed heterostructure microfibers are introduced into 5 wt% of CaCl2And (4) carrying out solidification forming in a solidification bath.
And (3) spinning by using a micro-fluid device of a chip with the microchip inner phase outlet diameter of 140 microns and the microchip outer phase outlet diameter of 400 microns, further freeze-drying the obtained double-drug-loaded hybrid microfiber, and then performing test research on in-vitro hemostasis and wound healing.
Example 2
Adding 5.0g of polylactic acid particles and 50mg of oil-soluble drug emu oil into an organic solvent dichloromethane, and uniformly mixing to obtain 100g of internal phase spinning solution; adding 2.5g of sodium alginate powder and 30mg of water-soluble drug nano-silver into water, and uniformly mixing to obtain 100g of external phase spinning solution. As shown in figure 1, two solutions are respectively added into a second injection pump 3 and a first injection pump 2 as internal and external phase fluids, then the flow rate of the two-phase fluid is controlled by a double-channel microflow pump, the two-phase solution is respectively guided into a microflow control chip 6 through a No. 2 capillary 5 and a No. 1 capillary 4, unformed heterostructure fibers are guided into a receiving device 8 through a No. 3 capillary 7 to be solidified and formed, the flow rate of the external phase is 15mL/h, the flow rate of the internal phase is 7mL/h, and the generated unsolidified heterostructure microfibers are introduced into 10 wt% of CaCl2And (4) carrying out solidification forming in a solidification bath.
The micro-fluid device with a microchip inner phase outlet diameter of 160 μm and an outer phase outlet diameter of 460 μm is selected for spinning, the obtained double-drug-loaded hybrid microfiber is further freeze-dried, and then test studies on in-vitro hemostasis and wound healing are carried out.
Example 3
Adding 3.0g of polylactic acid-glycolic acid copolymer particles and 40mg of oil-soluble medicine tetrahydrocurcumin into an organic solvent dichloromethane, and uniformly mixing to obtain 100g of internal phase spinning solution; 2.2g of sodium alginate powder and 25mg of water-soluble drug fibrinogen are added into water and are uniformly mixed to obtain 100g of external phase spinning solution. As shown in figure 1, two solutions are respectively added into a second injection pump 3 and a first injection pump 2 as internal and external phase fluids, then the flow rate of the two-phase fluid is controlled by a double-channel microflow pump, the two-phase solution is respectively guided into a microflow control chip 6 through a No. 2 capillary 5 and a No. 1 capillary 4, unformed heterostructure fibers are guided into a receiving device 8 through a No. 3 capillary 7 to be solidified and formed, the flow rate of the external phase is 10mL/h, the flow rate of the internal phase is 5mL/h, and the generated unformed heterostructure microfibers are introduced into 7 wt% of CaCl2And (4) carrying out solidification forming in a solidification bath.
And (3) spinning by using a micro-fluid device of a chip with the microchip inner phase outlet diameter of 150 microns and the microchip outer phase outlet diameter of 430 microns, further freeze-drying the obtained double-drug-loaded hybrid microfiber, and then performing test research on in-vitro hemostasis and wound healing.
Example 4
Adding 4.0g of polylactic acid-glycolic acid copolymer particles and 50mg of oil-soluble medicine tetrahydrocurcumin into an organic solvent dichloromethane, and uniformly mixing to obtain 100g of internal phase spinning solution; 1.0g of sodium polyacrylate powder and 25mg of water-soluble drug fibrinogen are added into water and uniformly mixed to obtain 100g of external phase spinning solution. As shown in figure 1, two solutions are respectively added into a second injection pump 3 and a first injection pump 2 as internal and external phase fluids, then the flow rate of the two-phase fluid is controlled by a double-channel microflow pump, the two-phase solution is respectively guided into a microflow control chip 6 through a No. 2 capillary 5 and a No. 1 capillary 4, unformed heterostructure fibers are guided into a receiving device 8 through a No. 3 capillary 7 to be solidified and formed, the flow rate of the external phase is 10mL/h, the flow rate of the internal phase is 5mL/h, and the generated unformed heterostructure microfibers are introduced into 8 wt% of CaCl2And (4) carrying out solidification forming in a solidification bath.
The micro-fluid device with a microchip having an inner phase outlet diameter of 150 μm and an outer phase outlet diameter of 460 μm was selected for spinning, the obtained dual drug-loaded hybrid microfibers were further freeze-dried, and then tested for hemostasis and wound healing in vitro.
The results of the above experimental tests are shown in the following table.
Table 1 shows the cell activity, blood coagulation rate and wound healing time of different materials
Experimental Material Cell Activity/% Blood coagulation rate/sec Healing time/day
Example 1 93 7 8
Example 2 95 6 6
Example 3 96 5 7
Example 4 92 4 7
Blank control 97 Non-blood coagulation 15
From the test results, the prepared heterostructure microfiber has good biocompatibility, and the cell activity is over 90% after 24h of culture. The dried double-drug loaded microfiber has the function of double-drug double-speed release. Therefore, the dried double-drug-loaded microfiber has a rapid blood coagulation and hemostasis effect. The prepared microfibers are woven into an artificial skin stent for carrying out wound healing experiments, and based on the performance of dual-drug dual-speed release and good biocompatibility, the fibers can effectively promote the healing of wounds.

Claims (5)

1. A preparation method of multifunctional heterostructure microfiber comprises the following specific steps:
A. uniformly dissolving a hydrophobic polymer in an organic solvent and doping an oil-soluble drug to obtain an internal phase spinning solution; uniformly dissolving a hydrophilic polymer in water and adding a water-soluble drug to obtain an external phase spinning solution;
B. injecting the two prepared spinning solutions into a microfluid device as an internal phase fluid and an external phase fluid respectively, and finally introducing the two prepared spinning solutions into a receiving device filled with a curing agent for curing and forming; the multifunctional heterostructure microfiber is obtained by continuously adjusting spinning process parameters.
2. The method according to claim 1, wherein the hydrophobic polymer in step a is polylactic acid or a polylactic acid-glycolic acid copolymer; the hydrophilic polymer is sodium alginate or sodium polyacrylate; the organic solvent is dichloromethane; the oil-soluble medicine is emu oil or tetrahydrocurcumin; the water-soluble medicine is nano silver or fibrinogen.
3. The preparation method according to claim 1, wherein the mass fraction of the hydrophobic polymer in the internal phase spinning solution is 2-5%, and the mass fraction of the oil-soluble drug is 0.03-0.05%; the mass fraction of the hydrophilic polymer in the external phase spinning solution is 1-2.5%, and the mass fraction of the water-soluble drug is 0.02-0.03%.
4. The method according to claim 1, wherein the curing agent in step B is CaCl2The mass concentration of the solution is 5-10%.
5. The preparation method according to claim 1, wherein the spinning process parameters in step B are: the inner phase outlet diameter of the microchip in the microfluidic device is 140-; the flow rate of the fluid of the inner phase is 3-7mL/h, and the flow rate of the fluid of the outer phase is 5-15 mL/h.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112709002A (en) * 2020-12-04 2021-04-27 广州贝奥吉因生物科技股份有限公司 Alginate antibacterial composite membrane and preparation method thereof
CN113186609A (en) * 2021-04-23 2021-07-30 上海大学 Three-dimensional biological printing method and system based on microfluid spinning

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