CN114533938A - Liquid embolic agent and application thereof in preparation of embolic agent - Google Patents
Liquid embolic agent and application thereof in preparation of embolic agent Download PDFInfo
- Publication number
- CN114533938A CN114533938A CN202210179338.2A CN202210179338A CN114533938A CN 114533938 A CN114533938 A CN 114533938A CN 202210179338 A CN202210179338 A CN 202210179338A CN 114533938 A CN114533938 A CN 114533938A
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- liquid
- polyethylene glycol
- embolic agent
- arm polyethylene
- glycol dipropyl
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- 239000007788 liquid Substances 0.000 title claims abstract description 72
- 230000003073 embolic effect Effects 0.000 title claims abstract description 27
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 49
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 49
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- GQZXRLWUYONVCP-UHFFFAOYSA-N 3-[1-(dimethylamino)ethyl]phenol Chemical compound CN(C)C(C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-UHFFFAOYSA-N 0.000 claims abstract description 11
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007800 oxidant agent Substances 0.000 claims abstract description 7
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000004386 diacrylate group Chemical group 0.000 claims description 13
- 230000010102 embolization Effects 0.000 claims description 13
- 239000000017 hydrogel Substances 0.000 claims description 9
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 abstract description 8
- 230000036770 blood supply Effects 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 210000004088 microvessel Anatomy 0.000 abstract description 4
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 210000004204 blood vessel Anatomy 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 7
- 208000005189 Embolism Diseases 0.000 description 6
- 210000002767 hepatic artery Anatomy 0.000 description 6
- 239000004005 microsphere Substances 0.000 description 4
- RKSYJNCKPUDQET-UHFFFAOYSA-N n,n-dipropylprop-2-enamide Chemical compound CCCN(CCC)C(=O)C=C RKSYJNCKPUDQET-UHFFFAOYSA-N 0.000 description 4
- 239000011859 microparticle Substances 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 238000002583 angiography Methods 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000005443 Circulating Neoplastic Cells Diseases 0.000 description 1
- 108010064719 Oxyhemoglobins Proteins 0.000 description 1
- 206010045168 Tumour embolism Diseases 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000002592 echocardiography Methods 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 206010055031 vascular neoplasm Diseases 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
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Classifications
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- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0031—Hydrogels or hydrocolloids
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/02—Surgical adhesives or cements; Adhesives for colostomy devices containing inorganic materials
-
- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/06—Flowable or injectable implant compositions
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention relates to a liquid embolic agent, which comprises liquid A and liquid B which are independent, wherein the liquid A is a water solution of a polyethylene glycol compound and a persulfuric acid oxidant, the liquid B is a water solution of N, N, N, N-tetramethyl ethylenediamine, the polyethylene glycol compound is straight-chain or polyethylene glycol dipropyl amide, 3-arm polyethylene glycol dipropyl maleate, 3-arm polyethylene glycol dipropyl amide, 4-arm polyethylene glycol dipropyl maleate, 4-arm polyethylene glycol dipropyl amide, 8-arm polyethylene glycol dipropyl maleate or 8-arm polyethylene glycol dipropyl amide, and the mass ratio of the polyethylene glycol compound to the N, N, N, N-tetramethyl ethylenediamine is (5-100) to 1. Use of a liquid embolic agent according to the present invention for the preparation of an embolic agent. The liquid embolic agent can completely embolize blood supply vessels of tumors to achieve better treatment effect because the liquid can flow to the tips of micro vessels and the branch ends of the micro vessels due to the liquidity of the liquid.
Description
Technical Field
The invention relates to the field of interventional embolization, in particular to a liquid embolization agent and application thereof in preparation of embolization agents.
Background
The embolism agent is a common product used for tumor embolism or rich vascular tumor intervention, can cause the tumor tissue to lack nutrition necessary for growth and be hungry due to insufficient blood supply of the tumor by embolizing blood supply vessels of the tumor, but the existing embolism agents are both microparticle embolization or microsphere embolization agents, and although the two embolization agents can play a role in embolization, the embolization agents are microparticles or microspheres, have larger volume and the minimum diameter of about 100um, but can not achieve complete embolization for the blood vessel end with the diameter of less than 100um at the end of the blood supply vessel end of the tumor tissue, so that embolization to the end of the blood supply capillary of the tumor is difficult. Furthermore, early embolic materials were in a solid or semi-solid state and were in the form of microparticles or microspheres for better delivery. A certain gap exists between the microspheres, so that the blood vessel cannot be completely embolized, and the blood vessel is easy to recover due to the fluidity of blood.
Disclosure of Invention
In order to solve the problems that the embolism to the tail end of a blood supply micro-vessel of a tumor is difficult and the like in the prior art, the invention provides a liquid embolic agent and application thereof in preparing the embolic agent.
The liquid embolic agent comprises liquid A and liquid B which are independent, wherein the liquid A is an aqueous solution of a polyethylene glycol compound and a persulfuric acid oxidizing agent, the liquid B is an aqueous solution of N, N, N, N-tetramethyl ethylenediamine, and the polyethylene glycol compound is linear polyethylene glycol dipropyl maleate, linear polyethylene glycol dipropyl acrylamide, 3-arm polyethylene glycol dipropyl maleate, 3-arm polyethylene glycol dipropyl acrylamide, 4-arm polyethylene glycol dipropyl maleate, 4-arm polyethylene glycol dipropyl acrylamide, 8-arm polyethylene glycol dipropyl maleate or 8-arm polyethylene glycol dipropyl acrylamide, wherein the mass ratio of the polyethylene glycol compound to the N, N, N, N-tetramethyl ethylenediamine is (5-100) to 1.
Preferably, the polyethylene glycol compound is polyethylene glycol diacrylate, 4-arm polyethylene glycol diacrylate, 8-arm polyethylene glycol diacrylate, 4-arm polyethylene glycol diacrylate or 8-arm polyethylene glycol diacrylate.
Preferably, the mass concentration of the polyethylene glycol compound in the liquid A is 2-40%.
Preferably, the persulfate oxidizer is ammonium persulfate or sodium persulfate.
Preferably, the mass concentration of the persulfuric acid oxidizing agent in the A liquid is 0.1-0.3%.
Preferably, the mass concentration of the N, N, N, N-tetramethylethylenediamine in the liquid B is 0.5-1.5%.
According to the application of the liquid embolic agent in the preparation of the embolic agent, the liquid A and the liquid B are respectively extracted into the syringes, the syringe A is respectively connected with the cavity A by using the double-cavity microcatheter, the syringe B is connected with the cavity B, and the liquid A and the liquid B are solidified into hydrogel after contacting so as to realize embolization.
Preferably, the syringe is pushed at the same speed.
Preferably, the liquid A and the liquid B are contacted and then cured into hydrogel within 2-200 s.
The liquid embolic agent according to the present invention is liquid before delivery and cures into a hydrogel within 2-200s after being pushed into the microvessels. Because the liquid can flow to the end of the micro blood vessel and the branch end, the liquid embolic agent can completely embolize blood supply vessels of tumors, thereby achieving better treatment effect.
Drawings
FIG. 1 is a pre-embolization hepatic artery angiogram according to an application example of the present invention;
fig. 2 is a post-embolization hepatic artery angiogram according to an application example of the present invention.
Detailed Description
The preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings.
Experimental equipment: double-lumen microcatheter (1.9F/87cm), 3.0ml syringe, vascular model.
Example 1
Liquid A: 0.5g of polyethylene glycol diacrylate and 0.05g of ammonium persulfate were dissolved in 25ml of an aqueous solution having a pH of 7.5, and 3ml of the solution was taken out into syringe A using a 3ml syringe.
B, liquid: 0.1g of N, N, N, N-tetramethylethylenediamine was dissolved in 10ml of purified water, and 3ml of the solution was taken out into the syringe B using a 3ml syringe.
The syringe A is connected with the cavity A of the double-cavity micro catheter through a luer base, the syringe B is connected with the cavity B of the double-cavity micro catheter through the luer base, and the far end of the double-cavity micro catheter is placed in a blood vessel model. Meanwhile, the A/B injector push rod is pushed, A, B liquid flows into the blood vessel model through the cavity channel of each A/B injector push rod, and the liquid is polymerized into hydrogel after 180 seconds, so that the blood vessel embolism is complete.
Example 2
Liquid A: 0.5g of 8-arm polyethylene glycol diacrylate and 0.05g of ammonium persulfate were dissolved in 25ml of an aqueous solution having a pH of 7.5, and 3ml of the solution was taken out into syringe A using a 3ml syringe.
B, liquid: 0.1g of N, N, N, N-tetramethylethylenediamine was dissolved in 10ml of purified water, and 3ml of the solution was taken out into the syringe B using a 3ml syringe.
The syringe A is connected with the cavity A of the double-cavity micro catheter through a luer base, the syringe B is connected with the cavity B of the double-cavity micro catheter through the luer base, and the far end of the double-cavity micro catheter is placed in a blood vessel model. Meanwhile, the A/B injector push rod is pushed, A, B liquid flows into the blood vessel model through the cavity channel of each A/B injector push rod, and the liquid is polymerized into hydrogel after 180 seconds, so that the blood vessel embolism is complete.
Example 3
Liquid A: 0.5g of 8-arm polyethylene glycol diacrylate and 0.04g of sodium persulfate were dissolved in 25ml of an aqueous solution having a pH of 7.5, and 3ml of the solution was taken out into syringe A using a 3ml syringe.
B, liquid: 0.08g of N, N, N, N-tetramethylethylenediamine was dissolved in 10ml of purified water, and 3ml of the solution was taken up in syringe B using a 3ml syringe.
The syringe A is connected with the cavity A of the double-cavity micro catheter through a luer base, the syringe B is connected with the cavity B of the double-cavity micro catheter through the luer base, and the far end of the double-cavity micro catheter is placed in a blood vessel model. Simultaneously pushing the push rod of the A/B syringe, A, B allowing the liquid to flow into the blood vessel model via the respective channels, polymerizing into hydrogel after 168s, and completing the embolism of the blood vessel
Example 4
Liquid B was prepared in the same manner as in example 1, with only the composition of liquid a being changed, and the time for polymerization into a hydrogel was observed.
TABLE 1 polymerization time of solutions of different concentrations
Application example
Liquid embolic agent animal experiment, selecting the animal as pig.
1) The experimental animals arrived 7 days before the operation so as to adapt to the constant temperature and humidity environment in the animal room. Lighting is carried out alternately for 12h/12h every day; respectively feeding a proper amount of animal feed once every day in the morning, afternoon and afternoon; the water is freely drunk.
2) Each animal was fasted for 12 hours before surgery, but had free access to water.
3) The surgical implant is not watered in the morning.
4) General anesthesia is performed through oral photopic tracheal intubation, and the anesthesia machine assists in ventilation.
5) Preoperative echocardiography.
6) After the animal is transferred into an operating room, the animal is transported to the right side of the operating room and is positioned on an operating table; continuously monitoring the heart rate, pulse and oxygenation function of an oxyhemoglobin saturation instrument of the animal by using a body surface electrode; placing a body temperature monitoring probe to monitor the body temperature of the animal; the surgical field is disinfected by iodophor skin and laid with sterile towel.
7) Establishment of arteriovenous access
8) Preoperative hepatic artery angiography (as shown in figure 1)
9) Injection of liquid embolic agents
10) Postoperative instant hepatic artery angiography (as shown in figure 2)
Animal experiments carried out by using a pig hepatic artery model show that the liquid embolic agent can completely embolize the tail end of a hepatic artery.
The above embodiments are merely preferred embodiments of the present invention, which are not intended to limit the scope of the present invention, and various changes may be made in the above embodiments of the present invention. All simple and equivalent changes and modifications made according to the claims and the content of the specification of the present application fall within the scope of the claims of the present patent application. The invention has not been described in detail in order to avoid obscuring the invention.
Claims (9)
1. The liquid embolic agent is characterized by comprising liquid A and liquid B which are independent, wherein the liquid A is an aqueous solution of a polyethylene glycol compound and a persulfuric acid oxidizing agent, the liquid B is an aqueous solution of N, N, N, N-tetramethyl ethylenediamine, and the polyethylene glycol compound is straight-chain polyethylene glycol dipropyl maleate, straight-chain polyethylene glycol dipropyl amide, 3-arm polyethylene glycol dipropyl maleate, 3-arm polyethylene glycol dipropyl amide, 4-arm polyethylene glycol dipropyl maleate, 4-arm polyethylene glycol dipropyl amide, 8-arm polyethylene glycol dipropyl maleate or 8-arm polyethylene glycol dipropyl amide, wherein the mass ratio of the polyethylene glycol compound to the N, N, N, N-tetramethyl ethylenediamine is (5-100) to 1.
2. The liquid embolic agent of claim 1, wherein the polyethylene glycol compound is polyethylene glycol diacrylate, 4-arm polyethylene glycol diacrylate, 8-arm polyethylene glycol diacrylate, 4-arm polyethylene glycol diacrylate, or 8-arm polyethylene glycol diacrylate.
3. The liquid embolic agent of claim 1, wherein the mass concentration of the polyethylene glycol compound in the liquid a is 2% to 40%.
4. A liquid embolic agent as in claim 1, wherein the persulfuric acid oxidizing agent is ammonium persulfate or sodium persulfate.
5. The liquid embolic agent of claim 1, wherein the mass concentration of the persulfate oxidizer in liquid a is 0.1-0.3%.
6. The liquid embolic agent of claim 1, wherein the mass concentration of N, N-tetramethylethylenediamine in the B liquid is 0.5% to 1.5%.
7. Use of a liquid embolic agent according to any of claims 1 to 6 for the preparation of an embolic agent, wherein liquid A and liquid B are separately withdrawn into syringes, and a double lumen microcatheter is used to connect the liquid A syringe to the liquid A and the liquid B syringe to the liquid B, respectively, and the liquid A and the liquid B are contacted and then cured to a hydrogel to effect embolization.
8. Use according to claim 7, wherein the syringe is pushed at the same speed.
9. The use of claim 7, wherein liquid A and liquid B cure to a hydrogel within 2-200 seconds of contact.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210179338.2A CN114533938A (en) | 2022-02-25 | 2022-02-25 | Liquid embolic agent and application thereof in preparation of embolic agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210179338.2A CN114533938A (en) | 2022-02-25 | 2022-02-25 | Liquid embolic agent and application thereof in preparation of embolic agent |
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| Publication Number | Publication Date |
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| CN114533938A true CN114533938A (en) | 2022-05-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202210179338.2A Pending CN114533938A (en) | 2022-02-25 | 2022-02-25 | Liquid embolic agent and application thereof in preparation of embolic agent |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114790661A (en) * | 2022-05-30 | 2022-07-26 | 上海益思妙医疗器械有限公司 | Method for dyeing polymer microspheres |
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| US20090164013A1 (en) * | 2007-12-21 | 2009-06-25 | Cruise Gregory M | Hydrogel filaments for biomedical uses |
| CN105916495A (en) * | 2013-11-08 | 2016-08-31 | 泰尔茂株式会社 | Polymer particles |
| US20160367731A1 (en) * | 2014-03-07 | 2016-12-22 | Endologix, Inc. | Method for forming hydrogels and materials therefor |
| US20190351107A1 (en) * | 2018-05-15 | 2019-11-21 | Incept, Llc | Embolic compositions and methods |
| CN113521378A (en) * | 2021-07-20 | 2021-10-22 | 上海益思妙医疗器械有限公司 | Preparation method of porous microspheres, microsphere embolic agent obtained by preparation method and application of microsphere embolic agent |
-
2022
- 2022-02-25 CN CN202210179338.2A patent/CN114533938A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090164013A1 (en) * | 2007-12-21 | 2009-06-25 | Cruise Gregory M | Hydrogel filaments for biomedical uses |
| CN105916495A (en) * | 2013-11-08 | 2016-08-31 | 泰尔茂株式会社 | Polymer particles |
| US20160367731A1 (en) * | 2014-03-07 | 2016-12-22 | Endologix, Inc. | Method for forming hydrogels and materials therefor |
| US20190351107A1 (en) * | 2018-05-15 | 2019-11-21 | Incept, Llc | Embolic compositions and methods |
| CN113521378A (en) * | 2021-07-20 | 2021-10-22 | 上海益思妙医疗器械有限公司 | Preparation method of porous microspheres, microsphere embolic agent obtained by preparation method and application of microsphere embolic agent |
Non-Patent Citations (1)
| Title |
|---|
| 薛巍，张渊明主编: "生物医用水凝胶", 暨南大学出版社, pages: 38 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114790661A (en) * | 2022-05-30 | 2022-07-26 | 上海益思妙医疗器械有限公司 | Method for dyeing polymer microspheres |
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