CN114085348B - Block copolymer, preparation method and application thereof - Google Patents
Block copolymer, preparation method and application thereof Download PDFInfo
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- CN114085348B CN114085348B CN202111448703.7A CN202111448703A CN114085348B CN 114085348 B CN114085348 B CN 114085348B CN 202111448703 A CN202111448703 A CN 202111448703A CN 114085348 B CN114085348 B CN 114085348B
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- Prior art keywords
- phbv
- solution
- polyethylene glycol
- block copolymer
- hexamethylene diisocyanate
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- 229920001400 block copolymer Polymers 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 210000000988 bone and bone Anatomy 0.000 claims abstract description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
- 239000000243 solution Substances 0.000 claims description 56
- 229920000520 poly(3-hydroxybutyrate-co-3-hydroxyvalerate) Polymers 0.000 claims description 39
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 35
- 239000002202 Polyethylene glycol Substances 0.000 claims description 34
- 229920001223 polyethylene glycol Polymers 0.000 claims description 34
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 13
- 239000011259 mixed solution Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 4
- 230000008439 repair process Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims 1
- 230000035876 healing Effects 0.000 abstract description 15
- 230000015556 catabolic process Effects 0.000 abstract description 3
- 238000006731 degradation reaction Methods 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000010586 diagram Methods 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- REKYPYSUBKSCAT-UHFFFAOYSA-N 3-hydroxypentanoic acid Chemical compound CCC(O)CC(O)=O REKYPYSUBKSCAT-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229920001427 mPEG Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000009818 osteogenic differentiation Effects 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WHBMMWSBFZVSSR-UHFFFAOYSA-M 3-hydroxybutyrate Chemical compound CC(O)CC([O-])=O WHBMMWSBFZVSSR-UHFFFAOYSA-M 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007490 hematoxylin and eosin (H&E) staining Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 210000000963 osteoblast Anatomy 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- 102100021238 Dynamin-2 Human genes 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 101000817607 Homo sapiens Dynamin-2 Proteins 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 210000003701 histiocyte Anatomy 0.000 description 1
- 238000010166 immunofluorescence Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 230000002188 osteogenic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- A61L27/18—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
- 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
- A61L27/58—Materials at least partially resorbable by the body
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4283—Hydroxycarboxylic acid or ester
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transplantation (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202111448703.7A CN114085348B (en) | 2021-11-30 | 2021-11-30 | Block copolymer, preparation method and application thereof |
Applications Claiming Priority (1)
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CN202111448703.7A CN114085348B (en) | 2021-11-30 | 2021-11-30 | Block copolymer, preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
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CN114085348A CN114085348A (en) | 2022-02-25 |
CN114085348B true CN114085348B (en) | 2023-03-03 |
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Family Applications (1)
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CN202111448703.7A Active CN114085348B (en) | 2021-11-30 | 2021-11-30 | Block copolymer, preparation method and application thereof |
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CN (1) | CN114085348B (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0859811A (en) * | 1994-08-10 | 1996-03-05 | Peter Neuenschwander | Biocompatible block copolymer |
CN107814896A (en) * | 2017-11-21 | 2018-03-20 | 深圳大学 | A kind of preparation method of polyurethane |
CN108690199A (en) * | 2018-05-24 | 2018-10-23 | 暨南大学 | A kind of block copolymer nano composite antibacterial material and the preparation method and application thereof |
CN109306048A (en) * | 2017-07-27 | 2019-02-05 | 天津科技大学 | A kind of preparation method for the PEG-b-PHBV polymer micelle loading resveratrol |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7985414B2 (en) * | 2003-02-04 | 2011-07-26 | Warsaw Orthopedic, Inc. | Polyurethanes for osteoimplants |
WO2019100196A1 (en) * | 2017-11-21 | 2019-05-31 | 深圳大学 | Polyurethane preparation method |
-
2021
- 2021-11-30 CN CN202111448703.7A patent/CN114085348B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0859811A (en) * | 1994-08-10 | 1996-03-05 | Peter Neuenschwander | Biocompatible block copolymer |
CN109306048A (en) * | 2017-07-27 | 2019-02-05 | 天津科技大学 | A kind of preparation method for the PEG-b-PHBV polymer micelle loading resveratrol |
CN107814896A (en) * | 2017-11-21 | 2018-03-20 | 深圳大学 | A kind of preparation method of polyurethane |
CN108690199A (en) * | 2018-05-24 | 2018-10-23 | 暨南大学 | A kind of block copolymer nano composite antibacterial material and the preparation method and application thereof |
Non-Patent Citations (3)
Title |
---|
生物基可降解聚氨酯的制备及结构与性能调控;王彩;《中国博士学位论文全文数据库 工程科技Ⅰ辑》;20170715(第07期);B016-5,参见5.3.3、6.5 * |
聚(3-羟基丁酸酯-co-3-羟基戊酸酯)的改性及其结构和性能的研究;周钰琦;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20191215(第12期);B014-111,参见第四章 * |
聚羟基烷酸酯嵌段共聚物复合抗菌材料的制备及性能研究;胡伟;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20181215(第12期);B020-306,参见第二章 * |
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CN114085348A (en) | 2022-02-25 |
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Inventor after: Zhang Weilin Inventor after: Zhang Zhiyu Inventor after: Zhao Wei Inventor after: Zhao Duoyi Inventor before: Zhang Zhiyu Inventor before: Zhang Weilin Inventor before: Zhao Wei Inventor before: Zhao Duoyi |
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Effective date of registration: 20231019 Address after: 524001 South 57, people's Road South, Xiashan District, Zhanjiang, Guangdong Patentee after: AFFILIATED HOSPITAL OF GUANGDONG MEDICAL University Address before: 110033 1-2, No. 4-32, Chongshan East Road, Huanggu District, Shenyang City, Liaoning Province Patentee before: Zhang Weilin |