CN101962464B - Method for preparing calcium alginate microspheres with temperature response performance - Google Patents
Method for preparing calcium alginate microspheres with temperature response performance Download PDFInfo
- Publication number
- CN101962464B CN101962464B CN2010102923304A CN201010292330A CN101962464B CN 101962464 B CN101962464 B CN 101962464B CN 2010102923304 A CN2010102923304 A CN 2010102923304A CN 201010292330 A CN201010292330 A CN 201010292330A CN 101962464 B CN101962464 B CN 101962464B
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- CN
- China
- Prior art keywords
- temperature
- calcium alginate
- hexanolactam
- ethene hexanolactam
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 235000010410 calcium alginate Nutrition 0.000 title claims abstract description 18
- 239000000648 calcium alginate Substances 0.000 title claims abstract description 18
- 229960002681 calcium alginate Drugs 0.000 title claims abstract description 18
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 title claims abstract description 18
- 230000004044 response Effects 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title abstract description 10
- 239000004005 microsphere Substances 0.000 title abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 239000000661 sodium alginate Substances 0.000 claims abstract description 12
- 229940005550 sodium alginate Drugs 0.000 claims abstract description 12
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 235000010413 sodium alginate Nutrition 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004945 emulsification Methods 0.000 claims abstract description 7
- 239000000839 emulsion Substances 0.000 claims abstract description 5
- 239000003999 initiator Substances 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000012153 distilled water Substances 0.000 claims abstract description 4
- 238000009775 high-speed stirring Methods 0.000 claims abstract description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 16
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical group CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 3
- 238000006392 deoxygenation reaction Methods 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000009987 spinning Methods 0.000 claims description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- UZIQYDXSZVYYCF-UHFFFAOYSA-N azepan-2-one;ethene Chemical compound C=C.O=C1CCCCCN1 UZIQYDXSZVYYCF-UHFFFAOYSA-N 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004971 Cross linker Substances 0.000 abstract 1
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000001723 curing Methods 0.000 abstract 1
- 238000004108 freeze drying Methods 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 239000011521 glass Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002389 environmental scanning electron microscopy Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000004848 nephelometry Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AEMOLEFTQBMNLQ-AZLKCVHYSA-N (2r,3s,4s,5s,6r)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound O[C@@H]1O[C@@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-AZLKCVHYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-SYJWYVCOSA-N (2s,3s,4s,5s,6r)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-SYJWYVCOSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 239000011806 microball Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Description
Product | Embodiment 1 | Embodiment 2 | Embodiment 3 |
Phase transition temperature ℃ | 37.0 | 36.0 | 35.5 |
Claims (4)
Priority Applications (1)
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CN2010102923304A CN101962464B (en) | 2010-09-27 | 2010-09-27 | Method for preparing calcium alginate microspheres with temperature response performance |
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CN2010102923304A CN101962464B (en) | 2010-09-27 | 2010-09-27 | Method for preparing calcium alginate microspheres with temperature response performance |
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CN101962464A CN101962464A (en) | 2011-02-02 |
CN101962464B true CN101962464B (en) | 2012-05-30 |
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CN2010102923304A Expired - Fee Related CN101962464B (en) | 2010-09-27 | 2010-09-27 | Method for preparing calcium alginate microspheres with temperature response performance |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103191657B (en) * | 2013-04-02 | 2015-04-22 | 天津工业大学 | Hybridized gel film for filtration of organic solvent and preparation method thereof |
CN103224633B (en) * | 2013-04-02 | 2014-11-19 | 天津工业大学 | Self-reinforced hybrid hydrogel used for artificial muscles and preparation method thereof |
CN114377195A (en) * | 2021-12-30 | 2022-04-22 | 南京医科大学附属口腔医院 | Strontium alginate nano-microsphere and preparation method and application thereof |
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Publication number | Priority date | Publication date | Assignee | Title |
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US523090A (en) * | 1894-07-17 | Fastener for sash meeting-rails | ||
JP3589771B2 (en) * | 1996-01-24 | 2004-11-17 | 麒麟麦酒株式会社 | How to make alginate gel spheres |
CN101265332A (en) * | 2008-03-18 | 2008-09-17 | 天津大学 | Macro molecule engram polyvinylpyrrolidone/calcium alginate polymer micro-sphere and preparation method thereof |
CN101423564B (en) * | 2008-12-08 | 2011-05-04 | 青岛明月海藻集团有限公司 | Method for preparing alginate for fast preparation of hydrogel |
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Application publication date: 20110202 Assignee: QINGDAO FINEKING NEW MATERIALS CO.,LTD. Assignor: Qingdao University Contract record no.: 2013990000540 Denomination of invention: Method for preparing calcium alginate microspheres with temperature response performance Granted publication date: 20120530 License type: Exclusive License Record date: 20130829 |
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Assignee: QINGDAO FINEKING NEW MATERIALS CO.,LTD. Assignor: QINGDAO University Contract record no.: 2013990000540 Date of cancellation: 20220510 |
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