CN109134886A - A kind of H2The preparation and application of S stimuli responsive hydrogel - Google Patents
A kind of H2The preparation and application of S stimuli responsive hydrogel Download PDFInfo
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- CN109134886A CN109134886A CN201810776922.XA CN201810776922A CN109134886A CN 109134886 A CN109134886 A CN 109134886A CN 201810776922 A CN201810776922 A CN 201810776922A CN 109134886 A CN109134886 A CN 109134886A
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- 239000000017 hydrogel Substances 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 229920001661 Chitosan Polymers 0.000 claims abstract description 18
- 239000000523 sample Substances 0.000 claims abstract description 17
- 238000001514 detection method Methods 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 10
- 230000000638 stimulation Effects 0.000 claims abstract description 4
- 239000000499 gel Substances 0.000 claims abstract 2
- 238000005406 washing Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 claims description 9
- 229960000907 methylthioninium chloride Drugs 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910001431 copper ion Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000011002 quantification Methods 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 229940079593 drug Drugs 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 4
- 238000004458 analytical method Methods 0.000 abstract description 3
- 238000013270 controlled release Methods 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract description 2
- 238000012544 monitoring process Methods 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- 229910052979 sodium sulfide Inorganic materials 0.000 description 4
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000001960 triggered effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 238000001903 differential pulse voltammetry Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 241000252506 Characiformes Species 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229910013868 M2SO4 Inorganic materials 0.000 description 1
- 241001481789 Rupicapra Species 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Electrochemistry (AREA)
- Molecular Biology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
本发明公开了一种H2S刺激响应水凝胶的制备及应用，所述方法是采用壳聚糖的分子链上含有大量氨基和羟基，能与Cu2+形成配位结构，触发壳聚糖形成稳定的水凝胶，且成胶迅速，约五秒内即可形成水凝胶。当环境中存在H2S时，能将水凝胶中的交联剂Cu2+竞争出来，导致水凝胶瓦解，释放水凝胶中包埋的探针，实现对H2S定量检测或药物可控释放；本发明方案操作简单、成本低、合成速度快且实施便利，其所制得的H2S刺激响应水凝胶性能稳定且不仅可用于H2S检测，还可用于在H2S刺激下进行药物的可控释放，另外在样品检测、食品安全分析、工业环境监测、药物释放材料等具有广阔应用前景。
The invention discloses the preparation and application of a H 2 S stimulus-responsive hydrogel. The method is that the molecular chain of chitosan contains a large number of amino groups and hydroxyl groups, which can form a coordination structure with Cu 2+ to trigger chitosan The sugar forms stable hydrogels that gel rapidly, forming hydrogels in about five seconds. When there is H 2 S in the environment, the cross-linking agent Cu 2+ in the hydrogel can be competed out, resulting in the disintegration of the hydrogel and the release of the probe embedded in the hydrogel, realizing the quantitative detection of H 2 S or Controllable drug release; the scheme of the invention is simple in operation, low in cost, fast in synthesis and convenient in implementation, and the prepared H 2 S stimuli-responsive hydrogel has stable performance and can not only be used for H 2 S detection, but also in H 2 S detection. The controlled release of drugs under the stimulation of 2 S has broad application prospects in sample detection, food safety analysis, industrial environmental monitoring, drug release materials, etc.
Description
Technical field
The present invention program is related to analytical chemistry field, and in particular to a kind of H2The preparation and application of S stimuli responsive hydrogel,
It can be used for H in sample2The detection of S and H2The release of the drug of S triggering.
Background technique
Hydrogel is a kind of macromolecule polymer material that can be swollen in water and have high-moisture.The material is logical
Cross active force (the effects of such as intermolecular electrostatic effect, hydrogen bond power) or the three-dimensional netted knot of formation of chemical bond between macromolecular chain
Structure.Research shows that the stimulation of some hydrogel energy sensing external environments, such as pH value, temperature, ionic strength, pressure, light, electricity, to be measured
The minor changes such as object cause hydrogel structure, energy state etc. to change and generate certain signal response.Based on height
The sensibility of the external boundary's environment of molecule hydrogel, researchers devise many functionalization stimuli responsive type macromolecule hydrogel materials
Material, constructs the sensor of object stimuli responsive, realizes the inspection of the species analysis such as metal ion, large biological molecule and cell
It surveys.
Chitosan is obtained after deacetylated processing by chitin, is that the most abundant natural alkalinity of content is more in nature
Sugar.Contain a large amount of amino and hydroxyl on the strand of chitosan, shell can be generated with many small molecules, ion or polymer reaction
The derivative or polymer composite of glycan base.Chitosan can be with other hydrophilic monomers by being physically or chemically crosslinked
Form formed have network macromolecule polymer material, wherein aquagel is the most common chitosan-based height
Molecular material.
Summary of the invention
The purpose of the present invention is to provide a kind of H2The preparation and application of S stimuli responsive hydrogel, can be used for environment sample
H in the scenes such as product, biological sample2The highly sensitive detection of S and the drug release triggered in H2S.
In order to realize above-mentioned technical purpose, the technical solution adopted by the present invention are as follows:
A kind of H2The preparation method of S stimuli responsive hydrogel comprising following steps:
(1) dissolved the chitosan in acetum according to the solid-to-liquid ratio of 1 g:200 mL, then it is ultrasonically treated with
The bubble to suspend in removal solution, obtained solution A；
(2) chemical probe is added into solution A, is then uniformly dispersed in solution A, obtained solution B；
(3) copper ion is added into solution B and is uniformly mixed, so that it is triggered chitosan monomer polymerization, hydrogel is made；
(4) after hydrogel obtained being carried out carrying out washing treatment, unpolymerized copper ion and extra chemical probe are removed
H is made2S stimuli responsive hydrogel.
Further, the mass percentage concentration of acetum is 0.2% in step (1).
Preferably, the additive amount of chitosan is 0.025 g in step (1), and the additive amount of acetum is 5 mL.
Preferably, the chemical probe in step (2) is the methylene blue of 1 mM, and additive amount is 20 μ L.
Further, the cleaning solution of the carrying out washing treatment in step (4) is distilled water.
Preferably, the number of carrying out washing treatment is 3 times in step (4).
It further, further include that free moisture is blotted with filter paper to the hydrogel after carrying out washing treatment in step (4).
According to H made from above-mentioned preparation method2One of application of S stimuli responsive hydrogel, by H obtained2S stimuli responsive
Hydrogel is used for H2The detection of S, specifically: H will be contained2The object to be detected of S is added to H2It is mixed in S stimuli responsive hydrogel
It closes, by H2Cu in S stimuli responsive hydrogel2+Competition displaces, and hydrogel is caused to be disintegrated, and the chemistry embedded in hydrogel is enabled to visit
Needle is released, and the chemical probe concentration released by detection detects the H of object to be detected come indirect quantification2S content.
According to H made from above-mentioned preparation method2One of application of S stimuli responsive hydrogel, by H obtained2S stimuli responsive
Embedding medicinal in hydrogel, then by its with contain H2After the material mixing of S, the release of embedding medicinal is realized.
According to H made from above-mentioned preparation method2One of application of S stimuli responsive hydrogel, by H obtained2S stimuli responsive
Hydrogel as external surface of objects coating, then by its with contain H2After the material mixing of S, the release of coated object is realized.
Using above-mentioned technical solution, the device have the advantages that are as follows: the present invention program is easy to operate, it is at low cost,
Aggregate velocity is fast and implements convenience, obtained by H2S stimuli responsive hydrogel performance is stable and cannot be only used for H2S detection, also
It can be used in H2The lower controlled release for carrying out drug of S stimulation, in addition sample detection, Food Safety Analysis, industrial environment monitoring,
Drug release material etc. has broad prospect of application.
Detailed description of the invention
The present invention is further elaborated with reference to the accompanying drawings and detailed description:
Fig. 1 is the brief preparation method schematic illustration of the present invention program；
Fig. 2 is H made from the present invention program2The stimuli responsive standard curve of S stimuli responsive hydrogel, wherein Fig. 2 (A) is under
Supreme a-j sequentially indicates that concentration is 1,5,10,15,25,40,60 μM of Na2S。
Specific embodiment
A kind of H2The preparation method of S stimuli responsive hydrogel comprising following steps:
(1) dissolved the chitosan in acetum according to the solid-to-liquid ratio of 1 g:200 mL, then it is ultrasonically treated with
The bubble to suspend in removal solution, obtained solution A；
(2) chemical probe is added into solution A, is then uniformly dispersed in solution A, obtained solution B；
(3) copper ion is added into solution B and is uniformly mixed, so that it is quickly triggered chitosan monomer polymerization, hydrogel is made；
(4) after hydrogel obtained being carried out carrying out washing treatment, unpolymerized copper ion and extra chemical probe are removed
H is made2S stimuli responsive hydrogel.
Contain a large amount of amino and hydroxyl, energy and Cu on the strand of the used chitosan of this programme2+Form coordination structure, touching
Hair chitosan forms stable hydrogel, and plastic is rapid, can form hydrogel in about five seconds.
When there are H in environment2It, can be by the crosslinking agent Cu in hydrogel when S2+Competition comes out, and hydrogel is caused to be disintegrated, release
The probe embedded in hydrogel is realized to H2S quantitative detection or drug controlled release.
Embodiment 1
As shown in Figure 1, a kind of H2The preparation method of S stimuli responsive hydrogel comprising following steps:
(1) 0.025 g chitosan is dissolved in the acetum that 5 mL mass concentrations are 0.2%, is then mixed by whirlpool
After chitosan is completely dissolved by device, then it is ultrasonically treated to remove the bubble to suspend in solution, obtained solution A；
(2) methylene blue solution of 20 μ L, 1 mM is added into solution A, is then uniformly dispersed in solution A, is made molten
Liquid B；
(3) it takes 300 μ L chitosans and methylene blue mixed liquor in 2 mL centrifuge tubes, Cu is added2+As hydrogel
Triggering agent, and mixed rapidly on eddy blending machine, chitosan aqueous solution enable to polymerize rapidly in 5 s, form hydrogel
(Cu-CS).；
(4) after hydrogel obtained being carried out carrying out washing treatment with distilled water, unpolymerized copper ion and extra methylene are removed
Base is blue, and then filter paper blots its surface progress moisture, can be prepared by H2S stimuli responsive hydrogel.
Test
Using Na2S is as H2The donor of S, and the Na of various concentration is obtained by diluted mode step by step2Then S standard items will
Above-mentioned standard product are using preceding ready-to-use.
By Na2S standard items are added to H obtained in embodiment2S stimuli responsive hydrogel (i.e. Cu-CS) hydrogel), pass through
Eddy blending machine mixes well the two, and placement is incubated at room temperature.At this point, Na2S and Cu-CS hydrogel generate competitive reaction,
Cu i.e. in hydrogel2+With S2-It reacts, generates CuS, Cu-CS hydrogel structure is caused to be disintegrated, discharge methylene blue.It incubates
After the completion of educating, supernatant is pipetted out using liquid-transfering gun, and by centrifuge separation CuS, retains the supernatant containing methylene blue
Liquid is to be measured.
This method is by measuring the concentration of methylene blue to the H in sample2S carries out quantitative detection.Methylene blue is fixed
Amount detection is carried out using differential pulse voltammetry (DPV).
Firstly, glass-carbon electrode (GCE, 3 mm) successively uses 1.0,0.3,0.05 μm of Al on chamois leather2O3Powder carries out
Polishing grinding, and be successively cleaned by ultrasonic using ethyl alcohol, Piranha washing lotion and distilled water.
Then, treated electrode is immersed in the H of 0.5 M2SO4In solution, using Ag/AgCl as reference electrode,
It using platinum filament as to electrode, is scanned in -0.2 ~ 1.0 V potential ranges using cyclic voltammetry, until being stablized
Cyclic voltammogram.GCE is completely spare with distilled water flushing.
Finally, GCE is placed in the above-mentioned prepare liquid containing methylene blue, quantitative detection is carried out to it using DPV method.Inspection
Survey condition are as follows: impulse amplitude: 0.05 V；Pulse width: 0.05 s；Potential range: -0.05 ~ 0.35 V.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent
With modification, covering scope of the invention is come under.
Claims (10)
1. a kind of H2The preparation method of S stimuli responsive hydrogel, it is characterised in that: it includes the following steps:
(1) dissolved the chitosan in acetum according to the solid-to-liquid ratio of 1 g:200 mL, then it is ultrasonically treated with
The bubble to suspend in removal solution, obtained solution A；
(2) chemical probe is added into solution A, is then uniformly dispersed in solution A, obtained solution B；
(3) copper ion is added into solution B and is uniformly mixed, hydrogel is made；
(4) after hydrogel obtained being carried out carrying out washing treatment, it can be prepared by H2S stimuli responsive hydrogel.
2. H according to claim 12The preparation method of S stimuli responsive hydrogel, it is characterised in that: acetic acid in step (1)
The mass percentage concentration of solution is 0.2%.
3. H according to claim 22The preparation method of S stimuli responsive hydrogel, it is characterised in that: shell is poly- in step (1)
The additive amount of sugar is 0.025 g, and the additive amount of acetum is 5 mL.
4. H according to claim 32The preparation method of S stimuli responsive hydrogel, it is characterised in that: the change in step (2)
The methylene blue that probe is 1 mM is learned, additive amount is 20 μ L.
5. H according to claim 12The preparation method of S stimuli responsive hydrogel, it is characterised in that: washing in step (4)
The cleaning solution for washing processing is distilled water.
6. H according to claim 52The preparation method of S stimuli responsive hydrogel, it is characterised in that: washing in step (4)
Number of processing is 3 times.
7. H according to claim 12The preparation method of S stimuli responsive hydrogel, it is characterised in that: step is also wrapped in (4)
It includes and free moisture is blotted with filter paper to the hydrogel after carrying out washing treatment.
8. according to claim 1 to H made from preparation method described in one of 72The application of S stimuli responsive hydrogel, feature exist
In: by H obtained2S stimuli responsive hydrogel is used for H2The detection of S, specifically: H will be contained2The object to be detected of S is added to H2S
It is mixed in stimuli responsive hydrogel, by H2Cu in S stimuli responsive hydrogel2+Competition displaces, and hydrogel is caused to be disintegrated,
Enable the chemical probe embedded in hydrogel be released, by detect the chemical probe concentration that releases come indirect quantification detect to
The H of detectable substance2S content.
9. the application of hydrogel is made to preparation method described in one of 7 according to claim 1, it is characterised in that: in H2S stimulation
Embedding medicinal in response water gel, then by its with contain H2After the material mixing of S, the release of embedding medicinal is realized.
10. the application of hydrogel is made to preparation method described in one of 7 according to claim 1, it is characterised in that: will be obtained
H2S stimuli responsive hydrogel as external surface of objects coating, then by its with contain H2After the material mixing of S, institute's coating is realized
The release of body.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108384069A (en) * | 2018-03-09 | 2018-08-10 | 广东工业大学 | A kind of metal coordination supramolecule hydrogel and preparation method thereof |
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| US20090324720A1 (en) * | 2008-04-22 | 2009-12-31 | Angiotech Pharmaceuticals, Inc. | Biocompatible crosslinked hydrogels, drug-loaded hydrogels and methods of using the same |
| KR20140045780A (en) * | 2012-10-09 | 2014-04-17 | 재단법인대구경북과학기술원 | Hydrogel and producing method of the same |
| CN106146913A (en) * | 2015-04-21 | 2016-11-23 | 南方科技大学 | Chitosan-based hydrogel and preparation method and application thereof |
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- 2018-07-14 CN CN201810776922.XA patent/CN109134886A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20090324720A1 (en) * | 2008-04-22 | 2009-12-31 | Angiotech Pharmaceuticals, Inc. | Biocompatible crosslinked hydrogels, drug-loaded hydrogels and methods of using the same |
| KR20140045780A (en) * | 2012-10-09 | 2014-04-17 | 재단법인대구경북과학기술원 | Hydrogel and producing method of the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108384069A (en) * | 2018-03-09 | 2018-08-10 | 广东工业大学 | A kind of metal coordination supramolecule hydrogel and preparation method thereof |
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