CN113336987A - Preparation method of natural high-strength sodium alginate double-crosslinked hydrogel film - Google Patents
Preparation method of natural high-strength sodium alginate double-crosslinked hydrogel film Download PDFInfo
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- 239000000017 hydrogel Substances 0.000 title claims abstract description 51
- 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 title claims abstract description 48
- 235000010413 sodium alginate Nutrition 0.000 title claims abstract description 48
- 239000000661 sodium alginate Substances 0.000 title claims abstract description 48
- 229940005550 sodium alginate Drugs 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 30
- 238000004132 cross linking Methods 0.000 claims abstract description 17
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims abstract description 13
- 239000012528 membrane Substances 0.000 claims abstract description 13
- 239000000499 gel Substances 0.000 claims abstract description 12
- 235000012209 glucono delta-lactone Nutrition 0.000 claims abstract description 12
- 229960003681 gluconolactone Drugs 0.000 claims abstract description 12
- 230000006196 deacetylation Effects 0.000 claims abstract description 11
- 238000003381 deacetylation reaction Methods 0.000 claims abstract description 11
- 229920000867 polyelectrolyte Polymers 0.000 claims abstract description 6
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910001424 calcium ion Inorganic materials 0.000 claims abstract description 5
- 229920002101 Chitin Polymers 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 238000009920 food preservation Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 5
- 239000002699 waste material Substances 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 230000003544 deproteinization Effects 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 230000008961 swelling Effects 0.000 abstract description 10
- 239000003431 cross linking reagent Substances 0.000 abstract description 4
- 230000003993 interaction Effects 0.000 abstract description 4
- 239000011159 matrix material Substances 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 239000011575 calcium Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000007547 defect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000002522 swelling effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229920001586 anionic polysaccharide Polymers 0.000 description 1
- 150000004836 anionic polysaccharides Chemical class 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
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- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- 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
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/246—Intercrosslinking of at least two polymers
-
- 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
- C08J2305/04—Alginic acid; Derivatives thereof
-
- 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
- C08J2405/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2401/00 or C08J2403/00
- C08J2405/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
Abstract
The invention discloses a preparation method of a natural high-strength sodium alginate double-crosslinked hydrogel film. The double-crosslinking hydrogel membrane takes sodium alginate as a matrix, deacetylated crab shell powder as a crosslinking agent, and gluconolactone as a calcium ion releasing agent in the crab shell powder to promote crosslinking of the sodium alginate gel. Meanwhile, amino groups exposed by deacetylation of chitin in the crab shell powder can generate polyelectrolyte interaction with carboxyl of sodium alginate, and a double-crosslinked hydrogel membrane is finally obtained. The double-crosslinked hydrogel film prepared by the invention has the advantages of simple preparation method, good swelling performance, high mechanical strength, environmental protection and the like. The hydrogel film can be used in the fields of medical health, bioengineering, food preservation and the like.
Description
Technical Field
The invention relates to a preparation method of a natural high-strength sodium alginate double-crosslinked hydrogel film, belonging to the field of green biopolymer materials.
Background
The hydrogel film is a novel polymer material, has the advantages of good sealing property, swelling property, degradability and the like, and is widely applied to the fields of biological medicine, tissue engineering, food packaging and the like. Hydrogel films are typically loaded with some active substance during application for sensing, delivery, release, etc. However, the traditional hydrogel film also has certain disadvantages, such as non-natural raw material source, complex preparation process, poor mechanical properties, low swelling ratio and the like. Therefore, the current research on hydrogels has focused mainly on the preparation method and the improvement of mechanical strength.
The hydrogel formation mechanisms are mainly ionic, chemical and physical crosslinking. Ionic crosslinking refers to the formation of three-dimensional network hydrogels through ionic interactions. The chemically crosslinked hydrogel is formed by constructing a highly crosslinked structure by forming a stable covalent bond on a matrix material under the action of an additional crosslinking agent or a catalyst, has good performance, but also has the cytotoxicity problem of the crosslinking agent, and is not beneficial to the application of the hydrogel. Physically cross-linked hydrogels are typically hydrogels formed by physical interactions (such as hydrogen bonding, chain entanglement, complexation, or polyelectrolyte interactions), are easy to use and have low toxicity, but have some reversibility and the resulting hydrogels have insufficient mechanical strength.
Sodium alginate is a safe natural anionic polysaccharide, has good moldability, and can be crosslinked with divalent metal cations to form a hydrogel film. Compared with other hydrogel materials, the sodium alginate hydrogel film is nontoxic and high in biocompatibility, and is widely applied to various biotechnology fields of gel tissue engineering of artificial bones and skins, drug delivery, wound dressing, packaging and the like. The preparation of sodium alginate hydrogel usually uses ion crosslinking as main material, and uses non-natural raw material such as calcium carbonate or calcium chloride solution as calcium source, wherein Ca is2+The hydrogel prepared by the method has the defects of nonuniform crosslinking, easy occurrence of local excessive crosslinking, poor mechanical property, low swelling rate, low strength of the formed hydrogel, difficulty in keeping the inherent shape in a hydrated state and easiness in cracking, and the defects seriously limit the application of the hydrogel. Therefore, there is a need to develop a sodium alginate hydrogel with high crosslinking strength to prevent the formation of a gelExpand the further application thereof.
Crab shell is a natural waste, the main components of which are 80 percent of calcium carbonate and 20 percent of chitin, and Ca released on one hand is obtained after crushing, deacetylation treatment and gluconolactone modification2+The chitosan can be crosslinked with sodium alginate, and on the other hand, the exposed amino group of the chitosan after deacetylation treatment can form polyelectrolyte interaction with the sodium alginate, so that a sodium alginate hydrogel membrane which is simple to prepare, green, uniform, good in swelling property and high in strength is obtained.
Disclosure of Invention
The invention aims to provide a green, high-strength and high-swelling sodium alginate double-crosslinked hydrogel membrane, which takes natural waste crab shells as a crosslinking initiator and aims to use gluconolactone as Ca2+Releasing agent prepared by adding Ca into crab shell powder2+The crab shell powder can form a polyelectrolyte compound with the sodium alginate after being subjected to deacetylation treatment, so that a double-crosslinked hydrogel film is formed, the defects of nonuniform crosslinking, low swelling property, poor mechanical property and the like of the traditional hydrogel film can be improved, and a foundation is laid for the research of the traditional hydrogel film in the fields of medical sanitation, bioengineering, food preservation and the like.
In order to achieve the purpose, the method comprises the following steps:
(1) carrying out superfine grinding on crab shell powder, adding a low-concentration sodium hydroxide solution, stirring for 6h at 60 ℃ for deproteinization, filtering and washing the obtained crab shell powder until the ph is 7, adding absolute ethyl alcohol, stirring for 6h at room temperature for decoloration, filtering and drying, adding a high-quality-fraction sodium hydroxide solution, stirring for 3h at 100 ℃ for deacetylation treatment, finally washing until the ph is neutral, and drying to obtain the deacetylated crab shell powder.
(2) Preparing a sodium alginate aqueous solution with the mass fraction of 2%, adding a certain amount of deacetylated crab shell powder after complete dissolution, adding glycerol for plasticization after uniform mixing, and stirring for 6h at room temperature.
(3) And stirring a certain amount of gluconolactone in the mixed solution of the sodium alginate and the partial deacetylated crab shell powder for 3min, pouring the mixture into a culture dish, drying for 7 days at room temperature, and balancing in a constant temperature and humidity box for 48h under the balancing condition of 20 ℃ and 50% relative humidity to obtain the natural high-strength sodium alginate double-crosslinked hydrogel membrane.
The invention also includes such features:
the mass fraction of sodium hydroxide used for deproteinization concentration in the step (1) is 5%, and the mass fraction of sodium hydroxide in the deacetylation treatment process is 33.7%. The particle size range of the finally obtained deacetylated crab shell powder is 0.125-33.95 μm, and the average particle size is 7.45 μm.
The mass ratio of the deacetylated crab shell powder, the glycerol and the sodium alginate added in the step (2) is 1:1: 2.
The mass fractions of the gluconolactone added in the step (3) are respectively 0.5%, 0.7% and 0.9%.
The performance of the sodium alginate double-crosslinking hydrogel membrane is characterized by adopting a laser particle size analyzer, a Fourier infrared spectrum, a swelling rate, swelling loss and gel strength.
The invention has the beneficial effects from the steps: firstly, the matrix sodium alginate selected for preparing the double-crosslinking hydrogel film is a biodegradable material, and has the advantages of no toxicity, high biocompatibility, high safety and the like. The invention uses the crab shell powder from nature as a double cross-linking agent, and deacetylates the crab shell powder, provides a calcium source for the ionic crosslinking of the sodium alginate hydrogel, promotes the sodium alginate and amino to form a polyelectrolyte compound, and increases the comprehensive utilization rate of agricultural byproducts. Thirdly, the invention uses glucolactone as Ca2+Releasing agents, H, dissociated after dissolving gluconolactone in water+Can slowly remove Ca in crab shell2+Released and then evenly cross-linked with sodium alginate to form an egg box structure, and the effect is better than that of other organic acids. And fourthly, a double cross-linked network structure is formed between the deacetylated crab shell powder and the sodium alginate, so that the mechanical strength of the membrane is far higher than that of a sodium alginate hydrogel membrane which is traditionally used in the fields of biological medicine, tissue engineering, food packaging and the like. Fifthly, the sodium alginate double-crosslinked hydrogel film is simple to prepare and has very high performanceHigh swelling capacity, and is superior to traditional sodium alginate hydrogel film.
Drawings
FIG. 1 average particle size diagram of deacetylated crab shell powder
FIG. 2 Fourier infrared spectrogram of sodium alginate double-crosslinked hydrogel film
FIG. 3 shows the gel strength of the hydrated double-crosslinked sodium alginate hydrogel film
FIG. 4 shows the gel content and swelling ratio of hydrogel films
Detailed Description
Example 1
A preparation method of a natural high-strength sodium alginate double-crosslinking hydrogel film comprises the following steps:
the method comprises the following steps: crushing waste crab shells by using an ultrafine crusher (the average particle size is 7.45 mu m), adding a 5% sodium hydroxide solution, stirring for 6h at 60 ℃ for deproteinization, filtering and washing the crab shell powder until the pH is neutral, adding absolute ethyl alcohol, stirring for 6h at room temperature for decoloration, filtering, and drying to obtain non-deacetylated crab shell powder. Fourier infrared spectrum result: 3698cm-1(hydrogen bond characteristic peak of chitin in crab shell powder), 3428cm-1(-OH vibration Peak), 2517cm-1 (CaCO3Characteristic peak of) 1425cm-1(-O asymmetric stretching peak), 873cm-1(CO3 2-In-plane bending vibration peak of) and 713cm-1(CO3 2-Out-of-plane bending vibration peak).
Adding the crab shell powder after purification treatment into 33.7% sodium hydroxide solution by mass fraction, reacting for 3h at 100 ℃ for deacetylation treatment, washing until ph is neutral, and drying to obtain deacetylated crab shell powder with average particle size of 7.45 μm. Fourier transform infrared spectrum at 3642cm-1A new peak appears due to the formation of new hydrogen bonds by the exposed amino groups after the deacetylation treatment.
Step two: dissolving a certain amount of sodium alginate in deionized water to obtain a sodium alginate water solution with the mass fraction of 2%. Then adding a certain amount of deacetylated crab shell powder and glycerol (m)Sodium alginate：mGlycerol：mCrab shell powder2:2:1) to obtain a uniform mixed solution.
Step three: adding 0.5 mass percent of gluconolactone into the film-forming solution. Stirring for 2min, pouring into a culture dish, drying at room temperature for 7 days, and balancing at 20 deg.C and 50% relative humidity for 48 hr to obtain natural high-swelling double-crosslinked hydrogel membrane. The example shows the following Fourier transform infrared spectrum: 3249cm-1Vibration peak corresponding to-OH, 1725cm-1Corresponding to characteristic peak of sodium alginate at 1598cm-1And 1409cm-1Corresponds to-COO–Symmetric and asymmetric stretching vibration peaks.
The Fourier transform infrared spectrum of example 1 is shown in FIG. 2, the gel strength is shown in FIG. 3, and the swelling ratio and gel content are shown in FIG. 4.
Example 2
This example is substantially identical to the process described in example 1, except that the gluconolactone is present in step three at a mass fraction of 0.7%. Fourier infrared spectrum result: 1596cm-1And 1410cm-1Corresponds to-COO–Symmetric and asymmetric stretching vibration peak of 3235cm-1The corresponding is the vibrational peak for-OH.
The Fourier transform infrared spectrum of example 2 is shown in FIG. 2, the gel strength is shown in FIG. 3, and the swelling ratio and gel content are shown in FIG. 4.
Example 3
This example is substantially identical to the process described in example 1, except that the gluconolactone is present in the third step at a mass fraction of 0.9%. Fourier infrared spectrum result: 1595cm-1And 1410cm-1Corresponds to-COO–Symmetrical and asymmetrical extension vibration peak of 3204cm-1The corresponding is the vibrational peak for-OH.
The Fourier transform infrared spectrum of example 3 is shown in FIG. 2, the gel strength is shown in FIG. 3, and the swelling ratio and gel content are shown in FIG. 4.
Claims (5)
1. The invention takes natural waste crab shells as a double-crosslinking initiator, and the main components of the initiator are calcium carbonate and chitin. On one hand, gluconolactone is used as a calcium ion releasing agent to promote the crosslinking of calcium ions in the crab shell powder and sodium alginate, on the other hand, the polyelectrolyte compound formed between the amino groups exposed in the crab shell powder after deacetylation treatment and the sodium alginate improves the hydrophobicity and the gel strength of the crab shell powder, and further the sodium alginate double-crosslinking hydrogel membrane is formed. The hydrogel film can be used in the fields of medical health, bioengineering, food preservation and the like.
2. The preparation method of the natural high-strength sodium alginate double-crosslinked hydrogel film according to claim 1 is characterized by comprising the following steps:
s1: crushing the waste crab shells by using an ultrafine crusher, collecting for later use, stirring for 6 hours at 60 ℃ in a low-concentration sodium hydroxide solution to remove protein, then filtering and washing until the pH value is neutral, adding absolute ethyl alcohol, stirring for 6 hours at room temperature to decolorize, filtering and drying, adding a high-concentration sodium hydroxide solution, stirring for 3 hours at 100 ℃ to perform deacetylation treatment, finally washing until the pH value is neutral, and drying to obtain deacetylated crab shell powder.
S2: preparing a sodium alginate aqueous solution with the mass fraction of 2%, stirring until the sodium alginate aqueous solution is completely dissolved, adding a certain amount of deacetylated crab shell powder, uniformly mixing, adding a proper amount of glycerol for plasticization, and stirring at room temperature for 6 hours.
S3: adding a certain amount of gluconolactone into the mixed solution of sodium alginate and deacetylated crab shell powder, stirring for 3min at room temperature, pouring into a culture dish, drying for 7 days at room temperature, and balancing in a constant temperature and humidity cabinet for 48h under the conditions of 20 ℃ and 50% relative humidity to obtain the natural high-strength sodium alginate double-crosslinked hydrogel membrane.
3. The method for preparing natural high-strength sodium alginate double-crosslinked hydrogel membrane as claimed in claim 2, wherein the mass fraction of sodium hydroxide used for deproteinization in S1 is 5%, and the mass fraction of sodium hydroxide used in deacetylation is 33.7%.
4. The preparation method of the natural high-strength sodium alginate double-crosslinked hydrogel membrane as claimed in claim 2, wherein the mass ratio of the sodium alginate, the glycerol and the deacetylated crab shell powder added in the S2 is 2:2: 1.
5. The method for preparing a natural high-strength sodium alginate double-crosslinked hydrogel film as claimed in claim 2, wherein the mass fractions of the gluconolactone added in the S3 are 0.5%, 0.7% and 0.9%, respectively.
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| CN113402734A (en) * | 2021-06-17 | 2021-09-17 | 东北农业大学 | Preparation method and application of hydrogel for indicating freshness of chilled meat |
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