CN103524764A - Preparation method of isolated soy protein macromolecular interpenetrating network hydrogel and application of hydrogel serving as medicine controlled release carrier - Google Patents
Preparation method of isolated soy protein macromolecular interpenetrating network hydrogel and application of hydrogel serving as medicine controlled release carrier Download PDFInfo
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Abstract
The invention discloses a preparation method of isolated soy protein macromolecular interpenetrating network hydrogel. The method comprises the steps as follows: isolated soy protein is dispersed in an alkaline solution, and monomer methacrylic acid-2-hydroxyl, a cross-linking agent of N,N'-methylene bisacrylamide and an initiator of potassium persulfate are added and mixed, so that the mixture is dissolved fully; under the protection of nitrogen, the temperature is raised to 40 DEG C and 80 DEG C, and a polymerization reaction is performed for 0.5-5 h; then a cross-linking agent of glutaraldehyde is added and stirred for 1-20 min, so that the cross-linking agent is dissolved; then a cross-linking reaction is performed for 0.5-9 h at the temperature of 40 DEG C-85 DEG C after the cross-linking agent is dissolved; and a cooling liquid is cooled to the room temperature, and the isolated soy protein is immersed in secondary water with ethanol, so that the isolated soy protein macromolecular interpenetrating network hydrogel with a unique topological network structure is obtained. Experiments show that, the isolated soy protein macromolecular interpenetrating network hydrogel has very good slow-release effects on micromolecular and macromolecular model medicines, so that the hydrogel can be applied to production of pharmaceutic preparations for medicine controlled release carriers.
Description
Technical field
The invention belongs to technical field of macromolecules, relate to a kind of preparation of soybean protein isolate polymer interpenetration network hydrogel; The present invention also relates to this polymer interpenetration network hydrogel as the application of medicine controlled release carrier simultaneously.
Background technology
Soybean protein isolate is to take a kind of full price protein foodstuff additive that low temperature desolventizing soybean meal is raw material production.In soybean protein isolate, protein content is more than 90%, and amino acid kind has nearly 20 kinds, and contains essential amino acid.It is nutritious, containing cholesterol, is one of kind of alternative animal proteinum few in number in vegetable-protein.According to settling ratio, soybean protein isolate can be divided into 2S, 7S, 11S and tetra-components of 15S, and wherein sphaeroprotein accounts for 50 ~ 90% of total protein.Soybean protein isolate mainly comprises glycinin (being often called 11S sphaeroprotein) and beta-conglycinin (being often called 7S) two class sphaeroprotein, account for 70% of total protein, they form by 17 seed amino acids, its chief component element is C, H, O, N, S, P and a small amount of Zn, Mg, Fe and Cu etc., by
,
,
form with tetra-kinds of subunits of γ.Nutritive Value of Soybean Proteins is high, has good emulsifying, gelation, tack etc., meanwhile, has the advantages such as degradable, pollution-free, environmental protection, thereby has huge potential using value.
Polymethyl acrylic acid-2-hydroxyl ethyl ester is as a kind of traditional biological basis material, there is good biocompatibility, its drug-loaded biological material has excellent biological function, can discharge medicine again, be that a kind of potential tissue engineering bracket material is gentle, controlled release drug solid support material, be widely used in the aspects such as dentures, medicament slow release, burn coating, organ transplantation, contact lense manufacture, cell cultures and biomolecules and enzyme immobilization.
Interpenetrating net polymer (IPN) is a kind of novel multiphase polymer material, it is mutually to be interted and form continuously by the network of gained after cross-linked polymer I and each self-crosslinking of cross-linked polymer II, there is unique topological framework and synergistic effect, can give full play to the advantage of polycomponent network, and control its morphological structure by synthetic method.
Summary of the invention
Object of the present invention, for the feature of prior art, provides a kind of preparation method of soybean protein isolate polymer interpenetration network hydrogel.
Another object of the present invention is to provide a kind of soybean protein isolate polymer interpenetration network hydrogel as the application of pharmaceutical carrier.
(1) preparation of soybean protein isolate polymer interpenetration network hydrogel
The preparation method of soybean protein isolate polymer interpenetration network hydrogel of the present invention, first soybean isolate protein powder to be scattered in alkaline solution, add monomer 2-hydroxyethyl methacrylate, linking agent N, N ＇-methylene-bisacrylamide, initiator potassium persulfate, stirs monomer, linking agent and initiator is fully dissolved; Under nitrogen protection, be warming up to 40 ~ 80 ℃ of post-polymerizations 0.5 ~ 5 hour; Add again and stir 1 ~ 20 min after linking agent glutaraldehyde it is dissolved, then crosslinking reaction 0.5 ~ 9 hour at 40 ~ 85 ℃; Reaction solution is cooled to room temperature, soaks successively respectively with ethanol, intermediate water, obtains soybean protein isolate polymer interpenetration network hydrogel.
The granularity of described soybean isolate protein powder is 50 ~ 100 orders; The mass ratio of soybean isolate protein powder and 2-hydroxyethyl methacrylate is 1:0.5 ~ 1:5.
Described alkaline solution adopts urea soln or the NaOH solution of concentration 1 ~ 10mol/L.
The consumption of described initiator potassium persulfate is 1 ~ 5% of soybean isolate protein powder quality; Linking agent N, the add-on of N ＇-methylene-bisacrylamide is 1 ~ 20% of soybean isolate protein powder quality; The add-on of linking agent glutaraldehyde is 10 ~ 100% of soybean isolate protein powder quality.
The hydrogel of above-mentioned preparation is filbert and molding effect is good.
(2) structure of soybean protein isolate polymer interpenetration network hydrogel, morphology characterization
Below by characterization methods such as infrared spectra (FT-IR), scanning electron microscope (SEM), surface functional group type, the structure and morphology of the synthetic soybean protein isolate interpenetrating network macromolecule hydrogel of the present invention are analyzed and researched.
Fig. 1 is the infrared spectrogram (FT-IR) of the soybean protein isolate interpenetrating network macromolecule hydrogel prepared of the present invention.Wherein, curve 1 is soybean protein isolate interpenetrating network macromolecule hydrogel, and curve 2 is soybean protein isolate, and curve 3 is polymethyl acrylic acid-2-hydroxyl ethyl ester homopolymer.As seen from Figure 1, at 1726cm
-1there is absorption more by force at place, is the C=O stretching vibration due to interpenetration network hydrogel ester carbonyl group, 1652cm
-1the absorption at place is due to acid amides one band, from the C=O stretching vibration absorption of amido linkage in protein, at 1541 cm
-1the absorption peak at place is acid amides two bands due to feature, from N-H flexural vibration, at 1250 cm
-1place is due to acid amides three bands, absorbs, at 1160cm from C-N stretching vibration
-1and 1080cm
-1it is the C-O stretching vibration due to 2-hydroxyethyl methacrylate homopolymer that there is stronger absorption peak at place.With Infrared Characterization 2-hydroxyethyl methacrylate homopolymer and interpenetrating network macromolecule hydrogel, the infrared spectrum of branch chain and 2-hydroxyethyl methacrylate homopolymer is basically identical, 1750cm
-1left and right-C=O stretching vibration peak, 1160cm
-1and 1080cm
-1left and right-C-O-stretching vibration peak, and more than 3000cm-1-O-H stretching vibration peak is all better corresponding.Illustrate between the starting material of prepared hydrogel and there is good consistency, formed inierpeneirating network structure.
Fig. 2 is the electron-microscope scanning (SEM) of 2-hydroxyethyl methacrylate and soybean protein isolate interpenetrating network macromolecule hydrogel.As can be seen from Figure 2, soybean protein isolate interpenetrating network macromolecule gel surface can be seen obvious network structure, has the inhomogenous cavernous structure of multi-level size, is conducive to the load of the different medicine of a large amount of molecular weight, illustrates that it has good drug carrying ability.
(3) drug carrying ability test
1, the drug carrying ability test to rhodamine B: dry hydrogel sample is positioned over to swelling in the rhodamine B aqueous solution and adsorbs 3 days, after swelling equilibrium, adopt ultraviolet-visible spectrum detect respectively the light absorption ratio of the rhodamine B aqueous solution before and after absorption and calculate drug loading, each sample do three times parallel.Experimental result: be 4.8% to the maximum drug loading of rhodamine B.
2, the drug carrying ability test to bovine serum albumin: dry hydrogel sample is positioned over to swelling in Bovine Serum Albumin in Aqueous Solution and adsorbs 3 days, after swelling equilibrium, adopt ultraviolet-visible spectrum detect respectively the light absorption ratio of Bovine Serum Albumin in Aqueous Solution before and after absorption and calculate drug loading, each sample do three times parallel.Experimental result: be 6.4% to the maximum drug loading of bovine serum albumin.
(4) the control release performance of soybean protein isolate interpenetrating network macromolecule hydrogel
1, to drug model small molecules (rhodamine B: release test RB)
Soybean protein isolate interpenetrating network macromolecule hydrogel lyophilize prepared by the present invention, dry hydrogel sample is positioned over to RB(1mg/mL) swelling absorption 3 days in the aqueous solution, after swelling equilibrium, after hydrogel surface after medicine carrying is rinsed, at 37 ℃, immerse 100 mL pH values and be respectively and in 3,7.4 and 8.4 PBS buffered soln (0.02mol/L), detect its release behavior.The content of the RB discharging in PBS buffered soln can adopt ultraviolet-visible spectrum to detect.Under certain hour interval, get 5 mL release medium and survey the absorbancy of RB, then add synthermal release medium that 5 mL are new and continue vibration and discharge, each sample do 3 times parallel, calculate accumulative total release rate.
Fig. 3 is soybean protein isolate IPN net height molecule network hydrogel of the present invention is the release profiles to rhodamine B in 3,7.4,8.4 buffered soln at pH, wherein, curve 1 is hydrogel release to rhodamine B in the buffered soln of pH=3, curve 2 is hydrogel release to rhodamine B in the buffered soln of pH=7.4, and curve 3 is hydrogel release to rhodamine B in the buffered soln of pH=8.4.The test result of Fig. 3 shows, macromolecule hydrogel of the present invention to all there being control release performance in the buffered soln of different pH values to rhodamine B, and after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4.
2, to drug model macromole (bovine serum albumin: release test BSA)
Soybean protein isolate polymer interpenetration network hydrogel lyophilize prepared by the present invention, dry hydrogel sample is positioned over to BSA(10mg/mL) swelling absorption 3 days in the aqueous solution, after swelling equilibrium, after hydrogel surface after medicine carrying is rinsed, at 37 ℃, immerse 100 mL pH values and be respectively and in 3,7.4 and 8.4 PBS buffered soln (0.02mol/L), detect its release behavior.The content of the BSA discharging in PBS buffered soln can adopt ultraviolet-visible spectrum to detect.Under certain hour interval, get 5 mL release medium and survey the absorbancy of BSA, then add synthermal release medium that 5 mL are new and continue vibration and discharge, each sample do 3 times parallel, calculate accumulative total release rate.
Fig. 4 is soybean protein isolate interpenetrating network macromolecule hydrogel of the present invention is the release profiles to bovine serum albumin in 3,7.4,8.4 buffered soln at pH, wherein, curve 1 is hydrogel release to bovine serum albumin in the buffered soln of pH=3, curve 2 is hydrogel release to bovine serum albumin in the buffered soln of pH=7.4, and curve 3 is hydrogel release to bovine serum albumin in the buffered soln of pH=8.4.The test result of Fig. 4 shows, soybean protein isolate polymer interpenetration network hydrogel of the present invention all has good control release performance in the buffered soln of different pH values to bovine serum albumin, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4.
In sum, the present invention utilizes the feature of 2-hydroxyethyl methacrylate and soybean protein isolate, the soybean protein isolate polymer interpenetration network hydrogel (SPI-PHEMA) of preparation all has good slow release effect to small molecules and macromole model drug, therefore can be used as medicine controlled release carrier for the production of pharmaceutical preparation.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram (FT-IR) of soybean protein isolate interpenetrating network macromolecule hydrogel of the present invention (SPI-PHEMA);
Fig. 2 is the electron-microscope scanning figure (SEM) of soybean protein isolate interpenetrating network macromolecule hydrogel of the present invention;
Fig. 3 is soybean protein isolate IPN net height molecule network hydrogel of the present invention is the release profiles to rhodamine B in 3,7.4,8.4 buffered soln at pH;
Fig. 4 is soybean protein isolate interpenetrating network macromolecule hydrogel of the present invention is the release profiles to bovine serum albumin in 3,7.4,8.4 buffered soln at pH.
Embodiment
Below by specific embodiment, the preparation of soybean protein isolate interpenetrating network macromolecule hydrogel of the present invention and medicine carrying and sustained release performance are described further.
Embodiment mono-
1, the preparation of soybean protein isolate interpenetrating network macromolecule hydrogel
0.1g soybean isolate protein powder (100 order) is well-dispersed in 10 mol/L sodium hydroxide solutions (5mL), 20 ℃ of stirrings, it is fully disperseed; Add 0.1 mL 2-hydroxyethyl methacrylate (0.1 g), after being uniformly mixed, add linking agent N, N ＇-methylene-bisacrylamide 0.01 g, potassium persulfate solution (Potassium Persulphate 0.01 g), stirs and makes its dissolving, then logical nitrogen protection, be warming up to 40 ℃, stirring reaction 0.5 h, then add glutaraldehyde 0.01 mL(0.01 g), continuing to stir 1.5 min makes, after its dissolving, to carry out crosslinking reaction 0.5 h at 40 ℃; Reaction solution is cooled to room temperature, respectively soaks 1h respectively with ethanol, intermediate water, obtains soybean protein isolate polymer interpenetration network hydrogel.
2, drug carrying ability test
(1) the drug carrying ability test to rhodamine B: dry hydrogel sample is positioned over to swelling in rhodamine B (0.5mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 2.5%.
(2) the drug carrying ability test to bovine serum albumin: dry hydrogel sample is positioned over to swelling in bovine serum albumin (5mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 4.9%.
3, control the mensuration of release performance
(1) the release performance test to rhodamine B
Testing method is with aforementioned.Test result: soybean protein isolate interpenetrating network macromolecule hydrogel all has control release performance in the buffered soln of different pH values to rhodamine B, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 66%.
(2) the release performance test to bovine serum albumin
Testing method is with aforementioned.Test result: soybean protein isolate interpenetrating network macromolecule hydrogel all has good control release performance in the buffered soln of different pH values to bovine serum albumin, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 65%.
Embodiment bis-
1, the preparation of soybean protein isolate interpenetrating network macromolecule hydrogel
0.1g soybean isolate protein powder (100 order) is well-dispersed in to (8 mL) in 5 mol/L sodium hydroxide solutions, 40 ℃ of stirrings, it is fully disperseed; Add 0.5 mL 2-hydroxyethyl methacrylate (0.5 g), after being uniformly mixed, add linking agent N, N ＇-methylene-bisacrylamide 0.05 g, potassium persulfate solution (Potassium Persulphate 0.02g), fully stirs monomer, linking agent and initiator is dissolved.Under logical nitrogen protection, be warming up to 50 ℃ of post-polymerization 1h, then add glutaraldehyde 0.02 mL(0.02 g), continue to stir 2 min and make its dissolving; Then at 50 ℃, carry out crosslinking reaction 1 h; Reaction solution is cooled to room temperature, respectively soaks 2 h respectively with ethanol, intermediate water, obtains soybean protein isolate polymer interpenetration network hydrogel.
2, drug carrying ability test
(1) the drug carrying ability test to rhodamine B: dry hydrogel sample is positioned over to swelling in rhodamine B (1.5mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 4.5%.
(2) the drug carrying ability test to bovine serum albumin: dry hydrogel sample is positioned over to swelling in bovine serum albumin (8mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 4.9%.
3, control the mensuration of release performance
(1) release performance to rhodamine B: soybean protein isolate/polymer interpenetration network hydrogel all has control release performance in the buffered soln of different pH values to rhodamine B, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 58%.
(2) release test to bovine serum albumin: soybean protein isolate/polymer interpenetration network hydrogel all has good control release performance in the buffered soln of different pH values to bovine serum albumin, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 69%.
Embodiment tri-
1, the preparation of soybean protein isolate interpenetrating network macromolecule hydrogel
0.1 g soybean isolate protein powder (100 order) is well-dispersed in to (10 mL) in 3 mol/L sodium hydroxide solutions, 50 ℃ of stirrings, it is fully disperseed, obtain soybean protein isolate dispersion liquid; Add 0.8 mL 2-hydroxyethyl methacrylate (0.8 g), after being uniformly mixed, add successively linking agent N, N ＇-methylene-bisacrylamide 0.08 g, potassium persulfate solution (Potassium Persulphate 0.03 g), fully stirs monomer, linking agent and initiator is dissolved.Under nitrogen protection, be warming up to 60 ℃ of post-polymerization 1.5 h, then add linking agent and enter glutaraldehyde 0.03 mL(0.03 g), continue to stir 2.5 min and make its dissolving; Then at 60 ℃, carry out crosslinking reaction 1.5 h; Reaction solution is cooled to room temperature, soaks 3 h respectively with ethanol, intermediate water, obtains soybean protein isolate polymer interpenetration network hydrogel.
2, drug carrying ability test
(1) the drug carrying ability test to rhodamine B: dry hydrogel sample is positioned over to swelling in rhodamine B (2.5mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 3.5%.
(2) the drug carrying ability test to bovine serum albumin: dry hydrogel sample is positioned over to swelling in bovine serum albumin (12mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 5.1%.
3, control the mensuration of release performance
(1) release performance to rhodamine B: soybean protein isolate/polymer interpenetration network hydrogel all has control release performance in the buffered soln of different pH values to rhodamine B, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 70%.
(2) release performance to bovine serum albumin: soybean protein isolate/polymer interpenetration network hydrogel all has good control release performance in the buffered soln of different pH values to bovine serum albumin, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 74%.
Embodiment tetra-
1, the preparation of soybean protein isolate interpenetrating network macromolecule hydrogel
0.1g soybean isolate protein powder (100 order) is well-dispersed in 1 mol/L urea soln (15mL), 60 ℃ of stirrings, it is fully disperseed; Add 1 mL 2-hydroxyethyl methacrylate (1g), after being uniformly mixed, add successively linking agent N, N ＇-methylene-bisacrylamide 0.01 g, potassium persulfate solution (Potassium Persulphate 0.04g), fully stirs and makes monomer, linking agent and initiator solution.Under nitrogen protection, be warming up to 70 ℃ of post-polymerization 3 h; Add again glutaraldehyde 0.04 mL(0.04g), continue to stir after 3 min, at 80 ℃, carry out crosslinking reaction 2 h; Reaction solution is cooled to room temperature, respectively with soaking 4h in ethanol, intermediate water, obtains soybean protein isolate interpenetrating network macromolecule hydrogel.
2, drug carrying ability test
(1) the drug carrying ability test to rhodamine B: dry hydrogel sample is positioned over to swelling in rhodamine B (3.5mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 4.8%.
(2) the drug carrying ability test to bovine serum albumin: dry hydrogel sample is positioned over to swelling in bovine serum albumin (14mg/ mL) aqueous solution and adsorbs 3 days, after swelling equilibrium, adopting ultraviolet-visible spectrum to detect and calculate drug loading is 6.4%.
3, control the mensuration of release performance
(1) release performance to rhodamine B: soybean protein isolate/polymer interpenetration network hydrogel all has control release performance in the buffered soln of different pH values to rhodamine B, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 67%.
(2) release performance to bovine serum albumin: soybean protein isolate/polymer interpenetration network hydrogel all has good control release performance in the buffered soln of different pH values to bovine serum albumin, after 12 h, release profiles tends to balance, and drug release has cumulative maximum release rate during pH=8.4, largest cumulative burst size can reach 78%.
Claims (8)
1. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel, first soybean isolate protein powder to be scattered in alkaline solution, add monomer 2-hydroxyethyl methacrylate, linking agent N, N ＇-methylene-bisacrylamide, initiator potassium persulfate, stirs monomer, linking agent and initiator is fully dissolved; Under nitrogen protection, be warming up to 40～80 ℃ of post-polymerizations 0.5～5 hour; Add again and stir 1～20 min after linking agent glutaraldehyde it is dissolved, then crosslinking reaction 0.5～9 hour at 40～85 ℃; Reaction solution is cooled to room temperature, soaks successively respectively with ethanol, intermediate water, obtains soybean protein isolate/polymer interpenetration network hydrogel.
2. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel as claimed in claim 1, is characterized in that: described soybean isolate protein powder be granularity 50～100 orders.
3. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel as claimed in claim 1 or 2, is characterized in that: the mass ratio of soybean isolate protein powder and 2-hydroxyethyl methacrylate is 1:0.5～1:5.
4. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel as claimed in claim 1 or 2, is characterized in that: described alkaline solution is urea soln or the aqueous sodium hydroxide solution of concentration 1～10 mol/L.
5. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel as claimed in claim 1 or 2, is characterized in that: the consumption of described initiator potassium persulfate is 1～5% of soybean isolate protein powder quality.
6. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel as claimed in claim 1 or 2, is characterized in that: linking agent N, the add-on of N ＇-methylene-bisacrylamide is 1～20% of soybean isolate protein powder quality.
7. the preparation method of soybean protein isolate/polymer interpenetration network hydrogel as claimed in claim 1 or 2, is characterized in that: the add-on of linking agent glutaraldehyde is 10～100% of soybean isolate protein powder quality.
As claimed in claim 1 soybean protein isolate/polymer interpenetration network hydrogel as the application of medicine controlled release carrier.
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| CN104927003A (en) * | 2015-06-29 | 2015-09-23 | 西北师范大学 | Preparation and application of soybean protein-base polymer gel with good biocompatibility and swelling ability |
| CN105017495A (en) * | 2015-06-29 | 2015-11-04 | 西北师范大学 | Preparation method of soybean protein-based dual-sensitive polymeric micro-porous gel, and application of gel as drug carrier |
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| CN111393370A (en) * | 2020-03-30 | 2020-07-10 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN111892907A (en) * | 2020-07-15 | 2020-11-06 | 广东省医疗器械研究所 | Albumin adhesive and preparation method thereof |
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| CN1669638A (en) * | 2004-12-31 | 2005-09-21 | 仲恺农业技术学院 | Modified soybean protein isolate base superpower water absorbent and preparation method thereof |
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| CN1669638A (en) * | 2004-12-31 | 2005-09-21 | 仲恺农业技术学院 | Modified soybean protein isolate base superpower water absorbent and preparation method thereof |
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| CN104927003A (en) * | 2015-06-29 | 2015-09-23 | 西北师范大学 | Preparation and application of soybean protein-base polymer gel with good biocompatibility and swelling ability |
| CN105017495A (en) * | 2015-06-29 | 2015-11-04 | 西北师范大学 | Preparation method of soybean protein-based dual-sensitive polymeric micro-porous gel, and application of gel as drug carrier |
| CN104927003B (en) * | 2015-06-29 | 2017-10-17 | 西北师范大学 | A kind of preparation and application of the soybean protein based high molecular gel with good biocompatibility and swelling behavior |
| CN105017495B (en) * | 2015-06-29 | 2017-11-10 | 西北师范大学 | A kind of preparation of soybean protein base dual-sensitivity high molecule micropore gel and the application as pharmaceutical carrier |
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| CN111393370A (en) * | 2020-03-30 | 2020-07-10 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN111393370B (en) * | 2020-03-30 | 2022-07-19 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN111892907A (en) * | 2020-07-15 | 2020-11-06 | 广东省医疗器械研究所 | Albumin adhesive and preparation method thereof |
| CN114752087A (en) * | 2022-04-21 | 2022-07-15 | 华南理工大学 | Soybean protein isolate-based organic gel and preparation method thereof |
| CN114752087B (en) * | 2022-04-21 | 2024-03-22 | 华南理工大学 | Soybean protein isolate-based organic gel and preparation method thereof |
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