CN113372540A - Polyellagic acid nanoparticles and method of making same - Google Patents
Polyellagic acid nanoparticles and method of making same Download PDFInfo
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- CN113372540A CN113372540A CN202110811799.2A CN202110811799A CN113372540A CN 113372540 A CN113372540 A CN 113372540A CN 202110811799 A CN202110811799 A CN 202110811799A CN 113372540 A CN113372540 A CN 113372540A
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- 239000002105 nanoparticle Substances 0.000 title claims abstract description 50
- 239000002253 acid Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229920002079 Ellagic acid Polymers 0.000 claims abstract description 58
- 229960002852 ellagic acid Drugs 0.000 claims abstract description 58
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 claims abstract description 39
- 235000004132 ellagic acid Nutrition 0.000 claims abstract description 39
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 239000007800 oxidant agent Substances 0.000 claims abstract description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 21
- 239000008367 deionised water Substances 0.000 claims description 17
- 229910021641 deionized water Inorganic materials 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 13
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- 238000000034 method Methods 0.000 claims description 12
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- 238000005119 centrifugation Methods 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 abstract description 9
- UMPKMCDVBZFQOK-UHFFFAOYSA-N potassium;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[K+].[Fe+3] UMPKMCDVBZFQOK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000012286 potassium permanganate Substances 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
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- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
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Abstract
The invention discloses a poly ellagic acid nanoparticle and a preparation method thereof. The invention uses hydrogen peroxide to replace concentrated sulfuric acid, potassium permanganate and potassium ferrate in the traditional preparation process as oxidants, solves the problems of serious environmental pollution, difficult recovery and the like caused by the use of the concentrated sulfuric acid, the potassium permanganate and the potassium ferrate oxidants, and simultaneously avoids the influence of the potassium ferrate oxidants on the color reaction of ellagic acid. The invention is suitable for preparing the poly-ellagic acid nanoparticles.
Description
Technical Field
The invention belongs to the technical field of biological materials, relates to a poly-ellagic acid, and particularly relates to a preparation method of a poly-ellagic acid nanoparticle.
Background
The ellagic acid monomer can form a poly-ellagic acid composite bioactive nano material through a polymerization reaction, the property of the poly-ellagic acid composite bioactive nano material is similar to that of the existing polyphenol nano material, and the poly-ellagic acid composite bioactive nano material has good biocompatibility and degradability. Compared with other phenolic nano materials, the phenolic nano material has the advantages of higher antioxidant bioactivity, good biological cell compatibility and the like, so that the phenolic nano material has stronger in-vivo free radical scavenging capacity, can effectively realize various physiological activity functions of reducing blood fat, absorbing ultraviolet rays, resisting cancers and tumors, sterilizing, deodorizing and the like, and simultaneously becomes one of important functional materials for research in the future due to simple and various preparation methods.
Research shows that when the concentration of the poly-ellagic acid nanoparticles is 2.7ug/mL, the ABTS (2, 2' -biazonitrogen-bis-3-ethylbenzothiazoline-6-sulfonic acid) free radical scavenging rate can reach 100%, the free radical scavenging capacity is stronger than that of nano materials such as poly-carotene, poly-lutein and poly-catechin, the poly-ellagic acid nanoparticles can be combined with substances such as protein, alkaloid and polysaccharide, and can be complexed with various metal ions. Therefore, the nano-composite material can be widely applied to surface modification of inorganic materials, nano-capsule medicines, nano-drug delivery systems and other advanced subjects, so that the nano-composite material has wide application prospects in the fields of foods, medicines, cosmetics, health products and the like.
However, the polyphenol nanoparticles widely used at present still have the defects of non-green and environment-friendly preparation method, low free radical scavenging activity, poor stability, low biological functionality and the like in the preparation process. In addition, the ellagic acid monomer commonly existing in pomegranate rind is not easy to dissolve in various solvents, so that the bioavailability is low, and the application range is limited.
Therefore, the preparation method of the poly-ellagic acid nanoparticles which are green and environment-friendly, high in free radical scavenging activity, good in stability and strong in biological functionality is very important.
Disclosure of Invention
The invention aims to provide a preparation method of a poly-ellagic acid nano particle which is green, environment-friendly, simple to operate and high in synthesis efficiency, so as to overcome the insolubility of an ellagic acid monomer and fully utilize the strong free radical scavenging activity and oxidation resistance of ellagic acid.
In order to achieve the purpose, the invention adopts the technical scheme that:
a preparation method of the poly ellagic acid nanoparticles comprises the following steps which are carried out in sequence:
s1, dissolving, diluting and centrifuging ellagic acid powder, and taking supernate to obtain a solution A;
s2, injecting a solution B formed by mixing alkali liquor, absolute ethyl alcohol, an oxidant and deionized water into the solution A, stirring, standing and centrifuging to obtain a precipitate C;
and S3, washing and drying the precipitate C to obtain the poly ellagic acid nanoparticles.
As a limitation, in the step S1, the solvent used for dissolving is any one of absolute ethyl alcohol, distilled water and alkali liquor, or a mixed solution of alkali liquor and absolute ethyl alcohol;
the alkali liquor is sodium hydroxide, potassium hydroxide or ammonia water solution, and the concentration is 0.08-0.15 mol/L.
As another limitation, in the step S1, the weight-to-volume ratio of the ellagic acid powder to the solvent is 1 g: 1-3L.
As a third limitation, in the step S1, the dilution factor is 8 to 15.
As a fourth limitation, in the step S1, the rotation speed during centrifugation is 6000-10000r/min, the temperature is 20-30 ℃, and the time is 10-15 min.
As a fifth limitation, in the step S2, the alkali solution is sodium hydroxide, potassium hydroxide, an ammonia solution, calcium hydroxide or sodium bicarbonate, and the concentration is 0.08-0.15 mol/L;
the oxidant is hydrogen peroxide solution with the concentration of 9-12 mol/L;
the volume ratio of the oxidant to the total amount of the absolute ethyl alcohol, the alkali liquor and the deionized water is 1: 1-40;
the volume ratio of the absolute ethyl alcohol to the alkali liquor to the deionized water is 1: 8-12: 25-35;
the molar ratio of the ellagic acid powder to the hydrogen peroxide is 1: 4000-.
As a sixth limitation, in the step S2, the stirring is performed by magnetic stirring, the rotation speed of the stirring is 1500-;
the standing time is 20-30 h;
the rotation speed of the centrifugation is 7000-10000r/min, the temperature is 20-30 ℃, and the time is 10-15 min.
As a seventh limitation, in the step S3, the washing manner is to wash 3 to 5 times with distilled water.
The present invention also provides a poly ellagic acid nanoparticle prepared according to the preparation method of any one of claims 1 to 8, having a particle size of 200-500 nm.
Due to the adoption of the technical scheme, compared with the prior art, the invention has the technical progress that:
the preparation method of the poly-ellagic acid nanoparticles provided by the invention uses hydrogen peroxide to replace concentrated sulfuric acid, potassium permanganate and potassium ferrate substances in the traditional preparation process as oxidants, and solves the problems of serious environmental pollution, difficult recovery and the like caused by the use of the concentrated sulfuric acid, potassium permanganate and potassium ferrate oxidants; meanwhile, the influence of the potassium ferrate oxidant on the color reaction of the ellagic acid is avoided;
the preparation method of the poly ellagic acid nanoparticles provided by the invention is simple to operate and high in synthesis efficiency, and solvents in the reaction process are deionized water and absolute ethyl alcohol, so that the solvent system is environment-friendly and does not bring secondary pollution;
the preparation method of the poly ellagic acid nanoparticles provided by the invention has no strict requirement on reaction temperature in the whole preparation process, does not need to be carried out at high temperature, reduces energy consumption, and obtains the poly ellagic acid nanoparticles with uniform particle size, controllable size, high stability and good dispersibility by controlling polymerization conditions.
The invention is suitable for preparing the poly-ellagic acid nanoparticles.
Drawings
The invention will be described in more detail with reference to the following figures and embodiments:
FIG. 1 is a schematic view of the nano-particles of ellagic acid prepared in example 1 of the present invention under a scanning electron microscope of 200 x;
FIG. 2 is a schematic view of 20-fold scanning electron microscope of the poly-ellagic acid nanoparticles prepared according to example 1 of the present invention;
FIG. 3 is a schematic view of 20-fold scanning electron microscope of the poly-ellagic acid nanoparticles prepared according to example 2 of the present invention;
fig. 4 is a schematic view of the poly ellagic acid nanoparticles prepared in example 2 of the present invention under a 100-fold scanning electron microscope.
Detailed Description
The present invention is further illustrated by the following specific examples, which are to be construed as merely illustrative, and not limitative of the remainder of the disclosure.
Example 1A method for preparing Polyellagic acid nanoparticles
The embodiment comprises the following steps which are carried out in sequence:
s1, dissolving 5mg of ellagic acid powder in 5ml of absolute ethyl alcohol, uniformly stirring, diluting 8 times with the absolute ethyl alcohol, continuously stirring until a uniform solution is obtained, centrifuging the solution for 15min at the temperature of 30 ℃ and the rotation speed of 8000r/min, and taking a supernatant to obtain a solution A1;
s2, the concentration of 10mL is9.5mol/L of H2O2Dissolving the mixture in 400mL of mixed solvent (the volume ratio of three solvents of ammonia water, absolute ethyl alcohol and deionized water is 1: 10: 30) compounded by 0.1mol/L ammonia water, absolute ethyl alcohol and deionized water to obtain solution B1;
s3, slowly adding the solution A1 into the solution B1, magnetically stirring for 40 minutes at the rotation speed of 5000r/min and the temperature of 32 ℃ until the reaction mixed liquid gradually changes from colorless to dark green, standing for 24 hours, and centrifuging for 15 minutes at the temperature of 30 ℃ and the rotation speed of 9000r/min to obtain a precipitate C1;
s4, washing the precipitate C1 with distilled water for 3 times, and drying to constant weight to obtain the poly-ellagic acid nano-particles D1;
s5, the poly ellagic acid nanoparticles D1 prepared in the S4 are placed under a scanning electron microscope for measurement, and the particle size of the poly ellagic acid nanoparticles D1 is measured to be 500 nm;
FIG. 1 is a schematic representation of a polyannic acid nanoparticle D1 under a 200-fold scanning electron microscope;
fig. 2 is a schematic representation of the polyannic acid nanoparticles D1 under a 20-fold scanning electron microscope.
Example 2A method for preparing Polyellagic acid nanoparticles
The embodiment comprises the following steps which are carried out in sequence:
s1, dissolving 1.5mg of ellagic acid powder in 4.5ml of distilled water, uniformly stirring, diluting by 10 times with distilled water, continuously stirring to obtain a uniform solution, centrifuging the solution at the temperature of 20 ℃ and the rotating speed of 6000r/min for 10min, and taking a supernatant to obtain a solution A2;
s2, adding 15mL of H with the concentration of 9mol/L2O2Dissolving the mixture in 500mL of mixed solvent (the volume ratio of the three solvents of sodium hydroxide solution, absolute ethyl alcohol and deionized water is 1: 8: 35) compounded by 0.08mol/L sodium hydroxide solution, absolute ethyl alcohol and deionized water to obtain solution B2;
s3, slowly adding the solution A2 into the solution B2, magnetically stirring for 30 minutes at the rotation speed of 1500r/min and the temperature of 35 ℃ until the reaction mixed liquid gradually changes from colorless to dark green, standing for 30 hours, and centrifuging for 10 minutes at the temperature of 28 ℃ and the rotation speed of 7000r/min to obtain a precipitate C2;
s4, washing the precipitate C2 with distilled water for 5 times, and drying to constant weight to obtain the poly-ellagic acid nano-particles D2;
s5, the poly ellagic acid nanoparticles D2 prepared in the S4 are placed under a scanning electron microscope for measurement, and the particle size of the poly ellagic acid nanoparticles is measured to be 400 nm;
FIG. 3 is a schematic representation of the poly ellagic acid nanoparticles D2 under a 20-fold scanning electron microscope;
fig. 4 is a schematic representation of the polyannic acid nanoparticles D2 under a 100-fold scanning electron microscope.
Example 3A method for preparing Polyellagic acid nanoparticles
The embodiment comprises the following steps which are carried out in sequence:
s1, dissolving 5mg of ellagic acid powder in 10ml of ammonia water with the concentration of 0.15mol/L, uniformly stirring, diluting by 15 times with the ammonia water with the concentration of 0.15mol/L, continuously stirring to obtain a uniform solution, centrifuging the solution for 12min at the temperature of 25 ℃ and the rotating speed of 7000r/min, and taking a supernatant to obtain a solution A3;
s2, 20mL of H with the concentration of 12mol/L2O2Dissolving the mixture in 600mL of a mixed solvent (the volume ratio of three solvents of ammonia water, absolute ethyl alcohol and deionized water is 1: 8: 25) compounded by 0.15mol/L ammonia water, absolute ethyl alcohol and deionized water to obtain a solution B3;
s3, slowly adding the solution A3 into the solution B3, magnetically stirring for 20 minutes at the rotation speed of 4000r/min and the temperature of 30 ℃ until the reaction mixed liquid gradually changes from colorless to dark green, standing for 28 hours, and centrifuging for 12 minutes at the temperature of 25 ℃ and the rotation speed of 9000r/min to obtain a precipitate C3;
s4, washing the precipitate C3 with distilled water for 4 times, and drying to constant weight to obtain the poly-ellagic acid nano-particles D3;
s5, the poly ellagic acid nanoparticles D3 prepared in S4 are placed under a scanning electron microscope for measurement, and the particle size of the poly ellagic acid nanoparticles D3 is measured to be 450 nm.
Example 4A method for preparing Polyellagic acid nanoparticles
The embodiment comprises the following steps which are carried out in sequence:
s1, dissolving 10mg of ellagic acid powder in 10ml of 0.08mol/L ammonia water solution, stirring uniformly, continuing to stir until the concentration of the ammonia water solution is 12 times that of the 0.08mol/L ammonia water solution, obtaining a uniform solution, centrifuging the solution for 14min at the temperature of 28 ℃ and the rotation speed of 10000r/min, and taking a supernatant to obtain a solution A4;
s2, adding 5mL of H with the concentration of 11mol/L2O2Dissolving the mixture in 300mL of mixed solvent (the volume ratio of the three solvents of sodium hydroxide solution, absolute ethyl alcohol and deionized water is 1: 12: 25) compounded by sodium hydroxide solution with the concentration of 0.08mol/L, absolute ethyl alcohol and deionized water to obtain solution B4;
s3, slowly adding the solution A4 into the solution B4, magnetically stirring for 5 minutes at the rotation speed of 3000r/min and the temperature of 40 ℃ until the reaction mixed liquid gradually changes from colorless to dark green, standing for 20 hours, and centrifuging for 14 minutes at the temperature of 20 ℃ and the rotation speed of 8000r/min to obtain a precipitate C4;
s4, washing the precipitate C4 with distilled water for 4 times, and drying to constant weight to obtain the poly-ellagic acid nano-particles D4;
s5, the poly ellagic acid nanoparticles D4 prepared in S4 are placed under a scanning electron microscope for measurement, and the particle size of the poly ellagic acid nanoparticles D4 is measured to be 400 nm.
Example 5A method for preparing Polyellagic acid nanoparticles
The embodiment comprises the following steps which are carried out in sequence:
s1, dissolving 20mg of ellagic acid powder in 60ml of mixed solvent which is prepared by compounding 0.1mol/L sodium hydroxide solution and absolute ethyl alcohol according to the volume ratio of 1:1, uniformly stirring, diluting by 9 times with the same mixed solvent, continuously stirring until uniform solution is obtained, centrifuging the solution for 11min at the temperature of 22 ℃ and the rotating speed of 9000r/min, and taking supernatant to obtain solution A5;
s2, adding 15mL of H with the concentration of 9.5mol/L2O2Dissolved in 550mL of 0.1mol/L sodium hydroxide solutionThe anhydrous ethanol and the deionized water are compounded into a mixed solvent (the volume ratio of the three solvents of the sodium hydroxide solution, the anhydrous ethanol and the deionized water is 1: 12: 35) to obtain a solution B5;
s3, slowly adding the solution A5 into the solution B5, magnetically stirring for 10 minutes at the rotation speed of 2000r/min and the temperature of 38 ℃ until the reaction mixed liquid is gradually changed from colorless to dark green, standing for 24 hours, and centrifuging for 13 minutes at the temperature of 30 ℃ and the rotation speed of 10000r/min to obtain a precipitate C5;
s4, washing the precipitate C5 with distilled water for 3 times, and drying to constant weight to obtain the poly-ellagic acid nano-particles D5;
s5, the poly ellagic acid nanoparticles D5 prepared in S4 are placed under a scanning electron microscope for measurement, and the particle size of the poly ellagic acid nanoparticles D5 is measured to be 500 nm.
Claims (9)
1. A preparation method of the poly ellagic acid nanoparticles is characterized by comprising the following steps which are carried out in sequence:
s1, dissolving, diluting and centrifuging ellagic acid powder, and taking supernate to obtain a solution A;
s2, injecting a solution B formed by mixing alkali liquor, absolute ethyl alcohol, an oxidant and deionized water into the solution A, stirring, standing and centrifuging to obtain a precipitate C;
and S3, washing and drying the precipitate C to obtain the poly ellagic acid nanoparticles.
2. The method of claim 1, wherein in step S1, the solvent used for dissolution is any one of absolute ethyl alcohol, distilled water and alkali solution, or a mixture of alkali solution and absolute ethyl alcohol;
the alkali liquor is sodium hydroxide, potassium hydroxide or ammonia water solution, and the concentration is 0.08-0.15 mol/L.
3. The method of claim 1 or 2, wherein in the step S1, the weight-to-volume ratio of the ellagic acid powder to the solvent is 1 g: 1-3L.
4. The method of claim 1 or 2, wherein the dilution factor in the step S1 is 8-15.
5. The method of claim 1 or 2, wherein the rotation speed of the centrifugation step S1 is 6000-10000r/min, the temperature is 20-30 ℃, and the time is 10-15 min.
6. The method of claim 1 or 2, wherein in the step S2, the alkali solution is sodium hydroxide, potassium hydroxide, ammonia solution, calcium hydroxide or sodium bicarbonate, and the concentration is 0.08-0.15 mol/L;
the oxidant is hydrogen peroxide solution with the concentration of 9-12 mol/L;
the volume ratio of the oxidant to the total amount of the absolute ethyl alcohol, the alkali liquor and the deionized water is 1: 1-40;
the volume ratio of the absolute ethyl alcohol to the alkali liquor to the deionized water is 1: 8-12: 25-35;
the molar ratio of the ellagic acid powder to the hydrogen peroxide is 1: 4000-.
7. The method of claim 1 or 2, wherein in step S2, the stirring is performed by magnetic stirring, the rotation speed of the stirring is 1500-;
the standing time is 20-30 h;
the rotation speed of the centrifugation is 7000-10000r/min, the temperature is 20-30 ℃, and the time is 10-15 min.
8. The method of claim 1 or 2, wherein the step S3 is performed by washing the particles with distilled water 3-5 times.
9. A polyannitic acid nanoparticle, characterized in that the polyannitic acid nanoparticle is prepared according to the preparation method of any one of claims 1-8, and has a particle size of 200-500 nm.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103273079A (en) * | 2013-05-10 | 2013-09-04 | 安徽医科大学 | Gold nanoflower preparing method and application of gold nanoflowers |
| CN105534926A (en) * | 2015-10-08 | 2016-05-04 | 东北林业大学 | Production technology of ellagic acid ultrafine powder |
| CN106925772A (en) * | 2017-04-17 | 2017-07-07 | 中国工程物理研究院化工材料研究所 | The preparation method of micro-/ nano composite material of core-shell structure |
| CN111004391A (en) * | 2019-11-21 | 2020-04-14 | 浙江大学 | Preparation method of size-controllable nano poly dopamine |
| CN111065633A (en) * | 2017-08-28 | 2020-04-24 | 株式会社Nbc纱网技术 | Process for producing polyphenol |
| CN112111535A (en) * | 2020-09-24 | 2020-12-22 | 四川大学 | Preparation method and application of antioxidant grape seed polyphenol nano material |
-
2021
- 2021-07-19 CN CN202110811799.2A patent/CN113372540B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103273079A (en) * | 2013-05-10 | 2013-09-04 | 安徽医科大学 | Gold nanoflower preparing method and application of gold nanoflowers |
| CN105534926A (en) * | 2015-10-08 | 2016-05-04 | 东北林业大学 | Production technology of ellagic acid ultrafine powder |
| CN106925772A (en) * | 2017-04-17 | 2017-07-07 | 中国工程物理研究院化工材料研究所 | The preparation method of micro-/ nano composite material of core-shell structure |
| CN111065633A (en) * | 2017-08-28 | 2020-04-24 | 株式会社Nbc纱网技术 | Process for producing polyphenol |
| CN111004391A (en) * | 2019-11-21 | 2020-04-14 | 浙江大学 | Preparation method of size-controllable nano poly dopamine |
| CN112111535A (en) * | 2020-09-24 | 2020-12-22 | 四川大学 | Preparation method and application of antioxidant grape seed polyphenol nano material |
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