CN110215411B - Broad-spectrum sunscreen composite nanoparticle and preparation method thereof - Google Patents
Broad-spectrum sunscreen composite nanoparticle and preparation method thereof Download PDFInfo
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Abstract
A preparation method of a broad-spectrum sunscreen composite nanoparticle comprises the step of encapsulating an organic sunscreen agent by a nano precipitation method through modified natural macromolecules, wherein the modified natural molecules comprise a hydrophobic part and a hydrophilic part, the hydrophilic part comprises carboxyl, amino and hydroxyl, and the hydrophobic part comprises phenylalanine esters, acrylic esters, coumarin, cinnamate and derivatives thereof. A plurality of organic sun-screening agents are encapsulated simultaneously by a simple and easy self-assembly method, and the composite nano particles with good light stability and broad-spectrum sun-screening function are obtained.
Description
Technical Field
The invention belongs to the technical field of chemistry, and relates to a broad-spectrum sunscreen composite nanoparticle
Technical Field
With the ozone layer being destroyed, radiation from the sun, especially UVA (320-400nm) and UVB (280-320nm), can reach the earth to a higher degree, causing different degrees of damage to human skin. Adverse reactions to solar ultraviolet rays include short-term inflammatory reactions such as erythema and edema, and long-term effects on skin photoaging, immunosuppression, skin cancer and the like. An effective way to block ultraviolet rays in the sun is to use sunscreen, and at present, increasing awareness of the harmful effects of ultraviolet rays has also prompted the use of sunscreen. Effective sunscreens can protect both UVA and UVB radiation and are known as broad spectrum sunscreens (280-400 nm).
Sunscreen cream mainly functions by means of sunscreen agents, and the sunscreen agents can be divided into organic sunscreen agents and inorganic sunscreen agents, wherein the inorganic sunscreen agents achieve a sunscreen effect by reflecting ultraviolet light, are opaque due to large particle size and thick, sticky and greasy, and are easy to agglomerate if nanometer inorganic sunscreen agents are used, so that skin feel is affected. In addition, the problem that cannot be ignored is that they have high catalytic activity and can cause damage to the skin, which limits their application in cosmetics. CN102675568A discloses a method for preparing organic-inorganic hybrid nanoparticles, which comprises the steps of preparing nanoparticles by self-assembly of synthesized triblock polymers, and then reducing a titanium precursor in situ to obtain organic-inorganic hybrid titanium dioxide nanoparticles, thereby effectively solving the problem of high catalytic activity of titanium dioxide. However, inorganic sunscreens have a limited uv protection wavelength range and are less protective.
The organic sunscreen agent can reduce the amount of ultraviolet rays reaching human skin by absorbing radiation in sunlight, has strong sunscreen capability, and can achieve a broad-spectrum sunscreen effect by selecting and combining. The organic sunscreen molecules absorb light and then typically dispose of the excitation energy in several ways, such as thermally, fluorescently, phosphorescing, interacting with neighboring molecules, or by light-induced decomposition, but the latter two ways of disposing of the excitation energy can reduce the uv protection of the sunscreen. Therefore, high stability is a prerequisite for the effectiveness of organic sunscreen products.
Encapsulation of organic sunscreens by polymeric nanoparticles can provide better photostability and safety. Wu et al prepared polymethyl methacrylate (PMMA) nanoparticles by a free radical emulsion polymerization process using Methyl Methacrylate (MMA) monomers, separately encapsulating organic sunscreens, improved their safety, sun protection index and photostability (Journal of Photochemistry & Photobiology B Biology,2014,131(6): 24). Yang et al prepared a nanoparticle encapsulating an organic sunscreen agent using polylactic acid-hyperbranched polyglycerol (PLA-HPG), reduced its permeability, and improved its photostability and UV absorption efficiency. (Nature Materials,2015,14(12):1278) but the above methods have problems of insufficient biocompatibility of the polymer or complicated preparation method of the nanoparticles, and do not achieve the effect of broad spectrum sunscreen.
Disclosure of Invention
Aiming at the problems, the invention provides a preparation method of broad-spectrum sunscreen composite nanoparticles. The method is based on modified natural macromolecules, and a plurality of organic sun-screening agents are encapsulated simultaneously by a simple and easy self-assembly method to obtain the composite nanoparticles with good light stability and broad-spectrum sun-screening function.
Aiming at the problem of poor light stability of the organic sun-screening agent, the modified natural macromolecules are used for encapsulating the organic sun-screening agent to obtain the composite nanoparticles, so that the light stability of the organic sun-screening agent is improved, and the sun-screening efficiency is improved.
The method comprises the following steps:
organic sunscreens are encapsulated by self-assembly by a nano precipitation method by using modified natural macromolecules, wherein the modified natural molecules comprise a hydrophobic part and a hydrophilic part, the hydrophilic part comprises carboxyl, amino and hydroxyl, and the hydrophobic part comprises phenylalanine esters, acrylic esters, coumarin, cinnamate and derivatives thereof.
Preferably, the modified natural macromolecule, organic sunscreen agent induces self-assembly upon dissolution in a solvent; the mass ratio of the modified natural macromolecules to the organic sunscreen agent is 5-20: 1.
Preferably, the method for inducing is adding NaCl water solution; the concentration of the NaCl aqueous solution is 0.05-0.1M.
Preferably, the natural macromolecules include gamma-polyglutamic acid, hyaluronic acid, chitosan, chitin, glucan, sodium alginate, starch, cellulose, pectin and other substances and derivatives thereof.
Preferably, the modified natural macromolecules comprise L-phenylalanine ethyl ester modified gamma-polyglutamic acid gamma-PGA-g-L-Phe, coumarin modified gamma-polyglutamic acid gamma-PGA-AMC, L-phenylalanine ethyl ester modified hyaluronic acid HA-Phe, caffeic acid modified glucan Dex-CA, dopamine modified gamma-polyglutamic acid gamma-PGA-DA, cinnamic acid modified glucan Dex-CINN, dodecyl glycidyl ether modified sodium alginate and dodecyl bromide modified chitosan.
Preferably, the modification comprises amidation, esterification, etherification, alkylation.
Preferably, the organic sunscreen agent comprises one or more UVA sunscreen agents and one or more UVB sunscreen agents.
Preferably, the UVA sunscreen comprises one or more of avobenzone, disodium phenyl dibenzoimidazole tetrasulfonate, troxaconazole trisiloxane, bis-ethylhexyloxyphenol methoxyphenyl triazine, and diethyl aminohydroxybenzoyl hexyl benzoate; the UVB sunscreen agent comprises ethylhexyl salicylate, benzophenone-3, benzophenone-4, benzophenone-5, homosalate, p-methoxycinnamate, 4-methylbenzylidene camphor, 3-benzylidene camphor, benzylidene camphor sulfonic acid, camphorbenzalkonium methyl sulfate, polyacrylamide methyl benzylidene camphor, ethylhexyl triazone, diethyl hexyl butamido triazone.
The organic sun-screening agent is encapsulated by self-assembly of modified natural macromolecules to prepare the composite nano particles, so that the photostability of the organic sun-screening agent is improved. Can be combined by a plurality of organic sunscreens to achieve the effect of broad-spectrum sunscreen. In addition, due to the excellent biocompatibility of the natural polymer, the composite nano particle has small irritation to human bodies and high safety. The composite nanoparticles can be used as a sunscreen agent in a sunscreen emulsion or cream formula.
An object of the present invention is to provide a wide spectrum sunscreen composite nanoparticle with good biocompatibility, which is prepared by any one of the above methods.
Preferably, the broad-spectrum sunscreen composite nanoparticle is applied to sunscreen emulsion and sunscreen cream related products.
Advantageous effects
The organic sunscreen agent uses natural macromolecules, has the advantages of wide sources, high safety, excellent biocompatibility and the like, and increases the safety of the organic sunscreen agent in the using process; the invention uses the self-assembly method to prepare the polymer composite nano particles, thereby overcoming the problem of complex preparation method of the nano particles in the prior art; the invention provides a composite nano particle of natural macromolecules with a broad-spectrum sunscreen function and an organic sunscreen agent, which can be suitable for different types of sunscreen agent systems (oil, emulsion and the like), can improve the light stability of the organic sunscreen agent and the sunscreen efficiency, has good broad-spectrum sunscreen performance, and can be used as a sunscreen agent in a sunscreen emulsion or cream formula.
Drawings
Fig. 1 is a transmission electron microscope photograph of the composite nanoparticle prepared in example 1.
Fig. 2(a) is a uv absorption diagram of three uv absorbers alone, and (b) is a uv absorption diagram of a broad-spectrum sunscreen composite nanoparticle prepared in example 1.
FIG. 3(a) is a chart listing the absorbance change before and after UV irradiation of the organic sunscreen agent, and (b) is a chart listing the absorbance change before and after UV irradiation of the composite nanoparticle using broad-spectrum sunscreen.
Detailed Description
The invention is further illustrated below with reference to specific embodiments. It is to be understood that the present invention is not limited to the following embodiments, which are regarded as conventional methods unless otherwise specified. The materials are commercially available from the open literature unless otherwise specified.
Example 1:
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3Adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; and dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain the amphiphilic polymer.
A broad spectrum sunscreen composite nanoparticle comprising the steps of:
100mg of L-phenylalanine ethyl ester-modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) was weighed out and dissolved in 10mL of DMSO to obtain 10mg mL of DMSO-1Then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate, adding the materials into the solution, fully dissolving the materials, and adding 10mL of 0.075M NaCl solution to induce the self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
As shown in fig. 1, the nanoparticles prepared in example 1 have a regular spherical structure, and the average particle diameter of the micelle is 80 nm. The broad-spectrum sunscreen composite nanoparticles provided by the invention have good dispersibility, have the advantages of regularity and uniform particle size in solving the problem of poor photostability, show that the encapsulated organic sunscreen doses are relatively consistent, and further, when the broad-spectrum sunscreen composite nanoparticles are used in a cream formula, the obtained product has relatively uniform sunscreen and high batch stability.
Example 2:
a composite nanoparticle of a broad spectrum sunscreen natural macromolecule and an organic sunscreen agent comprising the steps of:
100mg of L-phenylalanine ethyl ester-modified γ -polyglutamic acid (γ -PGA-g-L-Phe) (prepared in example 1) was weighed out and dissolved in 10mL of dimethyl sulfoxide (DMSO) to obtain 10mg mL of-1Then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate, adding the materials into the solution, fully dissolving the materials, and adding 10mL of 0.1M NaCl solution to induce the self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
Example 3:
a composite nanoparticle of a broad spectrum sunscreen natural macromolecule and an organic sunscreen agent comprising the steps of:
100mg of L-phenylalanine ethyl ester-modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) was weighed out and dissolved in 10mL of DMSO to obtain 10mg mL of DMSO-1Then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate, adding the materials into the solution, fully dissolving the materials, and adding 10mL of 0.15M NaCl solution to induce the self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
Example 4:
a composite nanoparticle of a broad spectrum sunscreen natural macromolecule and an organic sunscreen agent comprising the steps of:
50mg of L-phenylalanine ethyl ester-modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) was weighed out and dissolved in 10mL of DMSO to obtain 5mg mL of DMSO-1Then 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate are respectively weighed and added, after full dissolution, 10mL of 0.075M NaCl is addedInducing the self-assembly of the solution to obtain the broad-spectrum sunscreen composite nano particle.
Example 5:
a composite nanoparticle of a broad spectrum sunscreen natural macromolecule and an organic sunscreen agent comprising the steps of:
100mg of L-phenylalanine ethyl ester-modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) was weighed out and dissolved in 10mL of DMSO to obtain 10mg mL of DMSO-1Then 20mg of benzophenone-3, avobenzone and octyl methoxycinnamate are respectively weighed and added, after the solutions are fully dissolved, 10mL of 0.075M NaCl solution is added to induce the self-assembly of the solutions, and the broad-spectrum sunscreen composite nanoparticles are obtained.
Example 6:
a composite nanoparticle of a broad spectrum sunscreen natural macromolecule and an organic sunscreen agent comprising the steps of:
100mg of L-phenylalanine ethyl ester-modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) was weighed out and dissolved in 10mL of DMSO to obtain 10mg mL of DMSO-1Then respectively weighing 50mg of benzophenone-3, avobenzone and octyl methoxycinnamate, adding the materials into the solution, fully dissolving the materials, and adding 10mL of 0.075M NaCl solution to induce the self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
Example 7:
a composite nanoparticle of a broad spectrum sunscreen natural macromolecule and an organic sunscreen agent comprising the steps of:
100mg of L-phenylalanine ethyl ester-modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) was weighed out and dissolved in 10mL of DMSO to obtain 10mg mL of DMSO-1Respectively weighing 10mg of benzophenone-4, avobenzone and octyl methoxycinnamate, adding the materials into the solution, fully dissolving the materials, and adding 10mL of 0.075M NaCl solution to induce the self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
Example 8:
broad spectrum sunscreen performance study of broad spectrum sunscreen composite nanoparticles
The broad-spectrum sunscreen composite nanoparticle prepared in the embodiment 1 is dissolved in DMSO, diluted by 60-100 times, the maximum absorbance is controlled within 2, and ultraviolet spectrum scanning is carried out to measure the ultraviolet absorption condition within the range of 280-400 nm.
In example 8, as shown in FIG. 2(a), three organic sunscreens absorb in different ultraviolet bands, but have limited absorption ranges; as shown in (b), the prepared broad-spectrum sunscreen composite nanoparticle has good absorption in the whole UV wave band, and achieves the effect of broad-spectrum sunscreen.
Example 9:
photostability studies of broad-spectrum sunscreen composite nanoparticles
The broad-spectrum sunscreen composite nanoparticles prepared in example 1 were dissolved in DMSO, prepared to appropriate concentrations, and absorbance test was performed. Then, the copolymer solution was irradiated with a full-band ultraviolet lamp for 2 hours, and then subjected to an ultraviolet absorbance test.
In example 9, as shown in fig. 3, (b) column shows the absorbance change before and after uv irradiation of the composite nanoparticle using broad spectrum sunscreen, and compared with the non-encapsulated column (a), it can be concluded that: after encapsulation, the percentage of absorbance decrease before and after ultraviolet irradiation is reduced, which proves that the light stability is improved and the sun protection efficiency is improved.
Example 10:
use of broad spectrum sunscreen composite nanoparticles as sunscreen agents in sunscreen lotion or cream formulations
The formula is as follows: premixed phase (hydroxyethyl cellulose 3%, deionized water 2.5%); water phase (deionized water 63%, glycerol 8%, butylene glycol 30%, composite nanoparticles 2%); an oil phase (hydrogenated polyisobutene 5%, ethylhexyl palmitate 4%, polydimethylsiloxane 3%, caprylic/capric triglyceride 3%, ceteareth-211%, ceteareth-20.5%, butyl methoxydibenzoylmethane 0.5%, 4-methylbenzylidenecamphor 0.5%, phenoxyethanol 0.5%); adding the phase (water-soluble azone/PEG-40 hydrogenated castor oil 1%, vitamin E acetate 0.5%, nicotinamide 0.5%, triethanolamine 1%, essence 0.02%)
Firstly, uniformly mixing an oil phase raw material, a water phase raw material and a post-phase-adding raw material according to the content of each substance in a formula, then slowly heating the oil phase to 85 ℃, heating the water phase raw material to 70 ℃, slowly adding the water phase into the oil phase, stirring for 20min at 3000r/min, stopping heating and cooling to 45 +/-2 ℃, continuously stirring for 30min, adding the post-phase, homogenizing for 15min at 2000r/min, vacuumizing and defoaming, and cooling to 37 +/-2 ℃ under a stirring state to obtain the sunscreen cream. Adding the premixed phase, adding the oil phase under stirring, homogenizing at 6000r/min for 25min, stopping heating, cooling to 40 deg.C, adding the phase, homogenizing at 4000r/min for 10min, vacuum defoaming, stirring, and cooling to room temperature to obtain sunscreen cream.
The above is only a preferred embodiment of the present invention, and it should be noted that: it will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the principles of the invention and these are intended to be within the scope of the invention.
Claims (6)
1. A preparation method of broad-spectrum sunscreen composite nano particles is characterized in that,
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3, adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain an amphiphilic polymer;
a broad spectrum sunscreen composite nanoparticle comprising the steps of:
weighing 100mg of L-phenylalanine ethyl ester modified gamma-polyglutamic acid, dissolving the L-phenylalanine ethyl ester modified gamma-polyglutamic acid in 10mL of DMSO (dimethylsulfoxide) to obtain 10mg of a-1 solution, then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate, adding the 10mL of 0.075M NaCl solution after fully dissolving, and inducing self-assembly of the mixture to obtain the broad-spectrum sunscreen composite nanoparticles.
2. A preparation method of broad-spectrum sunscreen composite nano particles is characterized in that,
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3, adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain an amphiphilic polymer;
a broad spectrum sunscreen composite nanoparticle comprising the steps of:
weighing 100mg of L-phenylalanine ethyl ester modified gamma-polyglutamic acid, dissolving in 10mL of dimethyl sulfoxide to obtain 10mg of mL-1 solution, then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate, adding the obtained mixture into the solution, fully dissolving the obtained mixture, and adding 10mL of 0.1M NaCl solution to induce self-assembly of the obtained mixture to obtain the broad-spectrum sunscreen composite nanoparticles.
3. A preparation method of broad-spectrum sunscreen composite nano particles is characterized in that,
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3, adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain an amphiphilic polymer;
a broad spectrum sunscreen composite nanoparticle comprising the steps of:
weighing 100mg of L-phenylalanine ethyl ester modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) and dissolving in 10mL of DMSO to obtain 10mg mL-1 solution, then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate and adding the mixture into the solution, and after the mixture is fully dissolved, adding 10mL of 0.15M NaCl solution to induce self-assembly of the mixture to obtain the broad-spectrum sunscreen composite nanoparticles.
4. A preparation method of broad-spectrum sunscreen composite nano particles is characterized in that,
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3, adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain an amphiphilic polymer;
a broad spectrum sunscreen composite nanoparticle comprising the steps of:
weighing 50mg of L-phenylalanine ethyl ester modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) and dissolving in 10mL of DMSO to obtain 5mg of a-1 solution, then respectively weighing 10mg of benzophenone-3, avobenzone and octyl methoxycinnamate and adding the materials into the solution, and after the materials are fully dissolved, adding 10mL of 0.075M NaCl solution to induce self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
5. A preparation method of broad-spectrum sunscreen composite nano particles is characterized in that,
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3, adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain an amphiphilic polymer;
a broad spectrum sunscreen composite nanoparticle comprising the steps of:
weighing 100mg of L-phenylalanine ethyl ester modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) and dissolving the gamma-polyglutamic acid (gamma-PGA-g-L-Phe) in 10mL of DMSO to obtain 10mg of a solution of 1, then respectively weighing 50mg of benzophenone-3, avobenzone and octyl methoxycinnamate and adding the benzophenone-3, avobenzone and octyl methoxycinnamate into the solution, and after the solution is fully dissolved, adding 10mL of 0.075M NaCl solution into the solution to induce the self-assembly of the solution to obtain the broad-spectrum sunscreen composite nanoparticles.
6. A preparation method of broad-spectrum sunscreen composite nano particles is characterized in that,
preparation of modified natural macromolecules:
dissolving gamma-polyglutamic acid in NaHCO3, adding 1-1.5 equivalent of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide as a catalyst, activating for 5min, adding 1 equivalent of L-phenylalanine hexyl ester, reacting for 1h under an ice bath condition, and reacting for 12-24 h at room temperature; dialyzing in deionized water after the reaction is finished, and freeze-drying to obtain an amphiphilic polymer;
a broad spectrum sunscreen composite nanoparticle comprising the steps of:
weighing 100mg of L-phenylalanine ethyl ester modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) and dissolving the L-phenylalanine ethyl ester modified gamma-polyglutamic acid (gamma-PGA-g-L-Phe) in 10mL of DMSO to obtain 10mg of a solution of 10mg of mL-1, respectively weighing 10mg of benzophenone-4, avobenzone and octyl methoxycinnamate and adding the weighed materials into the solution, and after the materials are fully dissolved, adding 10mL of 0.075M NaCl solution into the solution to induce the self-assembly of the materials to obtain the broad-spectrum sunscreen composite nanoparticles.
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| CN111888282B (en) * | 2020-08-18 | 2021-08-13 | 江南大学 | Sunscreen composition containing ultraviolet-absorbable modified biomass, preparation method and application |
| CN112791010B (en) * | 2020-12-31 | 2022-05-24 | 华南理工大学 | Chestnut shell aerogel and preparation method and application thereof |
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