CN112321885B - Preparation and application of porous material assembled by graphene oxide and chitosan molecules - Google Patents
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Abstract
The invention discloses a porous material based on assembly of graphene oxide and chitosan molecules and a preparation method of the porous material based on assembly of graphene oxide and chitosan molecules. According to the invention, the cross-linking agent is used for cross-linking and compounding graphene and chitosan to prepare the hemostatic material, so that the mechanical strength of the chitosan macromolecule is improved, and the hemostatic performance and the bacteriostatic effect of the hemostatic material are also improved.
Description
Technical Field
The invention relates to the technical field of composite materials. More specifically, the invention relates to preparation and application of a porous material assembled by graphene oxide and chitosan molecules.
Background
Excessive blood loss caused by massive traumatic hemorrhage is an important cause of death and disability in wartime and clinic. The rapid hemostasis is one of the key measures for treating disabled people in war wound treatment and clinical treatment. Hemostatic materials achieve hemostasis primarily by forming a barrier to prevent the flow of blood. The good hemostatic material can effectively stop bleeding, protect the wound from being polluted and infected by dust particles, bacteria and viruses, provide a good healing environment for the wound and promote the wound to heal quickly. The development of a hemostatic material which can rapidly stop bleeding, prevent secondary infection and promote wound healing has very important practical application value. The general natural polymer has excellent biocompatibility and degradability, and the synthetic polymer has good physical and mechanical properties, processability and chemical stability. The polymer material has good controllability and high practicability, and has respective advantages and characteristics. Has wide application prospect in the use of medical materials.
The chitosan is a product of natural polysaccharide chitin with partial acetyl removed. As the only one of the natural polysaccharides, the chitosan has the biological safety performances of good biodegradability, biocompatibility, cell affinity, rapid coagulability and the like, and has very good air permeability and can be absorbed by human bodies. The chitosan surface has positive charges, so that red blood cells with negative charges are easy to gather on the surface of the chitosan, and meanwhile, the adhesion and the gathering of platelets can be enhanced, the formation of platelet thrombus is promoted, and the effect of blood coagulation is achieved. Chitosan can also activate complement system in blood, stimulate body reaction and supply blood in time while effectively stopping bleeding. The interaction between the positively charged groups on the chitosan molecules and the negatively charged groups on the bacterial cell wall can destroy the permeability of the bacterial cell wall, so that the peptidoglycan on the cell wall is hydrolyzed to inhibit the growth of bacteria; in addition, chitosan can form polymers around bacteria, effectively inhibit the material exchange between the bacteria and the external environment, and prevent the bacteria from absorbing nutrient substances, so the chitosan has certain inherent antibacterial performance, can be used as a hemostatic material to prevent wound infection and secondary infection, and can be used as a medicament for slowly releasing and carrying the antibody growth factor to stimulate and promote wound healing at an injured part. However, since many free amino groups are present in the chitosan polymer, many hydrogen bonds are present between and in the chitosan molecule, and the presence of these hydrogen bonds makes it difficult to dissolve chitosan, chitosan is only soluble under acidic conditions, but is hardly soluble in neutral or alkaline solvents. In addition, the structural characteristics of the chitosan macromolecule make the chitosan macromolecule have poor mechanical properties, and the normal use of the material cannot be ensured. And chitosan dissolved in acidic conditions is easy to swell again in an aqueous environment after removing water, so that the chitosan material is failed. Therefore, in the actual application process, the chitosan is often modified or compounded with other materials to obtain a composite chitosan material, so that the mechanical property, the solubility and the hemostatic property of the chitosan are improved. For example, the invention patent 201010291789.2 discloses a novel chitosan extraction method, which comprises the steps of self-preparing chitosan hemostatic sponge, freeze-drying to obtain porous hemostatic material which is easy to absorb, and animal experiments prove that the hemostatic material has excellent hemostatic performance. However, in practical application, the chitosan sponge prepared by directly using chitosan as a raw material has poor mechanical strength. The patent with application number 201210545888.8 discloses a porous hemostatic sponge prepared from chitosan and gelatin as main components, which solves the problem of poor mechanical strength, but is easily dissolved in a wound with massive bleeding and cannot play a blood coagulation role.
Disclosure of Invention
In order to solve the problems, the preparation of the hemostatic material by crosslinking and compounding chitosan by using a crosslinking agent and a small molecular material is a feasible technical means. The graphene oxide is a two-dimensional sheet structure which is composed of stable six-membered rings and has a large number of functional groups at the edges, and has good mechanical strength. The surface and the edge part of the graphene oxide structure contain a large number of oxygen-containing groups such as hydroxyl, carboxyl, epoxy groups and the like, and have high chemical activity. Generally, a water-soluble polymer structure has more free functional groups, graphene oxide is easy to react with active groups on the polymer to enhance the functionality of the polymer, and a benzene ring structure on the surface of the graphene oxide can also have pi-pi stacked non-covalent interaction with related groups, so that the mechanical property of the graphene oxide composite material can be improved to a great extent. The graphene oxide can conduct charges on the surface of bacteria, destroy physiological activities and functions of cell membranes, cause metabolic disorder of the bacteria, further promote bacterial death, has excellent antibacterial performance, has good biological properties such as cell compatibility and the like within a certain concentration range, and is widely applicable to medical materials.
The functional group on the surface of the graphene oxide and the free amino and hydroxyl in the molecular structure of the chitosan are self-assembled through hydrogen bonds and van der Waals force, the multiple hydrogen bond acting force among molecules and the two-dimensional molecular structure of the graphene oxide can greatly improve the mechanical strength of the chitosan, and the brittleness of the chitosan material cannot be caused. The graphene oxide micromolecules enter the chitosan macromolecules to form an interpenetrating network structure, oxygen-containing functional groups on the surfaces and the edge parts of the graphene oxide can act with free amino groups on the chitosan macromolecules so as to enhance the mechanical strength of the chitosan macromolecules, and the strong interaction between the cross-linking agent and the chitosan macromolecules can be "lubricated" so as to effectively prevent the brittleness caused by cross-linking. The graphene oxide can promote charge conduction between chitosan and bacteria, and synergistically increase the antibacterial performance of chitosan. The chitosan is embedded into the three-dimensional spongy chitosan material, so that the blood coagulation performance of the chitosan can be improved, the healing of wounds is promoted, and the hemostatic efficiency of the hemostatic material is improved. Carboxyl grafted on the surface of the graphene oxide can be complexed with iron ions in red blood cells to form blood clots, and the hemostasis performance of the graphene oxide is improved by the cooperation with chitosan.
The use of the cross-linking agent can not only improve the mechanical strength of the chitosan macromolecule to a great extent, but also avoid the swelling of the chitosan acid solution after freeze-drying, and can not influence the liquid absorption performance of the cross-linked graphene oxide-chitosan hemostatic material. Meanwhile, the cross-linked graphene oxide-chitosan hemostatic material has excellent antibacterial performance.
The invention also aims to provide a porous material based on the assembly of graphene oxide and chitosan molecules and a preparation method of the porous material based on the assembly of graphene oxide and chitosan molecules. The preparation method is simple to operate, the preparation cost is extremely low, and the preparation process is environment-friendly and does not need to treat any waste. The prepared cross-linked graphene oxide-chitosan porous material has excellent antibacterial performance and hemostatic performance.
To achieve these objects and other advantages and in accordance with the purpose of the invention, as embodied and broadly described herein, there is provided a method for preparing a porous material based on graphene oxide and chitosan molecular assembly, comprising the steps of adding an aqueous solution of graphene oxide into an aqueous dispersion of chitosan to perform interfacial self-assembly, adding a cross-linking agent to react, adding an acid solution to treat, and freeze-drying to obtain a cross-linked graphene oxide-chitosan porous material.
Preferably, the mass ratio of the graphene oxide in the graphene oxide aqueous solution to the chitosan in the chitosan aqueous dispersion is 0.03-0.1: 1;
the content of the graphene oxide in the graphene oxide aqueous solution is 2-10 mg/mL.
Preferably, the ratio of chitosan to the cross-linking agent in the chitosan aqueous dispersion is 30-200 g: 1 ml.
Preferably, after the cross-linking agent is added, the reaction is stirred at the speed of 100-300 rppm for 10-50 min and at the temperature of 15-35 ℃;
the cross-linking agent is one or more of glutaraldehyde, formaldehyde, glyoxal and 2, 4-pentanedione.
Preferably, after the acid solution is added, the stirring speed of the treatment is 500-1200 rppm, the time is 5-30 h, and the temperature is 25-45 ℃;
the volume ratio of the acid solution to the chitosan aqueous dispersion is 0.01-0.025: 1;
the acid solution is one of glacial acetic acid, concentrated hydrochloric acid, concentrated nitric acid and oxalic acid.
Preferably, the deacetylation degree of chitosan in the chitosan aqueous dispersion is more than or equal to 85%.
The porous material based on the assembly of the graphene oxide and the chitosan molecules is prepared by using the preparation method of the porous material based on the assembly of the graphene oxide and the chitosan molecules.
The hemostatic material is prepared from a porous material based on graphene oxide and chitosan molecular assembly.
An application of a porous material assembled by graphene oxide and chitosan molecules in preparation of a hemostatic material.
The invention at least comprises the following beneficial effects:
the invention adopts graphene oxide and glutaraldehyde to crosslink the chitosan material together under an acidic condition to obtain the crosslinked graphene oxide-chitosan hemostatic material. Glutaraldehyde can react with free amino groups on chitosan molecules to perform Schiff base crosslinking, so that the mechanical property of the chitosan is improved, and the solubility of the chitosan is changed. The oxygen-containing groups such as carboxyl, hydroxyl and the like on the surface and the edge of the graphene oxide effectively act on the chitosan, so that the mechanical property of the chitosan can be further improved, the brittleness of glutaraldehyde cross-linked chitosan can be improved, and the graphene oxide can cooperate with the chitosan to improve the blood coagulation property. The prepared hemostatic material has excellent antibacterial performance and can quickly stop bleeding in a short time.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a schematic scanning electron microscope illustration of the porous material of example 1 of the present invention.
Detailed Description
The present invention is further described in detail below with reference to examples so that those skilled in the art can practice the invention with reference to the description.
It is to be noted that the experimental methods described in the following embodiments are all conventional methods unless otherwise specified, and the reagents and materials are commercially available unless otherwise specified.
< example 1>
A preparation method of a porous material based on graphene oxide and chitosan molecule assembly specifically comprises the following steps:
step one, dispersing 2g of chitosan with deacetylation degree of 96.2% in 80mL of deionized water at a stirring speed of 200rppm, and stirring for 8min to obtain a chitosan water dispersion;
step two, adding 20mL of graphene oxide aqueous solution with the concentration of 10mg/mL into the chitosan aqueous dispersion under continuous stirring, after 10min, adding 10 mu L of glutaraldehyde serving as a cross-linking agent, and continuously stirring for 50min under the conditions of 15 ℃ and 300rppm to obtain the cross-linked graphene oxide-chitosan aqueous dispersion;
and step three, adding 1mL of glacial acetic acid into the crosslinked graphene oxide-chitosan aqueous dispersion, continuously stirring for 10h at 25 ℃ and 1000rppm to obtain a uniform crosslinked graphene oxide-chitosan solution, and freeze-drying to obtain the spongy porous material.
< example 2>
A preparation method of a porous material based on graphene oxide and chitosan molecule assembly specifically comprises the following steps:
step one, dispersing 3g of chitosan with deacetylation degree of 96.5% in 80mL of deionized water at a stirring speed of 300rppm, and stirring for 8min to obtain a chitosan water dispersion;
step two, taking 20mL of graphene oxide aqueous solution with the concentration of 5mg/mL, adding the graphene oxide aqueous solution into the chitosan aqueous dispersion under continuous stirring, after 10min, adding 100 mu L of glyoxal as a cross-linking agent, and continuously stirring for 40min under the conditions of 35 ℃ and 100rppm to obtain the cross-linked graphene oxide-chitosan aqueous dispersion;
and step three, adding 2mL of oxalic acid into the crosslinked graphene oxide-chitosan aqueous dispersion, continuously stirring for 5h at 45 ℃ under 1200rppm to obtain a uniform crosslinked graphene oxide-chitosan solution, and freeze-drying to obtain the spongy porous material.
< example 3>
A preparation method of a porous material based on graphene oxide and chitosan molecule assembly specifically comprises the following steps:
step one, dispersing 2g of chitosan with deacetylation degree of 86.5% in 80mL of deionized water at a stirring speed of 200rppm, and stirring for 8min to obtain a chitosan water dispersion;
step two, taking 20mL of graphene oxide aqueous solution with the concentration of 5mg/mL, adding the graphene oxide aqueous solution into the chitosan aqueous dispersion under continuous stirring, adding 50 mu L of formaldehyde serving as a cross-linking agent after 10min, and continuously stirring for 30min under the conditions of 25 ℃ and 200rppm to obtain the cross-linked graphene oxide-chitosan aqueous dispersion;
and step three, adding 2mL of concentrated hydrochloric acid into the crosslinked graphene oxide-chitosan aqueous dispersion, continuously stirring for 24h at 35 ℃ under 500rppm to obtain a uniform crosslinked graphene oxide-chitosan solution, and freeze-drying to obtain the spongy porous material.
< example 4>
A preparation method of a porous material based on graphene oxide and chitosan molecule assembly specifically comprises the following steps:
step one, dispersing 2g of chitosan with deacetylation degree of 90.5% in 80mL of deionized water at a stirring speed of 200rppm, and stirring for 8min to obtain a chitosan water dispersion;
step two, adding 20mL of graphene oxide aqueous solution with the concentration of 6mg/mL into the chitosan aqueous dispersion under continuous stirring, adding 50 mu L of 2, 4-pentanedione serving as a cross-linking agent after 10min, and continuously stirring for 20min under the conditions of 35 ℃ and 250rppm to obtain the cross-linked graphene oxide-chitosan aqueous dispersion;
and step three, adding 1mL of concentrated nitric acid into the crosslinked graphene oxide-chitosan aqueous dispersion, continuously stirring for 30h at 30 ℃ under 800rppm to obtain a uniform crosslinked graphene oxide-chitosan solution, and freeze-drying to obtain the spongy porous material.
< example 5>
A preparation method of a porous material based on graphene oxide and chitosan molecule assembly specifically comprises the following steps:
step one, dispersing 3g of chitosan with the deacetylation degree of 92.5% in 80mL of deionized water at the stirring speed of 250rppm, and stirring for 8min to obtain a chitosan water dispersion;
step two, adding 20mL of graphene oxide aqueous solution with the concentration of 8mg/mL into the chitosan aqueous dispersion under continuous stirring, adding 50 mu L of 2, 4-pentanedione serving as a cross-linking agent after 10min, and continuously stirring for 10min under the conditions of 35 ℃ and 300rppm to obtain the cross-linked graphene oxide-chitosan aqueous dispersion;
and step three, adding 1mL of concentrated nitric acid into the crosslinked graphene oxide-chitosan aqueous dispersion, continuously stirring for 30 hours at the temperature of 30 ℃ and at the rppm of 800 to obtain a uniform crosslinked graphene oxide-chitosan solution, and freeze-drying to obtain the spongy porous material. The spongy porous material can be formed in a polytetrafluoroethylene mold to prepare the spongy porous material with the specification. The mould specification is disc 60mm in diameter, height 8 mm.
< example 6>
The sponge-like porous material obtained in the examples 1 to 5 was compacted and covered with a support protective film to obtain a hemostatic material.
< comparative example 1>
The difference between the comparative example 1 and the example 1 is that the crosslinking agent glutaraldehyde is not added, and the other steps are the same as the example 1, so that the graphene oxide-chitosan sponge freeze-dried material without the crosslinking agent is obtained.
< comparative example 2>
The difference between the comparative example 2 and the example 1 is that the amount of deionized water is 100mL, no graphene oxide aqueous solution is added, and other steps are the same as those of the example 1, so that the glutaraldehyde-crosslinked chitosan sponge freeze-dried material is obtained.
< comparative example 3>
The difference between comparative example 3 and example 1 is that the order of adding acid solution is adjusted, and the order of adding glacial acetic acid in step three is advanced, that is, 1ml of glacial acetic acid is added into chitosan aqueous dispersion and stirred and mixed, and then graphene oxide aqueous solution is added into chitosan aqueous dispersion containing concentrated hydrochloric acid, and other steps are the same as example 1.
< testing of porous Material >
The hemostatic performance and the bacteriostatic effect of the samples of examples 1 to 5 and comparative examples 1 to 3 were tested, the hemostatic performance was tested by a hemolysis-coagulation method, the bacteriostatic effect was tested by a plate counting method, and the test results are shown in the following table.
| Rate of hemostasis | Rate of inhibition of bacteria | |
| Example 1 | 99.5％ | 99.9％ |
| Example 2 | 94.1％ | 98.1％ |
| Example 3 | 97.7％ | 99.9％ |
| Example 4 | 93.4％ | 94.2％ |
| Example 5 | 92.5％ | 91.8％ |
| Comparative example 1 | 57.3％ | 90.3％ |
| Comparative example 2 | 79.4％ | 81.6％ |
| Comparative example 3 | 82.7％ | 70.2％ |
As can be seen from the table above, the hemostatic performance and the bacteriostatic effect of the porous materials prepared in the examples 1 to 5 are superior to those of the comparative examples 1 to 3. The preparation method has the advantages that the graphene and the chitosan are mixed, the hemostatic performance and the antibacterial effect of the porous material are improved, and meanwhile, the acid liquor is added after the graphene and the chitosan are crosslinked, so that the hemostatic performance and the antibacterial effect of the porous material are further improved.
While embodiments of the invention have been described above, it is not limited to the applications set forth in the description and the embodiments, which are fully applicable to various fields of endeavor for which the invention may be embodied with additional modifications as would be readily apparent to those skilled in the art, and the invention is therefore not limited to the details given herein and to the embodiments shown and described without departing from the generic concept as defined by the claims and their equivalents.
Claims (9)
1. A preparation method of a porous material based on graphene oxide and chitosan molecule assembly is characterized in that a graphene oxide aqueous solution is added into a chitosan aqueous dispersion for interface self-assembly, a cross-linking agent is added for reaction, an acid solution is added for treatment, and freeze drying is carried out to obtain the cross-linked graphene oxide-chitosan porous material.
2. The preparation method of the porous material based on the assembly of the graphene oxide and the chitosan molecule as claimed in claim 1, wherein the mass ratio of the graphene oxide in the graphene oxide aqueous solution to the chitosan in the chitosan aqueous dispersion is 0.03-0.1: 1;
the concentration of the graphene oxide in the graphene oxide aqueous solution is 2-10 mg/mL.
3. The preparation method of the porous material based on graphene oxide and chitosan molecule assembly of claim 1, wherein the ratio of chitosan to the cross-linking agent in the chitosan aqueous dispersion is 30-200 g: 1 ml.
4. The preparation method of the porous material based on the assembly of the graphene oxide and the chitosan molecule according to claim 1, wherein after the cross-linking agent is added, the reaction is stirred at a speed of 100-300 rppm for 10-50 min and at a temperature of 15-35 ℃;
the cross-linking agent is one or more of glutaraldehyde, formaldehyde, glyoxal and 2, 4-pentanedione.
5. The preparation method of the porous material based on the assembly of the graphene oxide and the chitosan molecule as claimed in claim 1, wherein after the acid solution is added, the stirring speed of the treatment is 500-1200 rppm, the time is 5-30 h, and the temperature is 25-45 ℃;
the volume ratio of the acid solution to the chitosan aqueous dispersion is 0.01-0.025: 1;
the acid solution is one of glacial acetic acid, concentrated hydrochloric acid, concentrated nitric acid and oxalic acid.
6. The preparation method of the porous material based on the assembly of graphene oxide and chitosan molecules as claimed in claim 1, wherein the deacetylation degree of chitosan in the chitosan aqueous dispersion is not less than 85%.
7. A porous material based on graphene oxide and chitosan molecule assembly is characterized by being prepared by the preparation method of any one of claims 1-6.
8. A hemostatic material prepared from the porous material based on graphene oxide assembled with chitosan molecules of claim 7.
9. Use of the porous material based on the assembly of graphene oxide with chitosan molecules according to claim 7 for the preparation of hemostatic materials.
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| CN113730645B (en) * | 2021-09-14 | 2022-08-12 | 山东大学 | Sponge for rapid hemostasis and wound repair and preparation method thereof |
| CN114832143B (en) * | 2022-06-10 | 2023-12-22 | 武夷学院 | Preparation method of chitosan grafted urushiol/graphene oxide composite material |
| CN115926245B (en) * | 2023-01-05 | 2023-11-07 | 中国人民解放军军事科学院军事医学研究院 | Chitosan crosslinked graphene oxide composite sponge with high hemostatic efficiency and preparation method and application thereof |
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