CN110859990A - Chitosan quaternary ammonium salt antibacterial gel and preparation method thereof - Google Patents
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- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
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Abstract
The invention belongs to the technical field of medical medicines, and discloses a chitosan quaternary ammonium salt antibacterial gel and a preparation method thereof, wherein the chitosan quaternary ammonium salt antibacterial gel comprises the following raw materials in parts by weight: 90-99.9 parts of chitosan quaternary ammonium salt, 0.01-10 parts of organic acid and 1-5 parts of cross-linking agent; the preparation method comprises the following steps: (1) dissolving chitosan quaternary ammonium salt in deionized water according to the weight part, adding organic acid after stirring and dissolving, and continuously stirring and mixing; (2) weighing a cross-linking agent, dissolving the cross-linking agent in deionized water, slowly dropwise adding the cross-linking agent into the mixed solution obtained in the step (1), uniformly stirring and mixing the cross-linking agent and the mixed solution by magnetic force, and continuously reacting in a constant-temperature incubator to obtain gel; (3) and taking out the gel, washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel. The novel chitosan quaternary ammonium salt gel provided by the invention has good swelling performance and pH responsiveness, has strong antibacterial performance on gram-negative bacteria and gram-positive bacteria, is simple in preparation process and low in cost, and is expected to become a novel wound gel dressing.
Description
Technical Field
The invention belongs to the technical field of medical medicines, and relates to a chitosan quaternary ammonium salt antibacterial gel and a preparation method thereof.
Background
The gel dressing is a novel wound dressing developed in recent years, compared with traditional gauze, the gel has better biocompatibility, is favorable for migration and repair of epithelial tissue cells of wounds in a moist environment to promote wound healing, can block external bacterial infection to a certain degree, effectively prevents body fluid loss, can transmit enough oxygen to wounds, accelerates wound healing, and therefore, the gel is widely researched as the novel dressing. However, most gels provide a good healing environment, but are not effective enough in inhibiting bacteria. At present, most researches on improving the antibacterial performance of the gel are carried out by adding substances with stronger antibacterial activity, such as silver ions, antibiotics, iodine and the like, into the gel material, but the substances have the disadvantages.
The chitosan quaternary ammonium salt is a derivative in which an amino group or a hydroxyl group on chitosan undergoes a quaternization reaction. The quaternary ammonium salt group has relatively large steric hindrance and strong hydrophilic capability, and when the quaternary ammonium salt group is introduced into chitosan, on one hand, the hydrogen bond effect existing among chitosan molecules is destroyed, on the other hand, the hydration effect of the quaternary ammonium salt and water is increased, so that the chitosan has excellent water solubility. Meanwhile, the chitosan quaternary ammonium salt has good antibacterial property, film forming property, moisture absorption and retention property and other properties, and the antibacterial property of the chitosan quaternary ammonium salt is obviously superior to that of chitosan and other chitosan derivatives.
At present, after the gel becomes a research hotspot as a wound dressing, because the chitosan quaternary ammonium salt has better biocompatibility and antibacterial property, and the application of the chitosan quaternary ammonium salt gel in the aspect of antibacterial dressing is more and more concerned by researchers, the research and development of the chitosan quaternary ammonium salt antibacterial gel for the aspect of antibacterial dressing has important significance.
Disclosure of Invention
The invention aims to overcome the defects and provide the chitosan quaternary ammonium salt antibacterial gel which has better swelling performance and pH responsiveness, has stronger antibacterial performance on gram-negative bacteria and gram-positive bacteria, has simple preparation process and low cost and is expected to become a novel wound gel dressing.
In order to solve the technical problems, the technical scheme of the invention is as follows:
a chitosan quaternary ammonium salt antibacterial gel comprises the following raw materials in parts by weight: 90-99.9 parts of chitosan quaternary ammonium salt, 0.01-10 parts of organic acid and 1-5 parts of cross-linking agent.
Preferably, the degree of substitution of the chitosan quaternary ammonium salt is 40.3-80.3.
Preferably, the raw material also comprises N-hydroxysuccinimide, the dosage of the N-hydroxysuccinimide is 1/3 of the dosage of the cross-linking agent, and the N-hydroxysuccinimide is added in the invention, so that the stability of the whole reaction system can be improved.
Preferably, the organic acid is any one of malic acid, tartaric acid, oxalic acid, citric acid and succinic acid; malic acid is preferred, and is widely used in industries such as industry, food industry, cosmetic industry and the like as an organic acid widely existing in nature.
Preferably, the cross-linking agent is any one of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, glutaraldehyde, paraformaldehyde and dialdehyde starch; preferably 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, has the characteristics of no toxicity and good biocompatibility, and the EDC crosslinked gel shows more excellent cell compatibility.
The invention also aims to provide a preparation method of the chitosan quaternary ammonium salt antibacterial gel, which comprises the following steps:
(1) dissolving chitosan quaternary ammonium salt in deionized water according to the weight part, adding organic acid after stirring and dissolving, continuously stirring and mixing for 20-40min, and uniformly mixing;
(2) weighing a cross-linking agent according to the weight parts, dissolving the cross-linking agent in deionized water, slowly dropwise adding the cross-linking agent into the mixed solution obtained in the step (1), uniformly stirring and mixing the cross-linking agent by magnetic force, and placing the mixture in a constant temperature incubator at 25 ℃ for continuously reacting for 2 to 3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
The chitosan quaternary ammonium salt in the invention can be replaced by chitosan water-soluble derivatives such as chitosan, carboxymethyl chitosan, succinyl chitosan and the like.
Compared with the prior art, the invention has the beneficial effects that:
the novel chitosan quaternary ammonium salt gel provided by the invention has better swelling performance and pH responsiveness, and simultaneously has stronger antibacterial performance to gram-negative bacteria and gram-positive bacteria, and the preparation process is simple, the cost is low, and the novel chitosan quaternary ammonium salt gel is expected to become a novel wound gel dressing.
Drawings
FIG. 1 is a reaction schematic diagram of chitosan quaternary ammonium salt gel;
FIG. 2 shows the swelling performance of chitosan quaternary ammonium salt gel in PBS buffer solution;
FIG. 3 shows the anti-E.coli performance of chitosan quaternary ammonium salt gel;
FIG. 4 shows the anti-Staphylococcus aureus performance of chitosan quaternary ammonium salt gel.
Detailed Description
The principles and features of this patent are described below in conjunction with the following drawings, which are provided by way of example to illustrate the patent and not to limit the scope of the patent.
Example 1
A preparation method of chitosan quaternary ammonium salt antibacterial gel comprises the following steps:
(1) dissolving 90 parts by weight of chitosan quaternary ammonium salt in deionized water, stirring and dissolving, adding 10 parts by weight of tartaric acid, continuously stirring and mixing for 20min, and uniformly mixing;
(2) weighing 1 part by weight of glutaraldehyde, dissolving the glutaraldehyde in deionized water, slowly dropwise adding the glutaraldehyde into the mixed solution obtained in the step (1), uniformly stirring and mixing the glutaraldehyde and the deionized water by magnetic force, placing the mixture in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
Example 2
A preparation method of chitosan quaternary ammonium salt antibacterial gel comprises the following steps:
(1) dissolving 99.9 parts by weight of chitosan quaternary ammonium salt in deionized water, stirring and dissolving, adding 0.01 part by weight of oxalic acid, continuously stirring and mixing for 40min, and uniformly mixing;
(2) weighing 5 parts by weight of paraformaldehyde, dissolving in deionized water, slowly dropwise adding into the mixed solution obtained in the step (1), uniformly stirring and mixing by magnetic force, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
Example 3
A preparation method of chitosan quaternary ammonium salt antibacterial gel comprises the following steps:
(1) dissolving 95 parts by weight of chitosan quaternary ammonium salt in deionized water, stirring and dissolving, adding 5 parts by weight of malic acid, continuously stirring and mixing for 30min, and uniformly mixing;
(2) weighing 3 parts by weight of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 1 part by weight of N-hydroxysuccinimide, dissolving in deionized water, slowly dropwise adding into the mixed solution obtained in the step (1), uniformly stirring and mixing by magnetic force, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
Example 4
A preparation method of chitosan quaternary ammonium salt antibacterial gel comprises the following steps:
(1) dissolving 92 parts by weight of chitosan quaternary ammonium salt in deionized water, stirring and dissolving, adding 8 parts by weight of citric acid, continuously stirring and mixing for 20-40min, and uniformly mixing;
(2) weighing 2 parts by weight of dialdehyde starch and 2/3 parts by weight of N-hydroxysuccinimide, dissolving in deionized water, slowly dropwise adding into the mixed solution in the step (1), magnetically stirring and uniformly mixing, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
Example 5
A preparation method of chitosan quaternary ammonium salt antibacterial gel comprises the following steps:
(1) dissolving 96 parts by weight of chitosan quaternary ammonium salt in deionized water, stirring and dissolving, adding 4 parts by weight of succinic acid, continuously stirring and mixing for 25min, and uniformly mixing;
(2) weighing 4 parts by weight of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, dissolving in deionized water, slowly dropwise adding into the mixed solution obtained in the step (1), uniformly stirring and mixing by magnetic force, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
Example 6
A preparation method of chitosan antibacterial gel comprises the following steps:
(1) dissolving 95 parts by weight of chitosan in deionized water, stirring to dissolve, adding 5 parts by weight of malic acid, continuously stirring and mixing for 30min, and uniformly mixing;
(2) weighing 3 parts by weight of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 1 part by weight of N-hydroxysuccinimide, dissolving in deionized water, slowly dropwise adding into the mixed solution obtained in the step (1), uniformly stirring and mixing by magnetic force, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan antibacterial gel.
Example 7
A preparation method of chitosan antibacterial gel comprises the following steps:
(1) dissolving 95 parts by weight of carboxymethyl chitosan in deionized water, stirring to dissolve, adding 5 parts by weight of malic acid, continuously stirring and mixing for 30min, and uniformly mixing;
(2) weighing 3 parts by weight of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 1 part by weight of N-hydroxysuccinimide, dissolving in deionized water, slowly dropwise adding into the mixed solution obtained in the step (1), uniformly stirring and mixing by magnetic force, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan antibacterial gel.
Example 8
A preparation method of chitosan antibacterial gel comprises the following steps:
(1) dissolving 95 parts by weight of succinyl chitosan in deionized water, stirring to dissolve, adding 5 parts by weight of malic acid, continuously stirring and mixing for 30min, and uniformly mixing;
(2) weighing 3 parts by weight of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 1 part by weight of N-hydroxysuccinimide, dissolving in deionized water, slowly dropwise adding into the mixed solution obtained in the step (1), uniformly stirring and mixing by magnetic force, placing in a constant-temperature incubator at 25 ℃ for continuously reacting for 2-3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan antibacterial gel.
Test examples
1. An antibacterial gel was prepared according to the method of example 3, wherein the weight concentrations of malic acid added were set to 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, respectively, and the swelling properties of the gel were investigated according to a weighing method. A certain mass of the gel was weighed and soaked in buffer solutions with pH 1.0 and pH 7.4, respectively. And taking out at intervals, slightly sucking residual moisture on the surface by using filter paper, and weighing by using an electronic analytical balance. The swelling degree corresponding to different moments is defined as:
wherein m iswetIs time tMass of gel (g); m isdryIs the initial mass (g) of the gel before swelling. The test results are shown in FIG. 2.
As can be seen from fig. 2, the swelling ratio is also evident as the malic acid concentration increases in the pH 7.4 environment. The reason is that as the concentration of malic acid is increased, the carboxylic acid groups participating in the crosslinking reaction are increased, but the probability that two carboxylic acid groups of malic acid are simultaneously connected with the chitosan quaternary ammonium salt polymer is reduced, and the number of crosslinking points forming the effective network structure of the gel is relatively reduced, so that the network structure in the gel is looser and looser, the pore diameter is increased, the space structure is enlarged, the absorption of water is facilitated, and the swelling rate is increased finally.
2. Antibacterial gel was prepared according to the method of example 3, wherein the substitution degrees of the chitosan quaternary ammonium salt were set to 40.3, 51.2, 63.2, 71.1, and 80.3, respectively, and antibacterial performance test was performed on the prepared antibacterial gel.
The specific detection method comprises the following steps: in an aseptic operation table, taking 0.1g of dried gel sample, putting the gel sample in a beef extract peptone liquid culture medium for swelling until the swelling is balanced, transferring the gel sample into 50ml of fresh beef extract peptone liquid culture medium, and selecting a ring of fresh bacterial liquid for later use by using an inoculating ring to put the fresh bacterial liquid into the culture medium so that the concentration of the bacterial liquid is about 106-107CFU/ml, as experimental group. Taking 50ml of bacterial liquid culture medium without gel as a control group, taking 50ml of liquid culture medium as a control group, and taking pure liquid culture medium as a blank group. Placing in a constant temperature oscillator at a rotation speed of 150r/min and a temperature of 37 deg.C, taking out at intervals, after oscillation, respectively scanning the selected Staphylococcus aureus and Escherichia coli liquid on an ultraviolet spectrophotometer at full wavelength to select maximum absorption peak, and determining that the two kinds of liquid have maximum absorption at 600 nm. Therefore, the absorbance of the experimental group and the control group was measured with the blank group as a reference, with the wavelength of the UV spectrophotometer set at 600 nm. The test results are shown in FIGS. 3-4.
As can be seen from fig. 3 and 4, the bacteriostatic ratio of the gel increased with the increase in the degree of substitution of the chitosan quaternary ammonium salt. As the substitution degree of the chitosan quaternary ammonium salt is increased, the space of a gel network is enlarged, the swelling performance of the gel is enhanced, so that escherichia coli and staphylococcus aureus are more easily contacted with the surface of the three-dimensional network structure in the gel, the cell membrane of bacteria is damaged, the bacteria die, and finally the bacteriostasis capacity of the gel is improved.
The foregoing is considered as illustrative of the preferred embodiments of the invention, but is made merely for the purpose of providing an understanding of the principles of the embodiments; meanwhile, for a person skilled in the art, according to the present embodiment, there may be a change in the specific implementation and application scope, and in summary, the present disclosure should not be construed as a limitation to the present invention. It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein, and any reference signs in the claims are not intended to be construed as limiting the claim concerned.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the present invention, and any modifications, equivalents, improvements and the like that are within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (7)
1. A chitosan quaternary ammonium salt antibacterial gel is characterized in that: the feed comprises the following raw materials in parts by weight: 90-99.9 parts of chitosan quaternary ammonium salt, 0.01-10 parts of organic acid and 1-5 parts of cross-linking agent.
2. The chitosan quaternary ammonium salt antibacterial gel according to claim 1, characterized in that: the degree of substitution of the chitosan quaternary ammonium salt is 40.3-80.3.
3. The chitosan quaternary ammonium salt antibacterial gel according to claim 1, characterized in that: the starting material also comprises N-hydroxysuccinimide.
4. The chitosan quaternary ammonium salt antibacterial gel according to claim 2, characterized in that: the amount of the N-hydroxysuccinimide is 1/3 that of the cross-linking agent.
5. The chitosan quaternary ammonium salt antibacterial gel according to claim 1, characterized in that: the organic acid is any one of malic acid, tartaric acid, oxalic acid, citric acid and succinic acid.
6. The chitosan quaternary ammonium salt antibacterial gel according to claim 1, characterized in that: the cross-linking agent is any one of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, glutaraldehyde, paraformaldehyde and dialdehyde starch.
7. A method for preparing the chitosan quaternary ammonium salt antibacterial gel of claim 1, which is characterized in that: the method comprises the following steps:
(1) dissolving chitosan quaternary ammonium salt in deionized water according to the weight part, adding organic acid after stirring and dissolving, continuously stirring and mixing for 20-40min, and uniformly mixing;
(2) weighing a cross-linking agent according to the weight parts, dissolving the cross-linking agent in deionized water, slowly dropwise adding the cross-linking agent into the mixed solution obtained in the step (1), uniformly stirring and mixing the cross-linking agent by magnetic force, and placing the mixture in a constant temperature incubator at 25 ℃ for continuously reacting for 2 to 3 days to obtain gel;
(3) and (3) after the reaction is finished, taking out the gel obtained in the step (2), washing with ethanol, and freeze-drying to obtain the chitosan quaternary ammonium salt antibacterial gel.
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| CN112056511A (en) * | 2020-09-03 | 2020-12-11 | 余姚谷满仓食品有限公司 | Processing technology of quick-frozen green soy beans |
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| DE102013225182A1 (en) * | 2013-12-06 | 2014-04-17 | Henkel Ag & Co. Kgaa | Cosmetic composition, useful for caring keratin fibers, comprises chitosan, quaternary ammonium compound(s), acid(s) comprising acetic acid, lactic acid, tartaric acid, citric acid, malic acid, ascorbic acid and gluconic acid, and water |
| CN105079861A (en) * | 2015-09-09 | 2015-11-25 | 青岛高新区尚达医药研究所 | Preparation process of modified chitosan composite gel moisture retention adhesive bandage |
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| CN112056511A (en) * | 2020-09-03 | 2020-12-11 | 余姚谷满仓食品有限公司 | Processing technology of quick-frozen green soy beans |
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Application publication date: 20200306 |