CN111732737A - Degradable self-healing chitosan composite aldehyde guar gum gel and preparation method and application thereof - Google Patents
Degradable self-healing chitosan composite aldehyde guar gum gel and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of hydrogel materials, and particularly relates to degradable self-healing chitosan composite hydroformylation guar gum gel and a preparation method and application thereof. The method comprises the following steps: 1) obtaining a solution of Chitosan (CHI); 2) preparing a solution of an aldehyde guar (AGG); 3) and reacting the solution of the aldehyde guar gum with the solution of chitosan to prepare the degradable self-healing chitosan composite aldehyde guar gum gel. The invention utilizes aldehyde group on AGG chain and amino group on CHI chain to carry out Schiff base reaction to form imine bond, and the imine bond is taken as a crosslinking point to obtain CHI/AGG hydrogel. Due to a dynamic crosslinking mechanism, the hydrogel can realize self-healing within 5min and can be degraded near a neutral environment.
Description
Technical Field
The invention belongs to the technical field of hydrogel materials, and particularly relates to degradable self-healing chitosan composite hydroformylation guar gum gel and a preparation method and application thereof.
Background
A hydrogel is a high molecular weight polymer with a three-dimensional network structure that absorbs large amounts of water or biological fluids, and can be chemically stable or can degrade and eventually break down or dissolve. The hydrogel has wide application and prospect in the biomedical field such as biosensors, tissue engineering scaffolds, drug carriers, artificial implants, cell or ion growth templates and the like.
Self-healing hydrogels are hydrogels that are capable of causing a material to essentially self-heal a lesion, restoring its normal properties. Self-healing typically occurs in a prepared material that does not interfere with the external stimuli that promote the self-healing to occur. The development of hydrogel with good biocompatibility, biodegradability and certain self-healing performance is an important subject in the current biomedical field.
Chinese patent CN110628090A discloses a cationic guar gum/chitosan composite hydrogel and a preparation method thereof, the method adopts chitosan and cationic guar gum as reaction raw materials, firstly, chitosan, cationic guar gum and sodium periodate are simultaneously added into acetic acid solution to obtain mixed solution A, and then the solution A is stood at room temperature to obtain the cationic guar gum/chitosan composite hydrogel. The hydrogel forms cyclic acetal through condensation reaction of carbonyl introduced into chitosan and hydroxyl on a cationic guar gum molecule, while Schiff base is formed by the carbonyl introduced into the cationic guar gum and amino on the chitosan molecule, so that intermolecular crosslinking is realized. The raw materials used in the preparation method are modified too much, and the method does not discuss the self-repairability and degradability of the hydrogel. According to the invention, sodium periodate oxidized guar gum is adopted, the used raw materials are not subjected to secondary modification, and the obtained hydrogel has good self-repairability and degradability and has more application potentials in the field of biomedicine.
Disclosure of Invention
The invention aims to provide a degradable self-healing chitosan composite aldehydized guar gum gel and a preparation method and application thereof. The hydrogel material with good self-healing capability and certain degradability is finally prepared by simple and easily-obtained raw materials and mild but not complicated reaction procedures. The hydrogel material can autonomously and circularly respond to structural damage caused by external stimulation, can realize efficient degradation under certain conditions, and has wide application prospects in the biomedical field.
The technical scheme provided by the invention is as follows:
a preparation method of degradable self-healing chitosan composite hydroformylation guar gum gel comprises the following steps:
1) obtaining a solution of Chitosan (CHI);
2) preparing a solution of an aldehyde guar (AGG);
3) and reacting the solution of the aldehyde guar gum with the solution of chitosan to prepare the degradable self-healing chitosan composite aldehyde guar gum gel.
In the technical scheme, aldehyde groups on the AGG chain and amino groups on the CHI chain are subjected to Schiff base reaction to form imine bonds, and the imine bonds are taken as crosslinking points to obtain the CHI/AGG hydrogel. Due to a dynamic crosslinking mechanism, the hydrogel can realize self-healing within 5min and can be degraded in a neutral environment.
Specifically, in the step 2), sodium periodate is adopted to oxidize Guar Gum (GG) to obtain aldehyde guar gum.
In the technical scheme, the AGG with aldehyde group is obtained by oxidation reaction, and the AGG chain has aldehyde group.
Specifically, in the step 3), the aldehyde-group guar gum and chitosan are subjected to Schiff base reaction to prepare the degraded self-healing chitosan composite aldehyde-group guar gum gel.
Specifically, the method comprises the following steps:
a) dissolving chitosan in an acid solution, dialyzing by a dialysis bag, performing rotary evaporation, and freeze-drying to obtain solid chitosan, and dissolving the solid chitosan in water to obtain a chitosan solution;
b) dissolving guar gum in deionized water, and magnetically stirring until the guar gum is completely dissolved to obtain a guar gum solution;
c) dissolving sodium periodate in deionized water, dropwise adding the sodium periodate into a guar gum solution, uniformly stirring, stirring the mixed solution in a dark place, and carrying out oxidation reaction to obtain a reaction solution;
d) adding ethylene glycol into the reaction solution obtained in the step c) and stirring to terminate the reaction to obtain an primary aldehyde guar gum product, and pouring the primary aldehyde guar gum product into a dialysis bag for dialysis;
e) performing rotary evaporation on the primary aldehyde guar gum obtained by dialysis to obtain solid aldehyde guar gum, and dissolving the solid aldehyde guar gum in water to obtain aldehyde guar gum solution for later use;
f) and mixing the chitosan solution with the aldehyde guar gum solution to form hydrogel, thereby obtaining the degradable self-healing chitosan composite aldehyde guar gum gel.
Specifically, the method comprises the following steps:
in the step a), the acidic solution is a hydrochloric acid solution with the pH value of 3-5;
in the step a), the dialysis time is 7-14 days, and the dialysate is deionized water; the rotary steaming time is 1 day; the freeze-drying time is 3-10 days; the temperature of freeze-drying is less than or equal to-50 ℃;
in the step a), the dissolving temperature is 0-30 ℃;
in the step a), the mass fraction of the obtained chitosan solution is 5-7%;
specifically, in the step b), the dissolving temperature is 0-30 ℃.
Specifically, the method comprises the following steps:
in the step c), the mass fraction of the sodium periodate is 0.4-2%;
in the step c), the mass fraction of the guar gum solution is 12-25%;
in step c), the molar ratio of the sodium periodate to the guar gum is (0.1:1) to (1: 1);
in the step c), the light-resistant stirring time is 6-24 hours.
Specifically, the method comprises the following steps:
in the step d), the molar ratio of the ethylene glycol to the guar gum is (0.1:1) - (1: 1); the stirring time is 0.5-6 h;
in step d), the dialysate used for dialysis is deionized water.
Specifically, the method comprises the following steps:
in the step e), the rotary evaporation time is 1 day, and the freeze-drying time is 5-10 days;
in the step e), the mass fraction of the obtained aldehyde guar gum solution is 10-20%;
specifically, in the step f), the mixing volume ratio of the chitosan solution to the aldehyde guar gum solution is (2:1) - (1: 5).
The invention also provides a preparation method of the degradable self-healing chitosan composite hydroformylation guar gum gel.
The invention also provides application of the degradable self-healing chitosan composite aldehyde guar gum gel as a biomedical material.
Compared with the prior art, the invention has the following unexpected beneficial effects:
1) the natural polysaccharide is completely adopted as a reaction raw material. Guar gum is obtained from the endosperm of guar and has good solubility, softness and biocompatibility. Chitosan is a natural polymer of polysaccharide with the characteristics of good biocompatibility, low cytotoxicity, biodegradability in vivo and the like. The two natural polymers are selected to ensure that the prepared hydrogel has good biocompatibility, and potential harm brought by the polymerized polymers is avoided.
2) The dynamic covalent crosslinking is adopted as a self-healing mechanism, the traditional chemical crosslinking is replaced, the chemical pollution caused by the chemical crosslinking is avoided, and more possibilities are provided for the application of the hydrogel in the biomedical field.
3) The hydrogel preparation method is simple, easy to operate, mild in reaction conditions, easy to obtain raw materials and low in cost. The obtained hydrogel can autonomously and repeatedly repair micro-scale to macro-scale damage caused by external stimulation, has degradability and has wide application prospect in the biomedical field.
Drawings
FIG. 1 is a diagram of the oxidation process (a) of GG and the preparation mechanism (b) of CHI/AGG hydrogel;
FIG. 2 is a nuclear magnetic hydrogen spectrum of GG and AGG;
FIG. 3 is an exemplary illustration of two differently colored hydrogels obtained from example 3 (a) placed together to completely release the seam (b) for a certain period of time to be able to bear their own weight (c), and stretched without breaking (d), and then cut into pieces (e) and placed in a crab-shaped mold to obtain a complete self-healing hydrogel (f);
FIG. 4 is a time-interleaved scan of the hydrogel dynamics;
figure 5 is a schematic view of hydrogel degradation.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
Step (1): dissolving CHI (5g) in 100mL hydrochloric acid solution with pH of 3, dialyzing in a dialysis bag for 7d, and freeze-drying to obtain protonated CHI soluble in deionized water;
step (2): dissolving 2g of GG in 100mL of deionized water, and magnetically stirring at room temperature until the GG is completely dissolved;
and (3): dissolving 0.44g of sodium periodate in 10mL of deionized water, dropwise adding the solution into GG solution, and uniformly stirring;
and (4): stirring the mixed solution at room temperature in the dark for 12h, and carrying out oxidation reaction to generate AGG;
and (5): 1mL of ethylene glycol was added to the solution of step (4) and stirred for 1h to terminate the reaction. Pouring the AGG into a dialysis bag for dialysis for 7d, and freeze-drying for 3d for later use after rotary evaporation;
and (6): and uniformly mixing the protonated CS solution with the mass fraction of 7% and the AGG with the mass fraction of 15% at room temperature in a volume ratio of 1:3 respectively until the CHI/AGG hydrogel is formed.
Example 2
Step (1): dissolving CHI (5g) in 100mL hydrochloric acid solution with pH 4, dialyzing in a dialysis bag for 10d, and freeze-drying to obtain protonated CHI soluble in deionized water;
step (2): dissolving 2g of GG in 100mL of deionized water, and magnetically stirring at room temperature until the GG is completely dissolved;
and (3): dissolving 1.2g of sodium periodate in 10mL of deionized water, dropwise adding the solution into GG solution, and uniformly stirring;
and (4): stirring the mixed solution at room temperature in the dark for 10h, and carrying out oxidation reaction to generate AGG;
and (5): to the solution of step (4), 1.5mL of ethylene glycol was added and stirred for 1.5h to terminate the reaction. Pouring the AGG into a dialysis bag, dialyzing for 15d, then carrying out rotary evaporation, and freeze-drying the solution obtained by rotary evaporation for 5d for later use;
and (6): and uniformly mixing the protonated CHI solution with the mass fraction of 5% and the AGG with the mass fraction of 10% at room temperature in a volume ratio of 1:1 respectively until the CHI/AGG hydrogel is formed.
Example 3
Step (1): dissolving CHI (5g) in 100mL hydrochloric acid solution with pH of 5, dialyzing in a dialysis bag for 14d, rotary-steaming, and freeze-drying the rotary-steamed solution to obtain protonated CHI soluble in deionized water;
step (2): dissolving 2g of GG in 100mL of deionized water, and magnetically stirring at room temperature until the GG is completely dissolved;
and (3): dissolving 2.3g of sodium periodate in 10mL of deionized water, dropwise adding the solution into GG solution, and uniformly stirring;
and (4): stirring the mixed solution at room temperature in the dark for 6 hours, and carrying out oxidation reaction to generate AGG;
and (5): 2mL of ethylene glycol was added to the solution of step (4) and stirred for 6h to terminate the reaction. Pouring the AGG into a dialysis bag, dialyzing for 14d, then carrying out rotary evaporation, and freeze-drying rotary evaporation liquid for 3d for later use;
and (6): the 6% by weight protonated CS solution and the 18% by weight AGG solution were mixed together homogeneously at room temperature in a volume ratio of 1:5, respectively, until the CHI/AGG hydrogel was formed.
Example 4
Step (1): dissolving CHI (5g) in 100mL hydrochloric acid solution with pH of 3, dialyzing in a dialysis bag for 7d, and freeze-drying to obtain protonated CHI soluble in deionized water;
step (2): dissolving 2g of GG in 100mL of deionized water, and magnetically stirring at room temperature until the GG is completely dissolved;
and (3): dissolving 0.44g of sodium periodate in 10mL of deionized water, dropwise adding the solution into GG solution, and uniformly stirring;
and (4): stirring the mixed solution at room temperature in the dark for 12h, and carrying out oxidation reaction to generate AGG;
and (5): 1mL of ethylene glycol was added to the solution of step (4) and stirred for 1h to terminate the reaction. Pouring the AGG into a dialysis bag, dialyzing for 1 week, and freeze-drying for 3d for later use;
and (6): the 7% by weight protonated CS solution and the 20% by weight AGG solution were mixed together at room temperature in a volume ratio of 2:1, respectively, until the CHI/AGG hydrogel was formed.
Example 5
Step (1): dissolving CHI (5g) in 100mL hydrochloric acid solution with pH of 3, dialyzing in a dialysis bag for 7d, rotary-steaming, and freeze-drying the rotary-steamed solution to obtain protonated CHI soluble in deionized water;
step (2): dissolving 2g of GG in 100mL of deionized water, and magnetically stirring at room temperature until the GG is completely dissolved;
and (3): dissolving 0.8g of sodium periodate in 10mL of deionized water, dropwise adding the solution into GG solution, and uniformly stirring;
and (4): stirring the mixed solution at room temperature in the dark for 10h, and carrying out oxidation reaction to generate AGG;
and (5): 1.5mL of ethylene glycol was added to the solution of step (4) and stirred for 2h to terminate the reaction. Pouring the AGG into a dialysis bag, dialyzing for 13d, and freeze-drying for 3d for later use;
and (6): and uniformly mixing the protonated CS solution with the mass fraction of 6% and the AGG with the mass fraction of 15% at room temperature in a volume ratio of 1:5 respectively until the CHI/AGG hydrogel is formed.
Example 6
Step (1): dissolving CHI (500g) in 10L hydrochloric acid solution with pH of 3, dialyzing in dialysis bag for 14d, rotary evaporating, and lyophilizing the rotary evaporated solution for 10d to obtain protonated CHI soluble in deionized water;
step (2): 200g of GG is dissolved in 10L of deionized water, and magnetic stirring is carried out at room temperature until the GG is completely dissolved;
and (3): dissolving 44g of sodium periodate in 1L of deionized water, dropwise adding the sodium periodate into GG solution, and uniformly stirring;
and (4): stirring the mixed solution at room temperature in the dark for 12h, and carrying out oxidation reaction to generate AGG;
and (5): 100mL of ethylene glycol was added to the solution of step (4) and stirred for 12h to terminate the reaction. Pouring the AGG into a dialysis bag, dialyzing for 14d, then performing rotary evaporation, and freeze-drying for 10d for later use;
and (6): the 7% by weight protonated CS solution and the 20% by weight AGG solution were mixed together at room temperature in a volume ratio of 1:5, respectively, until the CHI/AGG hydrogel was formed.
As shown in fig. 1, the formed product degradable self-healing chitosan composite aldehydized guar gum gel has characteristic carbon-nitrogen double bonds.
As shown in fig. 2, the nmr spectrum of AGG showed a new peak at 8.2, indicating the presence of aldehyde protons. The new peak at 5.3 is due to the formation of hemiacetal by oxidizing part of aldehyde groups and hydroxyl groups on GG, and all the above results show that the oxidation process successfully obtains AGG, and the characteristic carbon-nitrogen double bond is formed in the product.
As can be seen from FIG. 3, when 2 pieces of CHI/AGG5 hydrogels of different colors were put together to make the interfaces fully contact, and left to stand for 5min, the 2 pieces of hydrogels completely healed to form a whole. One end of the hydrogel is clamped by forceps, and the hydrogel can completely support the self weight and cannot break or fall off. The hydrogel is clamped by forceps and stretched towards two ends, and the hydrogel is not broken and can be stretched to 1.5 times of the original length. Cutting the healed hydrogel into irregular fragments, filling the fragments into a crab-shaped mold, wrapping the mold in a humid environment by using a preservative film, standing for 30min, taking out the hydrogel, and completely healing the hydrogel into a whole. The phenomenon shows that the chitosan composite aldehydized guar gum gel has excellent self-healing capability.
As can be seen from FIG. 4, when the hydrogel was loaded with a constant strain of 5% for 3min, the storage modulus (G ') of the hydrogel was higher than the loss modulus (G'). At this time, when the hydrogel was subjected to a high strain of 600%, the hydrogel G "was higher than G', exhibiting dynamic fluid characteristics, indicating that the modified hydrogel network structure was broken. After 5min of healing time with the hydrogel, the above procedure was repeated, continuing to apply 5% strain to the hydrogel and the hydrogel dynamic rheological properties were restored, G' being greater than G ", indicating that the hydrogel internal network structure was restored and the hydrogel healed. The process is repeated for 3 times, and the hydrogel still presents good self-repairing performance.
As can be seen from FIG. 5, the chitosan composite aldehyde guar gum gel can be degraded in a neutral environment, namely PBS solution with pH of 6.8 to 7.4, within 1 week, and the highest degradation rate can reach 65 percent
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 invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A preparation method of degradable self-healing chitosan composite hydroformylation guar gum gel is characterized by comprising the following steps:
1) obtaining a solution of chitosan;
2) preparing a solution of aldehyde guar gum;
3) and reacting the solution of the aldehyde guar gum with the solution of chitosan to prepare the degradable self-healing chitosan composite aldehyde guar gum gel.
2. The method for preparing the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 1, wherein in the step 2), sodium periodate is used to oxidize guar gum to obtain aldehydized guar gum.
3. The method for preparing the degradable self-healing chitosan composite aldehyde guar gum gel according to claim 1, wherein in the step 3), the aldehyde guar gum and chitosan are subjected to Schiff base reaction to prepare the degradable self-healing chitosan composite aldehyde guar gum gel.
4. The preparation method of the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 1, characterized by comprising the following steps:
a) dissolving chitosan in an acid solution, dialyzing by a dialysis bag, performing rotary evaporation, and freeze-drying to obtain solid chitosan, and dissolving the solid chitosan in water to obtain a chitosan solution for later use;
b) dissolving guar gum in deionized water, and magnetically stirring until the guar gum is completely dissolved to obtain a guar gum solution;
c) dissolving sodium periodate in deionized water, adding the solution into the guar gum solution, uniformly stirring, stirring the mixed solution in the dark, and carrying out oxidation reaction to obtain a reaction solution;
d) adding ethylene glycol into the reaction solution obtained in the step c) and stirring to terminate the reaction to obtain an primary aldehyde guar gum product, and pouring the primary aldehyde guar gum product into a dialysis bag for dialysis;
e) performing rotary evaporation on the dialyzed primary aldehyde guar gum, then performing freeze-drying on the primary aldehyde guar gum to obtain solid aldehyde guar gum, and dissolving the solid aldehyde guar gum in water to obtain an aldehyde guar gum solution for later use;
f) mixing the chitosan solution and the aldehyde guar gum solution to form hydrogel, and obtaining the degradable self-healing chitosan composite aldehyde guar gum gel.
5. The preparation method of the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 4, wherein the preparation method comprises the following steps:
in the step a), the acidic solution is a hydrochloric acid solution with the pH value of 3-5;
in the step a), the dialysis time is 7-14 days, and the dialysate is deionized water; the rotary steaming time is 1 day; the freeze-drying time is 3-10 days; the temperature of freeze-drying is less than or equal to-50 ℃; in the step a), the dissolving temperature is 0-30 ℃;
in the step a), the mass fraction of the obtained chitosan solution is 5-7%;
in the step b), the dissolving temperature is 0-30 ℃.
6. The preparation method of the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 4, wherein the chitosan composite aldehydized guar gum gel is prepared by mixing the guar gum with water,
in the step c), the mass fraction of the sodium periodate is 0.4-2%;
in the step c), the mass fraction of the guar gum solution is 12-25%;
in the step c), the molar ratio of the sodium periodate to the guar gum is (0.1:1) - (1: 1);
in the step c), the light-resistant stirring time is 6-24 hours.
7. The preparation method of the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 4, wherein the preparation method comprises the following steps:
in the step d), the molar use ratio of the ethylene glycol to the guar gum is (0.1:1) - (1: 1); the stirring time is 0.5-6 h;
in step d), the dialysate used for dialysis is deionized water.
8. The preparation method of the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 4, wherein the preparation method comprises the following steps:
in the step e), the rotary evaporation time is 1 day, and the freeze-drying time is 5-10 days;
in the step e), the mass fraction of the obtained aldehyde guar gum solution is 10-20%;
in the step f), the mixing volume ratio of the chitosan solution to the aldehyde guar gum solution is (2:1) - (1: 5).
9. The degradable self-healing chitosan composite aldehydized guar gum gel is prepared by the preparation method of the degradable self-healing chitosan composite aldehydized guar gum gel according to any one of claims 1 to 8.
10. The application of the degradable self-healing chitosan composite aldehydized guar gum gel according to claim 9, wherein the degradable self-healing chitosan composite aldehydized guar gum gel is characterized in that: as biomedical materials.
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| CN114702698A (en) * | 2022-05-18 | 2022-07-05 | 天津科技大学 | Double-crosslinking self-healing hydrogel and preparation method thereof |
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| CN113354854A (en) * | 2021-05-27 | 2021-09-07 | 武汉工程大学 | Flexible membrane with humidity response and preparation method and application thereof based on self-assembly |
| CN113402764A (en) * | 2021-06-22 | 2021-09-17 | 上海交通大学 | Recyclable multifunctional dynamic covalent polymer aerogel material and preparation method and application thereof |
| CN114712550A (en) * | 2022-04-20 | 2022-07-08 | 华中科技大学 | Hydrogel adhesive capable of being injected for rapid hemostasis and preparation method and application thereof |
| CN114748677A (en) * | 2022-04-20 | 2022-07-15 | 华中科技大学 | Anti-adhesion hydrogel adhesive, and preparation method and application thereof |
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| CN114702698A (en) * | 2022-05-18 | 2022-07-05 | 天津科技大学 | Double-crosslinking self-healing hydrogel and preparation method thereof |
| CN115990285A (en) * | 2023-03-22 | 2023-04-21 | 中国人民解放军军事科学院军事医学研究院 | Multifunctional composite hydrogel and preparation method and application thereof |
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