CN101664563B - Preparation method of anti-bacterial hydrogel dressing - Google Patents
Preparation method of anti-bacterial hydrogel dressing Download PDFInfo
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- CN101664563B CN101664563B CN200910152700A CN200910152700A CN101664563B CN 101664563 B CN101664563 B CN 101664563B CN 200910152700 A CN200910152700 A CN 200910152700A CN 200910152700 A CN200910152700 A CN 200910152700A CN 101664563 B CN101664563 B CN 101664563B
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- hydrogel dressing
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Abstract
The invention discloses a preparation method of anti-bacterial hydrogel dressing. The method comprises the following steps: 1) dissolving dihydroxy-terminated polyethylene glycol in tetrahydrofuran, adding acryloyl chloride to react at room temperature under the protection of nitrogen, treating the obtained reaction product through filtrating, evaporating, washing and concentrating to obtain polyethyleneglycol diacrylate crosslinking agent; 2) using ZnO nanoparticles containing Ag<+> to prepare 15-30wt% of nanometer water solution, then dissolving natural high molecular material in the nanometer water solution to obtain natural high molecular water solution containing nano-Ag; 3) mixing acrylamide, polyethyleneglycol and natural high molecular water solution containing nano-Ag, placing the mixture at room temperature under the irradiation of <60>Co source for crosslinking and obtaining the anti-bacterial hydrogel dressing, the molar ratio of Ag to Zn is 1:4. The anti-bacterial hydrogel dressing prepared by the method is a kind of porous reticular dressing with antibacterial property and hydrating capacity.
Description
Technical field
The invention belongs to medical trauma repair materials manufacturing technology field, particularly relate to a kind of irradiation technique that utilizes and form synthetic high polymer and natural polymer are crosslinked, have the method for preparing of the holey dressing of anti-microbial property and hydrating capacity.
Background technology
Skin is the maximum organ of human body, is the human body and the extraneous natural cover for defense; Yet large tracts of land is exposed to extraneous characteristics makes skin be easy to receive external injuries such as burn, mechanical injury.China's large population base; Nearly 1,000,000 serious burn and scald patients are arranged every year approximately; Moreover; The large area skin ulcer that the complication of a lot of chronic diseases such as diabetes, phlebitis, decubital ulcer etc. cause is also more and more common in China, and these patients are because the autosynthesis scarce capacity all needs the skin transplantation treatment.
Nearly all temporary dressing both at home and abroad at present all is difficult to realize the control of hydrops and water evaporates, can not effectively absorb the metabolite and removing slough of wound site, does not have anti-infection ability and hemostatic function.Because the large area skin wound restore cycle is long; In the dosage that needs with antibiotics big, the cycle is longer, and long-time heavy dose of antibiotics that uses generally can produce serious antibiotic tolerance; This is a common problem among the surgical wound treatment, is a very serious clinical problem equally.
Along with the development of materialogy, synthesized polymer materials such as polyacrylamide, polyurethane, polyvinyl alcohol are widely used in the novel skin dressing; Yet, these materials except adhesion is good, isolate bacteria and maintenance wound surface moistening, do not have other function.
Summary of the invention
The technical problem that the present invention will solve provides a kind of method for preparing of anti-bacterial hydrogel dressing, and adopting the anti-bacterial hydrogel dressing of this method preparation is a kind of holey dressing with anti-microbial property and hydrating capacity.
In order to solve the problems of the technologies described above, the present invention provides a kind of method for preparing of anti-bacterial hydrogel dressing, may further comprise the steps:
1), hydroxyl carbowax is dissolved in the oxolane, under ice bath, drip acryloyl chloride, the mol ratio of said acryloyl chloride and hydroxyl carbowax is 3: 1～20: 1; Drip off the recession deicing and bathe, under nitrogen protection, in room temperature, reacted 8～10 hours;
With the product elimination solid of gained, get clear liquid; With the clear liquid evaporate to dryness, get crude product again; Crude product gets Polyethylene Glycol double methacrylate cross-linking agent after washing and concentrating;
2), will contain Ag
+The ZnO nano-particle to be mixed with mass concentration be 15～30% nano aqueous solution, the mol ratio of said Ag: Zn=1: 4; Then natural macromolecular material is dissolved in the said nano aqueous solution, must contain the natural polymer aqueous solution of nanometer Ag; Said natural macromolecular material is 10: 1～50: 1 with the mass ratio that contains the ZnO nano-particle of Ag+;
3), with acrylamide, Polyethylene Glycol double methacrylate cross-linking agent with contain the water-soluble liquid-phase mixing of natural polymer of nanometer Ag; The mass ratio of acrylamide and natural macromolecular material is 1: 1～20: 1, and the mass ratio of acrylamide and hydroxyl carbowax is 1.8～2.2: 1; Place under the room temperature then
60Co source cross-linking radiation, irradiation dose are 20～100KGy; Get anti-bacterial hydrogel dressing.
Improvement as the method for preparing of anti-bacterial hydrogel dressing of the present invention: in the step 1), earlier with crude product with saturated nacl aqueous solution washing three times, be dissolved in then in the dichloromethane, the reconcentration organic facies makes liquor capacity be decreased to 40% of original volume; The deposition that adds diethyl ether at last, the gained precipitate is Polyethylene Glycol double methacrylate cross-linking agent.
Above-mentioned concentrated organic facies can place Nitrogen evaporator (for example selecting for use Hangzhou Ao Sheng Instr Ltd. to produce) to carry out.
Further improvement as the method for preparing of anti-bacterial hydrogel dressing of the present invention: the hydroxyl carbowax molecular weight in the step 1) is 100～10000.
Further improvement as the method for preparing of anti-bacterial hydrogel dressing of the present invention: step 2), natural macromolecular material is glucosan, hyaluronic acid, chitosan, collagen, carrageenan, gelatin or agar, contains Ag
+The diameter of ZnO nano-particle be 1～15nm.
In step 1) of the present invention, oxolane will be selected exsiccant oxolane for use, be raw oxolane; Can be earlier hydroxyl carbowax be dewatered (purpose be guarantee in the hydroxyl carbowax not moisture) through methylbenzene azeotropic, and then be dissolved in the exsiccant oxolane; In step 3), can obtain difform gel through in difform mould, carrying out polymerization, the solid content of gained anti-bacterial hydrogel dressing is 5～35%.In the present invention, room temperature generally is meant 0～35 ℃.
Inventor of the present invention is in research process; Made full use of the excellent biological compatibility of natural macromolecular material; And adopt irradiation technique that the macromolecule and the natural macromolecular material of synthetic are carried out organic assembling, finally obtain a kind of holey dressing with anti-microbial property and hydrating capacity; This holey dressing can be widely used in clinical treatment as a kind of novel skin dressing.
Dressing of the present invention is by acrylamide, natural polymer (like collagen, hyaluronic acid, chitosan and alginic acid etc.) and contains Ag
+ZnO be composited, compare traditional dressing and have higher biocompatibility and stronger hydrating capacity, be easy to remove from wound surface.
In sum; The present invention utilizes irradiation crosslinking technological, with the Polyethylene Glycol double methacrylate macromolecule of synthetic and natural macromolecular material polymerization with good biocompatibility, in the space of polymeric material, insert simultaneously nanometer Ag+; The basic function of make the dressing that finally prepares adhesiveness is good except having, isolate bacteria, maintenance wound surface are moistening; Also have antibiotic, as to promote the healing of wound surface skin repair function, owing to have polyethylene glycol structures in this structure, make it have stronger hydration capability simultaneously; Make gel film when wound surface is removed, can not damage wound surface once more.
The specific embodiment
The method for preparing of embodiment 1, a kind of anti-bacterial hydrogel dressing, carry out following steps successively:
1) will be dissolved in the dry tetrahydrofuran of 200ml through the 50g hydroxyl carbowax (molecular weight is 2000) after methylbenzene azeotropic removes water treatment; Under ice bath, slowly drip (15 droplets/minute) 25ml acryloyl chloride; Drip off the recession deicing and bathe, under nitrogen protection, react 8h at room temperature.With the reactant elimination solid of gained, get clear liquid; At 60 ℃ of evaporate to dryness clear liquids, get crude product.Crude product with three times (200ml * 3) of saturated nacl aqueous solution washing, is dissolved in the 100ml dichloromethane then, places Nitrogen evaporator (Hangzhou Ao Sheng Instr Ltd.) to concentrate organic facies, make liquor capacity be decreased to 40% of original volume; Add the 30ml ether sedimentation, the gained precipitate is Polyethylene Glycol double methacrylate cross-linking agent.
2) with the 5g particle diameter be the Ag that contains of 8～12nm
+The ZnO nano-particle (buy ten thousand scape new material company limiteies from Hangzhou; The mol ratio of Ag: Zn=1: 4) adding water, to be mixed with mass concentration be 15% nano aqueous solution; Collagen with 50g dissolves in the above-mentioned nano aqueous solution then, prepares the collagenic aqueous solution that contains nanometer Ag.
3) in the 100g acrylamide, add whole steps 2) collagenic aqueous solution of preparation gained, add the Polyethylene Glycol double methacrylate cross-linking agent of whole step 1) gained simultaneously, place under the room temperature
60Co source cross-linking radiation, the control exposure dose is 60KGy, obtains the anti-bacterial hydrogel dressing that thickness is 0.5mm through in mould, carrying out polymerization, its solid content is 31.8%.
The method for preparing of embodiment 2, a kind of anti-bacterial hydrogel dressing is with embodiment 1 step 2) in collagen make glucosan into; The glucan aqueous solution that must contain nanometer Ag; With the collagenic aqueous solution in embodiment 1 step 3) make glucan aqueous solution into, exposure dose changes 40KGy into; All the other are all with embodiment 1.
Obtain the anti-bacterial hydrogel dressing that thickness is 0.5mm through in mould, carrying out polymerization, its solid content is 25.0%.
The method for preparing of embodiment 3, a kind of anti-bacterial hydrogel dressing will be implemented 1 step 2) in collagen make hyaluronic acid into; The hyaluronic acid aqueous solution that must contain nanometer Ag; With the collagenic aqueous solution in embodiment 1 step 3) make hyaluronic acid aqueous solution into, exposure dose changes 80KGy into; All the other are all with embodiment 1.
Obtain the anti-bacterial hydrogel dressing that thickness is 0.5mm through in mould, carrying out polymerization, its solid content is 33.8%.
The method for preparing of embodiment 4, a kind of anti-bacterial hydrogel dressing, carry out following steps successively:
1) will be dissolved in the dry tetrahydrofuran of 200ml through the 50g hydroxyl carbowax (molecular weight is 2000) after methylbenzene azeotropic removes water treatment, under ice bath, slowly drip the 25ml acryloyl chloride, drip off the recession deicing and bathe, under nitrogen protection, react 8h at room temperature.With the reactant elimination solid of gained,, get crude product at 60 ℃ of evaporate to dryness clear liquids.Crude product is washed three times (200ml * 3) with saturated nacl aqueous solution; Be dissolved in then in the 100ml dichloromethane; Place Nitrogen evaporator (Hangzhou Ao Sheng Instr Ltd.) to concentrate organic facies; Make liquor capacity be decreased to 40% of original volume, add the 30ml ether sedimentation, the gained precipitate is Polyethylene Glycol double methacrylate cross-linking agent.
2) with the 5g particle diameter be the Ag that contains of 1～6nm
+The ZnO nano-particle (buy ten thousand scape new material company limiteies from Hangzhou; The mol ratio of Ag: Zn=1: 4) adding water, to be mixed with mass concentration be 15% nano aqueous solution; Chitosan with 50g dissolves in the above-mentioned nano aqueous solution then, prepares the chitosan aqueous solution that contains nanometer Ag.
3) in the 100g acrylamide, add Overall Steps 2) chitosan aqueous solution of preparation gained, add Overall Steps 1 simultaneously) the Polyethylene Glycol double methacrylate cross-linking agent of gained, place under the room temperature
60Co source cross-linking radiation, the control exposure dose is 50KGy, obtains the anti-bacterial hydrogel dressing that thickness is 0.5mm through in mould, carrying out polymerization, its solid content is 27.2%.
Embodiment 5, with the step 2 of embodiment 4) in the mass concentration of nano aqueous solution make 20% into by 15%, all the other are with embodiment 4.Obtain the anti-bacterial hydrogel dressing that thickness is 0.5mm, its solid content is 27.2%.
Embodiment 6, with the step 2 of embodiment 4) in the mass concentration of nano aqueous solution make 25% into by 15%, all the other are with embodiment 4.Obtain the anti-bacterial hydrogel dressing that thickness is 0.5mm, its solid content is 27.2%.
Embodiment 7, with the step 2 of embodiment 4) in the mass concentration of nano aqueous solution make 30% into by 15%, all the other are with embodiment 4.Obtain the anti-bacterial hydrogel dressing that thickness is 0.5mm, its solid content is 27.2%.
Experiment 1, laboratory animal adopt male Wistar rat, and point of observation is respectively hinders back 3,7,14,21d, puts 10 animals mutually at every turn.Rat back is with 8% sodium sulfide loss of thick fluid hair, and 24h is after the abdominal cavity gives pentobarbital sodium, anaesthetizes successfully the back and scalds with 80 ℃ of water-baths and caused rat back 10% dark II degree skin scald (sick inspection section confirmation) in 15 seconds, and wound is after the abdominal cavity gives 5ml normal saline.Respectively with the anti-bacterial hydrogel dressing flap coverage of embodiment 1～embodiment 7 gained, as experimental group 1～experimental group 7; With Omiderm (the external high like product of a kind of clinical frequency of utilization, its thickness is 0.5mm) flap coverage, group as a comparison; Calculate the wound healing rate in each sampling time point.
It is following to calculate wound healing rate method: earlier wound surface is traced on onionskin, again as template, the uniform hard paper of quality is cut into onesize, weigh in the balance then heavily, represent wound surface area size indirectly with hard paper weight.Be calculated as follows the wound healing rate: wound healing rate (%)=(original wound surface area-the wound surface area does not heal)/original wound surface area.Pathologic finding is understood the wound healing quality, and confirms healing time according to the wound healing situation.Experimental result such as following table 1:
Table 1
| The sampling natural law | 3d | 7d | 14d | 21d | |
| Experimental group 1 | The average healing rate of wound surface | 22.7％ | 37.4％ | 64.4％ | 92.1％ |
| Experimental group 2 | The average healing rate of wound surface | 27.2％ | 39.7％ | 67.5％ | 89.0％ |
| Experimental group 3 | The average healing rate of wound surface | 21.5％ | 34.4％ | 59.1％ | 87.3％ |
| Experimental group 4 | The average healing rate of wound surface | 24.7％ | 35.1％ | 62.5％ | 86.2％ |
| Experimental group 5 | The average healing rate of wound surface | 25.5％ | 36.0％ | 63.0％ | 85.9％ |
| Experimental group 6 | The average healing rate of wound surface | 25.1％ | 35.8％ | 62.7％ | 86.6％ |
| Experimental group 7 | The average healing rate of wound surface | 24.5％ | 35.7％ | 63.2％ | 87.0％ |
| Contrast groups | The average healing rate of wound surface | 9.5％ | 20.0％ | 45.1％ | 74.5％ |
Experiment 2, experiment method are hindered and were removed dressing in back 30 days with experiment 1, through naked-eye observation: do not see the rat skin tissue on the anti-bacterial hydrogel dressing of embodiments of the invention 1～embodiment 7, and Omiderm can obviously see a spot of rat skin tissue.
Experiment 3, various antibacterials as nuisance are adsorbed to the anti-bacterial hydrogel dressing and the Omiderm (as negative control) of embodiment 1～embodiment 7 gained respectively, carry out antibacterial ring test according to " disinfection technology standard " (2002), gained result such as following table 2:
Table 2
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (4)
1. the method for preparing of an anti-bacterial hydrogel dressing is characterized in that may further comprise the steps:
1), hydroxyl carbowax is dissolved in the oxolane, under ice bath, drip acryloyl chloride, the mol ratio of said acryloyl chloride and hydroxyl carbowax is 3: 1～20: 1; Drip off the recession deicing and bathe, under nitrogen protection, in room temperature, reacted 8～10 hours;
With the product elimination solid of gained, get clear liquid; With the clear liquid evaporate to dryness, get crude product again; Crude product gets Polyethylene Glycol double methacrylate cross-linking agent after washing and concentrating;
2), will contain Ag
+The ZnO nano-particle to be mixed with mass concentration be 15～30% nano aqueous solution, the mol ratio of said Ag: Zn=1: 4; Then natural macromolecular material is dissolved in the said nano aqueous solution, must contain the natural polymer aqueous solution of nanometer Ag; Said natural macromolecular material is 10: 1～50: 1 with the mass ratio that contains the ZnO nano-particle of Ag+;
Said natural macromolecular material is glucosan, hyaluronic acid, chitosan, collagen, carrageenan, gelatin or agar;
3), with acrylamide, Polyethylene Glycol double methacrylate cross-linking agent with contain the water-soluble liquid-phase mixing of natural polymer of nanometer Ag; The mass ratio of acrylamide and natural macromolecular material is 1: 1～20: 1, and the mass ratio of acrylamide and hydroxyl carbowax is 1.8～2.2: 1; Place under the room temperature then
60Co source cross-linking radiation, irradiation dose are 20～100KGy; Get anti-bacterial hydrogel dressing.
2. the method for preparing of anti-bacterial hydrogel dressing according to claim 1 is characterized in that: in the said step 1), earlier with crude product with saturated nacl aqueous solution washing three times, be dissolved in then in the dichloromethane, the reconcentration organic facies makes liquor capacity be decreased to 40%; The deposition that adds diethyl ether at last, the gained precipitate is Polyethylene Glycol double methacrylate cross-linking agent.
3. the method for preparing of anti-bacterial hydrogel dressing according to claim 1 and 2, it is characterized in that: the hydroxyl carbowax molecular weight in the said step 1) is 100～10000.
4. the method for preparing of anti-bacterial hydrogel dressing according to claim 3 is characterized in that: said step 2), contain Ag
+The diameter of ZnO nano-particle be 1～15nm.
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| CN101791425B (en) * | 2010-03-30 | 2013-04-10 | 赵雪林 | Antibacterial heal-promoting gel material used for preparing medical wound dressing and preparation method thereof |
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| CN111658819A (en) * | 2020-06-24 | 2020-09-15 | 四川大学华西医院 | Triblock hydrogel copolymer with temperature response and preparation method thereof |
| CN113274543A (en) * | 2021-05-19 | 2021-08-20 | 吉林大学 | Preparation method and application of novel adhesive antibacterial temperature-tolerant functional hydrogel |
| CN113980185B (en) * | 2021-12-13 | 2023-09-15 | 河南汇博医疗股份有限公司 | Amorphous silver-containing long-acting antibacterial hydrogel dressing with photocrosslinking curing function and preparation method thereof |
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| CN1880363A (en) * | 2000-10-30 | 2006-12-20 | 施托克赫森有限公司 | Absorbent material with improved blocking properties |
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