CN101530629A - Method for preparing photo-crosslinking chitosan hydrogel film - Google Patents
Method for preparing photo-crosslinking chitosan hydrogel film Download PDFInfo
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- CN101530629A CN101530629A CN200910024842A CN200910024842A CN101530629A CN 101530629 A CN101530629 A CN 101530629A CN 200910024842 A CN200910024842 A CN 200910024842A CN 200910024842 A CN200910024842 A CN 200910024842A CN 101530629 A CN101530629 A CN 101530629A
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Abstract
The invention discloses a method for preparing a photo-crosslinking chitosan hydrogel film. Biocompatible macromolecular chitosan as an initiator is subjected to chemical modification and introduced with hydroxypropyl and nitrine radicals at the 6-O site and N site respectively to form water-soluble photo-crosslinking chitosan; and the water solution of the photo-crosslinking chitosan is irradiated by ultraviolet light to form chitosan hydrogel so as to obtain the photo-crosslinking chitosan hydrogel film. The photo-crosslinking chitosan hydrogel film formed by a chitosan hydrogel film through ultraviolet light crosslinking by a physical method avoids chemical crosslinking with biological toxicity, improves the biocompatibility of the chitosan hydrogel film, realizes the clinical application of the chitosan hydrogel film, and provides a new path for the clinical application of the chitosan hydrogel film.
Description
Technical field
The invention belongs to the natural macromolecular material technical field, be specifically related to a kind of preparation method of photo-crosslinking chitosan hydrogel film.
Background technology
In the many decades in the past, the exploitation of novel wound healing film has caused that people more and more note.Generally believe that an ideal wound healing film not only will make wound surface avoid bacterial infection, and should form good biocompatibility, moistening healing environment.Traditional (non-airtight) wound healing film can only provide basic healing condition for wound, but still be currently marketed leading products.The wound healing aquagel membrane is a kind of seal film, can provide moistening healing environment for wound, its application prospect and extensive.
By the hydrogel that hydrophilic macromolecule forms by various crosslinked actions, minimum to inflammatory reaction, thrombosis and tissue injury that organism causes, showed its excellent biological compatibility.Hydrogel is to form by hydrophilic macromolecule is crosslinked, can absorb a large amount of moisture content and don't cause itself dissolving, so hydrogel has similar feature to the soft tissue of organism; In addition, hydrogel material is to oxygen, and nutrient substance and other water miscible metabolite have high osmosis.Based on above character, hydrogel material has the potentiality that become desirable wound healing film.For instance, a kind of commercialization aerogel dressing ' Geliperm that is gone by polyacrylamide and agar staggered-mesh
', can provide good physiological condition for wound healing.This smooth, flexible, transparent commercialization aerogel dressing contains 96% bound water.It allows gas molecule, inorganic salt, metabolite and protein to see through, and but can stop the intrusion of antibacterial.This aerogel dressing is nontoxic and do not have no any zest.But also have report to point out this material only for being used for the sealing of interim wound because it to the wound adhesion a little less than and a little less than structure also is highly brittle, so this material can only be applied to the clean faster wound of healing rate, as skin donor site and superficial second degree burn.
Recently, Balakrishnan etc. has reported the aerogel dressing that a kind of original position forms.This aerogel dressing is crosslinked and form under the condition of the boric acid solution that adds trace by gelatin and oxidation alginate.Compare with other hydrogel material, original position forms hydrogel and has a lot of advantages, because it allows hydrogel original position to form and to be attached on the wound of complicated shape.That the overwhelming majority that can access on the present market considers on the compliance to wound with the wound dressing that sheet and form membrane are sold and thoughtful inadequately.Therefore, on the compliance this point, the dressing that original position forms is better than these prefabricated dressing.Except compliance, this material also has the character that much becomes desirable wound dressing, for example: good water absorption rate, best moisture-vapor transmission (WVTR), certain antibiotic property and biodegradable.But the hydrogel that this original position forms is that the alginic acid dialdehyde sodium that obtained by reaction and gelatin are crosslinked and form.According to the result of study of Draye etc., the dialdehyde of trace may be released from hydrogel and cause the cytotoxicity of hydrogel.This situation is followed by discharging glutaraldehyde in the biomaterial of glutaraldehyde cross-linking and is caused Cytotoxic situation similar.In the experiment of cell culture, the dialdehyde sill demonstrates pair cell and duplicates very big influence.
For solving Cytotoxic problem, very fast for the progress of the photocrosslinkable hydrogel that does not need chemical cross-linking agent.The photo-crosslinking effect also can make formation covalent bond between the macromolecule and prepare hydrogel.This crosslinked action is the cross linked polymer molecule fast and effectively, and the formation of hydrogel is had controlled on time and the space.Recently, a kind of aquagel of ultraviolet photo-initiated crosslinking has caused a lot of people's concern.On the amino of chitosan, introduce lactose base (lactobionic acid) and azido (azidobenzoic acid) to obtain the derivant of this chitosan.The chitosan derivatives that the lactose base replaces can dissolve in the aqueous solution of pH neutral, and azido makes this chitosan derivatives that the photo-crosslinking effect can take place.
This patent has been invented a kind of novel photo-crosslinking chitosan hydrogel film.At first, the hydroxypropyl that carries out to chitosan replaces the water solublity of raising chitosan; Then, chitosan-the N position introduces Photocrosslinkable group, azido group; Solution with this chitosan derivatives of irradiation under ultraviolet ray can prepare the chitosan hydrogel film with bioadhesive.The result shows, this photo-crosslinking chitosan hydrogel film have conveniently use, compliance is good, comfort level is high characteristics, be highly profitable for the recovery of patient's wound; It also has in the best moist environment of a wound face long term of maintenance and the advantage of short cell migration.The biocompatibility of this chitosan hydrogel film is good, has very wide application prospect as wound dressing.
Summary of the invention
The purpose of this invention is to provide a kind of method for preparing photo-crosslinking chitosan hydrogel film.
The method for preparing photo-crosslinking chitosan hydrogel film provided by the present invention, with the chitosan is starting material, at first in isopropanol solvent, alkalize, then with Tetramethylammonium hydroxide as catalyst, obtain the hydroxypropyl chitosan that 6-O replaces with propylene oxide reaction; Acylation reaction takes place under certain condition in the amino of hydroxypropyl chitosan and 4-azidobenzoic acid, introduces the azido group of light reaction, obtains the chitosan of Photocrosslinkable; With the aqueous solution several seconds of the certain density Photocrosslinkable chitosan of irradiation under ultraviolet ray, obtain the aquagel membrane of chitosan then.
In the said method, the proportioning of chitosan and isopropyl alcohol is 0.05～10g/ml, and when the quality of reactant chitosan was 25g, the consumption of the sodium hydroxide solution of 33% (mass fraction) was 10～100ml.
In the said method, the consumption of the tetramethylammonium hydroxide aqueous solution of catalyst 10% is 10～100ml, and the consumption of expoxy propane is 100～1000ml, and the response time is 5～50 hours.
In the said method; the acylation reaction condition of hydroxypropyl chitosan and 4-azidobenzoic acid is: when the quality of hydroxypropyl chitosan is 10g; 50mM N; N; N ', the consumption of N '-tetramethylethylenediamine (TEMED) solution is 1～200ml, the consumption of dicyclohexylcarbodiimide (EDC) is 0.1～10g; the consumption of 4-azidobenzoic acid is 0.1～10mg
In the said method, the time of the acylation reaction of hydroxypropyl chitosan and 4-azidobenzoic acid is 1～100h.
In the said method, the concentration that forms the needed Photocrosslinkable chitosan of photo-crosslinking chitosan gel film is 1～80mg/ml, and the power of needed ultraviolet light is 1～100W, and wavelength is 200～500nm, and irradiation time is 1～1000s.
The concrete operations step of the preparation of the photo-crosslinking chitosan film that the present invention proposes is as follows: the preparation hydroxypropyl chitosan, stirred 30 minutes in chitosan adding 2.5～500ml isopropyl alcohol of 25g, the sodium hydroxide solution that adds 10～100ml 33% (mass fraction), freezing under-20 ℃ behind the stirring 1h.Then, add the tetramethylammonium hydroxide aqueous solution of 10～100ml 10% (volume fraction), add 100～1000ml expoxy propane again, stirring reaction is 1 hour under the room temperature, and reaction temperature slowly rises to 60 ℃, and the response time is 5～50h.With alcoholic solution precipitation product, to filter, the washing with alcohol twice with 95% is used deionized water dissolving, and dialysis, lyophilizing promptly obtain the hydroxypropyl chitosan that the 6-O position replaces.Preparation Photocrosslinkable chitosan, the above-mentioned hydroxypropyl chitosan of 10g is dissolved in the TEMED aqueous solution of 50mM of 1～200ml, add the EDC of 0.1～10g and the 4-azidobenzoic acid of 0.1～10g, stirring at room reaction 1～100h, dialysis, lyophilizing obtain the Photocrosslinkable chitosan.Preparation photo-crosslinking chitosan hydrogel film, 400 μ l concentration are that to be coated on diameter be in the 7cm culture dish to the Photocrosslinkable chitosan aqueous solution of 1～80mg/ml.With wavelength is 200～500nm, and power is the culture dish that the UV illumination of 1～100W is penetrated coating Photocrosslinkable chitosan, and irradiation time 1～1000s obtains photo-crosslinking chitosan hydrogel film.
Compare with existing aquagel membrane, the present invention has following characteristics: at first, chitosan is the natural biological macromolecule, the source is very extensive, safety non-toxic, cheap, compare with synthetic high polymer, have excellent biological compatibility and biodegradability, so chitosan hydrogel film has very high environment friendly and biological safety as wound dressing.Secondly, the method for preparing aquagel membrane by chemical crosslinking is changed in the present invention, and adopts the method for photo-crosslinking, has reduced the toxicity of aquagel membrane to organism.Show by the mensuration that photo-crosslinking chitosan hydrogel film water absorption rate involved in the present invention, moisture-vapor transmission, moisture is kept and sticks intensity, this hydrogel is as wound dressing, can on wound face, keep a moist environment for a long time, thereby can promote the epithelization of wound, the healing of accelerated in wounds.Therefore, the present invention is aspect biocompatibility or all there are many superioritys in the medical application aspect, has good DEVELOPMENT PROSPECT.
Description of drawings
Fig. 1 a and b are the environmental scanning electron microscope picture of photo-crosslinking chitosan hydrogel film
C is the scanning electron microscope diagram sheet of the photo-crosslinking chitosan hydrogel film of dehydration
The specific embodiment
Below utilize embodiment to further describe the present invention, but can not think to limit scope of invention.
Embodiment 1: the preparation of water soluble hydroxypropyl chitosan
Stirred 30 minutes in the 40g chitosan adding 250ml isopropyl alcohol.Then mixture add the 30ml sodium hydroxide solution (33%, w/v).Mixed solution at room temperature adds flask and sealing after stirring 1h, and-20 ℃ of following freeze overnight.The catalyst solution (Tetramethylammonium hydroxide) that drips 40ml 10% (v/v) is in mixture, and then adding 400ml expoxy propane.Stirring reaction 1h under the room temperature, reaction temperature slowly rises to 60 ℃, and the response time is 7h.Reactant liquor is joined in 4 times of volume of ethanol solution, obtain precipitation, with 10 times of volume of ethanol washing precipitations twice, with deionized water dissolution precipitation again, dialysis, lyophilizing promptly obtain highly purified hydroxypropyl chitosan.
Embodiment 2: the preparation of Photocrosslinkable chitosan
The hydroxypropyl chitosan of getting 10g preparation is dissolved in the 50mM TEMED solution of 50ml and stirs, and stirs and all dissolves up to hydroxypropyl chitosan, adds the EDC of 5g and the 4-azidobenzoic acid of 10g.Stirring reaction 50h under the condition that room temperature is 25 ℃.Dialysis two days, lyophilizing obtain the Photocrosslinkable chitosan in deionized water.
Embodiment 3: the preparation of photo-crosslinking chitosan hydrogel film
400 μ l concentration are that to be coated on diameter be in the 7cm culture dish to the Photocrosslinkable chitosan aqueous solution of 40mg/ml.With the wavelength is 365nm, and power is the culture dish that the UV illumination of 20W is penetrated coating Photocrosslinkable chitosan, and irradiation time 500s obtains the photo-crosslinking chitosan hydrogel film that thickness is about 0.1mm.
Embodiment 4: they with the natural polymer chitosan starting material, and the preparation of photo-crosslinking chitosan hydrogel film
Stirred 30 minutes in the 100g chitosan adding 250ml isopropyl alcohol.Then mixture add the 20ml sodium hydroxide solution (33%, w/v).Mixed solution at room temperature adds flask and sealing after stirring 1h, and-20 ℃ of following freeze overnight.The catalyst solution (Tetramethylammonium hydroxide) of Dropwise 5 0ml 10% (v/v) is in mixture, and then adding 200ml expoxy propane.Stirring reaction 1h under the room temperature, reaction temperature slowly rises to 60 ℃, and the response time is 10h.Reactant liquor is joined in 4 times of volume of ethanol solution, obtain precipitation, with 10 times of volume of ethanol washing precipitations twice, with deionized water dissolution precipitation again, dialysis, lyophilizing promptly obtain highly purified hydroxypropyl chitosan.The hydroxypropyl chitosan of getting 10g preparation is dissolved in the 50mM TEMED solution of 100ml and stirs, and stirs and all dissolves up to hydroxypropyl chitosan, adds the EDC of 0.5g and the 4-azidobenzoic acid of 5g.Stirring reaction 50h under the condition that room temperature is 25 ℃.Dialysis two days, lyophilizing obtain the Photocrosslinkable chitosan in deionized water.
400 μ l concentration are that to be coated on diameter be in the 7cm culture dish to the Photocrosslinkable chitosan aqueous solution of 10mg/ml.With the wavelength is 365nm, and power is the culture dish that the UV illumination of 40W is penetrated coating Photocrosslinkable chitosan, and irradiation time 10s obtains the photo-crosslinking chitosan hydrogel film that thickness is about 0.1mm.
Embodiment 5: the form of photo-crosslinking chitosan hydrogel film
Aqueous photo-crosslinking chitosan hydrogel film is placed on the cold platform of Peltier of environmental scanning electron microscope (FEI Quanta-200) of 4 ℃ of ambient temperatures, at voltage is 20kV, and sample room steam pressure is that the form of this aquagel membrane of observation under 4.0 to 4.7Torr the condition is seen accompanying drawing 1.The photo-crosslinking chitosan hydrogel film that lyophilization obtains dewatering, under the condition of high pressure, 0.1Torr, 1.2kV and 50mA, at the thick native gold of the photo-crosslinking chitosan hydrogel film surface spraying 500 * 10-8cm of dehydration, the form of the photo-crosslinking chitosan hydrogel film of observation dehydration is seen accompanying drawing 1 under scanning electron microscope with the HitachiIB-2 flush coater.
Claims (8)
1, a kind of photo-crosslinking chitosan hydrogel film, it is characterized in that it being to prepare: be starting material with the chitosan by following process, at first in isopropanol solvent, alkalize, then with Tetramethylammonium hydroxide as catalyst, obtain the hydroxypropyl chitosan that 6-O replaces with propylene oxide reaction; Acylation reaction takes place under certain condition in the amino of hydroxypropyl chitosan and 4-azidobenzoic acid, introduces the azido group of light reaction, obtains the chitosan of Photocrosslinkable; With the aqueous solution several seconds of the certain density Photocrosslinkable chitosan of irradiation under ultraviolet ray, obtain the aquagel membrane of chitosan then.
2, photo-crosslinking chitosan hydrogel film according to claim 1, the proportioning that it is characterized in that chitosan and isopropyl alcohol is 0.05～10g/ml, when the quality of chitosan was 25g, the consumption of the sodium hydroxide solution of 33% (mass fraction) was 10～100ml.
3, photo-crosslinking chitosan hydrogel film according to claim 1, the consumption that it is characterized in that the tetramethylammonium hydroxide aqueous solution of catalyst 10% is 10～100ml, and the consumption of expoxy propane is 100～1000ml, and the response time is 5～50 hours.
4, photo-crosslinking chitosan hydrogel film according to claim 1; the acylation reaction condition that it is characterized in that hydroxypropyl chitosan and 4-azidobenzoic acid is: when the quality of hydroxypropyl chitosan is 10g; 50mM N; N; N '; the consumption of N '-tetramethylethylenediamine (TEMED) solution is 1～200ml, and the consumption of dicyclohexylcarbodiimide (EDC) is 0.1～10g, and the consumption of 4-azidobenzoic acid is 0.1～10mg.
5, photo-crosslinking chitosan hydrogel film according to claim 1, the time that it is characterized in that the acylation reaction of hydroxypropyl chitosan and 4-azidobenzoic acid is 1～100h.
6, photo-crosslinking chitosan hydrogel film according to claim 1, the concentration that it is characterized in that forming the needed Photocrosslinkable chitosan of photo-crosslinking chitosan gel film is 1～80mg/ml.
7, photo-crosslinking chitosan hydrogel film according to claim 1, the power that it is characterized in that forming the needed ultraviolet light of photo-crosslinking chitosan gel film is 1～100W, and wavelength is 200～500nm, and irradiation time is 1～1000s.
8, a kind of preparation method of photo-crosslinking chitosan hydrogel film, it is characterized in that concrete steps are as follows: the preparation hydroxypropyl chitosan, stirred 30 minutes in chitosan adding 2.5～500ml isopropyl alcohol of 25g, the sodium hydroxide solution that adds 10～100ml 33% (mass fraction), freezing under-20 ℃ behind the stirring 1h.Then, add the tetramethylammonium hydroxide aqueous solution of 10～100ml10% (volume fraction), add 100～1000ml expoxy propane again, stirring reaction 1h under the room temperature, reaction temperature slowly rises to 60 ℃, and the response time is 5～50h.With alcoholic solution precipitation product, to filter, the washing with alcohol twice with 95% is used deionized water dissolving, and dialysis, lyophilizing promptly obtain the hydroxypropyl chitosan that the 6-O position replaces.Preparation Photocrosslinkable chitosan, the above-mentioned hydroxypropyl chitosan of 10g is dissolved in the TEMED aqueous solution of 50mM of 1～200ml, add the EDC of 0.1～10g and the 4-azidobenzoic acid of 0.1～10g, stirring at room reaction 1～100h, dialysis, lyophilizing obtain the Photocrosslinkable chitosan.Preparation photo-crosslinking chitosan hydrogel film, 400 μ l concentration are that to be coated on diameter be in the 7cm culture dish to the Photocrosslinkable chitosan aqueous solution of 1～80mg/ml.With wavelength is 200～500nm, and power is the culture dish that the UV illumination of 1～100W is penetrated coating Photocrosslinkable chitosan, and irradiation time 1～1000s obtains photo-crosslinking chitosan hydrogel film.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464727A (en) * | 2010-11-10 | 2012-05-23 | 江春艳 | Beta-glucan hydroxypropyl derivative and its preparation method and application |
| CN102516568A (en) * | 2011-11-23 | 2012-06-27 | 天津大学 | Preparation method of chitosan-base photocrosslinked aquagel |
| CN102675484A (en) * | 2012-05-18 | 2012-09-19 | 华南理工大学 | Synthetic method of 4-hydrazoic benzoyl chitosan |
| CN105131760A (en) * | 2015-08-28 | 2015-12-09 | 大禹节水（天津）有限公司 | Moisture holding coating for embedded drip irrigation belt and preparing method |
| CN107619483A (en) * | 2017-10-09 | 2018-01-23 | 河南聚硒农业科技有限公司 | A kind of preparation method of selenizing Sodium Alginate Hydrogel Films |
| CN107854721A (en) * | 2017-11-07 | 2018-03-30 | 青岛大学 | A kind of anti-bacterial hydrogel and preparation method thereof |
| CN109971009A (en) * | 2019-04-11 | 2019-07-05 | 青岛科技大学 | Preparation method and applications of the photoresponse without support film |
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2009
- 2009-02-27 CN CN200910024842A patent/CN101530629A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464727A (en) * | 2010-11-10 | 2012-05-23 | 江春艳 | Beta-glucan hydroxypropyl derivative and its preparation method and application |
| CN102516568A (en) * | 2011-11-23 | 2012-06-27 | 天津大学 | Preparation method of chitosan-base photocrosslinked aquagel |
| CN102675484A (en) * | 2012-05-18 | 2012-09-19 | 华南理工大学 | Synthetic method of 4-hydrazoic benzoyl chitosan |
| CN105131760A (en) * | 2015-08-28 | 2015-12-09 | 大禹节水（天津）有限公司 | Moisture holding coating for embedded drip irrigation belt and preparing method |
| CN107619483A (en) * | 2017-10-09 | 2018-01-23 | 河南聚硒农业科技有限公司 | A kind of preparation method of selenizing Sodium Alginate Hydrogel Films |
| CN107619483B (en) * | 2017-10-09 | 2020-07-14 | 河南省乡振农村创业服务有限公司 | Preparation method of selenylation sodium alginate hydrogel |
| CN107854721A (en) * | 2017-11-07 | 2018-03-30 | 青岛大学 | A kind of anti-bacterial hydrogel and preparation method thereof |
| CN107854721B (en) * | 2017-11-07 | 2021-04-20 | 青岛大学 | Antibacterial hydrogel and preparation method thereof |
| CN109971009A (en) * | 2019-04-11 | 2019-07-05 | 青岛科技大学 | Preparation method and applications of the photoresponse without support film |
| CN109971009B (en) * | 2019-04-11 | 2021-10-01 | 青岛科技大学 | Preparation method and application of photoresponse unsupported thin film |
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Application publication date: 20090916 |