CN101885906A - Degradable biological hydrogel and preparation method thereof - Google Patents
Degradable biological hydrogel and preparation method thereof Download PDFInfo
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- CN101885906A CN101885906A CN2010102312705A CN201010231270A CN101885906A CN 101885906 A CN101885906 A CN 101885906A CN 2010102312705 A CN2010102312705 A CN 2010102312705A CN 201010231270 A CN201010231270 A CN 201010231270A CN 101885906 A CN101885906 A CN 101885906A
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Abstract
The invention discloses a degradable biological hydrogel and a preparation method thereof, and relates to a hydrogel. The invention provides a quick-response and high-strength degradable biological hydrogel and a preparation method thereof, which can be applied in the field of biological medicaments. The degradable biological hydrogel is a double-network hydrogel having a porous structure, wherein a chitosan hydrogel is the first network; a polylactic acid-polyethylene glycol-polylactic acid block copolymer hydrogel blocked by a acrylate group is the second network; the mass ratio of the chitosan to the PEGLM is 1:(4-19); and the degradable biological hydrogel is prepared by a stepwise interpenetrating technique. The prepared hydrogel has the porous structure and provides a convenient channel for water and other substances, so the response speed of the gel is improved and swelling equilibrium can be achieved in 9 minutes. The double-network hydrogel is formed through the interpenetrating cooperation of rigid and flexible networks, so the mechanical strength of the gel is improved greatly, and the compressive strength of the gel can reach a maximum value of 1.08 MPa under the condition that the water content is more than 90 percent.
Description
Technical field
The present invention relates to a kind of hydrogel, especially relate to a kind of degradable biological hydrogel and preparation method thereof.
Background technology
Hydrogel be by hydrophilic polymer constitute can be in water swelling and keep large quantity of moisture and not dissolved cross-linked network.They are swellable to balance volume in water, and the deswelling that dewaters under certain condition (external stimuluss such as temperature, pH, ionic concn, electric field), is that a class set suction, water conservation, controlled release are in the polymer-function material of one.Hydrogel is similar to the vital tissues material, surface adhesin protein matter and cell ability are very weak, when contacting with blood, body fluid and tissue, show excellent biological compatibility, neither influence the metabolic process of life entity, meta-bolites can be discharged by hydrogel again.Hydrogel is similar to the extracellular matrix part in nature, can reduce friction and mechanical effect to surrounding tissue after the suction, significantly improves the biology performance of material.Because suction, water conservation and the bionical characteristic of its uniqueness, hydrogel are widely used in fields such as medicine and biological engineering material, can be used as tissue filling agent, medicine controlled releasing agent, contact lenses, artificial skin, artificial cartilage, tissue engineering bracket material etc.
Biological hydrogel comprises natural water gel and synthetic water gel, the natural water gelatinous material comprises collagen, scleroproein, hyaluronic acid, sodium alginate, chitosan etc., and polyvinyl alcohol (PVA), polyoxyethylene glycol (PEG) in the synthetic water gel, polylactic acid-polyglycol multipolymer (PLA-co-PEG) etc. is most widely used several gelatinous materials at present.
The hydrogel restraining factors that particularly the natural water gel is very fatal in actual applications mainly are that its response speed is slow and mechanical strength is poor.In recent years, the research that increasing scientific worker begins to be devoted to improve hydrogel rate of water absorption (response speed) is to satisfy the special requirement of aspects such as quick-acting haemostatic powder material, medicine controlled releasing.Therefore, porous aquagel begins slowly to enter people's sight with its unique water absorbing properties.The introducing of vesicular structure not only can improve the speed of response of gel in the gel, can also improve its water absorbent rate (Mohan Y M, Murthy P S K, Raju K M.Journal of Applied Polymer Science, 2006,101 (5): 3202-3214; Zhang Jiantao, Huang Shiwen, Wang Luling, etc. SCI, 2004,25:2370-2374; Zhang Jiantao, Huang Shiwen, Xue Yanan, etc. polymer journal, 2006 (3): 418-423.).Aspect the raising gel-strength, obvious results has following several gel: topological framework gel (OkumuraY, Ito K.Adv Mater, 2001,13:485-487.), nanostructure gel (Haraguchi K, Takehisa T.Adv Mater, 2002,14:1120-1124.), dual network gel (Gong JP, Katsuyama Y, Kurokawa T, Osada Y.Adv Mater 2003,15:1155-1158.), ordered structure (having homogeneous polymer chain length) gel (Takamasa Sakai, Takuro Matsunaga, Yuji Yamamoto, et al.Macromolecules 2008,41,5379-5384), in above-mentioned four kinds of gels, the investigator tends to research structure, the synthesized gel rubber that character is controlled, and more superior for biocompatibility, the research of degradable natural gel seldom.
Summary of the invention
The object of the present invention is to provide a kind of biomedicine field that can be applicable to, respond high-intensity degradable biological hydrogel and preparation method thereof fast.
Degradable biological hydrogel of the present invention is the double-network hydrogel with vesicular structure, the inflexible aquagel is first network, acrylate-based end capped polylactic acid-polyglycol-polylactic-acid block copolymer (PEGLM) hydrogel of flexible ultraviolet light cross-linking is second network, the mass ratio of chitosan: PEGLM is 1: (4～19) are preferably 1: 9.
Described deacetylating degree of chitosan 〉=85%, viscosity-average molecular weight are 500,000～1,000,000.
Among the described PEGLM, the molecular weight of polyoxyethylene glycol is 4000～6000, the polymerization degree of two ends poly(lactic acid) is 5～17, be labeled as nKLm, wherein nK represents the molecular weight of polyoxyethylene glycol, m represents the polymerization degree of two ends poly(lactic acid), and for example 6KL5 representative is that the molecular weight of polyoxyethylene glycol in the multipolymer is 6000, and the polymerization degree of two ends poly(lactic acid) is 5.(its synthetic method is referring to document Amarpreet S.Sawhney, Chandrashekhar P.Pathak, and Jeffrey A.Hubbell.Macromolecules, 1993,26:581-587)
The preparation method of described degradable biological hydrogel is as follows:
1) chitosan being dissolved in mass concentration is that to obtain mass concentration in 1%～5% the aqueous acetic acid be 1%～5% chitosan solution, it is that to obtain mass concentration be 5%～15% PEGLM solution for 1%～5% aqueous acetic acid that PEGLM is dissolved in mass concentration, chitosan solution and PEGLM solution are mixed, get mixed solution A;
2) in mixed solution A, add pore-creating agent, be stirred to the pore-creating agent dissolving, get mixing solutions B;
3) add light trigger in mixing solutions B, the system of being stirred to mixes, and vacuumizes de-bubble again, and the last nitrogen that feeds in system gets mixed solution C with the oxygen in the system of removing;
4) add chitosan crosslinked dose in mixed solution C, it is even to be stirred to system, pours in the mould again, places sealing bag, and crosslinking reaction obtains Semi-IPN gel A;
5) Semi-IPN gel A is placed irradiation under the ultraviolet light, make PEGLM take place to obtain dual network gel B after the crosslinking reaction;
6) dual network gel B is taken out from mould, be soaked in water, remove pore-creating agent, finally obtain having the degradable biological hydrogel of vesicular structure.
In step 1), press mass ratio, chitosan: PEGLM can be 1: (4～19).
In step 2) in, described pore-creating agent can be polyoxyethylene glycol etc., and the molecular weight of polyoxyethylene glycol can be 1000, and the consumption of described pore-creating agent is 0.02～0.15g/mL of total system.
In step 3), described light trigger can be 2,2-dimethyl-2-phenyl methyl phenyl ketone etc., and the consumption of described light trigger by mass percentage, can be 0.5%～2% of PEGLM.
In step 4), describedly in mixed solution C, add chitosan crosslinked dose, be preferably under the condition of ice bath, in mixed solution C, add chitosan crosslinked dose; The temperature of described crosslinking reaction can be 50～70 ℃, and the time of crosslinking reaction can be 1～3h; Described chitosan crosslinked dose can be glutaraldehyde etc., press mass ratio, chitosan: chitosan crosslinked dose can be 1: (0.2～0.4).
In step 5), the power of described ultraviolet lamp can be 500～1500W, and the time of described irradiation can be 20～60min.
In step 6), described being soaked in water preferably used distilled water immersion 3～7 days, during at interval change water to remove pore-creating agent.
The quick response high intensity degradable biological hydrogel of the present invention's preparation has the following advantages:
(1) be the feedstock production gel with nontoxic, the chitosan of good biocompatibility, acrylate-based end capped polylactic acid-polyglycol-polylactic-acid block copolymer, the good biocompatibility of gel, and weakly alkaline chitosan can in and the acid degradation product of poly(lactic acid), thereby reduce the non-specific aseptic inflammation reactivity that poly(lactic acid) acid degradation product causes.
(2) chitosan gel rubber can be degraded under the effect of N,O-Diacetylmuramidase in vivo, by regulating its molecular weight, deacetylation and degree of crosslinking, can regulate and control its degradation speed; Hydrolysis can take place in polylactic acid chain segment in acrylate-based end capped polylactic acid-polyglycol-polylactic-acid block copolymer gel, thereby make gel degradation, by the molecular weight of regulating polyoxyethylene glycol, the polymerization degree of two ends poly(lactic acid), can regulate and control the degradation speed of gel.Thereby the gel degradation speed of the present invention's preparation can be regulated and control to adapt to the needs of practical application.
(3) gel of the present invention's preparation has vesicular structure, and consumption size and the quantity that can regulate hole by the control pore-creating agent, vesicular structure provides passage more easily for the turnover of water and other materials, thereby the response speed of gel improves, in 9 minutes, can reach swelling equilibrium, be fit to be applied in aspects such as quick-acting haemostatic powder material, medicine controlled releasing.
(4) IPN by rigidity, flexible network cooperates the formation double-network hydrogel, the mechanical strength of gel is greatly improved, under the situation of water content＞90%, the compressive strength maximum of gel can reach 1.08MPa, and high mechanical strength is to significant in the application of aspects such as contact lenses, artificial skin, artificial cartilage, tissue engineering bracket material.
Description of drawings
Fig. 1 is PEGLM gel, the chitosan gel rubber of the embodiment of the invention 1, the infrared spectrum of chitosan.In Fig. 1, X-coordinate is wave number Waavenumber (cm
-1); Curve A, B, C represent PEGLM gel, chitosan gel rubber, chitosan respectively.
Fig. 2 is the SEM figure of gel surface after the hydrogel lyophilize of the embodiment of the invention 1.In Fig. 2, A: the pore-creating agent consumption is 0g/mL, and scale is 60 μ m, B: the pore-creating agent consumption is 0.15g/mL, and scale is 300 μ m; Chitosan crosslinked degree is 0.4g/g, and chitosan (deacetylation 95%, molecular weight 500,000): PEGLM (6KL7) mass ratio is 1: 9.
Fig. 3 is the hydrogel swelling kinetic curve at room temperature of the embodiment of the invention 1.In Fig. 3, X-coordinate is time T ime (min), and ordinate zou is swelling ratio Swelling Ratio; Curve a is 0.15g/g, and curve b is 0g/g.
Fig. 4 is the stress-strain curve of the gel of the embodiment of the invention 1 preparation with pure PEGLM gel, three kinds of gels of chitosan gel rubber.In Fig. 4, X-coordinate is strain Strain (%), and ordinate zou is stress Stress (MPa); Chitosan crosslinked degree is 0.4g/g, PEGLM (6KL7), chitosan (deacetylation 95%, molecular weight 500,000), chitosan (deacetylation 95%, molecular weight 500,000): PEGLM (6KL7) mass ratio is 1: 9 (the pore-creating agent consumption is 0.15g/mL); Curve A is pure PEGLM gel, and curve B is pure chitosan gel rubber, and curve C is the gel of preparation.
Embodiment
The invention will be further described below by embodiment.
Embodiment 1
1) chitosan with deacetylation 95%, molecular weight 500,000 is dissolved in the chitosan solution that obtains 3% (w/w) in 2% (w/w) dilute acetic acid aqueous solution, and PEGLM (6KL7) is dissolved into PEGLM (6KL7) solution that 2% (w/w) dilute acetic acid aqueous solution obtains 10% (w/w).By chitosan: PEGLM (6KL7) mass ratio is to take by weighing 1.00g chitosan solution and 2.70g PEGLM (6KL7) solution at 1: 9, mixes.
2) consumption by 0.15g/mL takes by weighing the 0.55g cetomacrogol 1000, adds in the mixing solutions of step 1), stirs polyoxyethylene glycol is dissolved fully.
3) in step 2) mixing solutions in add 27 μ L 2,10% ethanolic soln of 2-dimethyl-2-phenyl methyl phenyl ketone, the system of being stirred to mixes.Mixing solutions is vacuumized de-bubble, and the last nitrogen that feeds in system is with the oxygen in the system of removing.
4) under the condition of ice bath, in the mixing solutions of step 3), add the 0.24mL5% glutaraldehyde water solution while stirring, the system that is stirred to evenly (need to prove that stirring can not be too violent in this step, in order to avoid produce bubble in the system), then mixing solutions is poured in the transparent mould, place sealing bag, 50 ℃ are reacted 1h down, obtain Semi-IPN gel A.
5) gel A is placed the ultraviolet light of 1000W shine 20min down, obtain dual network gel B.
6) gel B is taken out from mould, uses distilled water immersion 3d, during change water one time every 6h, removing the pore-creating agent cetomacrogol 1000, thereby obtain having the double-network hydrogel of vesicular structure.
See the FTIR spectrogram (Fig. 1) of chitosan before end product double-network hydrogel and unreacted and PEGLM (6KL7), in the infrared spectrum of PEGLM (6KL7) gel (curve A), 1748cm
-1Be the stretching vibration peak of ester group C=O, 1110cm
-1Stretching vibration peak for C-O-C in the polyoxyethylene glycol (PEG); In the infrared spectrum of chitosan gel rubber (curve B), 1662cm
-1Be the stretching vibration peak of C=O in the amide group, 1568cm
-1For glutaraldehyde with amino crosslinking reaction takes place generates schiff bases after-stretching vibration peak of C=N-, 1409cm
-1Near peak is the flexural vibration peak of methyl, methylene radical, 1070cm
-1Near the peak be the stretching vibration peak that C6 and C3 go up C-O on the chitosan; There is 1748cm in (curve C) in the infrared spectrum of product double-network hydrogel
-1The stretching vibration peak of C=O, 1605cm
-1The peak at place is 1640cm among the PEGLM (6KL7)
-11662cm in water peak and the chitosan
-1, 1568cm
-1The stack back, peak at place forms, simultaneously 1110cm
-1Near peak is than the middle 1110cm of PEGLM (6KL7)
-1Near peak broadens, and this is owing to 1070cm in the chitosan
-1Near the synergetic result in peak than the spectrogram of PEGLM (6KL7), 1409cm occurs in the curve
-1The peak, these presentation of results products are the double-network hydrogel that forms behind PEGLM (6KL7), the chitosan interpenetrating.
The SEM figure of gel surface can find after comparison diagram 2A, the lyophilize of B hydrogel, and behind the adding pore-creating agent, the surface of hydrogel becomes vesicular structure from the smooth structure of densification.Can find that from Fig. 3 swelling kinetic curve behind the adding pore-creating agent, vesicular structure gel water absorption and swelling speed and equilibrium swelling multiplying power all are improved, the response speed of gel is greatly improved.The stress-strain curve of Fig. 4 can find that with pure PEGLM gel, chitosan gel rubber contrast the intensity of gel is greatly improved with the gel of preparation, by bringing up to more than the 1MPa about original 0.1MPa.
The gellifying property test result is compressive strength 1.08MPa, fully degradation time 30d.
Embodiment 2～7: reaction conditions changes chitosan, PEGLM kind, chitosan and the mass ratio of PEGLM, chitosan crosslinked dose consumption with embodiment 1, and the consumption of pore-creating agent the results are shown in Table 1.
Table 1
Claims (10)
1. degradable biological hydrogel, it is characterized in that for having the double-network hydrogel of vesicular structure, the inflexible aquagel is first network, the acrylate-based end capped polylactic acid-polyglycol-polylactic-acid block copolymer hydrogel of flexible ultraviolet light cross-linking is second network, the mass ratio of chitosan: PEGLM is 1: 4～19, is preferably 1: 9.
2. a kind of degradable biological hydrogel as claimed in claim 1 is characterized in that described deacetylating degree of chitosan 〉=85%, and viscosity-average molecular weight is 500,000～1,000,000.
3. a kind of degradable biological hydrogel as claimed in claim 1, it is characterized in that among the described PEGLM, the molecular weight of polyoxyethylene glycol is 4000～6000, the polymerization degree of two ends poly(lactic acid) is 5～17, be labeled as nKLm, wherein nK represents the molecular weight of polyoxyethylene glycol, and m represents the polymerization degree of two ends poly(lactic acid).
4. the preparation method of a kind of degradable biological hydrogel as claimed in claim 1 is characterized in that may further comprise the steps:
1) chitosan being dissolved in mass concentration is that to obtain mass concentration in 1%～5% the aqueous acetic acid be 1%～5% chitosan solution, it is that to obtain mass concentration be 5%～15% PEGLM solution for 1%～5% aqueous acetic acid that PEGLM is dissolved in mass concentration, chitosan solution and PEGLM solution are mixed, get mixed solution A;
2) in mixed solution A, add pore-creating agent, be stirred to the pore-creating agent dissolving, get mixing solutions B;
3) add light trigger in mixing solutions B, the system of being stirred to mixes, and vacuumizes de-bubble again, and the last nitrogen that feeds in system gets mixed solution C with the oxygen in the system of removing;
4) add chitosan crosslinked dose in mixed solution C, it is even to be stirred to system, pours in the mould again, places sealing bag, and crosslinking reaction obtains Semi-IPN gel A;
5) Semi-IPN gel A is placed irradiation under the ultraviolet light, make PEGLM take place to obtain dual network gel B after the crosslinking reaction;
6) dual network gel B is taken out from mould, be soaked in water, remove pore-creating agent, finally obtain having the degradable biological hydrogel of vesicular structure.
5. the preparation method of a kind of degradable biological hydrogel as claimed in claim 4, it is characterized in that pressing mass ratio in step 1), chitosan: PEGLM is 1: 4～19.
6. the preparation method of a kind of degradable biological hydrogel as claimed in claim 4, it is characterized in that in step 2) in, described pore-creating agent is a polyoxyethylene glycol, and the molecular weight of polyoxyethylene glycol is 1000, and the consumption of described pore-creating agent is 0.02～0.15g/mL of total system.
7. the preparation method of a kind of degradable biological hydrogel as claimed in claim 4 is characterized in that in step 3), and described light trigger is 2,2-dimethyl-2-phenyl methyl phenyl ketone, the consumption of described light trigger by mass percentage, is 0.5%～2% of PEGLM.
8. the preparation method of a kind of degradable biological hydrogel as claimed in claim 4 is characterized in that in step 4), describedly adds chitosan crosslinked dose in mixed solution C, is under condition of ice bath, adds chitosan crosslinked dose in mixed solution C; The temperature of described crosslinking reaction is 50～70 ℃, and the time of crosslinking reaction is 1～3h; Described chitosan crosslinked dose is glutaraldehyde, presses mass ratio, chitosan: chitosan crosslinked dose is 1: 0.2～0.4.
9. the preparation method of a kind of degradable biological hydrogel as claimed in claim 4 is characterized in that in step 5), and the power of described ultraviolet lamp is 500～1500W, and the time of described irradiation is 20～60min.
10. the preparation method of a kind of degradable biological hydrogel as claimed in claim 4 is characterized in that in step 6), and described being soaked in water is with distilled water immersion 3～7 days, during change water to remove pore-creating agent at interval.
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| CN103044588A (en) * | 2012-12-26 | 2013-04-17 | 杭州飞捷科技有限公司 | Solid hydrogel and preparation method thereof |
| CN103044588B (en) * | 2012-12-26 | 2016-07-06 | 杭州飞捷科技有限公司 | A kind of solid hydrogel and preparation method thereof |
| CN103623797A (en) * | 2013-12-16 | 2014-03-12 | 武汉纺织大学 | Preparation method of natural polyelectrolyte gel adsorbent for wastewater treatment |
| CN106215952A (en) * | 2016-07-15 | 2016-12-14 | 湖北科技学院 | Quantum dot/TiO2the soft reactor of Nanometer composite hydrogel and in situ radiation preparation method |
| CN108467464A (en) * | 2018-04-02 | 2018-08-31 | 常熟理工学院 | Hydrogel of visible-light curing containing azelaic acid and preparation method thereof |
| CN108815567A (en) * | 2018-06-05 | 2018-11-16 | 东莞市联洲知识产权运营管理有限公司 | A kind of preparation method of antiseptic dressing aquagel |
| CN112370567A (en) * | 2020-11-19 | 2021-02-19 | 南方医科大学南方医院 | Hydrogel active dressing with antibacterial and anti-inflammatory functions |
| CN112370567B (en) * | 2020-11-19 | 2023-05-16 | 南方医科大学南方医院 | Hydrogel active dressing with antibacterial and anti-inflammatory functions |
| CN114939192A (en) * | 2022-07-01 | 2022-08-26 | 郑州大学第一附属医院 | Hydrogel for scleral nail and preparation method and application thereof |
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