CN105327388A - Medical adhesives and preparation method thereof - Google Patents
Medical adhesives and preparation method thereof Download PDFInfo
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- CN105327388A CN105327388A CN201510891554.XA CN201510891554A CN105327388A CN 105327388 A CN105327388 A CN 105327388A CN 201510891554 A CN201510891554 A CN 201510891554A CN 105327388 A CN105327388 A CN 105327388A
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Abstract
The invention relates to medical adhesives and a preparation method thereof. The adhesives are prepared from aldehyde sodium alginate and amination carboxymethyl chitosan. The preparation method includes the steps of mixing equal volumes of aldehyde sodium alginate solution with concentration of 10-50 wt% and amination carboxymethyl chitosan solution with concentration of 1-6 wt%, conducting a Schiff base reaction to form hydrogel, and obtaining the medical adhesives. Selected aldehyde sodium alginate and amination carboxymethyl chitosan are both natural biological materials, are free of toxin and odor, quite high in biological compatibility, low in price, safe, reliable, capable of being locally sprayed or injected to any part of a body in situ and low in cost, and is ideal substitute goods for fibrin glue sold on the market. The preparation method is simple.
Description
Technical field
The invention belongs to chemical modification and medical field, particularly a kind of adhesive of medical and preparation method thereof.
Background technology
According to statistics, the patient wound more than 1,200 ten thousand is had to need to be treated every year.In trauma operation, traditional method uses mechanical connection thing (as: stitching thread, nail etc.) exactly.But they inherently can cause damage to surrounding tissue, be not suitable for complicated operation.In view of these are not enough, the appearance of adhesive of medical adhesive, gets the attention with the advantage of its uniqueness.Compared with stitching thread, binding agent can effectively stop blooding, easy to use, reduce operating time, the secondary injury etc. of avoiding stitching thread to bring without the need to taking out stitches.In recent years, along with developing rapidly of modern medicine, and the inclination of policy, the medical material of encouraging large-scale hygienic material company development of new is done one's utmost by government of developed country.In this context, biological adhesive field develops rapidly, opens the situation of various product wide variety, function uniqueness gradually.
Desirable medical adhesive should have following requirement:
1, avirulence, without carcinogenic, without teratogenesis and mutagenesis.
2, good biocompatibility is had.
3, aseptic and can be antibacterial.
4, can use under the wet environment having blood and tissue fluid.
5, quick-binding can be realized under normal temperature and pressure.
6, well, stick portion has certain elasticity and toughness for bonding strength and bonding persistency.
7, biodegradable.
Along with the raising of people's living standard, to medical procedure painless, without scar, operation simple type require more and more higher.Commercialization adhesive of medical main is at present the large class binding agent of a-cyanoacrylate class and fibrin two.But a-cyanoacrylate class binding agent due to bonding position really up to the mark, the elasticity of organ surface tension force is inadequate, can produce formaldehyde thus cause the shortcomings such as inflammatory reaction after solidification, be not suitable in body carry out organizing bonding; Fibrin sealant is a kind of commercialization and the binding agent applied clinically, but the constituent fibrin of fibrin and thrombin extract from human blood, and the danger that thoughts catch an illness poison, easily brings quadratic risk function to patient.Therefore, research and preparation goes out to meet above-mentioned requirements, can the adhesive of medical of in-situ injection be the direction that this area research persons make great efforts always.The people such as Weng have prepared oxidation open loop glucosan, and being then mixed to get with carboxymethyl chitosan can the in-situ crosslinking aquogel of rapid shaping.Rheological experiment proves that this hydrogel can reach gel point at about 80s.After observing lyophilization, obtained freeze-drying support shows, this hydrogel inside is large aperture structure.Further mouse skin experiment proves that this rapid shaping hydrogel is conducive to accelerating new skin histology and is formed, and then promotes trauma skin reparation.[Weng, L., Romanov, A., Rooney, J., etal.Non-cytotoxic, insitugelablehydrogelscomposedofN-carboxyethylchitosanan doxidizeddextran.Biomaterials:2008.29 (29): 3905-3913.] Tan etc. has prepared the hyaluronic acid of oxidation open loop, utilizes the amino on it above aldehyde radical and chitosan molecule chain to be obtained by reacting Quick cross-linking injection aquagel.Experimental result shows, when DHA and chitosan mass ratio are 5:5, hydrogel can plastic in two minutes.Degradation experiment shows that this composite aquogel can reach the degradation property that can regulate and control by change oxidation hyalomitome calculation and chitosan ratio.Chondrocytes in vitro culture experiment proves that this aquogel system can support that chondrocyte well grows therein.[Tan,H.,Chu,C.R.,Payne,K.A.,etal.Injectableinsituformingbiodegradablechitosan–hyaluronicacidbasedhydrogelsforcartilagetissueengineering.Biomaterials:2009.30(13):2499-2506.]
Natural polymer is the macromolecular polymer generated in nature animal and plant body, is a kind of reproducible resource.There is good biocompatibility, non-stimulated, catabolite is nontoxic and can be absorbed by the body, be widely used in the various fields of biomaterial.Sodium alginate (sodiumalginate) is a kind of polysaccharide being applied to bio-medical field by FDA approval.Similar is in glycosaminoglycans, and after implanting, simplified reaction is little, can stop blooding, antibacterial and be widely used in organizational project and association area to the healing of wound, is the ideal material preparing binding agent.Carboxymethyl chitosan (Carboxymethylchitosan) is a kind of water-solubility chitosan derivative, has numerous characteristics, and as antibiotic property is strong, having preservation, is the good polyampholyte of a kind of biocompatibility.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of adhesive of medical and preparation method thereof, selects sodium alginate and carboxymethyl chitosan, good biocompatibility in the composition of this binding agent, can be absorbed degraded by organism.This preparation method is simple, with low cost.
A kind of adhesive of medical of the present invention, raw material comprises: aldehyde radical sodium alginate and amination carboxymethyl chitosan; Wherein, the mass ratio of aldehyde radical sodium alginate and amination carboxymethyl chitosan is 5.00 ~ 8.33:1.
The preparation method of a kind of adhesive of medical of the present invention, comprise: be that the amination carboxymethyl chitosan solution of the aldehyde radical sodium alginate soln and 1% ~ 6% (w/v) of 10% ~ 50% (w/v) mixes by isopyknic concentration, schiff base reaction forms hydrogel, namely obtains adhesive of medical.
The preparation method of described aldehyde radical sodium alginate comprises: under room temperature lucifuge condition, join in the aqueous solution of sodium alginate by sodium metaperiodate aqueous solution, and reaction 4 ~ 6h, dialysis, lyophilization, obtains aldehyde radical sodium alginate.
Described sodium alginate is the medium viscosity 580mpa.s sodium alginate bought, and G block ratio is 40%.(molecular weight is for being about 1,440,000)
The molar ratio of described sodium metaperiodate and sodium alginate is 0.88 ~ 1.5:1.
The preparation method of described amination carboxymethyl chitosan comprises: joined by ethylenediamine in carboxymethyl chitosan sugar aqueous solution, regulates pH to 5.0, adds water-soluble carbodiimide EDC, and 37 DEG C of reaction 4 ~ 6h, dialysis, lyophilization, obtains amination carboxymethyl chitosan.
Described carboxymethyl chitosan deacetylation is 82%, and molecular weight is about 2,000,000.
The mol ratio of described carboxymethyl chitosan and ethylenediamine is 1:1; Carboxymethyl chitosan and water-soluble carbodiimide mol ratio are 1:2.
The time of described dialysis is 2 ~ 3 days; Lyophilization is first at-80 DEG C of freezing 6h, then puts into vacuum freeze drier and carries out lyophilizing.
The Corii Sus domestica adhesive strength of described hydrogel is 10 ~ 30gfcm
-2, gel time 20-130 second.
In the present invention, aldehyde radical sodium alginate soln and aminated carboxymethyl chitosan solution are expelled to mixing in same syringe needle by two syringes simultaneously to make it schiff base reaction occurs, at room temperature spontaneously be cross-linked to form gel, be expelled to and need bonding tissue site, and by tissue adhesion together.
The present invention selects sodium metaperiodate as the oxidant of sodium alginate, due to sodium alginate be by D-D-mannuronic acid (M unit) unit and Q-L-guluronic acid (G unit) unit in proportion order bonding form, its uronic acid unit has cis vicinal diamines structure, therefore under the Oxidation of sodium metaperiodate, opens C-C key and generates two aldehyde radicals.Because there is the aldehyde functions of effective quantity, can with containing the spontaneous generation schiff base reaction of amino material.Have and organize characteristic that is bonding and sterilization.
Containing carboxyl (-COOH) and amino (-NH on carboxymethyl chitosan strand
2), for improving the amino content of carboxymethyl chitosan.Under the effect of crosslinked EDC, modification is carried out to the carboxyl on carboxymethyl chitosan with ethylenediamine, consume carboxyl, more amino in the grafting of carboxymethyl chitosan strand, make itself and aldehyde radical sodium alginate react the speed forming gel faster.
Preparation method of the present invention is very convenient, two kinds of polymer solutions can form gel rapidly when mixing, there is certain adhesive capacity and adhesion strength, and gel time shortens greatly, act on any position of health by simple localized pulverization or injection, be expected to the substitute products as commercially available Fibrin Glue.
The object of the invention is to prepare aldehyde radical sodium alginate and aminated carboxymethyl chitosan, and develop this bi-component hydrogel and use as adhesive of medical.Selected sodium alginate and carboxymethyl chitosan, good biocompatibility, can be absorbed degraded by organism.Form hydrogel by the amino generation schiff base reaction in the aldehyde radical in aldehyde radical sodium alginate and amination carboxymethyl chitosan and be used as binding agent.
The bio-medical binding agent of a kind of aldehyde radical sodium alginate provided by the invention and amination carboxymethyl chitosan, for raw material with sodium alginate and carboxymethyl chitosan, be that the aldehyde radical sodium alginate soln of 30% ~ 50% mixes with the amination carboxymethyl chitosan solution of 6% according to isopyknic concentration, form hydrogel through schiff base reaction and can be used as adhesive of medical and use.By the aldehyde radical of sodium periodate oxidation process implementation sodium alginate, then with the amination carboxymethyl chitosan of ethylenediamine modification be mixed to form hydrogel.
beneficial effect
Sodium alginate selected in the present invention and carboxymethyl chitosan are all natural biologic materials, nontoxic, tasteless, have good biocompatibility, cheap, safe and reliable.At room temperature, aldehyde radical sodium alginate and amination carboxymethyl chitosan generation schiff base reaction, form gel rapidly and have adhesion, acting on any position of health by localized pulverization or in-situ injection, with low cost, be the ideal substitute of commercially available Fibrin Glue; Preparation method is simple to operate.
Detailed description of the invention
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.In addition should be understood that those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims limited range equally after the content of having read the present invention's instruction.
Embodiment 1
Accurately take 3.96g sodium alginate to be dissolved in 400ml deionized water and to form homogeneous solution.4.28g sodium metaperiodate lucifuge is dissolved in appropriate deionized water, then sodium periodate solution lucifuge is dropwise added in homogeneous sodium alginate soln, and lucifuge reacts 4h under room temperature.Loaded by product in bag filter (molecular cut off is 14000) and dialyse 3 days, every 4h changes time water.
Product to be poured in plate into pre-freeze 6h in-80 DEG C of refrigerators, put into freeze dryer subsequently, lyophilization obtains aldehyde radical sodium alginate.
Embodiment 2
Accurately taking 5g pig gelatin is dissolved in the aqueous solution of 100ml, adds 16ml ethylenediamine, and adjust PH to 5.0, add 0.66g water-soluble carbodiimide EDC, 37 DEG C of reactions are spent the night.To be cooled to room temperature, product is loaded bag filter (molecular cut off is 3500) dialysis 3 days, every 4h changes time water.Pour product into plate and in-80 DEG C of refrigerators pre-freeze 6h, put into freeze dryer subsequently, obtain amination carboxymethyl chitosan.
Embodiment 3
Aldehyde radical alginic acid is made into the solution that concentration is 30%.Precise amination carboxymethyl chitosan, being made into concentration with deionized water is 6% solution.The aminated carboxymethyl chitosan solution of 1ml is got with the needle tubing of 2ml, 1ml aldehyde radical sodium alginate soln is got with 2ml needle tubing, connect through a Y type, by aminated carboxymethyl chitosan solution and aldehyde radical sodium alginate soln simultaneously by a needle injection on the Corii Sus domestica of two panels 1cm × 3cm, two panels skin is binded, and adhesive strength is 10gfcm
-2, gel time 130 seconds.
Embodiment 4
Aldehyde radical alginic acid is made into the solution that concentration is 50%.Precise amination carboxymethyl chitosan, being made into concentration with deionized water is 6% solution.The aminated carboxymethyl chitosan solution of 1ml is got with the needle tubing of 2ml, 1ml aldehyde radical sodium alginate soln is got with 2ml needle tubing, connect through a Y type, by aminated carboxymethyl chitosan solution and aldehyde radical sodium alginate soln simultaneously by a needle injection on the Corii Sus domestica of two panels 1cm × 3cm, two panels skin is binded, and adhesive strength is 30gfcm
-2, gel time 20 seconds.
Claims (10)
1. an adhesive of medical, raw material comprises: aldehyde radical sodium alginate and amination carboxymethyl chitosan; Wherein, the mass ratio of aldehyde radical sodium alginate and amination carboxymethyl chitosan is 5.00 ~ 8.33:1.
2. the preparation method of an adhesive of medical, comprise: be that the aldehyde radical sodium alginate soln of 10% ~ 50%w/v mixes with the amination carboxymethyl chitosan solution of 1% ~ 6%w/v by isopyknic concentration, schiff base reaction forms hydrogel, namely obtains adhesive of medical.
3. the preparation method of a kind of adhesive of medical according to claim 2, it is characterized in that, the preparation method of described aldehyde radical sodium alginate comprises: under room temperature lucifuge condition, sodium metaperiodate aqueous solution is joined in the aqueous solution of sodium alginate, reaction 4 ~ 6h, dialysis, lyophilization, obtains aldehyde radical sodium alginate.
4. the preparation method of a kind of adhesive of medical according to claim 3, is characterized in that, described sodium alginate is medium viscosity 580mpa.s sodium alginate, and it is 40% that molecular weight is about 1,440,000, G block ratio.
5. the preparation method of a kind of adhesive of medical according to claim 3, is characterized in that, the molar ratio of described sodium metaperiodate and sodium alginate is 0.88 ~ 1.5:1.
6. the preparation method of a kind of adhesive of medical according to claim 2, it is characterized in that, the preparation method of described amination carboxymethyl chitosan comprises: joined by ethylenediamine in carboxymethyl chitosan sugar aqueous solution, regulate pH to 5.0, add water-soluble carbodiimide EDC, 37 DEG C of reaction 4 ~ 6h, dialysis, lyophilization, obtains amination carboxymethyl chitosan.
7. the preparation method of a kind of adhesive of medical according to claim 6, is characterized in that, described carboxymethyl chitosan deacetylation is 82%, and molecular weight is about 2,000,000.
8. the preparation method of a kind of adhesive of medical according to claim 6, is characterized in that, the mol ratio of described carboxymethyl chitosan and ethylenediamine is 1:1; Carboxymethyl chitosan and water-soluble carbodiimide mol ratio are 1:2.
9. the preparation method of a kind of adhesive of medical according to claim 3 or 6, is characterized in that, the time of described dialysis is 2 ~ 3 days; Lyophilization is first at-80 DEG C of freezing 6h, then puts into vacuum freeze drier and carries out lyophilizing.
10. the preparation method of a kind of adhesive of medical according to claim 2, is characterized in that, the Corii Sus domestica adhesive strength of described hydrogel is 10 ~ 30gfcm
-2, gel time 20-130 second.
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| CN106075553A (en) * | 2016-07-12 | 2016-11-09 | 四川大学 | A kind of bio-medical binding agent and preparation method thereof |
| CN106975097A (en) * | 2017-03-02 | 2017-07-25 | 四川大学 | A kind of bio-medical bonding hydrogel and preparation method thereof |
| CN107050510A (en) * | 2017-06-14 | 2017-08-18 | 东华大学 | A kind of sodium alginate/glutin injectable double-network hydrogel and its preparation and application |
| CN107496974A (en) * | 2017-10-10 | 2017-12-22 | 东华大学 | A kind of two-component adhesive of medical based on glucan and chitosan and preparation method thereof |
| CN107880532A (en) * | 2017-11-23 | 2018-04-06 | 马鞍山菌菌食品科技有限公司 | A kind of sodium alginate cross-linking dendritic macromole/aqueous polyurethane preservative film and preparation method thereof |
| CN108187131A (en) * | 2017-12-29 | 2018-06-22 | 孙祎 | A kind of preparation method of medical antibacterial bearing hydrocolloid dressing |
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| CN106975097A (en) * | 2017-03-02 | 2017-07-25 | 四川大学 | A kind of bio-medical bonding hydrogel and preparation method thereof |
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| CN108187131A (en) * | 2017-12-29 | 2018-06-22 | 孙祎 | A kind of preparation method of medical antibacterial bearing hydrocolloid dressing |
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| CN112807478A (en) * | 2018-08-20 | 2021-05-18 | 稳得希林(杭州)生物科技有限公司 | Polysaccharide-based tissue adhesive medical adhesive and application thereof |
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| CN109847093B (en) * | 2019-02-23 | 2021-10-01 | 兰州大学第一医院 | Antibacterial orthopedic adhesive and preparation method thereof |
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| CN111662464B (en) * | 2020-07-23 | 2022-01-25 | 南京工业大学 | Preparation method of chitosan/sodium alginate double-network hydrogel |
| CN113577371A (en) * | 2021-07-28 | 2021-11-02 | 华东理工大学 | Organic-inorganic hybrid hydrogel bone adhesive and preparation method thereof |
| CN113952499A (en) * | 2021-09-27 | 2022-01-21 | 中国科学院宁波材料技术与工程研究所 | Natural polysaccharide sponge and preparation method and application thereof |
| CN113941026A (en) * | 2021-10-25 | 2022-01-18 | 浙江中医药大学 | Bioactive glass-coated chitosan cellulose derivative-based injectable hydrogel dressing and preparation method thereof |
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| CN114957720A (en) * | 2022-05-30 | 2022-08-30 | 大连理工大学 | Self-crosslinking antioxidant PCA-g-CMCS/OSA Schiff base hydrogel and preparation method thereof |
| CN115177779A (en) * | 2022-06-14 | 2022-10-14 | 深圳凡旻生物科技有限公司 | Biological glue and preparation method and application thereof |
| CN115177779B (en) * | 2022-06-14 | 2023-12-05 | 深圳凡旻生物科技有限公司 | Biological glue and preparation method and application thereof |
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