CN102617880A - End-point fixing preparation method for multi-aldehyde alginic acid coating - Google Patents
End-point fixing preparation method for multi-aldehyde alginic acid coating Download PDFInfo
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- CN102617880A CN102617880A CN2012101096271A CN201210109627A CN102617880A CN 102617880 A CN102617880 A CN 102617880A CN 2012101096271 A CN2012101096271 A CN 2012101096271A CN 201210109627 A CN201210109627 A CN 201210109627A CN 102617880 A CN102617880 A CN 102617880A
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Abstract
The invention discloses an end-point fixing preparation method for a multi-aldehyde alginic acid coating. The method comprises the following steps: firstly, polymer material is soaked into sulfuric acid solution of potassium permanganate for acidizing treatment; then the material subjected to acidizing treatment is placed into polyethylene imine solution so as to obtain an amination decorated surface after reaction; periodic acid or sodium periodate is used for oxidation treatment to sodium alginate, aldehyde group is exposed at the tail end of the segment of alginic acid, and multi-aldehyde sodium alginate is obtained; the liquid reactant of the multi-aldehyde sodium alginate is prepared, the material on the amination decorated surface is placed into the liquid reactant, and the multi-aldehyde alginic acid coating is obtained through an end-point fixing method. The preparation method provided by the invention overcomes the defects of bad biocompatibility, poor anticoagulant activity, potential toxicity and the like in common polymer material.
Description
Technical field
The present invention relates to polymer surface coating technology field, more particularly, relate to a kind of preparation method who utilizes the polysaccharide molecule fragment polymer surface coating to be carried out modification.
Background technology
Biomedical material is used and is faced biocompatibility and blood compatibility two large problems.Coating technology is passed through the preparatory modification to material surface, thereby has improved biomedical material surfaces for biocompatibility and anticoagulating active.Heparin belongs to mucopolysaccharide; Molecular weight 5000-40000; Be the mixtinite that is made up of electronegative linear polysaccharide, the most important character of heparin is its anticoagulation characteristic, and the anticoagulating active of heparin comes from it and can interact with the intravital multiple coagulation inhibitor of biology; Reach anticoagulant purpose through the anticoagulating active that quickens or improve these supressors, but be stained with defective for arrestin.Wherein heparin is most important to the effect of Thrombin inhibitor (AT-III).Biomedical material surface heparin fixation principle can reduce physics method and chemical method at present.The physics method is promptly through winding between mechanical embedding, the molecular chain and infiltration, be fixed to biomaterial surface by modes such as porose material absorption with heparin, thereby reaches the immobilized purpose of heparin.Chemical method is promptly through reactive functional group abundant on the heparin molecule chain, but reacts like corresponding reactive group on sulfonic group, amino, carboxyl etc. and the target material surface, with ionic linkage or with the mode of covalent linkage it is fixed to biomaterial surface.
Summary of the invention
The objective of the invention is to overcome the deficiency of prior art; Shortcomings such as the common high molecular materials biocompatibility is poor, anticoagulating active is poor in order to overcome, genotoxic potential; Utilize periodate oxidation and terminal point technique for fixing, a kind of preparation method of many aldehyde radicals sodium-alginate coating is provided.
The object of the invention is achieved through following technical proposals:
A kind of preparation method of many aldehyde radicals sodium-alginate coating, carry out according to following step:
At first, promptly step (1) is immersed in macromolecular material in the sulphuric acid soln of potassium permanganate, carries out acidification, wherein:
Said macromolecular material can be selected Vilaterm, SE, Vestolen PP 7052, polyester, Zylox, nylon, polycarbonate or the tetrafluoroethylene of medical grade; These materials can be used for the structure of extracorporeal circulation of blood pipeline, need carry out modification to improve the consistency of itself and blood to its surface.
The sulphuric acid soln of said potassium permanganate is adopted and utilized following mode to prepare: elder generation is dissolved in potassium permanganate in the deionized water and mixes; Slowly be reached for 10%-70% to the vitriolic mass percent and get final product then to wherein adding the vitriol oil (mass percent is the vitriol oil of 95-98%), mixing.
Macromolecular material being immersed in the sulphuric acid soln of potassium permanganate, carrying out acidification, mainly is for material modified surface properties, and can select the s.t. time is 1min-10min, and normal temperature is handled, and temperature is 20-25 ℃; The intensity that in the acidification process, can adopt the mechanical perhaps mode of ultrasonic agitation to strengthen reacting can use deionized water that material is cleaned after acidification.
Step (2) places polymine (PEI) solution with the material of acidified processing, and reaction is to obtain the surface that amination is modified, wherein:
The mass percentage concentration of said polymine (PEI) solution is 0.005%-0.5%, and the reaction times is 10min-60min, and normal temperature is handled, and temperature is 20-25 ℃.
Step (3) uses Periodic acid 99 or sodium periodate oxidation to handle sodium-alginate, makes to obtain many aldehyde radicals sodium-alginate by Lalgine fragment ends exposed aldehyde radical, wherein:
The mol ratio of the repeating unit of Periodic acid 99 or sodium periodate and sodium-alginate is (1-3): 10, and oxidizing reaction stirring reaction at least 24 hours under the lucifuge condition, preferred 24-40 hour; Adopt the terepthaloyl moietie termination reaction, the 96wt% alcoholic acid aqueous solution precipitates, post precipitation suction filtration, dialysis, and-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.
Step (4) disposes the reaction solution (aqueous solution) of many aldehyde radicals sodium-alginate, and the material of amination modification of surfaces is placed reaction solution, obtains the coating of many aldehyde radicals sodium-alginate through the terminal point fixation method, wherein:
The reaction solution of said many aldehyde radicals sodium-alginate is the aqueous solution, many aldehyde radicals sodium-alginate 0.05-2mg/mL wherein, NaCl0.15-0.55mol/L, sodium cyanoborohydride 0.01-0.1mg/mL; Temperature of reaction is 30 ℃-60 ℃, preferred 40-50 ℃; At least 2 hours reaction times, preferred 2-6 hour.
Technical scheme provided by the present invention adopts the fixing many aldehyde radicals Lalgine coating of terminal point; Form by polymine, many aldehyde radicals sodium-alginate; It is low that native toxicity is low, cost is enriched in the source, but standing storage at room temperature, and sodium-alginate group is fixed on the surface of material in the coating; Increase the area contact with blood and or chance, effectively bring into play the character of sodium-alginate.Periodic acid oxidation is gentle, good reproducibility; The terminal point fixation method is implemented convenient, and many aldehyde radicals of terminal point fixed sodium-alginate combines firmly, and space conformation is good, can effectively increase the biocompatibility and the anticoagulating active of polymer surface.In field of biomedical materials, have broad application prospects and higher utility like extracorporeal circulation pipeline, artery filter, venous incubation etc., can effectively reduce medical treatment cost, alleviate patient's economical load.
Description of drawings
The preparation principle synoptic diagram of many aldehyde radicals of Fig. 1 sodium-alginate.
Fig. 2 preparing method's of the present invention synoptic diagram, wherein OSA represents sodium-alginate.
The infrared spectrogram of the PVC of Fig. 3 SE (PVC) and band PEI coating, wherein a is undressed PVC, b is the PVC of band PEI coating.
Fig. 4 SE (PVC) and have the infrared spectrogram of the PVC of many aldehyde radicals sodium-alginate coating, wherein a is undressed PVC, b is the PVC that has many aldehyde radicals sodium-alginate coating.
Embodiment
Further specify technical scheme of the present invention below in conjunction with specific embodiment.The extracorporeal circulation pipeline that the macromolecular material that uses provides as Dongguan Kewei Medical Instrument Co., Ltd, material are SE.
Embodiment 1
The first step is dissolved in 0.344 gram potassium permanganate in 162 ml deionized water, slowly adds 95wt% vitriol oil 10ml, and the vitriol oil and potassium permanganate are mixed very much.
In second step, the middle macromolecular material PVC that adds in step 1 gained solution stirs fully reaction 10min.
In the 3rd step, pressed sodium periodate and sodium-alginate unit mol ratio 1: 10, the oxide treatment Lalgine; Make Lalgine fragment ends exposed aldehyde radical, terepthaloyl moietie termination reaction, 96wt% aqueous ethanolic solution deposition; Post precipitation suction filtration, dialysis ,-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.Oxidizing reaction stirring reaction 24 hours under the lucifuge condition.
The 4th step, immerse in the 0.01wt% polyethyleneimine: amine aqueous solution through the pretreated macromolecular material of step 2,20 ℃ of reactions of normal temperature 60min obtains the surface that amination is modified.
The 5th step; Many aldehyde radicals of step 3 gained sodium-alginate preparation reaction solution (aqueous solution), many aldehyde radicals Lalgine concentration 0.1mg/ml wherein, NaCl 0.15mol/L; Sodium cyanoborohydride 0.1mg/ml; The macromolecular material that the amination of step 4 gained is modified places many aldehyde radicals Lalgine reaction solution, 40 ℃ of temperature of reaction, 2 hours reaction times.
The PVC of undressed PVC, band PEI coating, the PVC that has many aldehyde radicals sodium-alginate coating are carried out examination of infrared spectrum (ir spectra manufacturer and model Thermo NICOLET 6700, detector are that DTGs KBr, beam splitter are that KBr, wavelength region are 650-4000nm); Can know 1550cm from shown in accompanying drawing 3 and 4
-1The place is NH
2Charateristic avsorption band, 3400cm
-1About the charateristic avsorption band of visible sodium-alginate, explain that many aldehyde radicals sodium-alginate passes through NH
2Be fixed on the surface of material.
Embodiment 2
The first step is dissolved in 0.328 gram potassium permanganate in 144 ml deionized water, slowly adds 95% vitriol oil 20ml, and the vitriol oil and potassium permanganate are mixed very much.
Second step added macromolecular material in step 1 gained solution, stir fully reaction 1min.
In the 3rd step, pressed sodium periodate and sodium-alginate unit mol ratio 3: 10, the oxide treatment Lalgine; Make Lalgine fragment ends exposed aldehyde radical, terepthaloyl moietie termination reaction, 96% ethanol sedimentation; Post precipitation suction filtration, dialysis ,-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.Oxidizing reaction stirring reaction 40 hours under the lucifuge condition.
The 4th step, immerse in the 0.5% polyethyleneimine: amine aqueous solution through the pretreated macromolecular material of step 2,25 ℃ of reactions of normal temperature 10min obtains the surface that amination is modified.
The 5th step; Many aldehyde radicals of step 3 gained sodium-alginate preparation reaction solution (aqueous solution), many aldehyde radicals Lalgine concentration 2mg/ml wherein, NaCl 0.15mol/L; Sodium cyanoborohydride 0.1mg/ml; The macromolecular material that the amination of step 4 gained is modified places many aldehyde radicals Lalgine reaction solution, 50 ℃ of temperature of reaction, 6 hours reaction times.
Embodiment 3
The first step is dissolved in 0.328 gram potassium permanganate in 144 ml deionized water, slowly adds 95% vitriol oil 20ml, and the vitriol oil and potassium permanganate are mixed very much.
Second step added macromolecular material in step 1 gained solution, stir fully reaction 8min.
In the 3rd step, pressed sodium periodate and sodium-alginate unit mol ratio 1: 10, the oxide treatment Lalgine; Make Lalgine fragment ends exposed aldehyde radical, terepthaloyl moietie termination reaction, 96% ethanol sedimentation; Post precipitation suction filtration, dialysis ,-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.Oxidizing reaction stirring reaction 30 hours under the lucifuge condition.
The 4th step, immerse in the 0.05% polyethyleneimine: amine aqueous solution through the pretreated macromolecular material of step 2,25 ℃ of reactions of normal temperature 30min obtains the surface that amination is modified.
The 5th step; Many aldehyde radicals of step 3 gained sodium-alginate preparation reaction solution (aqueous solution), many aldehyde radicals Lalgine concentration 0.05mg/ml wherein, NaCl 0.35mol/L; Sodium cyanoborohydride 0.01mg/ml; The macromolecular material that the amination of step 4 gained is modified places many aldehyde radicals Lalgine reaction solution, 60 ℃ of temperature of reaction, 4 hours reaction times.
Embodiment 4
The first step is dissolved in 0.328 gram potassium permanganate in 144 ml deionized water, slowly adds 95% vitriol oil 20ml, and the vitriol oil and potassium permanganate are mixed very much.
Second step added macromolecular material in step 1 gained solution, stir fully reaction 5min.
In the 3rd step, pressed sodium periodate and sodium-alginate unit mol ratio 2: 10, the oxide treatment Lalgine; Make Lalgine fragment ends exposed aldehyde radical, terepthaloyl moietie termination reaction, 96% ethanol sedimentation; Post precipitation suction filtration, dialysis ,-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.Oxidizing reaction stirring reaction 35 hours under the lucifuge condition.
The 4th step, immerse in the 0.005% polyethyleneimine: amine aqueous solution through the pretreated macromolecular material of step 2,25 ℃ of reactions of normal temperature 50min obtains the surface that amination is modified.
The 5th step; Many aldehyde radicals of step 3 gained sodium-alginate preparation reaction solution (aqueous solution), many aldehyde radicals Lalgine concentration 0.5mg/ml wherein, NaCl 0.25mol/L; Sodium cyanoborohydride 0.05mg/ml; The macromolecular material that the amination of step 4 gained is modified places many aldehyde radicals Lalgine reaction solution, 30 ℃ of temperature of reaction, 4 hours reaction times.
Embodiment 5
The first step is dissolved in 0.328 gram potassium permanganate in 144 ml deionized water, slowly adds 95% vitriol oil 20ml, and the vitriol oil and potassium permanganate are mixed very much.
Second step added macromolecular material in step 1 gained solution, stir fully reaction 5min.
In the 3rd step, pressed sodium periodate and sodium-alginate unit mol ratio 2: 10, the oxide treatment Lalgine; Make Lalgine fragment ends exposed aldehyde radical, terepthaloyl moietie termination reaction, 96% ethanol sedimentation; Post precipitation suction filtration, dialysis ,-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.Oxidizing reaction stirring reaction 35 hours under the lucifuge condition.
The 4th step, immerse in the 0.005% polyethyleneimine: amine aqueous solution through the pretreated macromolecular material of step 2,25 ℃ of reactions of normal temperature 50min obtains the surface that amination is modified.
The 5th step; Many aldehyde radicals of step 3 gained sodium-alginate preparation reaction solution (aqueous solution), many aldehyde radicals Lalgine concentration 1mg/ml wherein, NaCl 0.25mol/L; Sodium cyanoborohydride 0.05mg/ml; The macromolecular material that the amination of step 4 gained is modified places many aldehyde radicals Lalgine reaction solution, 30 ℃ of temperature of reaction, 4 hours reaction times.
Utilize the phenolsulfuric acid method, change, obtain the fixed amount of OSA indirectly through sodium-alginate (OSA) reaction solution absorbance before and after calculating reaction; Prove fixing (the Dubois M really of OSA simultaneously; Gilles K A, Hamilton JK, et al.Colorimetric method for determination of sugars and related substances [J] .AnalyticalChemistry; 1956,28 (3): 350-356).
| Abs before the reaction | Reaction back Abs | Fixed amount ug/cm 2 | |
| Embodiment 1 | 0.394 | 0.338 | 0.79 |
| Embodiment 2b | 0.235 | 0.224 | 7.78 |
| Embodiment 3 | 0.153 | 0.127 | 0.49 |
| Embodiment 4a | 0.292 | 0.266 | 3.62 |
| Embodiment 5b | 0.126 | 0.109 | 5.03 |
50 times of 10 times of b:OSA test fluid dilutions of a:OSA test fluid dilution
There is the macromolecular material PVC of sodium-alginate to experimentize to coating; After respectively the sample of embodiment 1-5 being carried out the test of four of coagulation functions and arrestin absorption; Take the mean, adopt 5 groups of identical PVC to carry out identical test as contrast after, take the mean; The test of four of coagulation functions STA-R
blood coagulation analyzer automatically that adopts Diagnostica Stago wherein; Protein adsorption adopts BCA method (Ishihara K; Fukumoto K; Iwasaki Y; Nakabayashi N.Modification of polysulfone with phospholipid polymer for improvement of the blood compatibility.Part 1.Surface characterization.Biomaterials 1999,20 (17): 1545-1551)
Arrestin absorption (having improved biocompatibility)
| Types of coatings | HAS adsorbs (ug/cm 2) | HPF adsorbs (ug/cm 2) |
| Control group | 270.7 | 544.3 |
| The OSA single coating | 145.6 | 221.8 |
* adhesion protein adopts the BCA standard measure
* HAS: human serum albumin HPF: human fibrinogen
Can find out that from above-mentioned experiment the macromolecular material of process sodium-alginate OSA single coating is compared with control group in four of coagulation functions of test, protein adsorption performance, obviously anticoagulant and protein adsorption are effectively improved biocompatibility and coagulation function.
More than the present invention has been done exemplary description; Should be noted that; Under the situation that does not break away from core of the present invention, the replacement that is equal to that any simple distortion, modification or other those skilled in the art can not spend creative work all falls into protection scope of the present invention.
Claims (5)
1. the preparation method of the coating of aldehyde radical sodium-alginate more than a kind is characterized in that, carries out according to following step:
Step (1) is immersed in macromolecular material in the sulphuric acid soln of potassium permanganate, carries out acidification
Step (2) places the polyethyleneimine: amine aqueous solution with the material of acidified processing, and reaction is to obtain the surface that amination is modified
Step (3) uses Periodic acid 99 or sodium periodate oxidation to handle sodium-alginate, makes to obtain many aldehyde radicals sodium-alginate by Lalgine fragment ends exposed aldehyde radical
Step (4) disposes the reaction solution of many aldehyde radicals sodium-alginate, and the material of amination modification of surfaces is placed reaction solution, obtains the coating of many aldehyde radicals sodium-alginate through the terminal point fixation method.
2. the preparation method of a kind of many aldehyde radicals sodium-alginate coating according to claim 1; It is characterized in that; In the said step (1), said macromolecular material can be selected Vilaterm, SE, Vestolen PP 7052, polyester, Zylox, nylon, polycarbonate or the tetrafluoroethylene of medical grade; The sulphuric acid soln of said potassium permanganate is adopted and utilized following mode to prepare: elder generation is dissolved in potassium permanganate in the deionized water and mixes; Slowly be reached for 10%-70% to the vitriolic mass percent and get final product then to wherein adding the vitriol oil that mass percent is 95-98%, mixing; The time of carrying out acidification is 1min-10min, and temperature is 20-25 ℃, the intensity that in the acidification process, can adopt the mechanical perhaps mode of ultrasonic agitation to strengthen reacting.
3. the preparation method of a kind of many aldehyde radicals sodium-alginate coating according to claim 1; It is characterized in that in the said step (2), the mass percentage concentration of said polyethyleneimine: amine aqueous solution is 0.005%-0.5%; Reaction times is 10min-60min, and temperature is 20-25 ℃.
4. the preparation method of a kind of many aldehyde radicals sodium-alginate coating according to claim 1; It is characterized in that; In the said step (3); The mol ratio of the repeating unit of Periodic acid 99 or sodium periodate and sodium-alginate is (1-3): 10, and oxidizing reaction stirring reaction at least 24 hours under the lucifuge condition, preferred 24-40 hour; Adopt the terepthaloyl moietie termination reaction, the 96wt% alcoholic acid aqueous solution precipitates, post precipitation suction filtration, dialysis, and-80 ℃ of lyophilizes obtain many aldehyde radicals sodium-alginate.
5. the preparation method of a kind of many aldehyde radicals sodium-alginate coating according to claim 1; It is characterized in that; In the said step (4), in the reaction solution of said many aldehyde radicals sodium-alginate, many aldehyde radicals sodium-alginate 0.05-2mg/mL; NaCl0.15-0.55mol/L, sodium cyanoborohydride 0.01-0.1mg/mL; Temperature of reaction is 30 ℃-60 ℃, preferred 40-50 ℃; At least 2 hours reaction times, preferred 2-6 hour.
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| CN102861364A (en) * | 2012-10-16 | 2013-01-09 | 天津市第三中心医院 | Preparation method and application of dexamethasone sodium phosphate-sodium alga acid composite slow-release coating |
| CN102872484A (en) * | 2012-10-16 | 2013-01-16 | 天津市第三中心医院 | Preparation method of dexamethasone sodium phosphate composite sustained-release coating and application thereof |
| TWI622647B (en) * | 2017-05-19 | 2018-05-01 | 臺灣塑膠工業股份有限公司 | Support, method of making the same, and method of immobilizing microorganism |
| CN108384246A (en) * | 2018-04-09 | 2018-08-10 | 王景硕 | A kind of preparation method of addition thermal conductive Silica hydrogel |
| CN108503721A (en) * | 2018-03-28 | 2018-09-07 | 美瑞多生物科技（天津）有限公司 | With anticoagulant functions active polysaccharide and its preparation and application |
| CN111203115A (en) * | 2020-01-07 | 2020-05-29 | 天津市第三中心医院 | Oxidized polysaccharide anticoagulant coating hemodialysis membrane material and preparation method thereof |
| CN113244442A (en) * | 2021-06-01 | 2021-08-13 | 北京化工大学 | Application of polyamino cationic compound in preparation of surface procoagulant enhanced hemostatic material |
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| CN102861364A (en) * | 2012-10-16 | 2013-01-09 | 天津市第三中心医院 | Preparation method and application of dexamethasone sodium phosphate-sodium alga acid composite slow-release coating |
| CN102872484A (en) * | 2012-10-16 | 2013-01-16 | 天津市第三中心医院 | Preparation method of dexamethasone sodium phosphate composite sustained-release coating and application thereof |
| TWI622647B (en) * | 2017-05-19 | 2018-05-01 | 臺灣塑膠工業股份有限公司 | Support, method of making the same, and method of immobilizing microorganism |
| CN108503721A (en) * | 2018-03-28 | 2018-09-07 | 美瑞多生物科技（天津）有限公司 | With anticoagulant functions active polysaccharide and its preparation and application |
| CN108384246A (en) * | 2018-04-09 | 2018-08-10 | 王景硕 | A kind of preparation method of addition thermal conductive Silica hydrogel |
| CN111203115A (en) * | 2020-01-07 | 2020-05-29 | 天津市第三中心医院 | Oxidized polysaccharide anticoagulant coating hemodialysis membrane material and preparation method thereof |
| CN113244442A (en) * | 2021-06-01 | 2021-08-13 | 北京化工大学 | Application of polyamino cationic compound in preparation of surface procoagulant enhanced hemostatic material |
| CN113975463A (en) * | 2021-11-22 | 2022-01-28 | 湖南普林特医疗器械有限公司 | Porous tantalum implant with bioactive coating and preparation method thereof |
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