CN102924613A - Preparation method of dialdehyde bacterial cellulose - Google Patents
Preparation method of dialdehyde bacterial cellulose Download PDFInfo
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- CN102924613A CN102924613A CN2012104286649A CN201210428664A CN102924613A CN 102924613 A CN102924613 A CN 102924613A CN 2012104286649 A CN2012104286649 A CN 2012104286649A CN 201210428664 A CN201210428664 A CN 201210428664A CN 102924613 A CN102924613 A CN 102924613A
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Abstract
The invention discloses a preparation method of a dialdehyde bacterial cellulose, which comprises the following steps: preparing a bacterial cellulose; purifying the bacterial cellulose; treating the purified bacterial cellulose with an oxidizer; and washing with a glycol solution to obtain the dialdehyde bacterial cellulose. The dialdehyde bacterial cellulose has good degradability, high wet film porosity and water content and a large number of nano fiber structures. The dialdehyde bacterial cellulose has favorable application prospects in blood vessel engineering and organ stent materials.
Description
Technical field
The present invention relates to a kind of oxidation modifying method of bacteria cellulose, relate in particular to a kind of preparation method of dialdehyde bacteria cellulose.
Background technology
Along with the deterioration of growth in the living standard and environment, the disease of cardiovascular diseases has become the principal element that threatens China's people's health.Wherein coronary heart disease is occurred frequently not only in China, has more caused the high deadly rate of causing injury in European countries.Mainly treat by bypass surgery etc. at present, if but patient just by again recurrence or cause not having in the body blood vessel of the satisfied operation needs of high-quality because of different reasons after the recoveries from illness such as bypass surgery, must depend on the artificial blood vessel.But used artificial blood vessel's material and natural blood vessel do not mate aspect conformability at present, and therefore the easy hyperplasia that forms thrombus and cause inner membrance, is not suitable for small-caliber vascular in clinical application.The development of organizational project has fundamentally solved above problem.Bacteria cellulose is a kind of mainly by the spawn of acetic acid Pseudomonas in nutrient solution and Air Interface generation.Its natural nanofibrous structures of bacterial fibers procatarxis, strong mechanical property, good biocompatibility are widely used in the research of field of tissue engineering technology, are widely studied as vascular stent material especially in recent years.
The dialdehyde bacteria cellulose is to the hydroxyl oxidize on the bacteria cellulose prosposition carbon, makes bacteria cellulose part dialdehyde, thereby improves the degradation property of bacteria cellulose.Dialdehyde bacteria cellulose physical strength is high, good biocompatibility, the controllability of shape, degradability.Have a good application prospect at blood vessel engineering, organ timbering material.
Summary of the invention
The preparation method who the purpose of this invention is to provide the dialdehyde bacteria cellulose, it is high that the dialdehyde bacteria cellulose that the method is prepared has physical strength, good biocompatibility, the controllability of shape, high wet film porosity, water content, and the characteristics of a large amount of nanofibrous structures.
To achieve these goals, technical scheme of the present invention is: a kind of preparation method of dialdehyde bacteria cellulose is provided, may further comprise the steps:
(1) bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum, puts into again 0.1% sodium hydroxide solution, be heated to 80 ℃, changed one time sodium hydroxide solution in per two hours, boil 2～4 times, again flowing water flushing, by distilled water flushing to pH6.5～7.5;
(2) bacterial cellulose gel after step (1) processing being added concentration is in the sodium periodate solution of 0.1～0.5mol/L, in 36 ℃～38 ℃ reaction 3～9h;
(3) with the washing of 0.1mol/L ethylene glycol solution, remove through the sodium periodate in the bacterial cellulose gel after step (2) processing;
(4) with the bacterial cellulose gel after distilled water washing process step (3) processing, until the color of starch potassium iodide paper is not blueness, obtain the dialdehyde bacteria cellulose.
The preparation method of dialdehyde bacteria cellulose of the present invention, the concentration-response time of used sodium periodate will be got hold of.
Preferably, raw material is biosynthetic bacteria cellulose, and the related microorganism of biosynthesizing is acetobacter xylinum.
Preferably, the reaction oxygenant is sodium periodate solution, and sodium periodate solution concentration is in the sodium periodate solution of 0.1～0.5mol/L, in 36 ℃～38 ℃ reaction 6h.
The present invention is take sodium periodate as oxygenant, to the bacteria cellulose oxidation.It is high that bacteria cellulose after the oxidation has not only kept the original physical strength of bacteria cellulose, good biocompatibility, the controllability of shape, high wet film porosity, water content, and a large amount of nanofibrous structures.And the more important thing is the degradation property that has in vivo.Have a good application prospect at blood vessel engineering, organ timbering material.
Description of drawings
Fig. 1 is that the sodium periodate oxidation Mierocrystalline cellulose generates the dialdehyde cellulose schematic diagram;
Fig. 2 is different degree of oxidation bacteria cellulose infrared spectrums;
Fig. 3 is different aldehyde group content sample surface morphology figure; BC: unmodified bacteria cellulose; B, C, G, F, I are the dialdehyde bacteria cellulose of different aldehyde group contents;
Fig. 4 is different aldehyde group content sample section shape appearance figures; BC: unmodified bacteria cellulose; B, C, G, F, I are the dialdehyde bacteria cellulose of different aldehyde group contents;
The different degree of oxidation modified bacteria cellulose of Fig. 5 wet film porosity change figure; BC: unmodified bacteria cellulose; A-I: the dialdehyde bacteria cellulose of different degree of oxidations;
Fig. 6 is the water-content figure of different degree of oxidation modified bacteria celluloses; BC: unmodified bacteria cellulose; A-I: the dialdehyde bacteria cellulose of different degree of oxidations;
Fig. 7 is the variation diagram of the degradation rate of differential responses time experimental group; BC: unmodified bacteria cellulose; A-I: the dialdehyde bacteria cellulose of different degree of oxidations;
Fig. 8 is the degradation rate variation diagram of different aldehyde group content samples under the identical degradation time; BC: unmodified bacteria cellulose; A-I: the dialdehyde bacteria cellulose of different degree of oxidations.
Embodiment
Example 1: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacterial cellulose gel is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.1 mol/L, in 37 ℃ of reaction 3h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 9.80% of total amount after measured.
Example 2: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.1 mol/L, in 37 ℃ of reaction 6h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 11.02% of total amount after measured.
Example 3: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.1 mol/L, in 37 ℃ of reaction 9h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 22.27% of total amount after measured.
Example 4: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.3mol/L, in 37 ℃ of reaction 3h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 33.74% of total amount after measured.
Example 5: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.3mol/L, in 37 ℃ of reaction 6h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 37.55% of total amount after measured.
Example 6: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.3mol/L, in 37 ℃ of reaction 9h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 46.16% of total amount after measured.
Example 7: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.4mol/L, in 37 ℃ of reaction 3h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 37.21% of total amount after measured.
Example 8: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.4mol/L, in 37 ℃ of reaction 6h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 42.89% of total amount after measured.
Example 9: bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum; Again bacteria cellulose is put into 0.1% sodium hydroxide solution, is heated to 80 ℃, changed sodium hydroxide solution one time in per two hours, boil 3 times, again flowing water flushing, by distilled water flushing to pH be 7.Again bacterial cellulose gel is added in the sodium periodate solution that concentration is 0.4mol/L, in 37 ℃ of reaction 9h, then through 0.1mol/L ethylene glycol solution washing, wash again with distilled water afterwards, until the color of starch potassium iodide paper is not blueness.The content of aldehyde radical accounts for 61.86% of total amount after measured.
1, the variation of dialdehyde bacteria cellulose aldehyde group content
Sodium periodate to the oxidizing reaction of bacteria cellulose as shown in Figure 1, has the sodium periodate of strong oxidizing property with 2 on the bacteria cellulose glucose unit, hydroxyl oxidize on 3 carbon, become aldehyde radical, this is also so that 2, key fracture between 3 carbon makes to occur the dialdehyde group on the bacteria cellulose monomer.Fig. 2 is for detecting the spectrogram that obtains through Fourier's infrared scan.BC is unmodified bacteria cellulose among the figure, and A～I is the bacteria cellulose through the reacted modification of sodium periodate.The weak aldehyde radical peak characteristic peak of locating about 1740cm-1 to have occurred not going out on the unmodified bacteria cellulose spectrogram through the experimental group of sodium periodate oxidation as we can see from the figure.And also about 880cm-1, locate to have occurred the hemiacetal characteristic peak.The infrared peak of dialdehyde cellulose of describing in the articles [45] such as these characteristic peaks and Li Jian is consistent, illustrate to pass through the sodium periodate oxidation modification, and the glucose monomer in the bacteria cellulose part chain is oxidized generation dialdehyde group.And the intensity of the hydroxyl peak of locating about 3412cm-1 is compared to unmodified bacteria cellulose group and also decreases, and showing has hydroxyl to disappear.Find also that in the drawings the C-O peak at 1068cm-1 place and the O-H absorption peak at 1112cm-1 place appear in the unmodified bacteria cellulose group, and in each modified bacteria cellulose group, do not occur, this hydroxyl that further shows the prosposition carbon on the glucose monomer in the bacteria cellulose reacts.Illustrate that some Mierocrystalline cellulose is oxidized.
Obtained to react by oxammonium hydrochloride behind the oxidizing bacteria cellulose degree of oxidation of quantitative assay oxidizing bacteria cellulose, namely represented with aldehyde group content.The height that how much has reflected the sample degree of oxidation of aldehyde group content is an important index of sodium periodate oxidation reaction.The aldehyde group content of each experimental group obtain is measured in this experiment by hydroxyamine hydrochloride, the result with
Form represent.The results are shown in Table 2-2.
The aldehyde group content of table 2-2 different experiments group
2, different aldehyde group contents are on the impact of bacteria cellulose physicals
Fig. 3 is that the bacteria cellulose of choosing different degree of oxidations carries out the comparison of surface topography, the aldehyde group content size of experimental group is successively: BC＜B＜C＜G＜F＜I, observe and find, B, C, G experimental group oxidizing bacteria cellulose are organized the diameter chap that unmodified bacteria cellulose is compared the surface portion fiber with BC, so that part is mesh-structured no longer loose as the unmodified fibers element, but become compact.The surface topography of F and I experimental group oxidizing bacteria cellulose is more obvious than above several groups of variations, can find out among the figure F and I the group oxidizing bacteria cellulose surperficial most of fiber fusion together so that surface apertures greatly dwindle.Although B, C, G experimental group sample surfaces have the chap of part fiber yarn, but still exist and the equal big or small cellulose silk of unmodified fibers element.And aldehyde group content merges greater than most cellulose silk chap in 40% F group and the I group, and the surface only has the existence of the nano-grade cellulosic silk of only a few.Relatively F group, I group surface topography are found, the hole amount on F group oxidizing bacteria cellulose surface than the I group many and also intensive.This may be because the degree of oxidation that I organizes is higher than the F group, has caused I group cellulose surface to have more cellulose silk chap to merge, just so that its surface porosity factor decline.Fig. 4 is the internal morphology of same experimental group oxidizing bacteria cellulose, still there is the nano-grade cellulosic silk in the bacteria cellulose inside that can find out in the drawings different degree of oxidations, B, C experimental group internal morphology and unmodified bacteria cellulose group do not have very large difference, all have onesize cellulose silk.The degree of oxidation of G, F, I experimental group raises gradually, and as can be seen from Figure, along with the rising of degree of oxidation, the part cellulose silk flocks together gradually.The inside of the highest I of degree of oxidation group oxidizing bacteria cellulose even the phenomenon of laminate structure thickening occurs, this may be exactly because the intensification of degree of oxidation, and the laminate structure of bacteria cellulose inside is glued to be linked togather and is caused.From the variation of the microscopic appearance of the bacteria cellulose group of oxidation, find, along with the intensification of degree of oxidation, i.e. the increase of aldehyde group content, the bacteria cellulose silk can flock together gradually, even inner laminate structure is assembled mutually, caused the contraction of part fibrous reticulum pore structure.Its surface of the oxidizing bacteria cellulose that aldehyde group content is high in this experiment and inner microtexture are compared in unmodified bacteria cellulose, change relatively obvious, the surface portion aperture dwindles obviously, cellulose silk is assembled closely, and the microscopic appearance of the lower experimental group of degree of oxidation connects and is bordering on unmodified experimental group BC group, and too large variation occurs.
Fig. 5 is the wet film porosity of the different degree of oxidations of mensuration, and unmodified bacteria cellulose is that the BC group has very high wet film porosity as can be seen from Figure, more than 98%.The wet film porosity of the bacteria cellulose after the modification still has high wet film porosity also still more than 95%, but from general terms, along with increasing of degree of oxidation, the porosity under its wet film state also has a declining tendency.Fig. 6 is the water content of the modified bacteria cellulose under the different oxidisabilities, as can be seen from Figure, along with increasing of degree of oxidation, the water content of modified bacteria cellulose also presents downtrending substantially, but water content still has very high wetting ability still more than 90%.
This may be that such as the contraction of fiber, the change of the hydrogen bond structure of Mierocrystalline cellulose inside also may cause the variation of wet film porosity and water-content because the intensification of degree of oxidation makes bacteria cellulose change in the part microtexture.
3, the degradation rate of different oxidisability bacteria celluloses changes
The n cell epimatrix mainly is intertwined to form by tens thiozells to the hundreds of nanometer.The more approaching material of research discovery in recent years and n cell epimatrix structure more is conducive to the adhesion growth of cell.Bacteria cellulose is as a kind of material of the natural netted structure of nanofiber, it also is a kind of highly purified Mierocrystalline cellulose, although can in the environment that acid, alkali and cellulase exist, degrade in a large number, in the internal milieu of weak base, not have again cellulase, so in vivo than difficult degradation.Utilize the sodium periodate oxidation bacteria cellulose, generate the dialdehyde group, make the variation of charge distribution in the Mierocrystalline cellulose unit, caused the fracture of glycosidic link thereby form β-alkoxy carbonyl structure, Mierocrystalline cellulose is degraded.Fig. 7 be the different experiments group under the different time, the degradation rate in SBF solution.Wherein, A-I bar curve represents respectively the A-I experimental group, and the BC curve represents control group, i.e. the Mierocrystalline cellulose group of not oxidised modification.As can be seen from Figure, unmodified bacteria cellulose group, namely the degraded of BC group is very slow.In identical degradation time, degraded in various degree all occurs in each modified bacteria cellulose group, and its degradation rate all is much higher than unmodified bacteria cellulose group.And along with the prolongation of degradation time, the degradation rate of modified bacteria cellulose group also all rises to some extent, and early stage what degrade, the degradation speed of oxidizing bacteria cellulose is much larger than unmodified bacteria cellulose.This SURGICEL that shows that the method for oxidation of meso-periodic acid sodium by experiment obtains all has degradability.As can be known in the scope of this research, identical oxidant concentration, aldehyde group content (being the degree of oxidation) increases along with the prolongation in reaction times, and in the identical reaction times, the content of aldehyde radical also is that the concentration along with oxygenant rises and increases.In order to show more intuitively the relation of aldehyde group content and degradation rate, get degradation rate and the aldehyde group content that 168h surveys and do histogram (Fig. 8), letter mark on the figure is respectively each experimental group group number, by finding out very intuitively the degradation rate of each experimental group and the variation relation of aldehyde group content among the figure.Show the height of aldehyde group content and how much being directly proportional substantially of cellulosic degradation rate, suitable control aldehyde group content just can play effective regulating and controlling effect to degradation rate.
Can be drawn by above experiment, the dialdehyde bacteria cellulose that obtains after the oxidation modification has possessed degradation property, unmodified bacteria cellulose original high wet film porosity, water content have been kept simultaneously, and a large amount of nanofibrous structures, the dialdehyde bacteria cellulose has a good application prospect at blood vessel engineering, organ timbering material.
Above disclosed only is preferred embodiment of the present invention, certainly can not limit with this interest field of the present invention, and the equivalent variations of therefore doing according to claim of the present invention still belongs to the scope that the present invention is contained.
Claims (1)
1. the preparation method of a dialdehyde bacteria cellulose is characterized in that may further comprise the steps:
(1) bacterial cellulose gel is put in the substratum that wash and remove residual in the flowing water contains acetobacter xylinum, puts into again 0.1% sodium hydroxide solution, be heated to 80 ℃, changed one time sodium hydroxide solution in per two hours, boil 2～4 times, again flowing water flushing, by distilled water flushing to pH6.5～7.5;
(2) bacterial cellulose gel after step (1) processing being added concentration is in the sodium periodate solution of 0.1～0.5mol/L, in 36 ℃～38 ℃ reaction 3～9h;
(3) with the washing of 0.1mol/L ethylene glycol solution, remove through the sodium periodate in the bacterial cellulose gel after step (2) processing;
(4) with the bacterial cellulose gel after distilled water washing process step (3) processing, until the color of starch potassium iodide paper is not blueness, obtain the dialdehyde bacteria cellulose.
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| CN104277245A (en) * | 2013-07-04 | 2015-01-14 | 南京林业大学 | Method for preparation of crop straw enhanced starch plastic by C2 and 3-site oxidation |
| CN105254770A (en) * | 2015-11-13 | 2016-01-20 | 广西大学 | Preparing method for dialdehyde nano-crystalline cellulose |
| EP3064231A1 (en) * | 2015-03-05 | 2016-09-07 | Jörg Rodermann | Mixing material, stent and method for making a stent |
| CN106519285A (en) * | 2016-09-23 | 2017-03-22 | 嘉兴赛维环保科技有限公司 | Preparation method for three-dimensional network structure flocculation material structured by bacterial cellulose |
| CN106620809A (en) * | 2017-01-18 | 2017-05-10 | 山东纳美德生物科技有限公司 | Preparation method of bacterial cellulose membrane-based antibacterial dressing |
| CN106675523A (en) * | 2016-12-11 | 2017-05-17 | 汪逸凡 | Preparation method of biodegradable high oil absorption material |
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| CN113957738A (en) * | 2021-10-27 | 2022-01-21 | 山东纳美德生物科技有限公司 | Method for removing endotoxin in bacterial cellulose |
| CN114163540A (en) * | 2021-12-09 | 2022-03-11 | 中国海洋大学 | Dual-functional bacterial cellulose compound, preparation method and application thereof |
| CN116158994A (en) * | 2023-02-27 | 2023-05-26 | 天津科技大学 | Caries preventing toothpaste containing 2,3-dialdehyde microcrystalline cellulose and preparation method thereof |
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| CN104277245A (en) * | 2013-07-04 | 2015-01-14 | 南京林业大学 | Method for preparation of crop straw enhanced starch plastic by C2 and 3-site oxidation |
| EP3064231A1 (en) * | 2015-03-05 | 2016-09-07 | Jörg Rodermann | Mixing material, stent and method for making a stent |
| CN105254770A (en) * | 2015-11-13 | 2016-01-20 | 广西大学 | Preparing method for dialdehyde nano-crystalline cellulose |
| CN106519285A (en) * | 2016-09-23 | 2017-03-22 | 嘉兴赛维环保科技有限公司 | Preparation method for three-dimensional network structure flocculation material structured by bacterial cellulose |
| CN106675523A (en) * | 2016-12-11 | 2017-05-17 | 汪逸凡 | Preparation method of biodegradable high oil absorption material |
| CN106620809A (en) * | 2017-01-18 | 2017-05-10 | 山东纳美德生物科技有限公司 | Preparation method of bacterial cellulose membrane-based antibacterial dressing |
| CN107033919A (en) * | 2017-05-14 | 2017-08-11 | 吴刚 | A kind of preparation method of sand-consolidating agent |
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| CN109134671A (en) * | 2018-07-12 | 2019-01-04 | 厦门大学 | A kind of preparation method of the cellulose derivative of imido- furans |
| CN111097388A (en) * | 2018-10-26 | 2020-05-05 | 南京化学工业园环保产业协同创新有限公司 | Preparation of biodegradable oil absorption material |
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| CN111320770A (en) * | 2020-04-20 | 2020-06-23 | 张丙起 | Biological gel for burn department for accelerating wound healing and preparation method thereof |
| CN111320770B (en) * | 2020-04-20 | 2021-01-12 | 青岛大学附属医院 | Biological gel for burn department for accelerating wound healing and preparation method thereof |
| CN113957738A (en) * | 2021-10-27 | 2022-01-21 | 山东纳美德生物科技有限公司 | Method for removing endotoxin in bacterial cellulose |
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| CN114163540B (en) * | 2021-12-09 | 2022-10-21 | 中国海洋大学 | Dual-functional bacterial cellulose compound, preparation method and application thereof |
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Application publication date: 20130213 |