CN101167706A - Method for synthesizing chitosan nano mcirocapsule - Google Patents
Method for synthesizing chitosan nano mcirocapsule Download PDFInfo
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- CN101167706A CN101167706A CNA2007101339910A CN200710133991A CN101167706A CN 101167706 A CN101167706 A CN 101167706A CN A2007101339910 A CNA2007101339910 A CN A2007101339910A CN 200710133991 A CN200710133991 A CN 200710133991A CN 101167706 A CN101167706 A CN 101167706A
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Abstract
The synthesis of chitosan nanometer microcapsule can be widely used as drug carrier or biological medical material. The process for preparation comprises a. preparing water-in-oil type of anti-phase micro-emulsified system of solution by common method, b. charging chitose or derivant of chitose to the micro-emulsified system of solution, dispersing the chitose or derivant of chitose by the interfacial energy, c. charging cross linking agent TPP, compounding the chitose or derivant of chitose and the cross linking agent by automatically attraction of positive and negative electric charge into capsules in the micro-emulsified system of solution, d. centrifuge treating the solution in procedure c and removing the supernatant, by which the chitose /TPP nanometer microcapsule or derivant of chitose /TPP nanometer microcapsule can be finished, and finally washing and conserving the microcapsules by absolute ethyl alcohol. The invention avoids the defective effect of capsule materials in prior nanometer microcapsule, and has the advantages of excellent bioavailability, easy degradation, low cost, wide source of chitose and TPP, as well as simple and quick operation, and good effect of encapsulation.
Description
Technical field
The present invention can be used as pharmaceutical carrier or bio-medical material extensive use, belongs to the technical field of capsule of nano preparation.
Background technology
Bio-microcapsule promptly is meant the microcapsule of having fixed biological tissue or cell with the semi permeability thin film, because semipermeable microcapsule membrane has played the effect of cell membrane, the form and the function of microcapsule exactly like cell, so also be referred to as " artificial cell ".Material is one of key factor of decision microcapsule performance.Generally require its filming performance good, do not react, and should have certain mechanical strength, stability with encapsulation object; For the microcapsule of using in the biotic environment, material also will possess good biocompatibility; (as medicine controlled releasing) then needs to have biodegradability in some cases.The microencapsulation material that uses in the research report mainly contains natural, semi-synthetic and synthesized polymer material 3 big classes at present.Often there is behind the big or salify of certain toxicity or viscosity the facile hydrolysis because dissolubility is big in some capsule material, so should not high-temperature process or be used for shortcomings such as clinical product is very limited.At present, but the material of biodegradable and bio-absorbable be subjected to general attention and be widely used.The preparation method of bio-microcapsule can be divided into again: the physics method, and chemical method, physical-chemical process wherein has certain methods to be difficult for realizing or being awkward.Therefore the capsule material choose and the design of preparation method to particle diameter, drug loading, the sustained release performance of bio-microcapsule, performances such as biocompatibility have significance.
The problem of formulation and technology part Study existence at present is mainly reflected in:
(1) selection of capsule material: the capsule material is to biocompatibility, carrying drug ratio, and the influence of degradability is extremely important.At present, to have good biocompatibility and degradable substance be the focus of research as the capsule material to pure natural always.Chitosan and derivant thereof are the carrier material of quite being favored very early, because they can be decomposed by the intravital lysozyme of people, catabolite can not bring any harm to health, and this is that synthetic high polymer and some natural polymers are incomparable.And various advantages that nearly 2 years oligochitosans exist and in food manufacturing, biological engineering, the advantage in the fields such as health care is remarkable day by day.
(2) selection of preparation method: the preparation method of bio-microcapsule has chemical method (interfacial polymerization, emulsion process, microemulsion method) at present, physics method (air suspension, electrostatic deposition, Mechanical Method), physical-chemical process (phase separation method, solvent evaporated method, interface sedimentation, spray drying method).Though Mechanical Method has certain application but is difficult to promote the use of because of the special equipment of needs in the physical method on capsule technologies of preparing such as lipid granule.Though emulsion polymerisation is used wider as the effective means of the combination of a kind of organic and inorganic particle and organic coating, but also exist significant limitation, nearest raising along with domestic research level, microemulsion polymerization method is because easy and simple to handle, system is stable, and the grain diameter homogeneous of formation becomes the focus of research gradually.Microemulsion is the thermodynamically stable, isotropic of two kinds of immiscible liquid formation, appearance transparent or translucent dispersion.Microemulsion polymerization method not only is used widely at aspects such as daily-use chemical industry and tertiary oil recoveries, and aspect such as synthetic and nano material preparation also is subject to people's attention day by day at biochemical reaction, medicine.Because different microemulsion systems can a large amount of hydrophilic or oleophilic substance of solubilising, and can change the oil-water interfacial film composition by regulating factors such as composition, temperature, salinity and oil-water ratio, thereby change effects such as solubilizing amount and slow release, so microemulsion system is subjected to extensive concern as pharmaceutical carrier in recent years.The capsule that microemulsion polymerization method forms, the capsule type is better, and conditional stability is easy to control, and advantage such as preparation method easy operating.
Summary of the invention
Technical problem: technical problem to be solved by this invention provides a kind of synthetic method of chitosan nano mcirocapsule, poor at the biocompatibility that existed in the former bio-microcapsule preparation, be difficult for degradation in vivo and preparation method is loaded down with trivial details, the problem that practical operation condition and drug dosage are difficult to grasp in the preparation process of bio-microcapsule, chitosan and derivant thereof that the present invention selects for use natural easy degraded to have the good biological safety are the capsule material, with TPP is that cross-linking agent passes through electrostatic interaction polymerization encystation in microemulsion system, method is simple to operation, and the product encystation is good, and safety is degraded easily.
Technical scheme: the present invention is a raw material with chitosan (CS) and sodium tripolyphosphate (TPP), utilize W/O reverse microemulsion system, reference literature (Ting Wang, Zhangqi Feng, Nongyue He, A NovelPreparation of Nanocapsules from Alginate-Oligochitosan, Journal ofNanoscience and Nanotechnology) the chitosan of having established and sodium alginate the best in the reverse microemulsion liquid system form point, set up microemulsion system (oil phase, surfactant, cosurfactant three optimum volume ratio is 64: 12: 9).For preparing Nano capsule to impinging upon in the consubstantiality system, use transmission electron microscope with the oligochitosan that do not add TPP and sodium alginate, scanning electron microscope has carried out the measurement of morphology observation and mean diameter to capsule.Advantages such as it is good to find to have the encystation scrotiform with the TPP complexation, and preparation method is simple quick.
The technology of the present invention solution is:
A. adopt conventional method to prepare water-in-oil type reverse microemulsion system solution;
B. drip chitosan or chitosan derivatives in described microemulsion system, the interface energy that has with microemulsion system itself disperses;
C. add cross-linking agent TPP, chitosan or chitosan derivatives and cross-linking agent TPP attract the polymerization encystation automatically by positive and negative charge in microemulsion system solution;
D. solution among the step c is carried out centrifugal treating, abandoning supernatant just obtains chitosan/TPP capsule of nano or chitosan derivatives/TPP capsule of nano, at last capsule of nano is preserved with absolute ethanol washing.
In the described water-in-oil type reverse microemulsion system solution, oil phase is: a kind of in Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, the cyclohexane extraction, surfactant is: AOT[2 one ethylhexyl], a kind of among the AOS, sodium lauryl sulphate, sodium cetanesulfonate, n-amyl alcohol, cetyl trimethyl ammonium bromide, cosurfactant is: octyl phenyl polyoxyethylene ether (Triton-100).Reference literature 1 (Ting Wang, Zhangqi Feng, Nongyue He, A Novel Preparation of Nanocapsules from Alginate-Oligochitosan, Journal of Nanoscience andNanotechnology), three's mixing is promptly obtained preparing the needed microemulsion system of nano-particle.Described oil phase, surfactant, cosurfactant three volume ratio is 64: 12: 9.
Beneficial effect: the present invention prepares and selects for use natural in the process of bio-microcapsule and to the non-stimulated natural capsule material of human body such as chitosan and derivant thereof, TPP, and utilize microemulsion system and macromole self assembly principle, be all the polyelectrolyte complex properties of materials by the two, make the two pass through charge attraction complexation encystation.And with reference to the determined microemulsion environment of article.Chitosan is the product of de-acetyl chitin, have with mucopolysaccharide like structure, nontoxic, biology can absorb, catabolite can not cause biological tissue's disorder.Wide material sources, therefore at cell culture, aspects such as microorganism culturing and pharmaceuticals industry have all shown its superiority.The brothers hydroxyl of this cationic polymer and amino can dissolve it with acid reaction, make the medicine permeability big at alkaline environment at the sour environment ratio, and therefore, the chitosan controlled release has certain targeting.The material that with the chitosan is substrate also can form colloid under sour environment, this can reduce medicine again to the stimulation of tissue and help to continue to discharge.Chitosan also has many biological activitys favourable to human body, as antitumor action, immunological adjuvant effect and promotion tissue repair and anastalsis etc.Utilize chitosan cationic characteristic and the automatic polymerization reaction take place of charged anion can prepare dissimilar microcapsules; Outstanding more is that chitosan derivatives and degradation of chitosan thing are the developing direction that gets a good chance of as carrier.Sodium tripolyphosphate (TPP) has performances such as wide material sources, low price, good biocompatibility, and it can be by both electrostatic interaction and chitosan polymerization encystation.
Description of drawings
Fig. 1 is the synthetic sketch map of chitosan/TPP nano microcapsule;
Fig. 2 is respectively the capsule of nano transmission electron microscope picture that does not add TPP;
Fig. 3 is respectively the capsule of nano sem photograph behind the adding TPP.
The specific embodiment
Solution concentration is the oligochitosan aqueous solution of 1% (w/t) to 10% (w/t), the TPP of solution concentration 0.5% (w/t) to 5% (w/t), with microemulsion system as reaction environment, wherein the oil phase that microemulsion system is commonly used is commonly used Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, cyclohexane extraction etc., surfactant is commonly used the AOT[2-ethylhexyl], AOS, SDS (sodium lauryl sulphate), SDBS (sodium cetanesulfonate), n-amyl alcohol, CTAB (cetyl trimethyl ammonium bromide) etc., cosurfactant can be selected Triton-100 (polyethenoxy ether class), OP etc. for use.The percent by volume of described each component of microemulsion system is 64: 12:9.The present invention adopt the prepared with microemulsion reactor nano-particle with chitosan+sodium alginate self assembly polymerization encystation be control systems to prepare chitosan+TPP, TPP+ chitosan+sodium alginate etc. a series of be cross-linking agent with TPP, oligochitosan is the bio-microcapsule of capsule material.Through scanning electron microscope, transmission electron microscope observing, contrast determine to add the effective and Dispersion of Particles of nano-particle encystation of TPP.
One, the preparation of nano-particle
Embodiment 1: oligochitosan+sodium alginate+microemulsion system (control systems)
Select cyclohexane extraction for use at oil phase Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, cyclohexane extraction etc.; ((sodium cetanesulfonate, n-amyl alcohol are selected n-amyl alcohol for use among the CTAB (cetyl trimethyl ammonium bromide) etc. for sodium lauryl sulphate, SDBS for surfactant A OT[2-ethylhexyl, AOS, SDS; Cosurfactant is selected octyl phenyl polyoxyethylene ether (Triton-100) for use.Triton-100, n-amyl alcohol, cyclohexane extraction is formed microemulsion system.
1 three presses oil phase with reference to article, surfactant, and cosurfactant three volume ratio is that the proportioning of oil phase 64:12:9 adds, and promptly obtains transparent microemulsion system.Oligochitosan is dissolved in 5 milliliters of the solution of the oligochitosan that is made into concentration about 2% in the distilled water, slowly adds 5 milliliters of about 2% sodium alginate solns thereafter.Stirred about 10 minutes being not less than under 1000 revolutions per seconds the rotating speed, promptly get capsule of nano as shown in Figure 2 with twice abandoning supernatant of 10000 rev/mins of centrifugal 10 minutes reuse absolute ethanol washings behind the absolute ethanol washing.
Embodiment 2: oligochitosan+TPP+ microemulsion system
Oiliness base Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, cyclohexane extraction etc. select for use octadecanol; Surfactant A OT[2 one ethylhexyl], AOS, SDS (sodium lauryl sulphate), SDBS (sodium cetanesulfonate), n-amyl alcohol is selected SDS for use among the CTAB (cetyl trimethyl ammonium bromide) etc.; Cosurfactant is selected octyl phenyl polyoxyethylene ether (Triton-100) for use.
With octadecanol, SDS (octadecanol: SDS=60: 12) be organic solvent, add about 9 milliliters cosurfactant Triton-100, obtain transparent microemulsion system, oligochitosan is dissolved in the solution of the oligochitosan that is made into concentration about 8% in the distilled water, slowly adds about 5 milliliters of about 5% TPP solution.Stirred about 10 minutes being not less than under 1000 revolutions per seconds the rotating speed, promptly get nano microcapsule such as Fig. 3 twice with 10000 rev/mins of centrifugal 10 minutes reuse absolute ethanol washings behind the absolute ethanol washing, it is better that such microcapsule of comparing with embodiment 1 (Fig. 2) is difficult for the reunion encystation.
Embodiment 3: carboxymethyl chitosan+TPP+ microemulsion system
Oiliness base Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, cyclohexane extraction etc. select for use octadecanol; Surfactant A OT[2 one ethylhexyl], AOS, SDS (sodium lauryl sulphate), SDBS (sodium cetanesulfonate), n-amyl alcohol is selected SDS for use among the CTAB (cetyl trimethyl ammonium bromide) etc.; Cosurfactant is selected octyl phenyl polyoxyethylene ether (Triton-100) for use.
With octadecanol, SDS (octadecanol: SDS=64: 12) be organic solvent, add about 9 milliliters cosurfactant Triton-100, obtain transparent microemulsion system, the dissolving carboxymethyl chitosan is made into the solution of the oligochitosan of concentration about 8% in distilled water, slowly adds about 5 milliliters of about 3% TPP solution.Stirred about 10 minutes being not less than under 1000 revolutions per seconds the rotating speed, promptly get capsule of nano twice with 10000 rev/mins of centrifugal 10 minutes reuse absolute ethanol washings behind the absolute ethanol washing.
Embodiment 4: oligo-glucosamine+TPP+ microemulsion system
Select cyclohexane extraction for use at oiliness base Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, cyclohexane extraction etc.; Surfactant A OT[2 one ethylhexyl], AOS, SDS (sodium lauryl sulphate), SDBS (sodium cetanesulfonate), n-amyl alcohol is selected n-amyl alcohol for use among the CTAB (cetyl trimethyl ammonium bromide) etc.; Cosurfactant is selected octyl phenyl polyoxyethylene ether (Triton-100) for use.
With n-amyl alcohol, cyclohexane extraction (n-amyl alcohol: cyclohexane extraction=64: 12) be organic solvent, add about 9 milliliters cosurfactant Triton-100, obtain transparent microemulsion system, oligo-glucosamine is dissolved in the oligo-glucosamine solution that is made into concentration about 1% in the distilled water, slowly adds about 5 milliliters of about 0.5% TPP solution.Stirred about 10 minutes being not less than under 1000 revolutions per seconds the rotating speed, promptly get capsule of nano twice with 10000 rev/mins of centrifugal 10 minutes reuse absolute ethanol washings behind the absolute ethanol washing.
Embodiment 5: oligochitosan+sodium alginate+TPP+ microemulsion system
Select cyclohexane extraction for use at oiliness base Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, cyclohexane extraction etc.; Surfactant A OT[2 one ethylhexyl], AOS, SDS (sodium lauryl sulphate), SDBS (sodium cetanesulfonate), n-amyl alcohol is selected n-amyl alcohol for use among the CTAB (cetyl trimethyl ammonium bromide) etc.; Cosurfactant is selected octyl phenyl polyoxyethylene ether (Triton-100) for use.
With n-amyl alcohol, cyclohexane extraction (n-amyl alcohol: cyclohexane extraction=64: 12) be organic solvent, add about 9 milliliters cosurfactant Triton-100, obtain transparent microemulsion system, 5 milliliters of the solution of the sodium alginate of adding 10%, slowly the oligochitosan solution of adding about 10% is about 5 milliliters, last 5 milliliters of the 5%TPP solution that slowly add.Stirred about 10 minutes being not less than under 1000 revolutions per seconds the rotating speed, abandon supernatant for twice with 10000 rev/mins of centrifugal 10 minutes reuse absolute ethanol washings behind the absolute ethanol washing and promptly get capsule of nano.
Claims (3)
- A chitosan nano mcirocapsule synthetic method, it is characterized in that preparation process is:A. adopt conventional method to prepare water-in-oil type reverse microemulsion system solution;B. drip chitosan or chitosan derivatives in described microemulsion system, the interface energy that has with microemulsion system itself disperses;C. add cross-linking agent TPP, chitosan or chitosan derivatives and cross-linking agent TPP attract the polymerization encystation automatically by positive and negative charge in microemulsion system solution;D. solution among the step c is carried out centrifugal treating, abandoning supernatant just obtains chitosan/sodium tripolyphosphate capsule of nano or chitosan derivatives/sodium tripolyphosphate capsule of nano, at last capsule of nano is preserved with absolute ethanol washing.
- Chitosan nano mcirocapsule according to claim 1 synthetic method, it is characterized in that in the described water-in-oil type reverse microemulsion system solution, oil phase is: Oleum Ricini, Oleum Glycines, Oleum sesami, liquid paraffin, white vaseline, lanoline, hexadecanol, octadecanol, a kind of in the cyclohexane extraction, surfactant is: AOT[2 one ethylhexyl], AOS, sodium lauryl sulphate, sodium cetanesulfonate, n-amyl alcohol, a kind of in the cetyl trimethyl ammonium bromide, cosurfactant is the octyl phenyl polyoxyethylene ether, the three is mixed promptly obtaining preparing the needed microemulsion system of nano-particle.
- Chitosan nano mcirocapsule according to claim 2 synthetic method, it is characterized in that described oil phase, surfactant, cosurfactant three volume ratio is 64: 12: 9.
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| CN107699558A (en) * | 2017-11-23 | 2018-02-16 | 湖北文理学院 | Immobilised enzymes, its preparation method and its application in atrazine-contaminated soil is repaired |
| US10053616B2 (en) | 2015-04-09 | 2018-08-21 | Saudi Arabian Oil Company | Encapsulated nanocompositions for increasing hydrocarbon recovery |
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- 2007-10-26 CN CNA2007101339910A patent/CN101167706A/en active Pending
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| EP2460516A4 (en) * | 2009-07-28 | 2014-01-08 | Univ Pais Vasco | Lipid nanoparticles for gene therapy |
| CN102698664A (en) * | 2012-05-26 | 2012-10-03 | 云南恩典科技产业发展有限公司 | Method for preparing water microcapsule |
| US10053616B2 (en) | 2015-04-09 | 2018-08-21 | Saudi Arabian Oil Company | Encapsulated nanocompositions for increasing hydrocarbon recovery |
| US10550310B2 (en) | 2015-04-09 | 2020-02-04 | Saudi Arabian Oil Company | Encapsulated nanocompositions for increasing hydrocarbon recovery |
| US10550311B2 (en) | 2015-04-09 | 2020-02-04 | Saudi Arabian Oil Company | Encapsulated nanocompositions for increasing hydrocarbon recovery |
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| CN105494430A (en) * | 2015-12-16 | 2016-04-20 | 河北科技大学 | Silver-loaded low-molecular-weight chitosan composite microsphere antibacterial agent and preparation method thereof |
| CN105494430B (en) * | 2015-12-16 | 2018-03-06 | 河北科技大学 | One kind carries silver-colored low-molecular weight chitoglycan complex microsphere antiseptic and preparation method thereof |
| US10538693B2 (en) | 2016-01-13 | 2020-01-21 | Saudi Arabian Oil Company | Stabilization of petroleum surfactants for enhancing oil recovery |
| US10125307B2 (en) | 2016-01-13 | 2018-11-13 | Saudi Arabian Oil Company | Stabilization of petroleum surfactants for enhancing oil recovery |
| CN107699558A (en) * | 2017-11-23 | 2018-02-16 | 湖北文理学院 | Immobilised enzymes, its preparation method and its application in atrazine-contaminated soil is repaired |
| WO2019175240A1 (en) * | 2018-03-13 | 2019-09-19 | Novozymes A/S | Microencapsulation using amino sugar oligomers |
| CN111770788A (en) * | 2018-03-13 | 2020-10-13 | 诺维信公司 | Microencapsulation using amino sugar oligomers |
| CN109007807A (en) * | 2018-08-13 | 2018-12-18 | 上海应用技术大学 | A kind of microcapsules fruit ferment powder and preparation method thereof |
| CN113396907A (en) * | 2021-05-26 | 2021-09-17 | 西南大学 | Chitosan encapsulated hexa-methyl mite acid nano acaricide and preparation method thereof |
| CN115212189A (en) * | 2022-03-30 | 2022-10-21 | 江南大学 | Nano-microsphere for improving oral bioavailability of chitosan oligosaccharide and preparation method thereof |
| CN115154661A (en) * | 2022-07-29 | 2022-10-11 | 广州莱度品牌管理有限公司 | Preparation method of bionic cuticle membrane |
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