CN101810863A - Preparation method of carboxymethyl chitosan quaternary ammonium salt/organic rectorite nano composite material and application thereof - Google Patents
Preparation method of carboxymethyl chitosan quaternary ammonium salt/organic rectorite nano composite material and application thereof Download PDFInfo
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- CN101810863A CN101810863A CN200910213896A CN200910213896A CN101810863A CN 101810863 A CN101810863 A CN 101810863A CN 200910213896 A CN200910213896 A CN 200910213896A CN 200910213896 A CN200910213896 A CN 200910213896A CN 101810863 A CN101810863 A CN 101810863A
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Abstract
The invention provides a preparation method of a carboxymethyl chitosan quaternary ammonium salt/organic rectorite nano composite material and an application thereof. The carboxymethyl chitosan quaternary ammonium salt/organic rectorite nano composite material comprises the basis components of carboxymethyl chitosan quaternary ammonium salt and organic rectorite, and is generated by intercalating the carboxymethyl chitosan quaternary ammonium salt layer between the organic rectorite layers, wherein the distance between the intercalated organic rectorite layers is 4.2-4.72 nm. The preparation method comprises the following steps: dropwise adding the carboxymethyl chitosan quaternary ammonium salt solution of a certain concentration to the organic rectorite aqueous suspension under the condition of stirring at 70-80 DEG C, and then freezing and drying to obtain the nano composite material carboxymethyl chitosan quaternary ammonium salt/organic rectorite. The nano composite material can be used as a drug carrier, has the advantages of both the carboxymethyl chitosan quaternary ammonium salt and the organic rectorite, the drug control-release capability of the nano composite material is superior to that of the single carboxymethyl chitosan quaternary ammonium salt, and the heat resistance of the nano composite material is also significantly improved compared with that of the carboxymethyl chitosan quaternary ammonium salt.
Description
Technical field
The present invention relates to a kind of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material that is used as pharmaceutical carrier and preparation method thereof.
Background technology
Carboxymethyl chitosan quaternary ammonium salt is an amphiphilic polymers of introducing carboxymethyl and quaternary ammonium salt group on the chitosan molecule chain simultaneously, it has and the similar structure of biopolymers such as protein, nucleic acid, have higher biocompatibility, it has caused people's extensive concern at biomedical sector.Prior art studies show that it has medicine controlled releasing ability preferably, but not very good to the envelop rate and the slow release effect of medicine.Layer silicate mineral has adhesion property, it can be submicron dispersion in aqueous solution, cheap, specific surface area is big, high adsorption capacity and good biocompatibility, adding it can be by the ability of intercalation, and is widely used in new drug sustained release system---in the nano composite polymer/laminated silicate material.Therefore, the compound preparation nano composite material of carboxymethyl chitosan quaternary ammonium salt and organic rectorite intercalation can further improve the medicine controlled releasing performance of carrier, the more lasting medicine that discharges lentamente, and the new approach of development developing for medicine has broad application prospects.Nano composite material that carboxymethyl chitosan quaternary ammonium salt and organic rectorite are combined does not appear in the prior art at present as yet.
Summary of the invention
The objective of the invention is to overcome the prior art above shortcomings, the preparation method and the application thereof of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material are provided, this material can combine carboxymethyl chitosan quaternary ammonium salt with the advantage of rectorite, be more suitable in controlled drug delivery system.
The technical solution adopted in the present invention is: carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is made up of carboxymethyl chitosan quaternary ammonium salt and organic rectorite, wherein carboxymethyl chitosan quaternary ammonium salt accounts for that total weight percent is 50～90%, to account for total weight percent be 10～50% to organic rectorite, the carboxymethyl chitosan quaternary ammonium salt intercalation is entered the organic rectorite interlayer and is generated by the solution intercalation method.
The molecular weight of the carboxymethyl chitosan quaternary ammonium salt that above-mentioned composite is used is 3.5 * 10
5～4.1 * 10
5, degree of substitution by carboxymethyl is 50～70%, the quaternary ammonium salt substitution value is 75～90%.Organic rectorite obtains natural calcio rectorite through the cetyl trimethyl ammonium bromide modification.The interlamellar spacing of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is between 4.2～4.72nm.
The preparation method of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material provided by the invention may further comprise the steps: the aqueous solution that carboxymethyl chitosan quaternary ammonium salt is made into 0.1～0.25g/ml, be added drop-wise in 1～2g/ml organic rectorite suspension, behind 70～80 ℃ of reaction 1～2d, again 0.5～1g/ml carboxymethyl chitosan quaternary ammonium salt aqueous solution is added.In this method, earlier with behind carboxymethyl chitosan quaternary ammonium salt weak solution and the organic rectorite reaction 1～2d, organic rectorite interlayer microenvironment is changed, and the carboxymethyl chitosan quaternary ammonium salt concentrated solution intercalation that adds once more for the back provides driving force, and forms nano composite material.Continue to stir 1～2d, lyophilization promptly gets carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.
Above-mentioned carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is as the application of pharmaceutical carrier.
Above-mentioned application specifically comprises: be 12 by weight percentage: (1～2): the ratio of (2～3) weighs sodium alginate, calcium chloride and carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.Sodium alginate is made 0.5～1.5mg/ml aqueous solution, be added dropwise in the calcium chloride water of 0.3～0.6mg/ml, stir 0.5～1h, and then be added drop-wise to the bag be loaded with bovine serum albumin, concentration is in 0.5～1.5mg/ml carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material aqueous solution, be cross-linked into nanoparticle, high speed centrifugation separates, lyophilization, promptly obtain carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano compound particle, its particle diameter is between 310～485nm.
Compared with prior art, the present invention has following advantage and effect:
Carboxymethyl chitosan quaternary ammonium salt is a kind of new type water-solubility derivant of chitosan, because of its good water solublity, thickening property, dispersibility, emulsibility, moisture retention, can form variforms such as film, gel, sponge, microsphere and have Amphiphatic high polymer polyelectrolyte characteristic, in fields such as food, cosmetics, biological medicine, important use be arranged.Its intercalation is entered behind the organic rectorite interlayer and the nano composite material that obtains can form new controlled drug delivery system in conjunction with both advantages, this controlled release system is compared with single carboxymethyl chitosan quaternary ammonium salt, can discharge medicine lentamente more lastingly.Simultaneously, because organic rectorite high-fire resistance and the homodisperse in the carboxymethyl chitosan quaternary ammonium salt matrix, the heat resistance of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material improves a lot than carboxymethyl chitosan quaternary ammonium salt, has widened the scope of application of this controlled drug delivery system.
The specific embodiment
Among the embodiment, organic rectorite is obtained through the cetyl trimethyl ammonium bromide modification by natural calcio rectorite, its preparation method is identical with preparation method among the patent ZL200610125560.5 that has authorized: with 4g rectorite adding distil water 20ml, behind the homodisperse, high-speed stirred 30min, obtain stable rectorite suspension, place 24h.The 5g cetyl trimethyl ammonium bromide is made into 2% aqueous solution drops in 90 ℃ the rectorite suspension, constant temperature 5h, sucking filtration, and repeatedly wash with distilled water, until detecting no bromide ion, under 90 ℃, be dried to constant weight with silver nitrate, must organic rectorite.
Embodiment 1: (weight average molecular weight is 4.1 * 10 with the 0.05g carboxymethyl chitosan quaternary ammonium salt
5Degree of substitution by carboxymethyl is 70%, the quaternary ammonium salt substitution value is 75%) be made into the aqueous solution of 0.1g/ml, be added drop-wise in the 0.1g 1g/ml organic rectorite suspension, behind 80 ℃ of reaction 1.5d, 0.05g 0.5g/ml carboxymethyl chitosan quaternary ammonium salt aqueous solution is added again, continue to stir 1d, lyophilization promptly gets carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.Carboxymethyl chitosan quaternary ammonium salt.The shared total weight percent of each component of this composite is respectively carboxymethyl chitosan quaternary ammonium salt 50%, organic rectorite 50%.The interlamellar spacing of rectorite is 4.62nm in the composite.
Sodium alginate is made the 0.5mg/ml aqueous solution, be added dropwise in the calcium chloride water of 0.3mg/ml, stir 0.5h, and then be added drop-wise to the bag be loaded with bovine serum albumin, concentration is in 0.5mg/ml carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material aqueous solution, be cross-linked into nanoparticle, its particle diameter is 485nm.Sodium alginate in this nanoparticle: calcium chloride: the percentage by weight of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is 12: 1: 2.This nanoparticle is 75% to the envelop rate of bovine serum albumin, in simulated gastric fluid, and six days accumulation slow release 20%, in simulated intestinal fluid, eight days accumulation slow release 45%.
Embodiment 2: (weight average molecular weight is 3.5 * 10 with the 0.1g carboxymethyl chitosan quaternary ammonium salt
5Degree of substitution by carboxymethyl is 50%, the quaternary ammonium salt substitution value is 90%) be made into the aqueous solution of 0.15g/ml, be added drop-wise in the 0.1g 1.5g/ml organic rectorite suspension, behind 75 ℃ of reaction 1d, 0.1g 0.75g/ml carboxymethyl chitosan quaternary ammonium salt aqueous solution is added again, continue to stir 1.5d, lyophilization promptly gets carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.The shared total weight percent of each component of this composite is respectively carboxymethyl chitosan quaternary ammonium salt 66.7%, organic rectorite 33.3%.The interlamellar spacing of rectorite is 4.72nm in the composite.
Sodium alginate is made the 0.8mg/ml aqueous solution, be added dropwise in the calcium chloride water of 0.5mg/ml, stir 0.75h, and then be added drop-wise to the bag be loaded with bovine serum albumin, concentration is in 1.0mg/ml carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material aqueous solution, be cross-linked into nanoparticle, its particle diameter is 424nm.Sodium alginate in this nanoparticle: calcium chloride: the percentage by weight of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is 12: 1.5: 2.This nanoparticle is 82% to the envelop rate of bovine serum albumin, in simulated gastric fluid, and six days accumulation slow release 15%, in simulated intestinal fluid, eight days accumulation slow release 41%.
Embodiment 3: (weight average molecular weight is 3.8 * 10 with the 0.1g carboxymethyl chitosan quaternary ammonium salt
5Degree of substitution by carboxymethyl is 60%, the quaternary ammonium salt substitution value is 85%) be made into the aqueous solution of 0.2g/ml, be added drop-wise in the 0.1g 1.5g/ml organic rectorite suspension, behind 80 ℃ of reaction 2d, 0.3g 1g/ml carboxymethyl chitosan quaternary ammonium salt aqueous solution is added again, continue to stir 1.5d, lyophilization promptly gets carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.The shared total weight percent of each component of this composite is respectively carboxymethyl chitosan quaternary ammonium salt 80%, organic rectorite 20%.The interlamellar spacing of rectorite is 4.41nm in the composite.
Sodium alginate is made the 1.0mg/ml aqueous solution, be added dropwise in the calcium chloride water of 0.5mg/ml, stir 1h, and then be added drop-wise to the bag be loaded with bovine serum albumin, concentration is in 1.2mg/ml carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material aqueous solution, be cross-linked into nanoparticle, its particle diameter is 385nm.Sodium alginate in this nanoparticle: calcium chloride: the percentage by weight of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is 12: 2: 2.This nanoparticle is 85% to the envelop rate of bovine serum albumin, in simulated gastric fluid, and six days accumulation slow release 12%, in simulated intestinal fluid, the slow sample 37% of accumulation in eight days.
Embodiment 4: (weight average molecular weight is 3.6 * 10 with the 0.2g carboxymethyl chitosan quaternary ammonium salt
5Degree of substitution by carboxymethyl is 55%, the quaternary ammonium salt substitution value is 80%) be made into the aqueous solution of 0.25g/ml, be added drop-wise in the 0.1g 2g/ml organic rectorite suspension, behind 80 ℃ of reaction 2d, 0.7g 1g/ml carboxymethyl chitosan quaternary ammonium salt aqueous solution is added again, continue to stir 2d, lyophilization promptly gets carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.The shared total weight percent of each component of this composite is respectively carboxymethyl chitosan quaternary ammonium salt 90%, organic rectorite 10%.The interlamellar spacing of rectorite is 4.32nm in the composite.
Sodium alginate is made the 1.5mg/ml aqueous solution, be added dropwise in the calcium chloride water of 0.6mg/ml, stir 1h, and then be added drop-wise to the bag be loaded with bovine serum albumin, concentration is in 1.5mg/ml carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material aqueous solution, be cross-linked into nanoparticle, its particle diameter is 310nm.Sodium alginate in this nanoparticle: calcium chloride: the percentage by weight of carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is 12: 2: 3.This nanoparticle is 90% to the envelop rate of bovine serum albumin, in simulated gastric fluid, and six days accumulation slow release 8%, in simulated intestinal fluid, eight days accumulation slow release 29%.
Claims (8)
1. carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material, it is characterized in that the carboxymethyl chitosan quaternary ammonium salt intercalation being obtained in the organic rectorite interlayer by the solution intercalation method, the percentage by weight of composite consists of: carboxymethyl chitosan quaternary ammonium salt 50～90%, organic rectorite 10～50%.
2. carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material according to claim 1, the interlamellar spacing that it is characterized in that carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is 4.2～4.72nm.
3. carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material according to claim 1 is characterized in that: the weight average molecular weight of used carboxymethyl chitosan quaternary ammonium salt is 3.5 * 10
5～4.1 * 10
5, degree of substitution by carboxymethyl is 50～70%, the quaternary ammonium salt substitution value is 75～90%.
4. according to each described carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material of claim 1～3, it is characterized in that described organic rectorite is obtained through the cetyl trimethyl ammonium bromide modification by natural calcio rectorite.
5. the preparation method of the described carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material of claim 1, it is characterized in that comprising the steps: carboxymethyl chitosan quaternary ammonium salt is made into the aqueous solution of 0.1～0.25g/ml, be added drop-wise in 1～2g/ml organic rectorite suspension, behind 70～80 ℃ of reaction 1～2d, again 0.5～1g/ml carboxymethyl chitosan quaternary ammonium salt aqueous solution is added, continue to stir 1～2d, lyophilization promptly gets carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material.
6. described carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is as the application of pharmaceutical carrier.
7. application according to claim 6, it is characterized in that: sodium alginate is made 0.5～1.5mg/ml aqueous solution, be added dropwise in the calcium chloride water of 0.3～0.6mg/ml, stir 0.5～1h, and then be added drop-wise to the bag be loaded with bovine serum albumin, concentration is in 0.5～1.5mg/ml carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material aqueous solution, be cross-linked into nanoparticle, centrifugalize, lyophilization, obtain carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano compound particle, its particle diameter is between 310～485nm.
8. application according to claim 7 is characterized in that: the weight ratio of sodium alginate, calcium chloride and carboxymethyl chitosan quaternary ammonium salt/salt/organic rectorite nano composite material is 12: (1～2): (2～3).
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Cited By (7)
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| CN102241838A (en) * | 2011-06-30 | 2011-11-16 | 华南理工大学 | Stripping-off type carboxymethylchitosan quaternary ammonium salt/rectorite nano composite material and preparation method thereof |
| CN102504352A (en) * | 2011-11-03 | 2012-06-20 | 华南理工大学 | Carboxymethyl chitosan oligosaccharide quaternary ammonium salt/rectorite nanometer composite material and preparation method and application thereof |
| CN103289136A (en) * | 2013-06-21 | 2013-09-11 | 北京邦明生物技术研究院 | Sodium alginate and rectorite nanometer composite material preparation method |
| CN103319750A (en) * | 2013-06-13 | 2013-09-25 | 华南理工大学 | Carboxymethyl chitosan quaternary ammonium salt/modified zirconium phosphate nanometer composite material |
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| CN108273475A (en) * | 2018-02-22 | 2018-07-13 | 湖北钟祥名流累托石开发有限公司 | The purposes of long chain alkyl ammonium salt/rectorite compound material, mycotoxin adsorption material and preparation method thereof |
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2009
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241838A (en) * | 2011-06-30 | 2011-11-16 | 华南理工大学 | Stripping-off type carboxymethylchitosan quaternary ammonium salt/rectorite nano composite material and preparation method thereof |
| CN102504352A (en) * | 2011-11-03 | 2012-06-20 | 华南理工大学 | Carboxymethyl chitosan oligosaccharide quaternary ammonium salt/rectorite nanometer composite material and preparation method and application thereof |
| CN102504352B (en) * | 2011-11-03 | 2013-12-25 | 华南理工大学 | Carboxymethyl chitosan oligosaccharide quaternary ammonium salt/rectorite nanometer composite material and preparation method and application thereof |
| CN103319750A (en) * | 2013-06-13 | 2013-09-25 | 华南理工大学 | Carboxymethyl chitosan quaternary ammonium salt/modified zirconium phosphate nanometer composite material |
| CN103319750B (en) * | 2013-06-13 | 2016-10-05 | 华南理工大学 | A kind of carboxymethyl chitosan quaternary ammonium salt/modified zirconium phosphate nano composite material |
| CN103289136A (en) * | 2013-06-21 | 2013-09-11 | 北京邦明生物技术研究院 | Sodium alginate and rectorite nanometer composite material preparation method |
| CN108159480A (en) * | 2017-12-14 | 2018-06-15 | 华南理工大学 | A kind of preparation method and application of injectable polysaccharide clay plural gel |
| CN108159480B (en) * | 2017-12-14 | 2021-08-10 | 华南理工大学 | Preparation method and application of injectable polysaccharide clay composite gel |
| CN108273475A (en) * | 2018-02-22 | 2018-07-13 | 湖北钟祥名流累托石开发有限公司 | The purposes of long chain alkyl ammonium salt/rectorite compound material, mycotoxin adsorption material and preparation method thereof |
| CN108273475B (en) * | 2018-02-22 | 2021-04-06 | 湖北钟祥名流累托石开发有限公司 | Application of long-chain alkyl quaternary ammonium salt/rectorite composite material, mycotoxin adsorption material and preparation method thereof |
| CN109646703A (en) * | 2018-12-21 | 2019-04-19 | 华山科技股份有限公司 | A kind of nano-cellulose composite antibacterial material and the preparation method and application thereof |
| CN109646703B (en) * | 2018-12-21 | 2022-02-15 | 华山科技股份有限公司 | Nano-cellulose composite antibacterial material and preparation method and application thereof |
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