CN107266704A - A kind of preparation method of cross linked porous chitosan oligosaccharide - Google Patents
A kind of preparation method of cross linked porous chitosan oligosaccharide Download PDFInfo
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- CN107266704A CN107266704A CN201710568035.9A CN201710568035A CN107266704A CN 107266704 A CN107266704 A CN 107266704A CN 201710568035 A CN201710568035 A CN 201710568035A CN 107266704 A CN107266704 A CN 107266704A
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- chitosan oligosaccharide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/042—Elimination of an organic solid phase
- C08J2201/0422—Elimination of an organic solid phase containing oxygen atoms, e.g. saccharose
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/052—Inducing phase separation by thermal treatment, e.g. cooling a solution
- C08J2201/0524—Inducing phase separation by thermal treatment, e.g. cooling a solution the liquid phase being aqueous
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
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Abstract
The invention discloses a kind of preparation method of cross linked porous chitosan oligosaccharide.Span 80 is taken to be poured into after being dissolved with hexamethylene in three-neck flask; under the protection of inert gas; solution is risen into certain temperature and is stirred continuously; then mixed solution, epoxychloropropane and the sodium hydrate aqueous solution of chitosan oligosaccharide and pore-foaming agent is added dropwise with syringe successively; after being stirred at reflux reaction under certain rotating speed, post processing produces cross linked porous chitosan oligosaccharide.The preparation technology of the present invention is simple, the excellent performance of product, with good loose structure.
Description
Technical field
The invention belongs to chitosan oligosaccharide derivant material preparation field, more particularly to a kind of preparation side of cross linked porous chitosan oligosaccharide
Method.
Background technology
Because chitosan oligosaccharide and its derivative have the performances such as unique biocompatibility, biological degradability and absorption, together
When chitosan oligosaccharide there are many reactive groups, thus can be prepared by chemical reaction or ionic bond effect crosslinking chitosan oligosaccharide with
Lift the mechanical performance and thermal stability of chitosan oligosaccharide.Epoxychloropropane is a kind of conventional crosslinking agent, its can and chitosan oligosaccharide
On amino and hydroxyl reacted.Porous material has very big specific surface area, thus can be used as good adsorption material
Material, the cross linked porous chitosan oligosaccharide for being crosslinked and preparing by epoxychloropropane has been seen in document report.
The content of the invention
In order to solve problem present in background technology, it is an object of the invention to provide a kind of cross linked porous chitosan oligosaccharide
Preparation method.The cross linked porous chitosan oligosaccharide sorbing material of the present invention has more stable pore structure and surface nature, in gas
There is good application prospect in terms of absorption.
Based on above-mentioned purpose, the present invention is adopted the following technical scheme that：
Take span-80 to be poured into after being dissolved with hexamethylene in three-neck flask, under the protection of inert gas, solution is risen to one
Constant temperature degree is simultaneously stirred continuously, be then added dropwise successively with syringe the mixed solution of chitosan oligosaccharide and pore-foaming agent, epoxychloropropane and
Sodium hydrate aqueous solution, is stirred at reflux after reaction 6h, post processing produces cross linked porous chitosan oligosaccharide under certain rotating speed.
The specific reaction equation of preparation process of the present invention is as follows：
The span-80 weighs 5g, is dissolved in 100mL hexamethylenes；The addition of the epoxychloropropane is 4~6mL；
The concentration of the sodium hydrate aqueous solution is 5.0mol/L, and addition is 5.0mL.
In described chitosan oligosaccharide and pore-foaming agent mixed solution, the content concn of chitosan oligosaccharide is 0.17g/mL, and pore-foaming agent contains
Amount concentration is 0.10~0.30g/mL.
Described pore-foaming agent is PEG2000 or PEG4000.
Rotating speed when being stirred at reflux reaction is 500rpm, and the reaction temperature is 40~60 DEG C, and the reaction time is 6h.
Described post-processing approach is：Precipitation is centrifugally separating to obtain, precipitation is washed after three times with 100mL absolute ethyl alcohols, then
20min is soaked with 50mL deionized waters, precipitation liquid nitrogen frozen after centrifuging again, and it is freeze-dried 48h at -45 DEG C.
The beneficial effects of the invention are as follows：
1st, the preparation reaction of cross linked porous chitosan oligosaccharide of the invention uses product in single bath process, course of reaction natural from emulsion
Separate out, it is easy to separating-purifying；
2nd, cross linked porous chitosan oligosaccharide of the invention has preferable surface porosity, can make as good adsorbent
With.
Brief description of the drawings
Fig. 1 is the SEM figures for the cross linked porous chitosan oligosaccharide that the embodiment of the present invention 1 is prepared into embodiment 5.
Embodiment
The present invention is specifically described below by embodiment, is served only for that the present invention is further described, no
It is understood that for limiting the scope of the present invention, the technician in the field can be according to the content of foregoing invention to the present invention
Some nonessential modifications and adaptations are made, are thought within protection scope of the present invention.
Embodiments of the invention are as follows：
Embodiment 1：
The present embodiment comprises the following steps：
3.3177g chitosan oligosaccharides and 4.0021gPEG2000 are weighed, is dissolved in 20mL deionized waters, obtains chitosan oligosaccharide and pore
Agent PEG2000 mixed solution.
5.0798g span-80 are weighed, are poured into after being dissolved with 100mL hexamethylenes in 250mL three-neck flask, in indifferent gas
50 DEG C are warming up under the protection of body and is stirred continuously.
20mL chitosan oligosaccharides and pore-foaming agent PEG2000 mixed solution, 5mL epoxy chloropropionates is added dropwise with syringe successively afterwards
The sodium hydrate aqueous solution of alkane and 5mL 5.0mol/L, after being stirred at reflux 6h under 500rpm rotating speeds, stops reaction.
Precipitation is centrifugally separating to obtain, precipitation is washed after three times with 100mL absolute ethyl alcohols, then is soaked with 50mL deionized waters
20min, precipitation liquid nitrogen frozen after centrifuging again, and 48h is freeze-dried at -45 DEG C, cross linked porous chitosan oligosaccharide is produced,
Shown in its SEM pattern such as Fig. 1 (a), visible surface loose structure is uniformly distributed in figure.Addition per 30mg can adsorb single branch
Ammonia 21.5%, phenol 24.4% in cigarette mainstream flue gas.
Embodiment 2：
The present embodiment comprises the following steps：
3.3588g chitosan oligosaccharides and 4.0507gPEG2000 are weighed, is dissolved in 20mL deionized waters, obtains chitosan oligosaccharide and pore
Agent PEG2000 mixed solution.
5.1357g span-80 are weighed, are poured into after being dissolved with 100mL hexamethylenes in 250mL three-neck flask, in indifferent gas
50 DEG C are warming up under the protection of body and is stirred continuously.
20mL chitosan oligosaccharides and pore-foaming agent PEG2000 mixed solution, 5mL epoxy chloropropionates is added dropwise with syringe successively afterwards
The sodium hydrate aqueous solution of alkane and 5mL 5.0mol/L, after being stirred at reflux 6h under 500rpm rotating speeds, stops reaction.
Precipitation is centrifugally separating to obtain, precipitation is washed after three times with 100mL absolute ethyl alcohols, then is soaked with 50mL deionized waters
20min, precipitation liquid nitrogen frozen after centrifuging again, and 48h is freeze-dried at -45 DEG C, cross linked porous chitosan oligosaccharide is produced,
Shown in its SEM pattern such as Fig. 1 (b), visible surface loose structure is uniformly distributed in figure.Addition per 30mg can adsorb single branch
Ammonia 31.7%, phenol 28.1% in cigarette mainstream flue gas.
Embodiment 3：
The present embodiment comprises the following steps：
3.3564g chitosan oligosaccharides and 4.0563gPEG2000 are weighed, is dissolved in 20mL deionized waters, obtains chitosan oligosaccharide and pore
Agent PEG2000 mixed solution.
5.2421g span-80 are weighed, are poured into after being dissolved with 100mL hexamethylenes in 250mL three-neck flask, in indifferent gas
60 DEG C are warming up under the protection of body and is stirred continuously.
20mL chitosan oligosaccharides and pore-foaming agent PEG2000 mixed solution, 5mL epoxy chloropropionates is added dropwise with syringe successively afterwards
The sodium hydrate aqueous solution of alkane and 5mL 5.0mol/L, after being stirred at reflux 6h under 500rpm rotating speeds, stops reaction.
Precipitation is centrifugally separating to obtain, precipitation is washed after three times with 100mL absolute ethyl alcohols, then is soaked with 50mL deionized waters
20min, precipitation liquid nitrogen frozen after centrifuging again, and 48h is freeze-dried at -45 DEG C, cross linked porous chitosan oligosaccharide is produced,
Shown in its SEM pattern such as Fig. 1 (c), visible surface loose structure is uniformly distributed in figure.Addition per 30mg can adsorb single branch
Ammonia 17.1%, phenol 15.9% in cigarette mainstream flue gas.
Embodiment 4：
The present embodiment comprises the following steps：
3.3891g chitosan oligosaccharides and 6.0347gPEG2000 are weighed, is dissolved in 20mL deionized waters, obtains chitosan oligosaccharide and pore
Agent PEG2000 mixed solution.
5.0903g span-80 are weighed, are poured into after being dissolved with 100mL hexamethylenes in 250mL three-neck flask, in indifferent gas
50 DEG C are warming up under the protection of body and is stirred continuously.
20mL chitosan oligosaccharides and pore-foaming agent PEG2000 mixed solution, 5mL epoxy chloropropionates is added dropwise with syringe successively afterwards
The sodium hydrate aqueous solution of alkane and 5mL 5.0mol/L, after being stirred at reflux 6h under 500rpm rotating speeds, stops reaction.
Precipitation is centrifugally separating to obtain, precipitation is washed after three times with 100mL absolute ethyl alcohols, then is soaked with 50mL deionized waters
20min, precipitation liquid nitrogen frozen after centrifuging again, and 48h is freeze-dried at -45 DEG C, cross linked porous chitosan oligosaccharide is produced,
Shown in its SEM pattern such as Fig. 1 (d), visible surface loose structure is uniformly distributed in figure.
Embodiment 5：
The present embodiment comprises the following steps：
3.3472g chitosan oligosaccharides and 4.0213gPEG4000 are weighed, is dissolved in 20mL deionized waters, obtains chitosan oligosaccharide and pore
Agent PEG2000 mixed solution.
5.1745g span-80 are weighed, are poured into after being dissolved with 100mL hexamethylenes in 250mL three-neck flask, in indifferent gas
50 DEG C are warming up under the protection of body and is stirred continuously.
20mL chitosan oligosaccharides and pore-foaming agent PEG2000 mixed solution, 5mL epoxy chloropropionates is added dropwise with syringe successively afterwards
The sodium hydrate aqueous solution of alkane and 5mL 5.0mol/L, after being stirred at reflux 6h under 500rpm rotating speeds, stops reaction.
Precipitation is centrifugally separating to obtain, precipitation is washed after three times with 100mL absolute ethyl alcohols, then is soaked with 50mL deionized waters
20min, precipitation liquid nitrogen frozen after centrifuging again, and 48h is freeze-dried at -45 DEG C, cross linked porous chitosan oligosaccharide is produced,
Shown in its SEM pattern such as Fig. 1 (e), visible surface loose structure is uniformly distributed in figure.
Claims (6)
1. a kind of preparation method of cross linked porous chitosan oligosaccharide, it is characterised in that comprise the following steps：
Take span-80 to be poured into after being dissolved with hexamethylene in three-neck flask, under the protection of inert gas, solution is risen into a constant temperature
Spend and be stirred continuously, mixed solution, epoxychloropropane and the hydrogen-oxygen of chitosan oligosaccharide and pore-foaming agent is then added dropwise with syringe successively
Change sodium water solution, be stirred at reflux under certain rotating speed after reaction 6h, post processing produces cross linked porous chitosan oligosaccharide.
2. a kind of preparation method of cross linked porous chitosan oligosaccharide according to claim 1, it is characterised in that：
The span-80 weighs 5g, is dissolved in 100mL hexamethylenes；The addition of the epoxychloropropane is 4~6mL；It is described
The concentration of sodium hydrate aqueous solution is 5.0mol/L, and addition is 5.0mL.
3. a kind of preparation method of cross linked porous chitosan oligosaccharide according to claim 1, it is characterised in that：
In described chitosan oligosaccharide and pore-foaming agent mixed solution, the content concn of chitosan oligosaccharide is 0.17g/mL, and the content of pore-foaming agent is dense
Spend for 0.10~0.30g/mL.
4. a kind of preparation method of cross linked porous chitosan oligosaccharide according to claim 1 or 3, it is characterised in that：Described cause
Hole agent is PEG2000 or PEG4000.
5. a kind of preparation method of cross linked porous chitosan oligosaccharide according to claim 1, it is characterised in that：
Rotating speed when being stirred at reflux reaction is 500rpm, and the reaction temperature is 40~60 DEG C.
6. a kind of preparation method of cross linked porous chitosan oligosaccharide according to claim 1, it is characterised in that：
Described post-processing approach is：Precipitation is centrifugally separating to obtain, precipitation is washed after three times with absolute ethyl alcohol, then uses deionized water
Immersion, precipitation liquid nitrogen frozen after centrifuging again, and be freeze-dried at -45 DEG C.
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| CN201710568035.9A CN107266704A (en) | 2017-07-12 | 2017-07-12 | A kind of preparation method of cross linked porous chitosan oligosaccharide |
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| CN201710568035.9A CN107266704A (en) | 2017-07-12 | 2017-07-12 | A kind of preparation method of cross linked porous chitosan oligosaccharide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440773A (en) * | 2018-04-28 | 2018-08-24 | 常州大学 | A kind of double primary amine cross-linked gels of chitosan oligosaccharide |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102443186A (en) * | 2011-09-30 | 2012-05-09 | 浙江省海洋开发研究院 | Preparation method of epoxy chloropropane cross-linked chitosan microspheres |
| CN103341172A (en) * | 2013-05-07 | 2013-10-09 | 中国科学院过程工程研究所 | Dual-hole polysaccharide microspheres, preparation method and purpose thereof |
-
2017
- 2017-07-12 CN CN201710568035.9A patent/CN107266704A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102443186A (en) * | 2011-09-30 | 2012-05-09 | 浙江省海洋开发研究院 | Preparation method of epoxy chloropropane cross-linked chitosan microspheres |
| CN103341172A (en) * | 2013-05-07 | 2013-10-09 | 中国科学院过程工程研究所 | Dual-hole polysaccharide microspheres, preparation method and purpose thereof |
Non-Patent Citations (1)
| Title |
|---|
| 王俊骅: ""壳寡糖的化学改性及其对氨和苯酚吸附性能的研究"", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440773A (en) * | 2018-04-28 | 2018-08-24 | 常州大学 | A kind of double primary amine cross-linked gels of chitosan oligosaccharide |
| CN108440773B (en) * | 2018-04-28 | 2021-01-29 | 常州大学 | Chitosan oligosaccharide diprimary amine crosslinked gel |
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