CN110483845A - A kind of graphene oxide/chitosan oligosaccharide composite crosslinking gel - Google Patents
A kind of graphene oxide/chitosan oligosaccharide composite crosslinking gel Download PDFInfo
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- CN110483845A CN110483845A CN201910592004.6A CN201910592004A CN110483845A CN 110483845 A CN110483845 A CN 110483845A CN 201910592004 A CN201910592004 A CN 201910592004A CN 110483845 A CN110483845 A CN 110483845A
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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
- 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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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
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- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/042—Graphene or derivatives, e.g. graphene oxides
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Abstract
The present invention relates to a kind of graphene oxide/chitosan oligosaccharide composite crosslinking gels.Using the chitosan oligosaccharide of good water solubility as raw material, it is crosslinked it with graphene oxide using double primary amine.Using the lamellar structure of graphene oxide, effectively expand the specific surface area of gel.Reaction condition of the present invention is mild, simple process, has superior performance at heavy metal ion adsorbed aspect.
Description
Technical field
The invention belongs to natural macromolecule modification fields, and in particular to a kind of graphene oxide/chitosan oligosaccharide composite crosslinking is solidifying
Glue.
Background technique
Graphene oxide (Graphene Oxide) is generally aoxidized through strong acid by graphite and is obtained.After oxidation processes, oxygen
Graphite still keeps the layer structure of graphite, but many oxygroup functional groups are introduced on each layer of graphene monolithic.These
The introducing of oxygroup functional group is so that single graphene-structured becomes extremely complex.Graphene oxide has very big specific surface
Product, theoretical specific surface area have reached 2630m2/g。
As the representative of biological material, chitosan has been widely used in medical and health, environmental protection, food work
Among the numerous areas such as industry, light textile chemical industry and agricultural.Chitosan oligosaccharide is to be carried out by chitosan by physics, chemistry or biological method
It degrades obtained low-molecular weight chitoglycan.Compared with chitosan, chitosan oligosaccharide has more excellent dissolubility and bioactivity.
It is modified difficult due to chitosan poorly water-soluble, and obtain that macromolecule is mostly powdered, thus using the chitosan oligosaccharide of good water solubility into
The three-dimensional cross-linked high molecular synthesis of row is of great significance.Largely free amino and hydroxyl are dispersed on the strand of chitosan oligosaccharide
Base, both more active reactive groups, can occur O- is acylated, N- is acylated, etherificate, N- alkylation, graft copolymerization with
And the reaction such as crosslinking.Therefore, these chemical property that can use chitosan oligosaccharide are modified it, introduce on macromolecular chain each
The different group of kind achievees the effect that improve its physicochemical property and assigns its more feature and function, so that chitosan oligosaccharide be answered
Among different fields.
Summary of the invention
It is an object of the invention to use the chitosan oligosaccharide of the graphene oxide with lamellar structure and good water solubility as raw material,
By introducing double primary amine of active group, crosslinked reaction obtains large specific surface area, the three-dimensional gel structure haveing excellent performance.
Graphene oxide/chitosan oligosaccharide composite crosslinking gel, wherein the molecular weight of chitosan oligosaccharide is 500-5000Da, double primary amine tools
Just like flowering structure:
Formula 1
Wherein, m is the integer of 0-100, and n is the integer of 0-100, and m, n are not 0 simultaneously.X, Y are same or different, represent-
CH2- ,-NH- ,-O- ,-S- ,-CO- ,-CH(R1) one or more of the unit that forms is connected with random order；R1 represents ammonia
It is base, hydroxyl, sulfydryl, carboxyl, aldehyde radical, methoxyl group, nitro, halogen atom, non-substituted or by one or more amino, hydroxyl, mercapto
The alkyl for the C1-C50 that base, carboxyl, aldehyde radical, methoxyl group, nitro, halogen atom replace.
Graphene oxide of the present invention/chitosan oligosaccharide composite crosslinking gel, preparation method are as follows:
(1) chitosan oligosaccharide is dissolved in the water, epoxychloropropane is added, constant temperature stirring is extracted with organic solvent after reaction
It takes, synthetic solvent 1.Wherein the molar ratio of epoxychloropropane and amino in chitosan oligosaccharide is (0.4-3): 1, reaction temperature 0-100
DEG C, reaction time 0.1-48h.
(2) it is extracted with organic solvent, phase of fetching water.Wherein organic solvent be ethers, esters, benzene class, chlorinated solvents, preferably
Methylene chloride, chloroform, carbon tetrachloride, ether, ethyl acetate, any one in trichloro ethylene.
(3) graphene oxide being dispersed in water, gained dispersion liquid instills in double primary amine, and condensing agent is added, and constant temperature stirs,
Synthetic solvent 2.Wherein condensing agent is N, the double primary amine (DIC) of N'- diisopropylcarbodiimide, I-hydroxybenzotriazole (HOBT),
4-dimethylaminopyridine (DMAP), carbodiimides (EDCI), 2- (7- aoxidizes benzotriazole)-N, N, N', N'- tetramethylurea
Hexafluorophosphate (HATU), dicyclohexylcarbodiimide (DCC)/n-hydroxysuccinimide (NHS), 1- (3- dimethylamino third
Base) any one or more in -3- ethyl-carbodiimide hydrochloride (EDC)/n-hydroxysuccinimide (NHS).
(4) solution 1 is uniformly mixed with solution 2, constant temperature stirring.The molar ratio of double primary amine and amino in chitosan oligosaccharide is
(0.4-2): 2, the mass ratio of graphene oxide and chitosan oligosaccharide is (0.01-20): 1000, reaction temperature is 0-100 DEG C, when reaction
Between be -7 days 1 day.
Compared with the prior art, it is the advantages of technical solution of the present invention:
(1) graphene oxide/chitosan oligosaccharide composite crosslinking gel, simple synthetic method, condition are easily controllable.
(2) graphene oxide/chitosan oligosaccharide composite crosslinking gel large specific surface area, density is small, and active site is more.
(3) graphene oxide/chitosan oligosaccharide composite crosslinking gel has good mechanical performance.
Detailed description of the invention
Fig. 1: for the graphene oxide/chitosan oligosaccharide composite crosslinking gel Fourier transformation prepared in the embodiment of the present invention 1
Infrared (FT-IR) spectrogram.
Fig. 2: to prepare graphene oxide/chitosan oligosaccharide composite crosslinking gel X-ray diffraction in the embodiment of the present invention 1
(XRD) spectrogram.
Specific embodiment
Embodiment 1
(1) 5g chitosan oligosaccharide is weighed, 40ml water is added, dissolves it sufficiently.
(2) 1.435g epoxychloropropane is weighed, is added in chitosan oligosaccharide solution, 40 DEG C of constant temperature stir, and mixing speed is
150rpm, reaction for 24 hours, are extracted with ether after reaction, obtain solution 1.
(3) 2mg graphene oxide is weighed to be dispersed in 1ml water.
(4) 1.76g tetraethylenepentamine is added in graphene oxide dispersion, it is sub- that 1.43g N- hydroxysuccinimidyl acyl is added
Amine, 2.382g 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride, 20 DEG C of constant temperature stirrings, mixing speed
150rmp reacts 6h, obtains solution 2.
(5) mixed solution 1 and solution 2, mixing speed 150rmp, 20 DEG C of constant temperature stirrings react 1 day, obtain oxidation stone
Black alkene/chitosan oligosaccharide composite crosslinking gel.
Embodiment 2
(1) 5g chitosan oligosaccharide is weighed, 40ml water is added, dissolves it sufficiently.
(2) 1.435g epoxychloropropane is weighed, is added in chitosan oligosaccharide solution, 80 DEG C of constant temperature stir, and mixing speed is
150rpm reacts 12h, is extracted after reaction with ether, obtain solution 1.
(3) 2mg graphene oxide is weighed to be dispersed in 1ml water.
(4) 1.76g tetraethylenepentamine is added in graphene oxide dispersion, it is sub- that 1.43g N- hydroxysuccinimidyl acyl is added
Amine, 2.382g 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride, 20 DEG C of constant temperature stirrings, mixing speed
150rmp reacts 6h, obtains solution 2.
(5) mixed solution 1 and solution 2, mixing speed 150rmp, 25 DEG C of constant temperature stirrings react 3 days, obtain oxidation stone
Black alkene/chitosan oligosaccharide composite crosslinking gel.
Embodiment 3
(1) 5g chitosan oligosaccharide is weighed, 40ml water is added, dissolves it sufficiently.
(2) 1.435g epoxychloropropane is weighed, is added in chitosan oligosaccharide solution, 40 DEG C of constant temperature stir, and mixing speed is
150rpm, reaction for 24 hours, are extracted with ether after reaction, obtain solution 1.
(3) 10mg graphene oxide is weighed to be dispersed in 1ml water.
(4) 2.11g tetraethylenepentamine is added in graphene oxide dispersion, dicyclohexylcarbodiimide is added in 2.56g,
1.43g n-hydroxysuccinimide, 20 DEG C of constant temperature stirrings, mixing speed 150rmp react 6h, obtain solution 2.
(5) mixed solution 1 and solution 2, mixing speed 150rmp, 25 DEG C of constant temperature stirrings react 5 days, obtain oxidation stone
Black alkene/chitosan oligosaccharide composite crosslinking gel.
Embodiment 4
(1) 5g chitosan oligosaccharide is weighed, 30ml water is added, dissolves it sufficiently.
(2) 1.435g epoxychloropropane is weighed, is added in chitosan oligosaccharide solution, 40 DEG C of constant temperature stir, and mixing speed is
150rpm, reaction for 24 hours, are extracted with dichloromethane after reaction, obtain solution 1.
(3) 2mg graphene oxide is weighed to be dispersed in 1ml water.
(4) 3.52g triethylene tetramine is added in graphene oxide dispersion, 2.56g dicyclohexylcarbodiimide is added,
1.43g n-hydroxysuccinimide, 20 DEG C of constant temperature stirrings, mixing speed 150rmp react 6h, obtain solution 2.
(5) mixed solution 1 and solution 2, mixing speed 150rmp, 25 DEG C of constant temperature stirrings react 3 days, obtain oxidation stone
Black alkene/chitosan oligosaccharide composite crosslinking gel.
Claims (8)
1. a kind of graphene oxide/chitosan oligosaccharide composite crosslinking gel, it is characterised in that the gel process for preparing according to the following steps into:
Chitosan oligosaccharide is dissolved in the water, epoxychloropropane is added, constant temperature stirring is extracted with organic solvent after reaction, synthesized
Solution 1；Graphene oxide is dispersed in water, gained dispersion liquid instills in double primary amine, and condensing agent, constant temperature stirring, synthesis is added
Solution 2；Solution 1 is uniformly mixed with solution 2, constant temperature stirring.
2. the black alkene crosslinking/chitosan oligosaccharide composite crosslinking gel of oxidation according to claim 1, it is characterised in that the chitosan oligosaccharide
Molecular weight be 500-5000Da.
3. graphene oxide according to claim 1/chitosan oligosaccharide composite crosslinking gel, it is characterised in that double primary amine have such as
Flowering structure formula:
Formula 1
Wherein, m is the integer of 0-100, and n is the integer of 0-100, and m, n are not 0 simultaneously；X, Y are same or different, represent-
CH2- ,-NH- ,-O- ,-S- ,-CO- ,-CH(R1) one or more of the unit that forms is connected with random order；R1 represents ammonia
It is base, hydroxyl, sulfydryl, carboxyl, aldehyde radical, methoxyl group, nitro, halogen atom, non-substituted or by one or more amino, hydroxyl, mercapto
The alkyl for the C1-C50 that base, carboxyl, aldehyde radical, methoxyl group, nitro, halogen atom replace.
4. graphene oxide according to claim 1/chitosan oligosaccharide composite crosslinking gel, it is characterised in that: in the synthesis of solution 1
The molar ratio of amino is (0.4-3) in epoxychloropropane and chitosan oligosaccharide: 1, reaction temperature is 0-100 DEG C, reaction time 0.1-
48h is sufficiently stirred.
5. graphene according to claim 1/chitosan oligosaccharide composite crosslinking gel, it is characterised in that: extractant is ethers, ester
Class, benzene class, chlorinated solvents, preferably methylene chloride, chloroform, carbon tetrachloride, ether, ethyl acetate, in trichloro ethylene
Any one.
6. graphene oxide according to claim 1/chitosan oligosaccharide composite crosslinking gel, it is characterised in that: condensing agent N,
The double primary amine (DIC) of N'- diisopropylcarbodiimide, I-hydroxybenzotriazole (HOBT), 4-dimethylaminopyridine (DMAP), carbonization
Diimine (EDCI), 2- (7- aoxidizes benzotriazole)-N, N, N', N'- tetramethylurea hexafluorophosphate (HATU), dicyclohexyl
Carbodiimide (DCC)/n-hydroxysuccinimide (NHS), 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride
(EDC) any one or more in/n-hydroxysuccinimide (NHS).
7. graphene oxide according to claim 1/chitosan oligosaccharide composite crosslinking gel, it is characterised in that: in the synthesis of solution 2
The molar ratio of amino is (0.4-2) in double primary amine and chitosan oligosaccharide: 2, the mass ratio of graphene oxide and chitosan oligosaccharide is (0.01-
20): 1000.
8. graphene oxide according to claim 1/chitosan oligosaccharide composite crosslinking gel, it is characterised in that: solution 1 and solution
2 temperature being mixed are 0-100 DEG C, and the reaction time is -7 days 1 day.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114736399A (en) * | 2022-05-20 | 2022-07-12 | 常州大学 | High-elasticity carboxymethyl chitosan/acidified carbon nanotube composite hydrogel and preparation method thereof |
| CN115159542A (en) * | 2022-06-21 | 2022-10-11 | 江苏淮河化工有限公司 | Process for continuously preparing electronic-grade ammonia water by jet absorption and gradient filtration |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114736399A (en) * | 2022-05-20 | 2022-07-12 | 常州大学 | High-elasticity carboxymethyl chitosan/acidified carbon nanotube composite hydrogel and preparation method thereof |
| CN114736399B (en) * | 2022-05-20 | 2024-02-13 | 常州大学 | High-elasticity carboxymethyl chitosan/acidified carbon nano tube composite hydrogel and preparation method thereof |
| CN115159542A (en) * | 2022-06-21 | 2022-10-11 | 江苏淮河化工有限公司 | Process for continuously preparing electronic-grade ammonia water by jet absorption and gradient filtration |
| CN115159542B (en) * | 2022-06-21 | 2024-02-02 | 江苏淮河化工有限公司 | Process for continuously preparing electronic grade ammonia water by spray absorption and gradient filtration method |
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