CN1587282A - Process for preparing poly succinimide crosslinking modified chitosan material - Google Patents
Process for preparing poly succinimide crosslinking modified chitosan material Download PDFInfo
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- CN1587282A CN1587282A CN 200410053261 CN200410053261A CN1587282A CN 1587282 A CN1587282 A CN 1587282A CN 200410053261 CN200410053261 CN 200410053261 CN 200410053261 A CN200410053261 A CN 200410053261A CN 1587282 A CN1587282 A CN 1587282A
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- polysuccinimide
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- 229920001661 Chitosan Polymers 0.000 title claims abstract description 62
- 239000000463 material Substances 0.000 title claims abstract description 54
- 238000004132 cross linking Methods 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title 2
- 229960002317 succinimide Drugs 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001291 vacuum drying Methods 0.000 claims abstract description 14
- 239000012153 distilled water Substances 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 239000011148 porous material Substances 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052802 copper Inorganic materials 0.000 claims abstract description 10
- 239000010949 copper Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000000835 fiber Substances 0.000 claims abstract description 8
- 238000007654 immersion Methods 0.000 claims description 10
- 229920002101 Chitin Polymers 0.000 claims description 9
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims description 8
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000004048 modification Effects 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 229920001436 collagen Polymers 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012528 membrane Substances 0.000 abstract description 2
- 238000004381 surface treatment Methods 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 238000002791 soaking Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Materials For Medical Uses (AREA)
Abstract
During the preparation of polysuccinimide cross-linking modified chitosan material, polysuccinimide prepared through reaction of 5-30 min and with different molecular weight is dissolved in N, N-dimethyl formamide or N, N-dimethyl acetamide to prepare transparent solution system of 5-10 wt% concentration; chitosan fiber, membrane or porous material of 10 wt% is suspended in the polysuccinimide solution system and reacted at room temperature under stirring for 12 hr; organic amine in 2-5 wt% is then added to modify the surface of chitosan through reaction at room temperature for 12 hr; and through filtering with copper net, thrice soaking and washing with distilled water and vacuum drying at 40 deg.c, the cross-linking modified chitosan material is prepared. The present invention has simple technological process, convenient operation and short production period, and may be used in surface treatment of chitosan.
Description
Technical field
The present invention relates to a kind of preparation method of cross-linking modified chitosan material, specifically is the preparation method of the cross-linking modified chitosan material of a kind of polysuccinimide.Be used for the surface treatment technology of material field.
Background technology
Chitin is that N-ethanoyl D-glucose passes through the straight-chain polysaccharide that β (1 → 4) glycosidic link links to each other, extensively is present in crustacean and the arthropods heart bacteria cell wall, and be one of organic compound that is only second on the earth cellulosic most abundant.Chitin is through taking off product---the chitosan that acetyl is handled, owing to contain the higher free amine group of a large amount of activity in the molecular structure, therefore have some unique physico-chemical property and physiological functions, have broad application prospects at medicine, food, makeup, agricultural and environmental protection aspects, particularly have many effects to the human body beneficial with this chitosan biological health-care product of making, by European and American countries be described as dewater, the sixth-largest vital principle of needed by human body outside protein, carbohydrate, Mierocrystalline cellulose and the mineral substance.
Chitin fiber can be used as operating sutures, fabric, non-woven fabrics raw material, and the chitosan film material can be used as Freshkeeping Packaging, permeable membrane etc., and chitosan multi-porous material can be used as bone repair tissue engineered vector material.Though chitosan self has good film-forming properties, but still need carry out cross-linking modifiedly, improve performances such as its tensile strength, water resisting property, to satisfy user demand to chitosan material.Oyrton A.C.Monteiro Jr., Claudio A. is at " Somestudies of crosslinking chitosan-glutaraldehyde interaction in a homogeneoussystem " (International Journal of Biological Macromolecules, 1999,26,119-128) (" research of chitosan and glutaraldehyde cross-linking reaction in the homogeneous system ", international biomacromolecule magazine) points out in the literary composition that the traditional cross-linking method of chitosan material is to use glutaraldehyde as linking agent, but product S chiff (Schiff) alkali that chitosan and glutaraldehyde reaction generate is unstable and certain toxicity is arranged, and generally needs further with sodium borohydride its reduction to be changed into stable keys.Simultaneously, discover that glutaraldehyde has certain cytotoxicity,, its application is restricted even also cell growth is inhibited for lower concentration.
Summary of the invention
The objective of the invention is at above shortcomings in the prior art, the preparation method of the cross-linking modified chitosan material of a kind of polysuccinimide is proposed, make it select for use polysuccinimide to make linking agent, polysuccinimide can make the crosslinked bond material of amido linkage of stability and safety with the chitosan single step reaction, and solvent can reuse, save cost, technology is simple, and is easy to operate.
The present invention is achieved by the following technical solutions, chitin fiber, mould material or porous material are suspended in the polysuccinimide organic solvent system, in system, add the amine organism as surface-modifying agent, stir, reaction back filtering out materials under the room temperature, with the distilled water immersion washing for several times, vacuum-drying obtains cross-linking modified chitosan material.
Below the present invention is done further concrete the qualification:
The different polysuccinimide product of molecular weight that reaction was made in 5～30 minutes is dissolved in N, dinethylformamide or N, make the clear solution system of 5～10% weight percents in the N-N,N-DIMETHYLACETAMIDE, chitin fiber with 10% weight percent, film or porous material are suspended in the polysuccinimide solution system, stir, react 12h under the room temperature, add 2～5% weight percent amine organism such as thanomins then, urea, butanediamine, hexanediamine, gelatin, collagen, amino acid and polypeptide, chitosan material is carried out surface modification, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan material.
Described polysuccinimide product, its preparation method is: the 12.5gDL-aspartic acid is placed the 250ml round-bottomed flask, add 6.5g85% phosphoric acid,, abundant mixing, 180 ℃ of decompressions were reacted 5～30 minutes, add 50ml N while hot, dinethylformamide, treat product dissolving after, join in the 300ml water, filter out precipitation, through being washed to neutrality, products therefrom is dissolved in 50ml N, dinethylformamide, reprecipitation, twice, 100 ℃ of vacuum-drying makes the polysuccinimide product repeatedly.
The present invention compares with traditional method, has avoided the use of glutaraldehyde, and polysuccinimide can react with the amino in the chitosan, directly makes the crosslinked bond material of amido linkage of stability and safety.The present invention by the amine organism can with polysuccinimide room temperature reaction characteristic, the part polysuccinimide of failing chitosan and crosslinking reaction taking place is further reacted completely with the amine organism, and, realize surface modification to chitosan material with certain amines type organic introducing material surface.The present invention selects for use polysuccinimide to make linking agent, because the different reaction times of control can make the polysuccinimide product of different molecular weight, can pass through to change the molecular weight of polysuccinimide and the crosslinking degree of consumption control chitosan material.The cross-linking modified of chitosan material carries out in room temperature among the present invention, and the chitosan material distilled water wash that filters out can be removed remaining solvent of material surface and unreacting substance, technology is simple, N, dinethylformamide, N, N-dimethylacetamide solvent system can reuse, saves cost.
Embodiment
Content below in conjunction with the inventive method provides following examples:
Embodiment 1:
Chitin fiber and 5% polysuccinimide/N, the enforcement of dinethylformamide.
The 12.5gDL-aspartic acid is placed the 250ml round-bottomed flask, add 6.5g85% phosphoric acid, fully mixing, 180 ℃ of decompressions were reacted 10 minutes, added 50ml N while hot, dinethylformamide, after treating the product dissolving, join in the 300ml water, filter out precipitation, through being washed to neutrality, products therefrom is dissolved in 50ml N, dinethylformamide, reprecipitation, twice, 100 ℃ of vacuum-drying makes the polysuccinimide product repeatedly.
The polysuccinimide product is dissolved in N, make the clear solution of 5% weight percent in the dinethylformamide, the chitin fiber of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 2% weight percent amine organism such as thanomin then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitin fiber.
Implementation result: the amino generation crosslinking reaction in polysuccinimide and the chitosan.
Embodiment 2:
Chitosan film material and 5% polysuccinimide/N, the enforcement of dinethylformamide.
Adopt embodiment 1 same method to make the polysuccinimide product.
The polysuccinimide product is dissolved in N, make the clear solution of 5% weight percent in the dinethylformamide, the chitosan film material of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 2% weight percent amine organism such as thanomin then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan film material.
Implementation result: the amino generation crosslinking reaction in polysuccinimide and the chitosan.
Embodiment 3:
Chitosan multi-porous material and 5% polysuccinimide/N, the enforcement of dinethylformamide.
Adopt embodiment 1 same method to make the polysuccinimide product.
The polysuccinimide product is dissolved in N, make the clear solution of 5% weight percent in the dinethylformamide, the chitosan multi-porous material of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 2% weight percent amine organism such as thanomin then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan multi-porous material.
Implementation result: the amino generation crosslinking reaction in polysuccinimide and the chitosan.
Embodiment 4:
The enforcement of chitosan film material and 5% polysuccinimide/N,N-dimethylacetamide.
Adopt embodiment 1 same method to make the polysuccinimide product.
The polysuccinimide product is dissolved in N, make the clear solution of 5% weight percent in the N-N,N-DIMETHYLACETAMIDE, the chitosan film material of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 2% weight percent amine organism such as thanomin then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan film material.
Implementation result: the amino generation crosslinking reaction in polysuccinimide and the chitosan.
Embodiment 5:
Chitosan film material and S% hang down polysuccinimide/N, the enforcement of dinethylformamide.
The 12.5gDL-aspartic acid is placed the 250ml round-bottomed flask, add 6.5g85% phosphoric acid, fully mixing, 180 ℃ of decompressions were reacted 5 minutes, added 50ml N while hot, dinethylformamide, after treating the product dissolving, join in the 300ml water, filter out precipitation, through being washed to neutrality, products therefrom is dissolved in 50ml N, dinethylformamide, reprecipitation, twice, 100 ℃ of vacuum-drying makes the polysuccinimide product repeatedly.
The polysuccinimide product is dissolved in N, make the clear solution of 5% weight percent in the dinethylformamide, the chitosan film material of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 2% weight percent amine organism such as thanomin then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan film material.
Implementation result: the polysuccinimide of lower molecular weight and the amino generation crosslinking reaction in the chitosan.
Embodiment 6:
Chitosan film material and 10% polysuccinimide/N, the enforcement of dinethylformamide.
Adopt embodiment 1 same method to make the polysuccinimide product.
The polysuccinimide product is dissolved in N, make the clear solution of 10% weight percent in the dinethylformamide, the chitosan film material of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 4% weight percent amine organism such as thanomin then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan material.
Implementation result: the amino generation crosslinking reaction in polysuccinimide and the chitosan.
Embodiment 7:
Chitosan multi-porous material and 10% polysuccinimide/N, dinethylformamide also use the enforcement of butanediamine surface modification.
Adopt embodiment 1 same method to make the polysuccinimide product.
The polysuccinimide product is dissolved in N, make the clear solution of 10% weight percent in the dinethylformamide, the chitosan multi-porous material of 10% weight percent is suspended in the polysuccinimide solution, stir, react 12h under the room temperature, add 5% weight percent amine organism such as thanomin and butanediamine then, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan material.
Implementation result: the amino generation crosslinking reaction in polysuccinimide and chitosan and the butanediamine molecule makes chitosan multi-porous material surface in conjunction with the butanediamine molecule.
Claims (3)
1, the preparation method of the cross-linking modified chitosan material of a kind of polysuccinimide, it is characterized in that, the different polysuccinimide product of molecular weight that reaction was made in 5～30 minutes is dissolved in N, dinethylformamide or N, make the clear solution system of 5～10% weight percents in the N-N,N-DIMETHYLACETAMIDE, chitin fiber with 10% weight percent, film or porous material are suspended in the polysuccinimide solution system, stir, react 12h under the room temperature, add 2～5% weight percent amine organism then, chitosan material is carried out surface modification, use the copper mesh filtering out materials behind the reaction 12h under the room temperature, with distilled water immersion washing three times, 40 ℃ of vacuum-dryings obtain cross-linking modified chitosan material.
2, the preparation method of the cross-linking modified chitosan material of polysuccinimide as claimed in claim 1, it is characterized in that, add the amine organism in the reaction system, chitosan material is carried out surface modification, and described amine organism comprises: thanomin, urea, butanediamine, hexanediamine, gelatin, collagen, amino acid and polypeptide.
3, the preparation method of the cross-linking modified chitosan material of polysuccinimide as claimed in claim 1 is characterized in that, by the molecular weight of change polysuccinimide or the crosslinking degree of consumption control chitosan material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410053261 CN1268649C (en) | 2004-07-29 | 2004-07-29 | Process for preparing poly succinimide crosslinking modified chitosan material |
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200410053261 CN1268649C (en) | 2004-07-29 | 2004-07-29 | Process for preparing poly succinimide crosslinking modified chitosan material |
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| CN1587282A true CN1587282A (en) | 2005-03-02 |
| CN1268649C CN1268649C (en) | 2006-08-09 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314729C (en) * | 2005-09-09 | 2007-05-09 | 天津理工大学 | Prepn process of copolymer of polyaspartic acid and chitosan |
| US8119780B2 (en) | 2006-06-02 | 2012-02-21 | Synedgen, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
| CN102690516A (en) * | 2012-06-11 | 2012-09-26 | 哈尔滨工程大学 | Biodegradable cross-linked chitosan chelating resin and preparation method thereof |
| CN107474159A (en) * | 2017-07-20 | 2017-12-15 | 莆田学院 | A kind of preparation method of the dicarboxylic acids modification of chitosan material of imidazoles 4,5 |
-
2004
- 2004-07-29 CN CN 200410053261 patent/CN1268649C/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314729C (en) * | 2005-09-09 | 2007-05-09 | 天津理工大学 | Prepn process of copolymer of polyaspartic acid and chitosan |
| US8119780B2 (en) | 2006-06-02 | 2012-02-21 | Synedgen, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
| US8658775B2 (en) | 2006-06-02 | 2014-02-25 | Shenda Baker | Chitosan-derivative compounds and methods of controlling microbial populations |
| US9029351B2 (en) | 2006-06-02 | 2015-05-12 | Synedgen, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
| US9732164B2 (en) | 2006-06-02 | 2017-08-15 | Synedgen, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
| US10494451B2 (en) | 2006-06-02 | 2019-12-03 | Synedgen, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
| CN102690516A (en) * | 2012-06-11 | 2012-09-26 | 哈尔滨工程大学 | Biodegradable cross-linked chitosan chelating resin and preparation method thereof |
| CN102690516B (en) * | 2012-06-11 | 2013-12-18 | 哈尔滨工程大学 | Biodegradable cross-linked chitosan chelating resin and preparation method thereof |
| CN107474159A (en) * | 2017-07-20 | 2017-12-15 | 莆田学院 | A kind of preparation method of the dicarboxylic acids modification of chitosan material of imidazoles 4,5 |
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| Publication number | Publication date |
|---|---|
| CN1268649C (en) | 2006-08-09 |
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Owner name: SHANGHAI RIDUO HIGH POLYMER MATERIAL CO., LTD. Free format text: FORMER OWNER: SHANGHAI JIAOTONG UNIV. Effective date: 20091023 |
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Effective date of registration: 20091023 Address after: Shanghai chemical industry zone, Fengxian District, Chu Hua Road, No. 318 Patentee after: SHANGHAI RIDUO HIGH POLYMER MATERIAL Co.,Ltd. Address before: No. 800, Dongchuan Road, Shanghai, Minhang District Patentee before: Shanghai Jiao Tong University |
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