CN101781375A - Preparation method of organic soluble photosensitive chitosan derivative - Google Patents
Preparation method of organic soluble photosensitive chitosan derivative Download PDFInfo
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- CN101781375A CN101781375A CN201010137445A CN201010137445A CN101781375A CN 101781375 A CN101781375 A CN 101781375A CN 201010137445 A CN201010137445 A CN 201010137445A CN 201010137445 A CN201010137445 A CN 201010137445A CN 101781375 A CN101781375 A CN 101781375A
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Abstract
The invention relates to a preparation method of an organic soluble photosensitive chitosan derivative. The method comprises the following steps that: 2g of chitosan is added into 70ml of triethylamine to be stirred at room temperature, so that the chitosan is uniformly dispersed in the triethylamine; the carbon tetrachloride solution of 10 weight percent of photosensitive chloride monomer is prepared, wherein the amount of the added photosensitive chloride monomer is 0.5 to 8 times of the mole of chitosan on the amino, imino and hydroxyl; chloride monomer solution is slowly dripped into chitosan solution, to be continuously stirred; after all the solution is dripped, the reaction is continued to be carried out for 2 to 6h; after the reaction, filtration is carried out, and powdery solid is prepared; and then 8 weight percent of sodium bicarbonate solution is washed by water for 3 times; the product washed by water is filtered, vacuumized and dried to prepare the chitosan derivative; and the derivative can be dissolved in acetone, toluene, N, N-dimethylformamide, benzene and other organic solutions. A post-processing purification process without toxic, harm or pollution is adopted in the preparation process, and the preparation method of the invention is an environmental-friendly process method.
Description
Technical field
The present invention relates to a kind of preparation method of organic-dissolvable photosensitive chitosan derivate.
Background technology
Chitin is that output is only second to cellulosic second largest renewable resources in the nature product, also is to be only second on the most important animal structure of protein gelatine and the earth the nitrogenous natural organic matter of quantity maximum beyond the isolating protein on the biology.Chitosan (1,4-two-amino-2-deoxidation-callose) is the structured material of Crustacean shell, is the N-deacetylation product of chitin, and generally speaking, the N-ethanoyl is sloughed more than 55% just can be referred to as chitosan.Advantages such as that chitosan not only has is nontoxic, excellent biological compatibility, biodegradability, also have cancer resistance, germ resistance, hemostatic, strengthen many excellent physiological properties such as human immunological competence.Therefore, chitosan has a bigger using value in that food, makeup, environmental protection, weaving, printing and dyeing, papermaking etc. are industrial, especially is used widely in bio-medical material, bio-pharmaceuticals and tissue engineering material field.
But because the special construction of chitosan, its intramolecularly and the intermolecular hydrogen bond action power that exists, the intermolecular ordered structure that exists, make chitosan be not dissolved in water and the common organic solvents, only be dissolved in dilute acid solution, this has greatly limited it in industrial application, and for widening its range of application, the researchist has carried out chemical modification to chitosan.Contain modifiable groups such as a large amount of hydroxyls and amino on the chitosan molecule chain, can obtain the derivative of various specific functions by chemical modification.Contain chromophore or auxochromous group in the chitosan derivatives, can ultraviolet absorption peak be arranged at 200～400nm place.The chemistry uv-absorbing agent is used for the product of all kinds of ultraviolet radiation preventing functions, for human body provides good protective action.
Ventilation property after the chitosan derivatives film forming, humidity-preserving type and anti-ageing, crease-resistant, beauty treatment, health-care effect, it is that present synthetic materials is incomparable that skin is had no stimulation, therefore chitosan is used more and more widely in daily chemical industry, the makeup kind of being made by chitosan is a lot, such as cleansing milk, cream frost, mousse, hair-strengthening agent etc.Domestic and international many enterprises have made product and have been invested in market.
Most of document and patent are the preparations about water-solubility chitosan derivative and oil soluble chitosan derivative.People such as Santosh Kumar have studied (International Journal of BiologicalMacromolecules, 2009 (45): 330-337) a kind of preparation and sign of novel N-heterocycle chitosan derivatives, it has uv-absorbing ability preferably.People such as R.Jayakumar have reported (International Journal of BiologicalMacromolecules, 2008 (42): 335-339) synthetic and characterized phosphonized chitosan with a kind of novel method.I.M.El-Sherbiny has delivered (European Polymer Journal, 2009 (45): 199-210) a kind of synthetic and sign of novel adsorbable metal ion carboxymethyl chitosan derivative.People such as Kensuke Sakurai have reported that (Journal of AppliedPolymer Science, 2005 (43): 1354-1364) chitosan and the unsaturated chitosan derivatives of cinnamyl chloride prepared in reaction are used as uv-absorbing agent.Chen Yu etc. have studied that (polymer material science and engineering, 2005 (21): 286-289) the Chinese cassia tree acylation modification of chitosan and chitin illustrates that the cinnyl chitosan has uv-absorbing ability preferably at the 280nm place.Zhang Haoqin etc. have reported that (colleges and universities' chemical engineering journal, 2009 (3): 522-526) interfacial polymerization prepares chitosan and pyromellitic trimethylsilyl chloride composite nanometer filtering film.Huang Liyao etc. have delivered (Huaqiao University's journal, 2006 (26): 439-441) the long aliphatic chain Preparation of Hydrophobing Acyl Chitosan of hydrophobization.Chinese patent CN101367886 (open day: 2009.2.18) disclose a kind of employing acyl chloride reaction preparation feedback shell polysaccharid derivative.Chinese patent CN1594367 (open day: 2005.3.16) disclose a kind of water-soluble O-chitosan derivatives and application thereof.Chinese patent CN101050243 (open day: 2009.6.24) disclose a kind of amphipathic chitose derivative and preparation method thereof and the application in pharmaceutics.
More than these methods have following shortcoming: 1, the complicated catalyzer that needs of preparation method, the aftertreatment trouble has increased cost, has reduced the using value of chitosan derivatives; 2, reaction conditions is violent, harsh, is not easy control; 3, the power consumption source is more in the preparation process; 4, Fan Ying by product is more, is unfavorable for purifying and separating.
Summary of the invention
The objective of the invention is to overcome the shortcoming that prior art exists, a kind of preparation method of organic-dissolvable photosensitive chitosan derivate is provided, the chitosan derivatives of preparation can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene and at 270～280nm place uv-absorbing is arranged.
The preparation method of organic-dissolvable photosensitive chitosan derivate provided by the present invention may further comprise the steps:
1, (1) joins the 2g chitosan in the triethylamine of 70ml, stirs under the room temperature, and chitosan is dispersed in the triethylamine;
(2) photosensitivity acyl chloride monomer is added in the carbon tetrachloride solution, is mixed with the monomeric carbon tetrachloride solution of photosensitivity acyl chloride;
(3) the monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir;
(4) all drip after, continue reaction 2～6h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, with 8wt% sodium hydrogen carbonate solution washing 3 times, the product after the washing is filtered then, vacuum-drying promptly gets organic-dissolvable photosensitive chitosan derivate.
2, according to the preparation method of claim 1, it is characterized in that the chitosan described in the step (1) is a chitosan, its deacetylation is 50～90%, weight-average molecular weight is 3,000～1,000,000.
3,, it is characterized in that the chitosan described in the step (1) is dispersed in the triethylamine according to the preparation method of claim 1.
4,, it is characterized in that the weight percent of the monomeric carbon tetrachloride solution of the described photosensitivity acyl chloride of step (2) is 10% according to the preparation method of claim 1.
5, according to the preparation method of claim 1, it is characterized in that the photosensitivity acyl chloride monomer described in the step (2) is: cinnamyl chloride, Benzoyl chloride, phthalyl chloride, to anisole SULPHURYL CHLORIDE, Tosyl chloride, phenyllacetyl chloride, 3,4-(methylenedioxy) Benzoyl chloride, hydrocinnamoyl chloride and benzene methylsulfonyl chloride.Its structural formula such as figure below:
6,, it is characterized in that the monomeric add-on of photosensitivity acyl chloride described in the step (2) is amino on the chitosan, imino-and hydroxyl mole number 0.5～8 times according to the preparation method of claim 1.
7, according to the preparation method of claim 1, it is characterized in that the organic-dissolvable photosensitive chitosan derivate described in the step (3) has following general structure (I), its deacetylation is 50～90%, substitution value is 0.5～3.5.
General formula (I)
In the formula, R=C
9H
7O, C
7H
5O, C
8H
4O
2Cl, C
7H
7O
3S, C
7H
7SO
2, C
8H
7O, C
8H
5O
3, C
9H
9O, C
7H
7O
2S, x are 0.5～0.9.
Compared with prior art, the inventive method has the effect of following excellence:
1, photosensitivity acyl chloride monomer is an important chemical material; generate chitosan derivatives with chitosan generation acylation reaction; its substituted radical contains chromophore and auxochromous group; original biological activity of chitosan and biocompatibility have been kept; both excellent properties are combined; product has uv-absorbing ability preferably, is used as uv-absorbing agent in cosmetics of everyday use, has higher utility.
2, organic-dissolvable photosensitive chitosan derivate since hydrogen bond action between amino on the chitosan, imino-and the hydroxyl can not be dissolved in the organic solvent.With photosensitivity acyl chloride monomer generation acylation reaction; broken original hydrogen bond crystalline texture in the chitosan molecule; the introducing of chromophore and auxochromous group can make it be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene, has increased range of application.
3, preparation feedback process controllability is strong, and experimental installation is simple, and the reaction process easy handling has been saved raw material and cost, is energy-saving production technique; Help this Product industrialization, for the application of chitosan derivatives is had laid a good foundation.
Embodiment
Embodiment 1
2g chitosan (deacetylation DP=80%, weight-average molecular weight Mw=500,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; Cinnamyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of cinnamyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 0.5 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 6h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium hydrogen carbonate solution washing 3 times, product after the washing is filtered, it is 0.5 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
9H
7O, x are 0.8.
Configuration concentration is 0.1wt%N, N-methylformamide solution, and it has absorption peak at ultraviolet 276nm place.
Embodiment 2
2g chitosan (deacetylation DP=70%, weight-average molecular weight Mw=1,000,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; Benzoyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of Benzoyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 2 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 4h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 1.6 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
7H
5O, x are 0.7.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 280nm place.
Embodiment 3
2g chitosan (deacetylation DP=50%, weight-average molecular weight Mw=100,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; To be added in the carbon tetrachloride solution the anisole SULPHURYL CHLORIDE, and be mixed with the carbon tetrachloride solution to the anisole SULPHURYL CHLORIDE, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 3 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 6h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 2.3 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
7H
7O
3S, x are 0.50.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 277nm place.
Embodiment 4
2g chitosan (deacetylation DP=60%, weight-average molecular weight Mw=20,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; Tosyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of Tosyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 4 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 2h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 2.6 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
7H
7SO
2, x is 0.60.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 278nm place.
Embodiment 5
2g chitosan (deacetylation DP=85%, weight-average molecular weight Mw=50,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; Phenyllacetyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of phenyllacetyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 3.5 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 6h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 2.5 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
8H
7O, x are 0.85.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 275nm place.
Embodiment 6
2g chitosan (deacetylation DP=70%, weight-average molecular weight Mw=3,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; Phthalyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of phthalyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 6 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 2h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 3.4 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
8H
4O
2Cl, x are 0.70.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 279nm place.
Embodiment 7
2g chitosan (deacetylation DP=80%, weight-average molecular weight Mw=200,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; With 3,4-(methylenedioxy) Benzoyl chloride is added in the carbon tetrachloride solution, is mixed with 3, the carbon tetrachloride solution of 4-(methylenedioxy) Benzoyl chloride, and wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 1 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 4h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 0.7 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
8H
5O
3, x is 0.80.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 273nm place.
Embodiment 8
2g chitosan (deacetylation DP=60%, weight-average molecular weight Mw=200,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; Hydrocinnamoyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of hydrocinnamoyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 8 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 2h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 3.5 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
9H
9O, x are 0.60.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 279nm place.
Embodiment 9
2g chitosan (deacetylation DP=90%, weight-average molecular weight Mw=100,000) is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine; The benzene methylsulfonyl chloride is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of benzene methylsulfonyl chloride, wherein the monomeric add-on of photosensitivity acyl chloride is amino on the chitosan, imino-and hydroxyl mole number 2 times; The monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir; After treating all to drip, continue reaction 3h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, then with 8wt% sodium bicarbonate washing 3 times, product after the washing is filtered, it is 1.4 photosensitive chitosan derivate that vacuum-drying promptly gets substitution value, can be dissolved in acetone, toluene, N, in the organic solutions such as dinethylformamide and benzene.
Organic-dissolvable photosensitive chitosan derivate has following structure:
In the formula, R=C
7H
7O
2S, x are 0.90.
Configuration concentration is 0.1wt%N, dinethylformamide solution, and it has absorption peak at ultraviolet 275nm place.
Claims (7)
1. the preparation method of an organic-dissolvable photosensitive chitosan derivate is characterized in that may further comprise the steps:
(1) the 2g chitosan is joined in the triethylamine of 70ml, stir under the room temperature, chitosan is dispersed in the triethylamine;
(2) photosensitivity acyl chloride monomer is added in the carbon tetrachloride solution, is mixed with the carbon tetrachloride solution of photo-sensitive monomer;
(3) the monomeric carbon tetrachloride solution of photosensitivity acyl chloride is slowly dropped in the chitosan solution, and constantly stir;
(4) all drip after, continue reaction 2～6h, after reaction is finished, carry out suction filtration, obtain pulverulent solids, with 8wt% sodium hydrogen carbonate solution washing 3 times, the product after the washing is filtered then, vacuum-drying promptly gets organic-dissolvable photosensitive chitosan derivate.
2. according to the preparation method of claim 1, it is characterized in that the chitosan described in the step (1) is a chitosan, its deacetylation is 50～90%, and weight-average molecular weight is 3,000～1,000,000.
3. according to the preparation method of claim 1, it is characterized in that the chitosan described in the step (1) is dispersed in the triethylamine.
4. according to the preparation method of claim 1, it is characterized in that the weight percent of the monomeric carbon tetrachloride solution of the described photosensitivity acyl chloride of step (2) is 10%.
5. according to the preparation method of claim 1, it is characterized in that the photosensitivity acyl chloride monomer described in the step (2) is: cinnamyl chloride, Benzoyl chloride, phthalyl chloride, to anisole SULPHURYL CHLORIDE, Tosyl chloride, phenyllacetyl chloride, 3,4-(methylenedioxy) Benzoyl chloride, hydrocinnamoyl chloride and benzene methylsulfonyl chloride.
Its structural formula such as figure below:
6. according to the preparation method of claim 1, it is characterized in that the monomeric add-on of photosensitivity acyl chloride described in the step (2) is amino on the chitosan, imino-and hydroxyl mole number 0.5～8 times.
7. according to the preparation method of claim 1, it is characterized in that the organic-dissolvable photosensitive chitosan derivate described in the step (3) has following general structure (I), its deacetylation is 50～90%, and substitution value is 0.5～3.5.
General formula (I)
In the formula, R=C
9H
7O, C
7H
5O, C
8H
4O
2Cl, C
7H
7O
3S, C
7H
7SO
2, C
8H
7O, C
8H
5O
3, C
9H
9O, C
7H
7O
2S, x are 0.5～0.9.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276755A (en) * | 2011-07-06 | 2011-12-14 | 北京化工大学 | Photopolymerizable chitosan derivative as well as preparation method and application thereof |
| CN105616074A (en) * | 2016-02-26 | 2016-06-01 | 刘小辉 | Highly-antibacterial novel slight-soluble healthcare sanitary napkin capable of adsorbing heavy metal particles |
| CN105616075A (en) * | 2016-02-26 | 2016-06-01 | 刘小辉 | Highly-antibacterial novel slightly-soluble healthcare sanitary pad capable of adsorbing heavy metal particles |
| CN105662730A (en) * | 2016-02-26 | 2016-06-15 | 湖北立天生物工程有限公司 | Novel slight soluble healthcare function paper diaper with high antibacterial performance and high heavy metal micro-particle adsorbing performance |
| CN105777940A (en) * | 2016-04-29 | 2016-07-20 | 江南大学 | Water-soluble light-sensitive chitosan derivative and method for preparing same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367886A (en) * | 2008-10-17 | 2009-02-18 | 北京化工大学 | Preparation method for reactive chitosan derivant |
-
2010
- 2010-04-01 CN CN201010137445A patent/CN101781375A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367886A (en) * | 2008-10-17 | 2009-02-18 | 北京化工大学 | Preparation method for reactive chitosan derivant |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276755A (en) * | 2011-07-06 | 2011-12-14 | 北京化工大学 | Photopolymerizable chitosan derivative as well as preparation method and application thereof |
| CN105616074A (en) * | 2016-02-26 | 2016-06-01 | 刘小辉 | Highly-antibacterial novel slight-soluble healthcare sanitary napkin capable of adsorbing heavy metal particles |
| CN105616075A (en) * | 2016-02-26 | 2016-06-01 | 刘小辉 | Highly-antibacterial novel slightly-soluble healthcare sanitary pad capable of adsorbing heavy metal particles |
| CN105662730A (en) * | 2016-02-26 | 2016-06-15 | 湖北立天生物工程有限公司 | Novel slight soluble healthcare function paper diaper with high antibacterial performance and high heavy metal micro-particle adsorbing performance |
| CN105616074B (en) * | 2016-02-26 | 2022-03-08 | 海南赫图投资有限公司 | Novel slightly soluble health function sanitary towel of high antibiotic, absorption heavy metal tiny particle |
| CN105662730B (en) * | 2016-02-26 | 2022-03-08 | 海南赫图投资有限公司 | Novel slightly soluble health function panty-shape diapers of high antibiotic, absorption heavy metal tiny particle |
| CN105616075B (en) * | 2016-02-26 | 2022-03-08 | 海南赫图投资有限公司 | Novel slightly soluble health care function sanitary pad with high antibacterial property and capable of adsorbing heavy metal particles |
| CN105777940A (en) * | 2016-04-29 | 2016-07-20 | 江南大学 | Water-soluble light-sensitive chitosan derivative and method for preparing same |
| CN105777940B (en) * | 2016-04-29 | 2018-03-20 | 江南大学 | A kind of water-soluble photosensitive chitosan derivatives and preparation method thereof |
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Application publication date: 20100721 |