CN106117391A - A kind of preparation method of chitosan aroma type Schiff - Google Patents
A kind of preparation method of chitosan aroma type Schiff Download PDFInfo
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- CN106117391A CN106117391A CN201610482754.4A CN201610482754A CN106117391A CN 106117391 A CN106117391 A CN 106117391A CN 201610482754 A CN201610482754 A CN 201610482754A CN 106117391 A CN106117391 A CN 106117391A
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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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention discloses the preparation method of a kind of chitosan aroma type Schiff, it is characterized in that: be with the chitosan of natural reproducible as primary raw material, it is aided with phenol and oxidant simultaneously, dicyandiamide solution containing the organic solution of catalyst reacts, prepares chitosan aroma type Schiff；This chitosan aroma type Schiff is light brown powder shape solid, dissolves in acidic aqueous solution, is slightly soluble in ethanol, methanol and isopropanol.Compared with protoconch polysaccharide, this chitosan aroma type Schiff has the anti-microbial property of excellence to escherichia coli, staphylococcus aureus and melanomyces, is expected to be applied in the field such as food preservative, antibiosis anti-inflammatory drug.Reaction condition of the present invention is gentle, and technique is simple, can promote the chitosan utilization of resources, promotes the Product processing transformation to high added value.
Description
[technical field]
The present invention relates to natural polymer field, particularly to the preparation method of a kind of chitosan aroma type Schiff.
[background technology]
Chitosan (chitosan) is commercially available natural high molecular polymer, and it is existed by chitin (Chitin)
Under the conditions of concentrated base deacetylated after product, and Chitin sees the cell bone that such as crustacean, shrimp, Eriocheir sinensis, true mattress etc. are biological
In frame and duricrust, annual biosynthesis amount reaches 10,000,000,000 tons, is the important polysaccharide of another big class in addition to cellulose.
Chitosan molecule chain exists substantial amounts of activity-NH2Base, is unique a kind of alkaline polysaccharide in nature, typically
Think ,-the NH on chitosan molecule chain2Impart unique performance that chitosan is numerous, such as biodegradable, biofacies
Capacitive, antibiotic property, nontoxic without anaphylaxis, recyclability and film property etc., the performance of these uniquenesses make chitosan medicine,
The fields such as the process of cosmetics, spice, water, METAL EXTRACTION and recovery, agricultural and food industry have wide application.Along with to shell
Deepening continuously of polysaccharide research, and also to widen its range of application, can be by chemical method on chitosan molecule chain
C-NH2 and C-OH isoreactivity reactive functionality carries out modification reaction, and forming particularity can derivant.
Activity-NH in neutral medium, in chitosan molecule chain2Base is easy to and aromatic aldehyde (or ketone), fatty aldehyde etc.
There is condensation reaction, generate the product (Schiff) of the imido grpup having very much using value.These Chitosan Schiff Bases have
The pain relieving of excellence, antiinflammatory, the antibacterial and physiologically active such as sterilizing, antiviral activity；Simultaneously because the carbon nitrogen of Chitosan Schiff Base
Double bond structure, the atom N of its hybrid orbital has lone pair electrons, and some metal ion is had special chelation, can apply
In sewage treatment area, additionally, the Chitosan Schiff Base metal complex formed is to many chemical reactions such as polymerization, oxidation
And etherification reaction etc. has catalytic action, it it is the catalyst of a kind of excellence.The institute of Chitosan Schiff Base is all at present
It is the common aldehydes such as salicylide, vanillin, benzaldehyde and cinnamic aldehyde, and few with phenol.
[summary of the invention]
The main object of the present invention is to prepare a kind of chitosan derivatives with excellent antibacterial activity and stability,
The invention provides and a kind of utilize reproducible chitosan resource and phenol to prepare novel chitosan aroma type for raw material
The method of Schiff.Compared with protoconch polysaccharide, this chitosan aroma type Schiff is to escherichia coli, staphylococcus aureus
With black enzyme bacterium, there is more excellent anti-microbial property, be expected to be applied in the field such as food preservative, antibiosis anti-inflammatory drug.
For reaching above-mentioned purpose, the technical solution adopted in the present invention is: the system of a kind of chitosan aroma type Schiff
Preparation Method, it is characterised in that: comprise the following steps:
(1) load weighted phenol, oxidant and catalyst are joined in there-necked flask, add load weighted organic molten
Agent；Described oxidant includes the combination in any of hydrogen peroxide, potassium permanganate, potassium dichromate, perchlorate, sodium hypochlorite and bromine；
(2) load weighted chitosan is dissolved in acid water-soluble in, form the chitosan solution of clarification；
(3) by Dropping funnel, lentamente chitosan solution is joined under agitation three mouthfuls described in step (1)
In flask, with the pH of alkali water-soluble regulation reaction system, react under required process conditions；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
In the present invention, as further illustrating, the catalyst described in step (1) is iron chloride, aluminum chloride, chlorination
The combination in any of zinc, lanthanum chloride and cobaltous chloride；Described organic solvent include dehydrated alcohol, methanol, isopropanol, ethyl acetate,
Hexamethylene, acetonitrile, acetone, toluene, dimethylbenzene, dimethyl sulfoxide and N, the combination in any of N-dimethylformamide.
In the present invention, as further illustrating, the phenol described in step (1) with the weight ratio of oxidant is: 98:2-
The weight ratio of 75:25, phenol and catalyst: 99:1-90:10.
In the present invention, as further illustrating, the acidic aqueous solution described in step (2) include spirit of vinegar, dilute hydrochloric acid,
Dilute sulfuric acid and the combination in any of dilute formic acid；Described chitosan solution mass fraction is 0.5-20%.
In the present invention, as further illustrating, the phenol described in step (1) and step (2) and the weight of chitosan
Ratio is: 5:95-35:65.
In the present invention, as further illustrating, the alkali water-soluble described in step (3) includes sodium hydroxide, carbonic acid
Any one in sodium, potassium hydroxide；Described pH is 7-10；Described process conditions are 20-120 DEG C of oil bath heating, reaction
Time is 10-240min.
Effect of part material is described below:
Phenol is a kind of colourless acicular crystal with special odor, be produce some resin, antibacterial, preservative and
The important source material of medicine (such as aspirin).Can also be used for sterilize surgical instruments and excremental process, skin sterilization, antipruritic and
Otitis media.The hydroxyl of phenol has the strongest reactivity, exposes in atmosphere or oxidable for quinone in the presence of oxidant.
Potassium permanganate, strong oxidizer, aubergine crystal, water soluble, meet ethanol and be i.e. reduced.It is commonly used for disinfectant, water
Cleanser, oxidant, bleach, gas absorption agent, CO 2 refining agent etc..
Hydrogen peroxide chemistry formula is H2O2, it is commonly called as hydrogen peroxide.Aqueous solution is colourless transparent liquid, is dissolved in water, alcohol, ether, no
It is dissolved in benzene, petroleum ether.Outward appearance is colourless transparent liquid, is a kind of strong oxidizer, its aqueous solution be applicable to medical wound sterilization and
Environment disinfected and food sterilization.
Potassium dichromate is orange red anorthic crystal or acicular crystal, is dissolved in water, insoluble in ethanol.Poisonous.For chrome alum processed,
Match, chromium pigment for tanning, plating, organic synthesis etc..Hypochlorous acid is a kind of strong oxidizer, can kill the pathogenic bacteria in water,
So tap water is commonly used chlorine (1L water Rio is passed through 0.002g chlorine) and is carried out sterilizing.Hypochlorous acid can make dyestuff and organic chromaticness
Fade, can be used as bleach.
Iron chloride is a kind of covalent compound, has another name called ferric chloride, is dark brown crystallization, also has flake, fusing point 306
DEG C, boiling point 315 DEG C, soluble in water and have strong water absorption, the moisture in air can be absorbed and deliquescence.FeCL3From water-soluble
Carrying six water of crystallization when liquation goes out is FeCL3·6H2O, Iron(III) chloride hexahydrate is saffron crystal.Iron chloride be one very
Important iron salt.
Aluminum chloride be colourless transparent crystal or white and the lurid crystalline powder of micro-strip.The steam of aluminum chloride or be dissolved in
In non-polar solven or when being in molten condition, all exist with the dimeric molecule form of covalency.Water soluble and many are organic molten
Agent.Aqueous solution is acidity.In the presence of aromatic hydrocarbons, aluminum chloride mixes with aluminum and can be used for synthesizing two (aromatic hydrocarbons) metal complex.
Lanthanum chloride it is generally acknowledged that lanthanum chloride includes anhydrous lanthanum chloride and many chloride hydrate lanthanum compound.For producing metal
Lanthanum and petroleum catalyst raw material, it may also be used for hydrogen storage cell material.
Zinc chloride is one of staple product of inorganic chemicals industry, and its range of application is the widest.Zinc chloride is soluble in water, is dissolved in first
Alcohol, ethanol, glycerol, acetone, ether, insoluble in liquefied ammonia.Hygroscopy is strong, can absorb moisture and deliquescence in air.There is dissolving
Metal-oxide and the characteristic of cellulose.Melted zinc chloride has good electric conductivity.Dense white cigarette is had to generate time scorching hot.Chlorine
Change zinc to be corrosive, poisonous.
Dehydrated alcohol, achromaticity and clarification liquid.There is calcination taste.Easily flowing.From air, easily absorb moisture, can be with water and chlorine
The multiple organic solvents such as imitative, ether dissolve each other with arbitrary proportion.Azeotropic mixture, fusing point-114.1 DEG C, boiling point can be formed with water
78.5℃.Index of refraction 1.361.During closed-cup, flash-point 13 DEG C, inflammable.Steam and air can form explosive mixture.
Isopropanol one organic compound, the isomers of normal propyl alcohol, call dimethylcarbinol, 2-propanol, in industry
Also IPA is made.It is.Colourless transparent liquid, has the abnormal smells from the patient like ethanol and acetone mixture.It is dissolved in water, also is soluble in alcohol, ether, benzene, chlorine
Imitate and wait most organic solvents.Isopropanol is important chemical products and raw material.Be mainly used in pharmacy, cosmetics, plastics, spice,
Coating etc..
Ethyl acetate is that the hydroxyl in acetic acid is replaced by ethyoxyl and the compound that generates.Colourless transparent liquid, has fruit
Perfume (or spice), volatile, to air-sensitive, can absorb water and divide, moisture can make it slowly decompose and react acid.Can be used as textile industry
Abluent and the extractant of natural perfume material, be also the important source material of pharmaceuticals industry and organic synthesis.
Hexamethylene another name hexahydrobenzene, for the liquid of colourless irritant abnormal smells from the patient.Water insoluble, it is dissolved in most organic molten
Agent.Easily burn.It is typically used as common solvent, chromatography standard substance and for organic synthesis, can be at resin, coating, fat
Fat, paraffin oil apoplexy due to endogenous wind are applied, and also can prepare the Organic substance such as Hexalin and Ketohexamethylene.
Acetonitrile has another name called methyl cyanide, colourless liquid, highly volatile, has the special odor being similar to ether, has excellent solvent borne
Can, multiple organic and inorganic and gaseous matter can be dissolved.There is certain toxicity, infinitely dissolve each other with water and alcohol.Acetonitrile can occur typically
Nitrile reacts, and is used for preparing many typical case's nitrogen-containing compounds, is an important organic intermediate.It is coated with for vinyl
Material, also serves as the extractant of fatty acid, alcotate, butadiene extraction agent and the solvent of acrylonitrile synthetic fiber, at fabric
Dyeing, illumination, spice manufacture and sensitive material manufacture also have many purposes.
Dimethyl sulfoxide (DMSO) is a kind of organic compounds containing sulfur, is the transparency liquid of no color or smell, is one under room temperature
Plant hygroscopic flammable liquid.There is highly polar, high boiling point, Heat stability is good, characteristic non-proton, miscible with water, can be dissolved in
Most of Organic substances such as ethanol, propanol, benzene and chloroform, are described as " alembroth ".
Dimethylbenzene is colourless transparent liquid；It is that on phenyl ring, two hydrogen, by methyl substituted product, exist o-, m-, to three kinds
Isomer, industrially, dimethylbenzene i.e. refers to the mixture of above-mentioned isomer.Dimethylbenzene tool special smell, inflammable, with ethanol, chloroform or
Ether can arbitrarily mix, insoluble in water.Boiling point is 137～140 DEG C.Dimethylbenzene belongs to lower toxicity chemical substance, dimethylbenzene
Pollution mostlys come from synthetic fibers, plastics, fuel, rubber, the additive of various coating and various adhesive, waterproof material
In, may also come from the combustion gas of fuel and Nicotiana tabacum L..
The method have the advantages that
1. the present invention is in acid condition, is introduced on chitosan molecule chain by the phenyl ring of rigidity, is entered by the Isosorbide-5-Nitrae position of phenyl ring
Row crosslinking, defines stable network structure, has more preferable acid-proof alkaline.
2. antibacterial, antiinflammatory performance that chitosan can be had by the chitosan aroma type Schiff that prepared by the present invention and phenol
Performance effectively combine, have in the case of high yield escherichia coli, staphylococcus aureus and black enzyme the most simultaneously
Bacterium has more excellent antibacterial activity.
3. the reaction condition of the present invention is gentle, and technique is simple, and productivity is high, can promote chitosan comprehensive utilization of resources, promotes
Product processing is from the low transformation used to high added value.
[detailed description of the invention]
Embodiment 1:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 2.4g phenol, 0.21g potassium permanganate and 0.12g aluminum chloride join 500mL, add
Enter the 250mL dehydrated alcohol weighed；
(2) weigh 5.1g chitosan to be dissolved in the aqueous acetic acid that 170mL mass fraction is 2%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask.PH=by the sodium hydrate aqueous solution alkali water-soluble regulation reaction system that mass fraction is 3%
8, react 150min at 60 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 6.9g chitosan aroma type Schiff product.
Embodiment 2:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh 2.0g phenol, 0.25g hydrogen peroxide potassium permanganate and 0.10g lanthanum chloride and join the there-necked flask of 500mL
In, add the 200mL toluene weighed；
(2) weigh 4.8g chitosan to be dissolved in the aqueous sulfuric acid that 190mL mass fraction is 1%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask.The pH=7 of reaction system is regulated with the aqueous sodium carbonate alkali water-soluble that mass fraction is 5%,
120min is reacted at 105 DEG C.
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff；
It is computed, available 5.78g chitosan aroma type Schiff product.
Embodiment 3:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 1.5g phenol, 0.30g hydrogen peroxide and 0.08g iron chloride join 500mL, add
The 185mL dimethyl sulfoxide weighed；
(2) weighing 8g chitosan to be dissolved in the aqueous acetic acid that 200mL mass fraction is 2%, the shell forming clarification gathers
Sugar juice；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask, with the pH=of the potassium hydroxide aqueous solution alkali water-soluble regulation reaction system that mass fraction is 4%
9, react 200min at 80 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 7.32g chitosan aroma type Schiff product.
Embodiment 4:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 3.6g phenol, 0.20g bromine and 0.25g cobaltous chloride join 500mL, add and weigh
160mL methanol；
(2) weigh 8.5g chitosan to be dissolved in the aqueous hydrochloric acid solution that 250mL mass fraction is 5%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask.PH=by the sodium hydrate aqueous solution alkali water-soluble regulation reaction system that mass fraction is 5%
10, react 60min at 40 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 5.29g chitosan aroma type Schiff product.
Embodiment 5:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 1.2g phenol, 0.3g sodium hypochlorite and 0.18g zinc chloride join 500mL, add
The 200mL hexamethylene weighed；
(2) weigh 10.0g chitosan to be dissolved in the aqueous sulfuric acid that 200mL mass fraction is 5%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask, with the pH=of the potassium hydroxide aqueous solution alkali water-soluble regulation reaction system that mass fraction is 2%
8, react 200min at 110 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 10.92g chitosan aroma type Schiff product.
Embodiment 6:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 3.2g phenol, 0.5g sodium perchlorate and 0.25g aluminum chloride join 500mL, add
The 150mL ethyl acetate weighed；
(2) weighing 7.0g chitosan and being dissolved in 250mL mass fraction is in 4% aqueous acetic acid, and the shell forming clarification gathers
Sugar juice；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask.The pH=8 of reaction system is regulated, at 90 DEG C with the sodium hydrate aqueous solution alkali water-soluble of 2%w/v
Reaction 180min；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 9.3g chitosan aroma type Schiff product.
Embodiment 7:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 2.8g phenol, 0.25g potassium dichromate and 0.06g zinc chloride join 500mL, add
Enter the 100mLN weighed, N-dimethylformamide；
(2) weigh 5.6g chitosan to be dissolved in the aqueous hydrochloric acid solution that 150mL mass fraction is 2%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask.PH=by the potassium hydroxide aqueous solution alkali water-soluble regulation reaction system that mass fraction is 3%
9, react 240min at 20 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 6.65g chitosan aroma type Schiff product.
Embodiment 8:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 0.9g phenol, 0.15g hydrogen peroxide and 0.15g cobaltous chloride join 500mL, add
The 120mL acetonitrile weighed；
(2) weigh 3.5g chitosan to be dissolved in the aqueous acetic acid that 120mL mass fraction is 3%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask, regulate the pH=7 of reaction system with the aqueous sodium carbonate alkali water-soluble that mass fraction is 3%,
100min is reacted at 85 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 3.86g chitosan aroma type Schiff product.
Embodiment 9:
The preparation method of a kind of chitosan aroma type Schiff, comprises the following steps:
(1) weigh in the there-necked flask that 2.8g phenol, 0.42g potassium permanganate and 0.22g lanthanum chloride join 500mL, add
Enter the 175mL dimethylbenzene weighed；
(2) weigh 7.5g chitosan to be dissolved in the aqueous acetic acid that 160mL mass fraction is 2%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask.PH=by the sodium hydrate aqueous solution alkali water-soluble regulation reaction system that mass fraction is 3%
8, react 180min at 75 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 9.24g chitosan aroma type Schiff product.
Contrast test 1:
The product of chitosan and embodiment 1-3 is carried out colibacillary antibacterial tests, and result of the test is shown in Table 1.
Table 1:
Table 1 result shows: the antibiotic rate that colibacillary antibiotic rate is higher than chitosan alone of embodiment 1-3.To greatly
The antibiotic rate of enterobacteria be preferably: embodiment 1 > embodiment 3 > embodiment 2 > chitosan.
Contrast test 2:
Product by chitosan and embodiment 4-6 carries out the antibacterial tests of staphylococcus aureus, and result of the test is shown in Table 2.
Table 2:
Table 2 result shows: the antibiotic rate to staphylococcus aureus of embodiment 4-6 is antibacterial higher than chitosan alone
Rate.To the antibiotic rate of staphylococcus aureus it is preferably: embodiment 6 > embodiment 5 > embodiment 4 > chitosan.
Contrast test 3:
Product by chitosan and embodiment 4-6 carries out the antibacterial tests of melanomyces, and result of the test is shown in Table 3.
Table 3:
Table 3 result shows: the antibiotic rate to melanomyces of embodiment 4-9 is higher than the antibiotic rate of chitosan alone.To black mould
The antibiotic rate of bacterium be preferably: embodiment 8 > embodiment 7 > embodiment 9 > chitosan.
A kind of better embodiment in the present invention:
(1) weigh in the there-necked flask that 0.9g phenol, 0.15g hydrogen peroxide and 0.15g cobaltous chloride join 500mL, add
The 120mL acetonitrile weighed；
(2) weigh 3.5g chitosan to be dissolved in the aqueous acetic acid that 120mL mass fraction is 3%, form the shell of clarification
Polysaccharide solution；
(3) by Dropping funnel, lentamente chitosan solution is joined under the stirring condition of 250r/min step (1)
In described there-necked flask, regulate the pH=7 of reaction system with the aqueous sodium carbonate alkali water-soluble that mass fraction is 3%,
100min is reacted at 85 DEG C；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan fragrance of light brown powder shape
Type Schiff.
It is computed, available 3.86g chitosan aroma type Schiff product.
Described above is the detailed description for the preferable possible embodiments of the present invention, but embodiment is not limited to this
Bright patent claim, the equal change completed under the technical spirit suggested by all present invention or modification change, all should belong to
In the contained the scope of the claims of the present invention.
Claims (6)
1. the preparation method of a chitosan aroma type Schiff, it is characterised in that: comprise the following steps:
(1) load weighted phenol, oxidant and catalyst are joined in there-necked flask, add load weighted organic solvent；Institute
The oxidant stated includes the combination in any of hydrogen peroxide, potassium permanganate, potassium dichromate, perchlorate, sodium hypochlorite and bromine；
(2) load weighted chitosan is dissolved in acid water-soluble in, form the chitosan solution of clarification；
(3) by Dropping funnel, lentamente chitosan solution is joined under agitation the there-necked flask described in step (1)
In, with the pH of alkali water-soluble regulation reaction system, react under required process conditions；
(4) sucking filtration, collects filtering residue, and with absolute ethanol washing, lyophilization i.e. obtains the chitosan aroma type of light brown powder shape
Schiff.
The preparation method of a kind of chitosan aroma type Schiff the most as claimed in claim 1, it is characterised in that: step (1)
Described in the combination in any that catalyst is iron chloride, aluminum chloride, zinc chloride, lanthanum chloride and cobaltous chloride；Described organic solvent
Including dehydrated alcohol, methanol, isopropanol, ethyl acetate, hexamethylene, acetonitrile, acetone, toluene, dimethylbenzene, dimethyl sulfoxide and N,
The combination in any of N-dimethylformamide.
The preparation method of a kind of chitosan aroma type Schiff the most as claimed in claim 1, it is characterised in that: step (1)
Described in the weight ratio of phenol and oxidant be: 98:2-75:25, the weight ratio of phenol and catalyst: 99:1-90:10.
The preparation method of a kind of chitosan aroma type Schiff the most as claimed in claim 1, it is characterised in that: step (2)
Described in acidic aqueous solution include the combination in any of spirit of vinegar, dilute hydrochloric acid, dilute sulfuric acid and dilute formic acid；Described chitosan solution
Mass fraction is 0.5-20%.
The preparation method of a kind of chitosan aroma type Schiff the most as claimed in claim 1, it is characterised in that: step (1)
With the weight ratio of the phenol described in step (2) with chitosan it is: 5:95-35:65.
The preparation method of a kind of chitosan aroma type Schiff the most as claimed in claim 1, it is characterised in that: step (3)
Described in alkali water-soluble include in sodium hydroxide, sodium carbonate, potassium hydroxide any one；Described pH is 7-10；Institute
The process conditions stated are 20-120 DEG C of oil bath heating, and the response time is 10-240min.
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| CN114635137A (en) * | 2020-12-16 | 2022-06-17 | 华南理工大学 | Organic-inorganic hybrid composite corrosion inhibitor and preparation method and application thereof |
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| US20100239876A1 (en) * | 2009-02-20 | 2010-09-23 | Andre Verville | Chitosan-based adhesives and uses thereof |
| CN101875704A (en) * | 2010-06-25 | 2010-11-03 | 浙江工业大学 | Water-soluble chitosan schiff base derivative and preparation method and application thereof |
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| US20100239876A1 (en) * | 2009-02-20 | 2010-09-23 | Andre Verville | Chitosan-based adhesives and uses thereof |
| CN101875704A (en) * | 2010-06-25 | 2010-11-03 | 浙江工业大学 | Water-soluble chitosan schiff base derivative and preparation method and application thereof |
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| CN114635137A (en) * | 2020-12-16 | 2022-06-17 | 华南理工大学 | Organic-inorganic hybrid composite corrosion inhibitor and preparation method and application thereof |
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Application publication date: 20161116 |