CN104358123B - A kind of preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber - Google Patents
A kind of preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber Download PDFInfo
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- CN104358123B CN104358123B CN201410663863.7A CN201410663863A CN104358123B CN 104358123 B CN104358123 B CN 104358123B CN 201410663863 A CN201410663863 A CN 201410663863A CN 104358123 B CN104358123 B CN 104358123B
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Abstract
The present invention relates to propionyloxyethyl trimethyl ammonium chloride chitin fiber preparation method, alkalization chitin fiber is dispersed in alcohol, add acrylyl oxy-ethyl-trimethyl salmiac, water-bath；The mixing liquid formed with alcohol, acrylyl oxy-ethyl-trimethyl salmiac separates, and obtains propionyloxyethyl trimethyl ammonium chloride chitin fiber；It is dispersed in the aqueous solution of organic solvent, the aqueous acetic acid of dropping, regulates pH, vibration, separate；Washing, after centrifugal dehydration, vacuum drying, obtain propionyloxyethyl trimethyl ammonium chloride chitin fiber, Advantageous Effects is: 1) increase the polycation characteristic of chitin fiber, improves chitin fiber antibiotic property；2) reacted fiber is provided simultaneously with the feature of high antibiotic property and high liquid-absorbing, and can keep grown form and the integrality of fiber after imbibition；3) the propionyloxyethyl trimethyl ammonium chloride chitin fiber preparation method of the present invention is simple, low cost, easy industrialized production.
Description
Technical field
The present invention relates to the preparation method of a kind of chitin fiber, particularly a kind of propionyloxyethyl trimethyl ammonium chloride shitosan
Fiber producing processes, belongs to the preparation field of fibrous material.
Background technology
The chronic wounds such as incidence such as ulcer, bedsore, the most seriously and year by year carrying along with aging population in the last few years
High.For typical chronic wounds, typically there are 3 features: surface of a wound easy infection；The surface of a wound have in oozing in a large number
Go out liquid to ooze out；Surface of a wound pain.Although have different types of dressing to be applied to treatment or the nursing of chronic wound clinically, but all
Not fully up to expectations, there are some defects to some extent, as weak in anti-infective performance, drug allergy, absorption sepage ability, wet
State intensity is poor.Shitosan, as the in the world second large-tonnage natural polymer, due to its good biocompatibility,
Biological degradability, biocidal property, have especially be different from other high molecular hemostasis, ease pain, promote wound healing, suppression scar
Distinguishing feature, be particularly suitable as this type of surface of a wound nursing or treatment material.
Dissolve the chitosan in organic acid or inorganic acid or ionic liquid, through the prepared chitin fiber such as spinneret, solidification, be used for
Prepare the wound dressings such as chronic wound.China Patent Publication No. is CN103668560A, and publication date is on March 26th, 2014,
Invention entitled the process of chitin fiber " the seed shrimp shell prepare ", China Patent Publication No. are CN102199810A, public
Opening day is on September 28th, 2011, and invention entitled " preparation method of a kind of chitin fiber ", China Patent Publication No. are
CN101550610A, publication date is on October 7th, 2009, invention entitled " preparation method of a kind of chitin fiber ",
China Patent Publication No. is CN101250759, and publication date is on August 27th, 2008, and invention entitled " medical chitosan is fine
Dimension and preparation method thereof " etc. in succession disclose the manufacture method of chitin fiber.But, the shitosan that these methods prepare
Fiber still also exists the defects such as antibiotic property is weak, absorbency is poor in chronic wound clinical practice, and effect is not satisfactory, the day of one's doom
Make its application.
Summary of the invention
For the problems referred to above, it is an object of the invention to provide a kind of technique simple, low cost, it is suitable for the propionyl of industrialized production
The preparation method of epoxide ethyl-trimethyl salmiac chitin fiber.
To achieve these goals, its technical scheme is as follows, the system of a kind of propionyloxyethyl trimethyl ammonium chloride chitin fiber
Preparation Method, it is characterised in that sequentially include the following steps:
A) chitin fiber is dispersed in reagent, stirs under room temperature, chitin fiber is separated with reagent, vacuum drying,
To alkalization chitin fiber；
B) the alkalization chitin fiber obtained through step a) is dispersed in alcohol, then by alkalization chitin fiber amino mole
Adding acrylyl oxy-ethyl-trimethyl salmiac than for 1:1～20, stir under room temperature, water bath with thermostatic control is reacted；
C) mixing that will be formed through step b) reacted alkalization chitin fiber and alcohol, acrylyl oxy-ethyl-trimethyl salmiac
Liquid separates, and obtains propionyloxyethyl trimethyl ammonium chloride chitin fiber；
D) the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained through step c) is dispersed in the aqueous solution of organic solvent
In, the aqueous acetic acid of dropping, regulate aqueous solutions of organic solvent pH, vibrate, then by propionyloxyethyl trimethyl ammonium chloride shell
Glycan fiber separates with aqueous solutions of organic solvent, aqueous acetic acid mixed liquor；
E) wash through step d) isolated propionyloxyethyl trimethyl ammonium chloride chitin fiber, after centrifugal dehydration, very
Empty dry, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 20-70%.
By such scheme, described reagent is pyridine radicals reagent, and described pyridine radicals reagent is the one in pyridine or picoline.
By such scheme, chitin fiber and pyridine radicals reagent are that 1:25 (g:mL) disperses by mass volume ratio, stirring
Time 1～12h.
By such scheme, the described alcohol of step b) is the one in methyl alcohol or ethanol or propyl alcohol or butanol or isopropanol, and alkalization shell gathers
Sugar fiber is 1:50 with alcohol mass volume ratio.
By such scheme, the bath temperature of step b) is 60～90 DEG C, the reaction time 24～96h.
By such scheme, the described organic solvent of step d) is the one in methyl alcohol or ethanol or acetone, described organic solvent and water
Volume ratio be 1:4.
By such scheme, the described pH of step d) regulates between 6～8.
Owing to using above technical scheme, the preparation method of the propionyloxyethyl trimethyl ammonium chloride chitin fiber of the present invention,
Its Advantageous Effects is:
1) preparation method of the present invention uses on chitin fiber strand, by amino and acryloyl-oxy on chitosan molecule chain
The Michael addition reaction of carbon-carbon double bond on ethyl-trimethyl salmiac molecule, introduces quaternary ammonium salt group, thus it is fine to increase shitosan
The polycation characteristic of dimension, improves chitin fiber antibiotic property；
2) by the amino of control chitin fiber and the mol ratio of acrylyl oxy-ethyl-trimethyl salmiac and reaction condition, come
Realize the substitution value of propionyloxyethyl trimethyl ammonium chloride chitin fiber in the range of 20-70%, so that reacted fibre
Dimension is provided simultaneously with the feature of high antibiotic property and high liquid-absorbing, and can keep grown form and the integrality of fiber after imbibition；Replace
When degree is less than 20%, antibiotic property and the absorbency of propionyloxyethyl trimethyl ammonium chloride chitin fiber are the most relatively low, and take
When Dai Du is more than 80%, hydroxypropyl trimethylammonium trimethyl ammonium chloride chitin fiber can not keep fiber in contacting after diffusate
Original form and dissolve, lose structural stability；
3) the propionyloxyethyl trimethyl ammonium chloride chitin fiber preparation method of the present invention is simple, low cost, easily industry metaplasia
Produce.The propionyloxyethyl trimethyl ammonium chloride chitin fiber utilizing preparation method of the present invention to prepare has general traditional fibre
Performance, can make single non-woven fabrics or blending non-woven fabrics by acupuncture nonwoven technique, sterilized after form dressing, for chronic
Difficult the healing surface of a wound such as burn and scald, bedsore etc., play and kill surface of a wound bacterium, absorb wound fluid, the effect of wound healing,
And steady quality, low cost, easy to use.
Detailed description of the invention
Below in conjunction with specific embodiment, propionyloxyethyl trimethyl ammonium chloride chitin fiber preparation method of the present invention is made further
Describe in detail.
The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber, preparation method sequentially includes the following steps:
A. it is that 1:25 is dispersed in pyridine radicals reagent by chitin fiber by mass volume ratio, under room temperature, stirs 1～12h, will
Chitin fiber separates with pyridine radicals reagent, vacuum drying, obtains the chitin fiber that alkalizes；Described pyridine radicals reagent be pyridine or
One in picoline.
Chitin fiber be dissolved in diluted acid by Chitosan powder after through spinneret, solidify, draw the techniques such as stretching, thermal finalization and prepare
The chitin fiber with certain degree of crystallinity.The formation of this chitin fiber degree of crystallinity, mainly by the shell that arrangement is regular
Glycan molecule chain is formed by molecule interchain or molecule intrachain hydrogen bond.Therefore, if not destroying the hydrogen of chitosan molecule interchain
Key, opens the space between chitosan molecule chain, and reactant molecules would become hard to enter into chitosan molecule chain relevant position, with
Functional group reactions.So, chitosan molecule interchain or molecule intrachain hydrogen bond must be destroyed before reaction.In patent of the present invention, just
It is with weakly alkaline pyridine radicals agent treatment chitin fiber, destroys chitosan molecule interchain or molecule intrachain hydrogen bond with this so that it is
Crystalline region content reduces, and the i.e. unformed area content of amorphous area increases, and increases the extent of reaction of subsequent reactions with this.
B. the alkalization chitin fiber that will obtain through step a, is that 1:50 is dispersed in alcohol by mass volume ratio, then by alkalization shell
The mol ratio of the amino of glycan fiber is that 1:1～20 adds acrylyl oxy-ethyl-trimethyl salmiac, stirs under room temperature,
Water bath with thermostatic control is reacted under the conditions of 60～90 DEG C 24～96h；Described alcohol is in methyl alcohol or ethanol or propyl alcohol or butanol or isopropanol
A kind of.
It is said that in general, shitosan is in acid condition, on chitosan molecule chain, amino can protonate formation polycation, has one
Fixed fungistatic effect, the present invention is by amino on chitin fiber strand and acrylyl oxy-ethyl-trimethyl salmiac molecule
The Michael addition reaction of carbon-carbon double bond, introduces quaternary ammonium salt group on chitosan molecule chain, adds the poly-sun of chitosan molecule
Ion characteristic, thus further increase the antibiotic property of chitin fiber.
In step b), by controlling amino and acrylyl oxy-ethyl-trimethyl salmiac mol ratio and the reaction of chitin fiber
Condition, meets in the range of the substitution value of the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained is 20-70%.Therefore,
The suitable mol ratio is selected to be: 1:1～20, reaction temperature 60～90 DEG C, reaction time 24～96h.
C. the mixed liquor that will be formed through step b reacted alkalization chitin fiber and alcohol, acrylyl oxy-ethyl-trimethyl salmiac
Body separates, and obtains propionyloxyethyl trimethyl ammonium chloride chitin fiber；
D. the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained through step c is dispersed in aqueous solutions of organic solvent,
Organic solvent is 1:4 with the volume ratio of water, and dropping concentration is the aqueous acetic acid of 15% (V/V), regulates aqueous solutions of organic solvent
Between pH to 6～8, vibrate 30min, then by propionyloxyethyl trimethyl ammonium chloride chitin fiber and aqueous solutions of organic solvent,
Aqueous acetic acid mixed liquor separates；Described organic solvent is the one in methyl alcohol or ethanol or acetone.
Owing to the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained by step c is alkalescent.Will be containing propionyl oxygen
The aqueous solutions of organic solvent pH value regulation of base ethyl-trimethyl salmiac chitin fiber between 6～8, the propionyloxy obtained
Ethyl-trimethyl salmiac chitin fiber is neutrality.
It is that 80% (V/V) aqueous solutions of organic solvent is to through step d isolated propionyloxyethyl trimethyl chlorine by concentration the most again
Change ammonium chitin fiber to wash 3 times, to remove little point of the unreacted reactant acrylyl oxy-ethyl-trimethyl salmiac that contains on fiber etc.
Sub-impurity.After centrifugal dehydration, it is vacuum dried under the conditions of 40 DEG C, obtains the propionyloxyethyl trimethyl that substitution value is 20-70%
Ammonium chloride chitin fiber.While the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained possesses high antibiotic property, also
Substantial amounts of liquid can be absorbed, remain to after absorbing liquid keep fiber grown form, form fiber gel.When it is applied to the surface of a wound,
Easily peel off from the surface of a wound, it is to avoid during removal, the surface of a wound is formed secondary mechanical damage, effectively alleviates sufferer painful.
Embodiment 1
Weighing 5g chitin fiber to be dispersed in 125mL pyridine, stir 1h, taken out by chitin fiber under room temperature, vacuum is done
Dry.By dried chitin fiber, it is dispersed in 250mL methyl alcohol, adds 5.28g acrylyl oxy-ethyl-trimethyl salmiac,
Stir under room temperature, water bath with thermostatic control is reacted under the conditions of 60 DEG C 24h, by reacted chitin fiber and reaction mixture
Body separates, and is dispersed in by isolated chitin fiber in 80% (V/V) methanol aqueous solution, drips 15% (V/V) acetic acid water
Solution, is transferred to 7.2 by methyl alcohol, aqueous acetic acid pH of mixed, and vibrate 30min, then the chitin fiber after soaking is from mixed
Close in liquid and separate, wash 3 times with 80% (V/V) methanol aqueous solution, after centrifugal dehydration, be vacuum dried under the conditions of 40 DEG C,
Obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 20%.
Embodiment 2
Weigh 5g chitin fiber to be dispersed in 125mL2-picoline, stir 6h under room temperature, chitin fiber is taken out,
Vacuum drying.By dried chitin fiber, it is dispersed in 250mL ethanol, adds 52.8g acrylyl oxy-ethyl-trimethyl
Ammonium chloride, stirs under room temperature, reacts 48h, by reacted chitin fiber with anti-under the conditions of 70 DEG C in water bath with thermostatic control
Liquid should be mixed separate, and isolated chitin fiber is dispersed in 80% (V/V) ethanol water, drip 15% (V/V)
Aqueous acetic acid, is transferred to 6.0 by ethanol, aqueous acetic acid pH of mixed, and vibrate 30min, then the shitosan after soaking is fine
Dimension is separated from mixed liquor, washs 3 times with 80% (V/V) ethanol water, after centrifugal dehydration, true under the conditions of 40 DEG C
Empty dry, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 46%.
Embodiment 3
Weigh 5g chitin fiber to be dispersed in 125mL3-picoline, stir 12h under room temperature, chitin fiber is taken out,
Vacuum drying.By dried chitin fiber, it is dispersed in 250mL propyl alcohol, adds 105.6g acrylyl oxy-ethyl-trimethyl
Ammonium chloride, stirs under room temperature, reacts 72h, by reacted chitin fiber with anti-under the conditions of 80 DEG C in water bath with thermostatic control
Liquid should be mixed separate, and isolated chitin fiber is dispersed in 80% (V/V) aqueous acetone solution, drip 15% (V/V)
Aqueous acetic acid, is transferred to 7.5 by acetone, aqueous acetic acid pH of mixed, and vibrate 30min, then the shitosan after soaking is fine
Dimension is separated from mixed liquor, washs 3 times with 80% (V/V) aqueous acetone solution, after centrifugal dehydration, true under the conditions of 40 DEG C
Empty dry, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 52%.
Embodiment 4
Weigh 5g chitin fiber to be dispersed in 125mL4-picoline, stir 12h under room temperature, chitin fiber is taken out,
Vacuum drying.By dried chitin fiber, it is dispersed in 250mL butanol, adds 105.6g acrylyl oxy-ethyl-trimethyl
Ammonium chloride, stirs under room temperature, reacts 72h, by reacted chitin fiber with anti-under the conditions of 90 DEG C in water bath with thermostatic control
Liquid should be mixed separate, and isolated chitin fiber is dispersed in 80% (V/V) aqueous acetone solution, drip 15% (V/V)
Aqueous acetic acid, is transferred to 8.0 by acetone, aqueous acetic acid pH of mixed, and vibrate 30min, then the shitosan after soaking is fine
Dimension is separated from mixed liquor, washs 3 times with 80% (V/V) aqueous acetone solution, after centrifugal dehydration, true under the conditions of 40 DEG C
Empty dry, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 64%.
Embodiment 5
Weighing 5g chitin fiber to be dispersed in 125mL pyridine, stir 12h, taken out by chitin fiber under room temperature, vacuum is done
Dry.By dried chitin fiber, it is dispersed in 250mL isopropanol, adds 105.6g acrylyl oxy-ethyl-trimethyl chlorination
Ammonium, stirs under room temperature, reacts 96h under the conditions of 90 DEG C in water bath with thermostatic control, by mixed to reacted chitin fiber and reaction
Conjunction liquid separates, and is dispersed in by isolated chitin fiber in 80% (V/V) methanol aqueous solution, drips 15% (V/V) vinegar
Aqueous acid, is transferred to 7.4 by methyl alcohol, aqueous acetic acid pH of mixed, and vibrate 30min, then the chitin fiber after soaking
Separate from mixed liquor, wash 3 times with 80% (V/V) methanol aqueous solution, after centrifugal dehydration, vacuum under the conditions of 40 DEG C
It is dried, obtains the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 70%.
Obtained propionyloxyethyl trimethyl ammonium chloride chitin fiber anti-microbial property, absorbent test are as follows.
(1) antibiotic property
Test bacterial classification selects burn wound common bacterial classification staphylococcus aureus.Draw gently with oese and take an above-mentioned one of which of ring
Bacterial classification bacterium colony is in 100mL nutrient broth, and on 37 DEG C of constant-temperature tables, 150rpm cultivates 18～24h, and preparing normal saline will
Bacteria suspension is diluted to 3.0 × 106CFU/mL, in case antibacterial test.Dissolve above-described embodiment with 0.1mol/L HCl to prepare
Propionyloxyethyl trimethyl ammonium chloride chitin fiber, then with in standard NaOH solution and excessive hydrochloric acid, regulate pH value
To neutrality, make the propionyloxyethyl trimethyl ammonium chloride chitin fiber dilution of 0.20%.With same pH
The NaOH-HCl aqueous solution do blank assay, compare experiment with the neutral aqueous solution of the chitin fiber of same pH simultaneously.
Take 1mL bacteria suspension to join in above-mentioned testing sample solution, be placed in 150rpm on 37 DEG C of constant-temperature tables and cultivate 1h, take 0.1mL and make
10 times of gradient dilutions, finally take this liquid of 1mL and make count plate, insert General nutrition agar plate and smoothen, and train at 37 DEG C
Support 24h, observe bacterial growth situation on each sample, calculate average colony number.Its result such as table 1.
Table 1 data show embodiment 1～5 propionyloxyethyl trimethyl ammonium chloride chitin fiber, chitin fiber control group
Antibiotic rate experimental result.Experiment results proved, embodiment 1～5 propionyloxyethyl trimethyl ammonium chloride chitin fiber antibacterial
Rate increases along with the increase of substitution value, is all significantly better than unmodified chitin fiber sample.
(2) absorbency
Propionyloxyethyl trimethyl ammonium chloride chitin fiber is carded to flocculence fiber through shredding, prepares nothing through rolling dozen sheet
Spin cloth, stand-by.
Weigh 8.3g NaCl and 0.277g CaCl2Add distilled water fully to dissolve, be placed in volumetric flask, with distilled water constant volume to 1000
ML, gained solution is the solution A that British Pharmacopoeia specifies.This solution simulates the content of blood of human body primary metal ion.Take one
24h placed by quantitative chitin fiber non-woven fabrics, propionyloxyethyl trimethyl ammonium chloride chitin fiber non-woven fabrics, makes fiber
Regain reach balance, measure non-woven fabrics dry weight be W (g).Weigh the solution A than non-woven fabrics weight 40 times, by solution
With in the culture dish that non-woven fabrics is placed on a diameter of 90mm, place 30min, clamp one jiao of non-woven fabrics at sky with tweezers for 37 DEG C
Weight in wet base (the W of non-woven fabrics is weighed after middle extension 30s1).The hygroscopic capacity of unit mass non-woven fabrics is (W1-W)/W.The results are shown in Table 1.
Table 1 data show embodiment 1～5 propionyloxyethyl trimethyl ammonium chloride chitin fiber, chitin fiber control group
Absorbency experimental result.Experiment results proved, the moisture absorption of embodiment 1～5 propionyloxyethyl trimethyl ammonium chloride chitin fiber
Amount increases along with the increase of substitution value, is all significantly better than unmodified chitin fiber sample.
More than test shows, the propionyloxyethyl trimethyl ammonium chloride chitin fiber of the present invention has the most antibacterial, imbibition
Effect, the new medical products prepared with it, market prospects are boundless.
Above-described is only the preferred embodiment of the present invention, the invention is not restricted to above example.It is appreciated that this area
The oher improvements and changes that technical staff the most directly derives or associates, all should
Think within being included in protection scope of the present invention.
The experimental result of table 1 propionyloxyethyl trimethyl ammonium chloride chitin fiber
Claims (6)
1. the preparation method of a propionyloxyethyl trimethyl ammonium chloride chitin fiber, it is characterised in that enter according to the following steps
OK:
A) chitin fiber is dispersed in reagent, stirs under room temperature, chitin fiber is separated with reagent, vacuum drying,
To alkalization chitin fiber；
B) being dispersed in alcohol by the alkalization chitin fiber obtained through step a), described alcohol is methyl alcohol or ethanol or propyl alcohol or butanol
Or the one in isopropanol, alkalization chitin fiber is 1g:50mL with alcohol mass volume ratio；Again by alkalization chitin fiber
The mol ratio of amino is that 1:1～20 adds acrylyl oxy-ethyl-trimethyl salmiac, stirs under room temperature, and water bath with thermostatic control is reacted；
C) mixing that will be formed through step b) reacted alkalization chitin fiber and alcohol, acrylyl oxy-ethyl-trimethyl salmiac
Liquid separates, and obtains propionyloxyethyl trimethyl ammonium chloride chitin fiber；
D) the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained through step c) is dispersed in the aqueous solution of organic solvent
In, the aqueous acetic acid of dropping, regulate aqueous solutions of organic solvent pH, vibrate, then by propionyloxyethyl trimethyl ammonium chloride shell
Glycan fiber separates with aqueous solutions of organic solvent, aqueous acetic acid mixed liquor；
E) wash through step d) isolated propionyloxyethyl trimethyl ammonium chloride chitin fiber, after centrifugal dehydration, very
Empty dry, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 20-70%.
The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber the most according to claim 1, it is characterised in that:
Described reagent is pyridine radicals reagent, and described pyridine radicals reagent is the one in pyridine or picoline.
The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber the most according to claim 2, it is characterised in that:
Chitin fiber and pyridine radicals reagent are that 1g:25mL disperses by mass volume ratio, mixing time 1～12h.
The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber the most according to claim 1, it is characterised in that:
The bath temperature of step b) is 60～90 DEG C, the reaction time 24～96h.
The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber the most according to claim 1, it is characterised in that:
The described organic solvent of step d) is the one in methyl alcohol or ethanol or acetone, and described organic solvent is 1:4 with the volume ratio of water.
The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber the most according to claim 1, it is characterised in that:
The described pH of step d) regulates between 6～8.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19544455A1 (en) * | 1995-11-29 | 1997-06-05 | Henkel Kgaa | Biological treatment of waste water |
| CN1833732A (en) * | 2005-03-17 | 2006-09-20 | 李毅彬 | Making method of and use of antibiotic surgical dressing |
| CN103387279A (en) * | 2013-08-13 | 2013-11-13 | 南京大学 | Chemical bond connected strong cationic grafted amphoteric chitosan flocculant and preparation method thereof |
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| JP4004016B2 (en) * | 2001-05-22 | 2007-11-07 | 株式会社荏原製作所 | Water treatment method |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19544455A1 (en) * | 1995-11-29 | 1997-06-05 | Henkel Kgaa | Biological treatment of waste water |
| CN1833732A (en) * | 2005-03-17 | 2006-09-20 | 李毅彬 | Making method of and use of antibiotic surgical dressing |
| CN103387279A (en) * | 2013-08-13 | 2013-11-13 | 南京大学 | Chemical bond connected strong cationic grafted amphoteric chitosan flocculant and preparation method thereof |
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