CN104358123A - Preparation method of propionyloxy ethyl trimethyl ammonium chloride chitosan fiber - Google Patents

Preparation method of propionyloxy ethyl trimethyl ammonium chloride chitosan fiber Download PDF

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CN104358123A
CN104358123A CN201410663863.7A CN201410663863A CN104358123A CN 104358123 A CN104358123 A CN 104358123A CN 201410663863 A CN201410663863 A CN 201410663863A CN 104358123 A CN104358123 A CN 104358123A
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chitin fiber
ammonium chloride
trimethyl ammonium
preparation method
propionyloxyethyl
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CN201410663863.7A
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CN104358123B (en
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吕波
许然然
付芳
郑化
雷春雨
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武汉理工大学
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Abstract

The invention relates to a preparation method of propionyloxy ethyl trimethyl ammonium chloride chitosan fiber. The preparation method comprises the steps of dispersing alkalized chitosan fibers in alcohol, and adding with acryloyloxy ethyl trimethyl ammonium chloride for water bath reaction; separating from mixed solution of alcohol and acryloyloxy ethyl trimethyl ammonium chloride to obtain propionyloxy ethyl trimethyl ammonium chloride chitosan fiber; dispersing into organic solvent aqueous solution, dropwise adding acetic acid aqueous solution, adjusting the pH value, oscillating and separating; and washing, and performing centrifugal dewatering and vacuum drying to obtain the propionyloxy ethyl trimethyl ammonium chloride chitosan fiber. The preparation method has the beneficial effects that (1) the polycation characteristic of the chitosan fiber is improved and the antibacterial property of the chitosan fiber is improved; (2) the reacted fiber has the characteristics of high antibacterial property and high liquid absorbing property, and the base form and the integrity of the fiber can be kept after liquid absorbing; and (3) the preparation method of the propionyloxy ethyl trimethyl ammonium chloride chitosan fiber is simple, the cost is low and the method is easy to realize industrial production.

Description

A kind of preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber

Technical field

The present invention relates to a kind of preparation method of chitin fiber, particularly a kind of propionyloxyethyl trimethyl ammonium chloride chitin fiber preparation method, belongs to the preparation field of fibrous material.

Background technology

Chronic wounds as the incidence such as ulcer, bedsore, day by day seriously and year by year improving in the last few years along with aging population.For typical chronic wounds, generally there are 3 features: surface of a wound easy infection; During the surface of a wound has, extremely a large amount of diffusate oozes out; Surface of a wound pain.Although there is dissimilar dressing to be applied to treatment or the nursing of chronic wound clinically, 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 strength are poor.Shitosan, as the second large-tonnage natural polymer in the world, due to its good biocompatibility, biological degradability, biocidal property, there is distinguishing feature especially that be different from other high molecular hemostasis, analgesia, promotion wound healing, suppression scar, be particularly suitable as nursing or the treatment material of this type of surface of a wound.

Shitosan is dissolved in organic acid or inorganic acid or ionic liquid, through spray silk, the obtained chitin fiber such as solidifies, for the preparation of wound dressings such as chronic wounds.China Patent Publication No. is CN103668560A, publication date is on March 26th, 2014, denomination of invention is " a seed shrimp shell prepares the process of chitin fiber ", China Patent Publication No. is CN102199810A, publication date is on September 28th, 2011, denomination of invention is " a kind of preparation method of chitin fiber ", China Patent Publication No. is CN101550610A, publication date is on October 7th, 2009, denomination of invention is " a kind of preparation method of chitin fiber ", China Patent Publication No. is CN101250759, publication date is on August 27th, 2008, denomination of invention discloses the manufacture method of chitin fiber in succession for " medical chitosan fibre and preparation method thereof " etc.But the chitin fiber that these methods prepare still also exists the defects such as antibiotic property is weak, absorbency is poor in chronic wound clinical practice, and effect is not satisfactory, greatly limit its application.

Summary of the invention

For the problems referred to above, the object of the present invention is to provide a kind of technique simple, cost is low, is applicable to the preparation method of the propionyloxyethyl trimethyl ammonium chloride chitin fiber of suitability for industrialized production.

To achieve these goals, its technical scheme is as follows, and a kind of preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber, is characterized in that, carry out according to the following steps:

A) chitin fiber is dispersed in reagent, stirred at ambient temperature, chitin fiber is separated with reagent, vacuumize, obtain the chitin fiber that alkalizes;

B) be dispersed in alcohol by alkalization chitin fiber a) obtained through step, then be that 1:1 ~ 20 add acrylyl oxy-ethyl-trimethyl salmiac by the mol ratio of the amino of alkalization chitin fiber, stirred at ambient temperature is even, and water bath with thermostatic control is reacted;

C) by through step b) mixing material that formed with alcohol, acrylyl oxy-ethyl-trimethyl salmiac of reacted alkalization chitin fiber is separated, and obtains propionyloxyethyl trimethyl ammonium chloride chitin fiber;

D) by through step c) the propionyloxyethyl trimethyl ammonium chloride chitin fiber that obtains is dispersed in the aqueous solution of organic solvent, the aqueous acetic acid dripped, regulate aqueous solutions of organic solvent pH, vibration, then propionyloxyethyl trimethyl ammonium chloride chitin fiber is separated with aqueous solutions of organic solvent, aqueous acetic acid mixed liquor;

E) to through steps d) isolated propionyloxyethyl trimethyl ammonium chloride chitin fiber washing, after centrifugal dehydration, vacuumize, obtains 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, mixing time 1 ~ 12h.

By such scheme, step b) described alcohol is one in methyl alcohol or ethanol or propyl alcohol or butanols or isopropyl alcohol, alkalization chitin fiber and alcohol mass volume ratio are 1:50.

By such scheme, step b) bath temperature be 60 ~ 90 DEG C, reaction time 24 ~ 96h.

By such scheme, steps d) described organic solvent is one in methyl alcohol or ethanol or acetone, the volume ratio of described organic solvent and water is 1:4.

By such scheme, steps d) described pH is adjusted between 6 ~ 8.

Owing to adopting above technical scheme, the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber of the present invention, its Advantageous Effects is:

1) preparation method of the present invention adopts on chitin fiber strand, by the Michael addition reaction of carbon-carbon double bond on amino on chitosan molecule chain and acrylyl oxy-ethyl-trimethyl salmiac molecule, introduce quaternary ammonium salt group, thus increase the polycation characteristic of chitin fiber, improve chitin fiber antibiotic property;

2) by controlling the amino of chitin fiber and the mol ratio of acrylyl oxy-ethyl-trimethyl salmiac and reaction condition, realize the substitution value of propionyloxyethyl trimethyl ammonium chloride chitin fiber within the scope of 20-70%, thus make reacted fiber possess the feature of high antibiotic property and high liquid-absorbing, and grown form and the integrality of fiber after imbibition, can be kept simultaneously; When substitution value is less than 20%, antibiotic property and the absorbency of propionyloxyethyl trimethyl ammonium chloride chitin fiber are all relatively low, and substitution value is when being greater than 80%, hydroxypropyl trimethylammonium trimethyl ammonium chloride chitin fiber after contact diffusate in can not keep the original form of fiber and dissolve, lose structural stability;

3) propionyloxyethyl trimethyl ammonium chloride chitin fiber preparation method of the present invention is simple, and cost is low, easy suitability for industrialized production.The propionyloxyethyl trimethyl ammonium chloride chitin fiber utilizing preparation method of the present invention to prepare has the performance of general traditional fibre, single nonwoven fabric or blending nonwoven fabric can be made by acupuncture nonwoven technique, dressing is formed after sterilizing, for chronic wounds 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, cost are low, 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 described in further detail.

The preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber, preparation method carries out according to the following steps:

A. be that 1:25 is dispersed in pyridine radicals reagent by chitin fiber by mass volume ratio, stirred at ambient temperature 1 ~ 12h, is separated chitin fiber with pyridine radicals reagent, vacuumize, obtains the chitin fiber that alkalizes; Described pyridine radicals reagent is the one in pyridine or picoline.

Chitin fiber be after being dissolved in diluted acid by Chitosan powder through spray silk, solidify, draw the chitin fiber with certain degree of crystallinity that the techniques such as stretching, HEAT SETTING are prepared from.The formation of this chitin fiber degree of crystallinity, mainly by arrangement regular chitosan molecule chain by between strand or molecule intrachain hydrogen bond formed.Therefore, if do not destroy the hydrogen bond of chitosan molecule interchain, open the space between chitosan molecule chain, reactant molecules enters into chitosan molecule chain relevant position, with functional group reactions by being difficult to.So, chitosan molecule interchain or molecule intrachain hydrogen bond must be destroyed before reaction.In patent of the present invention, be exactly with weakly alkaline pyridine radicals agent treated chitin fiber, destroy chitosan molecule interchain or molecule intrachain hydrogen bond with this, its crystalline region content is reduced, and amorphous area and unformed area content increase, and increase the extent of reaction of subsequent reactions with this.

B. the alkalization chitin fiber will obtained through step a, be that 1:50 is dispersed in alcohol by mass volume ratio, be that 1:1 ~ 20 add acrylyl oxy-ethyl-trimethyl salmiac by the mol ratio of amino of alkalization chitin fiber again, stirred at ambient temperature is even, under 60 ~ 90 DEG C of conditions, react 24 ~ 96h in water bath with thermostatic control; Described alcohol is the one in methyl alcohol or ethanol or propyl alcohol or butanols or isopropyl alcohol.

Generally speaking, shitosan in acid condition, the protonated formation polycation of amino energy on chitosan molecule chain, there is certain fungistatic effect, the present invention is the Michael addition reaction by carbon-carbon double bond on amino on chitin fiber strand and acrylyl oxy-ethyl-trimethyl salmiac molecule, quaternary ammonium salt group introduced by chitosan molecule chain, adds the polycation characteristic of chitosan molecule, thus further increase the antibiotic property of chitin fiber.

Step b) in, by controlling amino and acrylyl oxy-ethyl-trimethyl salmiac mol ratio and the reaction condition of chitin fiber, the substitution value carrying out the satisfied propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained is within the scope of 20-70%.Therefore, suitable mol ratio is selected to be: 1:1 ~ 20, reaction temperature 60 ~ 90 DEG C, reaction time 24 ~ 96h.

C. the mixing material formed through the reacted alkalization chitin fiber of step b and alcohol, acrylyl oxy-ethyl-trimethyl salmiac is separated, 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, the volume ratio of organic solvent and water is 1:4, drip the aqueous acetic acid that concentration is 15% (V/V), regulate between aqueous solutions of organic solvent pH to 6 ~ 8, vibration 30min, then propionyloxyethyl trimethyl ammonium chloride chitin fiber is separated with aqueous solutions of organic solvent, aqueous acetic acid mixed liquor; Described organic solvent is the one in methyl alcohol or ethanol or acetone.

Because the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained through step c is alkalescent.Be adjusted between 6 ~ 8 by the aqueous solutions of organic solvent pH value containing propionyloxyethyl trimethyl ammonium chloride chitin fiber, the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained is in neutral.

E. be that 80% (V/V) aqueous solutions of organic solvent washs 3 times to through steps d isolated propionyloxyethyl trimethyl ammonium chloride chitin fiber by concentration again, to remove the small molecular weight impurities such as unreacted reactant acrylyl oxy-ethyl-trimethyl salmiac that fiber contains.After centrifugal dehydration, vacuumize under 40 DEG C of conditions, obtains the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 20-70%.While the propionyloxyethyl trimethyl ammonium chloride chitin fiber obtained possesses high antibiotic property, also can absorb a large amount of liquid, after absorbing fluid, still can 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, when avoiding removing, secondary mechanical damage is formed to the surface of a wound, effectively alleviate sufferer misery.

Embodiment 1

Taking 5g chitin fiber is dispersed in 125mL pyridine, stirred at ambient temperature 1h, is taken out by chitin fiber, vacuumize.By dried chitin fiber, be dispersed in 250mL methyl alcohol, add 5.28g acrylyl oxy-ethyl-trimethyl salmiac, stirred at ambient temperature is even, 24h is reacted in water bath with thermostatic control under 60 DEG C of conditions, reacted chitin fiber is separated with reaction mixture body, and isolated chitin fiber is dispersed in 80% (V/V) methanol aqueous solution, drip 15% (V/V) aqueous acetic acid, by methyl alcohol, aqueous acetic acid pH of mixed is transferred to 7.2, vibration 30min, again the chitin fiber after immersion is separated from mixed liquor, 3 times are washed with 80% (V/V) methanol aqueous solution, after centrifugal dehydration, vacuumize under 40 DEG C of conditions, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 20%.

Embodiment 2

Taking 5g chitin fiber is dispersed in 125mL2-picoline, stirred at ambient temperature 6h, is taken out by chitin fiber, vacuumize.By dried chitin fiber, be dispersed in 250mL ethanol, add 52.8g acrylyl oxy-ethyl-trimethyl salmiac, stirred at ambient temperature is even, 48h is reacted in water bath with thermostatic control under 70 DEG C of conditions, reacted chitin fiber is separated with reaction mixture body, and isolated chitin fiber is dispersed in 80% (V/V) ethanol water, drip 15% (V/V) aqueous acetic acid, by ethanol, aqueous acetic acid pH of mixed is transferred to 6.0, vibration 30min, again the chitin fiber after immersion is separated from mixed liquor, 3 times are washed with 80% (V/V) ethanol water, after centrifugal dehydration, vacuumize under 40 DEG C of conditions, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 46%.

Embodiment 3

Taking 5g chitin fiber is dispersed in 125mL3-picoline, stirred at ambient temperature 12h, is taken out by chitin fiber, vacuumize.By dried chitin fiber, be dispersed in 250mL propyl alcohol, add 105.6g acrylyl oxy-ethyl-trimethyl salmiac, stirred at ambient temperature is even, 72h is reacted in water bath with thermostatic control under 80 DEG C of conditions, reacted chitin fiber is separated with reaction mixture body, and isolated chitin fiber is dispersed in 80% (V/V) aqueous acetone solution, drip 15% (V/V) aqueous acetic acid, by acetone, aqueous acetic acid pH of mixed is transferred to 7.5, vibration 30min, again the chitin fiber after immersion is separated from mixed liquor, 3 times are washed with 80% (V/V) aqueous acetone solution, after centrifugal dehydration, vacuumize under 40 DEG C of conditions, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 52%.

Embodiment 4

Taking 5g chitin fiber is dispersed in 125mL4-picoline, stirred at ambient temperature 12h, is taken out by chitin fiber, vacuumize.By dried chitin fiber, be dispersed in 250mL butanols, add 105.6g acrylyl oxy-ethyl-trimethyl salmiac, stirred at ambient temperature is even, 72h is reacted in water bath with thermostatic control under 90 DEG C of conditions, reacted chitin fiber is separated with reaction mixture body, and isolated chitin fiber is dispersed in 80% (V/V) aqueous acetone solution, drip 15% (V/V) aqueous acetic acid, by acetone, aqueous acetic acid pH of mixed is transferred to 8.0, vibration 30min, again the chitin fiber after immersion is separated from mixed liquor, 3 times are washed with 80% (V/V) aqueous acetone solution, after centrifugal dehydration, vacuumize under 40 DEG C of conditions, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 64%.

Embodiment 5

Taking 5g chitin fiber is dispersed in 125mL pyridine, stirred at ambient temperature 12h, is taken out by chitin fiber, vacuumize.By dried chitin fiber, be dispersed in 250mL isopropyl alcohol, add 105.6g acrylyl oxy-ethyl-trimethyl salmiac, stirred at ambient temperature is even, 96h is reacted in water bath with thermostatic control under 90 DEG C of conditions, reacted chitin fiber is separated with reaction mixture body, and isolated chitin fiber is dispersed in 80% (V/V) methanol aqueous solution, drip 15% (V/V) aqueous acetic acid, by methyl alcohol, aqueous acetic acid pH of mixed is transferred to 7.4, vibration 30min, again the chitin fiber after immersion is separated from mixed liquor, 3 times are washed with 80% (V/V) methanol aqueous solution, after centrifugal dehydration, vacuumize under 40 DEG C of conditions, obtain the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 70%.

The test of obtained propionyloxyethyl trimethyl ammonium chloride chitin fiber anti-microbial property, absorbent is as follows.

(1) antibiotic property

Test bacterial classification selects the common bacterial classification staphylococcus aureus of burn wound.Draw gently with oese and get the above-mentioned wherein a kind of bacterial classification bacterium colony of a ring in 100mL nutrient broth, on 37 DEG C of constant-temperature tables, 150rpm cultivates 18 ~ 24h, and bacteria suspension is diluted to 3.0 × 10 by preparing normal saline 6cFU/mL, in order to antibacterial test.The propionyloxyethyl trimethyl ammonium chloride chitin fiber that above-described embodiment prepares is dissolved with 0.1mol/L HCl, then use in standard NaOH solution and excessive hydrochloric acid, adjust ph, to neutral left and right, makes the propionyloxyethyl trimethyl ammonium chloride chitin fiber dilution of 0.20%.Do blank assay with the NaOH-HCl aqueous solution of same pH, compare experiment with the neutral aqueous solution of the chitin fiber of same pH simultaneously.Getting 1mL bacteria suspension joins in above-mentioned testing sample solution, be placed in 150rpm on 37 DEG C of constant-temperature tables and cultivate 1h, get 0.1mL and make 10 times of gradient dilutions, finally get this liquid of 1mL and make count plate, insert General nutrition agar plate and smoothen, at 37 DEG C, cultivate 24h, observe bacterial growth situation on each sample, calculate average colony number.Its result is 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, the antibiotic rate of embodiment 1 ~ 5 propionyloxyethyl trimethyl ammonium chloride chitin fiber 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 being carded to flocculence fiber through shredding, obtaining nonwoven fabric through rolling dozen sheet, stand-by.

Take 8.3g NaCl and 0.277g CaCl 2adding distil water fully dissolves, and is placed in volumetric flask, and with distilled water constant volume to 1000mL, gained solution is the solution A that British Pharmacopoeia specifies.This solution simulates the content of blood of human body primary metal ion.Get a certain amount of chitin fiber nonwoven fabric, 24h placed by propionyloxyethyl trimethyl ammonium chloride chitin fiber nonwoven fabric, make the regain of fiber reach balance, the dry weight measuring nonwoven fabric is W (g).Take the solution A weighing 40 times than nonwoven fabric, solution and nonwoven fabric being placed on diameter is in the culture dish of 90mm, places 30min for 37 DEG C, clamps the weight in wet base (W taking nonwoven fabric after a jiao of nonwoven fabric hangs 30s aloft with tweezers 1).The hygroscopic capacity of unit mass nonwoven fabric is (W 1-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 hygroscopic capacity of embodiment 1 ~ 5 propionyloxyethyl trimethyl ammonium chloride chitin fiber increases along with the increase of substitution value, is all significantly better than unmodified chitin fiber sample.

More than test shows, propionyloxyethyl trimethyl ammonium chloride chitin fiber of the present invention has the effect of antibacterial, imbibition preferably, and 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 embodiment.Be appreciated that the oher improvements and changes that those skilled in the art directly derive without departing from the spirit and concept in the present invention or associate, all should think and be included within protection scope of the present invention.

The experimental result of table 1 propionyloxyethyl trimethyl ammonium chloride chitin fiber

Claims (7)

1. a preparation method for propionyloxyethyl trimethyl ammonium chloride chitin fiber, is characterized in that, carries out according to the following steps:
A) chitin fiber is dispersed in reagent, stirred at ambient temperature, chitin fiber is separated with reagent, vacuumize, obtain the chitin fiber that alkalizes;
B) be dispersed in alcohol by alkalization chitin fiber a) obtained through step, then be that 1:1 ~ 20 add acrylyl oxy-ethyl-trimethyl salmiac by the mol ratio of the amino of alkalization chitin fiber, stirred at ambient temperature is even, and water bath with thermostatic control is reacted;
C) by through step b) mixing material that formed with alcohol, acrylyl oxy-ethyl-trimethyl salmiac of reacted alkalization chitin fiber is separated, and obtains propionyloxyethyl trimethyl ammonium chloride chitin fiber;
D) by through step c) the propionyloxyethyl trimethyl ammonium chloride chitin fiber that obtains is dispersed in the aqueous solution of organic solvent, the aqueous acetic acid dripped, regulate aqueous solutions of organic solvent pH, vibration, then propionyloxyethyl trimethyl ammonium chloride chitin fiber is separated with aqueous solutions of organic solvent, aqueous acetic acid mixed liquor;
E) to through steps d) isolated propionyloxyethyl trimethyl ammonium chloride chitin fiber washing, after centrifugal dehydration, vacuumize, obtains the propionyloxyethyl trimethyl ammonium chloride chitin fiber that substitution value is 20-70%.
2. the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber according to claim 1, is characterized in that: described reagent is pyridine radicals reagent, and described pyridine radicals reagent is the one in pyridine or picoline.
3. the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber according to claim 2, is characterized in that: chitin fiber and pyridine radicals reagent are that 1:25 (g:mL) disperses by mass volume ratio, mixing time 1 ~ 12h.
4. the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber according to claim 1, it is characterized in that: step b) described alcohol is one in methyl alcohol or ethanol or propyl alcohol or butanols or isopropyl alcohol, alkalization chitin fiber and alcohol mass volume ratio are 1:50 (g:mL).
5. the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber according to claim 1, is characterized in that: step b) bath temperature be 60 ~ 90 DEG C, reaction time 24 ~ 96h.
6. the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber according to claim 1, is characterized in that: steps d) described organic solvent is one in methyl alcohol or ethanol or acetone, the volume ratio of described organic solvent and water is 1:4.
7. the preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber according to claim 1, is characterized in that: steps d) described pH is adjusted between 6 ~ 8.
CN201410663863.7A 2014-11-19 2014-11-19 A kind of preparation method of propionyloxyethyl trimethyl ammonium chloride chitin fiber CN104358123B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19544455A1 (en) * 1995-11-29 1997-06-05 Henkel Kgaa Biological treatment of waste water
JP2002346572A (en) * 2001-05-22 2002-12-03 Ebara Corp Clean water treatment method and treatment agent
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19544455A1 (en) * 1995-11-29 1997-06-05 Henkel Kgaa Biological treatment of waste water
JP2002346572A (en) * 2001-05-22 2002-12-03 Ebara Corp Clean water treatment method and treatment agent
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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