CN107261201A - A kind of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt and preparation method thereof - Google Patents
A kind of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt and preparation method thereof Download PDFInfo
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- CN107261201A CN107261201A CN201710532944.7A CN201710532944A CN107261201A CN 107261201 A CN107261201 A CN 107261201A CN 201710532944 A CN201710532944 A CN 201710532944A CN 107261201 A CN107261201 A CN 107261201A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/008—Hydrogels or hydrocolloids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0023—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/0066—Medicaments; Biocides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
- A61L2300/208—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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Abstract
The present invention relates to a kind of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt and preparation method thereof, comprise the following steps：The high polymer of the unit containing agarobiose is added in hot water and stirred until being completely dissolved, appropriate initiator potassium peroxydisulfate and monomer MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride are added into solution, reaction solution is stirred 6 hours for 90 DEG C in nitrogen atmosphere, is cooled to after room temperature gained gel being fixed on immersion removing impurity in distilled water.The agarose for the macromolecular quaternary ammonium salt grafting that the present invention is prepared has good biocompatibility, by that can form gel antiseptic dressing after heating for dissolving, die casting, solidification.In vitro Bactericidal Experiments result show this invention can effectively bacteria growing inhibiting and can kill biomedical material surface attachment bacterium.Experiment made on the living shows that this invention can significantly cure infection of staphylococcus aureus and promote Rat Wound Healing.
Description
Technical field
The invention belongs to anti-biotic material field, be related to a kind of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt and
Its preparation method.
Background technology
Due to people's abuse, antibiotic is excessively used, certain drug resistance have occurred in some bacteriums, and this directly results in
The increase of medical expense, complication is frequently occurred, or even causes death.Therefore, what searching was new is not likely to produce resistance
The antiseptic of property becomes particularly important.
At present, quaternary ammonium salt is a kind of cationic antiseptic, its Antibacterial Mechanism be mainly quaternary ammonium salt contacted with bacterium and
Its cell membrane is penetrated into, then react destruction cell membrane with bacterial cell membrane, further effect causes protein, nucleic acid
Decompose, intercellular substance leakage, last cell wall lysis, so as to realize antibacterial action.Quaternary ammonium salt antiseptic is not produced generally
Bacterial drug resistance, therefore increasingly paid close attention to by researcher and Production Engineer.
In daily life, most of quaternary ammonium salt antiseptic is organic molecule or high polymer material, is entered in fluid form
Row bactericidal action.For the antifouling grade medical application of medical apparatus surface, the antiseptic that liquid form is present is unfavorable for for a long time
Effectively maintain antibacterial functions.For the wound healing such as wound care and scald, burn, the antiseptic that liquid form is present is more
It is to be difficult to use.It is the effective ways for solving its problem that quaternary ammonium salt antibacterial combination, which is embedded in inside dressing,.The quaternary ammonium of embedding
Salt antiseptic can play effect long-term effectively, and not produce leakage to surrounding tissue organ and the bad shadow of environment generation
Ring.
The content of the invention
In view of this, it is an object of the invention to provide one kind based on macromolecular quaternary ammonium salt be grafted agarose antiseptic dressing and
Its preparation method, to reach above-mentioned purpose, the present invention provides following technical scheme：
1. a kind of preparation method for the agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt, is comprised the following steps：
1) high polymer of the unit containing agarobiose is added to the water stirring until being completely dissolved；
2) toward step 1) initiator and quaternary ammonium salt monomer, the initiator, quaternary ammonium salt monomer and fine jade are added in solution
The mol ratio of fat disaccharide unit is 0.25:10:1~0.25:50:1；
3) by step 2) reaction solution under atmosphere of inert gases 85~95 DEG C stir 3~9 hours；
4) by step 3) in reaction solution pour into beaker and be cooled to room temperature, the gelatinous solid of formation is dialysed with distilled water
Impurity is removed, the agarose of macromolecular quaternary ammonium salt grafting is obtained；
5) by step 4) obtained by the grafting of macromolecular quaternary ammonium salt agarose by dissolving by heating, die casting and cooling it is solid
Change prepares antiseptic dressing.
Further, step 2) the quaternary ammonium salt monomer be polymethyl acyloxyethyl trimethyl ammonium chloride, containing quaternary ammonium
Phenylethylene, acrylic amide, methacryl amine, esters of acrylic acid or the third vinyl monomer of salt.
Further, the quaternary ammonium salt monomer is polymethyl acyloxyethyl trimethyl ammonium chloride.
Further, step 1) high polymer of the unit containing agarobiose is agarose, the natural extraction containing agarose
One or more in thing, agarose derivative, gelatin or carragheen.
Further, step 2) initiator be potassium peroxydisulfate, azodiisobutyronitrile, ammonium persulfate or azo dicyano penta
Acid.
Further, the initiator is potassium peroxydisulfate.
2. the antiseptic dressing prepared using above-mentioned preparation method, the agarose of the macromolecular quaternary ammonium salt grafting
Structural formula is：
Wherein, the positive integer of m=300~500, the positive integer of n=10~50.
The beneficial effects of the present invention are：The agarose of macromolecular quaternary ammonium salt grafting prepared by the present invention has good life
Thing compatibility, and gel antiseptic dressing can be formed.Macromolecular is made using free yl graft polymerization " one-step method " in the present invention
The agarose of quaternary ammonium salt grafting, the method is simple to operate, uses low in raw material price to be easy to get, by increasing capacitance it is possible to increase practicality of the invention
Property.Antiseptic dressing of the present invention has good biocompatibility, not only can also kill biology with bacteria growing inhibiting
The bacterium of medical material surface attachment, antiseptic dressing of the invention can both be covered in medical apparatus surface to prevent microorganism attached
And infect, bacterium and wound healing that the surface of a wound is infected can be killed again.The antiseptic dressing invented is applied to gold
The rat surface of a wound of staphylococcus aureus infection, can cure bacterium infection and accelerate wound healing.
Brief description of the drawings
In order that the purpose of the present invention, technical scheme and beneficial effect are clearer, the present invention provides drawings described below and carried out
Explanation：
Fig. 1 is grafted the route map of agarose for synthesis polymethyl acyloxyethyl trimethyl ammonium chloride.
Fig. 2 be antiseptic dressing in Bactericidal test to staphylococcus aureus, MRSE, Escherichia coli and green
Purulence bacillus forms the diameter figure of inhibition zone.
Fig. 3 is the bacterial number variation diagram before and after the titanium plate surface antiseptic dressing covering of bacterium infection.
Embodiment
Below in conjunction with accompanying drawing, the preferred embodiments of the present invention are described in detail.
The synthetic route for the agarose being grafted based on macromolecular quaternary ammonium salt is as shown in figure 1, agarose, initiator potassium persulfate
Reacted with MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride monomer, one-step method obtains polymethyl acyloxyethyl trimethyl
The agarose of ammonium chloride grafting.
Embodiment 1
It is 1 liter of three-necked bottle that 15 grams of agaroses and 500 milliliters of distilled water, which are added to equipped with mechanical agitation, volume, then,
Agarose suspension is heated in 95 degree of oil bath pan until being completely dissolved.Under nitrogen protection, toward sequentially adding in reaction solution
3.3 grams of potassium peroxydisulfates and 125 milliliters of MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride 80wt% aqueous solution.Mixed liquor is at 90 DEG C
Oil bath pan in stirring 6 hours after pour into beaker, naturally cool to and gelatinous solid formed after room temperature.Gained solid is through repeatedly
Distilled water immersion obtains invented macromolecular quaternary ammonium salt grafting agarose, heated dissolving, die casting, cooling and shaping processing
It is remolded, required antiseptic dressing has been prepared.
Embodiment 2
It is 1 liter of three-necked bottle that 15 grams of agaroses and 500 milliliters of distilled water, which are added to equipped with mechanical agitation, volume, then,
Agarose suspension is heated in 95 degree of oil bath pan until being completely dissolved.Under nitrogen protection, toward sequentially adding in reaction solution
3.3 grams of potassium peroxydisulfates and 62.5 milliliters of MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride 80wt% aqueous solution.Mixed liquor is 90
DEG C oil bath pan in stirring pour into beaker after 6 hours, it is purified obtain invention antiseptic dressing.
Embodiment 3
It is 1 liter of three-necked bottle that 15 grams of agaroses and 500 milliliters of distilled water, which are added to equipped with mechanical agitation, volume, then,
Agarose suspension is heated in 95 DEG C of oil bath pan until being completely dissolved.Under nitrogen protection, toward sequentially adding in reaction solution
3.3 grams of potassium peroxydisulfates and 125 milliliters of MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride 80wt% aqueous solution.Mixed liquor is at 80 DEG C
Oil bath pan in stirring pour into beaker after 6 hours, it is purified obtain invention antiseptic dressing.
Embodiment 4
It is 1 liter of three-necked bottle that 15 grams of agaroses and 500 milliliters of distilled water, which are added to equipped with mechanical agitation, volume, then,
Agarose suspension is heated in 95 DEG C of oil bath pan until being completely dissolved.Under nitrogen protection, toward sequentially adding in reaction solution
1.7 grams of potassium peroxydisulfates and 125 milliliters of MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride 80wt% aqueous solution.Mixed liquor is at 90 DEG C
Oil bath pan in stirring pour into beaker after 6 hours, it is purified obtain invention antiseptic dressing.
Embodiment 5
A diameter of 2 centimetres of antiseptic dressing is covered in the agar plate of bacterium even spread, agar plate is positioned over 37 degree
Incubator measures antibacterial circle diameter after 24 hours with ruler.Fig. 2 show antiseptic dressing in Bactericidal test to golden yellow Portugal
Grape coccus, MRSE, Escherichia coli and Pseudomonas aeruginosa form the diameter of inhibition zone.From figure 2 it can be seen that
Antiseptic dressing can significantly suppress the growth of Gram-positive and negative bacterium.
Embodiment 6
By antiseptic dressing, it uses phosphate buffer solution (pH 7.4) rinse 3 times after taking out and back-off is in antiseptic dressing surface,
After 37 degree of incubator cultures 24 hours, antiseptic dressing processing and untreated titanium sheet pass through coated plate and count standard measure surface attachment
Bacterium, medical titanium sheet (1 1 centimetre of cm x) is soaked in ten seven power bacterial solution 4 hours.Fig. 3 show bacterium infection
Titanium plate surface the present invention prepare antiseptic dressing covering before and after bacterial number change.From figure 3, it can be seen that antibacterial is applied
Material can significantly kill the bacterium of titanium plate surface infection.
Finally illustrate, preferred embodiment above is merely illustrative of the technical solution of the present invention and unrestricted, although logical
Cross above preferred embodiment the present invention is described in detail, it is to be understood by those skilled in the art that can be
Various changes are made to it in form and in details, without departing from claims of the present invention limited range.
Claims (7)
1. a kind of preparation method for the agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt, it is characterised in that including as follows
Step：
1) high polymer of the unit containing agarobiose is added to the water stirring until being completely dissolved；
2) toward step 1) initiator and quaternary ammonium salt monomer, the initiator, quaternary ammonium salt monomer and agar two are added in solution
The mol ratio of sugar unit is 0.25:10:1~0.25:50:1；
3) by step 2) reaction solution under atmosphere of inert gases 85~95 DEG C stir 3~9 hours；
4) by step 3) in reaction solution pour into beaker and be cooled to room temperature, the gelatinous solid of formation is dialysed with distilled water to be removed
Impurity, obtains the agarose of macromolecular quaternary ammonium salt grafting；
5) by step 4) obtained by macromolecular quaternary ammonium salt grafting agarose pass through dissolve by heating, die casting and cooling and solidifying system
It is standby to obtain antiseptic dressing.
2. the preparation method of the agarose of macromolecular quaternary ammonium salt grafting according to claim 1, it is characterised in that step 2)
The quaternary ammonium salt monomer is polymethyl acyloxyethyl trimethyl ammonium chloride, the phenylethylene containing quaternary ammonium salt, acrylamide
Class, methacryl amine, esters of acrylic acid or the third vinyl monomer.
3. the preparation method of the agarose of macromolecular quaternary ammonium salt grafting according to claim 2, it is characterised in that the season
Ammonium salt class monomer is polymethyl acyloxyethyl trimethyl ammonium chloride.
4. a kind of preparation method of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt according to claim 1,
Characterized in that, step 1) high polymer of the unit containing agarobiose is agarose, the natural extract containing agarose or
One or more in agarose derivative.
5. a kind of preparation method of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt according to claim 1,
Characterized in that, step 2) initiator be potassium peroxydisulfate, azodiisobutyronitrile, ammonium persulfate or azo dicyano valeric acid.
6. a kind of preparation method of agarose antiseptic dressing being grafted based on macromolecular quaternary ammonium salt according to claim 5,
Characterized in that, the initiator is potassium peroxydisulfate.
7. utilize a kind of preparation of any described agarose antiseptic dressings being grafted based on macromolecular quaternary ammonium salt of claim 1-6
The antiseptic dressing that method is prepared, it is characterised in that the structural formula of the agarose of macromolecular quaternary ammonium salt grafting is：
Wherein, the positive integer of m=300~500, the positive integer of n=10~50.
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| CN201710532944.7A CN107261201B (en) | 2017-07-03 | 2017-07-03 | Agarose antibacterial dressing based on macromolecule quaternary ammonium salt grafting and preparation method thereof |
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| CN201710532944.7A CN107261201B (en) | 2017-07-03 | 2017-07-03 | Agarose antibacterial dressing based on macromolecule quaternary ammonium salt grafting and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108130627A (en) * | 2017-12-22 | 2018-06-08 | 合肥洁诺无纺布制品有限公司 | A kind of operating coat antibacterial polylactic acid fiber |
| CN108498853A (en) * | 2018-04-25 | 2018-09-07 | 重庆工程职业技术学院 | A kind of preparation method of polysaccharide quaternary ammonium salt antiseptic dressing |
| CN113616851A (en) * | 2021-09-07 | 2021-11-09 | 山东大学 | Chitosan/poly (2-methacryloyloxyethyl) trimethyl ammonium chloride hydrogel |
| EP4186364A1 (en) * | 2021-11-30 | 2023-05-31 | Livinguard AG | Antimicrobial treatment of substrates |
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| CN101085419A (en) * | 2007-06-21 | 2007-12-12 | 北京服装学院 | Glycosyl quaternary ammonium salt cation surfactant, preparation method and application |
| US9204633B2 (en) * | 2012-08-13 | 2015-12-08 | Aphex Biocleanse Systems, Inc. | Using an unsubstituted quatenary ammonium salt composition with other ingredients as a skin sanitizing solution and natural skin conditioner |
| CN106039382A (en) * | 2016-05-25 | 2016-10-26 | 东华大学 | Glucan-based transparent hydrogel dressing and preparation method thereof |
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2017
- 2017-07-03 CN CN201710532944.7A patent/CN107261201B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101085419A (en) * | 2007-06-21 | 2007-12-12 | 北京服装学院 | Glycosyl quaternary ammonium salt cation surfactant, preparation method and application |
| US9204633B2 (en) * | 2012-08-13 | 2015-12-08 | Aphex Biocleanse Systems, Inc. | Using an unsubstituted quatenary ammonium salt composition with other ingredients as a skin sanitizing solution and natural skin conditioner |
| CN106039382A (en) * | 2016-05-25 | 2016-10-26 | 东华大学 | Glucan-based transparent hydrogel dressing and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108130627A (en) * | 2017-12-22 | 2018-06-08 | 合肥洁诺无纺布制品有限公司 | A kind of operating coat antibacterial polylactic acid fiber |
| CN108498853A (en) * | 2018-04-25 | 2018-09-07 | 重庆工程职业技术学院 | A kind of preparation method of polysaccharide quaternary ammonium salt antiseptic dressing |
| CN113616851A (en) * | 2021-09-07 | 2021-11-09 | 山东大学 | Chitosan/poly (2-methacryloyloxyethyl) trimethyl ammonium chloride hydrogel |
| CN113616851B (en) * | 2021-09-07 | 2022-08-05 | 山东大学 | Chitosan/poly (2-methacryloyloxyethyl) trimethyl ammonium chloride hydrogel |
| EP4186364A1 (en) * | 2021-11-30 | 2023-05-31 | Livinguard AG | Antimicrobial treatment of substrates |
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