CN106727671A - A kind of glycosaminoglycan quaternary ammonium salt solution with antibacterial activity and preparation method thereof - Google Patents
A kind of glycosaminoglycan quaternary ammonium salt solution with antibacterial activity and preparation method thereof Download PDFInfo
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- CN106727671A CN106727671A CN201710009683.0A CN201710009683A CN106727671A CN 106727671 A CN106727671 A CN 106727671A CN 201710009683 A CN201710009683 A CN 201710009683A CN 106727671 A CN106727671 A CN 106727671A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
Abstract
The invention discloses a kind of glycosaminoglycan quaternary ammonium salt solution with antibacterial activity, it is characterized in that with 2,3 epoxypropyltrimethylchloride chlorides, glycosaminoglycan are raw material, in the reaction of high-pressure magnetic reactor, high substituted degree glycosaminoglycan quaternary ammonium salt is generated under specified conditions, antibacterial activity strengthens, and good stability is with short production cycle, low production cost, excellent, raising evident in efficacy is acted on, good result is achieved.
Description
Technical field
The present invention relates to field of medicaments, and in particular to a kind of glycosaminoglycan quaternary ammonium salt solution and its system with antibacterial activity
Preparation Method.
Background technology
Prepared by glycosaminoglycan quaternary ammonium salt is chemically modified glycosaminoglycan glycosaminoglycan higher derivative, with antibacterial
Performance, nontoxic, good biocompatibility is biodegradable, and its antibacterial activity is related to substitution value.Amino prepared by prior art is more
Sugared quaternary ammonium salt substitution value is low, and antibacterial activity is weak, and the production cycle is long, and production cost is high, and stability is poor, it is impossible to satisfactory.
The content of the invention
The present invention is, according to chemical synthesis experience for many years, with reference to modern chemical industry synthetic technology, there is provided a kind of high substituted degree, to resist
Bacterium activity is strong, and good stability is with short production cycle, low production cost, acts on excellent glycosaminoglycan quaternary ammonium salt solution.
Invention embodiment is as follows：
50 parts of 2,3 epoxypropyltrimethylchloride chloride is taken, is put in reactor, add 100 parts of 30% sodium hydroxide solution, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add isopropyl
40 parts of alcohol, 1 part of Magnesiumaluminumsilicate, 1 part of calcium chloride, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, choosing
Magnetic force power 1600W is selected, 75~85 DEG C are warming up to, reacted 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake is added
100 parts of absolute ethyl alcohol, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and product substitution value is 99%, rotation
Concentration, plus purified water is made the glycosaminoglycan quaternary ammonium salt solution that mass concentration is 0.010%~10%.
The raw material standards that the embodiment above is previously mentioned is as follows：
2,3 epoxypropyltrimethylchloride chlorides：No. CAS：3033-77-0；
NaOH：The Chinese Pharmacopoeia ministerial standard of version four in 2015；
Isopropanol：The Chinese Pharmacopoeia ministerial standard of version four in 2015；
Magnesiumaluminumsilicate：The Chinese Pharmacopoeia ministerial standard of version four in 2015；
Calcium chloride：The Chinese Pharmacopoeia ministerial standard of version four in 2015；Hydrochloric acid：The Chinese Pharmacopoeia ministerial standard of version four in 2015；
Absolute ethyl alcohol：The Chinese Pharmacopoeia ministerial standard of version four in 2015；
Glycosaminoglycan：The straight-chain polysaccharide of the disaccharide unit repeated polymerization that amidohexose is constituted with uronic acid, its amidohexose
It is often 2-Acetamido-2-deoxy-D-glucose base N- acetylamino galactosamines, uronic acid is usually glucuronic acid：Inner controlling standard of enterprise.
Raw material used in the present invention can be commercially available from pharmaceuticals, as long as meet standard to can be used to implement this
Scheme of the invention.
The key equipment that foregoing invention embodiment is previously mentioned is as follows：
High-pressure magnetic reactor：1000~2000W of power；
（Typical production producer:The global chemical machinery Co., Ltd in Weihai）
Above equipment Market has sale, however it is not limited to listed typical production producer, as long as technical indicator can reach requirement,
Can be used to realize the present invention.
" part " described in foregoing invention scheme refers to weight portion.
When reaction temperature and pressure are not indicated in foregoing invention scheme, all refer to normal temperature, normal pressure.
Term used is pharmacy proprietary term in foregoing invention scheme, unless otherwise specified, all defers to Chinese Pharmacopoeia and state
Food and medicine Surveillance Authority of family related specifications.
Specific embodiment
Specific embodiment of the invention 1
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
Concentration is 0.01% glycosaminoglycan quaternary ammonium salt solution.
Specific embodiment of the invention 2
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
The glycosaminoglycan quaternary ammonium salt solution of concentration 0.1%, pours into feeder, is made glycosaminoglycan quaternary ammonium salt nasal wash,.
Specific embodiment of the invention 3
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and product substitution value is 99%, spin concentration,
Plus purified water is made the glycosaminoglycan quaternary ammonium salt solution that mass concentration is 0.05%, pours into feeder, is made glycosaminoglycan quaternary ammonium
Salt oral cavity flushing washing lotion.
Specific embodiment of the invention 4
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
Concentration is 0.10% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt vaginal douche.
Specific embodiment of the invention 5
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
The glycosaminoglycan quaternary ammonium salt gel of concentration 10.0%, pours into feeder, is made glycosaminoglycan quaternary ammonium salt woman with filling gel.
Specific embodiment of the invention 6
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
Concentration is 10% glycosaminoglycan quaternary ammonium salt gel, in pouring into feeder, is made glycosaminoglycan quaternary ammonium salt and disappears hemorrhoid gel.
Specific embodiment of the invention 7
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
Concentration is 0.10% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt skin washing solutions.
Specific embodiment of the invention 8
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
Concentration is 0.3% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt flushing liquor.
Specific embodiment of the invention 9
2,3 epoxypropyltrimethylchloride chloride 50g are taken, is put in reactor, add 30% sodium hydroxide solution 100g, stirring 1 is small
When, it is made 2,3 epoxypropyltrimethylchloride chloride solution；Glycosaminoglycan 8g is taken, is put in high-pressure magnetic reactor, add isopropanol
40g, Magnesiumaluminumsilicate 1g, calcium chloride 1g, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic
Activity of force 1600W, is warming up to 75~85 DEG C, reacts 1 hour, adds 10% hydrochloric acid to adjust pH value to 7.0, and suction filtration, filter cake adds anhydrous
Ethanol 100g, reacts 1 hour, is purified with the dialysis membrane that molecular cut off is 300000, and spin concentration, plus purified water is made quality
Concentration is 0.02% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made the clean intestinal juice of glycosaminoglycan quaternary ammonium salt.
Actual effect of the invention is investigated with embodiment below：
（One）Glycosaminoglycan quaternary ammonium salt solution substitution value obtained in embodiment 1 is determined.
1 assay method
According to potentiometric titration（Chinese Pharmacopoeia version in 2015 four 0701）Determine, the sample 100ml of Example 1, in putting conical flask,
Titrated with the AgNO3 titrating solutions of 0.017mol/L, meter record AgNO3 consumption volumes calculate glycosaminoglycan quaternary ammonium salt substitution value.
The glycosaminoglycan quaternary ammonium salt substitution value of table 1
| Name of product | Substitution value |
| Glycosaminoglycan quaternary ammonium salt prepared by embodiment 1 | 0.99 |
Data above shows：The substitution value of glycosaminoglycan quaternary ammonium salt solution prepared by the present invention is 0.99.
（Two）Glycosaminoglycan quaternary ammonium salt bacteriostatic activity obtained in embodiment 1.
The glycosaminoglycan quaternary ammonium salt bacteriostatic activity of table 2 is contrasted
Data above shows：Glycosaminoglycan quaternary ammonium salt prepared by the present invention is more antibacterial than glycosaminoglycan quaternary ammonium salt prepared by prior art
Activity is significantly increased, p ＜ 0.01.
（Three）Glycosaminoglycan quaternary ammonium salt solution stability obtained in embodiment 1.
Glycosaminoglycan quaternary ammonium salt solution term of validity contrast table obtained in the embodiment 1 of table 3
Data above shows：Glycosaminoglycan quaternary ammonium salt prepared by the present invention is more stable than glycosaminoglycan quaternary ammonium salt prepared by prior art
Property is significantly increased, p ＜ 0.01.
（Four）The obtained glycosaminoglycan quaternary ammonium salt production cycle of the invention
The production cycle of table 4 contrasts
Data above shows：The present invention prepares the glycosaminoglycan quaternary ammonium salt production cycle than glycosaminoglycan quaternary ammonium prepared by prior art
The salt production cycle significantly shortens, p ＜ 0.01.
（Five）Obtained glycosaminoglycan quaternary ammonium salt production cost of the invention
The production cost of table 5 is contrasted
Data above shows：The present invention prepares glycosaminoglycan quaternary ammonium salt production cost than glycosaminoglycan quaternary ammonium prepared by prior art
Salt production cost is significantly reduced, p ＜ 0.01.
（Six）Glycosaminoglycan quaternary ammonium salt vaginal bioadhesive long acting antibiotic gel clinical observation on the therapeutic effect obtained in embodiment 5
1 case scenario
Statistics outpatient service and inpatient, observe vaginitis patient 60, average age 32 years old altogether.Patient has different degrees of the moon
The symptoms such as road itch, abnormal leucorrhea, private parts peculiar smell, clinical diagnosis is vaginitis.Patient is randomly divided into two groups, test group is used
Glycosaminoglycan quaternary ammonium salt vaginal bioadhesive long acting antibiotic gel obtained in embodiment 5, control group uses commercially available nano silver antimicrobial gel.
2 efficacy assessment standards
Cure：Symptom, sign disappear or basic disappearance, and integration reduces >=95%.
It is effective：Symptom, sign are obviously improved, and integration reduces >=70%.
Effectively：Symptom, sign take a favorable turn, and integration reduces >=30%.
It is invalid：Symptom, sign are not improved or aggravate, and integration reduces ＜ 30%.
Computing formula：[（Integrated after integration-treatment before treatment）Integration before ÷ treatments] × 100%.
3 clinical observation results
The glycosaminoglycan quaternary ammonium salt vaginal bioadhesive long acting antibiotic gel clinical efficacy contrast table of 6 embodiment of table 5
Data above shows：Glycosaminoglycan quaternary ammonium salt vaginal bioadhesive long acting antibiotic gel prepared by the present invention is evident in efficacy higher than city
Sell nano silver antimicrobial gel, p ＜ 0.01.
（Seven）Glycosaminoglycan quaternary ammonium salt hemorrhoid biology long acting antibiotic gel clinical observation on the therapeutic effect obtained in embodiment 6
1 case scenario
Statistics outpatient service and inpatient, observe hemorrhoid patients 98, average age 42 years old altogether.Patient has different degrees of anus
It is swollen red, to have blood in stool, severe pain symptom, clinical diagnosis is hemorrhoid.Patient is randomly divided into two groups, test group is used obtained in embodiment 6
Glycosaminoglycan quaternary ammonium salt hemorrhoid biology long acting antibiotic gel, control group uses commercially available MAYINGLONGZHICHUANGGAO.
2 efficacy assessment standards
Cure：Symptom, sign disappear or basic disappearance, and integration reduces >=95%.
It is effective：Symptom, sign are obviously improved, and integration reduces >=70%.
Effectively：Symptom, sign take a favorable turn, and integration reduces >=30%.
It is invalid：Symptom, sign are not improved or aggravate, and integration reduces ＜ 30%.
Computing formula：[（Integrated after integration-treatment before treatment）Integration before ÷ treatments] × 100%.
3 clinical observation results
Glycosaminoglycan quaternary ammonium salt hemorrhoid biology long acting antibiotic gel clinical efficacy contrast table prepared by 7 embodiment of table 6
Data above shows：Glycosaminoglycan quaternary ammonium salt hemorrhoid biology long acting antibiotic gel prepared by the present invention is evident in efficacy higher than city
Sell MAYINGLONGZHICHUANGGAO, p ＜ 0.01.
Claims (10)
1. a kind of glycosaminoglycan quaternary ammonium salt solution with antibacterial activity, it is characterized in that taking 2,3 epoxypropyltrimethylchloride chlorides
50 parts, put in reactor, add 100 parts of 30% sodium hydroxide solution, stir 1 hour, be made 2,3 epoxypropyl trimethylammonium chlorides
Ammonium salt solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, 1 part of calcium chloride,
Stirring 1 hour, adds above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, selects magnetic force power 1600W, is warming up to 75~85
DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, reacts 1 hour, with cutting
Dialysis membrane that molecular weight is 300000 is stayed to purify, product substitution value is 99%, spin concentration, plus purified water is made mass concentration and is
0.010%~10% glycosaminoglycan quaternary ammonium salt solution.
2. the preparation method of solution according to claim 1, it is characterized in that 50 parts of 2,3 epoxypropyltrimethylchloride chloride is taken,
Put in reactor, add 100 parts of 30% sodium hydroxide solution, stir 1 hour, be made 2,3 epoxypropyltrimethylchloride chlorides molten
Liquid；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, 1 part of calcium chloride, stirring
1 hour, above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution is added, select magnetic force power 1600W, be warming up to 75~85 DEG C, instead
Answer 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, reacts 1 hour, with retention point
Son amount is purified for 300000 dialysis membrane, and product substitution value is 99%, and spin concentration, plus purified water is made mass concentration and is
0.010%~10% glycosaminoglycan quaternary ammonium salt solution.
3. a kind of glycosaminoglycan quaternary ammonium salt nasal wash with antibacterial activity, it is characterized in that taking 2,3 epoxies
50 parts of ammonium chloride, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 glycidyl front threes
Ammonium chloride solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, chlorination
1 part of calcium, stirs 1 hour, adds above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, selects magnetic force power 1600W, is warming up to
75~85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, and reaction 1 is small
When, to be purified with the dialysis membrane that molecular cut off is 300000, product substitution value is 99%, and spin concentration, plus purified water is made quality
Concentration is 0.010%~10% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt nasal douche
Liquid.
4. a kind of glycosaminoglycan quaternary ammonium salt oral cavity flushing washing lotion with antibacterial activity, it is characterized in that taking 2,3 epoxies
50 parts of ammonium chloride, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 glycidyl front threes
Ammonium chloride solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, chlorination
1 part of calcium, stirs 1 hour, adds above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, selects magnetic force power 1600W, is warming up to
75~85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, and reaction 1 is small
When, to be purified with the dialysis membrane that molecular cut off is 300000, product substitution value is 99%, and spin concentration, plus purified water is made quality
Concentration is 0.010%~10% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt dentilave
Liquid.
5. a kind of glycosaminoglycan quaternary ammonium salt vaginal douche with antibacterial activity, it is characterized in that taking 2,3 epoxies
50 parts of ammonium chloride, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 glycidyl front threes
Ammonium chloride solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, chlorination
1 part of calcium, stirs 1 hour, adds above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, selects magnetic force power 1600W, is warming up to
75~85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, and reaction 1 is small
When, to be purified with the dialysis membrane that molecular cut off is 300000, product substitution value is 99%, and spin concentration, plus purified water is made quality
Concentration is 0.010%~10% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt Vaginal lavages
Liquid.
6. a kind of glycosaminoglycan quaternary ammonium salt woman with antibacterial activity uses filling gel, it is characterized in that taking 2,3 glycidyl front threes
50 parts of ammonium chloride, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 glycidyl three
Methyl chloride ammonium salt solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, chlorine
Change 1 part of calcium, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic force power 1600W, heat up
To 75~85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, reaction 1
Hour, to be purified with the dialysis membrane that molecular cut off is 300000, product substitution value is 99%, and spin concentration, plus purified water is made matter
Amount concentration is 1%~10% glycosaminoglycan quaternary ammonium salt gel, is poured into feeder, is made glycosaminoglycan quaternary ammonium salt woman solidifying with filling
Glue.
7. a kind of glycosaminoglycan quaternary ammonium salt with antibacterial activity disappears hemorrhoid gel, it is characterized in that taking 2,3 epoxy chlorine
Change 50 parts of ammonium, put in reactor, add 100 parts of 30% sodium hydroxide solution, stir 1 hour, be made 2,3 epoxies
Ammonium chloride solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, calcium chloride
1 part, stir 1 hour, add above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, select magnetic force power 1600W, be warming up to 75
~85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, reacts 1 hour,
Purified with the dialysis membrane that molecular cut off is 300000, product substitution value is 99%, spin concentration, plus purified water to be made quality dense
The glycosaminoglycan quaternary ammonium salt gel for 1%~10% is spent, in pouring into feeder, glycosaminoglycan quaternary ammonium salt is made and is disappeared hemorrhoid gel.
8. a kind of glycosaminoglycan quaternary ammonium salt skin washing solutions with antibacterial activity, it is characterized in that taking 2,3 epoxies
50 parts of ammonium chloride, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 glycidyl front threes
Ammonium chloride solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, chlorination
1 part of calcium, stirs 1 hour, adds above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution, selects magnetic force power 1600W, is warming up to
75~85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, and reaction 1 is small
When, to be purified with the dialysis membrane that molecular cut off is 300000, product substitution value is 99%, and spin concentration, plus purified water is made quality
Concentration is 0.010%~10% glycosaminoglycan quaternary ammonium salt solution, is poured into feeder, is made the flushing of glycosaminoglycan quaternary ammonium salt skin
Liquid.
9. a kind of glycosaminoglycan quaternary ammonium salt flushing liquor with antibacterial activity, it is characterized in that taking 2,3 epoxypropyl trimethylammonium chlorides
50 parts of ammonium, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 epoxy chlorine
Change ammonium salt solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, calcium chloride 1
Part, stir 1 hour, above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution is added, magnetic force power 1600W is selected, it is warming up to 75~
85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, reacts 1 hour, uses
Molecular cut off is 300000 dialysis membrane purifying, and product substitution value is 99%, and spin concentration, plus purified water is made mass concentration
It is 0.010%~10% glycosaminoglycan quaternary ammonium salt solution, pours into feeder, is made glycosaminoglycan quaternary ammonium salt flushing liquor.
10. a kind of clean intestinal juice of glycosaminoglycan quaternary ammonium salt with antibacterial activity, it is characterized in that taking 2,3 epoxypropyl trimethylammonium chlorides
50 parts of ammonium, puts in reactor, adds 100 parts of 30% sodium hydroxide solution, stirs 1 hour, is made 2,3 epoxy chlorine
Change ammonium salt solution；8 parts of glycosaminoglycan is taken, is put in high-pressure magnetic reactor, add 40 parts of isopropanol, 1 part of Magnesiumaluminumsilicate, calcium chloride 1
Part, stir 1 hour, above-mentioned 2,3 epoxypropyltrimethylchloride chloride solution is added, magnetic force power 1600W is selected, it is warming up to 75~
85 DEG C, react 1 hour, add 10% hydrochloric acid to adjust pH value to 7.0, suction filtration, filter cake adds 100 parts of absolute ethyl alcohol, reacts 1 hour, uses
Molecular cut off is 300000 dialysis membrane purifying, and product substitution value is 99%, and spin concentration, plus purified water is made mass concentration
It is 0.010%~10% glycosaminoglycan quaternary ammonium salt solution, pours into feeder, is made the clean intestinal juice of glycosaminoglycan quaternary ammonium salt.
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| CN107456509A (en) * | 2017-08-30 | 2017-12-12 | 海南鸿昇生物药械有限公司 | A kind of external application biological agent and preparation method for vagina prevention, health care and treatment gynaecology genital inflammation |
| CN109692583A (en) * | 2017-10-20 | 2019-04-30 | 中国石油化工股份有限公司 | Antibacterial type dry film and its preparation method and application |
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| CN104163876A (en) * | 2014-08-25 | 2014-11-26 | 吉林君同行生物科技有限公司 | Chitosan quaternary ammonium salt product and preparation method thereof |
| CN104887697A (en) * | 2015-05-26 | 2015-09-09 | 吉林君同行生物科技有限公司 | Glycosaminoglycan quaternary ammonium salt composition and application and preparation thereof |
| CN105664239A (en) * | 2016-03-23 | 2016-06-15 | 成都交大麦迪克科技有限公司 | Preparation method of self-adhesive skin repairing hydrogel |
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| CN104887697A (en) * | 2015-05-26 | 2015-09-09 | 吉林君同行生物科技有限公司 | Glycosaminoglycan quaternary ammonium salt composition and application and preparation thereof |
| CN105664239A (en) * | 2016-03-23 | 2016-06-15 | 成都交大麦迪克科技有限公司 | Preparation method of self-adhesive skin repairing hydrogel |
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| CN107456509A (en) * | 2017-08-30 | 2017-12-12 | 海南鸿昇生物药械有限公司 | A kind of external application biological agent and preparation method for vagina prevention, health care and treatment gynaecology genital inflammation |
| CN109692583A (en) * | 2017-10-20 | 2019-04-30 | 中国石油化工股份有限公司 | Antibacterial type dry film and its preparation method and application |
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