LU502676B1 - Chitosan bipyridine quaternary ammonium salt and preparation method thereof - Google Patents
Chitosan bipyridine quaternary ammonium salt and preparation method thereof Download PDFInfo
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- LU502676B1 LU502676B1 LU502676A LU502676A LU502676B1 LU 502676 B1 LU502676 B1 LU 502676B1 LU 502676 A LU502676 A LU 502676A LU 502676 A LU502676 A LU 502676A LU 502676 B1 LU502676 B1 LU 502676B1
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- 229920001661 Chitosan Polymers 0.000 title claims abstract description 72
- -1 bipyridine quaternary ammonium salt Chemical class 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 claims abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000502 dialysis Methods 0.000 claims description 10
- FFHRKYGEMWVANQ-UHFFFAOYSA-N 4-[[4-(pyridin-4-ylmethyl)phenyl]methyl]pyridine Chemical compound C=1C=C(CC=2C=CN=CC=2)C=CC=1CC1=CC=NC=C1 FFHRKYGEMWVANQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims 1
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 13
- 230000001954 sterilising effect Effects 0.000 abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 230000007794 irritation Effects 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 description 17
- 230000002147 killing effect Effects 0.000 description 10
- 241000222122 Candida albicans Species 0.000 description 8
- 241000588724 Escherichia coli Species 0.000 description 8
- 241000191967 Staphylococcus aureus Species 0.000 description 8
- 229940095731 candida albicans Drugs 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000009471 action Effects 0.000 description 4
- OGNCVVRIKNGJHQ-UHFFFAOYSA-N 4-(3-pyridin-4-ylpropyl)pyridine Chemical compound C=1C=NC=CC=1CCCC1=CC=NC=C1 OGNCVVRIKNGJHQ-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000036556 skin irritation Effects 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
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Abstract
Provided is a preparation method of a chitosan bipyridine quaternary ammonium salt, which belongs to the technical field of medicine. The method comprises: reacting chitosan (CS) with bromoacetyl bromide at low temperature to obtain CS-Br first; and then reacting the CS-Br with a long-chain compound containing two pyridine groups to obtain a water-soluble chitosan bipyridine quaternary ammonium salt. The obtained chitosan bipyridine quaternary ammonium salt has good water solubility, high sterilization efficiency, low toxicity and irritation, and has broad spectrum sterilization effect. The obtained chitosan bipyridine quaternary ammonium salt has no irritation to skin.
Description
CHITOSAN BIPYRIDINE QUATERNARY AMMONIUM SALT AND PREPARATION °°
METHOD THEREOF
The present invention belongs to the technical field of medicine, and more particularly, relates to a chitosan bipyridine quaternary ammonium salt and a preparation method thereof.
With the improvement of people's living standard, the safety requirements of common fungicides in daily life are becoming higher. Chitosan has a wide range of sources, is a product of natural polysaccharide chitin in which partial acetyl is removed, has many physiological functions such as biodegradability, biocompatibility, non-toxicity, bacteriostasis, anticancer, lipid-lowering and immune enhancement, and is widely used in many fields such as food additives, textiles, agriculture, environmental protection, beauty care, cosmetics and antibacterial agents. As a new generation of antibacterial material, the chitosan is insoluble in water and organic solvent, and has a poor antibacterial effect. Bisquaternary ammonium salt has a high bactericidal efficiency, a low toxicity and a low irritation, and has a broad-spectrum bactericidal effect.
The modification of the chitosan into a chitosan bipyridine quaternary ammonium salt improves the water solubility of the chitosan and greatly improves the antibacterial property at the same time. A novel chitosan bipyridine quaternary ammonium salt has a stronger antibacterial ability and a better biocompatibility, and can be applied to surgical sutures, medical dressings, etc.
Aiming at the existing technical problems above, the present invention provides a chitosan bipyridine quaternary ammonium salt and a preparation method thereof.
The object of the present invention may be achieved by the following technical solutions.
A preparation method of a chitosan bipyridine quaternary ammonium salt comprises the following steps of: 1) dispersing chitosan in an organic solvent a, adding bromoacetyl bromide at a temperature of 3°C to 10°C for reaction for 20 hours to 24 hours, and centrifuging, washing 02676 and drying the mixture after the reaction to obtain bromine-end-group-contained chitosan
CS-Br; and 2) dissolving a long-chain compound containing two pyridine groups in an organic solvent b, adding the CS-Br for heating and refluxing for 20 hours to 30 hours, centrifuging the reaction solution after reaction, and then adding a supernatant into a dialysis bag for dialysis to obtain the water-soluble chitosan bipyridine quaternary ammonium salt.
In the technical solutions of the present invention, a molar ratio of the bromoacetyl bromide to the chitosan in step 1) is 4 to 8: 1 to 2.
In the technical solutions of the present invention, the organic solvent a is toluene.
In the technical solutions of the present invention, the chitosan is added into the organic solvent a at a temperature of 35°C to 40°C and stirred for 0.5 hour to 1 hour.
In the technical solutions of the present invention, the organic solvent b is an alcohol solvent, and the organic solvent b is preferably ethanol.
In the technical solutions of the present invention, the long chain compound containing two pyridine groups is at least one of 4,4'-trimethylenedipyridine (CAS:17252-51-6), 1,4-bis(4-pyridylmethyl)benzene (CAS:52469-20-2) and 1,2-bis(4-(pyridin-4-yl)phenyl)ethynyl (CAS:1189377-77-2).
In the technical solutions of the present invention, a molar ratio of the long-chain compound containing two pyridine groups to the CS-Bris 0.3 to 1: 1 to 3.
Beneficial effects of the present invention:
The chitosan bipyridine quaternary ammonium salt designed and prepared by the present invention has the following beneficial effects: 1. the chitosan bipyridine quaternary ammonium salt has a capability of killing
Escherichia coli, Staphylococcus aureus and Candida albicans, with sterilization rates greater than or equal to 99%; and 2. toxicological experiments show that the chitosan bipyridine quaternary ammonium salt has no skin irritation and no skin allergy.
The present invention is further described hereinafter with reference to the embodiments,
but the scope of protection of the present invention is not limited to this. 502676
Embodiment 1: The present invention provides a preparation method of a chitosan bipyridine quaternary ammonium salt, which comprises the following steps. 1) 1.61 g of chitosan (CS) powder was dispersed in 50 ml of toluene, the mixture was heated to 40°C, stirred for 1 hour, cooled to 5°C, and added with 4.2 g of bromoacetyl bromide, and then the mixture was stirred for 24 hours, centrifuged, and washed with deionized water for many times to obtain bromine-end-group-contained chitosan (CS-Br). The bromine-end-group-contained chitosan was dried to obtain dried CS-Br. 2) 0.46 g of 4,4'-trimethylenedipyridine was dissolved in 50 ml of ethanol, and the mixture was added with 2.0 g of CS-Br, and heated and refluxed for 24 hours to obtain a crude product of the chitosan bipyridine quaternary ammonium salt. After the reaction solution was centrifuged, a supernatant was added into a dialysis bag for dialysis for one week to remove impurities, so as to obtain the water soluble chitosan bipyridine quaternary ammonium salt.
Embodiment 2: The present invention provides a preparation method of a chitosan bipyridine quaternary ammonium salt, which comprises the following steps. 1) 1.61 g of chitosan (CS) powder was dispersed in 50 ml of toluene, the mixture was heated to 40 °C, stirred for 1 hour, cooled to 5°C, and added with 6.0 g of bromoacetyl bromide, and then the mixture was stirred for 24 hours, centrifuged, and washed with deionized water for many times to obtain bromine-end-group-contained chitosan (CS-Br). The bromine-end-group-contained chitosan was dried to obtain dried CS-Br. 2) 0.61 g of 1,4-bis(4-pyridylmethyl)benzene was dissolved in 50 ml of ethanol, and the mixture was added with 2.0 g of CS-Br, and heated and refluxed for 24 hours to obtain a crude product of the chitosan bipyridine quaternary ammonium salt. After the reaction solution was centrifuged, a supernatant was added into a dialysis bag for dialysis for one week to remove impurities, so as to obtain the water soluble chitosan bipyridine quaternary ammonium salt.
Embodiment 3: The present invention provides a preparation method of a chitosan bipyridine quaternary ammonium salt, which comprises the following steps. 1) 1.61 g of chitosan (CS) powder was dispersed in 50 ml of toluene, the mixture was heated to 40 °C, stirred for 1 hour,
cooled to 5 °C, and added with 8.0 g of bromoacetyl bromide, and then the mixture was stirred 02676 for 24 hours, centrifuged, and washed with deionized water for many times to obtain bromine-end-group-contained chitosan (CS-Br). The bromine-end-group-contained chitosan was dried to obtain dried CS-Br. 2) 0.78 g of 1,2-bis(4-(pyridin-4-yl)phenyl)ethynyl was dissolved in 50 ml of ethanol, and the mixture was added with 2.0 g of CS-Br, and heated and refluxed for 24 hours to obtain a crude product of the chitosan bipyridine quaternary ammonium salt. After the reaction solution was centrifuged, a supernatant was added into a dialysis bag for dialysis for one week to remove impurities, so as to obtain the water soluble chitosan bipyridine quaternary ammonium salt.
Sterilization experiments:
Experiments of killing Staphylococcus aureus, Escherichia coli and Candida albicans were carried out on a raw material chitosan, and sterilization rates were detected in different action periods. Results are as follows.
Table 1 Sterilization experiment results of chitosan
Staphylococcus 71.26 73.68 78.60 79.21 aureus
Experiments of killing Staphylococcus aureus, Escherichia coli and Candida albicans were carried out on the chitosan bipyridine quaternary ammonium salt obtained in
Embodiment 1, and sterilization rates in different action periods were detected. Results are as follows.
Table 2 Sterilization experiment results of Embodiment 1
0502676 me [T=
Conclusion: it can be seen from Table 1 that the chitosan has a certain killing effect on the bacteria, but the killing effect is not strong. It can be seen from Table 2 that the chitosan bipyridine quaternary ammonium salt obtained in Embodiment 1 has significant killing effects on all the Staphylococcus aureus, Escherichia coli and Candida albicans. 5 Experiments of killing Staphylococcus aureus, Escherichia coli and Candida albicans were carried out on the chitosan bipyridine quaternary ammonium salt obtained in
Embodiment 2, and sterilization rates in different action periods were detected. Results are as follows.
Table 3 Sterilization experiment results of Embodiment 2
Staphylococcus 98.23 99.25 100 100 aureus
Conclusion: it can be seen from Table 3 that the chitosan bipyridine quaternary ammonium salt obtained in Embodiment 2 has significant killing effects on all the Staphylococcus aureus,
Escherichia coli and Candida albicans.
Experiments of killing Staphylococcus aureus, Escherichia coli and Candida albicans were carried out on the chitosan bipyridine quaternary ammonium salt obtained in
Embodiment 3, and sterilization rates in different action periods were detected. Results are as follows.
Table 4 Sterilization experiment results of Embodiment 3
0502676 me [T=
Conclusion: it can be seen from Table 4 that the chitosan bipyridine quaternary ammonium salt obtained in Embodiment 3 has significant killing effects on all the Staphylococcus aureus,
Escherichia coli and Candida albicans.
Toxicity experiments:
Two toxicological experiments were carried out on the chitosan bipyridine quaternary ammonium salts obtained in Embodiments 1 to 3. The experiments referred to a skin irritation experiment and a skin allergy experiment in the second part of "Technical Standard For disinfection (2002)". Results are shown in the following table.
Table 5 Skin irritation experiment results
Chitosan 1 2 3
Me | 0 | "| #05 1.5 1.5 1.5 experiments
Conclusion: it can be seen from Table 5 that an irritation intensity of the chitosan bipyridine quaternary ammonium salt prepared by the present invention is mild.
Table 6 Skin allergy experiment pas
Chitosan 1 2 3 ae an | 6 | 0 | 0 | 0
Conclusion: it can be seen from Table 6 that a sensitization rate of the chitosan bipyridine quaternary ammonium salt prepared by the present invention is 0. There is no sensitization.
Claims (7)
1. A preparation method of a chitosan bipyridine quaternary ammonium salt, comprising the following steps of: 1) dispersing chitosan in an organic solvent a, stirring the mixture at 35°C to 45°C for 0.5 hour to 1.5 hours, then adding bromoacetyl bromide at a temperature of 3°C to 10°C for reaction for 20 hours to 24 hours, and centrifuging, washing and drying the mixture after the reaction to obtain bromine-end-group-contained chitosan CS-Br; and 2) dissolving a long-chain compound containing two pyridine groups in an organic solvent b, adding the CS-Br for heating and refluxing for 20 hours to 30 hours, centrifuging the reaction solution after reaction, and then adding a supernatant into a dialysis bag for dialysis to obtain the water-soluble chitosan bipyridine quaternary ammonium salt.
2. The preparation method of the chitosan bipyridine quaternary ammonium salt according to claim 1, wherein a molar ratio of the bromoacetyl bromide to the chitosan in step 1) is 4 to 8: 1 to 2.
3. The preparation method of the chitosan bipyridine quaternary ammonium salt according to claim 1, wherein the organic solvent a is toluene.
4. The preparation method of the chitosan bipyridine quaternary ammonium salt according to claim 1, wherein the chitosan is added into the organic solvent a at a temperature of 35°C to 40°C and stirred for 0.5 hour to 1 hour.
5. The preparation method of the chitosan bipyridine quaternary ammonium salt according to claim 1, wherein the organic solvent b is an alcohol solvent, and the organic solvent b is preferably ethanol.
6. The preparation method of the chitosan bipyridine quaternary ammonium salt according to claim 1, wherein the long chain compound containing two pyridine groups is at least one of 44"-trimethylenedipyridine, 1,4-bis(4-pyridylmethyl)benzene (CAS: 52469-20-2) and 1,2-bis(4-(pyridin-4-yl)phenyl)ethynyl.
7. The preparation method of the chitosan bipyridine quaternary ammonium salt according to claim 1, wherein a molar ratio of the long-chain compound containing two pyridine groups to the CS-Br is 0.3 to 1: 1 to 3.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210675862.9A CN117285662A (en) | 2022-06-15 | 2022-06-15 | Chitosan bipyridine quaternary ammonium salt and preparation method thereof |
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| Publication Number | Publication Date |
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| LU502676B1 true LU502676B1 (en) | 2023-12-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| LU502676A LU502676B1 (en) | 2022-06-15 | 2022-08-17 | Chitosan bipyridine quaternary ammonium salt and preparation method thereof |
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| CN (1) | CN117285662A (en) |
| LU (1) | LU502676B1 (en) |
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- 2022-06-15 CN CN202210675862.9A patent/CN117285662A/en active Pending
- 2022-08-17 LU LU502676A patent/LU502676B1/en active IP Right Grant
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