CN116440320B - Guanidine polymer antibacterial gel dressing and preparation method thereof - Google Patents
Guanidine polymer antibacterial gel dressing and preparation method thereof Download PDFInfo
- Publication number
- CN116440320B CN116440320B CN202310701826.XA CN202310701826A CN116440320B CN 116440320 B CN116440320 B CN 116440320B CN 202310701826 A CN202310701826 A CN 202310701826A CN 116440320 B CN116440320 B CN 116440320B
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- China
- Prior art keywords
- polymer
- guanidine
- gel dressing
- antibacterial
- antibacterial gel
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 229920000642 polymer Polymers 0.000 title claims abstract description 79
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 66
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title claims abstract description 43
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 24
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 24
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims abstract description 15
- 229910021642 ultra pure water Inorganic materials 0.000 claims abstract description 14
- 239000012498 ultrapure water Substances 0.000 claims abstract description 14
- 229920000768 polyamine Polymers 0.000 claims abstract description 11
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 9
- 239000003906 humectant Substances 0.000 claims abstract description 9
- 150000003384 small molecules Chemical class 0.000 claims abstract description 8
- 229960004198 guanidine Drugs 0.000 claims description 40
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 150000002357 guanidines Chemical class 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 230000000845 anti-microbial effect Effects 0.000 claims description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- -1 oxalyl diamine Chemical class 0.000 claims description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 8
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 229920002873 Polyethylenimine Polymers 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- 235000010643 Leucaena leucocephala Nutrition 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 4
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 229940063673 spermidine Drugs 0.000 claims description 4
- OJUDFURAIYFYBP-UHFFFAOYSA-N (dihydrazinylmethylideneamino)azanium;chloride Chemical compound Cl.NNC(NN)=NN OJUDFURAIYFYBP-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- AKGZDINYLOSBTE-UHFFFAOYSA-N [(e)-n'-(diaminomethylideneamino)carbamimidoyl]azanium;chloride Chemical compound Cl.NC(=N)NN=C(N)N AKGZDINYLOSBTE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- SCIZLHIMZCLSND-UHFFFAOYSA-N diamino(carbamimidoyl)azanium;chloride Chemical compound Cl.NN(N)C(N)=N SCIZLHIMZCLSND-UHFFFAOYSA-N 0.000 claims description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 claims description 3
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 239000004166 Lanolin Substances 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 2
- XXWCODXIQWIHQN-UHFFFAOYSA-N butane-1,4-diamine;hydron;dichloride Chemical compound Cl.Cl.NCCCCN XXWCODXIQWIHQN-UHFFFAOYSA-N 0.000 claims description 2
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 claims description 2
- RLNAIWYXIAJDTN-UHFFFAOYSA-N hydron;pentane-1,5-diamine;chloride Chemical compound Cl.NCCCCCN RLNAIWYXIAJDTN-UHFFFAOYSA-N 0.000 claims description 2
- 229940001447 lactate Drugs 0.000 claims description 2
- 229940039717 lanolin Drugs 0.000 claims description 2
- 235000019388 lanolin Nutrition 0.000 claims description 2
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 2
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 claims description 2
- 229950008882 polysorbate Drugs 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 229940083575 sodium dodecyl sulfate Drugs 0.000 claims description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 2
- 239000008347 soybean phospholipid Substances 0.000 claims description 2
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 claims 1
- 240000007472 Leucaena leucocephala Species 0.000 claims 1
- 206010059866 Drug resistance Diseases 0.000 abstract description 7
- 230000007774 longterm Effects 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 4
- 230000001988 toxicity Effects 0.000 abstract description 4
- 231100000419 toxicity Toxicity 0.000 abstract description 4
- 206010064687 Device related infection Diseases 0.000 abstract description 2
- 206010031252 Osteomyelitis Diseases 0.000 abstract description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 2
- 208000015181 infectious disease Diseases 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 239000000499 gel Substances 0.000 description 45
- 238000012360 testing method Methods 0.000 description 15
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000017 hydrogel Substances 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 241000220479 Acacia Species 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000002082 metal nanoparticle Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 229920002118 antimicrobial polymer Polymers 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- KPTSBKIDIWXFLF-UHFFFAOYSA-N 1,1,2-triaminoguanidine Chemical class NN=C(N)N(N)N KPTSBKIDIWXFLF-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- A61L26/0014—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- A61L26/0019—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- A61L2300/206—Biguanides, e.g. chlorohexidine
-
- 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
-
- 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
- A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention discloses a guanidine polymer antibacterial gel dressing and a preparation method thereof, wherein the guanidine polymer antibacterial gel dressing comprises the following components in percentage by mass: 5-30% of polyvinyl alcohol, 0.5-5% of guanidino polymer, 5-20% of emulsifier, 5-20% of humectant and the balance of ultrapure water; wherein the guanidino polymer is prepared by reacting a guanidinium salt, a polyamine small molecule, and an amine terminated polymer. The invention solves the problems of low drug resistance, accumulated toxicity and antibacterial durability caused by long-term use of the antibacterial gel dressing in the prior art, has the characteristics of broad spectrum, high efficiency, low toxicity and no drug resistance, and can be effectively applied to the clinical application fields of wound dressing, catheter infection, gastrointestinal tract infection, osteomyelitis, contact lenses and the like.
Description
Technical Field
The invention relates to the technical field of biomedical materials, in particular to guanidine polymer antibacterial gel dressing and a preparation method thereof.
Background
Hydrogels with antibacterial function are a hotspot in biomedical research. The antibacterial gel type medical dressing is characterized in that natural or synthetic polymers are singly or together compounded to prepare a colloidal substance capable of swelling in water remarkably, and the antibacterial gel type medical dressing has the characteristics of high water absorption rate, good biocompatibility, ventilation, bacteriostasis, capability of loading antibacterial substances and the like. At present, a number of antibacterial hydrogels having advanced functional properties, such as high swelling properties, high oxygen permeability, biocompatibility, ease of loading and releasing drugs, etc., have been developed.
Generally, antimicrobial hydrogels can be classified into three types according to antimicrobial materials: hydrogels containing inorganic nanoparticles, hydrogels containing antibiotics, and hydrogels containing functional antimicrobial polymers. The inorganic antibacterial material mainly comprises metal ions and metal oxide nanoparticles, such as silver nanoparticles and zinc oxide nanoparticles. However, the nanoparticles may damage the bacterial cell membrane. Broad-spectrum antibiotics are currently commonly used effective antibacterial agents, such as ciprofloxacin, gentamicin, vancomycin, and the like. However, the drug resistance response exhibited by bacteria has been the biggest obstacle to antibiotic development and application. The functional antibacterial polymer is an effective antibacterial agent developed in recent years, and has small side effects and strong stability compared with inorganic nanoparticles and antibiotics. However, gel dressings developed with such antimicrobial polymers may cause some loss of antimicrobial properties of the polymer.
Most of the prior antibacterial gel dressing adopts antibacterial materials mainly comprising metal nano particles or antibiotics, and is added into the antibacterial gel dressing in a physical blending mode. The metal nano particles or antibiotics are directly contacted with body fluid in the wound environment, so that the accumulation of proteins is easily caused, and the inflammatory reaction of the contact part is aggravated. Meanwhile, the long-term use of the antibacterial gel dressing can also cause the problems of drug resistance, accumulated toxicity of silver ions penetrating into a human body, low antibacterial durability and the like.
Disclosure of Invention
The invention aims to provide a guanidine polymer antibacterial gel dressing and a preparation method thereof, solves the problems of low drug resistance, accumulated toxicity and antibacterial durability caused by long-term use of the antibacterial gel dressing in the prior art, has the characteristics of broad spectrum, high efficiency, low toxicity and no drug resistance, and can be effectively applied to the clinical application fields of wound dressing, catheter infection, gastrointestinal tract infection, osteomyelitis, contact lenses and the like.
In order to achieve the purpose, the invention provides a guanidine polymer antibacterial gel dressing, which comprises the following components in percentage by mass: 5-30% of polyvinyl alcohol, 0.5-5% of guanidino polymer, 5-20% of emulsifier, 5-20% of humectant and the balance of ultrapure water; wherein the guanidino polymer is prepared by reacting a guanidinium salt, a polyamine small molecule, and an amine terminated polymer.
Preferably, the polyvinyl alcohol accounts for 10-20% by mass, the guanidino polymer accounts for 1-3% by mass, the emulsifier accounts for 10-15% by mass, the humectant accounts for 10-15% by mass, and the balance is ultrapure water.
Preferably, the guanidine salt includes inorganic guanidine salts and organic guanidine salts, in particular one or more of guanidine hydrochloride, guanidine nitrate, aminoguanidine hydrochloride, triaminoguanidine hydrochloride, biguanidine hydrochloride, diaminoguanidine hydrochloride or 1, 1-dimethylbiguanide.
Still more preferably, the guanidino compound molecule is one or more of diaminoguanidine hydrochloride, triaminoguanidine hydrochloride, and 1, 1-dimethylbiguanide.
Preferably, the polyamine small molecule comprises one or more of diethylenetriamine, N ', N ' ' -trimethyldiethylenetriamine, tripentylamine, trihexylamine, triethylamine, 1, 6-hexamethylenediamine, adipoylamine, 1, 2-propylenediamine, trimethylhexamethylenediamine, hexamethylenediamine, oxalylenediamine, 1, 4-butanediamine dihydrochloride, spermidine, triethylenetetramine, 1, 5-pentanediamine hydrochloride, tetraethylenepentamine, or 1, 8-octanediamine.
Still more preferably, the polyamine small molecule is one or more of 1, 6-hexamethylenediamine, trimethylhexamethylenediamine, spermidine or tetraethylenepentamine.
Preferably, the amine-terminated polymer comprises one or more of poly (ethylene glycol) diamine, polyethyleneimine, polyvinylamine, polyoxyethylene diamine, or polyetheramine.
Still more preferably, the amine-terminated polymer is one or more of poly (ethylene glycol) diamine, polyethylenimine, or polyetheramine.
Preferably, the mass ratio of the guanidine salt to the polyamine small molecule is 1:2-5:1, and the mass ratio of the guanidine salt to the amine-terminated polymer is 2:1-10:1.
Still preferably, the mass ratio of guanidine salt, polyamine small molecule amine terminated and amine terminated polymer is 2:3:1.
Preferably, the emulsifier is selected from one or more of phosphate, lactate, betaine, polysorbate, sodium dodecyl sulfate, lanolin, acacia, soybean phospholipid, span 80, span 85, and triethanolamine.
Still more preferably, the emulsifier is one or more of betaine, sodium dodecyl sulfate, and acacia.
Preferably, the humectant is selected from one or more of 1, 3-propanediol, glycerol, 1, 3-butanediol, sorbitol, polyethylene glycol.
Still preferably, the humectant is one or more of glycerol and polyethylene glycol.
The preparation method of the guanidine polymer antibacterial gel dressing comprises the following steps:
(1) Adding guanidine salt, polyamine micromolecules and amine-terminated polymer into a reaction vessel, stirring and refluxing for reacting for a certain time under the protection of nitrogen to obtain a polymer containing guanidine groups;
(2) Mixing 5-30% of polyvinyl alcohol, 0.5-5% of guanidino polymer, 5-20% of emulsifier and 5-20% of humectant according to mass percent, and stirring to obtain the guanidine polymer antibacterial gel dressing.
Preferably, in the step (1), the reaction temperature is 70-200 ℃ and the reaction time is 1-20 h.
Still preferably, the reaction temperature is 80-120 ℃ and the reaction time is 5-15 hours.
Preferably, in the step (2), the alcoholysis degree of the polyvinyl alcohol is 78.0 to 99.0mol% and the average molar mass is 7000 to 200000.
Still preferably, the alcoholysis degree of the polyvinyl alcohol is 87.0 to 89.0 mol% and the average molar mass is 13000 to 50000.
The invention has the beneficial effects that:
1) The guanidine group has high activity, so that the guanidine group polymer forms positive electricity, cations in molecules are easy to be electrostatically adsorbed on anion parts on the surfaces of microbial cells of various bacteria and viruses which are usually electronegative, the action of cell lysozyme is hindered, and the surface layer structure of the cells is denatured and destroyed, thereby inhibiting bacterial reproduction and solving the problem of drug resistance caused by long-term use in the prior art.
2) The antibacterial active group of the guanidine polymer antibacterial gel dressing prepared by the invention is a guanidine group fixed in the polymer, has high-efficiency, stable and durable antibacterial activity, and does not contain metal nano particles, so that the problem that metal ions permeate into human body to accumulate toxicity after long-term use is avoided.
3) The guanidine polymer antibacterial gel dressing prepared by the invention has good film forming property, and a layer of film can be spontaneously formed after the guanidine polymer antibacterial gel dressing is coated on the surface of skin or a catheter, so that the guanidine polymer antibacterial gel dressing has good film forming property, can be directly contacted with external air or environment, can also have good moisturizing effect, and can prevent the skin from drying and cracking.
4) The guanidine polymer antibacterial gel dressing prepared by the invention forms a network structure with excellent dispersibility in the emulsification mixing process, has good toughness, is easy to completely remove from the skin or the surface of a catheter, and is convenient to use.
The technical scheme of the invention is further described in detail through the drawings and the embodiments.
Drawings
FIG. 1 is a chart of antimicrobial testing of an antimicrobial gel dressing of the present invention;
FIG. 2 is a schematic illustration of the film forming effect of the antimicrobial gel dressing of the present invention.
Detailed Description
The invention will be further described with reference to examples. Unless defined otherwise, technical or scientific terms used herein should be given the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs. The above-mentioned features of the invention or the features mentioned in the specific examples can be combined in any desired manner, and these specific examples are only intended to illustrate the invention and are not intended to limit the scope of the invention.
Example 1
Mixing guanidine hydrochloride, trimethylhexamethylenediamine and polyethyleneimine according to the mass percentage of 5:4:2, adding the mixture into a reactor, uniformly mixing, heating to 120 ℃ under the protection of nitrogen, stirring and carrying out reflux reaction for 15 hours, and thus obtaining the guanidino polymer.
Adding polyvinyl alcohol with the average molar mass of 13000 into ultra-pure water with the temperature of 95 ℃, stirring until the polyvinyl alcohol is dissolved, cooling to the room temperature, and adding a guanidine polymer, phosphate and glycerol to obtain the guanidine polymer antibacterial gel dressing; wherein, the mass percentage of the polyvinyl alcohol is 15%, the mass percentage of the guanidyl polymer is 1%, the mass percentage of the phosphate is 10%, the mass percentage of the glycerol is 10%, and the balance is ultrapure water.
The prepared guanidine polymer antibacterial gel dressing is subjected to antibacterial property test
Take 1 mL about 10 6 Mixing the CFU/mL E.coli suspension with 1 g guanidine polymer antibacterial gel dressing, culturing at 37deg.C for 12 h, and diluting the cultured solution by 10 5 1 mL was inoculated onto the surface of a test piece with the total number of colonies of the solid nutrient medium, cultured at 37℃for 12 h, and the number of colonies of the test piece was observed.
Through tests, fig. 1 is an antibacterial property test chart of the antibacterial gel dressing in the invention, and b in fig. 1 is an antibacterial effect chart of example 1, wherein the guanidine polymer antibacterial gel dressing can effectively inhibit the growth of escherichia coli as shown in the figure; fig. 2 is a schematic view of the film forming effect of the antibacterial gel dressing of the present invention, and fig. 2 b is a film forming effect of example 1, as shown in the figure, the film forming property of the guanidine polymer antibacterial gel dressing is good, and the film is easy to be completely removed.
Example 2
And mixing the triaminoguanidine salt, the spermidine and the poly (ethylene glycol) diamine according to the mass percentage of 5:2:1, adding the mixture into a reactor, uniformly mixing, heating to 160 ℃ under the protection of nitrogen, and stirring and refluxing for reaction for 10 hours to obtain the guanidino polymer.
Adding polyvinyl alcohol with average molar mass of 50000 into ultra-pure water with the temperature of 95 ℃, stirring until the polyvinyl alcohol is dissolved, cooling to room temperature, and adding guanidine polymer, triethanolamine and sorbitol to obtain guanidine polymer antibacterial gel dressing; wherein, the mass percentage of the polyvinyl alcohol is 20%, the mass percentage of the guanidyl polymer is 2%, the mass percentage of the triethanolamine is 15%, the mass percentage of the sorbitol is 15%, and the rest is ultrapure water.
The prepared guanidine polymer antibacterial gel dressing was subjected to antibacterial property test, and the test method was the same as in example 1. Through tests, the guanidine polymer antibacterial gel dressing can effectively inhibit the growth of escherichia coli, and has good film forming property.
Example 3
The preparation method comprises the steps of mixing biguanidine hydrochloride, oxalyl diamine and polyether amine according to the mass percentage of 5:3:2, adding the mixture into a reactor, uniformly mixing, heating to 180 ℃ under the protection of nitrogen, and stirring and refluxing for 3 hours to obtain the guanidino polymer.
Adding polyvinyl alcohol with the average molar mass of 7000 into ultrapure water with the temperature of 95 ℃, stirring until the polyvinyl alcohol is dissolved, cooling to room temperature, and adding the guanidine polymer, the acacia and the 1, 3-butanediol to obtain the guanidine polymer antibacterial gel dressing; wherein the mass percentage of the polyvinyl alcohol is 25%, the mass percentage of the guanidyl polymer is 4%, the mass percentage of the Arabic gum is 10%, the mass percentage of the 1, 3-butanediol is 10%, and the balance is ultrapure water.
The prepared guanidine polymer antibacterial gel dressing was subjected to antibacterial property test, and the test method was the same as in example 1. Through tests, the guanidine polymer antibacterial gel dressing can effectively inhibit the growth of escherichia coli, and has good film forming property.
Example 4
Mixing 1, 1-dimethyl biguanide, hexamethylenediamine and polyethyleneimine according to the mass percentage of 5:3:1, adding the mixture into a reactor, uniformly mixing, heating to 200 ℃ under the protection of nitrogen, stirring and carrying out reflux reaction for 5 hours, and thus obtaining the guanidino polymer.
Adding polyvinyl alcohol with average molar mass of 200000 into ultra-pure water with the temperature of 95 ℃, stirring until the polyvinyl alcohol is dissolved, cooling to room temperature, and adding guanidine polymer, betaine and glycerol to obtain guanidine polymer antibacterial gel dressing; wherein, the mass percentage of the polyvinyl alcohol is 10%, the mass percentage of the guanidyl polymer is 2%, the mass percentage of the betaine is 8%, the mass percentage of the glycerol is 8%, and the balance is ultrapure water.
The prepared guanidine polymer antibacterial gel dressing was subjected to antibacterial property test, and the test method was the same as in example 1. Through tests, the guanidine polymer antibacterial gel dressing can effectively inhibit the growth of escherichia coli, and has good film forming property.
Comparative example 1
Comparative example 1 differs from example 1 in that the gel dressing without the guanidino polymer was prepared as follows:
adding polyvinyl alcohol with the average molar mass of 13000 into ultra-pure water with the temperature of 95 ℃, stirring until the polyvinyl alcohol is dissolved, cooling to the room temperature, and adding phosphate and glycerol to obtain guanidine polymer antibacterial gel dressing; wherein, the mass percentage of the polyvinyl alcohol is 15%, the mass percentage of the phosphate is 10%, the mass percentage of the glycerol is 10%, and the balance is ultrapure water.
An antimicrobial test was performed, the test method differing from example 1 in that the guanidine polymer antimicrobial gel dressing was replaced with the gel dressing of comparative example 1 containing no guanidine polymer. Through tests, fig. 1 is an antibacterial property test chart of an antibacterial gel dressing in the invention, a in fig. 1 is an antibacterial effect chart of comparative example 1, and as shown in the figure, the gel dressing without adding the guanidine polymer in comparative example 1 has no antibacterial property; fig. 2 is a schematic view showing the film forming effect of the antibacterial gel dressing of the present invention, and a in fig. 2 is a film forming effect of comparative example 1, as shown in the figure, the film forming property of the antibacterial gel dressing of comparative example 1 is similar to that of the antibacterial gel dressing prepared in example 1.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention and not for limiting it, and although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that: the technical scheme of the invention can be modified or replaced by the same, and the modified technical scheme cannot deviate from the spirit and scope of the technical scheme of the invention.
Claims (7)
1. The guanidine polymer antibacterial gel dressing is characterized by comprising the following components in percentage by mass: 5-30% of polyvinyl alcohol, 0.5-5% of guanidino polymer, 5-20% of emulsifier, 5-20% of humectant and the balance of ultrapure water; wherein the guanidino polymer is prepared by the reaction of guanidinium salt, polyamine small molecules and amine-terminated polymer;
the guanidine salt comprises inorganic guanidine salt and organic guanidine salt, and is specifically one or more of guanidine hydrochloride, guanidine nitrate, aminoguanidine hydrochloride, triaminoguanidine hydrochloride, biguanidine hydrochloride, diaminoguanidine hydrochloride or 1, 1-dimethyl biguanide;
the polyamine small molecule comprises one or more of diethylenetriamine, N ', N ' ' -trimethyldiethylenetriamine, tripentylamine, trihexylamine, triethylamine, 1, 6-hexamethylenediamine, adipamide, 1, 2-propylenediamine, trimethylhexamethylenediamine, hexamethylenediamine, oxalyl diamine, 1, 4-butanediamine dihydrochloride, spermidine, triethylenetetramine, 1, 5-pentanediamine hydrochloride, tetraethylenepentamine or 1, 8-octanediamine;
the amine-terminated polymer comprises one or more of poly (ethylene glycol) diamine, polyethylenimine, polyvinylamine, polyoxyethylene diamine, or polyetheramine.
2. The guanidine polymer antimicrobial gel dressing of claim 1, wherein: the mass ratio of the guanidine salt to the polyamine small molecule is 1:2-5:1, and the mass ratio of the guanidine salt to the amine-terminated polymer is 2:1-10:1.
3. The guanidine polymer antimicrobial gel dressing of claim 1, wherein: the emulsifier is one or more selected from phosphate, lactate, betaine, polysorbate, sodium dodecyl sulfate, lanolin, acacia, soybean phospholipid, span 80, span 85, and triethanolamine.
4. The guanidine polymer antimicrobial gel dressing of claim 1, wherein: the humectant is one or more selected from 1, 3-propylene glycol, glycerol, 1, 3-butanediol, sorbitol, and polyethylene glycol.
5. A method of preparing a guanidine polymer antimicrobial gel dressing according to any one of claims 1 to 4, comprising the steps of:
(1) Adding guanidine salt, polyamine micromolecules and amine-terminated polymer into a reaction vessel, stirring and refluxing for reacting for a certain time under the protection of nitrogen to obtain a polymer containing guanidine groups;
(2) Mixing polyvinyl alcohol, a guanidino polymer, an emulsifier and a humectant according to the proportion, and stirring to obtain the guanidino polymer-containing antibacterial gel dressing.
6. The method for preparing the guanidine polymer antibacterial gel dressing according to claim 5, wherein the method comprises the following steps: in the step (1), the reaction temperature is 70-200 ℃ and the reaction time is 1-20 h.
7. The method for preparing the guanidine polymer antibacterial gel dressing according to claim 5, wherein the method comprises the following steps: in the step (2), the alcoholysis degree of the polyvinyl alcohol is 78.0 to 99.0mol% and the average molar mass is 7000 to 200000.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107254045A (en) * | 2017-05-26 | 2017-10-17 | 天津大学 | A kind of preparation method of guanidine like polymer bactericide |
| CN112691231A (en) * | 2020-10-29 | 2021-04-23 | 广东泰宝医疗科技股份有限公司 | Polyvinyl alcohol/sodium alginate/quaternized polyhexamethylene guanidine antibacterial gel and preparation method thereof |
| CN113694012A (en) * | 2021-07-09 | 2021-11-26 | 山西健康之路医疗器械有限公司 | Bacteriostatic film-forming gel |
| CN114425098A (en) * | 2022-02-08 | 2022-05-03 | 褚二喜 | Antibacterial and anti-inflammatory medical gel and preparation method thereof |
| CN114698641A (en) * | 2022-03-25 | 2022-07-05 | 石家庄学院 | Use of guanidine polymers grafted with polyethyleneimine |
-
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107254045A (en) * | 2017-05-26 | 2017-10-17 | 天津大学 | A kind of preparation method of guanidine like polymer bactericide |
| CN112691231A (en) * | 2020-10-29 | 2021-04-23 | 广东泰宝医疗科技股份有限公司 | Polyvinyl alcohol/sodium alginate/quaternized polyhexamethylene guanidine antibacterial gel and preparation method thereof |
| CN113694012A (en) * | 2021-07-09 | 2021-11-26 | 山西健康之路医疗器械有限公司 | Bacteriostatic film-forming gel |
| CN114425098A (en) * | 2022-02-08 | 2022-05-03 | 褚二喜 | Antibacterial and anti-inflammatory medical gel and preparation method thereof |
| CN114698641A (en) * | 2022-03-25 | 2022-07-05 | 石家庄学院 | Use of guanidine polymers grafted with polyethyleneimine |
Non-Patent Citations (1)
| Title |
|---|
| 徐晖主编.《药用高分子材料学》.2019,146-148. * |
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