CN107137749A - Antibacterial wound dressing and preparation method and application thereof - Google Patents
Antibacterial wound dressing and preparation method and application thereof Download PDFInfo
- Publication number
- CN107137749A CN107137749A CN201710368906.2A CN201710368906A CN107137749A CN 107137749 A CN107137749 A CN 107137749A CN 201710368906 A CN201710368906 A CN 201710368906A CN 107137749 A CN107137749 A CN 107137749A
- Authority
- CN
- China
- Prior art keywords
- wound dressing
- carboxymethyl cellulose
- antibacterial wound
- antibacterial
- guanidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 80
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims abstract description 57
- 239000001768 carboxy methyl cellulose Substances 0.000 claims abstract description 57
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims abstract description 56
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims abstract description 56
- -1 guanidine compound Chemical class 0.000 claims abstract description 48
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 41
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 36
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006467 substitution reaction Methods 0.000 claims abstract description 19
- 206010052428 Wound Diseases 0.000 claims description 74
- 208000027418 Wounds and injury Diseases 0.000 claims description 74
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000003960 organic solvent Substances 0.000 claims description 20
- 239000012190 activator Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000000725 suspension Substances 0.000 claims description 17
- 229920002413 Polyhexanide Polymers 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 238000011938 amidation process Methods 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 150000003384 small molecules Chemical class 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 230000002421 anti-septic effect Effects 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000000174 gluconic acid Substances 0.000 claims description 4
- 235000012208 gluconic acid Nutrition 0.000 claims description 4
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 230000000474 nursing effect Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005956 quaternization reaction Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 18
- 238000010521 absorption reaction Methods 0.000 abstract description 11
- 230000005847 immunogenicity Effects 0.000 abstract description 5
- 206010070834 Sensitisation Diseases 0.000 abstract description 4
- 230000008313 sensitization Effects 0.000 abstract description 4
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 230000000638 stimulation Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 26
- 229920000433 Lyocell Polymers 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 22
- 235000011121 sodium hydroxide Nutrition 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005213 imbibition Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229960002713 calcium chloride Drugs 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical class C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000165940 Houjia Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical group ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000648 calcium alginate Substances 0.000 description 1
- 235000010410 calcium alginate Nutrition 0.000 description 1
- 229960002681 calcium alginate Drugs 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001152 differential interference contrast microscopy Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical group 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000029663 wound healing Effects 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
- C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses an antibacterial wound dressing and a preparation method and application thereof, wherein the antibacterial wound dressing is obtained by carrying out amidation reaction on carboxymethyl cellulose and a guanidine compound, the substitution degree of the carboxymethyl cellulose is 0.1-0.6, and the grafting amount of the guanidine compound is 0.2-10.0%. The antibacterial wound dressing has an excellent antibacterial effect, and the antibacterial rate is not less than 99% in seven days; the liquid absorption amount is large, the liquid locking capacity is strong after liquid absorption, and the moisture retention capacity is good; good biocompatibility, no sensitization, no stimulation and no immunogenicity.
Description
Technical field
The present invention relates to wound care or wound healing medical domain, more particularly it relates to which a kind of antibacterial is hindered
Mouth dressing and preparation method and application.
Background technology
Native cellulose is that the most most polysaccharide of wide, content, very abundant of originating are distributed in nature.Current fibre element
Modification technology is concentrated mainly on etherificate and the aspect of esterification two.Carboxymethylation reaction is one kind of etherification technology.Cellulose is through carboxylic first
Carboxymethyl cellulose (CMC) is obtained after base, its aqueous solution has thickening, film forming, gluing, water tariff collection, colloid protection, emulsification
And suspend etc. effect, be widely used in the industries such as oil, food, medicine, textile and paper, be most important cellulose ethers it
One.Carboxymethyl cellulose can absorb substantial amounts of water and form gelinite in its surface, carboxymethylcellulomaterials materials it is this
Characteristic is particularly advantageous in wound dressing of the manufacture with absorption and formation gelling performance, and carboxylic is described in WO-A-94/16746
Application of the methylcellulose in wound dressing.
Being presently used for antibacterial or elimination harmful microbe bactericide mainly has natural antibacterial agent (chitosan and its derivative
Thing etc.), inorganic antiseptic (silver-series antibacterial agent etc.) and organic antibacterial agent (quaternary ammonium salt, guanidinesalt class, phenolic ether class, pyroles etc.).
Silver be it is a kind of with broad spectrum of activity, can be compatible with mammalian tissues useful antiseptic, silver salt solution can pass through broken ring bacterium
Cell membrane and make bacterium enzyme denaturation and sterilized, will silver incorporation wound dressing in make wound dressing have silver anti-microbial property
The suggestion of advantage is a lot, and many patent documents, which are reported, to be added to silver in calcium alginate sodium or carboxymethyl cellulose to make
Standby antiseptic dressing, such as GB-A-1,328,088, WO-A-91/11206, WO-A-92/22285, JP-A-4146218, WO-A-02/
36866th, WO-A-01/24839, US8828424B2 and CN102580136B.However, also there is many experts to think that silver ion can be from
Dressing, which is separated out, enters human body, easily causes the destruction of skin surface caused by protein coagulation, health may be caused not
, there is potential safety hazard in good influence.Natural antibacterial agent chitosan is also the effective antiseptic of a class, patent CN 102675651B, CN
103920180B discloses the anti-bacterial hydrogel of chitosan graft biguanides formation, and anti-bacterial hydrogel antiseptic prepared by this method is not
Separate out, security is good, but hydrogel preparation technology is complicated, and liquid absorption is small, meanwhile, chitosan is animal sources product, is existed
, still there is potential safety hazard in immunogenicity.
Guanidinesalt class is a kind of conventional organic antibacterial agent, and patent 102462860 discloses a kind of fibre with antibacterial action
Class wound dressing and preparation method thereof is tieed up, the dressing is the fabric that the fiber that surface spraying has poly hexamethylene biguanide solution is made
Or the fabric of poly hexamethylene biguanide solution is coated with, the dressing can be used continuously 7 days.But poly hexamethylene biguanide into
Divide simply absorption on fabric, easily separate out, the anti-microbial property of dressing can decline after precipitation.
The content of the invention
Based on this, the invention reside in the defect for overcoming prior art, there is provided a kind of antibacterial wound dressing, the antibacterial wound
Dressing has excellent antibacterial effect, and antibiotic rate is not less than 99% within seven days；Its liquid absorption is big, liquid energy power is locked after imbibition by force, moisturizing
Ability is good；Good biocompatibility, no sensitization, it is non-stimulated, without immunogenicity.
Another object of the present invention is to provide the preparation method of the antibacterial wound dressing.
Technical scheme is as follows：
A kind of antibacterial wound dressing, structure such as formula 1：
Wherein, R1、R2、R3、R4For-OH ,-OCH2COONa, R5For-CH2OH or-CH2OCH2COONa, R6For：
Wherein, R7For Cl-、H2PO4 -、CH3CH2COO-、CH2OH(CHOH)4COO-, n=200~800, m=10~100.
The main chain of antibacterial wound dressing of the present invention is carboxymethyl cellulose, and side chain is guanidine compound, and carboxymethyl is fine
Dimension element can absorb substantial amounts of water and form gelinite in its surface, and this characteristic of carboxymethylcellulomaterials materials has in manufacture
Have particularly advantageous in the wound dressing for absorbing and forming gelling performance；Guanidine compound is that the sterilization of environment-friendly type macromolecule polymer disappears
Toxic agent, is also a kind of efficient broad spectrum antimicrobial agent, the premium properties such as it has work fast, property stable, soluble in water, and
It can use at normal temperatures, it is long-term antibacterial, nontoxic, odorless, non-corrosiveness, have no side effect, use safety.Antibacterial wound of the present invention
Mouth dressing has excellent antibacterial effect, and seven days antibiotic rates are not less than 99%, and the liquid absorption of antibacterial wound dressing is big, after imbibition
Lock liquid energy power strong, moisture-retaining capacity is good.In addition antibacterial wound dressing good biocompatibility of the present invention, no sensitization, it is non-stimulated,
Without immunogenicity.
In one of the embodiments, n=200~500.When the degree of polymerization of antibacterial wound dressing is 200~500,
The imbibition ability of antibacterial wound dressing is preferable.
In one of the embodiments, the antibacterial wound dressing by carboxymethyl cellulose and guanidine compound through amidatioon
Reaction is obtained, the carboxymethyl cellulose substitution value be 0.1~0.6, the guanidine compound grafting amount be 0.2%~
10.0%.
In one of the embodiments, the substitution value of carboxymethyl cellulose is 0.2~0.5.
In one of the embodiments, the guanidine compound is polyhexamethylene guanide and its derivative, polyhexamethylene
Biguanides and its derivative.
In one of the embodiments, the guanidine compound is Polyhaxemethylenguanidine Hydrochloride, hydrochloric polyhexamethylene pair
Guanidine, phosphoric acid polyhexamethylene guanide, polyhexamethylene guanidine propionate, gluconic acid polyhexamethylene guanide.
In one of the embodiments, the guanidine compound grafting amount is 0.5%~9.0%.
In one of the embodiments, the guanidine compound grafting amount is 0.5%~5.0%.
In one of the embodiments, the raw material of the carboxymethyl cellulose is tencel fiber, cotton fiber, bamboo fibre or viscous
Glue fiber.
S1, using solvent method, using water and ethanol as reaction medium, it is fine that cellulose and sodium hydroxide obtain alkali through quaternization
Dimension, then prepare the carboxymethyl cellulose that substitution value is 0.1~0.6 with the etherified reaction of monoxone；
S2, preparation mass/volume are than carboxymethyl cellulose-organic solvent suspension for 0.5~40%；
S3, addition activator or acid regulator and condensing agent, Ran Houjia into carboxymethyl cellulose-organic solvent suspension
Enter guanidine compound, 0.5~48h is reacted at 0~50 DEG C；
S4, the unreacted small-molecule substance of removing, are dried to obtain antibacterial wound dressing.
In one of the embodiments, the organic solvent of the carboxymethyl cellulose-organic solvent suspension is toluene, third
Ketone, tetrahydrofuran, chloroform, dimethyl acetamide, dimethylformamide, dimethyl sulfoxide (DMSO), dichloromethane, chloroform, acetonitrile,
At least one of pyridine.
In one of the embodiments, the activator is n-hydroxysuccinimide or 1- hydroxy benzo triazoles.
In one of the embodiments, the consumption of the activator is the 0.1%~10% of carboxymethyl cellulose quality.
In one of the embodiments, the condensing agent is water-soluble carbodiimide class compound.Specifically, the water
Dissolubility carbodiimides can be 1- (3- dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides, N, the rings of N'- bis-
Hexyl carbodiimide, N, N'- DICs.
In one of the embodiments, the consumption of the condensing agent is the 0.15%~15% of carboxymethyl cellulose quality.
In one of the embodiments, the acid regulator is inorganic acid such as hydrochloric acid, sulfuric acid.
In one of the embodiments, the acid regulator is the PH of control reaction system 4~6.
In one of the embodiments, the step S1 is：
1) degree of polymerization is mixed for 300~1200 raw material tencel with sodium hydrate aqueous solution, ethanol, controls reaction range
15~40 DEG C, react 30~90min；The raw material tencel, sodium hydroxide, water, the mass ratio of ethanol are：1：(0.3~3.0)：
(3.0~6.0)：(6.0~9.0)；
2) monoxone is added, controlling reaction temperature is 30 DEG C~54 DEG C 1~3h of reaction, then heats to 55 DEG C~75 DEG C instead
Answer 1~3h；Raw material tencel, chloroacetic mass ratio are 1：(0.2~1)；
3) add glacial acetic acid to be neutralized, reaction temperature is 20 DEG C~45 DEG C, reacts 30~90min, raw material tencel, ice vinegar
The mass/volume ratio of acid is 1：0.25, then washed through second alcohol and water, dry, obtain carboxymethyl cellulose.
In one of the embodiments, the step S2 is：Carboxymethyl cellulose is mixed with organic solvent, matter is prepared
Amount/volume ratio is 0.5~40% carboxymethyl cellulose-organic solvent suspension.
In one of the embodiments, the carboxymethyl cellulose-organic solvent suspension mass/volume ratio be 10~
30%.
In one of the embodiments, the step S3 is：Contracting is added into carboxymethyl cellulose-organic solvent suspension
Mixture, activator, guanidine compound, controlling reaction temperature are 20~50 DEG C of progress amidation process, react 30~240min, its
In, the condensing agent, activator, the mass ratio of guanidine compound and carboxymethyl cellulose are：Carboxymethyl cellulose：Condensing agent：
Activator：Guanidine compound=1：(0.015~0.15)：(0.01~0.1)：(0.02~6).
In one of the embodiments, the reaction temperature of the step S3 is 35 DEG C, and the reaction time is 120min.
In one of the embodiments, the step S4 is：The mixed solution for adding second alcohol and water is washed, and ethanol is dense
Spend for 83%~86%, 20min are washed in 35 DEG C~45 DEG C and remove unreacted small-molecule substances, 50 DEG C of drying obtain antibacterial wound
Mouth dressing.
The invention also discloses application of the antibacterial wound dressing in acute and chronic wounds nursing.
In one of the embodiments, the antibacterial wound dressing is braid or non-woven fabrics.
The beneficial effects of the present invention are：Guanidine compound is grafted to carboxymethyl cellulose by the present invention by amidation process
A kind of high-efficiency antimicrobial wound dressing is prepared on element, the high-efficiency antimicrobial wound dressing has the imbibition of carboxymethyl cellulose concurrently
Hurry up, the antibacterial characteristics of the characteristic such as water holding capacity is good, colloid protectiveness is good and guanidine compound, the present invention is by controlling guanidine
The grafting amount of class compound causes the antibacterial wound dressing prepared to have excellent antibacterial effect, and antibiotic rate is not less than within seven days
99%, and the liquid absorption of antibacterial wound dressing is big, liquid energy power is locked after imbibition by force, moisture-retaining capacity is good, and antibacterial of the present invention is hindered
Mouthful dressing good biocompatibility, no sensitization, it is non-stimulated, without immunogenicity.
Brief description of the drawings
Fig. 1 is the structural formula of antibacterial wound dressing.
Fig. 2 is the infrared spectrogram of carboxymethyl cellulose and antibacterial wound dressing.
Embodiment
The present invention will be described in detail with reference to the accompanying drawings and examples.Following examples only express the present invention's
Embodiment, it describes more specific and detailed, but therefore can not be interpreted as the limitation to the scope of the claims of the present invention, in every case
The technical scheme obtained using the form of equivalent substitution or equivalent transformation, all should fall within the scope and spirit of the invention.
Embodiment 1
Raw material used in following examples is unless otherwise indicated, be ordinary commercial products.
Following examples are adopted to be measured to the substitution value of carboxymethyl cellulose with the following method：By standard GB1904-
2005 food additives sodium carboxymethylcellulose methods 5.5 are measured.
The guanidine compound grafting amount that following examples adopt with the following method to antibacterial wound dressing is measured：By standard
GB 26367-2010 guanidine disinfectant sanitary standard appendix As are measured.
Embodiment 1
A kind of antibacterial wound dressing, its preparation process is as follows：
S1, raw material tencel and sodium hydrate aqueous solution, the ethanol of the degree of polymerization 600~1000 mixed, control reaction range
30~40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg,
5.0Kg、7.0Kg.0.3Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C
~65 DEG C of reaction 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second
Alcohol and water is washed, drying, obtains carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.3, polymerization
Spend for 421.
S2, carboxymethyl cellulose mixed with organic solvent-acetone and water, prepare mass/volume than the carboxylic first for 20%
Base cellulose-organic solvent suspension.
S3, addition condensing agent EDS, activator NHS, guanidine compound into carboxymethyl cellulose-organic solvent suspension
Polyhexamethylene biguanidine hydrochloride (PHMB, m=50~80), controlling reaction temperature is 30 DEG C of progress amidation process, reaction
120min, wherein, the condensing agent, activator, the mass ratio of guanidine compound and carboxymethyl cellulose are：Carboxymethyl cellulose
Element：Condensing agent：Activator：Guanidine compound=1：0.04：0.025：0.25.
S4, the mixed solution of addition second alcohol and water are washed, and concentration of alcohol is 83%~86%, is washed in 35 DEG C~45 DEG C
Wash 20min and remove unreacted small-molecule substance, 50 DEG C of drying obtain antibacterial wound dressing.After measured, the antibacterial wound is applied
PHMB grafting amount is 2.0% in material.
The raw materials used tencel of the present embodiment and the infrared spectrogram of obtained antibacterial wound dressing are shown in Fig. 2.Can from Fig. 2
Know, compared to raw material tencel, the antibacterial wound dressing prepared by the present embodiment is in 1581cm-1Neighbouring and 1685cm-1Nearby occur
Amido link characteristic peak, shows that PHMB has successfully been grafted on carboxymethyl cellulose and has obtained target product.
Embodiment 2
A kind of antibacterial wound dressing, its preparation process is as follows：
S1, raw material tencel and sodium hydrate aqueous solution, the ethanol of the degree of polymerization 600~1000 mixed, control reaction range
30~40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg,
5.0Kg、7.0Kg.0.3Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C
~65 DEG C of reaction 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second
Alcohol and water is washed, drying, obtains carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.3, polymerization
Spend for 421.
S2, carboxymethyl cellulose mixed with organic solvent-acetone and water, prepare mass/volume than the carboxylic first for 20%
Base cellulose-organic solvent suspension.
S3, addition condensing agent EDS, activator NHS, guanidine compound into carboxymethyl cellulose-organic solvent suspension
Phosphoric acid polyhexamethylene guanide, controlling reaction temperature is 30 DEG C of progress amidation process, reacts 60min, wherein, the condensing agent,
The mass ratio of activator, guanidine compound and carboxymethyl cellulose is：Carboxymethyl cellulose：Condensing agent：Activator：Guanidine chemical combination
Thing=1：0.108：0.066：1.5.
S4, the mixed solution of addition second alcohol and water are washed, and concentration of alcohol is 83%~86%, is washed in 37 DEG C~43 DEG C
Wash 20min and remove unreacted small-molecule substance, 50 DEG C of drying obtain antibacterial wound dressing.After measured, the antibacterial wound is applied
The grafting amount of phosphoric acid polyhexamethylene guanide is 6.5% in material.
Embodiment 3
A kind of antibacterial wound dressing, its preparation process is as follows：
S1, raw material tencel and sodium hydrate aqueous solution, the ethanol of the degree of polymerization 600~1000 mixed, control reaction range
30~40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1Kg, 2.0Kg, 5.0Kg,
7.0Kg.0.3Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C~65 DEG C
React 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second alcohol and water
Washed, dry, obtain carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.3, and the degree of polymerization is
421。
S2, carboxymethyl cellulose mixed with organic solvent-acetone and water, prepare mass/volume than the carboxylic first for 20%
Base cellulose-organic solvent suspension.
S3, addition condensing agent EDS, activator NHS, guanidine compound into carboxymethyl cellulose-organic solvent suspension
Polyhexamethylene guanidine propionate, controlling reaction temperature is 30 DEG C of progress amidation process, reacts 60min, wherein, the condensing agent,
The mass ratio of activator, guanidine compound and carboxymethyl cellulose is：Carboxymethyl cellulose：Condensing agent：Activator：Guanidine chemical combination
Thing=1：0.072：0.044：0.6.
S4, the mixed solution of addition second alcohol and water are washed, and concentration of alcohol is 83%~86%, is washed in 37 DEG C~43 DEG C
Wash 20min and remove unreacted small-molecule substance, 50 DEG C of drying obtain antibacterial wound dressing.After measured, the antibacterial wound is applied
The grafting amount of polyhexamethylene guanidine propionate is 3.6% in material.
Embodiment 4
A kind of antibacterial wound dressing, its preparation process is as follows：
S1, raw material tencel and sodium hydrate aqueous solution, the ethanol of the degree of polymerization 600~1000 mixed, control reaction range
30~40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg,
5.0Kg、7.0Kg.0.3Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C
~65 DEG C of reaction 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second
Alcohol and water is washed, drying, obtains carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.3, polymerization
Spend for 421.
S2, carboxymethyl cellulose mixed with organic solvent-acetone and water, prepare mass/volume than the carboxylic first for 20%
Base cellulose-organic solvent suspension.
S3, addition condensing agent EDS, activator NHS, guanidine compound into carboxymethyl cellulose-organic solvent suspension
Gluconic acid polyhexamethylene guanide, controlling reaction temperature is 300 DEG C of progress amidation process, reacts 60min, wherein, the contracting
Mixture, activator, the mass ratio of guanidine compound and carboxymethyl cellulose are：Carboxymethyl cellulose：Condensing agent：Activator：Guanidine
Class compound=1：0.15：0.1：3.2.
S4, the mixed solution of addition second alcohol and water are washed, and concentration of alcohol is 83%~86%, is washed in 37 DEG C~43 DEG C
Wash 20min and remove unreacted small-molecule substance, 50 DEG C of drying obtain antibacterial wound dressing.After measured, the antibacterial wound is applied
The grafting amount of gluconic acid polyhexamethylene guanide is 8.7% in material.
Embodiment 5
The raw material tencel of the degree of polymerization 600~1000 is mixed with sodium hydrate aqueous solution, ethanol, control reaction range 30~
40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg, 5.0Kg,
7.0Kg.0.20Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C~65 DEG C
React 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second alcohol and water
Washed, dry, obtain carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.18, and the degree of polymerization is
537。
By step S2, S3, S4 methods described polyhexamethylene biguanidine hydrochloride (PHMB) of embodiment 1 to the carboxylic first prepared
After measured, PHMB grafting amount is 0.21% to base cellulose in the antibacterial wound dressing.
Embodiment 6
The raw material tencel of the degree of polymerization 600~1000 is mixed with sodium hydrate aqueous solution, ethanol, control reaction range 30~
40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg, 5.0Kg,
7.0Kg.0.55Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C~65 DEG C
React 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second alcohol and water
Washed, dry, obtain carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.48, and the degree of polymerization is
368。
By step S2, S3, S4 methods described polyhexamethylene biguanidine hydrochloride (PHMB) of embodiment 1 to the carboxylic first prepared
After measured, PHMB grafting amount is 3.8% to base cellulose in the antibacterial wound dressing.
Embodiment 7
A kind of antibacterial wound dressing, its preparation process is as follows：
S1, raw material tencel and sodium hydrate aqueous solution, the ethanol of the degree of polymerization 600~1000 mixed, control reaction range
30~40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg,
5.0Kg、7.0Kg.0.7Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C
~65 DEG C of reaction 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second
Alcohol and water is washed, drying, obtains carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.6, polymerization
Spend for 320.
By step S2, S3, S4 methods described polyhexamethylene biguanidine hydrochloride (PHMB) of embodiment 1 to the carboxylic first prepared
After measured, PHMB grafting amount is 7.2% to base cellulose in the antibacterial wound dressing.
Embodiment 8
From the raw material viscose rayon of the degree of polymerization 300~600, carboxymethyl cellulose is prepared according to the methods described of embodiment 1,
The substitution value of carboxymethyl cellulose is 0.33 after measured, and the degree of polymerization is 227, then prepares antibacterial wound by the methods described of embodiment 1
Dressing, after measured, PHMB grafting amount is 2.5% in the antibacterial wound dressing.
Embodiment 9
From the raw material cotton fiber of the degree of polymerization 1000~1200, carboxymethyl cellulose is prepared according to the methods described of embodiment 1,
After measured the substitution value of carboxymethyl cellulose be 0.25, the degree of polymerization is 694, then by embodiment methods described prepare antibacterial wound apply
Material, after measured, PHMB grafting amount is 1.1% in the antibacterial wound dressing.
Comparative example 1
A kind of antibacterial wound dressing, its preparation process is as follows：
The raw material cotton fiber of the degree of polymerization 1500~1800 is mixed with sodium hydrate aqueous solution, ethanol, reaction range is controlled
30~40 DEG C, react 60min；The raw material tencel, sodium hydroxide, water, the quality of ethanol be respectively 1.0Kg, 2.0Kg,
5.0Kg、7.0Kg.0.1Kg monoxones are added, controlling reaction temperature is 40 DEG C~50 DEG C reaction 60min, then heats to 55 DEG C
~65 DEG C of reaction 60min.Add 0.25L glacial acetic acid to be neutralized, reaction temperature is 25 DEG C~30 DEG C, reacts 60min, then through second
Alcohol and water is washed, drying, obtains carboxymethyl cellulose.After measured, the substitution value of the carboxymethyl cellulose is 0.08, polymerization
Spend for 877.
By step S2, S3, S4 methods described polyhexamethylene biguanidine hydrochloride (PHMB) of embodiment 1 to the carboxylic first prepared
After measured, PHMB grafting amount is 0.12% to base cellulose in the antibacterial wound dressing.
Water absorption, biocompatibility, antibiotic property are carried out to antibacterial wound dressing prepared by embodiment 1~9, comparative example 1 to survey
Examination, testing result is shown in Table 1, and testing standard or method are as follows：
(1) liquid absorption：The sample 0.3g through 80 DEG C of forced air drying 2h is weighed in surface plate, be slowly added dropwise experimental liquid A (by
The solution composition of sodium chloride and calcium chloride, the solution is sodium ion containing 142mmol and 2.5mmol calcium ion.The solution from
Sub- content is equivalent to human serum or wound fluid.Deionized water dissolving 8.298g sodium chloride and 0.368g are used in volumetric flask
Calcium chloride dihydrate is simultaneously diluted to 1L), until sample is in the state of imbibition saturation, the weight W inhaled after experimental liquid A is weighed, is calculated
Liquid absorption, calculation formula：(W-0.3)/0.3*100%.
(2) antibiotic property：The evaluation third portion of GBT 20944.3-2008 antibacterial textile performances：Succusion, tests strain
For enterococcus faecalis (ATCC 51575) and pseudomonas aeruginosa (ATCC 9027).
(3) liquid energy power is locked：50mm*50mm sample is cut, W1 is weighed；Sample is placed in surface plate, added a certain amount of
Experimental liquid A (by the solution composition of sodium chloride and calcium chloride, the solution be sodium ion containing 142mmol and 2.5mmol calcium from
Son.The ion concentration of the solution is equivalent to human serum or wound fluid.Deionized water dissolving 8.298g is used in volumetric flask
Sodium chloride and 0.368g calcium chloride dihydrates are simultaneously diluted to 1L) so that sample is in the state of imbibition saturation；The sample of sum will be saturated with
It is placed in plane, applies 40mmHg pressure (about 1.36kg) 5min to specimen surface (50*50mm), blot and oozed out around sample
Liquid, take out sample weigh W2；Placed on sample and filter paper is removed after enough filter paper, 30min, weigh sample weight W3；
It is calculated as follows and locks liquid energy power：(W3-W1)/(W2-W1) * 100%
The embodiment of table 1 and comparative example antibacterial wound dressing performance test
To verify the biocompatibility of antibacterial wound dressing, cytotoxicity (ISO has also been carried out to antibacterial wound dressing
10993-5:2009), acute toxicity (ISO 10993-11:2006), priming experiments (ISO 10993-10:2010) pierced with skin
Swash property test (ISO 10993-10:2010), test result shows that prepared antibacterial wound dressing biocompatibility is good.
Each technical characteristic of embodiment described above can be combined arbitrarily, to make description succinct, not to above-mentioned reality
The all possible combination of each technical characteristic in example is applied all to be described, for the person of ordinary skill of the art,
On the premise of not departing from present inventive concept, various modifications and improvements can be made, these belong to protection scope of the present invention,
All it is considered to be the scope of this specification record.
Claims (10)
1. a kind of antibacterial wound dressing, it is characterised in that the structure of the antiseptic dressing such as formula 1：
Wherein, R1、R2、R3、R4For-OH ,-OCH2COONa, R5For-CH2OH or-CH2OCH2COONa,
R6For：
Wherein, R7For Cl-、H2PO4 -、CH3CH2COO-、CH2OH(CHOH)4COO-, n=200~800, m=10~100.
2. antibacterial wound dressing according to claim 1, it is characterised in that n=200~500.
3. antibacterial wound dressing according to claim 1, it is characterised in that the antibacterial wound dressing is by carboxymethyl cellulose
Obtained with guanidine compound through amidation process, the carboxymethyl cellulose substitution value is 0.1~0.6, the guanidine compound
Grafting amount is 0.2%~10.0%.
4. antibacterial wound dressing according to claim 3, it is characterised in that the substitution value of carboxymethyl cellulose is 0.2~
0.5。
5. antibacterial wound dressing according to claim 3, it is characterised in that the guanidine compound be polyhexamethylene guanide and
Its derivative, poly hexamethylene biguanide and its derivative.
6. antibacterial wound dressing according to claim 5, it is characterised in that the guanidine compound is hydrochloric polyhexamethylene
Guanidine, polyhexamethylene biguanidine hydrochloride, phosphoric acid polyhexamethylene guanide, polyhexamethylene guanidine propionate, gluconic acid polyhexamethylene guanide.
7. antibacterial wound dressing according to claim 6, it is characterised in that the guanidine compound grafting amount is 0.5%~
5.0%.
8. the preparation method of antibacterial wound dressing described in claim 1-7 any claims, it is characterised in that including following step
Suddenly：
S1, using solvent method, using water and ethanol as reaction medium, cellulose and sodium hydroxide obtain alkali fiber through quaternization,
Again the carboxymethyl cellulose that substitution value is 0.1~0.6 is prepared with the etherified reaction of monoxone；
S2, preparation mass/volume are than carboxymethyl cellulose-organic solvent suspension for 0.5~40%；
S3, addition activator or acid regulator and condensing agent into carboxymethyl cellulose-organic solvent suspension, then add guanidine
Class compound, reacts 0.5~48h at 0~50 DEG C；
S4, the unreacted small-molecule substance of removing, are dried to obtain antibacterial wound dressing.
9. preparation method according to claim 8, it is characterised in that the carboxymethyl cellulose-organic solvent suspension
Organic solvent is toluene, acetone, butanone, tetrahydrofuran, chloroform, dimethyl acetamide, dimethylformamide, dimethyl Asia
At least one of sulfone, dichloromethane, chloroform, acetonitrile, pyridine.
10. application of the antibacterial wound dressing described in claim 1-7 any claims in acute and chronic wounds nursing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710368906.2A CN107137749A (en) | 2017-05-23 | 2017-05-23 | Antibacterial wound dressing and preparation method and application thereof |
Applications Claiming Priority (1)
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2591088A (en) * | 2020-01-08 | 2021-07-21 | Adv Med Solutions Ltd | Antimicrobial fibres |
| CN114343975A (en) * | 2022-01-12 | 2022-04-15 | 河北卫崭医疗科技有限公司 | Wet wound dressing and its prepn |
| CN115094633A (en) * | 2022-05-11 | 2022-09-23 | 惠州华阳医疗器械有限公司 | Antibacterial alginate fiber, preparation method and application |
| CN115141284A (en) * | 2022-08-22 | 2022-10-04 | 安庆市嘉欣医疗用品科技股份有限公司 | Macromolecular derivative, preparation method and application thereof |
| CN115522381A (en) * | 2022-09-30 | 2022-12-27 | 湖南佰欧泰医药有限责任公司 | Preparation process of hydrophilic fiber structure |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675651A (en) * | 2012-04-20 | 2012-09-19 | 常州华联保健敷料有限公司 | Preparation method of chitosan hydrogel for antiseptic dressing |
| CN103724437A (en) * | 2014-01-09 | 2014-04-16 | 福建农林大学 | Multifunctional guanidine salt grafted carboxymethyl cellulose paper-making additive and preparation method thereof |
| CN103920180A (en) * | 2014-03-13 | 2014-07-16 | 上海应用技术学院 | Chitosan hydrogel for antibacterial dressing and preparation method thereof |
| CN104805734A (en) * | 2015-04-10 | 2015-07-29 | 上海应用技术学院 | Paper additive and preparation method thereof |
| CN105061771A (en) * | 2015-07-30 | 2015-11-18 | 山东惠民力洁生物科技有限公司 | Preparation method of disinfecting material namely methyl guanidine chitosan hydrochloride |
| US20160060362A1 (en) * | 2006-06-02 | 2016-03-03 | Shenda Baker | Chitosan-derivative compounds and methods of controlling microbial populations |
-
2017
- 2017-05-23 CN CN201710368906.2A patent/CN107137749A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160060362A1 (en) * | 2006-06-02 | 2016-03-03 | Shenda Baker | Chitosan-derivative compounds and methods of controlling microbial populations |
| CN102675651A (en) * | 2012-04-20 | 2012-09-19 | 常州华联保健敷料有限公司 | Preparation method of chitosan hydrogel for antiseptic dressing |
| CN103724437A (en) * | 2014-01-09 | 2014-04-16 | 福建农林大学 | Multifunctional guanidine salt grafted carboxymethyl cellulose paper-making additive and preparation method thereof |
| CN103920180A (en) * | 2014-03-13 | 2014-07-16 | 上海应用技术学院 | Chitosan hydrogel for antibacterial dressing and preparation method thereof |
| CN104805734A (en) * | 2015-04-10 | 2015-07-29 | 上海应用技术学院 | Paper additive and preparation method thereof |
| CN105061771A (en) * | 2015-07-30 | 2015-11-18 | 山东惠民力洁生物科技有限公司 | Preparation method of disinfecting material namely methyl guanidine chitosan hydrochloride |
Non-Patent Citations (4)
| Title |
|---|
| 中国食品添加剂和配料协会编著: "《十一五"国家重点图书出版规划项目 食品添加剂手册 第3版》", 30 September 2012, 中国轻工业出版社 * |
| 于广利等: "《糖药物学》", 31 October 2012, 中国海洋大学出版社 * |
| 宋玉民等: "壳聚糖的改性及抑菌性研究", 《西北师范大学学报(自然科学版)》 * |
| 贾丽华等: "《化学工程与工艺综合实验》", 30 September 2009, 哈尔滨工程大学出版社 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2591088A (en) * | 2020-01-08 | 2021-07-21 | Adv Med Solutions Ltd | Antimicrobial fibres |
| GB2591088B (en) * | 2020-01-08 | 2024-07-03 | Adv Med Solutions Ltd | Antimicrobial fibres |
| CN114343975A (en) * | 2022-01-12 | 2022-04-15 | 河北卫崭医疗科技有限公司 | Wet wound dressing and its prepn |
| CN115094633A (en) * | 2022-05-11 | 2022-09-23 | 惠州华阳医疗器械有限公司 | Antibacterial alginate fiber, preparation method and application |
| CN115141284A (en) * | 2022-08-22 | 2022-10-04 | 安庆市嘉欣医疗用品科技股份有限公司 | Macromolecular derivative, preparation method and application thereof |
| CN115522381A (en) * | 2022-09-30 | 2022-12-27 | 湖南佰欧泰医药有限责任公司 | Preparation process of hydrophilic fiber structure |
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