JP2021504509A - 光に応答して向上した抗菌活性を有するスターポリマー - Google Patents
光に応答して向上した抗菌活性を有するスターポリマー Download PDFInfo
- Publication number
- JP2021504509A JP2021504509A JP2020528011A JP2020528011A JP2021504509A JP 2021504509 A JP2021504509 A JP 2021504509A JP 2020528011 A JP2020528011 A JP 2020528011A JP 2020528011 A JP2020528011 A JP 2020528011A JP 2021504509 A JP2021504509 A JP 2021504509A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- group
- singlet oxygen
- core
- cation
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 202
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 48
- 230000004044 response Effects 0.000 title claims description 12
- 239000004417 polycarbonate Substances 0.000 claims abstract description 128
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 128
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 113
- 150000001768 cations Chemical class 0.000 claims abstract description 23
- 125000000524 functional group Chemical group 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 59
- -1 phthalocyanines Chemical class 0.000 claims description 57
- 125000002091 cationic group Chemical group 0.000 claims description 43
- 244000052769 pathogen Species 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 34
- 125000005647 linker group Chemical group 0.000 claims description 30
- 230000001717 pathogenic effect Effects 0.000 claims description 30
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 21
- 241000894006 Bacteria Species 0.000 claims description 18
- 239000012528 membrane Substances 0.000 claims description 18
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 17
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 16
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 12
- 150000004032 porphyrins Chemical class 0.000 claims description 11
- 241000192125 Firmicutes Species 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 10
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 8
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 8
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 8
- 229950000688 phenothiazine Drugs 0.000 claims description 8
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 8
- 231100000331 toxic Toxicity 0.000 claims description 8
- 230000002588 toxic effect Effects 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 125000001165 hydrophobic group Chemical group 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical class 0.000 claims description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 150000002990 phenothiazines Chemical class 0.000 claims description 3
- 150000004053 quinones Chemical class 0.000 claims description 3
- 150000003732 xanthenes Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 2
- 229920001817 Agar Polymers 0.000 description 31
- 239000008272 agar Substances 0.000 description 31
- 230000000670 limiting effect Effects 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000003642 reactive oxygen metabolite Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 230000002147 killing effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 150000002576 ketones Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 208000037408 Device failure Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000012988 Dithioester Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZYKJMNKVKCHYPR-UHFFFAOYSA-N [4-(chloromethyl)phenyl]methyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate Chemical compound C=1C=C(CCl)C=CC=1COC(=O)C1(C)COC(=O)OC1 ZYKJMNKVKCHYPR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- VFHDWGAEEDVVPD-UHFFFAOYSA-N chembl507897 Chemical compound C1=CC(O)=CC=C1C(C1=CC=C(N1)C(C=1C=CC(O)=CC=1)=C1C=CC(=N1)C(C=1C=CC(O)=CC=1)=C1C=CC(N1)=C1C=2C=CC(O)=CC=2)=C2N=C1C=C2 VFHDWGAEEDVVPD-UHFFFAOYSA-N 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/23—Solid substances, e.g. granules, powders, blocks, tablets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
- C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/0241—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1641—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1658—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/42—Chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- 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
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/24—Medical instruments, e.g. endoscopes, catheters, sharps
-
- 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
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/25—Rooms in buildings, passenger compartments
-
- 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
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/26—Textiles, e.g. towels, beds, cloths
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
- C08G83/004—After treatment of dendrimers
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Plant Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
により特徴付けられる構造を有することができ、
式中、R1は、第2の官能基を表すことができる。したがって、ROPは、次式2:
により特徴付けられるポリカーボネート構造を形成することができ、
式中、R1は、第2の官能基を表すことができ、「X」は、一重項酸素発生コア104への結合を表すことができ、「n」は、5以上および1000以下の整数を表すことができる。例えば、第2の官能基は、4−メチルベンジルクロリドとすることができ、それによって2−オキソ−5−メチル−1,3−ジオキサン−5−カルボン酸4−(クロロメチル)ベンジルエステル(「MTC−OBnCl」)の1つまたは複数のカーボネートを提供する。その後、404での重合は、MTC−OBnClカーボネートのROPを含み、次式3:
により特徴付けられるポリカーボネート構造を形成することができ、
式中、「X」は、一重項酸素発生コア104への結合を表すことができ、「n」は、5以上および1000以下の整数を表すことができる。上述の例では、第1の連結基208は、404での重合の結果として形成される。しかし、本明細書に記載されるように、404での前記重合後に第1の連結基208を形成することもできる。同様に、1つまたは複数の実施形態では、第2の官能基は、404での重合の前に1つまたは複数のカーボネートに共有結合することができるが、他方、いくつかの実施形態では、第2の官能基は、404での重合後にポリカーボネート構造に共有結合することができる。
Claims (25)
- ポリマーであって、
一重項酸素発生部を有し、光照射時に一重項酸素種を発生するコア、および
前記コアに共有結合した複数のポリカーボネート・アームであって、分解可能であり、カチオンを含み、抗菌機能を有する、前記複数のポリカーボネート・アーム
を含むポリマー。 - 前記コアが、ポルフィリン、フタロシアニン、フェノチアジン、キサンテンおよびキノンからなる群から選択される分子から誘導される、請求項1に記載のポリマー。
- 4つのポリカーボネート・アームを含む、請求項1に記載のポリマー。
- 前記カチオンが、プロトン化第一級アミンカチオン、プロトン化第二級アミンカチオン、プロトン化第三級アミンカチオン、第四級アンモニウムカチオン、イミダゾリウムカチオン、プロトン化第一級ホスフィンカチオン、プロトン化第二級ホスフィンカチオン、プロトン化第三級ホスフィンカチオンおよび第四級ホスホニウムカチオンからなる群から選択される、請求項1に記載のポリマー。
- 前記カチオンが、前記第四級アンモニウムカチオンである、請求項4に記載のポリマー。
- 前記複数のポリカーボネート・アームが、疎水性基をさらに含む、請求項4に記載のポリマー。
- 前記複数のポリカーボネート・アームが、次式1:
式中、Xが、前記コアへの結合を表し、Rが、窒素カチオンおよびリンカチオンからなる第1の群から選択される前記カチオンを表し、Hが、水素および前記ポリマーの架橋を促進する第2の官能基からなる第2の群から選択され、nが、5以上および1000以下の整数である、請求項2に記載のポリマー。 - 前記コアが、次式2:
式中、Lが、エーテル基を含む連結基を表し、Aが、前記複数のポリカーボネート・アームからの1つのポリカーボネート・アームを表す、請求項7に記載のポリマー。 - 前記ポリマーが、次式1:
式中、nが、5以上および1000以下の整数であり、Hが、水素および前記ポリマーの架橋を促進する第2の官能基からなる群から選択される、請求項1に記載のポリマー。 - 方法であって、
複数のカーボネートを、一重項酸素発生コアと重合することにより複数の分解性ポリカーボネート・アームを形成することであって、前記一重項酸素発生コアは、光の照射に応答して一重項酸素種を発生する、前記形成すること、および
官能基を、前記複数の分解性ポリカーボネート・アームからの1つの分解性ポリカーボネート・アームと共有結合することにより、カチオン性部分を生成すること
を含む方法。 - 前記官能基が、アミン、ホスフィンおよびイミダゾールからなる群から選択される化学構造を含む、請求項10に記載の方法。
- 前記生成することが、アセチル基の存在下で前記官能基を前記分解性ポリカーボネート・アームに結合することを含む、請求項11に記載の方法。
- 前記分解性ポリカーボネート・アームが、次式1:
式中、Xが、前記一重項酸素発生コアへの結合を表し、Rが、前記カチオン性部分を表し、nが、5以上および1000以下の整数であり、Hが、水素および前記分解性ポリカーボネート・アームの架橋を促進する第3の官能基からなる第2の群から選択される、請求項12に記載の方法。 - 一重項酸素発生分子を第1の官能基と重合することにより前記一重項酸素発生コアを調製することをさらに含み、前記一重項酸素発生分子が、ポルフィリン、フタロシアニン、フェノチアジン、キサンテンおよびキノンからなる第3の群から選択される、請求項13に記載の方法。
- 前記第1の官能基が、アルコール基であり、調製した前記一重項酸素発生コアが、ヒドロキシル基を含む、請求項14に記載の方法。
- 膜形成用組成物であって、
溶媒、ならびに
前記膜形成用組成物の5重量%以上および前記膜形成用組成物の20重量%以下を構成するポリマーであって、前記ポリマーが、前記溶媒に分散しており、
前記ポリマーが、
一重項酸素発生部を有し、光照射時に一重項酸素種を発生するコア、および
前記コアに共有結合した複数のポリカーボネート・アームであって、分解可能であり、カチオンを含み、抗菌官能性を有する、前記複数のポリカーボネート・アーム
を含む、前記ポリマー
を含む膜形成用組成物。 - グラム陰性細菌、グラム陽性細菌、真菌および酵母からなる群から選択される病原体にとって毒性である、請求項16に記載の膜形成用組成物。
- 前記コアが、ポルフィリン、フタロシアニン、フェノチアジン、キサンテンおよびキノンからなる第1の群から選択される分子から誘導され、前記カチオンが、窒素カチオンおよびリンカチオンからなる第2の群から選択される、請求項17に記載の膜形成用組成物。
- 表面処理された物品を形成する方法であって、
物品の表面上に膜形成用組成物を配置することであって、
前記膜形成用組成物が、
溶媒、ならびに
前記膜形成用組成物の5重量%以上および前記膜形成用組成物の20重量%以下を構成するポリマーであって、前記ポリマーが、前記溶媒に分散しており、
前記ポリマーが、
一重項酸素発生部を有し、光照射時に一重項酸素種を発生するコア、および
前記コアに共有結合した複数のポリカーボネート・アームであって、分解可能であり、カチオンを含み、抗菌機能を有する、前記複数のポリカーボネート・アーム
を含む、前記ポリマー
を含む、前記配置すること、ならびに
前記物品の前記表面から前記溶媒を除去すること
を含む方法。 - 前記膜形成用組成物が、グラム陰性細菌、グラム陽性細菌、真菌および酵母からなる群から選択される病原体にとって毒性である、請求項19に記載の方法。
- 前記コアが、ポルフィリン、フタロシアニン、フェノチアジン、キサンテンおよびキノンからなる第1の群から選択される分子から誘導され、前記カチオンが、窒素カチオンおよびリンカチオンからなる第2の群から選択される、請求項20に記載の方法。
- 病原体を死滅させる方法であって、
前記病原体をポリマーに接触させることであって、前記ポリマーが、
一重項酸素発生部を有し、光照射時に一重項酸素種を発生するコア、および
前記コアに共有結合した複数のポリカーボネート・アームであって、分解可能であり、カチオンを含み、抗菌機能を有する、前記複数のポリカーボネート・アームを含み、
前記病原体を前記ポリマーに接触させることが、前記病原体の膜を静電的に破壊する、前記接触させること
を含む方法。 - 前記ポリマーに前記光を照射すること、および
前記コアを介して前記一重項酸素種を発生すること
をさらに含む、請求項22に記載の方法。 - 前記病原体が、グラム陰性細菌、グラム陽性細菌、真菌および酵母からなる群から選択される、請求項23に記載の方法。
- 前記コアが、ポルフィリン、フタロシアニン、フェノチアジン、キサンテンおよびキノンからなる第1の群から選択される分子から誘導され、前記カチオンが、窒素カチオンおよびリンカチオンからなる第2の群から選択される、請求項24に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/824,250 | 2017-11-28 | ||
US15/824,250 US10561146B2 (en) | 2017-11-28 | 2017-11-28 | Star polymers with enhanced antimicrobial activity in response to light |
PCT/IB2018/058797 WO2019106459A1 (en) | 2017-11-28 | 2018-11-09 | Star polymers with enhanced antimicrobial activity in response to light |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2021504509A true JP2021504509A (ja) | 2021-02-15 |
JP2021504509A5 JP2021504509A5 (ja) | 2021-03-25 |
JP7266351B2 JP7266351B2 (ja) | 2023-04-28 |
Family
ID=66633916
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020528011A Active JP7266351B2 (ja) | 2017-11-28 | 2018-11-09 | 抗菌性ポリマーおよびその生成方法、膜形成組成物、並びに、表面処理された物品の形成方法 |
Country Status (5)
Country | Link |
---|---|
US (2) | US10561146B2 (ja) |
JP (1) | JP7266351B2 (ja) |
DE (1) | DE112018006058T5 (ja) |
GB (1) | GB2580240B (ja) |
WO (1) | WO2019106459A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10561146B2 (en) * | 2017-11-28 | 2020-02-18 | International Business Machines Corporation | Star polymers with enhanced antimicrobial activity in response to light |
FR3090271B1 (fr) * | 2018-12-19 | 2021-03-05 | Commissariat A L’Energie Atomique Et Aux Energies Alternatives Cea | Procédé de préparation d’un matériau biocide, bactéricide et/ou bactériostatique |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007526933A (ja) * | 2003-11-21 | 2007-09-20 | ザ ユニバーシティー オブ シェフィールド | 多分岐ポリマー |
CN103501769A (zh) * | 2011-03-18 | 2014-01-08 | 国际商业机器公司 | 星形聚合物纳米壳及其制备方法 |
US8765098B2 (en) * | 2010-03-30 | 2014-07-01 | International Business Machines Corporation | Star polymers, methods of preparation thereof, and uses thereof |
US20140370064A1 (en) * | 2013-06-16 | 2014-12-18 | International Business Machines Corporation | Film-forming compositions of self-crosslinkable nanogel star polymers |
CN104861172A (zh) * | 2015-04-28 | 2015-08-26 | 同济大学 | 一种以卟啉为核的具有荧光效应、pH响应性和温度响应性的星型共聚物的制备方法 |
JP2016522274A (ja) * | 2013-04-09 | 2016-07-28 | インターナショナル・ビジネス・マシーンズ・コーポレーションInternational Business Machines Corporation | 抗菌性のカチオン性ポリカーボネート |
US20160338356A1 (en) * | 2015-05-19 | 2016-11-24 | International Business Machines Corporation | Antimicrobial guanidinium and thiouronium functionalized polymers |
JP2016222664A (ja) * | 2013-04-09 | 2016-12-28 | インターナショナル・ビジネス・マシーンズ・コーポレーションInternational Business Machines Corporation | 生医学的使用のためのビタミンで機能化したゲル形成ブロック・コポリマー |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8709466B2 (en) | 2011-03-31 | 2014-04-29 | International Business Machines Corporation | Cationic polymers for antimicrobial applications and delivery of bioactive materials |
US10561146B2 (en) * | 2017-11-28 | 2020-02-18 | International Business Machines Corporation | Star polymers with enhanced antimicrobial activity in response to light |
-
2017
- 2017-11-28 US US15/824,250 patent/US10561146B2/en not_active Expired - Fee Related
-
2018
- 2018-11-09 WO PCT/IB2018/058797 patent/WO2019106459A1/en active Application Filing
- 2018-11-09 DE DE112018006058.6T patent/DE112018006058T5/de active Pending
- 2018-11-09 GB GB2003173.8A patent/GB2580240B/en active Active
- 2018-11-09 JP JP2020528011A patent/JP7266351B2/ja active Active
-
2020
- 2020-01-09 US US16/738,517 patent/US11930818B2/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007526933A (ja) * | 2003-11-21 | 2007-09-20 | ザ ユニバーシティー オブ シェフィールド | 多分岐ポリマー |
US8765098B2 (en) * | 2010-03-30 | 2014-07-01 | International Business Machines Corporation | Star polymers, methods of preparation thereof, and uses thereof |
CN103501769A (zh) * | 2011-03-18 | 2014-01-08 | 国际商业机器公司 | 星形聚合物纳米壳及其制备方法 |
JP2016522274A (ja) * | 2013-04-09 | 2016-07-28 | インターナショナル・ビジネス・マシーンズ・コーポレーションInternational Business Machines Corporation | 抗菌性のカチオン性ポリカーボネート |
JP2016222664A (ja) * | 2013-04-09 | 2016-12-28 | インターナショナル・ビジネス・マシーンズ・コーポレーションInternational Business Machines Corporation | 生医学的使用のためのビタミンで機能化したゲル形成ブロック・コポリマー |
US20140370064A1 (en) * | 2013-06-16 | 2014-12-18 | International Business Machines Corporation | Film-forming compositions of self-crosslinkable nanogel star polymers |
CN104861172A (zh) * | 2015-04-28 | 2015-08-26 | 同济大学 | 一种以卟啉为核的具有荧光效应、pH响应性和温度响应性的星型共聚物的制备方法 |
US20160338356A1 (en) * | 2015-05-19 | 2016-11-24 | International Business Machines Corporation | Antimicrobial guanidinium and thiouronium functionalized polymers |
Also Published As
Publication number | Publication date |
---|---|
JP7266351B2 (ja) | 2023-04-28 |
GB2580240A (en) | 2020-07-15 |
US20200146296A1 (en) | 2020-05-14 |
US10561146B2 (en) | 2020-02-18 |
US20190159456A1 (en) | 2019-05-30 |
GB202003173D0 (en) | 2020-04-22 |
WO2019106459A1 (en) | 2019-06-06 |
GB2580240B (en) | 2020-12-16 |
US11930818B2 (en) | 2024-03-19 |
DE112018006058T5 (de) | 2020-10-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Zhu et al. | Polycationic synergistic antibacterial agents with multiple functional components for efficient anti‐infective therapy | |
US10750746B2 (en) | Structure, synthesis, and applications for poly (phenylene) ethynylenes (PPEs) | |
Li et al. | Rational design of self-assembled cationic porphyrin-based nanoparticles for efficient photodynamic inactivation of bacteria | |
Cheng et al. | Polymer microspheres with permanent antibacterial surface from surface-initiated atom transfer radical polymerization | |
US20210259243A1 (en) | Anti-microbial polymer incorporating a quaternary ammonium group | |
Guo et al. | Enhanced photocatalytic and antibacterial activity of acridinium-grafted g-C3N4 with broad-spectrum light absorption for antimicrobial photocatalytic therapy | |
CN107596368B (zh) | 一种细菌靶向纳米粒子的制备及其抑杀细菌的应用 | |
Yang et al. | Biocompatible graphene-based nanoagent with NIR and magnetism dual-responses for effective bacterial killing and removal | |
US10584191B2 (en) | Antimicrobial star polymers with light-activated enhanced antimicrobial activity | |
JP7266351B2 (ja) | 抗菌性ポリマーおよびその生成方法、膜形成組成物、並びに、表面処理された物品の形成方法 | |
López-López et al. | Photodynamic inactivation of staphylococcus aureus biofilms using a hexanuclear molybdenum complex embedded in transparent polyhema hydrogels | |
US20150011716A1 (en) | Antipathogenic Guanidinium Copolymer | |
KR20190058754A (ko) | 박테리아 진단, 사멸기능을 갖는 유기공중합체, 탄소양자점 및 그 제조방법 | |
Sautrot-Ba et al. | Photoinduced synthesis of antibacterial hydrogel from aqueous photoinitiating system | |
JP7249718B2 (ja) | 抗菌機能を有するポリマー | |
EP3774814B1 (en) | Antimicrobial and anticancer cationic phthalocyanine compounds | |
CN111491981B (zh) | 具有抗微生物功能的亲水性聚合物 | |
Chen et al. | A dual-enhancement antibacterial strategy for hierarchically functionalized surfaces with photodynamic and antifouling performance | |
JP2022179510A (ja) | 抗菌機能を有するモノマー組成物 | |
Zainul Abid et al. | Antimicrobial efficacy of synthesized quaternary ammonium polyamidoamine dendrimers and dendritic polymer network | |
US20220132843A1 (en) | Substituted thiophene oligomers and polymers | |
RU2752860C1 (ru) | Биоразлагаемый композиционный материал с антибактериальным эффектом | |
Chen et al. | A biosynthesized near-infrared-responsive nanocomposite biomaterial for antimicrobial and antibiofilm treatment | |
Yao et al. | Quaternary Ammonium Compounds and Their Composites in Antimicrobial Applications | |
CN113583281A (zh) | 一种抗菌聚乳酸薄膜的制备方法及应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD01 | Notification of change of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7426 Effective date: 20201112 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20201113 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210122 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210423 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220125 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20220419 |
|
RD12 | Notification of acceptance of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7432 Effective date: 20220419 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20220421 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20220502 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20220420 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20220610 Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220610 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20221025 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230120 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230221 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230308 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230329 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20230329 |
|
RD14 | Notification of resignation of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7434 Effective date: 20230329 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230412 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7266351 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |