DE1287259B - Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen Mitteln - Google Patents
Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen MittelnInfo
- Publication number
- DE1287259B DE1287259B DEH62546A DEH0062546A DE1287259B DE 1287259 B DE1287259 B DE 1287259B DE H62546 A DEH62546 A DE H62546A DE H0062546 A DEH0062546 A DE H0062546A DE 1287259 B DE1287259 B DE 1287259B
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- bromo
- bis
- trichlorophenol
- weight
- 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
- 239000003795 chemical substances by application Substances 0.000 title claims description 20
- -1 nitro alcohols Chemical class 0.000 title claims description 17
- 239000004599 antimicrobial Substances 0.000 title claims description 7
- 230000000845 anti-microbial effect Effects 0.000 claims description 13
- 150000002989 phenols Chemical class 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 9
- 230000003389 potentiating effect Effects 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000000645 desinfectant Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 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 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000003868 ammonium compounds Chemical class 0.000 claims description 3
- 230000002421 anti-septic effect Effects 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims 4
- 244000060011 Cocos nucifera Species 0.000 claims 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 150000004665 fatty acids Chemical class 0.000 claims 3
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 claims 2
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- 239000002781 deodorant agent Substances 0.000 claims 2
- 230000000249 desinfective effect Effects 0.000 claims 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 2
- 239000002304 perfume Substances 0.000 claims 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- OTGQIQQTPXJQRG-UHFFFAOYSA-N N-(octadecanoyl)ethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCO OTGQIQQTPXJQRG-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 1
- 239000004203 carnauba wax Substances 0.000 claims 1
- 235000013869 carnauba wax Nutrition 0.000 claims 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 claims 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims 1
- 230000002070 germicidal effect Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 239000008262 pumice Substances 0.000 claims 1
- 239000010453 quartz Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 12
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 11
- 238000004659 sterilization and disinfection Methods 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000003899 bactericide agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical group OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003739 xylenols Chemical class 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- UWEZBKLLMKVIPI-UHFFFAOYSA-N 2,5-dinitrophenol Chemical group OC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O UWEZBKLLMKVIPI-UHFFFAOYSA-N 0.000 description 1
- NKICVYRTQZNBQQ-UHFFFAOYSA-N 2-(2-octyl-4,5-dihydro-1h-imidazol-3-ium-3-yl)ethanol;chloride Chemical compound [Cl-].CCCCCCCCC1=NCC[NH+]1CCO NKICVYRTQZNBQQ-UHFFFAOYSA-N 0.000 description 1
- WPMBXQJYQZTSGS-UHFFFAOYSA-N 2-benzyl-4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1CC1=CC=CC=C1 WPMBXQJYQZTSGS-UHFFFAOYSA-N 0.000 description 1
- OADSZWXMXIWZSQ-UHFFFAOYSA-N 2-bromo-2-nitropropane Chemical compound CC(C)(Br)[N+]([O-])=O OADSZWXMXIWZSQ-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- KIPMDPDAFINLIV-UHFFFAOYSA-N 2-nitroethanol Chemical compound OCC[N+]([O-])=O KIPMDPDAFINLIV-UHFFFAOYSA-N 0.000 description 1
- UPXZHXVOMCGZDS-UHFFFAOYSA-N 2-phenylbenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1C1=CC=CC=C1 UPXZHXVOMCGZDS-UHFFFAOYSA-N 0.000 description 1
- MDNVJHRZPNYBNW-UHFFFAOYSA-N 2-tridecylpyridin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCCCCCCC1=CC=CC=[NH+]1.CCCCCCCCCCCCCC1=CC=CC=[NH+]1 MDNVJHRZPNYBNW-UHFFFAOYSA-N 0.000 description 1
- VWJQHPUEALFONG-UHFFFAOYSA-N 3-nitrobutane-1,2,2-triol Chemical compound [N+](=O)([O-])C(C(O)(O)CO)C VWJQHPUEALFONG-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- QRYSWXFQLFLJTC-UHFFFAOYSA-N 616-82-0 Chemical compound OC(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 QRYSWXFQLFLJTC-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RIWOUIXFHKHFIM-UHFFFAOYSA-N CC(CC(C=CC=C1)=C1Cl)([N+]([O-])=O)Br Chemical compound CC(CC(C=CC=C1)=C1Cl)([N+]([O-])=O)Br RIWOUIXFHKHFIM-UHFFFAOYSA-N 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- OTLNYGUBCWMBRR-UHFFFAOYSA-N O=C(C(C(OCl)=C(C(Br)=C1Br)Br)=C1Cl)N(C(C=CC=C1Cl)=C1Cl)Cl Chemical compound O=C(C(C(OCl)=C(C(Br)=C1Br)Br)=C1Cl)N(C(C=CC=C1Cl)=C1Cl)Cl OTLNYGUBCWMBRR-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 102100021941 Sorcin Human genes 0.000 description 1
- 101710089292 Sorcin Proteins 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- FADYGXGJTNYCHZ-UHFFFAOYSA-M benzyl-dodecyl-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 FADYGXGJTNYCHZ-UHFFFAOYSA-M 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940073469 dimethyldodecylbenzylammonium Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229960004068 hexachlorophene Drugs 0.000 description 1
- VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical compound [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003158 microbiostatic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- IBSSBDSZRZSTHK-UHFFFAOYSA-N n-methyltetradecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCC[NH2+]C IBSSBDSZRZSTHK-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 238000013166 platelet test Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pest Control & Pesticides (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH62546A DE1287259B (de) | 1967-04-26 | 1967-04-26 | Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen Mitteln |
| US709834A US3592893A (en) | 1967-04-26 | 1968-03-01 | Nitro alcohols in synergistic antimicrobic compositions |
| NL6803249A NL6803249A (en:Method) | 1967-04-26 | 1968-03-07 | |
| GB01080/68A GB1217572A (en) | 1967-04-26 | 1968-03-07 | Improvements in anti-microbic agents |
| FR1565749D FR1565749A (en:Method) | 1967-04-26 | 1968-03-29 | |
| CH606868A CH472893A (de) | 1967-04-26 | 1968-04-24 | Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen Mitteln |
| BE714185D BE714185A (en:Method) | 1967-04-26 | 1968-04-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH62546A DE1287259B (de) | 1967-04-26 | 1967-04-26 | Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen Mitteln |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1287259B true DE1287259B (de) | 1969-01-16 |
| DE1287259C2 DE1287259C2 (en:Method) | 1969-09-18 |
Family
ID=7161907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH62546A Granted DE1287259B (de) | 1967-04-26 | 1967-04-26 | Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen Mitteln |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3592893A (en:Method) |
| BE (1) | BE714185A (en:Method) |
| CH (1) | CH472893A (en:Method) |
| DE (1) | DE1287259B (en:Method) |
| FR (1) | FR1565749A (en:Method) |
| GB (1) | GB1217572A (en:Method) |
| NL (1) | NL6803249A (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001062081A3 (de) * | 2000-02-24 | 2002-06-20 | Bayer Ag | Mikrobizide mittel |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2417987A1 (fr) * | 1978-02-24 | 1979-09-21 | Azote & Prod Chim | Procede de traitement bactericide et bacteriostatique d'un milieu pollue |
| US5055493A (en) * | 1988-09-30 | 1991-10-08 | Union Carbide Chemicals And Plastics Technology Corporation | Antimicrobial composition and method of use in oil well flooding |
| JP4637464B2 (ja) * | 2003-07-01 | 2011-02-23 | Ｊｓｒ株式会社 | 化学機械研磨用水系分散体 |
| EP2687091A1 (en) * | 2009-09-25 | 2014-01-22 | Dow Global Technologies LLC | Synergistic antimicrobial composition containing ortho-phenylphenol and hexahydro-1,3,5-tris(2-hydroxyethyl)-2-triazine |
| AU2013231143B2 (en) * | 2009-09-25 | 2016-05-19 | Dow Global Technologies Llc | Synergistic antimicrobial composition |
-
1967
- 1967-04-26 DE DEH62546A patent/DE1287259B/de active Granted
-
1968
- 1968-03-01 US US709834A patent/US3592893A/en not_active Expired - Lifetime
- 1968-03-07 GB GB01080/68A patent/GB1217572A/en not_active Expired
- 1968-03-07 NL NL6803249A patent/NL6803249A/xx unknown
- 1968-03-29 FR FR1565749D patent/FR1565749A/fr not_active Expired
- 1968-04-24 CH CH606868A patent/CH472893A/de not_active IP Right Cessation
- 1968-04-25 BE BE714185D patent/BE714185A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001062081A3 (de) * | 2000-02-24 | 2002-06-20 | Bayer Ag | Mikrobizide mittel |
| EP1502505A3 (de) * | 2000-02-24 | 2005-02-16 | Bayer Chemicals AG | Mikrobizide Mittel |
| EP1502506A3 (de) * | 2000-02-24 | 2005-02-16 | Bayer Chemicals AG | Mikrobizide Mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1217572A (en) | 1970-12-31 |
| US3592893A (en) | 1971-07-13 |
| NL6803249A (en:Method) | 1968-10-28 |
| DE1287259C2 (en:Method) | 1969-09-18 |
| BE714185A (en:Method) | 1968-10-25 |
| CH472893A (de) | 1969-05-31 |
| FR1565749A (en:Method) | 1969-05-02 |
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