AU729662B2 - Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism - Google Patents
Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism Download PDFInfo
- Publication number
- AU729662B2 AU729662B2 AU72000/98A AU7200098A AU729662B2 AU 729662 B2 AU729662 B2 AU 729662B2 AU 72000/98 A AU72000/98 A AU 72000/98A AU 7200098 A AU7200098 A AU 7200098A AU 729662 B2 AU729662 B2 AU 729662B2
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- Australia
- Prior art keywords
- composition according
- group
- alcohol
- composition
- surfactant
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 93
- 244000005700 microbiome Species 0.000 title claims description 9
- 241000589516 Pseudomonas Species 0.000 title claims description 8
- 239000000645 desinfectant Substances 0.000 title claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 235000019441 ethanol Nutrition 0.000 claims description 23
- 239000004094 surface-active agent Substances 0.000 claims description 23
- -1 aryl alcohol Chemical compound 0.000 claims description 20
- 239000004599 antimicrobial Substances 0.000 claims description 18
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 18
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 229960003260 chlorhexidine Drugs 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 10
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 229960005323 phenoxyethanol Drugs 0.000 claims description 8
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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 7
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 claims description 7
- 229940050410 gluconate Drugs 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- OAAZUWWNSYWWHG-UHFFFAOYSA-N 1-phenoxypropan-1-ol Chemical compound CCC(O)OC1=CC=CC=C1 OAAZUWWNSYWWHG-UHFFFAOYSA-N 0.000 claims description 6
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- 150000003839 salts Chemical class 0.000 claims description 6
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims description 5
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- 238000000034 method Methods 0.000 claims description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
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- 239000000654 additive Substances 0.000 claims description 4
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- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 4
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- 235000012208 gluconic acid Nutrition 0.000 claims description 4
- 239000003752 hydrotrope Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 3
- QTDIEDOANJISNP-UHFFFAOYSA-N 2-dodecoxyethyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOCCOS(O)(=O)=O QTDIEDOANJISNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- 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 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000174 gluconic acid Substances 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 3
- HSNZZMHEPUFJNZ-RAZZTCBWSA-N (3R,4R,5S,6R)-1,3,4,5,6,7-hexahydroxyheptan-2-one Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)CO HSNZZMHEPUFJNZ-RAZZTCBWSA-N 0.000 claims description 2
- HSNZZMHEPUFJNZ-DAXDWZTDSA-N (3r,4s,5s,6r)-1,3,4,5,6,7-hexahydroxyheptan-2-one Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(=O)CO HSNZZMHEPUFJNZ-DAXDWZTDSA-N 0.000 claims description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 2
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 claims description 2
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 244000007835 Cyamopsis tetragonoloba Species 0.000 claims description 2
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 claims description 2
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 claims description 2
- HSNZZMHEPUFJNZ-QMTIVRBISA-N D-keto-manno-heptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-QMTIVRBISA-N 0.000 claims description 2
- HAIWUXASLYEWLM-UHFFFAOYSA-N D-manno-Heptulose Natural products OCC1OC(O)(CO)C(O)C(O)C1O HAIWUXASLYEWLM-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- 239000004150 EU approved colour Substances 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 claims description 2
- HSNZZMHEPUFJNZ-UHFFFAOYSA-N L-galacto-2-Heptulose Natural products OCC(O)C(O)C(O)C(O)C(=O)CO HSNZZMHEPUFJNZ-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 150000001363 alloheptuloses Chemical class 0.000 claims description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
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- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical class [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims description 2
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- 235000015165 citric acid Nutrition 0.000 claims description 2
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical class CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 claims description 2
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 2
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- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- GBVJANIKICUCCQ-UHFFFAOYSA-N C(C)(C)O.O(C1=CC=CC=C1)C(C)O Chemical compound C(C)(C)O.O(C1=CC=CC=C1)C(C)O GBVJANIKICUCCQ-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002023 Pluronic® F 87 Polymers 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- DLSFOUQNQPHSQL-UHFFFAOYSA-L disodium;cumene;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CC(C)C1=CC=CC=C1 DLSFOUQNQPHSQL-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- AJENTGJUWPNAEZ-UHFFFAOYSA-N propane-1,2-diol;propan-2-ol Chemical compound CC(C)O.CC(O)CO AJENTGJUWPNAEZ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Saccharide Compounds (AREA)
Description
WO 98/53036 PCT/AU98/00329 -1- TITLE: ALKYLPOLYGLUCOSIDES CONTAINING DISINFECTANT COMPOSITIONS ACTIVE AGAINST PSEUDOMONAS MICROORGANISM TECHNICAL FIELD This invention relates to a disinfectant cleansing composition.
BACKGROUND ART It is known that infection is spread via skin contact through the transmission of pathogenic microorganisms. Hitherto, in order to reduce the presence of such organisms it has been known to scrub the skin with a solution containing a surfactant followed by application of an antiseptic.
In recent years it has been suggested that it would be desirable to combine the washing and disinfectant actions in a single operation by providing a composition comprising both an antimicrobial agent and a surfactant. It has been found however that many antimicrobial agents such as chlorhexidine [N,N'-bis(4-chlorophenyl)- 3,12diimino 2,4,11,13-tetraazatetradecanediimidamide] digluconate and other chlorhexidine salts are incompatible with anionic surfactants, and are reduced in their antimicrobial activity by nonionic surfactants, thus requiring addition of more antimicrobial agent in order to retain sufficient biocidal activity at the amount of surfactant required for satisfactory foam formation.
In particular, US 3,855,140 assigned to Imperial Chemical Industries describes a skin cleansing composition comprising a soluble salt of chlorhexidine in combination with a polyoxyethylenepolyoxypropylene block copolymer. In order to obtain sufficient sudsing of the polymer it is necessary to use high proportions of the surfactant in amounts of the order of 20-25%. High amounts of chlorhexidine are consequently required to maintain the desired antimicrobial activity. Such high amounts are undesirable as it is known that surfactants may affect the skin adversely by defatting, and causing in combination with biocides such as chlorhexidine, irritation to the skin. Further the ingredients of the composition can be costly.
WO 98/53036 PCT/AU98/00329 -2- It would be desirable therefore to provide a composition in which the amount of antimicrobial agent and surfactant is reduced whilst maintaining sufficient antimicrobial activity and sudsing ability.
In this regard, in order to provide such a composition, WO 95/09605 teaches one to combine a phenolic disinfectant with an alkylpolyglucoside surfactant. As indicated in that patent however, such compositions although showing good biocidal activity against most microorganisms, are incapable of disinfecting surfaces contaminated by the microorganism Pseudomonas aeruginosa to which the compositions are inactive.
It is an object of the invention to substantially ameliorate the disadvantages of the prior art.
DESCRIPTION OF THE INVENTION According to a first aspect of the invention, there is provided an antiseptic cleansing composition comprising an antimicrobial agent, an effective amount of an alkylpolysaccharide surfactant, at least one alkyl alcohol and at least one aryl alcohol.
According to a second aspect of the invention there is provided a method of decontaminating surfaces contaminated with bacteria including the Pseudomonas microorganism, which method comprises contacting the surface with the disinfectant cleansing composition of the first aspect.
Typically the cleansing composition comprises an inert carrier, and optionally other additives.
The alkylpolysaccharide surfactants are also known in the art as alkylpolyglucosides, however, for the purposes of the following discussion, the surfactant will be termed an alkylpolysaccharide.
Preferably, the content of the surfactant present in the composition does not exceed 6% w/v.
Preferably the alkylpolysaccharide is an alkylpolysaccharide of the formula: WO 98/53036 PCT/AU98/00329 -3- CH2OH CH2OH OH OH V
O
(CH2)CH3
OH
OH OH m wherein n is an integer between 5 and 19, and m is an integer between 1 and 3.
In the above formula the surfactant alkyl polysaccharide shown contains glucose units, however the invention is not limited thereto and other sugar units can be substituted for one or more of the glucose units. Other sugar units which might be included in the alkylpolysaccharide include maltose, arabinose, xylose, mannose, galactose, gulose, idose, talose, allose, altrose, sucrose, fructose, sorbose, levulose, lactose, allulose, tagatose, alloheptulose, sedoheptulose, glucoheptulose, mannoheptulose, guloheptulose, idoheptulose, galactoheptulose, taloheptulose and derivatives thereof.
Suitable antimicrobial agents include chlorhexidine and its salts; dichlorophene, other chlorophenol derivatives such as p-chloro-m-xylenol, chlorophene and o-phenylphenol, 2,4,4-trichloro-2-hydroxy-diphenylether (triclosan); octenidindihydrochloride (CH 3
-(CH
2 7
-NHON-(CH
2 10
-NO-NH(CH
2 )7-CH 2 or any other salt thereof and quaternary ammonium compounds.
Suitable salts of chlorhexidine include the gluconate, isethionate, formate, acetate, glutamate, succinamate, monodiglycolate, dimethanesulfonate, lactate, diisobutyrate or the glucoheptonate salts.
Preferably the antimicrobial agent has a water solubility of at least 0.001% w/v at ambient temperature.
When the antimicrobial agent is chlorhexidine digluconate it is used in an amount preferably not exceeding 4.5% w/v. When the antimicrobial agent is 2,4,4trichloro-2-hydroxydiphenylether (triclosan) it is used in an amount preferably not exceeding 3% w/v.
WO 98/53036 PCT/AU98/00329 -4- The alkyl alcohol is preferably a lower alkyl alcohol (herein defined as an alcohol having less than 6 carbon atoms) such as ethanol, iso or n-propanol, most preferably the alkyl alcohol is isopropanol or n-propanol. The alcohol content preferably does not exceed 70% w/v. When the composition is in an aqueous carrier (for example for use in hand washing) the alcohol is desirably iso or n-propanol or a combination thereof and is preferably present in an amount of from 3 to 10% w/v, most preferably 4 to 8% w/v. When the composition is an alcoholic solution (for example for a rapid cleaning self-drying solution) the alkyl alcohol will be preferably be 55-75% w/v.
The aryl alcohol is preferably a benzylalcohol, phenylethylalcohol, phenoxyethanol, phenoxypropanol or a chlorinated derivative thereof. For application to skin, phenoxyethanol and phenoxypropanol are preferred. Preferably the aryl alcohol is present in an amount not exceeding 3% w/v.
An inert carrier can be used for example water or a lower alcohol such as ethanol.
The composition may further comprise one or more of the following integers: a solubilising agent for example propylene glycol, a hydrotrope or mixtures thereof. Suitable hydrotropes include urea, cumene sulphonate, toluene sulfonate, xylenesulphonate and the ethanolamine salts of citric and other hydroxycarboxylic acids.
a foaming agent such as an alkylaminooxide, alkylmono or diethanolamides. Examples of foaming agents are lauryl or cocodiethanolamide or monoethanolamide condensates or the lauryl or cetyl dimethylamineoxides.
viscosity modifiers such as cellulose derivatives, guar resins and carbopol resins.
preservatives such as imidazolidinyl, urea derivatives (Germabenes), methyl or propyl parabens (p-hydroxy benzoic esters).
other conventional additives such as colouring agents, fragrances, antioxidants, emolients, moisturisers, stabilising agents and thickeners such as carboxymethylcellulose.
WO 98/53036 PCT/AU98/00329 optionally, additional surfactants including amphoteric surfactants, anionic surfactants and nonionic surfactants. Suitable additional surfactants include quaternary ammonium compounds or a small amount of a high foaming anionic surfactant such as laurylethoxysulfonate, sarcosinates, sodium laurylethersulphate.
The additional ingredients are selected to avoid possible incompatibility with any of the other ingredients of the composition and especially with regard to the antimicrobial agents.
The pH of the composition is typically adjusted to pH 5 to 7, most preferably but is not limited to this pH. When chlorhexidine is used as the antimicrobial agent, a pH greater than 8 should be avoided to prevent precipitation of the chlorhexidine free base. Most organic acids compatible with the composition, such as lactic, acetic, citric and gluconic acids, preferably gluconic acid, can be used to adjust the pH.
The term "comprising" as herein used is used in an inclusive sense, that is to say in the sense of "including" or "containing". The term is not intended in an exclusive sense ("consisting of" or "composed of").
BEST MODES FOR CARRYING OUT THE INVENTION The following examples illustrate preferred embodiments of the present invention. They should not be construed as limiting.
It will also be understood by those skilled in the art that while the present invention is described herein with reference to a concentrate, such a concentrate could be diluted prior to sale (for example to 55%) or use.
EXAMPLES
Example I Comparative composition in accordance with WO 95/09605 Sodium laurylsulfate (100%) 4.67% w/v Alkylpolysaccharide (100%) 3.92% w/v Coconut Betaine (100%) 0.90% w/v Triclosan 0.49% w/v Propylene glycol 0.254% w/v Glycerine 0.254% w/v WO 98/53036 WO 9853036PCT/AU98/00329 -6- Sodium chloride Citric acid Water 0.49% w/v up to 10% w/v to 100% by volume Example 11 Cornparative Commercial Antibacterial Skin Cleanser Containing 2.0% (Trielosan) Full Composition Unknown) Example III -Comparative Composition of Commercial Antiseptic Surgical Scrub Chiorhexidine Gluconate (CHG) 4.0% w/v Nonionic Surfactant* (100%) 25.00% w/v Lauryl Dimethylamineoxide (100%) 2.60% w/v Water to 100.0% by volume (formula as per published data (Manuf. Chemist, October 1973, p. 25-27 and disclosed in US Patent 3 855 140) *polyoxyeffiylene/polyoxypropylene block copolymer PLURONIC F87 (BASF, Germany).
Examvle IV Inventive ComDosition containina Triclosan Same composition as Example 1 to which n-propanol 5.0% w/v and phenoxyethanol I% w/v have been added.
ExaMDle V Inventive Comnosition containing Triclosan Same composition as Example I to which 5.0% w/v n-propanol and I% w/v phenoxyethanol have been added and the triclosan increased to I% w/v.
WO 98/53036 WO 9853036PCT/AU98/00329 -7- Exam~le VI Inventive Composition Containing Chiorhexidine Gluconate Chiorhexidine Gluconate (CHO) Alkylpolysaccharide* (100%) Cocodiethanolaniide (100%) Propylene Glycol Isopropanol Phenoxyethanol Water *Oramix TMNS 10 55% w/v (Sepic SA, France).
2.0% w/v 4.00% w/v 2.00% w/v 2.0% w/v 8.0% w/v 2.0% w/v t .o 100% by volume Example VII Inventive Compositions Containing! Chiorhexidine Gluconate Chiorhexidine gluconate (CHG) 1.0% wlv Alkylpolysaccharide* (100%) 4.00% w/v Cocodiethanolamide (100%) 0.80% w/v Propylene glycol 2.0% w/v n-propanol 6.0% w/v Phenoxypropanol 1.0% w/v Water to 100.0% by volume *Any comrilalkylpolysaccharide ca eused such as Plantaren" 2000 (Henkel) or Atlasm G73500 (ICI).
WO 98/53036 WO 9853036PCT/AU98/00329 -8- Example VIII Inventive Composition Containing Triclosan Triclosan Alkylpolysaccharide* (100%) Sodium 2 laurylethersulfate (100%) Cocodiethanolamide (100%) Isopropanol Propylene Glycol Preservative" Phenoxyethanol Water *Oramix TMNS12 (Sepic SA, France) **Ger.mabene TM 11 0.2% w/v 1.0% W/v 4.00% w/v 0.20% wlv 2.00% w/v 8.0% w/v 10.0% w/v 1.0% w/v 2.0% wlv to 100.0% by volume Example IX Inventive ComDosition Containing Triclosan Triclosan 1.0% w/v Alkyl polysaccharide* (100%) 4.00% wlv Sodium 2 laurylethersulphate (100%) 0.25% w/v Sodium cumene sulfate (100%) 4.00% w/v Ethyl alcohol 4.0% w/v n-propanol 4.0% wlv Phenoxyethanol 1.5% w/v Water to 100% by volume *Any commercial alkylpolysaccharide can be used such as Plantaren T 2000 (Henkel) or AtlasT G73500 (ICI).
WO 98/53036 PCT/AU98/00329 -9- ExaMDle X Inventive Composition Containin! Triclosan Triclosan Alkylpolysaccharide (100%) Cocodiethanolamide (100%) Sodium xylene suiphonate (100%) Isopropanol Propylene glycol Phenoxyethanol Carboxymethyl cellulose Phenoxypropanol Water 1.00% w/v 2.75% w/v 0.80% wlv 4.00% wlv 8.0% w/v 2.0% w/vr 1.0% w/v 0.6% w/v 1.0% w/v to 100.0 by volume Examnle XI Inventive COMDosition Containing Dichlorophene Dichlorophene Alkylpolysaccharide (100%) Sodium 2 laurylethersulfate (100%) Cocodiethanolamide (100%) Isopropanol Phenoxyethanol Water 1.5% w/v 4.00% w/v 0.20% w/v 2.00% wlv 5.0% wlv 1.0% w/v by volume to make 100.0% WO 98/53036 WO 9853036PCT/AU98/00329 Example X1I Inventive Composition Containing Dichlorophene Dichiorophene 1.5% w/v Alkylpolysaccharide (100%) 4.00% w/v Sodium 2 laurylethersuiphate (100%) 0.50% w/v Cocodiethanolamide (100%) 1.00% w/v Ethanol 5.0% w/v Phenoxyethanol 1.0% w/v Water to make 100. 0% by volume adjust pH to 7.0 7.2 with triethanolamine.
Suspension tests were performed (in accordance with European Standard CEN/TC21I6/WG 1IN) in the presence of a number of organisms. The results are shown in the following table: TABLE I SUSPENSION TESTS RESULTS EXPRESSED AS: log reduction Test temperature: 23*C; Contact time: 60 seconds Neutralising Medium: Tween80 100 g/L, Lecithin 50 gIL, Histidine 1 g/L Concentration Neat Neat Neat 114CL Contact Time (secs) 60 60 60 Formulations: Comparative Example 1 0.49% w/v NG NG >2 >2 Triclosan Inventive Example IV 0.49% wlv NG NG NG NG Triclosan________ Comparative Example 11 2% w/v >2 >2 >2 >2 Triclosan Inventive Example V 1.0% wlv NG NG NG NG Triclosan Comparative Example 111 2% w/v NG 3.8 NG 3.9 Inventive Example VI 2.0% wlv NG NG -NG NG CHG Inocuium Level 2.5 x 107 2.8 x 108 1.3 x -109 1.8 x lob NG: Means NO GROWTH WO 98/53036 PCT/AU98/00329 11 Suspension tests were also conducted for the composition of Example X w/v Triclosan). The results were as follows: Microbicidal Results Suspension test 30 sec contact/con. Expressed as a Log reduction of microorganisms.
Microorganism Inoculum level Reduction S. aureus ATTC 6538 Log 6.8 5.8 E. coli ATTC 11229 Log 6.9 5.9 PS aeruginosa ATTC 15442 Log 7.0 P. mirabilia ATTC 14153 Log 6.8 Compositions according to the invention have the same or greater effectiveness with respect to biocidal activity and are less toxic, at much lower concentrations of the antimicrobial agent in comparison with conventional prior art compositions.
In preferred embodiments, the use of an alkylpolysaccharide surfactant in amounts below 6% the amount of triclosan can be successfully reduced from 1.0% to 0.5% with substantially no loss in biocidal activity. Surprisingly the amount of chlorhexidine can be reduced 4% to 2% whilst maintaining good biocidal activity and foaming properties.
Further, by use of alkylpolysaccharides in amounts as low as 2% it is possible to obtain sufficient foaming skin cleansing properties not obtainable with other conventional surfactants. Further, the known interference with the antimicrobial properties of biocides with surfactants is considerably reduced.
Further, by the inclusion of an alkyl and aryl alcohol combination, the compositions of the invention are effective against the pseudomonas microorganism.
The invention is a significant and important improvement on the art as taught in US 3,855,140 as illustrated by the fact that, while the composition of US Patent 3,855,140 showed no activity against Pseudomonas, the compositions of the present WO 98/53036 PCT/AU98/00329 -12invention are effective against Pseudomonas at concentrations containing as low as 0.49% triclosan.
Compositions according to the invention are especially suitable for skin and hand disinfection, surface disinfection, impregnation of sponges, woven and nonwoven textiles and the like.
The composition of the invention is suitable for cleansing any object. The composition of the invention is particularly suitable for cleansing hands in clinical situations and before surgery but can also be used for cleansing inanimate objects such as surgical instruments.
Claims (41)
1. An antiseptic cleansing composition effective against Pseudomonas comprising an antimicrobial agent, an effective amount of an alkylpolysaccharide surfactant, at least one alkyl alcohol and at least one aryl alcohol.
2. A cleansing composition according to claim 1 firther comprising an inert carrier.
3. A composition according to claim 1 or claim 2 wherein the content of the surfactant present in the composition does not exceed 6%.
4. A composition according to any one of the preceding claims wherein the alkylpolysaccharide is an alkylpolysaccharide of the formula: CHzOH OH 0- OH -O(CH2)nCH3 OH OH OH m wherein n is an integer between 5 and 19, and m is an integer between 1 and 3. A composition according to any one of claims 1 to 3 wherein the surfactant alkyl polysaccharide contains one or more sugar units selected from the group consisting of maltose, arabinose, xylose, mannose, galactose, gulose, idose, talose, allose, altrose, sucrose, fructose, sorbose, levulose, lactose, allulose, tagatose, alloheptulose, sedoheptulose, glucoheptulose, mannoheptulose, guloheptulose, idoheptulose, galactoheptulose, taloheptulose and derivatives thereof.
6. A composition according to any one of the preceding claims wherein the antimicrobial agent is selected from the group consisting of chlorhexidine, chlorhexidine salt, chlorophenol derivative, octenidindihydrochloride (CH 3 -(CH 2 7 NHON-(CH 2 0 -NO-NH(CH 2 )7-CH 2 or any other salt thereof, and quaternary ammonium compounds.
7. A composition according to claim 6 wherein the salt of chlorhexidine is selected from the group consisting of gluconate, isethionate, formate, acetate, AMENDED SHEET (Article 34) (IPEA/AtJ) WO 98/53036 PCT/AU98/00329 -14- glutamate, succinamate, monodiglycolate, dimethanesulfonate, lactate, diisobutyrate or the glucoheptonate salts.
8. A composition according to any one of claims 1 to 7 wherein the antimicrobial agent is chlorhexidine digluconate.
9. A composition according to claim 8 wherein the chlorhexidine does not exceed w/v. A composition according to claim 6 wherein the chlorophenol derivative is selected from the group consisting of dichlorophene, p-chloro-m-xylenol, chlorophene, o-phenylphenol, and 2,4,4-trichloro-2-hydroxy-diphenylether.
11. A composition according to claim 10 wherein the antimicrobial agent is 2,4,4- trichloro-2-hydroxydiphenylether.
12. A composition according to claim 11 wherein the 2,4,4-trichloro-2- hydroxydiphenylether does not exceed 3% w/v.
13. A composition according to any one of the preceding claims wherein the antimicrobial agent has a water solubility of at least 0.001% w/v at ambient temperature.
14. A composition according to any one of the preceding claims wherein the alkyl alcohol is a lower alkyl alcohol. A composition according to claim 14 wherein the lower alkyl alcohol is ethanol, isopropanol or n-propanol.
16. A composition according to claim 15 wherein the lower alkyl alcohol is isopropanol or n-propanol or a combination thereof.
17. A composition according to any one of the preceding claims wherein the alcohol content does not exceed 70% w/v.
18. A composition according to any one of the preceding claims wherein the alcohol content is between 55-70% w/v.
19. A composition according to claim 17 wherein the alcohol is present in an amount of from 3 to 10% w/v. A composition according to claim 19 wherein the alcohol is present in an amount of from 4 to 8% w/v. WO 98/53036 PCT/AU98/00329
21. A composition according to any one of the preceding claims wherein the aryl alcohol is selected from the group consisting of a benzylalcohol, a phenylethylalcohol, a phenoxyethanol, a phenoxypropanol or a chlorinated derivative thereof.
22. A composition according to claim 21 wherein the aryl alcohol is selected from the group consisting of phenoxyethanol and phenoxypropanol. 23 A composition according to any one of the preceding claims wherein the aryl alcohol does not exceed 3% w/v.
24. A composition according to any one of the preceding claims further including an inert carrier.
25. A composition according to claim 24 wherein the inert carrier is water
26. A composition according to claim 24 wherein the inert carrier is a lower alcohol.
27. A composition according to claim 26 wherein the inert carrier is a ethanol.
28. A composition according to any one of the preceding claims further including one or more of the integers selected from the group consisting of a solubilising agent a foaming agent one or more viscosity modifiers preservatives other conventional additives additional surfactants
29. A composition according to claim 28 wherein the solubilising agent is propylene glycol, a hydrotrope or mixtures thereof. A composition according to claim 29 wherein the hydrotrope is selected from the group consisting of urea, cumenesulfonate, toluenesulfonate, xylenesulphonate and the ethanolamine salts of citric and other hydroxycarboxylic acids.
31. A composition according to any one of claims 28 to 30 wherein the foaming agent is an alkylaminooxide, alkylmono or diethanolamide.
32. A composition according to claim 31 wherein the foaming agent is selected from the group consisting of lauryl condensates, cocodiethanolamide condensates, WO 98/53036 PCT/AU98/00329 -16- monoethanolamide condensates, lauryl dimethylamine oxides and cetyl dimethylamine oxides.
33. A composition according to any one of claims 28 to 32 wherein the viscosity modifier is selected from the group consisting of cellulose derivatives, guar resins and carbopol resins.
34. A composition according to any one of claims 28 to 33 wherein the preservative is selected from the group consisting of imidazolidinyl derivatives, urea derivatives (Germabenes), methyl parabens (p-hydroxy benzoic esters) or propyl parabens (p-hydroxy benzoic esters).
35. A composition according to any one of claims 28 to 34 wherein the conventional additives are selected from the group consisting of colouring agents, fragrances, antioxidants, emollients, stabilising agents and thickeners
36. A composition according to claim 35 wherein the thickener is carboxymethylcellulose.
37. A composition according to any one of claims 28 to 36 wherein the additional surfactant is selected from the group consisting of amphoteric surfactants, anionic surfactants and ionic surfactants.
38. A composition according to claim 37 wherein the additional surfactants include a quaternary ammonium compound or a high foaming anionic surfactant.
39. A composition according to claim 38 wherein high foaming anionic surfactant is selected from the group consisting of laurylethoxysulfonate, a sarcosinate and sodium 2 laurylethersulphate. A composition according to any one of claims 28 to 39 wherein additional ingredients are selected to avoid possible incompatibility with any of the other ingredients of the composition and especially with regard to the antimicrobial agent.
41. A composition according to any one of the preceding claims wherein the pH is 8 or less.
42. A composition according to any one of the preceding claims wherein the pH is in the range 5 to 7.
43. A composition according to claim 40 wherein the pH is SUBSTITUTE SHEET (RULE 26) WO 98/53036 PCT/AU98/00329 -17-
44. A composition according to any one of claims 1 to 40 wherein the pH is controlled to avoid precipitation of ingredients. A composition according to any one of the preceding claims wherein the pH is adjusted by an organic acid.
46. A composition according to claim 45 wherein organic acid is selected from the group consisting of lactic acid, acetic acid, citric acid and gluconic acid.
47. A composition according to claim 46 wherein the organic acid is gluconic acid.
48. A method of decontaminating surfaces contaminated with bacteria including the pseudomonas microorganism, which method comprises contacting the surface with a disinfectant cleansing composition according to any one of the preceding claims.
49. A disinfectant cleansing composition substantially as herein described with reference to any one of the examples. A method of decontaminating surfaces substantially as herein described with reference to any one of the examples. SUBSTITUTE SHEET (RULE 26)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU72000/98A AU729662C (en) | 1997-05-20 | 1998-05-07 | Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPO6909A AUPO690997A0 (en) | 1997-05-20 | 1997-05-20 | Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism |
| AUPO6909 | 1997-05-20 | ||
| PCT/AU1998/000329 WO1998053036A1 (en) | 1997-05-20 | 1998-05-07 | Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism |
| AU72000/98A AU729662C (en) | 1997-05-20 | 1998-05-07 | Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU7200098A AU7200098A (en) | 1998-12-11 |
| AU729662B2 true AU729662B2 (en) | 2001-02-08 |
| AU729662C AU729662C (en) | 2004-06-17 |
Family
ID=25636833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU72000/98A Expired AU729662C (en) | 1997-05-20 | 1998-05-07 | Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU729662C (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992013055A1 (en) * | 1991-01-29 | 1992-08-06 | Henkel Kommanditgesellschaft Auf Aktien | Liquid washing agents |
| WO1995009605A1 (en) * | 1993-10-06 | 1995-04-13 | Henkel Corporation | Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants |
| WO1997048377A1 (en) * | 1996-06-15 | 1997-12-24 | Smithkline Beecham Plc | Skin wash compositions comprising triclocarban and surfactants |
-
1998
- 1998-05-07 AU AU72000/98A patent/AU729662C/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992013055A1 (en) * | 1991-01-29 | 1992-08-06 | Henkel Kommanditgesellschaft Auf Aktien | Liquid washing agents |
| WO1995009605A1 (en) * | 1993-10-06 | 1995-04-13 | Henkel Corporation | Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants |
| WO1997048377A1 (en) * | 1996-06-15 | 1997-12-24 | Smithkline Beecham Plc | Skin wash compositions comprising triclocarban and surfactants |
Also Published As
| Publication number | Publication date |
|---|---|
| AU729662C (en) | 2004-06-17 |
| AU7200098A (en) | 1998-12-11 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| DA2 | Applications for amendment section 104 |
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| DA3 | Amendments made section 104 |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |