EP2563481A2 - Mikrobiologisch stabile anwendungsfreundliche w/o-zubereitungen - Google Patents
Mikrobiologisch stabile anwendungsfreundliche w/o-zubereitungenInfo
- Publication number
- EP2563481A2 EP2563481A2 EP10759574A EP10759574A EP2563481A2 EP 2563481 A2 EP2563481 A2 EP 2563481A2 EP 10759574 A EP10759574 A EP 10759574A EP 10759574 A EP10759574 A EP 10759574A EP 2563481 A2 EP2563481 A2 EP 2563481A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- preparations
- methylisothiazolinone
- benzethonium chloride
- cosmetic
- viscosity
- 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.)
- Ceased
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 41
- 239000002537 cosmetic Substances 0.000 claims abstract description 23
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims abstract description 22
- 229960001950 benzethonium chloride Drugs 0.000 claims abstract description 22
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims abstract description 20
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims abstract description 20
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940081510 piroctone olamine Drugs 0.000 claims abstract description 13
- ROLNTYULJXVURI-SFHVURJKSA-N (2S)-5-(diaminomethylideneamino)-2-(3-oxotetradecylamino)pentanoic acid Chemical compound CCCCCCCCCCCC(=O)CCN[C@@H](CCCN=C(N)N)C(=O)O ROLNTYULJXVURI-SFHVURJKSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 abstract description 18
- -1 lauroyl ethyl Chemical group 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003755 preservative agent Substances 0.000 description 11
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 229940008099 dimethicone Drugs 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 229960005323 phenoxyethanol Drugs 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 230000000813 microbial effect Effects 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- OIQJEQLSYJSNDS-UHFFFAOYSA-N piroctone Chemical compound CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O OIQJEQLSYJSNDS-UHFFFAOYSA-N 0.000 description 6
- 239000007762 w/o emulsion Substances 0.000 description 6
- 241000191963 Staphylococcus epidermidis Species 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229950001046 piroctone Drugs 0.000 description 5
- 229920002545 silicone oil Polymers 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920006007 hydrogenated polyisobutylene Polymers 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 229940101267 panthenol Drugs 0.000 description 3
- 235000020957 pantothenol Nutrition 0.000 description 3
- 239000011619 pantothenol Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 239000004368 Modified starch Substances 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 2
- 229940063655 aluminum stearate Drugs 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229940086555 cyclomethicone Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- PKPOVTYZGGYDIJ-UHFFFAOYSA-N dioctyl carbonate Chemical compound CCCCCCCCOC(=O)OCCCCCCCC PKPOVTYZGGYDIJ-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- CUBZMGWLVMQKNE-LMOVPXPDSA-N ethyl (2s)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride Chemical compound Cl.CCCCCCCCCCCC(=O)N[C@H](C(=O)OCC)CCCNC(N)=N CUBZMGWLVMQKNE-LMOVPXPDSA-N 0.000 description 2
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 2
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 235000019426 modified starch Nutrition 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- SARNODYRNJVRJK-SFHVURJKSA-N (2s)-5-(diaminomethylideneamino)-2-(tetradecylamino)pentanoic acid Chemical compound CCCCCCCCCCCCCCN[C@H](C(O)=O)CCCNC(N)=N SARNODYRNJVRJK-SFHVURJKSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
- SDSHANKXUIMGJQ-UHFFFAOYSA-N 3-ethyl-1,2-thiazol-4-one Chemical compound CCC1=NSCC1=O SDSHANKXUIMGJQ-UHFFFAOYSA-N 0.000 description 1
- DLICJXPMMTZITN-UHFFFAOYSA-N 3-methyl-1,2-thiazol-4-one Chemical compound CC1=NSCC1=O DLICJXPMMTZITN-UHFFFAOYSA-N 0.000 description 1
- AJBZENLMTKDAEK-UHFFFAOYSA-N 3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-4,9-diol Chemical compound CC12CCC(O)C(C)(C)C1CCC(C1(C)CC3O)(C)C2CCC1C1C3(C)CCC1C(=C)C AJBZENLMTKDAEK-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 235000003880 Calendula Nutrition 0.000 description 1
- 240000001432 Calendula officinalis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- XPJVKCRENWUEJH-UHFFFAOYSA-N Isobutylparaben Chemical compound CC(C)COC(=O)C1=CC=C(O)C=C1 XPJVKCRENWUEJH-UHFFFAOYSA-N 0.000 description 1
- CMHMMKSPYOOVGI-UHFFFAOYSA-N Isopropylparaben Chemical compound CC(C)OC(=O)C1=CC=C(O)C=C1 CMHMMKSPYOOVGI-UHFFFAOYSA-N 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 241001134446 Niveas Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241001147691 Staphylococcus saprophyticus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003214 anti-biofilm Effects 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000037358 bacterial metabolism Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000008384 inner phase Substances 0.000 description 1
- 229940113094 isopropylparaben Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229950004864 olamine Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940031709 peg-30-dipolyhydroxystearate Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- GJLNWLVPAHNBQN-UHFFFAOYSA-N phenyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=CC=C1 GJLNWLVPAHNBQN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229940048845 polyglyceryl-3 diisostearate Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000001993 wax Substances 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
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/007—Preparations for dry skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
Definitions
- the invention includes cosmetic or dermatological preparations in the form of water in oil emulsions with benzethonium chloride, ethylisothiazolinone, Piroctone
- Water in oil Emulsions have various advantages for cosmetics: For example, the water resistance of sunscreen formulation is much better than that of oil in water emulsions. Another advantage is that with water in oil it is possible to delay the release of a dissolved in the inner phase of the two-phase system hydrophilic drug, which may be galenic and in the mechanism of action of an active ingredient of advantage.
- water-in-oil emulsions are very susceptible to various raw materials customary in cosmetics. These include, in particular, salts, alcohols, perfume oils, active ingredients and preservatives.
- salts include, in particular, salts, alcohols, perfume oils, active ingredients and preservatives.
- the addition of these substances often leads to an undesirable change in the theological profile.
- the viscosity can rise, fall or remain the same when the yield point is shifted. This change can happen immediately after intake of these substances or over time, up to several weeks later.
- a possible change in the theological profile is that the viscosity decreases and thereby falls within a range that no longer allows a user-friendly application. That The product literally runs through your fingers. Such a low viscosity can then no longer be easily corrected by other additives.
- parabens especially 4-hydroxybenzoic acid and its esters, methylparaben, ethylparaben,, propylparaben, isopropylparaben, butylparaben, isobutylparaben, phenylparaben.
- Phenoxetol ® known for the preservation of cosmetic products.
- auxiliaries for microbial stabilization are benzethonium chloride, lauroylethylarginate, octopirox and methylisothiazolinone.
- Grapefruit seed extracts can be used in cleaning agents but also in medicines (spermicides, lozenges against angina). Grapefruit seed extracts can be used in cleaning agents but also in medicines (spermicides, lozenges against angina). Grapefruit seed extracts can be used in cleaning agents but also in medicines (spermicides, lozenges against angina). Grapefruit seed extracts can be used in cleaning agents but also in medicines (spermicides, lozenges against angina). Grapefruit seed extracts can
- benzethonium chloride is known, as described, for example, in WO 2007015243 A1, WO 2004034964 A1, EP 1310234 A1, WO 2002008377 A1.
- Aminate-G (INCI: Glycerol and ethyl lauroyl arginate HCl) shows a large antimicrobial spectrum and is tested as an additive in foods FDA (see eg WO
- Piroctone Olamine 1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2 (1H) -pyridone, also referred to as octopirox, is an antimicrobial used as a preservative and has e.g. B. is used in shampoos as anti-dandruff. Octopirox is good
- Methylisothiazolinone (2-methyl-2 / - / - isothiazol-3-one (MIT)) is a class of compounds with high microbicidal activity, which is mainly used for the preservation of technical products and only a few cosmetic products.
- methylisothiazolinone is described, for example, in US Pat. No. 6,511,673 or EP 1,488,699 A1 in combination with parabens or phenoxyethanol.
- the invention includes benzethonium chloride, methylisothiazolinone, piroctone olamine and / or lauroylethylarginate in cosmetic or dermatological W / O preparations.
- the preparations do not comprise any further preservatives,
- the proportion of benzethonium chloride, methylisothiazolinone, piroctone olamine and / or lauroylethylarginate is preferably in the range of 0.01 to 5 wt.%, In particular in the range of 0.1 to 2 wt.%, Based on the total mass of the preparation to choose.
- Benzethonium chloride, methylisothiazolinone, Piroctone olamine and / or Lauroylethylarginat be included.
- An emulsion is a system of two immiscible ones
- Liquids wherein one liquid is finely dispersed in the other.
- the system must be stirred or shaken.
- An emulsifier prevents the
- the oil phase is continuous, the water phase is distributed in small droplets therein (example: butter). If the oil phase consists essentially of silicone oil, it is called a water in silicone emulsion (W / Si).
- the W / O preparations according to the invention also comprise water in silicone emulsions.
- the consistency of the cream preparations comprising variants A and B was measured at different time intervals using a consistency determination device according to Fligge (according to DE 29 09 087).
- Preparation B according to the invention leads to viscosity-stable preparations with a constant course of viscosity, which deviates at most by 18% from the initial value at 25 ° C.
- benzethonium chloride, methylisothiazolinone, piroctone olamine and / or lauroylethylarginate in paraben- and / or phenoxyethanol-free cosmetic or dermatological W / O preparations used to improve the stability of the viscosity of the preparation.
- viscosity-stabilizing means that the viscosity of the preparations changes by a maximum of 18% at 25 ° C. within 4 weeks.
- the viscosity of the invention is determined using a Viscotester VT-02, the company Haake at 25 ° C with the aid of the rotating body 1 or 2 and reading the scale 1 and 2 respectively
- the improved stability is accompanied by an improved shelf life of the preparations.
- the preparations according to the invention are preferably paraben and / or
- Phenoxyethanolza still have sufficient microbial stability.
- Microplate scale examined. The measurement results of the active substances investigated are related to the positive control (PK1). Neither Ethylparaben nor Methylparaben showed efficacy. In comparison, benzethonium chloride,
- Methylisothiazolinone Piroctone Olamine and Lauroylethylarginat a very good biofilm-inhibiting activity.
- benzethonium chloride for benzethonium chloride
- Preservatives are usually among the bactericidal agents.
- the anti-biofilm agents do not directly interfere with the bacterial metabolism, but merely prevent or dissolve the formation of the bacteria-protecting biofilm.
- Staphylococcus epidermidis (syn., Staphylococcus albus, Micrococcus epidermidis, Staphylococcus saprophyticus) is a gram-positive, plasma-coagulase-negative, saprophagic bacterium that colonizes human skin and mucous membranes. Furthermore, it is found on food and also settles on polymeric surfaces (e.g., packaging)
- S. epidermidis has a wide spectrum of antibiotic resistance. This is especially true against penicillin and methicillin. The proportion of resistant strains is now 70%.
- preparations according to the invention are preferably paraben and / or
- Phenoxyethanolza still have sufficient microbial stability.
- Paraben-free or phenoxyethanol-free means that the proportion of parabens and / or phenoxyethanol is less than 1% by weight, based on the total mass of the preparation.
- the proportion of parabens and phenoxyethanol is 0% by weight.
- the cosmetic preparations according to the invention may further cosmetic
- Excipients and other active ingredients such as are commonly used in such preparations, for.
- substances for preventing the foaming, dyes and color pigments, thickeners, moisturizing and / or moisturizing substances fats, oils, waxes or other conventional constituents of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives if the additive does not impair the required properties with regard to the type of emulsion as well as microbiological stability and skin tolerance.
- the numbers are parts by weight based on the total mass of the preparation.
- PEG-30 dipolyhydroxystearate - 0.5 0.25 - 3.0
- cyclic silicone oil 12.5 15 22.0 20.0 15.5 linear silicone oil (dimethicone) 5.0 13.0 5.0 12.0 15.0 hydrogenated polyisobutene 0.5 0.75 1.0 2 , 0 0.25
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Dermatology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010013275A DE102010013275A1 (de) | 2010-03-29 | 2010-03-29 | Mikrobiologisch stabile anwendungsfreundliche W/O-Zubereitungen |
| PCT/EP2010/005376 WO2011124242A2 (de) | 2010-03-29 | 2010-09-02 | Mikrobiologisch stabile anwendungsfreundliche w/o-zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2563481A2 true EP2563481A2 (de) | 2013-03-06 |
Family
ID=44586109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP10759574A Ceased EP2563481A2 (de) | 2010-03-29 | 2010-09-02 | Mikrobiologisch stabile anwendungsfreundliche w/o-zubereitungen |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP2563481A2 (de) |
| DE (1) | DE102010013275A1 (de) |
| WO (1) | WO2011124242A2 (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010055768A1 (de) * | 2010-12-23 | 2012-06-28 | Beiersdorf Ag | Wirkstoffkombinationen aus Glucosylglyceriden und einem oder mehreren Konservierungsmitteln |
| DE102012219641A1 (de) * | 2012-10-26 | 2014-04-30 | Beiersdorf Ag | Zweiphasen Produkt |
| FR3032615B1 (fr) * | 2015-02-12 | 2018-05-25 | Laboratoire De Dermo-Cosmetique Animale | Composition antimicrobienne pour animaux |
| DE102015223829A1 (de) * | 2015-12-01 | 2017-06-01 | Henkel Ag & Co. Kgaa | Leistungsstarke Haarbehandlungsmittel mit Anti-Auswasch-Effekt |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1352420A (en) * | 1971-06-18 | 1974-05-08 | Ajinomoto Kk | Arginine derivatives their production and their use |
| DE2909087C2 (de) | 1979-03-08 | 1982-04-29 | Beiersdorf Ag, 2000 Hamburg | Vorrichtung zum Ermitteln der Fließeigenschaften zähfließender oder pastöser Stoffe und Anwendung der Vorrichtung zum Ermitteln der Zügigkeit |
| IE60024B1 (en) * | 1987-02-03 | 1994-05-18 | Stiefel Laboratories Ltd | Microemulsions |
| ATE177318T1 (de) * | 1990-10-04 | 1999-03-15 | Gillette Co | Kosmetische technologie |
| FR2685638A1 (fr) * | 1991-12-31 | 1993-07-02 | Biorga Sa Laboratoires | Compositions pour l'usage cosmetique et/ou dermatologique, comprenant une association de pyrithione zinc, de piroctone olamine, et d'un derive de collagene et d'acide gras. |
| WO2001021138A1 (en) * | 1999-09-22 | 2001-03-29 | First Scientific, Inc. | Antimicrobial topical composition and methods |
| US6511673B1 (en) | 2000-05-10 | 2003-01-28 | Rohm And Haas Company | Microbicidal composition |
| WO2002008377A1 (en) | 2000-07-21 | 2002-01-31 | Novozymes A/S | Antimicrobial compositions |
| ES2378300T3 (es) * | 2001-08-09 | 2012-04-11 | Laboratorios Miret, S.A. | Uso de tensioactivos catiónicos en preparaciones cosméticas |
| CA2455983C (en) * | 2001-08-09 | 2010-06-01 | Laboratorios Miret, S.A. | Preservative systems and their use in cosmetic preparations |
| US6652842B2 (en) | 2001-11-13 | 2003-11-25 | Noville, Inc. | Deodorant compositions comprising diglycerol |
| AU2003216034A1 (en) * | 2002-01-21 | 2003-07-30 | Slovakofarma A.S. | Dermatological topical compositions and a process for the preparation thereof |
| EP1621076B1 (de) | 2002-01-31 | 2013-05-22 | Rohm And Haas Company | Synergistische mikrobizide Kombination |
| WO2004034964A2 (en) | 2002-05-20 | 2004-04-29 | Kling William O | Skin cleanser compositions and methods of use |
| US20060051430A1 (en) * | 2004-09-07 | 2006-03-09 | Arata Andrew B | Silver dihydrogen citrate compositions |
| EP2431089A1 (de) | 2005-08-02 | 2012-03-21 | Sol-Gel Technologies Ltd. | Metalloxidbeschichtung von wasserunlöslichen Inhaltsstoffen |
| US9555167B2 (en) | 2006-12-11 | 2017-01-31 | 3M Innovative Properties Company | Biocompatible antimicrobial compositions |
| DE102007045242A1 (de) * | 2007-04-20 | 2008-10-23 | Beiersdorf Ag | Benzaldehyde in kosmetischen oder dermatologischen Zubereitungen |
| EP2153813A1 (de) * | 2008-08-15 | 2010-02-17 | Lonza, Inc. | Synergistische Konservierungsmischungen |
| DE202008011653U1 (de) * | 2008-09-02 | 2009-01-29 | Medicos Kosmetik Gmbh & Co. Kg | Wirkstoffkombination, kosmetische oder pharmazeutische Zubereitung und Verpackungseinheit |
| DE102009022444A1 (de) * | 2009-05-23 | 2010-01-07 | Clariant International Limited | Zusammensetzung enthaltend Sorbitanmonocaprylat und antimikrobielle Wirkstoffe |
| DE102010007958A1 (de) * | 2010-02-12 | 2011-08-18 | Beiersdorf AG, 20253 | Wirkstoffkombinationen aus Acylarginaten und quaternären Ammoniumverbindungen |
-
2010
- 2010-03-29 DE DE102010013275A patent/DE102010013275A1/de not_active Ceased
- 2010-09-02 EP EP10759574A patent/EP2563481A2/de not_active Ceased
- 2010-09-02 WO PCT/EP2010/005376 patent/WO2011124242A2/de not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2011124242A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011124242A3 (de) | 2013-01-31 |
| WO2011124242A2 (de) | 2011-10-13 |
| DE102010013275A1 (de) | 2011-09-29 |
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