LU87338A1 - Utilisation de derives d'indole pour la teinture de matieres keratiniques,compositions tinctoriales,composes nouveaux et procede de teinture - Google Patents
Utilisation de derives d'indole pour la teinture de matieres keratiniques,compositions tinctoriales,composes nouveaux et procede de teinture Download PDFInfo
- Publication number
- LU87338A1 LU87338A1 LU87338A LU87338A LU87338A1 LU 87338 A1 LU87338 A1 LU 87338A1 LU 87338 A LU87338 A LU 87338A LU 87338 A LU87338 A LU 87338A LU 87338 A1 LU87338 A1 LU 87338A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- composition
- indole
- hydroxy
- group
- dyeing
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 154
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 60
- 238000004043 dyeing Methods 0.000 title claims description 48
- 238000000034 method Methods 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 title claims description 42
- 239000000463 material Substances 0.000 title claims description 33
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 102000011782 Keratins Human genes 0.000 claims description 36
- 108010076876 Keratins Proteins 0.000 claims description 36
- 239000000975 dye Substances 0.000 claims description 33
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 30
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 30
- -1 4-hydroxy-5-methoxy indole 6-hydroxy-7-methoxy indole Chemical compound 0.000 claims description 27
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 23
- 238000001035 drying Methods 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 239000000499 gel Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 6
- 229940093476 ethylene glycol Drugs 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000000982 direct dye Substances 0.000 claims description 2
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229940057867 methyl lactate Drugs 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000035515 penetration Effects 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 230000008961 swelling Effects 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- IPDOBVFESNNYEE-UHFFFAOYSA-N 1h-indole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1NC=C2 IPDOBVFESNNYEE-UHFFFAOYSA-N 0.000 claims 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical class COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
- 238000002360 preparation method Methods 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 235000019441 ethanol Nutrition 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000010586 diagram Methods 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 230000002269 spontaneous effect Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 238000004040 coloring Methods 0.000 description 8
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 244000303965 Cyamopsis psoralioides Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 150000002475 indoles Chemical class 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 241000282372 Panthera onca Species 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 5
- 229920013806 TRITON CG-110 Polymers 0.000 description 5
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 5
- 229930182470 glycoside Natural products 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 4
- NRDWNEPJYZPMKF-UHFFFAOYSA-N 3-ethoxy-6-nitro-2-phenylmethoxybenzaldehyde Chemical compound CCOC1=CC=C([N+]([O-])=O)C(C=O)=C1OCC1=CC=CC=C1 NRDWNEPJYZPMKF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MELKKMWBHMVCPQ-UHFFFAOYSA-N 4-methoxy-2,3-dimethyl-1h-indol-7-ol Chemical compound COC1=CC=C(O)C2=C1C(C)=C(C)N2 MELKKMWBHMVCPQ-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- MNYARIILPGRTQL-WPRPVWTQSA-N Ephedroxane Chemical compound O1C(=O)N(C)[C@@H](C)[C@H]1C1=CC=CC=C1 MNYARIILPGRTQL-WPRPVWTQSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002826 nitrites Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- FLHHXRRHNQZUGO-UHFFFAOYSA-N 2,2-dinitroethenylbenzene Chemical compound [O-][N+](=O)C([N+]([O-])=O)=CC1=CC=CC=C1 FLHHXRRHNQZUGO-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- OFQBYHLLIJGMNP-UHFFFAOYSA-N 3-ethoxy-2-hydroxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1O OFQBYHLLIJGMNP-UHFFFAOYSA-N 0.000 description 2
- BIANZVZZKGIQKG-UHFFFAOYSA-N 4-[4-(5-hydroxypentoxy)phenyl]benzonitrile Chemical compound C1=CC(OCCCCCO)=CC=C1C1=CC=C(C#N)C=C1 BIANZVZZKGIQKG-UHFFFAOYSA-N 0.000 description 2
- GJWMTPFFXQLITC-UHFFFAOYSA-N 4-hydroxy-3,5-dimethoxy-2-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=C([N+]([O-])=O)C(OC)=C1O GJWMTPFFXQLITC-UHFFFAOYSA-N 0.000 description 2
- VASQXZIEEJSNHC-UHFFFAOYSA-N 5-ethoxy-1-methylindol-4-ol Chemical compound CCOC1=CC=C2N(C)C=CC2=C1O VASQXZIEEJSNHC-UHFFFAOYSA-N 0.000 description 2
- LYZYLCBKDYUUES-UHFFFAOYSA-N 5-ethoxy-1h-indol-4-ol Chemical compound CCOC1=CC=C2NC=CC2=C1O LYZYLCBKDYUUES-UHFFFAOYSA-N 0.000 description 2
- YETIMTDBQRIDJA-UHFFFAOYSA-N 5-ethoxy-2-methyl-1h-indol-4-ol Chemical compound CCOC1=CC=C2NC(C)=CC2=C1O YETIMTDBQRIDJA-UHFFFAOYSA-N 0.000 description 2
- MLWZIKOJBGAQDZ-UHFFFAOYSA-N 5-ethoxy-4-phenylmethoxy-1h-indole Chemical compound CCOC1=CC=C2NC=CC2=C1OCC1=CC=CC=C1 MLWZIKOJBGAQDZ-UHFFFAOYSA-N 0.000 description 2
- NUMLTQFTLCZMRX-UHFFFAOYSA-N 5-methoxy-1h-indol-4-ol Chemical compound COC1=CC=C2NC=CC2=C1O NUMLTQFTLCZMRX-UHFFFAOYSA-N 0.000 description 2
- POWIOYMWSWIXAY-UHFFFAOYSA-N 5-methoxy-2-methyl-1h-indol-4-ol Chemical compound COC1=CC=C2NC(C)=CC2=C1O POWIOYMWSWIXAY-UHFFFAOYSA-N 0.000 description 2
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 2
- MVKYMRASKNZUGO-UHFFFAOYSA-N 7-methoxy-1h-indol-6-ol Chemical compound COC1=C(O)C=CC2=C1NC=C2 MVKYMRASKNZUGO-UHFFFAOYSA-N 0.000 description 2
- GCMRLOYLVFJGGA-UHFFFAOYSA-N 7-methoxy-2,3-dimethyl-1h-indol-4-ol Chemical compound COC1=CC=C(O)C2=C1NC(C)=C2C GCMRLOYLVFJGGA-UHFFFAOYSA-N 0.000 description 2
- CCMQDFAWOKJNEC-UHFFFAOYSA-N 7-methoxy-2,3-dimethyl-4-phenylmethoxy-1h-indole Chemical compound C1=2C(C)=C(C)NC=2C(OC)=CC=C1OCC1=CC=CC=C1 CCMQDFAWOKJNEC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1c(*)cc(C=O)c(*)c1C Chemical compound Cc1c(*)cc(C=O)c(*)c1C 0.000 description 2
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- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
- 125000002977 L-tyrosinyl radical cation group Chemical group 0.000 description 2
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- 150000001299 aldehydes Chemical class 0.000 description 2
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- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- FLJPGEWQYJVDPF-UHFFFAOYSA-L caesium sulfate Chemical compound [Cs+].[Cs+].[O-]S([O-])(=O)=O FLJPGEWQYJVDPF-UHFFFAOYSA-L 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
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- 230000001590 oxidative effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- AUSNPAAEIKJBEW-UHFFFAOYSA-N benzenesulfonic acid;3-ethoxy-2-hydroxybenzaldehyde Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC1=CC=CC(C=O)=C1O AUSNPAAEIKJBEW-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
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- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- MGZTXXNFBIUONY-UHFFFAOYSA-N hydrogen peroxide;iron(2+);sulfuric acid Chemical compound [Fe+2].OO.OS(O)(=O)=O MGZTXXNFBIUONY-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
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- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
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- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
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- 238000010907 mechanical stirring Methods 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- HAAYBYDROVFKPU-UHFFFAOYSA-N silver;azane;nitrate Chemical compound N.N.[Ag+].[O-][N+]([O-])=O HAAYBYDROVFKPU-UHFFFAOYSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- 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
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87338A LU87338A1 (fr) | 1988-09-12 | 1988-09-12 | Utilisation de derives d'indole pour la teinture de matieres keratiniques,compositions tinctoriales,composes nouveaux et procede de teinture |
| CH3214/89A CH679552A5 (enExample) | 1988-09-12 | 1989-09-05 | |
| IT8967757A IT1232923B (it) | 1988-09-12 | 1989-09-11 | Uso di derivati di indolo per la tintura di sostanze cheratiniche, composizioni tintorie, nuovi composti e procedimento di tintura |
| GB8920525A GB2224754B (en) | 1988-09-12 | 1989-09-11 | Use of indole derivatives for dyeing keratin materials,tinctorial compositions,new compounds and dyeing process |
| FR8911816A FR2636237B1 (fr) | 1988-09-12 | 1989-09-11 | Utilisation de derives d'indole pour la teinture de matieres keratiniques, compositions tinctoriales, composes nouveaux et procede de teinture |
| BE8900963A BE1002259A4 (fr) | 1988-09-12 | 1989-09-11 | Utilisation de derives d'indole pour la teinture de matieres keratiniques, compositions tinctoriales, composes nouveaux et procede de teinture. |
| JP1235511A JP2907453B2 (ja) | 1988-09-12 | 1989-09-11 | インドール誘導体およびケラチン染色組成物 |
| CA000611133A CA1333399C (fr) | 1988-09-12 | 1989-09-12 | Utilisation de derives d'indole pour la teinture de matieres keratiniques, compositions tinctoriales, composes nouveaux et procede de teinture |
| DE3930446A DE3930446A1 (de) | 1988-09-12 | 1989-09-12 | Verwendung von indolderivaten zur faerbung keratinischer materialien, faerbemittel, neue verbindungen und faerbeverfahren |
| US07/769,811 US5131911A (en) | 1988-09-12 | 1991-10-02 | Use of indole derivative for dyeing keratin materials, tinctorial compositions, new compounds and dyeing process |
| US07/864,410 US5354870A (en) | 1988-09-12 | 1992-04-06 | Indole derivatives for dyeing keratin materials |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87338 | 1988-09-12 | ||
| LU87338A LU87338A1 (fr) | 1988-09-12 | 1988-09-12 | Utilisation de derives d'indole pour la teinture de matieres keratiniques,compositions tinctoriales,composes nouveaux et procede de teinture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87338A1 true LU87338A1 (fr) | 1990-04-06 |
Family
ID=19731090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87338A LU87338A1 (fr) | 1988-09-12 | 1988-09-12 | Utilisation de derives d'indole pour la teinture de matieres keratiniques,compositions tinctoriales,composes nouveaux et procede de teinture |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5131911A (enExample) |
| JP (1) | JP2907453B2 (enExample) |
| BE (1) | BE1002259A4 (enExample) |
| CA (1) | CA1333399C (enExample) |
| CH (1) | CH679552A5 (enExample) |
| DE (1) | DE3930446A1 (enExample) |
| FR (1) | FR2636237B1 (enExample) |
| GB (1) | GB2224754B (enExample) |
| IT (1) | IT1232923B (enExample) |
| LU (1) | LU87338A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5346509A (en) * | 1988-05-12 | 1994-09-13 | Clairol Incorporated | Process for dyeing hair by the sequential treatment of hair with metal ion-containing composition and with a dye composition containing 5,6-dihydroxyindole-2-carboxylic acid and certain derivatives thereof |
| LU87403A1 (fr) * | 1988-12-06 | 1990-07-10 | Oreal | Procede de teinture de fibres keratiniques avec un hydroxyindole,associe a un derive quinonique |
| FR2654335A1 (fr) * | 1989-11-10 | 1991-05-17 | Oreal | Compositions tinctoriales pour fibres keratiniques contenant des precurseurs de colorants par oxydation et des coupleurs derives du 4-hydroxyindole, et procede de teinture les mettant en óoeuvre. |
| FR2654336B1 (fr) * | 1989-11-10 | 1994-06-03 | Oreal | Composition tinctoriale pour fibres keratiniques, contenant des precurseurs de colorants par oxydation et des coupleurs derives de 6- ou 7-hydroxyindole, et procede de teinture mettant en óoeuvre ces compositions. |
| FR2661673B1 (fr) * | 1990-05-07 | 1992-08-21 | Oreal | Association de dihydroxyacetone et de monohydroxyindoles pour conferer a la peau une coloration similaire au bronzage naturel, dispositif a plusieurs compartiments et procede de mise en óoeuvre. |
| FR2663651B1 (fr) * | 1990-06-21 | 1992-10-09 | Oreal | Procede de teinture des fibres keratiniques avec des composes indoliques, compositions et dispositifs de mises en óoeuvre. |
| US6238439B1 (en) | 1990-06-21 | 2001-05-29 | L'oreal | Method for dyeing keratinous fibers with indole compounds, compositions and devices for implementation |
| FR2664305B1 (fr) * | 1990-07-05 | 1992-10-09 | Oreal | Procede de teinture des fibres keratiniques avec des derives du 4-hydroxyindole a ph acide et compositions mise en óoeuvre. |
| FR2671722B1 (fr) * | 1991-01-21 | 1993-04-16 | Oreal | Utilisation de derives indoliques a titre de coupleurs dans la teinture des fibres keratiniques. |
| FR2681318A1 (fr) * | 1991-09-12 | 1993-03-19 | Oreal | Composition tinctoriale a base de derives d'hydroxyindoline, procede de teinture des fibres keratiniques et nouveaux derives d'hydroxyindoline. |
| US6569211B2 (en) | 1991-11-19 | 2003-05-27 | Henkel Kommanditgesellschaft Auf Aktien | 5,6-dihydroxyindolines as additives for hair dyeing preparations |
| DE4208297A1 (de) * | 1992-03-16 | 1993-09-23 | Henkel Kgaa | Faerben von keratinischen fasern mit indolinen unter metallkatalyse |
| US5413612A (en) * | 1992-04-29 | 1995-05-09 | Clairol Incorporated | Composition and method for dyeing hair with indolic compounds in the presence of a chlorite oxidant |
| FR2692782B1 (fr) * | 1992-06-25 | 1995-06-23 | Oreal | Procede de teinture des fibres keratiniques avec des derives indoliques ou indoliniques, du peroxyde d'hydrogene et une peroxydase. |
| US5368610A (en) * | 1993-04-20 | 1994-11-29 | Clairol Incorporated | Use of metal salts and chelates together with chlorites as oxidants in hair coloring |
| DE4331136C1 (de) * | 1993-09-14 | 1994-08-25 | Goldwell Ag | Mittel zum gleichzeitigen Färben und Aufhellen von menschlichen Haaren |
| US5435810A (en) * | 1993-12-27 | 1995-07-25 | Clairol Incorporated | Hair dyeing process with aminoalkylthio substituted dihydroxybenzene and oxidative agents |
| US5584889A (en) * | 1993-12-27 | 1996-12-17 | Clairol Incorporated | Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols |
| FR2722687A1 (fr) | 1994-07-22 | 1996-01-26 | Oreal | Utilisation de gomme de guar dans des compositionsnon rincees pour la teinture des fibres keratiniques et procede de teinture |
| FR2722686B1 (fr) * | 1994-07-22 | 1996-08-30 | Oreal | Set, procede, dispositif et composition de teinture des fibres keratiniques |
| FR2730925B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| FR2730923B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant une base d'oxydation, un coupleur indolique et un coupleur heterocyclique additionnel, et procede de teinture |
| FR2730926B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| FR2730922B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant au moins deux bases d'oxydation et un coupleur indolique, et procede de teinture |
| FR2730924B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Composition de teinture d'oxydation des fibres keratiniques comprenant un derive de diaminopyrazole et un coupleur heterocyclique et procede de teinture |
| FR2752574B1 (fr) * | 1996-08-23 | 1998-10-02 | Oreal | Derives de 2-imino-2,3-dihydro-1h-indoles, procedes de preparation, utilisations en cosmetique et dermatologie, compositions les mettant en oeuvre, procedes de teinture |
| US5792220A (en) * | 1997-05-16 | 1998-08-11 | Bristol-Myers Squibb Company | Dyeing hair with melanin procursors in the presence of iodate and peroxide |
| JP4140806B2 (ja) | 1998-06-23 | 2008-08-27 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | ケラチン繊維用の染色製剤 |
| FR2780880B1 (fr) * | 1998-07-09 | 2001-08-10 | Oreal | Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un polymere epaississant |
| FR2787707B1 (fr) * | 1998-12-23 | 2002-09-20 | Oreal | Procede de teinture mettant en oeuvre un derive cationique et un compose choisi parmi un aldehyde, une cetone, une quinone et un derive de la di-imino-isoindoline ou de la 3-amino-isoindolone |
| US20080311058A1 (en) * | 2007-06-18 | 2008-12-18 | Connopco, Inc., D/B/A Unilever | Stable high internal phase emulsions and compositions comprising the same |
| US8821839B2 (en) | 2010-10-22 | 2014-09-02 | Conopco, Inc. | Compositions and methods for imparting a sunless tan with a vicinal diamine |
| US8398959B2 (en) * | 2010-12-06 | 2013-03-19 | Conopco, Inc. | Compositions and methods for imparting a sunless tan with functionalized adjuvants |
| US8961942B2 (en) | 2011-12-13 | 2015-02-24 | Conopco, Inc. | Sunless tanning compositions with adjuvants comprising sulfur comprising moieties |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1217479A (en) * | 1915-08-02 | 1917-02-27 | Julia M Parker | Yard-truck. |
| LU56102A1 (enExample) | 1968-05-17 | 1970-01-14 | ||
| US3905999A (en) * | 1972-06-20 | 1975-09-16 | Eastman Kodak Co | Synthesis of 2,3-substituted indoles |
| FR2390158A1 (fr) * | 1977-05-10 | 1978-12-08 | Oreal | Compositions liquides de colorants de la famille des indoles destinees a la teinture des cheveux |
| CA1201067A (en) * | 1982-12-07 | 1986-02-25 | Keith Brown | Hair dyeing process and composition |
| LU86256A1 (fr) * | 1986-01-20 | 1988-01-20 | Oreal | Procede de teinture des fibres keratiniques avec du 5,6-dihydroxyindole associe avec un iodure |
| LU86314A1 (fr) * | 1986-02-20 | 1987-09-10 | Oreal | Procede de teinture des fibres keratiniques humaines avec le 5,6-dihydroxyindole et un anion metallique |
| LU86346A1 (fr) * | 1986-03-06 | 1987-11-11 | Oreal | Compositions tinctoriales pour fibres keratiniques a base de derives d'indole et composes nouveaux |
| LU86668A1 (fr) * | 1986-11-17 | 1988-06-13 | Oreal | Procede de teinture des fibres keratiniques avec des derives d'indole associes avec un iodure |
| US4776857A (en) * | 1986-11-21 | 1988-10-11 | Repligen Corporation | Use of hydroxylated indoles as dye precursors |
| LU86833A1 (fr) * | 1987-04-02 | 1988-12-13 | Oreal | Procede de teinture des fibres keratiniques avec le 5,6-dihydroxyindole associe a un iodure et une composition de peroxyde d'hydrogene a ph alcalin |
| US4932977A (en) * | 1988-11-21 | 1990-06-12 | Clairol Incorporated | Indole-aldehyde hair dyes |
| LU87403A1 (fr) * | 1988-12-06 | 1990-07-10 | Oreal | Procede de teinture de fibres keratiniques avec un hydroxyindole,associe a un derive quinonique |
-
1988
- 1988-09-12 LU LU87338A patent/LU87338A1/fr unknown
-
1989
- 1989-09-05 CH CH3214/89A patent/CH679552A5/fr not_active IP Right Cessation
- 1989-09-11 IT IT8967757A patent/IT1232923B/it active
- 1989-09-11 JP JP1235511A patent/JP2907453B2/ja not_active Expired - Fee Related
- 1989-09-11 FR FR8911816A patent/FR2636237B1/fr not_active Expired - Fee Related
- 1989-09-11 GB GB8920525A patent/GB2224754B/en not_active Expired - Lifetime
- 1989-09-11 BE BE8900963A patent/BE1002259A4/fr not_active IP Right Cessation
- 1989-09-12 CA CA000611133A patent/CA1333399C/fr not_active Expired - Fee Related
- 1989-09-12 DE DE3930446A patent/DE3930446A1/de not_active Withdrawn
-
1991
- 1991-10-02 US US07/769,811 patent/US5131911A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB8920525D0 (en) | 1989-10-25 |
| CA1333399C (fr) | 1994-12-06 |
| CH679552A5 (enExample) | 1992-03-13 |
| IT1232923B (it) | 1992-03-05 |
| FR2636237B1 (fr) | 1994-05-20 |
| JPH02115163A (ja) | 1990-04-27 |
| GB2224754A (en) | 1990-05-16 |
| GB2224754B (en) | 1992-07-29 |
| DE3930446A1 (de) | 1990-03-22 |
| US5131911A (en) | 1992-07-21 |
| FR2636237A1 (fr) | 1990-03-16 |
| IT8967757A0 (it) | 1989-09-11 |
| BE1002259A4 (fr) | 1990-11-06 |
| JP2907453B2 (ja) | 1999-06-21 |
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