KR0180037B1 - 6-또는 7-모노히드록시인돌을 사용하는 산성 pH에서의 케라틴섬유 염색방법과 그 조성물 - Google Patents
6-또는 7-모노히드록시인돌을 사용하는 산성 pH에서의 케라틴섬유 염색방법과 그 조성물 Download PDFInfo
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- KR0180037B1 KR0180037B1 KR1019910003710A KR910003710A KR0180037B1 KR 0180037 B1 KR0180037 B1 KR 0180037B1 KR 1019910003710 A KR1019910003710 A KR 1019910003710A KR 910003710 A KR910003710 A KR 910003710A KR 0180037 B1 KR0180037 B1 KR 0180037B1
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxy
- group
- dyeing
- hydrogen atom
- composition
- Prior art date
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- 238000004043 dyeing Methods 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 14
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- 239000000835 fiber Substances 0.000 title description 16
- 102000011782 Keratins Human genes 0.000 title description 11
- 108010076876 Keratins Proteins 0.000 title description 11
- 230000002378 acidificating effect Effects 0.000 title description 6
- 239000002243 precursor Substances 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007800 oxidant agent Substances 0.000 claims abstract description 14
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 4
- -1 7-hydroxy-3-methyl Indole 7 -Hydroxy-4-methoxy-2,3-dimethylindole Chemical compound 0.000 claims description 24
- 230000001590 oxidative effect Effects 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 21
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
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- BSNHKSUAAMJXBB-UHFFFAOYSA-N ethyl 5-hydroxy-2-methyl-1h-indole-3-carboxylate Chemical compound C1=C(O)C=C2C(C(=O)OCC)=C(C)NC2=C1 BSNHKSUAAMJXBB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
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- 230000037308 hair color Effects 0.000 description 1
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- 210000004080 milk Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000017281 sodium acetate Nutrition 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
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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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
-
- 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
Landscapes
- 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)
- Coloring (AREA)
- Indole Compounds (AREA)
- Detergent Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (7)
- 염색용 매질 속에 다음 구조식(Ⅰ)의 인돌-기초 결합제 및 이의 염과 산화염료 전구체를 함유하는 조성물로 구성된 성분(A)와 염색매질에 산화제를 함유하는 조성물로 구성된 성분(B)를 포함하며, 90 내지 10%의 성분(A)와 10 내지 90%의 성분(B)를 혼합하면 조성물의 pH가 7미만이 되는 염색제여기서 R1은 수소원자나 C1-C4알킬기이고; R2와 R3는 같거나 상이하며 수소원자, C1-C4저급알킬기, 카르복실기 또는 알콕시카르보닐기이고; X는 수소원자, C1-C4저급알킬기, C2-C18알콕시기, 할로겐원자, C2-C20아실옥시기 또는 아세틸아미노기이고; OH기는 방향족 링의 5- 또는 6- 또는 7-위치를 차지한다.
- 제1항에 있어서, 구조식(Ⅰ)의 화합물이 6-히드록시인돌, 6-히드록시-3-메톡시카르보닐-인돌, 6-히드록시-1-메틸-3-메톡시카르보닐인돌, 6-히드록시-1-메틸-2,3-디메톡시-카르보닐인돌, 6-히드록시-1,2-디메틸인돌, 6-히드록시-2-메틸인돌, 6-히드록시-2-카르복시인돌, 6-히드록시-2,3-디메틸인돌, 6-히드록시-3-카르복시인돌, 6-히드록시-3-에톡시카르보닐인돌, 6-히드록시-2-에톡시카르보닐인돌, 6-히드록시-3-메틸인돌, 6-히드록시-1-메틸인돌, 6-히드록시-5-아세톡시인돌, 6-히드록시-5-메톡시인돌, 6-히드록시-5-메톡시-2-메틸인돌, 6-히드록시-5-부톡시인돌, 6-히드록시-5-메톡시인돌-2-카르복시산, 6-히드록시-5-메톡시-2,3-디메틸인돌, 6-히드록시-7-메톡시인돌, 6-히드록시-5-테트라데카노일옥시인돌, 6-히드록시-5-헥사데실옥시인돌, 7-히드록시인돌, 7-히드록시-3-메틸인돌, 7-히드록시-4-메톡시-2,3-디메틸인돌, 6-히드록시-5-메톡시-1-메틸인돌, 6-히드록시-7-메틸인돌, 6-히드록시-2-에톡시카르보닐-5-메톡시인돌, 6-히드록시-2-메톡시카르보닐-5-부틸인돌, 6-히드록시-2,3-디메틸-5-(아세틸아미노)인돌, 5-히드록시-2-메틸-3-에톡시카르보닐인돌과 또한 5-히드록시-2-카르복시인돌 중에서 선택됨을 특징으로 하는 염색제.
- 제1항에 있어서, 산화염료 전구체를 파라-페닐렌디아민, 파라-아미노페놀 또한 파라-헤테로고리 전구체중에서 선택하는 것을 특징으로 하는 염색제.
- 제1항에 있어서, 산화염료 전구체가 오르토-아미노페놀 또는 오르토-페닐렌디아민에서 선택된 오르토 산화염료 전구체임을 특징으로 하는 염색제.
- 제1항에 있어서, 상기 조성물이 구조식(Ⅰ)의 6- 또는 7-히드록시인돌류의 헤테로고리 결합제에 추가적으로 메타-디페놀, 메타-아미노페놀, 메타-페닐렌디아민, 메타-아실아미노페놀, 메타-우레이도페놀, 메타-카르발콕시아미노페놀이나 α-나프타놀 같은 결합제 혹은 β-케톤화합물과 피라졸론같이 활성메틸렌기를 가진 결합제를 포함하는 것을 특징으로 하는 염색제.
- 제1격실에 염색용 매질 속에 다음 구조식(Ⅰ)의 인돌-기초 결합제 및 이의 염과 산화염료 전구체를 함유하는 조성물로 구성된 성분(A)를 함유하고 제2격실에 염색매질에 산화제를 함유하는 조성물로 구성된 성분(B)를 함유하는 이중격실로 구성된 것을 특징으로 하는 다중-격실염색장치여기서 R1은 수소원자나 C1-C4알킬기이고; R2와 R3는 같거나 상이하며 수소원자, C1-C4저급알킬기, 카르복실기 또는 알콕시카르보닐기이고; X는 수소원자, C1-C4저급알킬기, C2-C18알콕시기, 할로겐원자, C2-C20아실옥시기 또는 아세틸아미노기이고; OH기는 방향족 링의 5- 또는 6- 또는 7-위치를 차지한다.
- 제6항에 있어서, 성분(A)와 성분(B)의 혼합물을 모발에 전달하는 수단이 있음을 특징으로 하는 염색장치.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9002975 | 1990-03-08 | ||
FR909002975A FR2659228B1 (fr) | 1990-03-08 | 1990-03-08 | Procede de teinture des fibres keratiniques avec des 6 ou 7-monohydroxy-indoles a ph acide et compositions mises en óoeuvre. |
Publications (2)
Publication Number | Publication Date |
---|---|
KR910017021A KR910017021A (ko) | 1991-11-05 |
KR0180037B1 true KR0180037B1 (ko) | 1999-03-20 |
Family
ID=9394537
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910003710A KR0180037B1 (ko) | 1990-03-08 | 1991-03-08 | 6-또는 7-모노히드록시인돌을 사용하는 산성 pH에서의 케라틴섬유 염색방법과 그 조성물 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5207798A (ko) |
EP (1) | EP0446132B1 (ko) |
JP (1) | JP3254225B2 (ko) |
KR (1) | KR0180037B1 (ko) |
AT (1) | ATE111345T1 (ko) |
AU (1) | AU652741B2 (ko) |
BR (1) | BR9100931A (ko) |
CA (1) | CA2037816C (ko) |
DE (1) | DE69103932T2 (ko) |
DK (1) | DK0446132T3 (ko) |
ES (1) | ES2060313T3 (ko) |
FR (1) | FR2659228B1 (ko) |
MX (1) | MX171207B (ko) |
PT (1) | PT96958B (ko) |
ZA (1) | ZA911646B (ko) |
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KR20150008643A (ko) * | 2013-07-15 | 2015-01-23 | (주)아모레퍼시픽 | 5,6-디하이드록시인돌과 산화촉진제를 함유하는 모발용 화장료 조성물 |
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US5279620A (en) * | 1988-09-12 | 1994-01-18 | L'oreal | Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers, and dyeing processes using these compositions |
US5645609A (en) * | 1991-08-01 | 1997-07-08 | L'oreal | Compositions which contain and processes which use an insoluble pigment obtained by the oxidative polymerization of indole derivatives for the temporary dyeing of keratinous fibers |
US6569211B2 (en) | 1991-11-19 | 2003-05-27 | Henkel Kommanditgesellschaft Auf Aktien | 5,6-dihydroxyindolines as additives for hair dyeing preparations |
US5518506A (en) * | 1992-04-09 | 1996-05-21 | L'oreal | Process for dyeing keratinous fibres with an alkaline composition containing para-aminophenols substituted in position 2 in combination with 6- or 7-hydroxindole |
FR2689761B1 (fr) * | 1992-04-09 | 1995-06-23 | Oreal | Procede de teinture des fibres keratiniques en milieu alcalin mettant en óoeuvre des paraaminophenols substitues en position 2 en association avec le 6-ou 7-hydroxyindole et compositions mises en óoeuvre dans le procede. |
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. |
FR2700266B1 (fr) * | 1993-01-11 | 1995-03-03 | Oreal | Utilisation de sel de magnésium dans un procédé de teinture des fibres kératiniques mettant en Óoeuvre le 5,6-dihydroxyindole ou l'un de ses dérivés, procédés et compositions les mettant en Óoeuvre. |
FR2704149B1 (fr) * | 1993-04-23 | 1995-06-09 | Oreal | Utilisation de derives de la benzomorpholine ou 3,4-dihydro-2h-1,4 benzoxazine dans des compositions cosmetiques ou dermopharmaceutiques a action depigmentante. |
US5554197A (en) * | 1994-07-19 | 1996-09-10 | Anthony Bernard Incorporated | Hair dying system and methods for accurately blending and developing hair dye |
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 |
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 |
DE19643060A1 (de) * | 1996-10-18 | 1998-04-23 | Wella Ag | Mittel und Verfahren zur Färbung von keratinischen Fasern |
GB9626712D0 (en) * | 1996-12-23 | 1997-02-12 | Procter & Gamble | Hair colouring compositions |
US6432147B1 (en) | 1996-12-23 | 2002-08-13 | The Procter & Gamble Company | Hair coloring compositions |
GB9626675D0 (en) * | 1996-12-23 | 1997-02-12 | Procter & Gamble | Hair coloring compositions |
GB9626713D0 (en) * | 1996-12-23 | 1997-02-12 | Procter & Gamble | Hair colouring compositions |
US6398821B1 (en) | 1996-12-23 | 2002-06-04 | The Procter & Gamble Company | Hair coloring compositions |
US6309426B1 (en) | 1996-12-23 | 2001-10-30 | The Procter & Gamble Company | Hair coloring compositions |
GB9626711D0 (en) * | 1996-12-23 | 1997-02-12 | Procter & Gamble | Hair colouring compositions |
US6074438A (en) * | 1998-03-03 | 2000-06-13 | Bristol-Myers Squibb Co. | Hair dyeing compositions containing 2-chloro- and 2,6-dichloro-4-aminophenol and phenylpyrazolones |
CA2335959C (en) | 1998-06-23 | 2008-12-16 | Horst Hoffkes | Colorants |
KR100691086B1 (ko) * | 2006-01-26 | 2007-03-12 | 주식회사 엘지생활건강 | 산성 염모제 조성물 |
MX345233B (es) | 2012-03-27 | 2016-12-02 | Noxell Corp | Composiciones colorantes para el cabello que comprenden amino-2,6-dimetilfenol y reveladores tipo 1,4-fenilendiamina, metodos y estuches que comprenden las composiciones. |
JP6434902B2 (ja) | 2012-03-27 | 2018-12-05 | ノクセル・コーポレーション | 3−アミノ−2,6−ジメチルフェノールを含む染毛剤組成物、方法、並びに組成物を含むキット |
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GB211517A (en) * | 1923-05-22 | 1924-02-28 | Henry Andrews | Improvements in or appertaining to the manufacture of portland cement |
NL224577A (ko) * | 1957-02-02 | |||
US4013404A (en) * | 1970-12-06 | 1977-03-22 | American Cyanamid Company | Method of dyeing hair with indolines, indoles and indazoles |
LU86256A1 (fr) * | 1986-01-20 | 1988-01-20 | Oreal | Procede de teinture des fibres keratiniques avec du 5,6-dihydroxyindole associe avec un iodure |
LU86668A1 (fr) * | 1986-11-17 | 1988-06-13 | Oreal | Procede de teinture des fibres keratiniques avec des derives d'indole associes avec un iodure |
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 |
LU86899A1 (fr) * | 1987-05-25 | 1989-01-19 | Oreal | Procede de teinture des fibres keratiniques avec des colorants d'oxydation associes a un iodure et composition tinctoriale mise en oeuvre |
LU86947A1 (fr) * | 1987-07-17 | 1989-03-08 | Oreal | Procede de teinture des fibres keratiniques,en particulier humaines,avec le 5-(hydroxy ou-methoxy)6-hydroxyindole |
LU87086A1 (fr) * | 1987-12-18 | 1989-07-07 | Oreal | Procede de teinture des fibres keratiniques avec des colorants d'oxydation associes au 5,6-dihydroxyindole et a un iodure et composition tinctoriale mise en oeuvre |
LU87128A1 (fr) * | 1988-02-08 | 1989-09-20 | Oreal | Composition de teinture des fibres keratiniques mettant en oeuvre du 5,6-dihydroxyindole et au moins une paraphenylenediamine disubstituee sur l'un des groupements amino et procede de mise en oeuvre |
LU87333A1 (fr) * | 1988-09-08 | 1990-04-06 | Oreal | Procede de teintures des fibres keratiniques avec un derive d'indole associe a un nitrite et composition de mise en oeuvre |
LU87336A1 (fr) * | 1988-09-12 | 1990-04-06 | Oreal | Procede de teinture des fibres keratiniques avec un monohydroxyindole associe a un iodure et compositions mises en oeuvre |
LU87337A1 (fr) * | 1988-09-12 | 1990-04-06 | Oreal | Compositions tinctoriales pour fibres keratiniques contenant des precurseurs de colorants par oxydation et des coupleurs indoliques et procedes de teinture mettant en oeuvre ces compositions |
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. |
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. |
-
1990
- 1990-03-08 FR FR909002975A patent/FR2659228B1/fr not_active Expired - Fee Related
-
1991
- 1991-03-06 AT AT91400618T patent/ATE111345T1/de not_active IP Right Cessation
- 1991-03-06 EP EP91400618A patent/EP0446132B1/fr not_active Expired - Lifetime
- 1991-03-06 ES ES91400618T patent/ES2060313T3/es not_active Expired - Lifetime
- 1991-03-06 DE DE69103932T patent/DE69103932T2/de not_active Expired - Lifetime
- 1991-03-06 ZA ZA911646A patent/ZA911646B/xx unknown
- 1991-03-06 DK DK91400618.4T patent/DK0446132T3/da active
- 1991-03-07 US US07/666,187 patent/US5207798A/en not_active Expired - Lifetime
- 1991-03-07 PT PT96958A patent/PT96958B/pt not_active IP Right Cessation
- 1991-03-07 BR BR919100931A patent/BR9100931A/pt not_active IP Right Cessation
- 1991-03-07 AU AU72692/91A patent/AU652741B2/en not_active Ceased
- 1991-03-08 JP JP12559691A patent/JP3254225B2/ja not_active Expired - Fee Related
- 1991-03-08 KR KR1019910003710A patent/KR0180037B1/ko not_active IP Right Cessation
- 1991-03-08 CA CA002037816A patent/CA2037816C/fr not_active Expired - Fee Related
- 1991-05-07 MX MX024812A patent/MX171207B/es unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150008643A (ko) * | 2013-07-15 | 2015-01-23 | (주)아모레퍼시픽 | 5,6-디하이드록시인돌과 산화촉진제를 함유하는 모발용 화장료 조성물 |
Also Published As
Publication number | Publication date |
---|---|
ATE111345T1 (de) | 1994-09-15 |
AU7269291A (en) | 1991-09-12 |
EP0446132B1 (fr) | 1994-09-14 |
JP3254225B2 (ja) | 2002-02-04 |
PT96958B (pt) | 1998-07-31 |
JPH0692828A (ja) | 1994-04-05 |
BR9100931A (pt) | 1991-11-05 |
FR2659228A1 (fr) | 1991-09-13 |
DK0446132T3 (da) | 1995-01-23 |
CA2037816C (fr) | 2002-07-16 |
ES2060313T3 (es) | 1994-11-16 |
EP0446132A1 (fr) | 1991-09-11 |
PT96958A (pt) | 1991-10-31 |
FR2659228B1 (fr) | 1994-10-14 |
KR910017021A (ko) | 1991-11-05 |
CA2037816A1 (fr) | 1991-09-09 |
ZA911646B (en) | 1991-12-24 |
DE69103932D1 (de) | 1994-10-20 |
MX171207B (es) | 1993-10-07 |
DE69103932T2 (de) | 1995-02-09 |
AU652741B2 (en) | 1994-09-08 |
US5207798A (en) | 1993-05-04 |
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