DE3045959C2 - - Google Patents
Info
- Publication number
- DE3045959C2 DE3045959C2 DE19803045959 DE3045959A DE3045959C2 DE 3045959 C2 DE3045959 C2 DE 3045959C2 DE 19803045959 DE19803045959 DE 19803045959 DE 3045959 A DE3045959 A DE 3045959A DE 3045959 C2 DE3045959 C2 DE 3045959C2
- Authority
- DE
- Germany
- Prior art keywords
- hair
- phenylenediamine
- hydroxyalkyl
- coupler
- developer
- 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.)
- Expired
Links
- 239000000118 hair dye Substances 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 230000037308 hair color Effects 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- -1 hydroxyalkyl radical Chemical group 0.000 description 24
- 239000000839 emulsion Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 229940018564 m-phenylenediamine Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 238000005691 oxidative coupling reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 2
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 description 2
- YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 description 2
- VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XYAQUYKPDDPZHG-UHFFFAOYSA-N 1-(4-aminoanilino)propan-2-ol Chemical compound CC(O)CNC1=CC=C(N)C=C1 XYAQUYKPDDPZHG-UHFFFAOYSA-N 0.000 description 1
- PZKPUGIOJKNRQZ-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,3-diamine Chemical class CC1(N)CC(N)=CC=C1 PZKPUGIOJKNRQZ-UHFFFAOYSA-N 0.000 description 1
- NXVHEHXRZVQDCR-UHFFFAOYSA-N 1-n,1-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1C NXVHEHXRZVQDCR-UHFFFAOYSA-N 0.000 description 1
- HQCHAOKWWKLXQH-UHFFFAOYSA-N 2,6-Dichloro-para-phenylenediamine Chemical compound NC1=CC(Cl)=C(N)C(Cl)=C1 HQCHAOKWWKLXQH-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- WRPDHMGXFGCCPT-UHFFFAOYSA-N 2-[(2,5,6-triaminopyrimidin-4-yl)amino]ethanol Chemical compound NC1=NC(N)=C(N)C(NCCO)=N1 WRPDHMGXFGCCPT-UHFFFAOYSA-N 0.000 description 1
- YQPYJIJMQMCMAQ-UHFFFAOYSA-N 2-[2-(4-aminophenyl)-2-(2-hydroxyethylamino)hydrazinyl]ethanol Chemical compound NC1=CC=C(N(NCCO)NCCO)C=C1 YQPYJIJMQMCMAQ-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- HSVBSQWCIQIJNQ-UHFFFAOYSA-N 2-n,4-n-dimethylpyrimidine-2,4,5,6-tetramine Chemical compound CNC1=NC(N)=C(N)C(NC)=N1 HSVBSQWCIQIJNQ-UHFFFAOYSA-N 0.000 description 1
- CGSYHUHHSJWEKH-UHFFFAOYSA-N 3-(3-aminoanilino)propan-1-ol Chemical compound NC1=CC=CC(NCCCO)=C1 CGSYHUHHSJWEKH-UHFFFAOYSA-N 0.000 description 1
- KELHBBKYAHRJPR-UHFFFAOYSA-N 3-(3-aminoanilino)propane-1,2-diol Chemical compound NC1=CC=CC(NCC(O)CO)=C1 KELHBBKYAHRJPR-UHFFFAOYSA-N 0.000 description 1
- CSGNEKGWOJHKOI-UHFFFAOYSA-N 4-(4-azaniumyl-n-butylanilino)butane-1-sulfonate Chemical compound OS(=O)(=O)CCCCN(CCCC)C1=CC=C(N)C=C1 CSGNEKGWOJHKOI-UHFFFAOYSA-N 0.000 description 1
- RDURCWNWCVUFEG-UHFFFAOYSA-N 4-n,4-n-diethyl-6-n-methylpyrimidine-2,4,5,6-tetramine Chemical compound CCN(CC)C1=NC(N)=NC(NC)=C1N RDURCWNWCVUFEG-UHFFFAOYSA-N 0.000 description 1
- BKIIRHXARCYZNY-UHFFFAOYSA-N 4-n,4-n-dimethylpyrimidine-2,4,5,6-tetramine Chemical compound CN(C)C1=NC(N)=NC(N)=C1N BKIIRHXARCYZNY-UHFFFAOYSA-N 0.000 description 1
- SGWBUDIVEVIHND-UHFFFAOYSA-N 4-n-phenylpyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(NC=2C=CC=CC=2)=N1 SGWBUDIVEVIHND-UHFFFAOYSA-N 0.000 description 1
- DUHATDNXRFRRFH-UHFFFAOYSA-N 6-morpholin-4-ylpyrimidine-2,4,5-triamine Chemical compound NC1=NC(N)=C(N)C(N2CCOCC2)=N1 DUHATDNXRFRRFH-UHFFFAOYSA-N 0.000 description 1
- QKEUDMVNJHDWNZ-UHFFFAOYSA-N 6-piperidin-1-ylpyrimidine-2,4,5-triamine Chemical compound NC1=NC(N)=C(N)C(N2CCCCC2)=N1 QKEUDMVNJHDWNZ-UHFFFAOYSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803045959 DE3045959A1 (de) | 1980-12-05 | 1980-12-05 | "neue kupplerkomponenten fuer oxidationshaarfarben, deren herstellung und verwendung, sowie diese enthaltende haarfaerbemittel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803045959 DE3045959A1 (de) | 1980-12-05 | 1980-12-05 | "neue kupplerkomponenten fuer oxidationshaarfarben, deren herstellung und verwendung, sowie diese enthaltende haarfaerbemittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3045959A1 DE3045959A1 (de) | 1982-07-08 |
| DE3045959C2 true DE3045959C2 (en, 2012) | 1989-04-06 |
Family
ID=6118444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803045959 Granted DE3045959A1 (de) | 1980-12-05 | 1980-12-05 | "neue kupplerkomponenten fuer oxidationshaarfarben, deren herstellung und verwendung, sowie diese enthaltende haarfaerbemittel |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3045959A1 (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3644980A1 (de) * | 1986-12-24 | 1988-07-07 | Pav Praezisions Apparatebau Ag | Messkluppe |
| DE4132615C2 (de) * | 1991-10-01 | 1994-08-18 | Schwarzkopf Gmbh Hans | Substituierte 2,6-Diaminotoluole, Verfahren zu ihrer Herstellung sowie Färbemittel für keratinische Fasern, die diese enthalten |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE476810C (de) * | 1926-10-23 | 1929-05-25 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Trisazofarbstoffen |
| US2022245A (en) * | 1931-10-15 | 1935-11-26 | Gen Aniline Works Inc | Mono-n-alkanol derivative of aromatic di-amines and poly-amines |
| CA1025881A (en) * | 1973-10-15 | 1978-02-07 | Alexander Halasz | Dyeing keratin fibers with 2-substituted m-toluenediamines |
-
1980
- 1980-12-05 DE DE19803045959 patent/DE3045959A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3045959A1 (de) | 1982-07-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2628999C2 (de) | Haarfärbemittel | |
| EP0039030B1 (de) | Neue Kupplerkomponenten für Oxidationshaarfarben, deren Herstellung und Verwendung sowie diese enthaltende Haarfärbemittel | |
| DE2834605C2 (en, 2012) | ||
| EP0063736B1 (de) | Verwendung von Dihydroxypyridinen als Kupplerkomponente in Oxidationshaarfarbstoffen und Haarfärbemittel | |
| DE2934330C2 (en, 2012) | ||
| EP0036591B1 (de) | Neue Kupplerkomponenten für Oxidationshaarfarben, deren Herstellung und Verwendung sowie diese enthaltende Haarfärbemittel | |
| EP0002828B1 (de) | Haarfärbemittel | |
| EP0195361A2 (de) | Haarfärbemittel | |
| EP0029964A1 (de) | Neue Kupplerkomponenten für Oxidationshaarfarben, deren Herstellung und Verwendung sowie diese enthaltende Haarfärbemittel | |
| EP0107027B1 (de) | Haarfärbemittel | |
| EP0039806B1 (de) | Haarfärbemittel | |
| EP0270972A2 (de) | Oxidationshaarfärbemittel | |
| DE3045959C2 (en, 2012) | ||
| DE2852156C2 (de) | Haarfärbemittel auf der Basis von Oxidationsfarbstoffen und Bis-(2,4-diaminophenoxy)-alkane | |
| DE2934329C2 (en, 2012) | ||
| DE3824299A1 (de) | Haarfaerbemittel | |
| EP0195363B1 (de) | Haarfärbemittel | |
| DE2719424A1 (de) | Haarfaerbemittel | |
| DE3007997C2 (en, 2012) | ||
| DE2934331A1 (de) | Neue entwicklerkomponenten fuer oxidationshaarfarben, deren herstellung und verwendung, sowie diese enthaltende haarfaerbemittel. | |
| DE2932800C2 (en, 2012) | ||
| EP0024710A2 (de) | Haarfärbemittel | |
| EP0081790A1 (de) | Neue p-Phenylendiamine, deren Herstellung und Verwendung | |
| EP0280186B1 (de) | Haarfärbemittel mit direktziehenden Nitrodiphenylamin-Derivaten | |
| EP0039034B1 (de) | Kupplerkomponenten für Oxidationshaarfarben und deren Verwendung, sowie diese enthaltende Haarfärbemittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: A61K 7/13 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |