MXPA00001642A - DYEING COMPOSITION CONTAINING A PYRAZOLO-[1,5-a]-PYRIMIDINE AS OXIDATION BASE AND A PYRIDINE COUPLING AGENT, AND DYEING METHOD - Google Patents
DYEING COMPOSITION CONTAINING A PYRAZOLO-[1,5-a]-PYRIMIDINE AS OXIDATION BASE AND A PYRIDINE COUPLING AGENT, AND DYEING METHODInfo
- Publication number
- MXPA00001642A MXPA00001642A MXPA/A/2000/001642A MXPA00001642A MXPA00001642A MX PA00001642 A MXPA00001642 A MX PA00001642A MX PA00001642 A MXPA00001642 A MX PA00001642A MX PA00001642 A MXPA00001642 A MX PA00001642A
- Authority
- MX
- Mexico
- Prior art keywords
- amino
- composition
- radical
- pyridine
- alkyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 238000004043 dyeing Methods 0.000 title claims abstract description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 21
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title claims abstract description 10
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-Dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000007822 coupling agent Substances 0.000 title claims abstract 3
- 230000003647 oxidation Effects 0.000 claims abstract description 25
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 25
- -1 C1-C4 alkyl radical Chemical class 0.000 claims description 35
- 239000000835 fiber Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 102000011782 Keratins Human genes 0.000 claims description 21
- 108010076876 Keratins Proteins 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 239000011780 sodium chloride Substances 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 17
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 17
- 210000004209 Hair Anatomy 0.000 claims description 14
- 238000010186 staining Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 12
- 230000001590 oxidative Effects 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000002255 enzymatic Effects 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl radical Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000001264 neutralization Effects 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- BXBOXUNPNIJELB-UHFFFAOYSA-N 2,6-dimethoxypyridine-3,5-diamine Chemical compound COC1=NC(OC)=C(N)C=C1N BXBOXUNPNIJELB-UHFFFAOYSA-N 0.000 claims description 2
- HMRIWBBWYXEHRZ-UHFFFAOYSA-N 2-propoxypyridine Chemical compound CCCOC1=CC=CC=N1 HMRIWBBWYXEHRZ-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N Hydrogen peroxide - urea Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007945 N-acyl ureas Chemical class 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- 229940072033 potash Drugs 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- PNFZIEOWPDFJBH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C=NN21 PNFZIEOWPDFJBH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003890 succinate salts Chemical class 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive Effects 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 27
- 235000019441 ethanol Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 206010001488 Aggression Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000014961 Protein Precursors Human genes 0.000 description 2
- 108010078762 Protein Precursors Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000104757 Viola obliqua Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000000240 adjuvant Effects 0.000 description 2
- 230000016571 aggressive behavior Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000003750 conditioning Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-Methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- RPTFEYVETOJOPF-UHFFFAOYSA-N 2-(3,4-diamino-6-methoxypyridin-2-yl)ethanol Chemical compound COC1=CC(N)=C(N)C(CCO)=N1 RPTFEYVETOJOPF-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- HARBPHQCTIDSBX-UHFFFAOYSA-N 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)amino]ethanol Chemical compound NC1=CC=NC2=C(NCCO)C=NN12 HARBPHQCTIDSBX-UHFFFAOYSA-N 0.000 description 1
- MWXUGXZKBKIMKB-UHFFFAOYSA-N 2-methylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C(C)=NN21 MWXUGXZKBKIMKB-UHFFFAOYSA-N 0.000 description 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-Aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 1
- VNECCGPOXBLLOG-UHFFFAOYSA-N 5-amino-2,6-dimethoxypyridin-3-ol Chemical compound COC1=NC(OC)=C(O)C=C1N VNECCGPOXBLLOG-UHFFFAOYSA-N 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N Aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229940106189 Ceramides Drugs 0.000 description 1
- 240000005497 Cyamopsis tetragonoloba Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 229960003330 Pentetic Acid Drugs 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N Phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 229960005323 Phenoxyethanol Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia NH3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001783 ceramides Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000295 complement Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- FFNJDUZBKSGSIV-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,5-diamine Chemical compound C1=CC(N)=NC2=C(N)C=NN21 FFNJDUZBKSGSIV-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000002110 toxicologic Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Abstract
The invention concerns an oxidation dyeing composition for keratinous fibres containing at least a pyrazolo-[1,5-a]-pyrimidine as oxidation base and at least a pyridine coupling agent and the oxidation dyeing method using said composition.
Description
COMPOSITION OF DYE CONTAINING A PIRAZOLO- [1, 5-a] -PIRIMIDINE, AS AN OXIDATION BASE AND A PIRIDINE COUPLER, AND STAINING PROCEDURES Description of the invention: The invention aims at a composition for dyeing, by of the oxidation, of the keratin fibers, wherein the composition contains at least one I or - [1, 5-a] -pyrimidine pyrazole, as the base oxidation, and at least one pyridine coupler; as well as a dyeing process, by means of oxidation, which uses this composition. Methods are known for dyeing keratin fibers and, in particular, human hair, with dyeing compositions containing oxidation dye precursors and, in particular, ortho- or para-phenylenediamines, ortho- or para-aminophenols, from the bis-f eni I to the I-endiamines also, from the heterocyclic compounds, generally called oxidation bases. The oxidation dye precursors, or oxidation bases, are colorless, or slightly colored, compounds that, when combined with oxidizing products, can give rise, through oxidative condensation processes, to colored compounds and dyes, REF .: 32750 Tam It is well known that the nuances obtained with these bases of oxidation can be varied by their association with couplers or modifiers of the coloration, where the latter s choose mainly between the aromatic meta-amines, the meta-aminophen I is, the meta-diphenone I is certain compounds heterocyclic The variety of molecules that can be used at the level of oxidation bases and couplers allows a rich range of colors to be obtained. The coloration called "permanent", which is obtained thanks to the oxidation dyes, must, on the other hand, satisfy a certain number of demands. Thus, there should be no drawbacks in the toxicological field; it must allow to obtain matice with the desired intensity and it must present good protection against the external agents (light, weather, washing, permanent waving, perspiration, rubbing). The dyes must also make it possible to cover the white hairs, and, lastly, to be as selective as possible, that is to say, to obtain the faintest possible color differences over the entire length of the same keratin fiber, which may, in fact, sensitize in a deferred (i .e., spoiled) manner between its tip and its root. It has already been proposed, in particular in the application FR-A-2 750 048, to use the p i r a z or I o - [1, 5-a] pyrimidines, as oxidation bases, alone or in association with one or more couplers. However, the colors obtained are not always strong enough, chromatic or resistant to the different aggressions that the hair can suffer. Now, the Applicant has discovered, quite unexpectedly and surprisingly, that the association of pyrazo I or - [1, 5 - a] - pyrimidines, of the formula (I), which are defined below, and less a pyridine coupler, of the formula (II), which is described below, allows to obtain strong colorations which also present; better resistance properties against the various aggressions that the hair can suffer (shampoo, light, weathering, permanent waving, perspiration, friction, etc.). These discoveries are the basis of the present invention. The invention then has, as a first objective, a composition for oxidation staining of keratin fibers, and in particular, of human keratin fibers, such as hair, where the composition is characterized by containing, in an appropriate medium for staining (dye): - at least one oxidation base chosen from pyrazolo- [l, 5-a] -pyrimidines, of the following formula (I), and their addition salts with an acid or a base :
in which: - Rx, R2, R3 and R4 designate, in an identical or different manner, a hydrogen atom, an alkyl radical of C i -C 4, a radical on a ryl, a hydroxyalkyl radical of C 1 -C 4, a polyhydroxyalkyl radical of C 2 -C 4, an alkoxy radical (C 1 -C 4) C 1 -C 4 alkyl, a C 1 -C 4 aminoalkyl radical (the amine may be protected by an acetyl, a ureide, a sulfonyl), an alkyl radical (C 1 -C 4) aminoalkyl of C1-C4, a radical di- [a I qui I (C 1 - C 4)] amino C 1 -C 4 alkyl (the dialkyls can form an aliphatic or heterocyclic ring with 5 or 6 links), a hydroxyl radical I qui I (C 1 -C 4) - or di- [hydroxy I qui I (C 1 -C 4)] - amino C 1 -C 4 alkyl;
- the radicals X, identical or different, denote a hydrogen atom, an alkyl radical of C? -C4, an aryl radical, a hydroxyalkyl radical of C i -C 4, a polyhydroxyalkyl radical of C2-C4, an amino alkyl radical of C i -C 4, a C 1 -C 4 alkyl-amino-C 1 -C 4 alkyl radical, a di- [a l-C 1 -C 4)] amino-C 1 -C 4 alkyl radical (the dialkyls can form an aliphatic or heterocyclic ring with 5 or 6 links), a hydroxy radical at I qui (C x -C 4) or di- [hydroxy (C 1 -C 4) alkyl] amino C 1 -C 4 alkyl, a radical amino, a radical to I qui I (C 1 -C 4) - or di- [(C 1 -C 4) alkyl] -amino; a halogen atom, a carboxylic acid group, a sulfonic acid group; - i has the value 0, 1, 2 or 3; - p has the value 0 or 1; - q has the value 0 or 1; - n has the value 0 or 1; provided that: (i) the sum of p + q is different from 0; (ii) when p + q equals 2, then n is 0 and the groups NR? R2 and NR3R4 occupy positions (2,3); (5,6); (6,7); (3.5) or (3.7);
(iii) when p + q equals 1, then n is 1 and the group N R i R 2 (or NR3R4) and the group OH occupy the positions (2,3); (5,6); (6,7); (3.5) or (3.7); - and at least one coupler chosen from the pyridines of the following formula (II), and their addition salts with an acid:
wherein: - R 5 represents a hydrogen atom, a hydroxyl radical, amino, C 1 -C 4 alkoxy, mono- or di-alkyl (C 1 -C 4) amino, monohydroxyalkyl (C 4 -C 4) amino, polyhydroxyalkyl (C2-C4) amino, monohydroxyalkyl (C1-C4), monohydroxy I coxy (C2-C4), C6-4 alkoxy, or monohydroxyalkoxy (C6-4) C 1 -C alkoxy 4; - R6 represents a hydrogen atom, a hydroxyl radical, amine or C 1 -C 4 alkyl; R7 represents a hydrogen atom, or a C 1 -C 4 alkyl radical; R8 represents an hydrogen or halogen atom such as chlorine, bromine, iodine or fluorine, or an amino radical;
- R9 represents a hydrogen atom, a hydroxyl radical, amino, C4-C4 alkoxy, monohydric and C4-C4 alkoxy, or C2-C polyhydroxyalkoxy; wherein at least one of the radicals R5 to R9 are different from a hydrogen atom; and the composition is free of any enzymatic system capable of causing the oxidation of the compounds of the formula (I) and / or (II). As indicated above, the composition of the dye, according to the invention, leads to strong colorations having excellent resistance properties against the action of the different external agents (light, weather, washing, permanent waving, perspiration, friction). The invention also aims at a process for oxidation staining of keratin fibers, where this dye composition is applied. The pyrazolo- [1, 5-a] -pyrimidines of the formula (I) which can be used as oxidation base in the dye composition according to the invention are known compounds and are described in the application FR-A-2 750 048, the content of which forms an integral part of the present application. Among the pyrazoles I or - [1, 5 - a] - pyrimidines, of the formula (I), which can be used as oxidation base in the dyeing compositions according to the invention, mention may be made in particular of: pyrazolo- [1, 5-a] -pyrimidine-3,7-diamine; 2-methyl pyrazolo- [1, 5-a] -pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo- [1, 5-a] -pyrimidin-3,7-d i a m a n; pyrazolo- [1, 5-a] -pyrimidine-3,5-diamine; - the 2,7-dimethyl p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 3, 5 - d i a m i n a; - 3-am ino p i r a z o 1 o - [1, 5 - a] - p i r i m i d i n - 7 - or I; - 3-am ino 5-methyl pyrazolo- [1, 5-a] -pyrim idin-7-ol;
- the 3-amino p i r a z or I o - [1, 5 - a] - p i f i m i d i n - 5 - or I; - the 2- (3-amino p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 7 - i a m i n o) - e t a n o I; - the 3 - a m i n o - 7 - ß - h i d r o x i e t i i a m i n o - 5 - m e t i I - p i r a z o I o - [l, 5-a] -pyrimine; 2- (7-amino pyrazolo- [1, 5-a] -pyrimidin-3-ylamino) -ethanol; - 2 - [(3 - a m i n o - p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 7 - i I) - (2-hydroxyethyl) -amino] -ethanol;
- 2 - [(7-m i n o-p i r a zo I o - [1, 5 -a] - p i r i m i d i n - 3 - i I) - (2-hydroxyethyl) -amino] -ethanol; - 5,6-dimethyl p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 3, 7 - d i a m a n a; - 2,6-dimethyl p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 3, 7 - d i a m a n a; - 2, 5, N - 7, N - 7 - 1 e t r a m e t i i i i i i i - [1, 5 - a] - p i r i m i d i n - 3,7-diam ina; and their addition salts with an acid or a base. Among the pyridines of the formula (II) which can be used as couplers in the dyeing compositions according to the invention, mention may be made in particular of: 2,6-hydroxy-3,4-dimethyl pyridine; -chloro 2,3-dihydroxy pyridine, 3,5-diamino-2,6-dimethoxy pyridine, 3-amino 2- (β-hydroxyethyl) amino 6-methoxy pyridine,
- 2,6-bis (β-hydroxyethyloxy) 3,5-diamino pyridine, 3-amino-5-hydroxy-2,6-dimethoxy pyridine, - 3-amino-2-methylamino-6-methoxy pyridine, -amino 3-hydroxy pyridine, 2-dimethylamine 5-amino pyridine, 2,6-diamino pyridine, - 3,5-diamino 2- (β, β-d ihydroxy) propyloxy pyridine, - la 3, 5-diamino 2 - (? - hydroxypropyloxyethyloxy) pyridine, and its addition salts with an acid. In general, the addition salts with an acid, which can be used within the framework of the invention (oxidation bases and couplers), are chosen especially among the hydrochlorides, the bromohydrates, the sulfates, the citrates, the succinates, the tartrates , lactates and acetates. Addition salts with a base, which can be used in the context of the dyeing compositions of the invention, are especially those obtained with soda, potash, ammonia or mines. The pyrazolo- [1, 5-a] -pyrim idine (s), of the formula (I), according to the invention, and / or the one or more addition salts thereof with an acid or with a base, they preferably represent from 0.0005 to 12%, by weight, approximately, of the total weight of the dye composition and, even more preferably, from 0.005 to 6%, by weight, approximately, of this weight. The pyridine (s) of the formula (II), according to the invention, and / or the addition salt (s) thereof with an acid, preferably represent 0.0001 to 10%, by weight , approximately, of the total weight of the composition of the dye and, even more preferably, of 0.005 to 5%, by weight, of this weight. The suitable medium for dyeing (or support) is generally constituted by water or by a mixture of water and at least one organic solvent, to solubilize the com positions that are not sufficiently soluble in water. As the organic solvent, for example, C?-C 4 alkanols, such as ethanol and isopropanol, may be mentioned; glycerol; glycols and ethers of glycols, such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol; analogs and their mixtures. The solvents may be present in proportions com pounded, preferably, between 1 and 40%, by weight, approximately, with respect to the total weight of the dye composition and, even more preferably, between 5 and 30%, by weight, approximately . The pH of the dye composition, according to the invention, is generally between about 3 and 12, and preferably between about 5 and about 11. It can be adjusted to the desired value by acidification or alkalinity agents, which are usually used for the staining of keratin fibers. Examples of acidic agents include mineral or organic acids, such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid. , sulfonic acids. Alkalinity agents include, for example, ammonia; alkaline carbonates; alkanolamines, such as mono-, di- and triethanolamines, 2-methyl-2-amino-propanol, and their derivatives; the sodium or potassium hydroxides and the compounds of the following formula (III):
R 10 12 VN-W-N / (III) / \ ^ 11 R13
wherein W is a residue of propylene, optionally substituted by a hydroxyl group or an alkyl radical of C i -C 6; Rio, p, 12 and Rn, identical or different, represent a hydrogen atom, a C 1 -C 6 alkyl radical, or d-C 6 hydroxyalkyl.
The composition of the dye, according to the invention, can also comprise at least one direct dye, especially to modify the shades or enrich them in reflections. The composition of the dye, according to the invention, can also comprise various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, polymers anionic, cationic, nonionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickeners, such as, for example, non-ionic guar gums, antioxidants, penetration agents, sequestering agents, perfumes, buffers, dispersing agents conditioning agents, such as, for example, volatile or non-volatile silicones, modified or unmodified, film forming agents, ceramides, preservatives, opacifiers. As is understood, the person skilled in the art will take care to choose the optional complementary compounds, in such a way that the advantageous properties intrinsically linked to the composition of the oxidation dye, according to the invention, are not, at least not substance, altered by the programmed addition (s). The composition of the dye, according to the invention, can be presented in various forms, such as in the form of liquids, powders, creams, gels or in any other suitable form for dyeing the keratin fibers, and especially the hair. humans. Another object of the invention is a method of oxidation staining of keratin fibers and, in particular, of human keratin fibers, such as hair, which uses the composition of the dye, as defined above.
According to this method, at least one composition of the dye is applied to the fibers, as defined above; the coloration is revealed at acid, neutral or alkaline pH with the aid of an oxidizing, non-enzymatic agent, which is added just at the time of use of the dye composition or which is present in an oxidizing composition that is applied at the same time or sequentially.
According to a preferred embodiment of the dyeing process of the invention, the composition of the dye described above is mixed, preferably at the time of use, with an oxidizing composition containing, in a medium suitable for dyeing, at least one non-enzymatic oxidizing agent present in an amount sufficient to develop a coloration. The mixture obtained is then applied onto the keratin fibers and left for about 3 to 50 minutes, preferably, about 5 to 30 minutes, after which it is rinsed, washed with water, rinsed again and dry The oxidizing agent present in the oxidizing composition, as defined above, may be chosen from the oxidizing agents conventionally used for oxidation staining of keratin fibers, and among which may be mentioned hydrogen peroxide, urea peroxide , alkali metal bromates, peracids and persalts such as perborates and persulfates. Hydrogen peroxide is the particularly preferred.
The pH of the oxidizing composition comprising the oxidizing agent, as defined above, is such that, after mixing with the composition of the dye, the pH of the resulting composition applied to the keratin fibers varies preferably. between 3 and 12, approximately, still more preferably, between 5 and 11. It is adjusted to the desired value by means of the acidifying agents to I c n a n d i n a ls commonly used for the staining of keratin fibers and as defined above. The oxidized composition, as defined above, may also comprise various adjuvants conventionally used in hair dyeing compositions, and as defined above. The composition that is finally applied on the keratin fibers can be presented in various forms, such as liquids, creams, gels, or on any other suitable form for dyeing the keratin fibers and especially the human hair. Another object of the invention is a device with several companions or dyeing "equipment", any other conditioning system having different compartments, where a prime compartment contains the composition of the tint (dye), as defined above, and a second compartment contains the oxidizing composition, as defined above. These devices can be equipped with a device that allows distributing the desired mixture on the hair, such as the devices described in patent FR-586 913, to the name of the applicant. The following examples are intended to illustrate the invention, without being of a limiting character.
EXAMPLES EXAMPLES 1 to 3, DYEING IN ALKALINE EDGE The following d staining compositions have been prepared, according to the invention (quantity e grams):
(*) Support for common dye no. 1: - Ethyl alcohol of 96 ° 18
- Sodium metabisulphite in 35% aqueous solution 0.68 g Diethylenetriaminepentaacetic acid pentasodium salt 1.1 g 20% NH3 ammonia 10.0 g
At the time of use, each of the staining compositions described above is mixed with a solution of hydrogen peroxide up to 20 volumes (6% by weight), co pH 3. The mixture obtained is applied to the Mechone of natural gray hair, with 90% white, for 30 minutes. The strands are immediately rinsed, washed with a standard shampoo, rinsed again, then dried. The nuances obtained are shown in the following table: EXAMPLE pH of the dye Tint obtained 1 10 ± 0.2 Red ashy iridescent 2 10 ± 0.2 Red violet purple 3 10 ± 0.2 Red purple violet
EXAMPLES 4 to 6, DYEING IN NEUTRAL MEDIUM The following dyeing compositions were prepared, according to the invention (content in grams):
(*) Support for common dye no. 2: - Ethanol 96 ° 18 g
- Shock absorber K2HP04 / KH2P04 (1.5 M / l M) 10 g
- Sodium metabisulfite 0.68 G
- Pentasodic salt of diethylenetriaminepentaacetic acid 1.1 G
At the time of use, each of the dyeing compositions described above is mixed, weight by weight, with a solution of hydrogen peroxide up to 20 volumes (6% by weight), with pH 3.
The mixture obtained is applied to the natural gray-haired mechone, with 90% white for 30 minutes. The strands are immediately rinsed, washed with a standard shampoo, rinsed again, then dried. The nuances obtained are shown in the following table: EXAMPLE pH of the dye Tint obtained 4 5.7 ± 0.2 Iridescent ashy red 5 5.7 ± 0.2 Iridescent 6 5.7 ± 0.2 Red purple violet
It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (11)
- R8 represents a hydrogen atom or d halogen such as chlorine, bromine, iodine or fluorine or an amino radical; - R9 represents a hydrogen atom, a hydroxyl radical, amino, C C-C4 monohydroxyalkoxyl alkoxy of d-C4, or polyhydroxyalkoxy d C 2 -C 4; wherein at least one of the radicals R5 to R9 is different from a hydrogen atom; and the position is free of any enzymatic system capable of causing the oxidation of the compounds of the formula (I) and / or (II).
- 2. The composition, according to claim 1, characterized in that the pyrazolo [l, 5-a] -pyrimidines, of the formula (I), is chosen from: pyrazolo- [1, 5-a] -pyrimidin- 3,7-diamine; - the 2-methyl p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 3, 7 - d i a m a n a; - 2,5-dimethylpyrazolo- [1, 5-a] -pyrim idin-3,7 d i a m a n a; - pyrazoyl- [1, 5-a] -pyrimidine-3,5-diamine; - the 2,7-dimethyl p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 3, 5 d a m a n a; - 3-amino pyrazolo- [1, 5-a] -pyrimidin-7-ol; - 3-amino 5-methyl p i r a zo I o - [1, 5 - a] - p i r i m i d i n - 7 - or I; - the 3-amino p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 5 - or I; - the 2- (3-am ino p i r a z o I o - [1, 5 - a] - p i r i m i d i n - 7 - i a m i n o) ethanol; - 3-amino-7-β-hydroxyethylamino-5-methyl-pyrazolo [1, 5-a] -pyrim idine; - the 2- (7-am ino p i r a z o I o - [1, 5 - a] - p i r i m i d i n - 3 - i a m i n o) ethanol; - 2 - [(3 - a m i n o - p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 7 - i I) - (2-hydroxyethyl) -amino] -ethanol; - 2 - [(7-amino-pyrazolo- [1, 5-a] -pyrimidin-3-yl) - (2-hydroxyethyl) -amne] -ethanol; - 5,6-dimethyl p i r a z or I o - [1, 5 - a] - p i r i m i d i n - 3, 7 d a m a n a; - 2,6-dimethylpyrazolo- [1, 5-a] -pyrim idin-3,7 d a a m i n a; 2,5, N-7, N-7-tetramethyl pyrazolo- [l, 5-a] -pyrim idin 3,7-diamine; and their addition salts with an acid or a base.
- 3. The composition, according to any of claims 1 or 2, characterized in that the pyridines, of the formula (II), are chosen from: 2,6-hydroxy-3,4-dimeti-pyridine, - 5-chloro-2 , 3-dihydroxy pyridine, 3,5-diamino-2,6-dimethoxy pyridine, - 3-amino 2- (β-hydroxyethyl) amino 6-methoxy pyridine, - 2,6-bis (β-hydroxyethyloxy) 3,5-diamino pyridine, - 3-amino-5-hydroxy-2,6-dimethoxy-pyridine, - 3-amino-2-methylamino-6-methoxy pyridine, - 2-amino-3-hydroxy-pyridine, - 2-dimethylamino-5- amino pyridine, - 2,6-diamino pyridine, - 3,5-diamino 2- (β, β-dihydroxy) propyloxy pyridine, - the 3,5-diamino 2 - (? - h i d r or x i p r or p i I x i e t i I or x i) pyridine, and its addition salts with an acid.
- 4. The composition according to any of claims 1 to 3, characterized in that the addition salts with an acid are chosen from the hydrochlorides, the bromohydrates, the sulfates, the citrates, the succinates, the tartrates, the lactates, the acetates; and because the addition salts with a base are chosen from those obtained with l soda, potash, ammonia or amines.
- 5. The composition, according to any of the preceding claims, characterized in that, or the, pyrazolo- [1, 5-a] -pyrim idines, of the formula (I), and / or, or, the salt (s) is ) of addition with an acid with a base, represent from 0.0005 to 12%, by weight of the total weight of the composition of the dye.
- 6. The composition, according to claim 5, characterized in that the, or the pyrazoo- [1, 5-a] -pyrimidine (s), of the formula (I) and / or, or, the salt (s) of addition with an acid or a base, they represent from 0.005 to 6%, by weight, of the total weight of the dye composition.
- 7. The composition, according to any of the preceding claims, characterized in that the pyridine (s) of the formula (II) and / or the additive salt (s) with an acid represent 0.0001 to 10%, by weight, of the total weight of the dye composition.
- 8. The composition, according to claim 7, characterized in that the, or the, pyridine (s) of the formula (II), and / or the, or their, salt (is addition with an acid, represent 0.005 to 5%, by weight, of the total weight of the dye composition.
- 9. A process for oxidation staining of keratin fibers, and in particular human keratin fibers, such as hair, characterized in that at least one composition of the dye is applied to the fibers, as defined in any of the claims 1 to 8, and because the color reveals an acid, neutral or alkaline pH, with the help of an oxidizing, non-enzymatic agent, which is added just at the time of using the dye composition, or which is present. and an oxidizing composition that is applied to my time or sequentially.
- 10. The process according to claim 9, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, perishes and persalts.
- 11. A device with various compartments, dyeing "equipment", having several compartments, characterized in that a first compartment contains a composition of the dye, as defined in any of claims 1 to 8; and because a second composition contains an oxidizing composition containing a non-enzymatic oxidizing agent. SUMMARY OF THE INVENTION The invention concerns a composition for the staining of keratin fibers, wherein the composition contains at least one pyrazolo- [1, 5-a] -pyrimidine, as oxidation base, and at least one pyridine coupling agent; as well as the oxidation staining process where this composition is used.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR98/07797 | 1998-06-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA00001642A true MXPA00001642A (en) | 2001-03-05 |
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