MXPA99010062A - Dyes composition containing a cationic direct coloring and a pirazolo- [1,5-a] -pirimidine a title of oxidation base, and procedures deti - Google Patents
Dyes composition containing a cationic direct coloring and a pirazolo- [1,5-a] -pirimidine a title of oxidation base, and procedures detiInfo
- Publication number
- MXPA99010062A MXPA99010062A MXPA/A/1999/010062A MX9910062A MXPA99010062A MX PA99010062 A MXPA99010062 A MX PA99010062A MX 9910062 A MX9910062 A MX 9910062A MX PA99010062 A MXPA99010062 A MX PA99010062A
- Authority
- MX
- Mexico
- Prior art keywords
- radical
- alkyl
- amino
- chosen
- pyrazolo
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000000975 dye Substances 0.000 title claims abstract description 46
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-Dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 10
- 125000002091 cationic group Chemical group 0.000 title claims description 31
- 238000004040 coloring Methods 0.000 title description 2
- 238000004043 dyeing Methods 0.000 claims abstract description 44
- 239000000835 fiber Substances 0.000 claims abstract description 23
- 230000003647 oxidation Effects 0.000 claims abstract description 23
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 23
- 102000011782 Keratins Human genes 0.000 claims abstract description 20
- 108010076876 Keratins Proteins 0.000 claims abstract description 20
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000982 direct dye Substances 0.000 claims abstract description 13
- -1 alkyl radical Chemical class 0.000 claims description 135
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 39
- 150000003254 radicals Chemical class 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000011780 sodium chloride Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 210000004209 Hair Anatomy 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011630 iodine Substances 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- 230000001590 oxidative Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005842 heteroatoms Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000002829 nitrogen Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000002255 enzymatic Effects 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-M Perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004434 sulfur atoms Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 3
- CMPPYVDBIJWGCB-UHFFFAOYSA-N [8-[(4-amino-3-nitrophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N\NC1=CC=C(N)C([N+]([O-])=O)=C1 CMPPYVDBIJWGCB-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 101700035385 lili Proteins 0.000 claims description 3
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N Cyano radical Chemical compound N#[C] JEVCWSUVFOYBFI-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
- WIJOZBDYRBXOOW-UHFFFAOYSA-N [8-[(4-amino-2-nitrophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1[N+]([O-])=O WIJOZBDYRBXOOW-UHFFFAOYSA-N 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
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 claims description 2
- 229940054051 antipsychotic Indole derivatives Drugs 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 229940072033 potash Drugs 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
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 150000003890 succinate salts Chemical class 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 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
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atoms Chemical group 0.000 claims 2
- 230000002378 acidificating Effects 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 claims 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 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
- 230000003113 alkalizing Effects 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
- 235000019441 ethanol Nutrition 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
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-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
- OOPWJBCZQDTTNE-UHFFFAOYSA-N 4-N-[4-(4-aminoanilino)butyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NCCCCNC1=CC=C(N)C=C1 OOPWJBCZQDTTNE-UHFFFAOYSA-N 0.000 description 2
- 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
- 229940083082 Pyrimidine derivatives acting on arteriolar smooth muscle Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000003086 colorant Substances 0.000 description 2
- 230000003750 conditioning Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000002391 heterocyclic compounds 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
- 229910052700 potassium Inorganic materials 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
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GHGPIPTUDQZJJS-UHFFFAOYSA-N (2-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Cl GHGPIPTUDQZJJS-UHFFFAOYSA-N 0.000 description 1
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 1
- RQKQKYICHBSFNX-UHFFFAOYSA-N (4,5-diamino-1-ethylpyrazol-3-yl)methanol Chemical compound CCN1N=C(CO)C(N)=C1N RQKQKYICHBSFNX-UHFFFAOYSA-N 0.000 description 1
- LHGUPKWTLOUVPW-UHFFFAOYSA-N (4,5-diamino-1-methylpyrazol-3-yl)methanol Chemical compound CN1N=C(CO)C(N)=C1N LHGUPKWTLOUVPW-UHFFFAOYSA-N 0.000 description 1
- DPTWQNJCRFZYPL-UHFFFAOYSA-N (4,5-diamino-1-propan-2-ylpyrazol-3-yl)methanol Chemical compound CC(C)N1N=C(CO)C(N)=C1N DPTWQNJCRFZYPL-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- AJDXVTCUJNIISK-UHFFFAOYSA-N 1-fluorocyclohexa-3,5-diene-1,2-diamine Chemical compound NC1C=CC=CC1(N)F AJDXVTCUJNIISK-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
- WSMJTXVQAZYLAV-UHFFFAOYSA-N 1-methylindol-4-ol Chemical compound C1=CC=C2N(C)C=CC2=C1O WSMJTXVQAZYLAV-UHFFFAOYSA-N 0.000 description 1
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1H-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
- WXFKWEVAPSWLOI-UHFFFAOYSA-N 1H-pyrazole-3,4,5-triamine Chemical compound NC1=NNC(N)=C1N WXFKWEVAPSWLOI-UHFFFAOYSA-N 0.000 description 1
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1H-pyrazole-4,5-diamine Chemical compound NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 description 1
- JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1H-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 description 1
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 description 1
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-1H-pyrimidin-4-one Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- BRMHZFZMBVIHMO-UHFFFAOYSA-N 2,5-dimethylpyrazole-3,4-diamine Chemical compound CC1=NN(C)C(N)=C1N BRMHZFZMBVIHMO-UHFFFAOYSA-N 0.000 description 1
- KEEQZNSCYCPKOJ-UHFFFAOYSA-N 2,6-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=CC(CC)=C1N KEEQZNSCYCPKOJ-UHFFFAOYSA-N 0.000 description 1
- WCPGNFONICRLCL-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C(N)=C1 WCPGNFONICRLCL-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-Methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 description 1
- GEDBTTQRNHWAQC-UHFFFAOYSA-N 2-(4-methoxyphenyl)pyridine-3,4-diamine Chemical compound C1=CC(OC)=CC=C1C1=NC=CC(N)=C1N GEDBTTQRNHWAQC-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- HJXIRCMNJLIHQR-UHFFFAOYSA-N 2-N,2-N-dimethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N HJXIRCMNJLIHQR-UHFFFAOYSA-N 0.000 description 1
- GYWDRJNSLRPYBQ-UHFFFAOYSA-N 2-[3-[2-(2,5-diaminophenoxy)ethoxymethoxy]propoxy]benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(OCCCOCOCCOC=2C(=CC=C(N)C=2)N)=C1 GYWDRJNSLRPYBQ-UHFFFAOYSA-N 0.000 description 1
- FLCAOAGLACNSPB-UHFFFAOYSA-N 2-[4-amino-N-[2-[4-amino-N-(2-hydroxyethyl)anilino]ethyl]anilino]ethanol Chemical compound C1=CC(N)=CC=C1N(CCO)CCN(CCO)C1=CC=C(N)C=C1 FLCAOAGLACNSPB-UHFFFAOYSA-N 0.000 description 1
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 description 1
- AJZRIOLJTXDFDY-UHFFFAOYSA-N 2-benzyl-5-methylpyrazole-3,4-diamine Chemical compound NC1=C(N)C(C)=NN1CC1=CC=CC=C1 AJZRIOLJTXDFDY-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- MEKRUGGNBTYVRV-UHFFFAOYSA-N 2-ethyl-5-methylpyrazole-3,4-diamine Chemical compound CCN1N=C(C)C(N)=C1N MEKRUGGNBTYVRV-UHFFFAOYSA-N 0.000 description 1
- LYEBIHUMFJCIMG-UHFFFAOYSA-N 2-methyl-5-phenylpyrazole-3,4-diamine Chemical compound NC1=C(N)N(C)N=C1C1=CC=CC=C1 LYEBIHUMFJCIMG-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- XOAXOKSJNVLLHZ-UHFFFAOYSA-N 2-methylpyrazole-3,4-diamine Chemical compound CN1N=CC(N)=C1N XOAXOKSJNVLLHZ-UHFFFAOYSA-N 0.000 description 1
- CTGVWWNOCSCKKI-UHFFFAOYSA-N 2-tert-butyl-5-methylpyrazole-3,4-diamine Chemical compound CC1=NN(C(C)(C)C)C(N)=C1N CTGVWWNOCSCKKI-UHFFFAOYSA-N 0.000 description 1
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
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- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
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- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
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Abstract
The subject of the invention is a composition for oxidation dyeing of keratin fibers, containing at least one canonical direct dye and at least one pyrazolo- [1,5-a] -pyrimidine as oxidation base, as well as the process of oxidation dye that employs this composition
Description
TINTÓREA COMPOSITION THAT CONTAINS A DIRECT COLORING
CATIÓNICO AND UNA PIRAZOLO- [1, 5- a] -PIRIMIDINA A TITLE OF
OXIDATION BASE, AND DYE PROCEDURES
DESCRIPTION OF THE INVENTION
The subject of the invention is a composition for oxidative dyeing of keratin fibers, containing at least one direct cationic dye and at least one pyrazolo- [1,5-a] -pyrimidine as an oxidation base; as well as the oxidation dye process employing this composition. It is known to dye keratin fibers and in particular human hair with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, bis-phenylalkylenediamines or even heterocyclic compounds, generally called oxidation bases. The oxidation dye precursors, or oxidation bases, are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, by a process of oxidative condensation, to colored compounds and dyes.
REF .: 31797 It is also known that the shades obtained with these oxidation bases can be varied by associating them with copulators or color modifiers, the latter being chosen mainly among aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds. The variety of molecules put into play at the level of oxidation bases and copulators allows obtaining a rich range of colors. The coloration called "permanent" obtained thanks to these oxidation dyes, must satisfy, in addition, a certain number of demands. Thus, it should not have drawbacks on the toxicological level, should allow obtaining tonalities in the desired intensity, and present a good resistance against external agents (light, weather, washing, permanent wave, perspiration, friction). The dyes must also make it possible to cover the white hairs, and, finally, to be as non-selective as possible, that is to say allow to obtain the smallest possible deviations of coloration throughout the same keratin fiber, which may be in fact sensitized. different (ie, spoiled) form between its tip and its root. It has already been proposed in particular in the patent application FR-A-2 750 048, to use pyrazolo- [1,5-a] -pyrimidine as an oxidation base, alone or in association with one or more couplers. However, the colors obtained are not always powerful enough, chromatic or resistant to the different aggressions that the hair can suffer. Now, the Applicant Firm has now discovered, in a totally unexpected and surprising way, that the association of at least one pyrazolo- [1,5-a] -pyrimidine as oxidation base and at least one direct cationic dye defined below allowed to obtain powerful colorations that also have improved resistance properties against various aggressions that hair can suffer (washed with shampoo, light, weather, undulations, perms, perspiration, friction, etc ...). These discoveries form the basis of the present invention. The invention therefore has as its first object a composition for dyeing by oxidation of keratin fibers, and in particular of human akeratin fibers such as hair, characterized in that it contains, in an appropriate medium for the hair. dye: - at least one pyrazolo- [1, 5-a-] -pyrimidine as an oxidation base; - and at least one direct cationic dye; said composition being exempt from any enzymatic system capable of causing the oxidation of the pyrazolo-1, 5-a] -pyrimidines. As indicated above, the dyeing composition according to the invention leads to potent colorations which also have, excellent resistance properties against the action of the different external agents (light, bad weather, washing, permanent wave, perspiration, friction). Another subject of the invention is a dyeing process by oxidation of the keratin fibers, which employs this dyeing composition. The pyrazolo- [1, 5-a] -pyrimidines which can be used as oxidation base in the dyeing composition according to the invention are preferably chosen from the following compounds of formula (V), and their addition salts with an acid or with one base:
wherein: R3j, RJ ,, R- and RjC designate, identical or different, a hydrogen atom, an alkyl radical of C? -Cj, an aryl radical, a hydroxyalkyl radical of C: - C, a polyhydroxyalkyl radical of C_-C, a (C1-C4) alkoxy C1-C4 alkyl radical, an amino-C1-C4 alkyl radical (the amine may be protected by an acetyl, a ureide, a sulfonyl), a radical (C_-C) ,) C 1 -C 4 alkyl alkylamino, a di- [(C ..- C, alkyl] amino C 1 -C 4 alkyl radical
(the dialkyls can form an aliphatic or heterocyclic ring with 5 or 6 links), a hydroxy radical (C: ~ C4) alkyl- or di- [hydroxy (C? -C4) alkyl] -amino alkyl of (C _ -C4) ); - the radicals R, identical or different, designate a hydrogen atom, an alkyl radical of C? -C4 an aryl radical, a hydroxyalkyl radical of C? ~ C4, a polyhydroxyalkyl radical of C ..- C4, a radical ( C? -C4) C 1 -C 4 alkylamino, a di- [(C 1 -C 4) alkyl] alkyl radical of C 1 -C 4 (the dialkyls can form an aliphatic or heterocyclic cycle with 5 or 6 links), a hydroxy radical (C 1 -C 4) alkyl or di- [hydroxy (dC 4) alkyl] amino C 1 -C 4 alkyl, an amino radical, a radical (C: -C 4) alkyl di [(C 1 -C) alkyl] -amino; a halogen atom, a carboxylic acid group, a sulfonic acid group; - i is worth 0, 1, 2 or 3 here; - p is worth 0 or 1 here; - that is worth 0 or 1 here; - n is worth 0 or 1 here; with the proviso that: - (i) the sum p + q is different from 0; - (ii) when p + q equals 2, then n is 0 and the groups NRXR ^ and NR ^ iR ^ e occupy the positions (2,
3); (5, 6); (6, 7); (3, 5) or (3,7); - (iii) when p + q is equal to 1, then n is worth 1 and the group NR __._ R._4 (or NR ^ R ^ and the group OH occupy the positions (2, 3); (5, 6); (6, 7); (3, 5) or (3, 7) The pyrazolo- [1, 5-a] -pyrimidines of formula (V) above are known compounds and described mainly in patent application FR-A -2 750 048, whose content forms an integral part of the present application.
Among the pyrazolo- [1, 5-a] -pyrimidines of formula (V), 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] ] -pyrimidin-3,7-diamine; - 2-methyl pyrazolo- [1,5-a] -pyrimidin-3,7-diamine; - 2,5-dimethylpyrazolo- [1,5-a] -pyrimidin-3,7-diamine;
- pyrazolo- [1, 5-a] -pyrimidin-3, 5-diamine; - 2,7-dimethylpyrazolo- [1, 5-a] -pyrimidin-3, 5-diamine; - 3-amino pyrazolo- [1,5-a] -pyrimidin-7-ol; - 3-amino-5-methyl pyrazolo- [1, 5-a] -pyrimidin-7-ol; 3-amino-5-methyl-7-imidazolylpropylamino pyrazole- [1,5-a] -pyrmidine; - 3-amino pyrazolo- [1, 5-a] -pyrimidin-5-ol; - 2- (3-amino pyrazolo- [1, 5-a] -pyrimidin-7-ylamino) ethanol; - 3-amino-7-β-hydroxyethylamino-5-methyl-pyrazolo- [1,5-a] -pyrimidine; - 2- (7-amino pyrazolo- [1, 5-a] -pyrimidin-3-ylamino) -ethanol; - 2- [(3-amlno-pyrazolo- [1, 5-a] -pyrimidin-7-yl) - (2-hydroxyethyl) -amino] -ethanol; - 2- [7-amino pyrazolo- [1, 5-a] -pyrimidin-3-yl) - (2-hydroxyethyl) -amino] -ethanol; 5,6-dimethylpyrazolo- [1,5-a] -pyrimidin-3,7-diamine; - 2,6-dimethylpyrazolo- [1,5-a] -pyrimidin-3,7-diamine;
2,5, N-7, N-7-tetramethyl pyrazolo- [1,5-a] -pyrimidin-3,7-diamine; and their addition salts with an acid or a base. The cationic direct dye (s), which can be used in the dyeing composition according to the invention, are preferably chosen from cationic aminoanthraquinones, cationic mono- or di-azoics, and cationic naphthoquinones. By way of example, mention may be made in particular of [8- [(p-aminophenyl) azol] -7-hydroxy-2-naphthyl] trimethylammonium chloride (also called Basic Brown 16® or Arianor Mahogany 306002 © in the Color Index) , the association of 3- [(4-amino-6-bromo-5,8-dihydro-l-hydroxy-8-imino-5-oxo-2-naphthalenyl) -amino] -N, N, -trimethylbencenaminium and of 3- [(2-chloride, 6-dibromo-5, 8-dihydro-l-hydroxy-8-imino-5-oxo-3-naphthyl) -amino] -N, N, N-trimethyl-benzenamine (also called Basic Blue 99 © or Arianor Steel Blue 306004® in the Color Index), the 7-hydroxy-8- [(2-methoxyphenyl) azo] -N, N, N-trimeti 1-2-naphthaleminium chloride (also called Basic Red 76 © or Arianor Madder Red® in Color Index), [8- [(4-amino-2-nitrophenyl) azo] -7-hydroxy-2-naphthyl] trimethylammonium chloride (also called Basic Red 118 © or Arianor Bordeaux 306006 © in the Color Index), the association of [8- [(4-amino-3-nitrophenyl) azo] -7-hydroxy-2-naphthyl] trimethylammonium chloride and [8- [(4-amino-2-nitrophenyl ) azo] -7-hydroxy-2-naphthyl] trimethylammonium (also called Basic Brown 17 © or Arianor Sienna Brown 306001 © in the Index color), 3- [4,5-dihydro-3-methyl-5- chloride] oxo-l-phenyl-lH-pyrazol-4-yl] -zo], N, -trimethyl-benzenamine (also called Basic Yellow 57® or Arianor Straw yellow 306005 © in Color Xndex), 1- (α-aminopropyl) amino anthraquinone hydrochloride, 1-N- (methyl-morpholinium-propyl) amino 4-hydroxy anthraquinone methylisulfate, and Basic Orange 69 © (Color Index denomination). The direct cationic dye (s) used in the dyeing composition according to the invention can also be selected from the compounds of the formulas (I), (II), (III), (III '), and
(IV) following:
a) compounds of the formula (I)
wherein: - D represents a nitrogen atom or the group -CH,
- Ri and R;, identical or different, represents a hydrogen atom; an alkyl radical of C: -C which can be substituted by a radical -CN, OH or -NH_ or form with a carbon atom of the benzene ring a possibly oxygenated or nitrogenated heterocycle, which may be substituted by one or more alkyl radicals of C1-C; a 4'-a-iniphenyl radical, - Rj and R'j, identical or different, represents a hydrogen atom or a halogen selected from chlorine, bromine, iodine, fluorine, a cyano radical, C1-C4 alkoxy or acetyloxy, -X ~ represents an anion preferably chosen from chloride, methyl sulfate and acetate, -A represents a group chosen by the following Al a19 structures:
A * * 3
A .. -2
, 0
.3 4 15 -6 A17 .8
wherein R. 'represents an alkyl radical of C_-C which may be substituted by a hydroxyl and R = represents a C1-C alkoxy radical, with the proviso that when D represents -CH, when A represents A or - and when R3 is different from an alkoxy radical, then Ri and R_. do not simultaneously designate a hydrogen atom;
b) compounds of formula (I I)
wherein: Rc represents a hydrogen atom or an alkyl radical of C; -C, RT represents a hydrogen atom, an alkyl radical, which may be substituted by a -CN radical or by an amino group, a radical 4 ' -aminophenyl or form with R6 an optionally oxygenated and / or nitrogenated heterocycle which can be substituted by an alkyl radical of C-, C, Rc and R .., identical or different, represent a hydrogen atom, a halogen atom, such as bromine, chlorine, iodine and / or fluorine, an alkyl radical of C 1 -C 4 -C 4 alkoxy, a -CN radical,
- X ~ represents an anion preferably chosen from the chloride, the methyl sulfate and the acetate. - B represents a group chosen from the following structures Bl to B6:
B4 B5 B6
wherein R- represents an alkyl radical of y-C-, R: and R12, identical or different, represent a hydrogen atom or an alkyl radical of Ci-Cí, "
c) compounds of the formula (III) and (III '):
wherein: - Rij represents a hydrogen atom, a C1-C4 alkoxy radical, a halogen atom, such as bromine, chlorine, iodine or fluorine or an amino radical, Ri, represents a hydrogen atom , an alkyl radical of C4-C4, or forms with a carbon atom of the benzene ring a heterocycle optionally oxygen and / or substituted by one or more C: -C4 alkyl groups, -R15 represents a hydrogen or halogen atom , such as bromine, chlorine, iodine or fluorine, -ie and R? -7, identical or different, represent a hydrogen atom or an alkyl radical of C? -C4, - Di and D_, identical or different , represent a nitrogen atom or the group -CH, - m = 0 or 1 with the understanding that when R 13 represents an unsubstituted amino group, then O? and D; simultaneously represent a group -CH and m = 0, - X "represents an anion preferably chosen from chloride, methyl sulfate and acetate, - E represents a group chosen by the structures Ei a
E ^ following:
E6 E7 E8
wherein R 'represents an alkyl radical of C? -C4; when m = 0 and when Di represents a nitrogen atom, then E can also designate a group of structure E9 as follows:
wherein R 'represents an alkyl radical of C¿-C4.
d) compounds of formula (IV)
N = N - J IV)
where - G represents a group chosen from the following G: a G¿ structures:
wherein: Ri. designates an alkyl radical of C? -C4, a phenyl radical, a phenyl radical substituted by an alkyl radical of C-C4, or a halogen atom selected from chlorine, bromine, iodine and fluorine; Ri9 designates a C1-C alkyl radical or a phenyl radical; R2. and R.sup.1, identical or different, represent a C 1 -C 4 alkyl radical, a phenyl radical, or together with Gi form a benzene ring substituted by one or more C 1 -C 4 alkyl radicals; C4 / o NO. or together with G_ they form a benzene ring optionally substituted by one or more C: -C4 alkyl radicals, C: -Calkoxy, or NO.; R_ can also designate a hydrogen atom; Z designates an oxygen atom, a sulfur atom or a group
-NR? 5; M represents a group -CH, -CR "(denoting R" alkyl of d-C4), or -NR;: (X "h; K represents a group -CH, -CR" (designating R "C? C4) or -NR__ (X ") _; P represents a group -CH, -CR" (denoting R "C 1 -C 4 alkyl), o -NR__ (X ~) r; r designates zero or 1; R 1 represents an O atom ", a C 1 -C 4 alkoxy radical, or an identical or different Ci-C, R___ and R_4 alkyl radical, represent a hydrogen or halogen atom chosen from chlorine, bromine, iodine and fluorine, an alkyl radical of C 1 -C 4, alkoxy of C 1 -C 4, a radical -NO_; X ~ represents an anion preferably chosen from chloride, iodide, methyl sulfate, etiisulfate, acetate and perchlorate; except that: when R__ designates O "then r designates zero;
when K or P or M designates a -N-C-C4 alkyl group X ~, then at least one of the radicals R; and R; _ is different from a hydrogen atom; when K designated -NRn (X ~) r. then M = P = -CH or -CR "; when M designates -NR __; (X") r. then K = P = -CH or -CR ", when P designates -NR; (X ~) r, then K = M and designates -CH or -CR; when Z designates a sulfur atom and R: designates an alkyl radical of C1-C4, then R, -, is different from a hydrogen atom, when Z designates -NR;;, and when R19 designates a C1-C4 alkyl radical, then at least one of the radicals R? ¿, ' R;, or R;., Of the structure group G; is different from an alkyl radical of C; -C4; J represents: • or a group of structure Ji below:
wherein: R; s represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a C1-C3 alkyl radical, C_-C4 alkoxy, an -OH radical , -N0, -NHR;, -NR_? R ?, -NHCOalkyl of C? -C4, or form with R;.s a 5 or 6 link cycle containing or not one or more heteroatoms chosen from nitrogen, oxygen and sulfur; R; 6 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, an alkyl radical of C_-C4, alkoxy of C1-C4, or a form with R __- or R; a cycle of 5 or 6 links, containing or not one or more heteroatoms chosen from nitrogen, oxygen or sulfur; - R; 7 represents' a hydrogen atom, a radical -OH, a radical -NHR;:, or a radical -NR_QR3I .; R_s represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, C 4 -C 4 polyhydroxyalkyl radical, or a phenyl radical; - R;, and Rj., Identical or different, represent a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, or polyhydroxyalkyl radical
C __- C4; Or a 5- or 6-membered heterocyclic heterocyclic group capable of containing other heteroatoms and / or carbonized groups and which may be substituted by one or more C 1 -C 4 alkyl radicals, amino or phenyl, and especially a structure group J- next:
.
wherein: R j and R j, identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl radical, or a phenyl radical; And it designates a radical -CO- or the radical
- n = 0 or 1, it being understood that when n = 1, then U designates the radical -CO-. In structures (I) to (IV) defined above, the alkyl or C1-C4 alkoxy group preferably denotes methyl, ethyl, butyl, methoxy or ethoxy.
The cationic direct dyes of the formulas (I), (II), (III), (III ') which can be used in the dyeing compositions according to the invention are known compounds and are described, for example, in the WO 95/01772, WO 95/15144 and EP-AQ 714 954. The cationic direct dyes of formula (IV) which can be used in the dyeing compositions according to the invention are also known compounds and are described, for example, in patent applications FR-A-2 189 006, FR-A-2 285 851, FR-A-2 140 205 and their certificates of addition. Among the direct cationic dyes of the formula (I) which can be used in the dyeing compositions according to the invention, mention may be made more particularly of "the compounds which respond to the following structures (II) to (152):
7
-
Among the compounds of structures (II) to (152) described above, compounds which respond to structures (II), (12), (114), and (131) are particularly preferred. Among the cationic direct dyes of formula (II) which can be used in the dyeing compositions according to the invention, they can be mentioned more particularly. the compounds that respond to structures (III) to (1112) below:
Cl (111)
CH,
Among the direct cationic dyes of formula (III) which can be used in the dyeing compositions according to the invention, mention may be made in particular of the compounds which respond to the following structures (lili) to (III18):
H3C- N? X ++ X N • CH = N CH3SO4 '(||| 6)
CH = N - - CH3SO4 (11111)
CH.
Among the structure compounds (lili) to (III18) described above, structures (III14), (III15) and (III13) are preferred. Among the direct cationic dyes of formula (III ') which can be used in the dyeing compositions according to the invention, mention may be made more particularly of the compounds which respond to the following structures (III' 1) to (III '3):
Among the direct cationic dyes of formula (IV) which can be used in the dyeing compositions according to the invention, there can be mentioned more particularly the compounds which respond to the structures (IV) __ a (IV) - below:
(IV) 3
CH3SO4"25 CH3SO4" CH3SO4- CH3SO4"CH3SO4" CH3SO4"CH3SO4- CH3SO4" CH3S04"
C4H9 25
CH3SO4
The pyrazolo- [1, 5-a] -pyrimidines of formula (V) according to the invention and / or its or its addition salts with an acid or a base preferably represent from 0.0005 to 12% by weight about the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
The cationic direct dye (s) used according to the invention preferably represent from 0.001 to 10% by weight approximately of the total weight of the dyeing composition and even more preferably from 0.005 to 5% by weight approximately of this weight. The appropriate medium for the dye (or support) is generally constituted by water or by a mixture of water and at least one organic solvent to solubilize the compounds that would not be sufficiently soluble in water. As the organic solvent, there may be mentioned, for example, the alkanols of C _. C4, such as ethanol and isopropanol; 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, analogous products and mixtures thereof. The solvents can be present in proportions preferably comprised 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 composition according to the invention is generally between 3 and 12 DD
approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or alkalizing agents commonly used in dyeing keratin fibers. Among the acidulating agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, acid lactic, sulfonic acids. Among alkalizing agents, mention may be made, by way of example, of ammonia, alkali metal carbonates, alkanolamines talen or mono-, di-triethanolamines, 2-methyl-2-aminopropanol and its derivatives, sodium hydroxides. or of potassium and the following compounds of formula (VIII):
wherein W is a propylene moiety optionally substituted by a hydroxyl group or an alkyl radical of C? -C4; ? _6. R37, R39 and R3 ?. identical or different, represent a hydrogen atom, an alkyl radical of Ci-Ce or hydroxyalkyl of C _.- C0. The dyeing composition according to the invention may also contain one or more couplers which may be selected from the couplers conventionally used in dye by oxidation and among which may be mentioned, in particular, meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers, such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones and their addition salts with an acid. These couplers are chosen more particularly between 2-methyl-5-amino phenol, 5-N- (β-hydroxyethyl) amino-2-methyl phenol, 3-amino phenol, 1,3-dihydroxy benzene, 1,3 -dihydroxy 2-methyl benzene, 4-chloro-1,3-dihydroxy benzene, 2,4-diamino 1- (β-hydroxyethyloxy) benzene, 2-amino 4- (β-hydroxyethylamino) 1-methoxy benzene, 1,3-diamino benzene, 1,3-bis- (2, -diaminophenoxy) propane, sesamol, a-naphthol, 6-hydroxy indole, 4-hydroxy indole, 4-hydroxy N-methyl indole , 6-hydroxy indoline, 2,6-dihydroxy-4-methyl pyridine, lH 3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, and their addition salts with an acid.
When present, these couplers preferably represent from 0.0001 to 10 - by weight approximately of the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately of this weight. The dyeing composition according to the invention can also contain one or more additional oxidation bases other than a pyrazolo- [1,5-a] -pyrimidine and / or even one or more non-cationic direct dyes, in particular for modifying the tones or enriching them in reflexes. Among the additional oxidation bases that can be used in the dyeing compositions according to the invention, mention may be made of para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases. Among the para-phenylenediamines, mention may be made more particularly, by way of example, of para-phenylenediamine, para-tolylene diamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, 2,6-dimethyl paraphenylenediamine and 2,6-diethyl. para-phenylenediamine, 2, 5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N , N-bis- [β-hydroxyethyl) paraphenylenediamine, 4-N, N-bis- (β-hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- (β-hydroxyethyl) amino 2-chlor aniline, 2-β-hydroxyethyl paraphenylenediamine, 2-fluorophenylenediamine, 2-isopropyl paraphenylenediamine, N- (β-hydroxypropyl) paraphenylenediamine, 2-hydroxymethyl paraphenylenediamine, N, -dimethyl 3-methyl paraphenylenediamine, N , N- (ethyl, β-hydroxyethyl) paraphenylenediamine, N- (β, β-dihydroxypropyl) paraphenylenediamine, N- (4'-aminophenyl) paraphenylenediamine, N-phenyl para-phenylenediamine, 2-β-hydroxyethyloxy paraphenylenediamine, 2-β-acetylaminoethyloxy paraphenylenediamine, N- (β-methoxyethyl) paraphenylenediamine, and their addition salts with an acid. Among the para-phenylenediamines mentioned above, para-phenylenediamine, para-tolylenediamine, 2-isopropyl para-phenylenediamine, 2-β-hydroxyethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine, 2,3-, are particularly preferred. dimethyl paraphenylenediamine, N, N-bis-- (β-hydroxyethyl) paraphenylenediamine, 2-chloro paraphenylenediamine, 2-β-acetylaminoethyloxy paraphenylenediamine, and their addition salts with an acid. Among the bis-phenylalkylenediamines, mention may be made more particularly, by way of example, of N, N'-bis- (β-hydroxyethyl) N, '-bis- (4'-aminophenyl) -1,3-diamino propanol, N, N'-bis- (β-hydroxyethyl) N, N'-bis (4'-aminophenyl) ethylenediamine, N, N' -bis- (4-aminophenyl) tetramethylenediamine, N, 'N' -bis- (β-hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methyl) -aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N'-bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis- (2,5-diaminophenoxy) -3,5-dioxaoctane, and its addition salts with an acid. Among the para-aminophenols, mention may be made more particularly, by way of example, of para-aminophenol, 4-amino-3-methyl phenol, 4-amino-3-fluoro-phenol, 4-amino-3-hydroxymethyl-phenol, 4- amino 2-methyl phenol, 4-amino-2-hydroxymethyl phenol, 4-amino-2-methoxymethyl phenol, 4-amino-2-aminomethyl phenol, 4-amino 2- (b-hydroxyethyl aminomethyl) phenol, 4- amino 2-fluorine phenol, and its addition salts with an acid. Among the ortho-aminophenols, mention may be made more particularly, by way of example, of 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, 5-acetamido-2-amino-phenol, and its addition salts with an acid. Among the heterocyclic bases, mention may be made more particularly, by way of example, of pyridine derivatives, pyrimidine derivatives other than the compounds of formula (V) according to the invention, and pyrazole derivatives. Among the pyridine derivatives, mention may be made more particularly of the compounds described, for example, in GB 1 026 978 and GB 1 153 196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine , 2,3-diamino-6-methoxy pyridine, 2 (β-methoxyethyl) amino 6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid. Among the pyrimidine derivatives, there may be mentioned more particularly the compounds described, for example, in German patents DE 2 359 399 or Japanese patents JP 88-169 571 and JP 91-10659 or in patent application WO 96/15765, such as 2, , 5,6-tetra-aminopyrimidine, 4-hydroxy 2, 5,6- triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, and 2, 5 , 6-triaminopyrimidine. Among the pyrazole derivatives, mention may be made more particularly of the compounds described in DE 3 843 892, DE 4 133 957 and in patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 such as 4, 5-diamino-1-methyl pyrazole, 3,4-diamino pyrazole, 4,5-diamino 1- ('-chlorbenzyl) pyrazole, 4,5-diamino-1,3-dimethyl pyrazole, 4,5-diamino-3-methyl-1-phenyl pyrazole, 4,5-diamino-1-methyl-3-phenyl-pyrazole, 4-amino-1,3-dimethyl-5-hydrazine pyrazole, 1-benzyl 4,5- diamino 3-methyl pyrazole, 4,5-diamino 3-tert-butyl 1-methyl pyrazole, 4,5-diamino-1-tert-butyl 3-methyl pyrazole, 4,5-diamino 1- (β-hydroxyethyl) ) 3-methyl pyrazole, 4,5-diamino-1-ethyl-3-methyl pyrazole, 4,5-diamino-1-ethyl 3- (4"-methoxyphenyl) pyrazole, 4,5-diamino-1-ethyl 3- hydroxymethyl pyrazole, 4,5-diamino-3-hydroxymethyl-1-methyl pyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropyl pyrazole, 4,5-diamino-3-methyl-XL-isopropyl pyrazole, 4-amino-5 - (2'-aminoethyl) amino 1, 3-dimethyl pyrazole, 3, 4, 5-triamino pyrazole, 1-methyl 3,4-, 5-triamino pyrazole, 3,5-diamino-1-methyl-4-methylamino pyrazole, 3,5-diamino 4- (β-hydroxyethyl) amino 1-methyl pyrazole, and its addition salts with an acid. When used, these additional oxidation bases 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.
In a general manner, the addition salts with an acid which can be used in the context of the invention (compounds of formula (V), additional oxidation base and couplers) are chosen mainly from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates and acetates. Addition salts with a base which can be used in the context of the dyeing compositions of the invention (compounds of formula (V)) are those obtained in particular with soda, potash, ammonia or amines. The dyeing composition according to the invention may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, non-ionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic, cationic polymers, -ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickeners, such as for example non-ionic guar gums, antioxidant agents, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents, such as for example, volatile or non-volatile silicones, modified or unmodified, smoke-forming agents, ceramides, preserving agents, opacifying agents, it being understood that the technician will endeavor to choose this or these possible complementary compounds in such a way that the advantageous properties intrinsically fixed to the dyeing composition of oxidation dye are not substantially altered by the addition or additions considered. The dyeing composition according to the invention can be presented in various forms, such as in the form of liquids, powders, creams, gels, or in any other form suitable for dyeing the keratin fibers, and mainly the human hair. The subject of the invention is also a dyeing process for keratin fibers and in particular for human keratin fibers such as hair, which employs the dyeing composition as defined above. According to this method, at least one dye composition is applied to the fibers, as defined above, the color being developed with acid, neutral or alkaline pH with the aid of a non-enzymatic oxidizing agent that is added just at the time of use to the dye composition or that is present in an oxidizing composition applied simultaneously or sequentially. According to a preferred embodiment of the dyeing process of the invention, the dyeing composition described above is preferably mixed, at the time of use, with an oxidizing composition containing, in a medium suitable for dyeing, at least one non-oxidizing agent. enzyme present in an amount sufficient to develop a coloration. The mixture obtained is then applied to the keratin fibers and left to stand for about 3 to 50 minutes, preferably about 5 to 30 minutes, after which it is rinsed, washed with shampoo, rinsed again and dried. The oxidizing agent present in the oxidizing composition, as defined above, can be chosen from the oxidizing agents conventionally used for dyeing by oxidation of the keratin fibers, and among which may be mentioned hydrogen peroxide, urea peroxide, alkali metal bromates, peracids and persalts, such as perborates and persulfates. Particularly preferred is hydrogen peroxide. The pH of the oxidizing composition containing the oxidizing agent as defined above is such that, after mixing with the dyeing composition, the pH of the resulting composition applied to the keratin fibers preferably ranges from about 3 to about 12, and even more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or alkalizing agents usually used in dyeing the keratin fibers and as defined above. The oxidizing composition as defined above may also contain 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 in the form of liquids, creams, gels, or in any other form suitable for dyeing the keratin fibers, and mainly the human hair. Another object of the invention is a multi-compartment dye kit or any other multi-compartment conditioning system, which first compartment contains the dye composition, as defined above and a second compartment contains the oxidizing composition, as defined above. These devices may be equipped with a means for supplying the desired mixture on the hair, such as the devices described in patent FR-2 586 913 in the name of the Applicant Firm. The following example is intended to illustrate the invention without, however, presenting a limiting character.
EXAMPLE OF DYEING IN ALKALINE MEDIUM The following dyeing composition according to the invention was prepared: - Pirazolo [1, 5-a "] -pyrimidine-3,7-diamine, 2HC1 (oxidation base) 0.333 g
- Direct cationic dye of formula 112] i g
- Ethyl alcohol 96 ° 18 g
- Pentasodic salt of diethylenetriamine pentacetic acid 1.1 g
- Ammonia at 20 ° of NH3 10.0 g
- Demineralized water esp 100 g At the time of use, the previous dye composition was mixed weight by weight with a solution of hydrogen peroxide with 20 volumes (6 - by weight) of pH 3. The obtained mixture was applied on hair strands natural grays with 90% white for 30 minutes. The wicks were then rinsed, washed with a standard shampoo, rinsed again, then dried. The hair was stained in an intense fuchsia shade. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects or products to which it refers.
Claims (22)
1. Composition for dyeing by oxidation of keratin fibers, and in particular of human keratin fibers such as hair, characterized in that it contains, in an appropriate medium for dyeing: - at least one pyrazolo- [1, 5] -a] -pyrimidine as oxidation base; - and at least one direct cationic dye; said composition being exempt from any enzymatic system capable of causing the oxidation of the pyrazolo- [1, 5-a] -pyrimidines.
2. Composition according to claim 1, characterized in that the pyrazolo- [1, 5-a] -pyrimidines are chosen from the following compounds of formula (V) and • their addition salts with an acid or with a base; where: R33, R3, R3? and R3i designate, identical or different, a hydrogen atom, an alkyl radical of C? -C4, an aryl radical, a hydroxyalkyl radical of C? C4, a polyhydroxyalkyl radical of C -C ^, a radical (C1-C4) alkoxy C: -C4 alkyl, an amino radical of C1-C4 alkyl (the amine may be protected by an acetyl, a ureide, a sulfonyl) , a radical (C.-Cs) alkylamino alkyl of C _. C, a radical di - [(C; -C alkyl] amino C 1 -C 4 alkyl (the dialkyls may form an aliphatic or heterocyclic ring with 5 or 6 links), a hydroxy radical (C1-C4) alkyl- or di- [hydroxy (C1-C4) alkyl] -amino alkyl (C; -C); - R radicals, identical or different, denote a hydrogen atom, a C 1 -C 4 alkyl radical, an aryl radical, a hydroxyalkyl radical of C _ -C 4, a polyhydroxyalkyl radical of C _ - C 4, a radical (C? -C4) alkylamino C 1 -C 4 alkyl / a di- [(C 1 -C 4) alkyl] amino] C 1 -C 4 alkyl radical (the dialkyls can form an aliphatic or heterocyclic cycle with 5 or 6 links), a hydroxy radical ( C1-C4) alkyl or di- [hydroxy (C:-C4) alkyl] amino C 1 -C 4 alkyl / an amino radical, a radical (C: -C 4) alkyl di [(C ..- C.) Alkyl ] -Not me; a halogen atom, a carboxylic acid group, a sulfonic acid group; - i is worth 0, 1, 2 or 3 here; - p is worth 0 or 1 here; - that is worth 0 or 1 here; - n is worth 0 or 1 here; with the proviso that: - (i) the sum p + q is different from 0; - (ii) when p + q equals 2, then n is 0 and the groups NR .R ^, and NRjeRJ occupy the positions (2, 3); (5, 6); (6, 7); (3, 5) or (3,7); - (iii) when p + q is equal to 1, then n is worth 1 and the group NRj3R¿ (or NRasR ^ ,.) and the group OH occupy the positions (2, 3); (5, 6); (6, 7); (3, 5) or (3, 7).
3. Composition according to claim 2, characterized in that the pyrazolo- [1, 5-a] -pyrimidines of the formula (V) are chosen from: - the pyrazolo- [1,5-a] -pyrimidine- 3, 7-diamine; - 2-methyl pyrazolo- [1,5-a] -pyrimidin-3,7-diamine; - 2,5-dimethylpyrazolo- [1,5-a] -pyrimidin-3,7-diamine; - pyrazolo- [1, 5-a] -pyrimidin-3, 5-diamine; - 2,7-dimethylpyrazolo- [1, 5-a] -pyrimidin-3,5-diamine; - 3-amino pyrazolo- [1,5-a] -pyrimidin-7-ol; - 3-amino-5-methyl pyrazolo- [1, 5-a] -pyrimidin-7-ol; - 3-amino-5-methyl-7-imidazolylpropylamino pyrazole- [1,5-a] -pyrmidine; - 3-amino pyrazolo- [1, 5-a] -pyrimidin-5-ol; - 2- (3-amino pyrazolo- [1,5-a] -pyrimidin-7-yl) ethanol; - 3-amino-7-β-hydroxyethylamino-5-methyl-pyrazolo- [1,5-a] -pyrimidine; - 2- ("7-amino pyrazolo- [1, 5-a] -pyrimidin-3-ylamino) -ethanol; - 2- [(3-amino-pyrazolo- [1, 5-a] -pyrimidine- 7-yl) - (2-hydroxyethyl) -amino] -ethanol, 2- [7-amino pyrazolo- [1,5-a] -pyrimidin-3-yl) - (2-hydroxyethyl) -amino] -ethanol; - 5,6-dimethylpyrazolo- [1,5-a] -pyrimidin-3,7-diamine; - 2,6-dimethylpyrazolo- [1,5-a] -pyrimidin-3,7-diamine; the 2,5, N-7, 'N-7-tetramethyl pyrazolo- [1,5-a] -pyrimidin-3,7-diamine and its addition salts with an acid or with a base.
4. Composition according to any of the preceding claims, characterized in that the direct cationic dye (s) are chosen from cationic anthraquinones, cationic mono- or di-azoics, and cationic naphthoquinones.
5. Composition according to claim 4, characterized in that the cationic dyes are chosen from [8- [(p-aminophenyl) azol] -7-hydroxy-2-naphthyl] trimethylammonium chloride, the combination of the 3- [(4-amino-6-bromo-5,8-dihydro-l-hydroxy-8-imino-5-oxo-2-naphthalenyl) -amino] -N, N, N-trimethylbenzenamine and chloride " 3- [(2,6-dibromo-5,8-dihydro-l-hydroxy-8-imino-5-oxo-3-naphthyl) -amino] -N, N, N-trimethylbenzenamine, 7-hydroxy chloride -8- [(2-methoxy phenyl) azo] -N,, N-trimeti 1-2-naphthalene inium, [8- [(4-amino-2-nitrophenyl) azo] -7-hydroxy-2 chloride -naphthyl] trimethylammonium, the association of [8- [(4-amino-3-nitrophenyl) azo] -7-hydroxy-2-naphthyl] trimethylammonium chloride and [8- [(4-amino-2- nitrophenyl) azo] -7-hydroxy-2-naphthyl] trimethylammonium chloride, 3- [4,5-dihydro-3-methyl-5-oxo-l-phenyl-lH-pyrazol-4-yl] -zo] chloride] N, N, N-trimethyl-benzenamine, 1- (α-aminopropyl) amino hydrochloride anthraquinone, 1-N- (methyl-morpholinium-propyl) amino-4-hydroxy anthraquinone methylisulfate, and Basic Orange 69®.
6. Composition according to any of claims 1 to 3, characterized in that the dye (s) are chosen from the compounds of the formulas (I), (II), (III), (III '), and (IV) ) following: a) compounds of the formula (I): in which D represents a nitrogen atom or the group -CH, - Ri and Re, identical or different, represents a hydrogen atom; an alkyl radical of C? -C2 which can be substituted by a radical -CN, OH or -NH2 or form with a carbon atom of the benzene ring a heterocycle optionally oxygenated or nitrogenated, which can be substituted by one or more alkyl radicals of C -__Cz, a 4'-amino-phenyl radical, - R3 and R'3 / identical or different, represents a hydrogen atom or a halogen chosen from chlorine, bromine, iodine, fluorine, a cyano radical, Ci-C4 alkoxy or acetyloxy, - X ~ represents an anion preferably chosen from chloride, methyl sulfate and acetate, -A represents a group chosen by the following structures Al a Al 9: * 2 -A, AT A .. 12 .0 A ".5 Aie .7 .8 wherein R 4 represents a C 1 -C 4 alkyl radical which may be substituted by a hydroxyl and R 5 represents an alkoxy radical of C _ -C 4, except that when D represents -CH, when A represents A4 or Au and when Rj is different from an alkoxy radical, then R \ and R_ do not simultaneously designate a hydrogen atom; b) compounds of formula (II) wherein: R. represents a hydrogen atom or an alkyl radical of Ci-C .., RT represents a hydrogen atom, an alkyl radical, which may be substituted by a -CN radical or by an amino group, an 4'-Amino-phenyl radical or form with R "a possibly oxygenated and / or nitrogenated heterocycle which may be substituted by an alkyl radical of C? -C4 / - Re and R5 / identical or different, represent a hydrogen atom, an atom of halogen, such as bromine, chlorine, iodine and / or fluorine, an alkyl radical of C-C4 or C1-C4 alkoxy, a -CN radical, - X ~ represents an anion preferably chosen from chloride, methyl sulfate and acetate. - B represents a group chosen from the following structures Bl to B6: B1 B4 B5 B6 wherein R _.,; represents an alkyl radical of C 1 -C 4, R: and R 12, identical or different, represent a hydrogen atom or an alkyl radical of C _ -C; c) compounds of the formula (III) and (III '): wherein: - R13 represents a hydrogen atom, a C1-C4 alkoxy radical, a halogen atom, such as bromine, chlorine, iodine or fluorine or an amino radical, - RIÍ represents a hydrogen atom , an alkyl radical of C _. C4, or form with a carbon atom of the benzene ring a heterocycle optionally oxygen and / or substituted by one or more alkyl groups of C: - C <; - Ris represents a hydrogen or halogen atom, such as bromine, chlorine, iodine or fluorine, - Ris and R? T, identical or different, represent a hydrogen atom or an alkyl radical of C? ~ C4, - Di and D;, identical or different, represent a nitrogen atom or the group -CH, - m = 0 or 1 with the understanding that when R1 represents an unsubstituted amino group, then Di and D2 represent simultaneously group -CH and m = 0, - X ~ represents an anion preferably chosen from chloride, methyl sulfate and acetate, - E represents a group chosen by the structures Ei a E. following: E1 E6 E7 E8 wherein R 'represents an alkyl radical of C.-Cj; when m = 0 and when D: represents a nitrogen atom, then E may also designate a group of structure E9 below: wherein R 'represents an alkyl radical of C? -C4. By one or several C1-C4 alkyl radicals, C1-C4 alkoxy, or N0¿ or together with G2 form a benzene ring optionally substituted by one or more C rad-CH alkyl radicals, C: -C 4 alkoxy or NO_; R_ can also designate a hydrogen atom; Z designates an oxygen atom, a sulfur atom or a group -NR 5; - M represents a group -CH, -CR "(designating R" C: -C4 alkyl), or -NR :; (X ") r; K represents a group -CH, -CR" (denoting R "C alquilo-C4 alkyl) or -NR :: (X ~) r; P represents a group -CH, -CR" (designating R "Ci-Cj alkyl), o-NR: :( X") r; r designates zero or 1; Rzi represents a 0"atom, a C 1 -C 4 alkoxy radical, or a C 1 -C 4 alkyl radical: R 3 and R 4, which are identical or different, represent a hydrogen or halogen atom chosen from chlorine, bromine, iodine and fluorine, an alkyl radical of C? C4, C1-C4 alkoxy, a radical -NO ..; X ~ represents an anion preferably chosen from chloride, iodide, methyl sulfate, etiisulfate, acetate and perchlorate; with the proviso that: when R__ designates O "then r designates zero; d) compounds of formula (IV) N = N J (IV) where - G represents a group chosen from the following G_ to G¿ structures: wherein: R? _ designates a C? -C4 alkyl radical, a phenyl radical, a phenyl radical substituted by a C1-C alkyl radical, or a halogen atom chosen from chlorine, bromine, iodine and fluoride; Ria denotes a C 1 -C 4 alkyl radical or a phenyl radical; R2; and R2 ?, identical or different, represent an alkyl radical of C? -C4 a phenyl radical, or together with Gi form a benzene ring substituted by one or more C1-C4 alkyl radicals, Ci- C4 alkoxy, or N0_ or together with G, they form a benzene ring optionally substituted by one or more C rad-C4 alkyl radicals / C?-C or NO- alkoxy; R_.o may also designate a hydrogen atom; - When K designates -NR: (X ~) r, then M = P = -CH or -CR "; when M designates -NR _._. (X") r, then K = P = -CH or -CR "; when P designates -NR (X") r; then K = M and designate -CH or -CR; when Z designates a sulfur atom and R: designates an alkyl radical of C? -C4, then R;, -, is different from a hydrogen atom; when Z designates -NR, and when Ri9 designates an alkyl radical of C _-C4 / then at least one of the radicals R? 8, Ris or R_.0 of the group of structure G__ ea different from an alkyl radical of C: -C4; J represents: • or a group of structure J-, following: wherein: R 25 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, an alkyl radical of C _ - Cj, C 4 C alkoxy, a -OH radical, -NO :, -NHR S, -NR__9R3o / -NHCOalkyl of C? -C4, or form with R? 6 a 5 or 6 membered chain containing or not one or more heteroatoms chosen from nitrogen, oxygen and sulfur; R26 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, an alkyl radical of C: -C4, C: ~ C4 alkoxy, or forms with R0 a cycle of 5; or 6 links, which contains or not one or more heteroatoms chosen from nitrogen, oxygen or sulfur; R2t represents a hydrogen atom, a -OH radical, a -NHR26 / radical or a -NR: aR radical; R2e represents a hydrogen atom, an alkyl radical of C? -C4, a monohydroxyalkyl radical of C? -C / polyhydroxyalkyl of C: ~ C4 or a phenyl radical; R_9 and R_o. identical or different, represent an alkyl radical of C? -C4, a monohydroxyalkyl radical of C? -C4 / or polyhydroxyalkyl of C_-C4; or a 5- or 6-membered nitrogenous heterocyclic group capable of containing other heteroatoms and / or carbonized groups and which may be substituted by one or more C?-C, amino or phenyl alkyl radicals, and especially a group of structure J 2 following : wherein: R and R;, identical or different, represent a hydrogen atom, an alkyl radical of C- ± d, or a phenyl radical; - Y designates a radical -CO- or the radical CH,; n = 0 or 1, it being understood that when n = 1, then U designates the radical -C0-.
7. Composition according to claim 6, characterized by; the fact that the cationic direct dyes of formula (I) are chosen from the compounds that respond to the following structures (II) to (152): CH, / - N + W -CH: CH-. { . • N Cl "(16) HO-H4C \ CH, CH, . • , Y
8. Composition according to claim 6, characterized in that the direct cationic dyes of formula (II) are chosen from the compounds that respond to structures (III) to (1112) below: Cl (II2) (2UI)? OS? O Lß
9. Composition according to claim 6, characterized in that the cationic direct dyes of formula (III) are chosen from the compounds that respond to the following structures (lili) to (III18): OCH. Cl (1115) CH-
10. Composition according to claim 6, characterized in that the cationic direct dyes of formula (III ') are chosen from the compounds that respond to the following structures (III'l) to (III'3) :
11. Composition according to claim 6, characterized in that the direct cationic dyes of formula (IV) are chosen from the compounds that respond to the structures (IV); a (IV) - following: 25 (iv) «l_ O CH3S04- 25 CH3S04- CH3SO4" CH3SO4- CH3SO4- CH3SO4- CH3SO4- CH3S04- CH3SO4" 25 C4H9 10
12. Composition according to any of the preceding claims characterized in that the pyrazolo- [1,5-a] pyrimidines and / or its or its addition salts with an acid or a base represent 0.0005 a 12% by weight of the total weight of the dye composition.
13. Composition according to claim 12, characterized in that the pyrazolo- [1,5-a) -pyrimidines and / or the one or more addition salts thereof with an acid or with a base represent from 0.005 to 6% by weight of the total weight of the dye composition.
14. Composition according to any of the preceding claims, characterized in that the cationic direct dye (s) represent from 0.001 to 10% by weight of the total weight of the dye composition.
15. Composition according to claim 14, characterized in that the cationic direct dye (s) represent from 0.005 to 5% by weight of the total weight of the dyeing composition.
16. Composition according to any of the preceding claims, characterized in that it contains one or more couplers chosen from metaphenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers, such as indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.
17. Composition according to any of the preceding claims, characterized in that it contains one or more additional oxidation bases other than a pyrazolo- [1,5-a] -pyrimidine and / or one or more non-cationic direct dyes.
18. Composition according to claim 17, characterized in that the additional oxidation base (s) are chosen from paraphenylenediamines, bis-phenylalkylenediamines, para-aminopheols, ortho-aminophenols and heterocyclic bases.
19. Composition according to any of the preceding claims, characterized in that the addition salts with an acid are chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates and acetates, and because the addition salts with a base are chosen from those obtained with soda, potash, ammonia or amines.
20. Dyeing process by oxidation of keratin fibers and in particular of human keratin fibers such as hair characterized in that at least one dye composition as defined in any of claims 1 to 19 is applied to said fibers. , and in that the color is revealed with an acidic, neutral or alkaline pH with the aid of a non-enzymatic oxidizing agent, which is added just at the time of use to the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially. '
21. Process according to claim 20, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, peracids and persalts.
22. Device with several compartments or dye "kit" with several compartments, whose first compartment contains a dye composition as defined in any of claims 1 to 19, and a second compartment containing an oxidizing composition containing an oxidizing agent not enzymatic
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9813866A FR2785183B1 (en) | 1998-11-04 | 1998-11-04 | TINCTORIAL COMPOSITION CONTAINING CATIONIC DIRECT DYE AND PYRAZOLO- [1,5-a] - PYRIMIDINE AS OXIDATION BASE, AND DYEING METHODS |
FR9813866 | 1998-11-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
MX9910062A MX9910062A (en) | 2000-09-01 |
MXPA99010062A true MXPA99010062A (en) | 2000-12-06 |
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