AU5600699A - Dye composition containing a cationic direct dye and a pyrazolo(1,5-a)pyrimidine as oxidation base, and dyeing processes - Google Patents
Dye composition containing a cationic direct dye and a pyrazolo(1,5-a)pyrimidine as oxidation base, and dyeing processes Download PDFInfo
- Publication number
- AU5600699A AU5600699A AU56006/99A AU5600699A AU5600699A AU 5600699 A AU5600699 A AU 5600699A AU 56006/99 A AU56006/99 A AU 56006/99A AU 5600699 A AU5600699 A AU 5600699A AU 5600699 A AU5600699 A AU 5600699A
- Authority
- AU
- Australia
- Prior art keywords
- radical
- alkyl
- chosen
- amino
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims description 87
- 239000000975 dye Substances 0.000 title claims description 50
- 125000002091 cationic group Chemical group 0.000 title claims description 32
- 239000000982 direct dye Substances 0.000 title claims description 29
- 238000004043 dyeing Methods 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 11
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 title claims description 8
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title claims description 3
- -1 hydroxyalkyl radical Chemical class 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 150000003254 radicals Chemical class 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 29
- 230000003647 oxidation Effects 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000002585 base Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 102000011782 Keratins Human genes 0.000 claims description 20
- 108010076876 Keratins Proteins 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 210000004209 hair Anatomy 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 239000011630 iodine Substances 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 230000001590 oxidative effect Effects 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 3
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 229930192627 Naphthoquinone Natural products 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- YLPWLSGBUJBSCK-UHFFFAOYSA-M [3-[(4-amino-2,5-dimethoxyphenyl)diazenyl]phenyl]-trimethylazanium;chloride Chemical compound [Cl-].C1=C(N)C(OC)=CC(N=NC=2C=C(C=CC=2)[N+](C)(C)C)=C1OC YLPWLSGBUJBSCK-UHFFFAOYSA-M 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
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 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
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 101100327795 Penaeus monodon CHH3 gene Proteins 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- FVUJPXXDENYILK-WITUOYQCSA-N (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[2-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoic acid Chemical compound CC(C)C[C@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)Cc1cnc[nH]1)[C@@H](C)O)[C@@H](C)O)C(=O)N[C@@H](C(C)C)C(N)=O FVUJPXXDENYILK-WITUOYQCSA-N 0.000 claims 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims 1
- VVGUYQQABCAGFN-UHFFFAOYSA-N 2,6-dimethyl-1h-pyrazolo[4,3-d]pyrimidine-3,7-diamine Chemical compound CN1C=NC2=C(N)N(C)NC2=C1N VVGUYQQABCAGFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 208000013840 Non-involuting congenital hemangioma Diseases 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 101150024084 nhr-28 gene Proteins 0.000 claims 1
- 239000004071 soot Substances 0.000 claims 1
- 108700043117 vasectrin I Proteins 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000003230 pyrimidines Chemical class 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 239000002535 acidifier Substances 0.000 description 3
- 239000002610 basifying agent Substances 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
- 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
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XNQCXEBZBVDKAL-UHFFFAOYSA-N OSSS Chemical compound OSSS XNQCXEBZBVDKAL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)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 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- DWKARHJHPSUOBW-UHFFFAOYSA-N trimethyl-[3-[(2e)-2-(3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)hydrazinyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(O)=C1N=NC1=CC=CC([N+](C)(C)C)=C1 DWKARHJHPSUOBW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-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
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- KQGOJGSMIRVVJL-UHFFFAOYSA-N 1-n-methyl-4-n-[4-[4-(methylamino)anilino]butyl]benzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1NCCCCNC1=CC=C(NC)C=C1 KQGOJGSMIRVVJL-UHFFFAOYSA-N 0.000 description 1
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- YTEVZALKGJZUFD-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,7-diamine;dihydrochloride Chemical compound Cl.Cl.NC1=CC=NC2=C(N)C=NN21 YTEVZALKGJZUFD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
Description
T
AUSTRALIA
Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Applicant(s):
L'OREAL
r r r r Invention Title: DYE COMPOSITION CONTAINING A CATIONIC DIRECT DYE AND A PYRIMIDINE AS OXIDATION BASE, AND DYEING
PROCESSES
The following statement is a full description of this invention, including the best method of performing it known to me/us: The invention relates to a composition for the oxidation dyeing of keratin fibres, containing at least one cationic direct dye and at least one as oxidation base, as well as to the oxidation dyeing process using this composition.
It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or paraaminophenols, bis(phenyl)alkylenediamines or heterocyclic compounds, which are generally referred to as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, 15 can give rise to coloured compounds and dyes by a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as regards the oxidation bases and the couplers allows a wide range of colours to be obtained.
2 The so-called "permanent" coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus it must have no toxicological drawbacks, it must be able to give shades of the desired intensity and it must be able to withstand external agents (light, bad weather, washing, permanent-waving, perspiration, rubbing).
The dyes must also be able to cover white hair and, lastly, they must be as unselective as possible, i.e. they must give the smallest possible coloration differences along the same length of keratin fibre, which may in fact be differently sensitized damaged) between its tip and its root.
It is has already been proposed, in 15 particular in patent application FR-A-2,750,048, to use as oxidation bases, alone or in combination .with one or more couplers. However, the colorations obtained are not always sufficiently intense, chromatic or resistant to the various attacking factors to which the hair may be subjected.
The Applicant has now discovered, entirely surprisingly and unexpectedly, that the combination of at least one pyrazololl,5-a]pyrimidine as oxidation base and at least one cationic direct dye defined below makes it possible to obtain intense colorations which moreover have improved properties of resistance with 3 respect to the various attacking factors to which the hair may be subjected (shampoo, light, bad weather, permanent-waving, perspiration, rubbing, etc.).
These discoveries form the basis of the present .invention.
A first subject of the invention is thus a composition for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, characterized -in that it contains, in a medium which is suitable for dyeing: at least one pyrazolo[1,5-a]pyrimidine as oxidation base; and at least one cationic direct dye; the said composition being free of any enzymatic system S. 15 capable of bringing about the oxidation of the pyrazolo(1i, As indicated above, the dye composition in accordance with the invention leads to intense colorations which moreover have excellent properties of resistance with respect to the action of various external agents (light, bad weather, washing, permanent-waving, perspiration and rubbing).
A subject of the invention is also a process for the oxidation dyeing of keratin fibres using this dye composition.
The pyrazolo[l,5-a]pyrimidines which can be used as oxidation bases in the dye composition in accordance with the invention are preferably chosen from the compounds of formula below, and the addition salts thereof with an acid or with a base: 3 [NR 33 Rp 7 [N R3R q in which:
R
33
R
34
R
35 and R 36 which may be identical or different, denote a hydrogen atom, a Ci-C 4 alkyl 0 radical, an aryl radical, a Ci-C 4 hydroxyalkyl radical, a C 2
-C
4 polyhydroxyalkyl radical, a (Ci-C 4 )alkoxyo (Ci-C 4 )alkyl. radical, a Ci-C 4 aminoalkyl radical (it being possible for the amine to be protected with an acetyl, ureido or sulphonyl radical), a (C-C 4 )alkylamino (Ci-C 4 )alkyl radical, a di[ (Ci-C 4 )alkyl]amino- (Ci-C 4 )alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered aliphatic or heterocyclic ring), a hydroxy(C 1
-C
4 )alkyl- or di[hydroxy- (Ci-C4)alkyl]amino (C-C 4 alkyl radical; the radicals R, which may be identical or different, denote a hydrogen atom, a Ci-C 4 alkyl radical, an aryl radical, a Ci-C 4 hydroxyalkyl radical, a C 2
-C
4 polyhydroxyalkyl radical, a Ci-C 4 aminoalkyl radical, a
(C
1
-C
4 alkylamino(Ci-C 4 alkyl radical, a di (C-C 4 )alkyl] amino(Ci-C 4 alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered aliphatic or heterocyclic ring), a hydroxy(C 1
-C
4 )alkylor di[hydroxy(C-C 4 alkyl]amino(C 1
-C
4 alkyl radical, an amino radical, a (C 1
-C
4 )alkyl- or di[ (C-C 4 )alkyl]amino radical; a halogen atom, a carboxylic acid group or a sulphonic acid group; i is equal to 0, 1, 2 or 3; p is equal to 0 or 1; q is equal to 0 or 1; n is equal to 0 or 1; with the proviso that: the sum p q is other than 0; 15 (ii) when p q is equal to 2, then n is equal to 0 and the groups NR 33
R
34 and NR3sR 36 occupy the or positions; (iii) when p q is equal to 1, then n is equal to 1 and the group NR 33
R
34 (or NR 35
R
36 and the OH group occupy the or (3,7) positions.
The pyrazolo[l,5-a]pyrimidines of formula (V) above are known compounds which are described in particular in patent application FR-A-2,750,048, the content of which forms an integral part of the present patent application.
Among the pyrazolo(1,5-alpyrimidines of formula (V which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made in particular of: pyrazolo[1,5-alpyrimidine-3,7-diamine; 2-methylpyrazolo[1,5-alpyrinidine-3,7-dianine; 2,5-dimethylpyrazolo(1,5-alpyrimidine-3,7-dianine; pyrazolo 5-a]pyrimidine-3, 2,7-dimethylpyrazolo 5-alpyrimidine-3, 3-aininopyrazolo(l, 5-alpyrimidin-7-ol; 3-amino-5-methylpyrazolo(l,5-alpyrimidin-7-ol; 3-aminopyrazoloti, 2- (3-aiinopyrazolofi, 5-alpyrimidin-7-ylamino) ethanol; 3-axnino-7-j-hydroxyethylamino-5-methylpyrazolo- 15 3 -amino-5-methyl-7-imidazolylpropylamiflo pyrazolo- -pyrimidine; 2- (7-aminopyrazolo 5-a]pyrimidin-3-ylanino) ethanol; -2-f (3-aminopyrazoloEl, 5-alpyrimidin-7-yl)-(2-hydroxyethyl) amino] ethanol; (7-aminopyrazolofl,5-alpyrimidin-3-yl)-(2-hydroxy- .:ethyl) amino]I ethanol; 5,6-~dimethylpyrazolo[1,5-alpyrimidine-3,7-diaine; 2,6-dimethylpyrazolo[1,5-alpyrimidine-3,7-diamine; 2,5,N7,N7-tetramethylpyrazolo[1,5-alpyrimidine-3, 7 diarnine; and the addition salts thereof with an acid or with a base.
7 The cationic direct dye(s) which can be used in the dye composition in accordance with the invention is (are) preferably chosen from cationic aminoanthraquinones, cationic mono- or diazo compounds and cationic naphthoquinones.
As examples, mention may be made in particular of [8-f(p-aminophenyl)azo]-7-hydroxy- 2-naphthyl]trimethylammonium chloride (also known as Basic Brown 16® or Arianor Mahogany 3060020 in the Color Index), the combination of 3-U 4-amino-6-bromo- 5,8-dihydro-l-hydroxy-8-imino-5-oxo-2-naphthyl)amino]- N,N,N-trimethylbenzenaminium chloride and of 3-f(2,6-dibromo-5,8-dihydro-l-hydroxy-8-imino-5-oxo- 3-naphthyl) amino] -N,N,N-trimethylbenzenaminium chloride 15 (also known as Basic Blue 99@ or Arianor Steel Blue 3060040 in the Color Index), 7-hydroxy-8- (2-methoxyphenyl)azo]-N,N,N-trimethyl-2-naphthalenaminium chloride (also known as Basic Red 760 or Arianor Madder Red® in the Color Index), [8-[(4-amino-2-nltrophenyl)azo]-7-hydroxy-2-naphthyl trimethylaznuoniun chloride (also known as Basic Red 118@ or Arianor Bordeaux 3060060 in the Color Index), the combination of amino-3-nitrophenyl) azo] -7-hydroxy-2-naphthyl] trimethylammonium chloride and of (8-[(4-amino-2-nitrophenyl) azo] -7-hydroxy-2-naphthyl] trimethylanmonium chloride (also known as Basic Brown 17® or Arianor Sienna Brown 306001® in the Color Index), dihydro-3-methyl-5-oxo-l-phenyl-1H-pyrazol-4-yl)azo]- N,N,N-trimethylbenzenaminium chloride (also known as Basic Yellow 57® or Arianor Straw Yellow 306005® in the Color Index), 1-(y-aminopropyl)aminoanthraquinone hydrochloride, 1-N-(methylmorpholiniumpropyl)amino-4hydroxyanthraquinone methyl sulphate and Basic Orange 69® (Color Index name).
The cationic direct dye(s) used in the dye composition in accordance with the invention can also be chosen from the compounds of formulae (II), (III), (III') and (IV) below: a) compounds of formula
R,
IR
which: S- D represents a nitrogen atom or a -CH group,
R
1 and R 2 which may be identical or. different, represent a hydrogen atom; a C 1
-C
4 alkyl radical which can be substituted with a -CN, -OH or -NH 2 radical or form, with a carbon atom of the benzene ring, a heterocycle optionally containing oxygen or nitrogen, which can be substituted with one or more CI-C 4 alkyl radicals; a 4'-aminophenyl radical,
R
3 and R' 3 which may be identical or different, represent a hydrogen atom or a halogen atom chosen from chlorine, bromine, iodine and fluorine, or a cyano,
C
1
-C
4 alkoxy or acetyloxy radical, X" represents an anion preferably chosen from chloride, methyl sulphate and acetate, A represents a group chosen from structures Ai to A 19 below:
S
OSSS
S
S S 0 see C C
S.
S
*F S
I
A,
x
+N
R4
A
2 ,4
N-N+
SR4 N
R-N
N
R4
A
3 ,R4 N-N
I
R4
A
R
4
,R
4 R4
A,
RN
R4
A
8
R
4 4 R N R4
A
/R4 R4
IN=N+
C .NR4R6-0
A
1 0 All A 12 R4 R 4 /I NN
N+
R4 S
S
A
1 3
A
1 4 A 1 R
R
I- N R4' N SN S.I A 1 6 A 17 A 18 :and
N
in wichR4 eprsens aCl-C 4 alkyl radical which can be substituted with a hydroxyl radical and R 5 represents a Cl-C 4 alkoxy radical, with the proviso that when D represents -CH, A represents A 4 or A 13 and R 3 is other 11 than an alkoxy radical, then Ri and R 2 do not simultaneously denote a hydrogen atom; b) compounds of formula (II):
R
8 B-N=N N (II) R6
X
R
9 in which:
R
6 represents a hydrogen atom or a Ci-C 4 alkyl radical,
R
7 represents a hydrogen atom, an alkyl radical which can be substituted with a -CN radical or with an amino group, a 4'-aminophenyl radical or forms with R 6 a heterocycle, optionally containing oxygen and/or nitrogen, which can be substituted with a CI-C 4 alkyl radical,
R
8 and R 9 which may be identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine or fluorine, a Ci-C 4 alkyl or
C
1
-C
4 alkoxy radical or a -CN radical, X represents an anion preferably chosen from chloride, methyl sulphate and acetate, 20 B represents a group chosen from structures B1 to B6 below: Rio- Ro N-N-- I R S Ro
N-N+
R N S
R
12 I
R-N+
N
R Rio and
'S
Nw in which Rio represents a C 1
-C
4 alkyl radical and R 11 and
R
12 which may be identical or different, represent a hydrogen atom or a Ci-C 4 alkyl radical; C) compounds of formulae (III) and (III'):
(III')
in which:
R
13 represents a hydrogen atom, a C 1
-C
4 alkoxy radical, a halogen atom such as bromine, chlorine, iodine or fluorine or an amino radical, 1 13
R
14 represents a hydrogen atom, a Ci-C 4 alkyl radical or forms, with a carbon atom of the benzene ring, a heterocycle optionally containing oxygen and/or substituted with one or more Ci-C 4 alkyl groups,
R
15 represents a hydrogen atom or a halogen atom such as bromine, chlorine, iodine or fluorine,
R
16 and R 17 which may be identical or different, represent a hydrogen atom or a Ci-C 4 alkyl radical,
D
1 and D 2 which may be identical or different, represent a nitrogen atom or a -CH group, m 0 or 1, it being understood that when Ri3 represents an unsubstituted amino group, then Di and D 2 simultaneously represent a -CH group and m 0, X- represents an anion preferably chosen from chloride, methyl sulphate and acetate, E represents a group chosen from structures El to E8 below: f
R-N
El E2
E
E3 0 R' R' E4N N E4 and in which R' represents a Ci-C 4 alkyl radical; when m 0 and D 1 represents a nitrogen atom, then E can also denote a group of structure E9 below:
R'
N
R'
in which R' represents a Ci-C 4 alkyl radical; d) compounds of formula (IV): G-N=N J
(IV)
in which G represents a group chosen from structures GI to G 3 below:
R
2 0 R1 0 R
R
1 NR N RMP X19 X
M
R1 8 R1, G, G2 G3 in which:
R
18 denotes a Ci-C 4 alkyl radical, a phenyl radical, a phenyl radical substituted with a CI-C 4 alkyl radical or a halogen atom chosen from chlorine, bromine, iodine and fluorine;
R
19 denotes a Ci-C 4 alkyl radical or a phenyl radical;
R
20 and R 21 which may be identical or different, represent a C 1
-C
4 alkyl radical, a phenyl radical or together form, in GI, a benzene ring substituted with one or more Ci-C 4 alkyl, Ci-C 4 alkoxy or NO 2 radicals, or together form, in G 2 a benzene ring optionally substituted with one or more Ci-C 4 alkyl, Ci-C 4 alkoxy or
NO
2 radicals; R 20 can also denote a hydrogen atom; Z denotes an oxygen or sulphur atom or a group -NR 19 M represents a -CH, -CR" denoting CI-C 4 alkyl) or -NR22(X) r group; K represents a -CH, -CR" denoting C 1
-C
4 alkyl) or
-NR
2 2 group; P represents a -CH, -CR" denoting CI-C 4 alkyl) or -NR22(X-)r group; r denotes zero or 1;
R
2 2 represents an atom a C 1
-C
4 alkoxy radical or a
C
1
-C
4 alkyl radical;
R
23 and R 24 which may be identical or different, represent a hydrogen atom or halogen atom chosen from chlorine, bromine, iodine and fluorine, a Ci-C 4 alkyl or Ci-C 4 alkoxy radical or an -NO 2 radical; X- represents an anion preferably chosen from chloride, iodide, methyl sulphate, ethyl sulphate, acetate and perchlorate; with the proviso that: if R 2 2 denotes then r denotes zero; if K or P or M denotes an -N-(C 1
-C
4 )alkyl X- group, then at least one of the radicals R 23 and R 24 is other than a hydrogen atom; if K denotes -NR 22 then M P -CH or -CR"; if M denotes -NR 22 then K P -CH or -CR"; if P denotes -NR 22 then K M and denote -CH or
-CR;
if Z denotes a sulphur atom and R 21 denotes a Ci-C 4 alkyl radical, then R 20 is other than a hydrogen atom; if Z denotes -NR 22 and R 19 denotes a Ci-C 4 alkyl radical, then at least one of the radicals R 18
R
19 or a 5*0555
S
S. S S S
S.
17
R
20 in the group of structure G 2 is other than a C 1
-C
4 alkyl radical; J represents: either a group of structure J 1 below:
R-
7
J
1 in which:
R
25 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a C 1
-C
4 alkyl or C 1
-C
4 alkoxy radical, a radical -OH, -NO 2
-NHR
28
-NR
29
R
30 or -NHCO(C 1
-C
4 )alkyl, or forms, with R 26 a 5- or 6-membered ring which may or may not contain one or more hetero atoms chosen from nitrogen, oxygen and sulphur;
R
26 represents a hydrogen atom, a halogen atom chosen 15 from chlorine, bromine, iodine and fluorine, a C 1
-C
4 alkyl or Ci-C 4 alkoxy radical, or forms, with R 27 or R 28 S: a 5- or 6-membered ring which may or may not contain one or more hetero atoms chosen from.nitrogen, oxygen and sulphur;
R
27 represents a hydrogen atom, an -OH radical, an
-NHR
2 8 radical or an -NR 29
R
30 radical; a a 18
R
2 8 represents a hydrogen atom, a Ci-C 4 alkyl radical, a Ci-C 4 monohydroxyalkyl radical, a C 2
-C
4 polyhydroxyalkyl radical or a phenyl radical;
R
29 and R 3 0 which may be identical or different, represent a Ci-C 4 alkyl radical, a C 1
-C
4 monohydroxyalkyl radical or a C 2
-C
4 polyhydroxyalkyl radical; Sor a 5- or 6-membered heterocyclic group containing nitrogen, which can contain other hetero atoms and/or carbonyl groups and can be substituted with one or more C 1
-C
4 alkyl, amino or phenyl radicals, and in particular a group of structure J 2 below:
N
N
in which:
R
31 and R 32 which may be identical or different, represent a hydrogen atom, a Ci-C 4 alkyl radical or a phenyl radical; Y denotes a -CO- radical or the radical
-C=
.CH3 *o e 19 n 0 or 1, it being understood that when n 1, then U denotes a -CO- radical.
In the structures to (IV) defined above, the CI-C 4 alkyl or alkoxy group preferably denotes methyl, ethyl, butyl, methoxy or ethoxy.
The cationic direct dyes of formulae (III) and (III') which can be used in the dye compositions in accordance with the invention are known compounds and are described, for example, in the patent applications WO 95/01772, WO 95/15144 and EP-A-0,714,954. The cationic direct dyes of formula (IV) which can be used in the dye compositions in accordance with the invention are also known compounds and are described, for example, in patent applications FR-A-2,189,006, FR-A-2,285,851 and FR-A-2,140,205 and its certificates of addition.
Among the cationic direct dyes of formula (I) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to **structures (Ii) to (152) below: *o*oo o*o
/NH-OH
3 CF Ii
NH
3 CH3 N
/CH
3 N CF- (12) N
-CH
3 CH 3 CH3
H
3 -N+C C /H 3 CHCH3 C 0HCH/ /CH 3 cI. (13) (14) di- /CH3
CH
3
H
3
C-
CI* (16) ci- (17) (18) *N\ CH 3 CH- Cl (19)
H
3 N O H 3
UH
3 OH3 N/
N
N=N /NH 2 CL, (110)
OH
3
CH
3 LIN N=N NH 2 Cl. (111)
OH
3 OCH 3
OH
3 N* N=N N CL .(112)
C
2
H
N=N/ C 2
H
4
-CN
N NN C, .(113) N 0 2
H
4
-CN
OH
3
CH
3
N+
IIN N=N NH 2 01, (114)
CH
3 C
CH
3 C, N N=N -NH CV (11)
CH
3
N
CH
3 Hc 3 N+ I N N=N 0N CV (17
CC
2
H
H
3 03
CH
3 N=N+ NN 0CV (11) N N CA 3
CH
3
OH
3 N
H
i, -N=N-ON cI. (119) N+
-CAH
OH 3
OH
3 CN
H
_N=NN l N+ C0H 2
-CH
2 2
OH
3
OH
3
OH
3
/H
N/
N=N N CV (121)
OH
3
OH
3 N
/H
N=N ON CF (122) N+ -CH 2
-CH
2
-CN
OH
3
CH
3 Nj NN N /OFl (123) N
OH
3
OH
3
OC
3 (124) (125) CH 3
OH
3 CI s N=N O NH 2 (126)
OH
3 N4+ O H2-OH2-ON CK N=N N 2 2N CH 3
OH
3 /l iNH 2 01
N
CH 3 0-OH 3 OH 0 -OH 3 N/
H
C, N=N i s N H3
CI
CH
3
OH
3 Or (127) (128) (129)
H
3 C- N4- cI- (130) NH
NH
2 CI (131)
-NH
2 1CH 3 s- N=N
CH
3 Cl
C
(132) 1. (133) CI- (134) CI. (135)
U
CHi-N+ I N N
OH
3 CH
CH
3 H N=N+ CH 3 H N= -O
H
3 N
OH
3
OH
3 Cl- (136) Cl (137) O H 3
N
CH
3 O H 3 0*
H
3 0-0 N=N 0-OH 3
H
3
C
N=N
OH
3 S C H 3 N+
CHN
CH
3 NS OH3
N/
KN+ N=
H
3 CI. (138) Cr (139) CI- (140) Cl- (141)
C.
c HOO
HO
(9V1) 10 N=N
CHO
C
4* C. C
C*
*CC*
C
C
CCC.
Cs C. C (9ti)
NO
-10 N N-N HO N
+ND
HHO
t0 ~HO
NO+
£HO
(etii)
CHO
HN N N-
D
N
(ztrI)
CH
3 CN =N
H
CH
3
CH
3 Cl* (147) CH 3S0 4 (148)
CH
3
/N
CH 3
*N\
CH 3 C2HS CN+ CH 3 1II~ N=N N CH 3
CH
3
/N
-N=Nr
Y
LII N
I
CH
3
SO
4 (149) cI (150)
OSSS
0 0000 0 *000 S0 00 0000 0* 00 0
S
0000 0* 0 0000 S S 5* 0 5.0000 5* 00
O-CH
3
NH
2 CF '(151) and
CH
3 O-CH 3 N+ CH3 N 'N Cl (152) N
CH
3
CH
3 CH 3 Among the compounds of structures (Ii) to (152) described above, the ones most particularly preferred are the compounds corresponding to structures (114) and (131).
Among the cationic direct dyes of formula (II) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (II) to (1112) below: H3C SN=N N Cl' (111) H3C S
CH,
e
CH
N-N N CI (112)
N+\
CH
S eH 3
OH
3 CHi-N+ N=N O N
CH-
3 (113) CH 3 N O- N\ C
H/
(114)
IH
CI*
OH
3
H
3 C 3 N
CH
3 S0 4 (116)
CH
3
SO
4 (117)
CH
3 S0 4 -(118)
OH
3 IN CH 2
-CH
2
-CN
S
OH
3
CH
3
N--N+/C
I N=N N N SC
I
OH
3 Cl. (119)
CH
3 S0 4 (1110)
CH
3 S0 4 (1111) and
OH
3 CH 3
H
2 N Os NN-- H 3
CH
3
SO
4 (1112) Among the cationic direct dyes of formula (III) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (1111) to (11118) below: CH=N-N0
I
CH
3 C1.
(1111)
CH
3
CI-
CI.
0
H
3 C N-
H
H3 CH=N-N
CH
3 (1112) (1113)
H
3
-GHN-
CH
3
SO
4 -(1114) /3-N CH=N-N OCH 3
CH
3 cI. (1115)
H
3 C- CH 3 S0 4 (1116)
CH
3 S0 4 (1117)
H
3
C-
Cl, (1118) cI C (1119) cH 3 S 4 (11110) CH 3
SO
4 (11111) 1 CH 3 S0 4 (11112)
OCH
3 CH 3S0 4 a.
.a (11113)
CH
3 N/ iiQI. NN N OCH 3 C' (11114) N
OH
3 CH=CH
NH
2
CH
3 Cb00 (11115)
OH
3 H3 C-N DCH=CH NH 2
CH
3 000- (11116) H3C-N+ C1, (11117) CH H 3 and
OH
:I N=N C1, (11118) 0H3 Among the compounds of structures (1111) to :(11118) described above, the ones most particularly preferred are the compounds correspfnding to structures (1114), (1115) and (11113).
Among the cationic direct dyes of formula (III') which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (III'l) to (III'3) below:
I
S N N I IC (IllI1) N+ CH 3
NH
CH
3 UN3 CH-N+
CH=CH
C 1 11 '2) NH and r r r c (111'3)
CH
3
CH
CH
3 Among the cationic direct dyes of formula (IV) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (IV) 1 to (IV) 7 7 below: N+ N=N NN CH 3 N N=N /\OH 2 0 z NNHCOCH 3 I N N N -6NICH 3
(IV)
3 I CHCH(t) 0 N+ NN N NH 2 1- ('V)4 I C H2O 0 N =N /H 2 N V)s I 0 @000 0@0 0 N+ NN CH CH OH (V) H I- N CH 2 CH 2
OH
0 HC Ni- N=N CH 5 (V)a 0e0*00
H
3 CN+ N=N (IV) 9 I-
H
3 0
*CH
3 N+ N=N N\,"H 0I) 1
OH
3 I2 N+ N=N N~ 2 I.
'CAH
0
OH
3 SCH CH OH N+ N=N 2 2 V1 I C 2
CH
2 0 0
OH
3 N+ N=N /\NH 2 1 3 0 3 C N+ N=N H tV 1 3 rI N.C 3( I
OH
3 3 N+N=N
(V)
1
H
3 N
C
H
3
CH
N+ N=N N C 3 (tV) 19 I- -a CH3 0 I
CH
3 N+ NN N (IV) I CH3 0 CI -H N+ N=N N 3CH 0 CH c HOH HNE0 =HN N=N cCHO "(l)HO I N N +N I0 +N99 HO z HOzH "(At) I 99N N= N
N=N
H HD~O -0 SECA) /N N=N
HO)-
~0
I
N=N U+N 0 H to ~CH3- I N+ NN N NH 2 ('V)29 CH 3 0H 3 S0 4 CH 3 N+ N=N
NI.
7 C H 2 CH 2 0H
(V
I~ /a 1-CH 2CHO2H V3
OH
3 22 CH 3 S0 4 I aN =NN ,CH 31 I Oa11c2H5
H
3
CH
3 S0 4
OH
N=N N CH 3(tV) 32 *CH 3 S0 4 N=N -b N( 3 3 I C 3
H
3
CH
3 S0 4
H
H
3 C N N =N (IV)34 CH 3
CH
3 so 4 43
HF
3
C
CH
3
ICH
3
CH
3 S0 4
NHCOCH
3 I ~CH 3
CH
3
CH
3 S0 4 (tV) 3 MOM)3 N+ CH 3
S
CH
3 9 OH 3 04 :N CH3 :N
OH
3
H
3
C
CH3 ~CH3 37
(IV)
38
H
3
C,
CF
CH
3 (IV6~ C H SOp* 9
C;
2
H
CH
3 ('\0410
CH
3
OH
3 CH 3 S0 4 NNa
CH
3
SO
4
(IV)
41
NHCOCH
3 OH 3
CHSO-
4 2
C;
2
H
S
*99W
S
est.
S
is..
5.
*5
S
S
*s S 5
S
S
S S
NN=N-
(N Br' O4H
I-
OCH 3
S
O-IH
3
~CH
3 ('V)43 ('V)44 7"N 0
CA
N0
H
I N N. N=N
(IV)
4 3 I
N
0'N 0 H O N N-O NI-IHSO.4 N ~CH 3
OH
3 0104
OH
3
-N
N- N OH 47 OHC104 I 0* 48
H
2 N O* N=N@ NH2(V4
NH
2 0S N+ N=N .5**04 OH H C N±N=N \NH
(JV)
51
OH
3
OH
NN N=N NH
(IV)S
2
OH
NH 2 N N-N
NH
2
(IV)
53 I 0
QCH
3 N
OH
3 N N=N OH ('V)54 0
NHCOCH
3 N
H
3 N+ N=N -ONH 2 (IV)3
OCH
3 H- N N N N-CH\ (IV)56
CH
3 03
NH
2
CH
3 N+ N=N OH (IV) 57 1I- 0 CH 3 N N=N P OH (IV)58 1 0
H
3 C
OH
3 aN+ N=N -N'(V .0.
OH
N.
OH
3 N N N OH(I) 4 I
*CH
3 N N N \NCH
(N)
61 I-
CH
3 0 3 .NO 2 N+ N=N H(I) I )6 0 48 .0 2 N tC I N= ,c CHI 'V6
I-
N+ NN N N.(V) 6 3 1
CH
3
UUH
3
O
3
CH
3 SO.,
NO
2
OH
3
H
3 C /\OH (tV) 6 t 0
OH
3
OH
3 CH1 3 N+ N=N OH O'V)6e 0
*CH
3 /C 3 N N=N /9 N
H
67 IH NH1 2
CH
3
SO
4 N0 N N >(IV)sa 0 HOaNH 49 N+ N =N (IV) 69
OCH
3 HO
NH
CH
3
SO
4 NH 2 N N=N O NH 2
(IV)
70 I 0
OH
3 0
H
I N I N+ N N 71 I.
N
o' 0 CH 3 N N=N NH 2 ON 72 /CH 2 CCHHC 2
OH
I~CH
2
CH
2 0H N+ ('V)73
CH
3
SO
4 CH3 00H 3 N N=N NH 2 NN H 2 (11/)74 I
CHS-
OH
3
C
3
O
-NH
2 N+ NH2
(V)
7 I CH 3
SO
4
CH
3
CH
3
CH
3
I-
N+ NN 'NH (IV^)
NH
2 and ZCH3 N=N -N
/CH,
N+
(IV),
I CH 3 SO NO 2
CH
3 The pyrazolo[l, 5-a]pyrimidine(s) of formula in accordance with the invention and/or the addition salt(s) thereof with an acid or with a base preferably represent(s) from 0.0005 to 12% by weight V; approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately relative to this weight.
The cationic direct dye(s) used according to 10 the invention preferably represent(s) from 0.001 to by weight approximately relative to the total weight of
I
the dye composition and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
The medium which is suitable for dyeing (or the support) generally consists of water or of a mixture of water and at least one organic solvent in order to dissolve the compounds which would not be sufficiently soluble in water. By way of organic solvent, mention may be made, for example, of Ci-C 4 alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
The solvents can be present in proportions preferably of between 1 and 40% by weight approximately relative 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 in accordance with the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value using acidifying or basifying agents commonly used for 25 dyeing keratin fibres.
Among the acidifying agents, mention may be made, by way of example, of inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
Among the basifying agents, mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines, 2-methyl-2-aminopropanol and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (Vi) below: Ra R
R
6
R
38 N-W-N (VI) R7 R39 in which W is a propylene residue optionally S 15 substituted with a hydroxyl group or a C 1
-C
6 alkyl radical; R 36
R
37
R
38 and R 39 which may be identical or different, represent a hydrogen atom or a Ci-Cs alkyl or
C-C
6 hydroxyalkyl radical.
The dye composition in accordance with the invention can also contain one or more couplers which can be chosen from the couplers used conventionally in oxidation dyeing and among which mention may be made in particular of meta-phenylenediaminel, meta-aminophenols, meta-diphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones, and the addition salts thereof with an acid.
These couplers are chosen more particularly from 2-methyl-5-aminophenol, 2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxy-* benzene, 2,4-diamino-l-(P-hydroxyethyloxy)benzene, 2-amino-4-(P-hydroxyethylamino)-1-methoxybenzene, 1,3diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, a-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 2,6dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one and l-phenyl-3-methylpyrazol-5-one, and the addition salts thereof with an acid.
When they are present, these couplers preferably represent from 0.0001 to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 20 by weight approximately relative to this weight.
The dye composition in accordance with the invention can also contain one or more additional oxidation bases other than a and/or one or more non-cationic direct dyes, in particular in order to modify the shades or to enrich themi with glints.
Among the additional oxidation bases which can be used in the dye compositions in accordance with the invention, mention may be made of para-phenylenediamines, bis (phenyl) alkylenediainines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
Among the para-phenylenediamines, mention may be made more particularly, by way of example, of paraphenylenediamine, para-toluylenediamine, 2-chloro-paraphenylenediamine, 2, 3 -dime thyl -para -phenyl1enedi amine, 2, 6-dimethyl-para-phenylenediamine, 2, 6-diethyl-paraphenylenedianine, 2, N, N-dimethyl-para-phelylenediamile, N,N-diethyl-paraphenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis (Jhydroxyethyl) -para--phenylenediamine, 4-N, N-bis hydroxyethyl) amino-2-methylaniline, 4-N,N-bis (fhydroxyethyl) amino-2-chloroaiiline, 2-j-hydroxyethylpara-phenylenediamine, 2-f luoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N- (f-hydroxy-propyl) para-phenylenediamine, 2-hydroxyrnethyl-paraphenylenediamine, N, N-dimethyl-3 -methyl-paraphenylenediamine, N-ethyl-N- (f-hydroxyethyl) -paraphenylenediamine, N- (P3,y-dihydroxypropyl) -paraphenylenediamine, N- (4 '-aminophenyl) -para-phenylenediamine, N-pheny1-para-phenylenediamine, 2-J3-hydroxyethyloxy-para-phenylenediamine, 2 -t-acetylaminoethyloxy-para-phenylenediam~ine and N- (P-methoxyethyl) para-phenylenediamine, and the addition salts thereof with an acid.
Among the para-phenylenediamines mentioned abve para-phenylenediamine, para- toluylenediamine, 2-isopropyl-para-phenylenedianine, 2-f3-hydroxyethylpara-phenylenediamine, 2-p-hydroxyethyloxy-paraphenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2, 3-dimethyl-paraphenylenediamine, N, N-bis (f-hydroxyethyl) -paraphenylenediamine, 2-chioro-para-phenylenedianine and 2--acetylaminoethyloxy-para-phelylenediamine and the addition salts thereof with an acid are most *particularly preferred.
Among the bis (phenyl)alkylenediamines, mention may be made more particularly, by way of 20 example, of N,N'-bis(f3-hydroxyethyl) -N,N'-bis(4'-amino- Sphenyl) 3-diarninopropanol, N,N' -bis (P-hydroxyethyl) N,N'-bis(4'-aminophenyl)ethylenediafine, N,N'-bis(4aminophenyl) tetramethylenediamine, N,N' -bis (f-hydroxyethyl) -bis (4-aminophenyl)tetranethylenediamile, N,N' -bis (4-methylaminophenyl) tetramethylenediamine, N,N-bis(ethyl)-N,N'-bis-bis(4'-amino-3 -methylphenyl) ethylenediamine and 1,8-bis(2,5-diaminophenoxy)-3,5dioxaoctane, and the addition salts thereof with an acid.
Among the para-aminophenols, mention may be made more particularly, by way of example, of paraaminophenol, 4-amino-3-methylphenol, 4-amino-3fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (-hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
Among the ortho-aminophenols, mention may be made more particularly, by way of example, of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
20 Among the heterocyclic bases, mention may be S" made more particularly, by way of example, of pyridine o* derivatives, pyrimidine derivatives other than the S" compounds of formula in accordance with the invention and pyrazole derivatives.
Among the pyridine derivatives, mention may be made more particularly of the compounds described, for example, -in patents GB 1,026,978 and GB 1,153,196, such as 2, 5-diaminopyridine, 2- (4-inethoxyphenyl) amino- 3 -aminopyri dine, 2, 3-diamino-6-inethoxypyridine, 2- (1meth oxyethyl) amino- 3- amino- 6-me thoxypyridine and 3,4di aminopyri dine., and the addition salts thereof with an acid.
Among the pyrimidine derivatives, mention may be made more particularly of. the compounds described, for example, in German patent DE 2,359,399 or Japanese patents JP 88-169,571 and JP 91-10659 or patent application WO 96/15765, such 'as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2, 5, 6-triaminopyrimidine, 2hydroxy- 4, 5, 6 -triaminopyrimi dine, 2, 4-dihydroxy-5, 6diaminopyrimidine and 2, 5, 6-triaminopyrimidine.
Among the pyrazole derivatives, mention may be made more particularly of the compounds described in patents DE 3, 843, 892, DE 4, 133, 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988, such as 20 pyrazole, 3,4-diaminopyrazole, 4,5-dianino-1--(4'chlorobenzyl)pyrazole, 4, 5-diainino-1, 3-dimethyldiamino-1-methyl-3-phenylpyrazole, 4-ainino-l, 3- 1-benzyl-4, 5-diamino-3- 25 methylpyrazole, 4, 5-diamino-3-tert-butyl-l-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, (f-hydroxyethyl)-3-methylpyrazole, diamino-1-ethyl-3-methylpyrazole, 4, 5-diamino-1-ethyl- 3- -rethoxyphenyl)pyrazole, 4, 5-diamino-1-ethyl-3hydroxymethylpyrazole, 4, 5-diaxnino-3-hydroxymethyl-lmethylpyrazole, 4, 5-diamino-3-hydroxynethyl-l-isopropylpyrazole, 4, 5-diaxnino-3-rethyl-l-isopropylpyrazole, 4-amino-5- (2'-aminoethyl)axnino-1,3-dimethylpyrazole, 3,4, 5-triarninopyrazole, 1-methyl-3,4, triaminopyrazole, 3, 5-diamino-1-methyl-4-methylaminopyrazole and 3, 5-diamino-4-(13-hydroxyethyl)amino-lmethylpyrazole, and the addition salts thereof with an acid.
When they are used, these additional oxidation bases preferably represent from 0.0005 to 12% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately relative to this :weight.
In general, the addition salts with an acid which can be used in the context of the invention (compounds of formula additional oxidation bases and couplers) are chosen in particular from the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates. The addition salts with a base which can be used in the 59 context of the dye compositions of the invention (compounds of formula are, in particular, those obtained with sodium hydroxide, potassium hydroxide, aqueous ammonia or amines.
The dye composition in accordance with the invention can also contain various adjuvants used conventionally in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickening agents such as, for example, nonionic guar gums, antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, conditioners such as, for example, volatile or non-volatile, modified or unmodified silicones, film-forming agents, eo ceramides, preserving agents and opacifiers.
Needless to say, a person skilled in the art Swill take care to select this or these optional 20 additional compounds such that the advantageous properties intrinsically associated with the oxidation dye composition in accordance with the invention are not, or are not substantially, adversely affected by the addition(s) envisaged.
S"I 25 The dye composition according to the invention can be in various forms, such as in the form of liquids, powders, creams or gels or any other form which is suitable for dyeing keratin fibres, and in particular human hair.
A subject of the invention is also a process for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, using the dye composition as defined above.
According to this process, at least one dye composition as defined above is applied to the fibres, the colour being developed at acidic, neutral or alkaline pH using a non-enzymatic oxidizing agent which is added to the dye composition only at the time of use or which is present in an oxidizing composition that is applied simultaneously or sequentially.
According to one preferred embodiment of the dyeing process of the invention, the dye composition o described above is preferably mixed, at the time of use, with an'oxidizing composition containing, in a medium which is suitable for dyeing, at least one nonenzymatic oxidizing agent present in an amount which is sufficient to develop a coloration. The mixture obtained is then applied to the keratin fibres and is left to stand on the fibres for 3 to 50 minutes approximately, preferably 5 to 30 minutes 25 approximately, after which the fibres are 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 the oxidation dyeing of keratin fibres, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bromates, peracids and persalts such as perborates and persulphates. Hydrogen peroxide is particularly preferred.
The pH of the oxidizing composition containing the oxidizing agent as defined above is such that, after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibres preferably ranges between 3 and 12 approximately, and.
even more preferably between 5 and 11. It is adjusted to the desired value with the aid of acidifying or basifying agents commonly used for dyeing keratin fee* fibres and as defined above.
oo The oxidizing composition as defined above can also contain various adjuvants conventionally used 20 in compositions for dyeing the hair and as defined above.
The composition which is finally applied to the keratin fibres can be in various forms, such as in the form of liquids, creams or gels or any other form which is suitable for dyeing keratin fibres, and in particular human hair.
62 Another subject of the invention is a multicompartment dyeing device or multi-compartment dyeing "kit" or any other multi-compartment packaging system, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition as defined above. These devices can be equipped with a means for applying the desired mixture to the hair, such as the devices described in patent FR-2,586,913 in the name of the Applicant.
The example which follows is intended to illustrate the invention without thereby being limiting in nature.
o *o• 63 EXAMPLE OF DYEING IN ALKALINE MEDIUM The dye composition below, in accordance with the invention, was prepared: Pyrazolo[1, 5-a]pyrimidine-3,7-diamine dihydrochloride (oxidation base) 0.333 g Cationic direct dye of formula (12) 1 g 960 ethyl alcohol 18 g Pentasodium salt of diethylenetriaminepentaacetic acid 1.1 g Aqueous ammonia containing 20% NH 3 10.0 g Demineralized water qs 100 g The above dye composition was mixed weight for weight, at the time of use, with a hydrogen peroxide solution by weight) of pH 3.
The mixture obtained was applied to locks of .9 natural grey hair containing 90% white hairs, for minutes. The locks were then rinsed, washed with a 20 standard shampoo, rinsed again and then dried.
The hair was dyed in an intense fuchsia shade.
For the purposes of this specification it will be clearly understood that the word "comprising" means "including but not limited to", and that the word "comprises" has a corresponding meaning.
Claims (17)
1. Composition for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, characterized in that it contains, in a medium which is suitable for dyeing: at least one pyrazolo[l,5-a]pyrimidine as oxidation base; and at least one cationic direct dye; the said composition being free of any enzymatic system capable of bringing about the oxidation of the
2. Composition according to Claim 1, characterized in that the is (are) chosen from the compounds of formula (V) below, and the addition salts thereof with an acid or with a base: 9* 5 N e NN (V) 7 [NR 3 S s]q in which: 20 R 33 R 34 R 35 and R 36 which may be identical or different, denote a hydrogen atom, a Ci-C 4 alkyl *radical, an aryl radical, a Ci-C4 hydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a (Ci-C4)alkoxy- (Cl-C 4 )alkyl radical, a Cl-C 4 aminoalkyl radical (it beingr possible for the amine to be protected with an acetyl, ureido or suiphonyl radical), a (C 1 -C 4 alkyl- amino (Cl-C 4 alkyl radical, a di (Cl-C 4 alkyl] amino- (C-C 4 )alkyl radical (it being possible for the dialkyls to form a 5- or 6-merrbered aliphatic or heterocyclic ring), a hydroxy(Cl-C 4 alkyl- or di [hydroxy- (C 1 -C 4 alkyll amino (Cl-C 4 alkyl radical; the radicals R, which may be identical or different, denote a hydrogen atom, a Cl-C 4 alkyl radical, an aryl radical, a Cl-C 4 hydroxyalkyl radical, a C 2 -C 4 Poly- hydroxyalkyl radical, a Cl-C 4 aminoalkyl radical, a (C 1 -C 4 alkylamino (Cl-C 4 alkyl radical, a di (C 1 -C 4 alkyl) amino (Cl-C 4 alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered aliphatic or heterocyclic ring), a hydroxy(C 1 -C 4 )alkyl- or di [hydroxy(CI-C 4 alkyl] amino (C-C 4 alkyl radical, an soot *.amino radical, a (Cl-CO)alkyl- or di[((Cl-CO)alkyl Iamino radical; a halogen atom, a carboxylic acid group or a sulphonic acid group; i is equal to 0, 1, 2 or 3; p is equal to 0 or 1; q is equal to 0 or 1; *go. n is equal to 0 or 1; 25 with the proviso that: the sum p q is other than 0; 66 (i)when p q is equal to 2, then n is equal to 0 and the groups NR 33 R 34 and N-R 35 R 3 6 OCCUPY the 3); or positions; (iii) when p, q is equal to 1, then n is equal to 1 and the group NR 33 R 34 (Or NR 35 R 36 and the OH group occupy the 6) or positions.
3. Composition according to Claim 2, characterized in that the pyrazolo(l,5-a]pyriinidines of formula are chosen from: pyrazoloti, 5-a]pyrimidine-3, 7-diamine; 2-methylpyrazolo 5-alpyrimidine-3, 7-diainine; 2, 5-dimethylpyrazolo [1,5-alpyrimidine-3, 7-diamine; pyrazolo[1,5-alpyrimidine-3, 2,7-dimethylpyrazolo(1,5-alpyrimidine-3, 3-aininopyrazolofi, 5-alpyrimidin-7-ol; 3-amino-5-methylpyrazolo (1,5-a]pyrirnidin-7-ol; 3-aminopyrazolo[l, *too 2- (3-amninopyrazolo[1, 5-al pyrimidin-7-ylamino) ethanol; 3 -amino-7 -f-hydroxyethylamino-5 -methylpyrazolo- -methyl-7 -imidazolyipropylamino pyrazolo- -pyrimidine; (7-aiinopyrazolo[1, 5-alpyrimidin-3-ylamino) ethanol; -2-f (3-aminopyrazolo[1,5-a]pyrimidin-7-yl)- (2-hydroxy- 0 ethyl) amino] ethanol; 2-f -mnprzl(15aprmdn3-l-2hdoy ethyl) amino] ethanol; 5,6-dimethylpyrazolof,5-alpyrimidine-3,7-diamine; 67 2, 6-dimethylpyrazolo pyrimidine-3,7-diamine; 2,5,N7,N7-tetramethylpyrazolo[1,5-alpyrimidile-3,7- diamine; and the addition salts thereof with an ac id or with a base.
4. Composition according to any one of the preceding claims, characterized in that the cationic direct dye(s) is (are) chosen from cationic aminoanthraquinones, cationic mono- or diazo compounds and cationic naphthoquinones. Composition according to Claim 4, characterized in that the cationic direct dyes are chosen from [(p-aminophenyl) azol -7-hydroxy- 2 -naphthyl I tr ime thyl ammonium chloride, the combination of 3 (4 -amino- 6-bromo-5, B-dihydro-l1-hydroxy- 8-imino-5 oxo-2-naphthyl) amino] N, N-trimethylbenzenaminiuf chloride and of 3- 6-dibromo-5, 8-dihydro-l-hydroxy-
8-imin'o-5-oxo-3-naphthyl) amino] -N,N,N-trimethyl- benzenaxninium, chloride, 7-hydiroxy-8- ((2-methoxy- 20 phenyl) azo] N-trimethyl--2-napht halenaminium chloride, (4-amino-2-nitrophenyl' azo]-7-hydroxy- 2 naphthyl )tr ime thyl ammoniumn chloride, the combination of [(4-amino--3-nitrophenyl)azo] -7-hydroxy-2- naphthyl]trimethylammoniuf chloride and of 25 amino-2-nitrophenyl) azo) -7-hydroxy-!2-naphthyl] trimethylamnoniun chloride, 3- 5-dihydro-3-methyl-5- 68 oxo-l-phenyl-lH-pyrazol- 4 -yl)azo] -N,N,N-trimethyl- benzenaminium chloride, 1- (y-aminopropyl) aminoanthra- quinone hydrochloride, 1-N- (methylmorpholiniumpropyl)- amino-4-hydroxyanthraquinone methyl sulphate and Basic Orange 69®. 6. Composition according to any one of Claims 1 to 3, characterized in that the cationic direct dye(s) is (are) chosen from the compounds of formulae (III), (III') and (IV) below: a) compounds of formula R' 3 R, A-D=D N (I) XRR R 3 in which: S. D represents a nitrogen atom or a -CH group, Ri and R 2 which may be identical or different, represent a hydrogen atom; a C 1 -C 4 alkyl radical which can be substituted with a -CN, -OH or -NH 2 radical or form, with a carbon atom of the benzene ring, a heterocycle optionally containing oxygen or nitrogen, which can be substituted with one or more Ci-C 4 alkyl 20 radicals; a 4'-aminophenyl radical, R 3 and R' 3 which may be identical or different, represent a hydrogen atom or a halogen atom chosen from 69 chlorine, bromine, iodine and fluorine, or a cyano, C 1 -C 4 alkoxy or acetyloxy radical, X- represents an anion preferably chosen from chloride, methyl sulphate and acetate, A represents a group chosen from structures Ai to A 19 below: .e R4 N +N I R4 N I- A 2 N A 3 N-N.. 4 N N-N (IN -N A 7 +1 R N, 4 N 41 N R 4 I+' N=N+ All 0w- N+ A 1 2 N+ R4 1R 4 I S 1N 4 N-N A 1 3 A 1 4 A 1 A15 S II N- R 4 N N- R4 A 16 A 17 A 18 IR a 4 N N+ A 9 R4 in which R 4 represents a C 1 -C 4 alkyl radical which can be substituted with a hydroxyl radical and Rs represents a Ci-C 4 alkoxy radical, with the proviso that when D represents -CH, A represents A 4 or A 13 and R 3 is other than an alkoxy radical, then RI and R 2 do not simultaneously denote a hydrogen atom; b) compounds of formula (II): :R, B-N=N N (II) R 7 x\ X- in which: R 6 represents a hydrogen atom or a CI-C 4 alkyl radical, R 7 represents a hydrogen atom, an alkyl radical which can be substituted with a -CN radical or with an amino group, a 4'-aminophenyl radical or forms with R 6 a heterocycle, optionally containing oxygen and/or nitrogen, which can be substituted with a Cl-C 4 alkyl radical, Rs and R9, which may be identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine or fluorine, a C 1 -C 4 alkyl or C 1 -C 4 alkoxy radical or a -CN radical, X- represents an anion preferably chosen from chloride, methyl sulphate and acetate, 15 B represents a group chosen from structures B1 to B6 below: Rio R 10 /R 1 0 ,R 1 0 N N--N N-N' S R S N S R12 B1 B2 B3 *o 73 I- and and R-N,, N+ N Rio Ro RRNS B4 B5 B6 in which Rio represents a C 1 -C 4 alkyl radical and R 11 and R 12 which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical; c) compounds of formulae (III) and (III'): R 14 1 D D, ED1--D2"(N) R13 X" .H D m R X R, R 1 7 N -(ill) (ii') *1 in which: S: R 3 represents a hydrogen atom, a C 1 -C 4 alkoxy radical, 10 a halogen atom such as bromine, chlorine, iodine or fluorine or an amino radical, R 14 represents a hydrogen atom, a Cz-C 4 alkyl radical or forms, with a carbon atom of the benzene ring, a heterocycle optionally containing oxygen and/or .15 substituted with one or more C 1 -C 4 alkyl groups, I 74 R 15 represents a hydrogen atom or a halogen atom such as bromine, chlorine, iodine or fluorine, R 16 and R 17 which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical, Di and D 2 which may be identical or different, represent a nitrogen atom or a -CH group, m 0 or 1, it being understood that when Ri3 represents an unsubstituted amino group, then Di and D 2 simultaneously represent a -CH group and m 0, X- represents an anion preferably chosen from chloride, methyl sulphate and acetate, E represents a group chosen from structures El to E8 below: N .N El E2 OH R. 0,0 N R R" N E3 E4 R' E5 R' and NN R' R' R' E6 E7 E8 in which R' represents a CI-C 4 alkyl radical; when m 0 and Di represents a nitrogen atom, then E can also denote a group of structure E9 below: R' N E9 R' in which R' represents a Ci-C 4 alkyl radical; d) compounds of formula (IV): N J (IV) S: in which: 10 G represents a group chosen from structures Gi to G3 below: *eeee oo•* *oooo g *e R1 R0 R,4 z R, NR 1 9 M I x M R, 8 R8 G, G, G 3 in which: R 18 denotes a C 1 -C 4 alkyl radical, a phenyl radical, a phenyl radical substituted with a Ci-C 4 alkyl radical or a halogen atom chosen from chlorine, bromine, iodine and fluorine; R 19 denotes a Ci-C 4 alkyl radical or a phenyl radical; R 20 and R 21 which may be identical or different, represent a Ci-C 4 alkyl radical, a phenyl radical or 10 together form, in Gi, a benzene ring substituted with one or more C 1 -C 4 alkyl, Ci-C 4 alkoxy or NO 2 radicals, or Stogether form, in G 2 a benzene ring optionally substituted with one or more Ci-C 4 alkyl, C 1 -C 4 alkoxy or NO 2 radicals; R 20 can also denote a hydrogen atom; 15 Z denotes an oxygen or sulphur atom or a group -NR 1 9; M represents a -CH, -CR" denoting Ci-C 4 alkyl) or -NR22(X')r group; K represents a -CH, -CR" denoting C 1 -C 4 alkyl) or -NR22(X )r group; P represents a -CH, -CR" denoting C 1 -C 4 alkyl) or -NR22(X-)r group; r denotes zero or 1; R 22 represents an atom a C 1 -C 4 alkoxy radical or a C 1 -C 4 alkyl radical; R 23 and R 24 which may be identical or different, represent a hydrogen atom or halogen atom chosen from chlorine, bromine, iodine and fluorine, a CI-C 4 alkyl or C 1 -C 4 alkoxy radical or an -NO 2 radical; X- represents an anion preferably chosen from chloride, iodide; methyl sulphate, ethyl sulphate, acetate and perchlorate; with the proviso that: if R 22 denotes then r denotes zero; if K or P or M denotes an -N-(C 1 -C 4 )alkyl X- group, 15 then at least one of the radicals R 23 and R 24 is other than a hydrogen atom; if K denotes -NR 22 then M P -CH or -CR"; if M denotes -NR22(X-)r, then K P -CH or -CR"; if P denotes -NR 22 then K M and denote -CH or .o 20 -CR; if Z denotes a sulphur atom and R 21 denotes a C 1 -C 4 alkyl radical, then R 2 0 is other than a hydrogen atom; if Z denotes -NR 22 and R 19 denotes a Ci-C 4 alkyl Sradical, then at least one of the radicals R 18 R 19 or R 20 in the group of structure G 2 is Other than a Ci-C4 alkyl radical; 78 J represents: either a group of structure J 1 below: 2 7 J 6 in which: R 25 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a Ci-C 4 alkyl or Ci-C 4 alkoxy radical, a radical -OH, -NO 2 -NHR 28 -NR 29 R 30 or -NHCO(Ci-C 4 )alkyl, or forms, with R 26 a 5- or 6-membered ring which may or may not contain one or more hetero atoms chosen from nitrogen, oxygen and sulphur; R 26 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a Ci-C 4 ,C:o alkyl or C 1 -C 4 alkoxy radical, or forms, with R 27 or R28, 15 A 5- or 6-membered ring which.may or may not contain 9 one or more hetero atoms chosen from nitrogen, oxygen and sulphur; 9 R 27 represents a hydrogen atom, an -OH radical, an NHR 28 radical or an -NR 2 9R 3 0 radical; R 28 represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical or a phenyl radical; R 29 and R 30 which may be identical or different, represent a CI-C 4 alkyl radical, a Ci-C 4 monohydroxyalkyl radical or a C 2 -C 4 polyhydroxyalkyl radical; or a 5- or 6-membered heterocyclic group containing nitrogen, which can contain other hetero atoms and/or carbonyl groups and can be substituted with one or more C 1 -C 4 alkyl, amino or phenyl radicals, and in particular a group of structure J 2 below: N N o F2 in which: R 31 and R 32 which may be identical or different, represent a hydrogen atom, a Ci-C 4 alkyl radical or a C phenyl radical; 15 Y denotes a -CO- radical or the radical -c= 3 n 0 or 1, it being understood that when n 1, then U denotes a -CO- radical. C 7. Composition according to Claim 6, characterized in that the cationic direct dyes of formula are chosen from the compounds corresponding to structures (Il) to (152) below: CH 3 N+ OH 3 NH -OH 3 0 *0 0* H N ON\ H cl (12) IOI (13) O H 3 OH 3 CH CHO N N CH- 3 CH 3 H 3 C-N+ -CH==0H 1 O N N/ 0 c 4CON Cl HO-H 4 0 2 OF (16) CI.- (17) N+- OCH 3 OH 3 CH 3 'CH 3 UH 3 OH3 -N=N NH 2 N CH 3 OH 3 ,N (112) OCH 3 NH 3 /0 2 H KIN N=N ON\ N C 2 H CH 3 83 CH 3 CN+ /C 2 H 4 -CN KN N=N N CV (13 N C 2 H 4 -CN OH 3 CH 3 N+' [u N N=N NH 2 CV, (114) CH 3 CH N+ N=N /1 NH 2 CU (115) 0113 CI CHH jEI N=N NH 2 CU (116) OH 3 3 HOH 3 NN+ N N=N .0Nc 17 H 3 c 84 CH 3 N=N 0 CL, (118) NI N OH 3 OH 3 3 UH 3 CH 3 FK N=N N cl (119) CH 3 OH 3 N=N N CI (120) N+ CH 2 -CH 2 -NH 2 CH 3 CH N H N C1 (121) -N CH 2 -CH 2 -OH OH 3 CHH N _N CL (122) CH 3 ,N /OH3 .N\ OH 3 /CH3 N\ N=N 0 -N OH 3 3 OH 3 OH 3 O 3 CH 3 OH 3 sN=Na NH2 0I*- 0Il CI- CI (123) (124) (125) (126) a. a OH 3 N+ O H2-OH2-ON C, N=Na N2 s OH 3 CF (127) CH 3 0-OH 3 N=N -NI-I N OH 3 0-OH 3 OH 3 0-OH 3 N+ OCH cl N=N -N\ N OH 3 OH 3 OH 3 I/ H 3 H 3 0-N+ N=N N OH 3 01- (128) cI.* (129) (130) OV (131) O NH 2 cl, (132) OCH 3 CH3 zt' N=N N N+ \CH 3 OH 3 CH CHS-N+3 CHH3 COH 3 H N=N+ /CH3 H 3 C-O 0 N N N\ H N C H 3 ci /CH 3 N N=N- N N -N OH 3 (133) CI- (134) CI. (135) CI (136) Ci (137) a a a. a .H 3 OH 3 N=N+ OCH H C-0 N=N N CH 3 H 3 C O H 3 N==N N OH 3 OH 3 s CH 3 iI N=N N C N4 OH 3 CH 3 Cl* (138) Cl. (139) 1 (140) V (141) Cl (142) N' O H 3 N=N N OH 3 s /OH 3 -N=N N N CH 3 0 CH 3 N NH (143) CH 3 CH3 NS CI- (144) CI (145) S S S. S a. S6a a. OH3 OH 3 N/ Cc>- CH 3 CH 3 13 OH 3 OH 3 CI (146) CI- (147) aS CH 3 EN+ NNN/CH3 CH 3 C' C2H EN+ NNN/CH 3 NN ~CH 3 CH 3 S0 4 (148) CH 3 SO 4 (149) CI. (150) CH 3 0 0 000* 0 0*0* 0* 0 *00* 0 ~0 0* 000* *0 0 NH 2 (151) ,and CH 3 CH 3 0-C H (152) OH 3 8. Composition according to Claim 6, characterized in that the cationic direct dyes of formula (II) -are chosen f rom the compounds corresponding to structures (IIl) to (1112) below: OH 3 N -N N H (111.) Cr' (112) CH 3 CH3 CH 3 (.113) *eve .00. 00... 0"(114) OH 3 N+ a /CH3 N OH 3 (115) H 3 C OHCH 3 N+N CH N S CH 3 NN N=N N\/ S CH 3 CH 3 SO 4 (116) CH 3 S0 4 (117) OH 3 OH 3 N 1 N N=N H 3 0 H CH 3 N+CH 2 -CH 2 -CN N N N -OCH 3 CH 3 OH N+ N /3 SL O-H 3 CH 3 S0 4 '(18 OF (119) CH 3 30 4 (1110) CH 3 NH CPH 3 CH 3 S0 4 (1111) and I NN N CH 3 S0 4 (1112) H 2 N S CH C- 3
9. Composition according to Claim 6, characterized in that the cationic direct dyes of formula (III) are chosen from the compounds corresponding to structures (1111) to (11118) below: S S S. S S S S S S CH=N-N CF" (1111) NI! CH OH 3 0 H3C){CH3 ICH=N-N cI (1112) 0 H 3 C N N CH ICH=N-N CI (1113) H3 CH 3 CH 3 S0 4 -(1114) H 3 C-N+ CH=N-N OCH 3 1 .0 CH 3 H C-N+ CH=N-N cI (1115) CH 3 S04 (1116) H 3 C CH 3 S0 4 (1117) H 3 C- CI- (1118) H 3 C-N+ -CH=N-N c I CI (1119) CH 3 S0 4 (11110) CH 3 S0 4 (11111) 'I CH 3 S0 4 (11112) -OCH 3 CH 3 SO 4 (I 'C 1113) a a. a t CH 3 jN -O OCH 3 CH 3 CI,(11114) 2 -CH=CH- NH 2 CH 3 COO' (11115) CH 3 H3C-,N+ -CH=CH CNH 2 CH 3 COO- (11116) H 3 C-N+ CH=N-N I CH 3 C1 (11117) and 0-0-N=N C1, (11118) S aS..
10. Composition according to Claim 6, characterized in that the cationic direct dyes of formula (III') are chosen from the compounds corresponding to structures (III'1) to (111'3) below: (111-1) CHi-N+ CH Ct II2 *and (1113) OH 3 UOH 3 S. S S S S Sn. S S. S S 11 Composition according to Claim 6, characterized in that the cationic direct dyes of formula (IV) are chosen from the compounds 5 corresponding to structures to (IV) 77 below: I CH N. N=N 3 (IV), I OH 3 0 I Ni N=N PI) 2 99 NHCOCH 3 I a N=N -N I- -b ~~CH 3 '3 0 N+ N=N NCH 2 CH 2 OH 4 I aC2CH2O 0 N+ N N /\NH ([V)6 0 HCN N=N (IV) .0 HC'N+ N=N N CA (V)s 0 HCN+ N=N NZV) 3 C- CH 3 (tV) 9 100 CH 3 -OCH 3 OH3 N~ N=N N\ 0 OH 3 2 ~CH 2 N+ N=N \Nl-- I C 2 H 2 CH 3 N+ N=N N 3 CH 3 0 H C N+ N==N /\NH 2 (V) 14 0 CH 3 CHH3 101 CM 3 CN+. N=N N (IS I O H 3 C H 3 N+ N N N N, I CH O 3 (V 0 CH3 NHCOCH-3 7 ~OH 3 7 0H 3 (V 1 N- N=N Nl\(I CH3 HOCN N=N N N (V) 20 I- H 3 a.Ha c 7 IIIH3 H3 CN N=N N 0 N= N 011 (V) 2 0 102 C, H 3 C I CH3 N4 N=N -NZ 3 (tV) 23 I N CH 3 .H3 -N CH N+ N=N 24 0 \1 N= CH 3 (IV) 2 (N N( N+ I N N N N,,C/ I aNH C HH (IV) 2 7 CH 3 aN+ N=N NH 2 ('V)28 I OH CH 3 S0 4 103 aOH 3 N+ N=N NH 2 CH 3 CH 3 S0 4 (IV)29 CH 3 N+ N=N OH 2 CH 2 OH CH 2 CH 2 0H 30 U11 3 CH 3 so 4 OH aN+ NN N -G N 2 1 2 OH 3 31 CH 3 S0 4 S S S. S **S S. S S. J=N CH N 3 -a CH3 CH 3 S0 4 CIH 32 (I'/)33 UH 3 CH 3 S0 4 104 H 3Cn N+ N- CH 3 CH 3 S0 4 UH 3 CH 3 S0 4 (tV) 34 (tV) 3 (IV) 36 (t\0 3 7 NHCOCH 3 CHCH CHaS0 4 *0p* .0* V V V V V N-i CH 3 SO 4 OH 3 NOH 3 (P1) 38 CH 3 S0 4 OH 3 V V V. V VV V. 105 H 3 C NN=N N.IIC NN+ C 2 H C H4o 2C5H4 39 INt CH 3 S0 4 CH 3 40 (IV) 4 2 CH 3 S0 4 OH 3 *0 *0 0 0000 0000 0 0000 0000 0 @0 00 0 0000 00 0 000 0 0000 00 00 0 @000 00 00 0 C H to- C; 2 H H 3 C IN CH 3 (N Y Br 43 0 000000 0 00 0 00 0 00 106 N OH 3 N1+ N N (IV)44 OCH 3 N CH 3 SO C 0 H N+ N N (IV) 4 I N o 0 H a N =N NICH 3 N NIO N H (IV)46 OH3 14"'H CH3 N I OH3 N+ NN (V) 4 NH 2 OH 3 3 I I'N(I) *H LitN~-] 107 S 0 H 3 C XN4-' N= N H(1\1)5 OH N=N NH (iV) 5 1 CH 3 OH I "N N=N NH (Mi) 7 CIO; OH N=N NH 2 0 .OCH 3 CH3 I N+ N=N /\OH ('V)54 0 NHCOCH 3 CH 3 I a N+ N=N NH 2 (IV) 5 3 OCHt 3 CI- C 4 NH 2 108 CH 3 0 NH 2 CH 3 I N+ N=N OH (IV) 57 I 0 CH 3 I- N N=N /N H(V)59 C 3H H 3 C~ NCH3 I I CH OH 3 I N+ N=-N H3 (IV)el CH 0 NN 109 =N 2 OH ('V)62 I 0 IN 0 2 N OCH3 -CH 3 VS I aN N=N N/OH3 (V6 00H 3 O 3 CH 3 SO 4 NO 2 OH 3 CC3O N+ N=N OH (V 6 0 OH 3 OH 3 N OH 3 N+ N=N OH ('V)66 OH 3 .0 /GH 3 N N=N I /l H OH 3 67 I NH 2 H3CH 3 SO 4 POSCHO CHO N+ HO HO HO:: 0 Z9A1) +-N HN N=N N:. HO 0 N H 0 HO 0 z HN N N ZHN. -1OSCHO H N OH £HOO 0 H N NOH0 "(Al N=N +N 0 OTT OCH 3 NN=N -O NH 2 NH 2 (IV) 74 1 CH 3 SO 4 UOH 3 _0 NH 2 (N N H 2 (tV) 7 1 CH 3 SO 4 OH 3 OH 3 N CH 3 N=N NH 2 76 0 *NH 2 and N~/CH 3 H 3 N02(tV) 7 I CH 3 SO NO OHM 3
12. Composition according--to any one of the preceding claims, characterized in that the S. pyrazolo[1,5-alpyrimidile(s) and/or the addition salt(s) thereof with an acid or with a base represent(s) from 0.0005 to 12% by weight relative to the total weight of the dye composition. 4 112
13. Composition according to Claim 12, characterized in that the and/or the addition salt(s) thereof with an acid or with a base represent(s) from 0.005 to 6% by weight relative to the total weight of the dye composition.
14. Composition according to any one of the preceding claims, characterized in that the cationic direct dye(s) represent(s) from 0.001. to 10% by weight relative to the total weight of the dye composition.
15. Composition according to Claim 14, characterized in that the cationic direct dye(s) represent(s) from 0.005 to 5% by weight relative to the total weight of the dye composition.
16. Composition according to any one of the 15 preceding claims, characterized in that it contains one or more couplers chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and 20 pyrazolones, and the addition salts thereof with an acid.
17. Composition according to any one 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. 113 Composition according to Claim 17, characterized in that the additional oxidation base(s) is (are) chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho- aminophenols and heterocyclic bases.
19. Composition according to any one of the preceding claims, characterized in that the addition salts with an acid are chosen from the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates, and in that the addition salts with a base are chosen from those obtained with sodium hydroxide, potassium hydroxide, aqueous ammonia or amines.
20. Process for the oxidation dyeing of 15 keratin fibres, and in particular of human keratin fibres such as the hair, characterized in that at least 1 S one dye composition as defined in any one of Claims 1 to 19 is applied to the said fibres, and in that the colour is developed at acidic, neutral or alkaline pH 20 using a non-enzymatic oxidizing agent which is added to the dye composition only at the time of use or which is present in an oxidizing composition that is applied simultaneously or sequentially.
21. Process according to Claim characterized in that the oxidizing agent is chosen from 4k 0 114 hydrogen peroxide, urea peroxide, alkali metal bromates, peracids and persalts.
22.. Multi-compartment dyeing device or multi-compartment dyeing "kit", a first compartment of which contains a dye composition as defined in any one of Claims 1 to 19 and a second compartment of which contains an oxidizing composition containing a non- enzymatic oxidizing agent. Dated this 21st day of October 1999 L'OREAL By their Patent Attorneys GRIFFITH HACK Fellows Institute of Patent and Trade Mark Attorneys of Australia
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR98/13866 | 1998-11-04 | ||
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5600699A true AU5600699A (en) | 2000-05-25 |
| AU730455B2 AU730455B2 (en) | 2001-03-08 |
Family
ID=9532348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU56006/99A Ceased AU730455B2 (en) | 1998-11-04 | 1999-10-21 | Dye composition containing a cationic direct dye and a pyrazolo(1,5-a)pyrimidine as oxidation base, and dyeing processes |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0998908A3 (en) |
| JP (1) | JP2000178147A (en) |
| KR (1) | KR100372377B1 (en) |
| CN (1) | CN1203837C (en) |
| AR (1) | AR019494A1 (en) |
| AU (1) | AU730455B2 (en) |
| BR (1) | BR9907313A (en) |
| CA (1) | CA2288253A1 (en) |
| CZ (1) | CZ373299A3 (en) |
| FR (1) | FR2785183B1 (en) |
| HU (1) | HUP9904016A3 (en) |
| PL (1) | PL336379A1 (en) |
| RU (1) | RU2185811C2 (en) |
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| DE102007031202A1 (en) | 2007-07-04 | 2009-03-19 | Henkel Ag & Co. Kgaa | New protein hydrolysate obtained from wool of Vicugna useful as laundry detergent, wool detergent, manual dishwashing agent and cosmetic agent, which is useful for treating skin and hair |
| DE102007031661A1 (en) | 2007-07-06 | 2009-01-08 | Henkel Ag & Co. Kgaa | Self-tanning compositions with natural tanning effect |
| DE102007033091A1 (en) | 2007-07-13 | 2009-01-15 | Henkel Ag & Co. Kgaa | Agent with anti-irritating agent |
| DE102007033093A1 (en) | 2007-07-13 | 2009-01-15 | Henkel Ag & Co. Kgaa | Agent with anti-irritating agent |
| DE102007033184A1 (en) | 2007-07-13 | 2009-07-02 | Henkel Ag & Co. Kgaa | Cosmetic composition, useful for the care and preservation of natural functions of keratin fibers and increasing the brightness of keratin fibers, preferably human hairs, comprises a powder of a gemstone or semi-precious stone |
| DE102007033362A1 (en) | 2007-07-16 | 2009-01-22 | Henkel Ag & Co. Kgaa | Agent for dyeing keratinous fibers |
| DE102007034482A1 (en) | 2007-07-20 | 2009-01-22 | Henkel Ag & Co. Kgaa | Oxidative hair treatment with Litchi extract and catechins |
| DE102007036499A1 (en) | 2007-08-01 | 2009-02-05 | Henkel Ag & Co. Kgaa | Natural cosmetic hair treatment agent |
| DE102007036911A1 (en) | 2007-08-06 | 2009-02-12 | Henkel Ag & Co. Kgaa | Hair Dye |
| DE102007037429A1 (en) | 2007-08-08 | 2009-02-12 | Henkel Ag & Co. Kgaa | Styling agent based on aqueous silicone dispersions |
| DE102007037427A1 (en) | 2007-08-08 | 2009-02-12 | Henkel Ag & Co. Kgaa | Evaporator solution and dyeing process |
| DE102007038484A1 (en) | 2007-08-14 | 2009-02-19 | Henkel Ag & Co. Kgaa | Hair treatment agent with bacterial fermentation (s) |
| DE102007039330A1 (en) | 2007-08-20 | 2009-02-26 | Henkel Ag & Co. Kgaa | Hair treatment agents |
| DE102007039954A1 (en) | 2007-08-23 | 2009-02-26 | Henkel Ag & Co. Kgaa | Reductive discoloration of keratinous fibers |
| DE102007040314A1 (en) | 2007-08-24 | 2009-02-26 | Henkel Ag & Co. Kgaa | Kit for providing colorants |
| DE102007040313A1 (en) | 2007-08-24 | 2009-02-26 | Henkel Ag & Co. Kgaa | Hair treatment agents |
| DE102007041492A1 (en) | 2007-08-31 | 2009-03-05 | Henkel Ag & Co. Kgaa | Bleaching agent with delayed Blleichbeginn |
| DE102007041493A1 (en) | 2007-08-31 | 2009-03-05 | Henkel Ag & Co. Kgaa | pastel color |
| DE102007041490A1 (en) | 2007-08-31 | 2009-03-05 | Henkel Ag & Co. Kgaa | Blondiermittel and Blondierverfahren |
| DE102007042286A1 (en) | 2007-09-06 | 2009-03-12 | Henkel Ag & Co. Kgaa | Colorants with natural dyes and 1,3-dihydroxyacetone |
| DE102007045974A1 (en) | 2007-09-25 | 2009-04-09 | Henkel Ag & Co. Kgaa | Biotin and silica against hair aging |
| DE102007046628A1 (en) | 2007-09-27 | 2009-04-02 | Henkel Ag & Co. Kgaa | Hair dyeing process with oxidative pretreatment |
| DE102007047688A1 (en) | 2007-10-04 | 2009-04-09 | Henkel Ag & Co. Kgaa | Brightening agent with cationic 3,4-Dihydroisochinoliniumderivaten and hydrogen peroxide |
| DE102007047685A1 (en) | 2007-10-04 | 2008-07-31 | Henkel Ag & Co. Kgaa | Product for lightening the color of keratinic fibers, especially hair, comprises an acylpyridinium derivative, an imidazole compound and hydrogen peroxide |
| DE102007047687A1 (en) | 2007-10-04 | 2009-04-09 | Henkel Ag & Co. Kgaa | Hair treatment preparations, in particular styling agents, containing two copolymers |
| DE102007048140A1 (en) | 2007-10-05 | 2009-04-09 | Henkel Ag & Co. Kgaa | Oxidative hair treatment with reduced hair damage |
| DE102007050766A1 (en) | 2007-10-22 | 2009-04-23 | Henkel Ag & Co. Kgaa | Process for the continuous production of coloring agents for keratinic fibers |
| DE102008038138A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fibers, which are fur, wool or feathers, preferably human hair, comprises a dye starting product and a browning product, where the browning product is obtained by heating sugar |
| DE102007053952A1 (en) | 2007-11-09 | 2009-05-14 | Henkel Ag & Co. Kgaa | Agent containing ester compound with wax alcohol component |
| DE102008014368A1 (en) | 2008-03-17 | 2009-10-08 | Henkel Ag & Co. Kgaa | Cosmetic composition for hair treatment, for use e.g. in shampoos, rinses, hair-care products or hair dyes, contains a special flavonoid and a vitamin of the B group, especially tiliroside and pantolactone |
| EP2057979A1 (en) | 2007-11-09 | 2009-05-13 | Henkel AG & Co. KGaA | Coloured hair treatment substance |
| DE102007053950A1 (en) | 2007-11-09 | 2009-05-14 | Henkel Ag & Co. Kgaa | Agent with bioflavonoid |
| DE102007054708A1 (en) | 2007-11-14 | 2009-05-20 | Henkel Ag & Co. Kgaa | Hair treatment with Litchi extract and imidazole derivatives |
| DE102007054706A1 (en) | 2007-11-14 | 2009-05-20 | Henkel Ag & Co. Kgaa | Hair treatment with Litchi extract and taurine |
| DE102007056934A1 (en) | 2007-11-23 | 2009-05-28 | Henkel Ag & Co. Kgaa | Oxidation colorant for coloring keratin-containing fibers with atmospheric oxygen as the sole oxidant |
| DE102007056935A1 (en) | 2007-11-23 | 2009-05-28 | Henkel Ag & Co. Kgaa | Two-component aerosol hair color |
| DE102007057584A1 (en) | 2007-11-28 | 2009-06-04 | Henkel Ag & Co. Kgaa | Oxidative dyeing process for keratin fibers |
| DE102007058921A1 (en) | 2007-12-05 | 2009-06-10 | Henkel Ag & Co. Kgaa | styling agents |
| DE102007060532A1 (en) | 2007-12-13 | 2009-09-17 | Henkel Ag & Co. Kgaa | Hair conditioning agents with cationic compounds and selected silicones and / or cosmetic oils |
| DE102007060530A1 (en) | 2007-12-13 | 2009-09-17 | Henkel Ag & Co. Kgaa | Hair conditioning agents with cationic behenyl compounds and selected silicones and / or cosmetic oils |
| DE102007060528A1 (en) | 2007-12-13 | 2009-06-18 | Henkel Ag & Co. Kgaa | Hair conditioning compositions containing imidazolines and selected silicones and / or cosmetic oils |
| DE102007061505A1 (en) | 2007-12-18 | 2009-06-25 | Henkel Ag & Co. Kgaa | Toning gel-foam |
| DE102008003361A1 (en) | 2008-01-08 | 2008-11-27 | Henkel Ag & Co. Kgaa | Agent, useful e.g. to color keratin containing fibers, preferably human hairs, comprises a combination of a vinylether compound with a hydrocarbon acid compound, in a cosmetic carrier |
| WO2009103798A1 (en) | 2008-02-22 | 2009-08-27 | Henkel Ag & Co. Kgaa | 9-[4-(amino) phenyl] acridinium salts as cationic direct dyes for coloring keratinous fibers |
| DE102008012059A1 (en) | 2008-02-29 | 2009-09-03 | Henkel Ag & Co. Kgaa | Hair treatment remedy with goji extract |
| DE102008012058A1 (en) | 2008-02-29 | 2009-09-03 | Henkel Ag & Co. Kgaa | Hair treatment with acai extract |
| DE102008012068A1 (en) | 2008-02-29 | 2009-09-10 | Henkel Ag & Co. Kgaa | Hair treatment with cranberry extract |
| DE102008017104A1 (en) | 2008-04-02 | 2009-10-29 | Henkel Ag & Co. Kgaa | Dispenser for stocking and releasing multi-component hair treatment unit, has housing with multiple chambers for respective components, where chambers are separated from each other |
| DE102008018132A1 (en) | 2008-04-09 | 2009-10-15 | Henkel Ag & Co. Kgaa | Cationic direct drawers and agents for dyeing keratinous fibers |
| DE102008019340A1 (en) | 2008-04-16 | 2009-10-22 | Henkel Ag & Co. Kgaa | Hair treatment with cloudberry fruit extract |
| DE102008022710A1 (en) | 2008-05-07 | 2009-11-12 | Henkel Ag & Co. Kgaa | Brightening agent with cationic acylpyridinium derivatives, co-bleach activators and hydrogen peroxide |
| DE102008024030A1 (en) | 2008-05-16 | 2009-11-19 | Henkel Ag & Co. Kgaa | Brightening agent with cationic 3,4-Dihydroisochinoliniumderivaten, special alkanolamines and hydrogen peroxide |
| DE102008027239A1 (en) | 2008-06-06 | 2009-03-19 | Henkel Ag & Co. Kgaa | Agent, useful for oxidative coloring of keratinic fibers, preferably human hair, comprises at least one p-phenylenediamine derivative, as developer component, and further a coupler component |
| DE102008030660A1 (en) | 2008-07-01 | 2010-01-07 | Henkel Ag & Co. Kgaa | Agent for keratin-containing fibers containing at least one specific cellulose and at least one additional film-forming and / or setting polymer |
| DE102008030661A1 (en) | 2008-07-01 | 2010-01-07 | Henkel Ag & Co. Kgaa | Keratin-containing fibers containing at least one specific betaine compound and at least one film-forming and / or setting polymer |
| DE102008030947A1 (en) | 2008-07-02 | 2009-05-07 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fibers, preferably human hairs, animal hairs, wool, horse hair, angora hair, fur, feathers or textiles, comprises 4-(3-(1H-pyridin-4-ylidene)-cyclopenta-1,4-dienyl)-pyridinium compound as a direct dye |
| DE102008031715A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031701A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031748A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031749A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031700A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031702A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031726A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031556A1 (en) | 2008-07-07 | 2009-04-30 | Henkel Ag & Co. Kgaa | Composition, useful e.g. as shampoo, hair coloring agent, lotion and gel or cream, comprises e.g. tyrosine and/or its derivative, protein hydrolysate, adenosine-triphosphate and a substance comprising riboflavin and lyxoflavin |
| DE102008032178A1 (en) | 2008-07-09 | 2010-01-21 | Henkel Ag & Co. Kgaa | Yellow-oxidized oxidation colorants of highly ethoxylated fatty alcohols and polysaccharide thickener for pH reduced express dyeing |
| DE102008032208A1 (en) | 2008-07-09 | 2010-01-14 | Henkel Ag & Co. Kgaa | Oxidation stain with basic amino acid, ammonium sulfate and alkanolamines |
| DE102008033875A1 (en) | 2008-07-18 | 2009-05-07 | Henkel Ag & Co. Kgaa | Agent, useful for oxidative coloring of keratin fibers, preferably e.g. human hairs, comprises 6-amino-2-hydroxy-pyridine derivative, as coupler component, in a carrier, further developer component and direct dye |
| DE102008034845A1 (en) | 2008-07-24 | 2010-02-04 | Henkel Ag & Co. Kgaa | Composition, useful e.g. for coloring and/or lightening keratin fibers, preferably human hair, comprises color-modifying component in a carrier and further contains a combination of thiolactic acid and/or its salt, and functional additive |
| DE102008035861A1 (en) | 2008-08-01 | 2009-06-04 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fiber, preferably human hair, comprises at least one new or known 1-hydroxyalkyl-3,5-diaminobenzene compound as a coupler component in a cosmetic acceptable carrier |
| DE102008036535A1 (en) | 2008-08-06 | 2010-02-11 | Henkel Ag & Co. Kgaa | Coloration with cationizable polymer |
| DE102008036717A1 (en) | 2008-08-07 | 2010-02-11 | Henkel Ag & Co. Kgaa | Coloring conditioner |
| DE102008037633A1 (en) | 2008-08-14 | 2010-02-18 | Henkel Ag & Co. Kgaa | Cosmetic composition containing oil from the fruits of the Sumac family |
| DE102008038112A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent for keratin-containing fibers containing at least one specific amphiphilic, cationic polymer and at least one polyol |
| DE102008038107A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent for keratin-containing fibers containing at least one particular amphiphilic cationic polymer and at least one additional film-forming and / or setting polymer selected from chitosan and its derivatives |
| DE102008059479A1 (en) | 2008-11-28 | 2010-06-10 | Henkel Ag & Co. Kgaa | Agent, useful e.g. to treat human hair, comprises an amphiphilic, cationic polymer having pyrrolidin-2-one-, azepan-2-one- or nitrogen containing- structural unit, and a film-forming cationic and/or stabilizing cationic polymer |
| DE102008038110A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Keratin-containing fiber compositions comprising at least one specific amphiphilic cationic polymer and at least one additional special film-forming nonionic and / or setting nonionic polymer |
| DE102008038105A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent for keratin-containing fibers containing at least one specific amphiphilic, cationic polymer and at least one specific amphiphilic, anionic polymer |
| WO2010020500A2 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent for fibres containing keratin, containing at least one specific amphiphilic cationic polymer and at least one additional film-forming cationic and/or stabilizing polymer |
| DE102008038106A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Keratin-containing fiber composition comprising at least one specific amphiphilic cationic polymer and at least one specific additional film-forming anionic and / or setting anionic polymer |
| DE102008059480A1 (en) | 2008-11-28 | 2010-06-02 | Henkel Ag & Co. Kgaa | Agent, useful e.g. to treat keratin fibers, comprises amphiphilic, cationic polymer having e.g. pyrrolidin-2-one structural unit, film-forming cationic/stabilizing cationic polymer, and film-forming non-ionic/stabilizing non-ionic polymer |
| DE102008038104A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent for keratin-containing fibers containing at least one specific amphiphilic cationic polymer and at least one polymer with silicone-containing side chains and anionic groups |
| DE102008038109A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent, useful e.g. to treat keratin fibers, especially human hair, comprises amphiphilic, cationic polymer comprising e.g. pyrrolidin-2-one unit, and amine unit, and film-forming cationic and/or solid cationic polymer in a carrier |
| WO2010020505A2 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent for fibres containing keratin, comprising at least one specific amphiphilic cationic polymer, at least one cationic styling polymer that is different therefrom and at least one film-forming non-ionic and/or stabilizing non-ionic polymer |
| DE102008044715A1 (en) | 2008-08-28 | 2010-03-04 | Henkel Ag & Co. Kgaa | Cationic acylpyridinium derivatives as bleach activators |
| DE102008044714A1 (en) | 2008-08-28 | 2010-03-04 | Henkel Ag & Co. Kgaa | Cationic dihydroisoquinolinium derivatives as bleach activators |
| DE102008046178A1 (en) | 2008-09-06 | 2010-03-11 | Henkel Ag & Co. Kgaa | Composition, useful for the treatment of skin and keratin fibers (hair), comprises oil extracted from fruits, UV filter e.g. p-aminobenzoic acid, compound having film-forming properties e.g. vitamin B5, and cosmetic carrier |
| DE102008046433A1 (en) | 2008-09-09 | 2010-03-11 | Henkel Ag & Co. Kgaa | Brightening agent with 2-acylpyridinium derivatives |
| DE102008046882A1 (en) | 2008-09-11 | 2010-03-18 | Henkel Ag & Co. Kgaa | Hair treatment agent with chitosan succinamide |
| DE102008046883A1 (en) | 2008-09-11 | 2010-03-18 | Henkel Ag & Co. Kgaa | Hair treatment with spirulina extract |
| DE102008047945A1 (en) | 2008-09-18 | 2009-06-25 | Henkel Ag & Co. Kgaa | Cosmetic or dermatological composition, useful e.g. for artifical skin tanning or repigmenting hair, includes tyrosine compound and acetyl-methionyl-arginine ethyl ester |
| DE102008048438A1 (en) | 2008-09-23 | 2010-03-25 | Henkel Ag & Co. Kgaa | Compositions for reducing breakage of keratinic fibers |
| DE102008049323A1 (en) | 2008-09-29 | 2010-04-01 | Henkel Ag & Co. Kgaa | New developer components |
| DE102008052618A1 (en) | 2008-10-21 | 2010-04-22 | Henkel Ag & Co. Kgaa | Tricyclic aldehydes and C, H-acidic compounds |
| DE102008061857A1 (en) | 2008-10-22 | 2010-04-29 | Henkel Ag & Co. Kgaa | Colorants based on CH-acidic compounds |
| DE102008061855A1 (en) | 2008-10-22 | 2010-04-29 | Henkel Ag & Co. Kgaa | Agent for dyeing keratinous fibers |
| DE102008061863A1 (en) | 2008-10-22 | 2010-04-29 | Henkel Ag & Co. Kgaa | Process for lamination of gray hair |
| DE102008055615A1 (en) | 2008-11-03 | 2010-05-06 | Henkel Ag & Co. Kgaa | Hair dyeing process with after-treatment |
| DE102008056811A1 (en) | 2008-11-11 | 2009-09-17 | Henkel Ag & Co. Kgaa | Agent, useful e.g. for oxidative coloring of keratin fibers e.g. human hair, wool and feathers, comprises substituted 4-aminophenyl compounds and/or their salt as oxidation dyestuff precursor of developer-type in a cosmetic carrier |
| DE102008057018A1 (en) | 2008-11-12 | 2010-07-08 | Henkel Ag & Co. Kgaa | Combination of cationic bleach activators and dyes |
| DE102008058921A1 (en) | 2008-11-25 | 2010-05-27 | Henkel Ag & Co. Kgaa | New dyes |
| DE102008060671A1 (en) | 2008-12-08 | 2010-06-10 | Henkel Ag & Co. Kgaa | Accelerated brightening agents |
| DE102008060670A1 (en) | 2008-12-08 | 2010-06-10 | Henkel Ag & Co. Kgaa | Alternative oxidizers |
| DE102008061342A1 (en) | 2008-12-11 | 2010-06-17 | Henkel Ag & Co. Kgaa | Hair color with cocoa butter |
| DE102008061133A1 (en) | 2008-12-11 | 2010-06-17 | Henkel Ag & Co. Kgaa | Increased lightening with simultaneous hair strengthening |
| DE102008061040A1 (en) | 2008-12-11 | 2010-06-17 | Henkel Ag & Co. Kgaa | Strengthening coloration |
| DE102008061046A1 (en) | 2008-12-11 | 2010-06-17 | Henkel Ag & Co. Kgaa | Hair dye with color indicator |
| DE102008061675A1 (en) | 2008-12-12 | 2009-11-19 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fibers, preferably human hairs, comprises N-(4-amino-3-methylphenyl)-N-(3-(1H-imidazol-1-yl)propyl)amine, as developer component in a carrier |
| DE102008061702A1 (en) | 2008-12-12 | 2009-11-12 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fibers, preferably human hairs, comprises N-(4-amino-3-methylphenyl)-N-(3-(1H-imidazol-1-yl)propyl)amine or its salt, as a developer component, in a cosmetic carrier |
| DE102008061676A1 (en) | 2008-12-12 | 2009-11-19 | Henkel Ag & Co. Kgaa | Agent in a carrier, useful for coloring keratin fibers, preferably human hairs, comprises developer component comprising N-(4-amino-3-methylphenyl)-N-(3-(1H-imidazol-1-yl)propyl)amine in combination with a pyrazole compound |
| DE102008061862A1 (en) | 2008-12-15 | 2010-06-17 | Henkel Ag & Co. Kgaa | Colorants containing specific halogen-substituted catecholaldehydes and special CH-acidic compounds |
| DE102008061860A1 (en) | 2008-12-15 | 2010-06-17 | Henkel Ag & Co. Kgaa | Nourishing hair color |
| DE102008061864A1 (en) | 2008-12-15 | 2010-10-21 | Henkel Ag & Co. Kgaa | Agent, useful for oxidative coloring of keratin fibers e.g. human hair, comprises p-phenylene diamine derivatives, as developer component, in a carrier |
| DE102008061861A1 (en) | 2008-12-15 | 2010-06-17 | Henkel Ag & Co. Kgaa | Nourishing hair color |
| DE102008062239A1 (en) | 2008-12-16 | 2010-06-17 | Henkel Ag & Co. Kgaa | Process for decolorizing keratin-containing fibers |
| DE102008062234A1 (en) | 2008-12-16 | 2009-10-15 | Henkel Ag & Co. Kgaa | Agent, useful e.g. to color keratin fibers including human hairs cotton and silk, comprises a hydrocarbon acid compound and a reactive carbonyl compound in a cosmetic carrier |
| DE102008062236A1 (en) | 2008-12-16 | 2009-10-15 | Henkel Ag & Co. Kgaa | Agent, useful e.g. to color keratin fibers including human hairs cotton and silk, comprises substituted benzene sulfonate compound e.g. 3-methyl-1,3-benzothiazolium-2-sulfonate, and hydrocarbon acid compound in a carrier |
| DE102008062237A1 (en) | 2008-12-16 | 2010-06-17 | Henkel Ag & Co. Kgaa | Reductive discoloration of keratinous fibers |
| DE202009000769U1 (en) | 2009-01-21 | 2009-03-19 | Henkel Ag & Co. Kgaa | New dyes |
| DE102009001576A1 (en) | 2009-03-16 | 2010-01-07 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fibers, preferably human hair, comprises at least a new or known p-phenylenediamine derivate as a developer component in a carrier |
| DE102009001687A1 (en) | 2009-03-20 | 2010-01-14 | Henkel Ag & Co. Kgaa | Agent, useful for dyeing keratin fibers, preferably human hair, comprises a cationic benzo(cd)indolium compound |
| DE102009002729A1 (en) | 2009-04-29 | 2010-11-04 | Henkel Ag & Co. Kgaa | Filmbildner in hair colors |
| DE102009020552A1 (en) | 2009-05-08 | 2010-11-18 | Henkel Ag & Co. Kgaa | Polymer combination of at least two different N-vinylpyrrolidone / N-vinylcaprolactam copolymers for glossy cosmetic hair treatment agents |
| DE102009020553A1 (en) | 2009-05-08 | 2010-11-11 | Henkel Ag & Co. Kgaa | Polymer combination of at least two different N-vinylpyrrolidone / N-vinylcaprolactam copolymers for glossy cosmetic hair treatment agents |
| DE102009026671A1 (en) | 2009-06-03 | 2011-06-16 | Henkel Ag & Co. Kgaa | Composition, useful for coloring keratin fibers, preferably human hair, comprises a p-phenylene diamine compound containing a cyclic acetal group as a developer component in a carrier |
| DE102009026769A1 (en) | 2009-06-05 | 2010-11-25 | Henkel Ag & Co. Kgaa | Agent, useful e.g. for coloring and brightening of keratin fibers, preferably human hairs, and increasing the skin compatibility of colors and/or brighteners, comprises a cationic 9-phenyl-4a,9a-dihydro-acridine salt |
| DE102009027485A1 (en) | 2009-07-06 | 2011-01-13 | Henkel Ag & Co. Kgaa | Foamy colorants |
| DE102009027925A1 (en) | 2009-07-22 | 2011-01-27 | Henkel Ag & Co. Kgaa | Agent for keratin-containing fibers containing at least one acrylate / glyceryl acrylate copolymer, at least one film-forming and / or setting polymer and at least one ester oil |
| DE102009028054A1 (en) | 2009-07-28 | 2011-02-10 | Henkel Ag & Co. Kgaa | Cosmetic agent |
| DE102009028207A1 (en) | 2009-08-04 | 2011-02-17 | Henkel Ag & Co. Kgaa | Hair treatment agent with polyether-modified solid particles and hair-setting polymers |
| DE102009028209A1 (en) | 2009-08-04 | 2011-02-10 | Henkel Ag & Co. Kgaa | Hair treatment compositions with polyether-modified organic compounds and hair-setting polymers |
| DE102009028206A1 (en) | 2009-08-04 | 2011-02-10 | Henkel Ag & Co. Kgaa | Hair treatment products with special polyethers and hair-setting polymers |
| DE102009028523A1 (en) | 2009-08-13 | 2011-02-17 | Henkel Ag & Co. Kgaa | Foamy colorants II |
| DE102009028593A1 (en) | 2009-08-17 | 2011-02-24 | Henkel Ag & Co. Kgaa | Oxidative colorants |
| DE102009029270A1 (en) | 2009-09-08 | 2010-07-01 | Henkel Ag & Co. Kgaa | Agent, useful for coloring and simultaneously brightening of keratin fibers, preferably human hair, comprises 2-phenyl-(1,4)naphthoquinone compounds |
| DE102009045176A1 (en) | 2009-09-30 | 2011-04-07 | Henkel Ag & Co. Kgaa | Heat-assisting reductive decolorization of keratin-containing fibers |
| DE102009045575A1 (en) | 2009-10-12 | 2010-07-29 | Henkel Ag & Co. Kgaa | Agent, useful for dyeing and optionally bleaching keratin fibers, preferably human hair, comprises at least one new or known (1H-benzotriazol-5-yl)-phenyl-diazene compound |
| DE102009045855A1 (en) | 2009-10-20 | 2010-08-05 | Henkel Ag & Co. Kgaa | Agent, useful for coloring and simultaneously brightening of keratin fibers, preferably human hairs, comprises naphthoquinone compounds |
| DE102009045842A1 (en) | 2009-10-20 | 2011-04-21 | Henkel Ag & Co. Kgaa | Polyamides of fatty acid dimers and diamines for hair fixation |
| DE102009045841A1 (en) | 2009-10-20 | 2011-04-21 | Henkel Ag & Co. Kgaa | Cosmetic agent for the reduction of overcrowded, stubborn hair |
| DE102009045840A1 (en) | 2009-10-20 | 2011-04-21 | Henkel Ag & Co. Kgaa | Method for remodeling a hairstyle |
| DE102009045839A1 (en) | 2009-10-20 | 2011-04-21 | Henkel Ag & Co. Kgaa | Polyamides of fatty acid dimers and diamines in combination with special acrylamide copolymers for hair fixation |
| DE102009045925A1 (en) | 2009-10-22 | 2011-04-28 | Henkel Ag & Co. Kgaa | Compositions for shaping keratinic fibers |
| EP2490656B1 (en) | 2009-10-22 | 2017-01-18 | Henkel AG & Co. KGaA | Composition for the treatment of keratinic fibres comprising a nonionic propyleneoxide-modified starch and an anionic polymer |
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| DE102012224143A1 (en) | 2012-12-21 | 2014-06-26 | Henkel Ag & Co. Kgaa | Process for the gentle heat-assisted transformation of keratin-containing fibers |
| US9655828B2 (en) | 2013-02-25 | 2017-05-23 | Merck Patent Gmbh | Glucuronolactone derivatives as self-tanning substances |
| KR102244166B1 (en) | 2013-09-02 | 2021-04-26 | 로레알 | Method for dyeing keratin fibres using cationic styryl disulphide dyes, and composition including said dyes |
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| DE102013226582A1 (en) | 2013-12-19 | 2015-06-25 | Henkel Ag & Co. Kgaa | Oxidative hair dyeing process with the addition of care agents |
| DE102013226587A1 (en) | 2013-12-19 | 2015-06-25 | Henkel Ag & Co. Kgaa | Oxidation dye with reduced hair damage |
| DE102014206532A1 (en) | 2014-04-04 | 2015-10-08 | Henkel Ag & Co. Kgaa | Fashionable aerosol dyes |
| US10494527B2 (en) * | 2015-03-19 | 2019-12-03 | Basf Se | Cationic direct dyes |
| CA3034705C (en) | 2016-08-31 | 2021-08-03 | Agios Pharmaceuticals, Inc. | Inhibitors of cellular metabolic processes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2586913B1 (en) * | 1985-09-10 | 1990-08-03 | Oreal | PROCESS FOR FORMING IN SITU A COMPOSITION CONSISTING OF TWO SEPARATELY PACKED PARTS AND DISPENSING ASSEMBLY FOR THE IMPLEMENTATION OF THIS PROCESS |
| DE4029324A1 (en) * | 1990-09-15 | 1992-03-19 | Henkel Kgaa | Hair Dye |
| FR2750048B1 (en) * | 1996-06-21 | 1998-08-14 | Oreal | KERATIN FIBER DYEING COMPOSITIONS CONTAINING PYRAZOLO- (1, 5-A) -PYRIMIDINE DERIVATIVES, DYEING PROCESS, NOVEL PYRAZOLO- (1, 5-A) -PYRIMIDINE DERIVATIVES AND THEIR PREPARATION METHOD |
| FR2767685B1 (en) * | 1997-09-01 | 2004-12-17 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL AND AN OXIDATION BASE, AND DYEING METHOD |
-
1998
- 1998-11-04 FR FR9813866A patent/FR2785183B1/en not_active Expired - Fee Related
-
1999
- 1999-10-15 EP EP99402549A patent/EP0998908A3/en not_active Withdrawn
- 1999-10-20 CZ CZ19993732A patent/CZ373299A3/en unknown
- 1999-10-21 AU AU56006/99A patent/AU730455B2/en not_active Ceased
- 1999-11-03 AR ARP990105554A patent/AR019494A1/en not_active Application Discontinuation
- 1999-11-03 CN CNB991236688A patent/CN1203837C/en not_active Expired - Fee Related
- 1999-11-03 CA CA002288253A patent/CA2288253A1/en not_active Abandoned
- 1999-11-03 RU RU99123528/14A patent/RU2185811C2/en not_active IP Right Cessation
- 1999-11-03 PL PL99336379A patent/PL336379A1/en not_active Application Discontinuation
- 1999-11-03 KR KR10-1999-0048337A patent/KR100372377B1/en not_active IP Right Cessation
- 1999-11-03 HU HU9904016A patent/HUP9904016A3/en unknown
- 1999-11-04 BR BR9907313-7A patent/BR9907313A/en not_active IP Right Cessation
- 1999-11-04 JP JP11314015A patent/JP2000178147A/en active Pending
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| PL336379A1 (en) | 2000-05-08 |
| BR9907313A (en) | 2000-12-19 |
| CN1203837C (en) | 2005-06-01 |
| AU730455B2 (en) | 2001-03-08 |
| HUP9904016A3 (en) | 2000-11-28 |
| AR019494A1 (en) | 2002-02-20 |
| KR20000035201A (en) | 2000-06-26 |
| FR2785183A1 (en) | 2000-05-05 |
| FR2785183B1 (en) | 2002-04-05 |
| JP2000178147A (en) | 2000-06-27 |
| CZ373299A3 (en) | 2000-05-17 |
| EP0998908A3 (en) | 2000-06-07 |
| CA2288253A1 (en) | 2000-05-04 |
| RU2185811C2 (en) | 2002-07-27 |
| HUP9904016A2 (en) | 2000-08-28 |
| KR100372377B1 (en) | 2003-02-17 |
| EP0998908A2 (en) | 2000-05-10 |
| HU9904016D0 (en) | 2000-01-28 |
| CN1252988A (en) | 2000-05-17 |
| MX9910062A (en) | 2000-09-01 |
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