AU7660498A - Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition - Google Patents
Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition Download PDFInfo
- Publication number
- AU7660498A AU7660498A AU76604/98A AU7660498A AU7660498A AU 7660498 A AU7660498 A AU 7660498A AU 76604/98 A AU76604/98 A AU 76604/98A AU 7660498 A AU7660498 A AU 7660498A AU 7660498 A AU7660498 A AU 7660498A
- Authority
- AU
- Australia
- Prior art keywords
- derivatives
- composition according
- chosen
- acid
- addition salts
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 131
- 238000004043 dyeing Methods 0.000 title claims abstract description 43
- 230000003647 oxidation Effects 0.000 title claims abstract description 31
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 31
- 102000011782 Keratins Human genes 0.000 title claims abstract description 27
- 108010076876 Keratins Proteins 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
- 210000004209 hair Anatomy 0.000 claims abstract description 34
- 102000004190 Enzymes Human genes 0.000 claims abstract description 19
- 108090000790 Enzymes Proteins 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 23
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 22
- 108090000854 Oxidoreductases Proteins 0.000 claims description 21
- 102000004316 Oxidoreductases Human genes 0.000 claims description 21
- -1 monocyclic pyridine compounds Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 108010092464 Urate Oxidase Proteins 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical class C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 6
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical class N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 claims description 6
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 6
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 6
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 6
- 150000001556 benzimidazoles Chemical class 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
- 150000002475 indoles Chemical class 0.000 claims description 6
- 229940116269 uric acid Drugs 0.000 claims description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical compound O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 claims description 5
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 claims description 5
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical class C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 claims description 5
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 claims description 5
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical class N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1h-pyrazole-4,5-diamine Chemical compound NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 claims description 4
- QFMKQGSXHNDVSX-UHFFFAOYSA-N 2h-pyrrolo[3,2-d][1,3]thiazole Chemical compound C1=CC2=NCSC2=N1 QFMKQGSXHNDVSX-UHFFFAOYSA-N 0.000 claims description 4
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 150000002476 indolines Chemical class 0.000 claims description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
- 150000003230 pyrimidines Chemical class 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- QRMLLECAADTTHG-UHFFFAOYSA-N 2h-pyrrolo[3,2-d][1,3]oxazole Chemical class C1=CC2=NCOC2=N1 QRMLLECAADTTHG-UHFFFAOYSA-N 0.000 claims description 3
- VHHWHDFVZGPKRT-UHFFFAOYSA-N 5h-pyrazolo[3,4-d][1,3]thiazole Chemical class N1=NC2=NCSC2=C1 VHHWHDFVZGPKRT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- RQKQKYICHBSFNX-UHFFFAOYSA-N (4,5-diamino-1-ethylpyrazol-3-yl)methanol Chemical compound CCN1N=C(CO)C(N)=C1N RQKQKYICHBSFNX-UHFFFAOYSA-N 0.000 claims description 2
- LHGUPKWTLOUVPW-UHFFFAOYSA-N (4,5-diamino-1-methylpyrazol-3-yl)methanol Chemical compound CN1N=C(CO)C(N)=C1N LHGUPKWTLOUVPW-UHFFFAOYSA-N 0.000 claims description 2
- DPTWQNJCRFZYPL-UHFFFAOYSA-N (4,5-diamino-1-propan-2-ylpyrazol-3-yl)methanol Chemical compound CC(C)N1N=C(CO)C(N)=C1N DPTWQNJCRFZYPL-UHFFFAOYSA-N 0.000 claims description 2
- ZJMUBINEQIUUPL-UHFFFAOYSA-N 1-butylbenzimidazol-4-ol Chemical compound C1=CC=C2N(CCCC)C=NC2=C1O ZJMUBINEQIUUPL-UHFFFAOYSA-N 0.000 claims description 2
- ZTENTJNRKHDCMC-UHFFFAOYSA-N 1-methylbenzimidazole-4,7-diol Chemical compound C1=CC(O)=C2N(C)C=NC2=C1O ZTENTJNRKHDCMC-UHFFFAOYSA-N 0.000 claims description 2
- HISBLXCPAMBVLZ-UHFFFAOYSA-N 1-methylbenzimidazole-5,6-diol Chemical compound OC1=C(O)C=C2N(C)C=NC2=C1 HISBLXCPAMBVLZ-UHFFFAOYSA-N 0.000 claims description 2
- OOOVRUXKQGYTPJ-UHFFFAOYSA-N 1-methylindol-6-ol Chemical compound C1=C(O)C=C2N(C)C=CC2=C1 OOOVRUXKQGYTPJ-UHFFFAOYSA-N 0.000 claims description 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 2
- WTFWZOSMUGZKNZ-UHFFFAOYSA-N 1H-indol-7-amine Chemical compound NC1=CC=CC2=C1NC=C2 WTFWZOSMUGZKNZ-UHFFFAOYSA-N 0.000 claims description 2
- NZJKEQFPRPAEPO-UHFFFAOYSA-N 1h-benzimidazol-4-amine Chemical compound NC1=CC=CC2=C1N=CN2 NZJKEQFPRPAEPO-UHFFFAOYSA-N 0.000 claims description 2
- DODRSIDSXPMYQJ-UHFFFAOYSA-N 1h-benzimidazol-4-ol Chemical compound OC1=CC=CC2=C1N=CN2 DODRSIDSXPMYQJ-UHFFFAOYSA-N 0.000 claims description 2
- LCYKFWZACWTNDC-UHFFFAOYSA-N 1h-benzimidazole-4,7-diol Chemical compound OC1=CC=C(O)C2=C1N=CN2 LCYKFWZACWTNDC-UHFFFAOYSA-N 0.000 claims description 2
- MIMYTSWNVBMNRH-UHFFFAOYSA-N 1h-indol-6-amine Chemical compound NC1=CC=C2C=CNC2=C1 MIMYTSWNVBMNRH-UHFFFAOYSA-N 0.000 claims description 2
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 claims description 2
- ORVPXPKEZLTMNW-UHFFFAOYSA-N 1h-indol-7-ol Chemical compound OC1=CC=CC2=C1NC=C2 ORVPXPKEZLTMNW-UHFFFAOYSA-N 0.000 claims description 2
- OWWAUBQOFLVUMS-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-ol Chemical compound OC1=CC=CC2=C1CCN2 OWWAUBQOFLVUMS-UHFFFAOYSA-N 0.000 claims description 2
- UMXPKGQJQAQXLU-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-amine Chemical compound NC1=CC=C2CCNC2=C1 UMXPKGQJQAQXLU-UHFFFAOYSA-N 0.000 claims description 2
- JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 claims description 2
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 claims description 2
- VFFKUMJVZWLOQM-UHFFFAOYSA-N 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=C(C)C=NC2=C(N)C(C)=NN21 VFFKUMJVZWLOQM-UHFFFAOYSA-N 0.000 claims description 2
- LGZOJZFHAJJLCF-UHFFFAOYSA-N 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine Chemical compound CC1=CC(N)=NC2=C(N)C(C)=NN21 LGZOJZFHAJJLCF-UHFFFAOYSA-N 0.000 claims description 2
- RHIPXPBQVGXJNL-UHFFFAOYSA-N 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)amino]ethanol Chemical compound OCCNC1=CC=NC2=C(N)C=NN21 RHIPXPBQVGXJNL-UHFFFAOYSA-N 0.000 claims description 2
- HARBPHQCTIDSBX-UHFFFAOYSA-N 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)amino]ethanol Chemical compound NC1=CC=NC2=C(NCCO)C=NN12 HARBPHQCTIDSBX-UHFFFAOYSA-N 0.000 claims description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 2
- AJZRIOLJTXDFDY-UHFFFAOYSA-N 2-benzyl-5-methylpyrazole-3,4-diamine Chemical compound NC1=C(N)C(C)=NN1CC1=CC=CC=C1 AJZRIOLJTXDFDY-UHFFFAOYSA-N 0.000 claims description 2
- URPJUMVYJFHGOR-UHFFFAOYSA-N 2-benzylpyrazole-3,4-diamine Chemical compound NC1=C(N)C=NN1CC1=CC=CC=C1 URPJUMVYJFHGOR-UHFFFAOYSA-N 0.000 claims description 2
- LRFYRWUMJLXTJH-UHFFFAOYSA-N 2-ethyl-5-(4-methoxyphenyl)pyrazole-3,4-diamine Chemical compound NC1=C(N)N(CC)N=C1C1=CC=C(OC)C=C1 LRFYRWUMJLXTJH-UHFFFAOYSA-N 0.000 claims description 2
- MEKRUGGNBTYVRV-UHFFFAOYSA-N 2-ethyl-5-methylpyrazole-3,4-diamine Chemical compound CCN1N=C(C)C(N)=C1N MEKRUGGNBTYVRV-UHFFFAOYSA-N 0.000 claims description 2
- USVXDODAPOBXCF-UHFFFAOYSA-N 2-methyl-1h-benzimidazol-4-amine Chemical compound C1=CC=C2NC(C)=NC2=C1N USVXDODAPOBXCF-UHFFFAOYSA-N 0.000 claims description 2
- HLPAESMITTURFN-UHFFFAOYSA-N 2-methyl-1h-benzimidazol-4-ol Chemical compound C1=CC=C2NC(C)=NC2=C1O HLPAESMITTURFN-UHFFFAOYSA-N 0.000 claims description 2
- AXUDYYPUJZTLSH-UHFFFAOYSA-N 2-methyl-1h-benzimidazole-5,6-diol Chemical compound OC1=C(O)C=C2NC(C)=NC2=C1 AXUDYYPUJZTLSH-UHFFFAOYSA-N 0.000 claims description 2
- XBVSGEGNQZAQPM-UHFFFAOYSA-N 2-methyl-1h-indol-4-ol Chemical compound C1=CC=C2NC(C)=CC2=C1O XBVSGEGNQZAQPM-UHFFFAOYSA-N 0.000 claims description 2
- XOAXOKSJNVLLHZ-UHFFFAOYSA-N 2-methylpyrazole-3,4-diamine Chemical compound CN1N=CC(N)=C1N XOAXOKSJNVLLHZ-UHFFFAOYSA-N 0.000 claims description 2
- MWXUGXZKBKIMKB-UHFFFAOYSA-N 2-methylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C(C)=NN21 MWXUGXZKBKIMKB-UHFFFAOYSA-N 0.000 claims description 2
- UVUGDGRIYQQKIT-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-amine Chemical compound O1CCNC2=CC(N)=CC=C21 UVUGDGRIYQQKIT-UHFFFAOYSA-N 0.000 claims description 2
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 claims description 2
- BGMAIXRJQFTHIH-UHFFFAOYSA-N 3-amino-4H-pyrazolo[1,5-a]pyrimidin-5-one Chemical compound C1=CC(O)=NC2=C(N)C=NN21 BGMAIXRJQFTHIH-UHFFFAOYSA-N 0.000 claims description 2
- FBPSBGSWWFBXQB-UHFFFAOYSA-N 4,7-dimethoxy-1h-benzimidazole Chemical compound COC1=CC=C(OC)C2=C1N=CN2 FBPSBGSWWFBXQB-UHFFFAOYSA-N 0.000 claims description 2
- LUNUNJFSHKSXGQ-UHFFFAOYSA-N 4-Aminoindole Chemical compound NC1=CC=CC2=C1C=CN2 LUNUNJFSHKSXGQ-UHFFFAOYSA-N 0.000 claims description 2
- WLSFMPWGCOPING-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1,4-benzoxazin-6-ol Chemical compound C1=C(O)C=C2N(C)CCOC2=C1 WLSFMPWGCOPING-UHFFFAOYSA-N 0.000 claims description 2
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 claims description 2
- BTWUUHKQHOSMIN-UHFFFAOYSA-N 5,6-dimethoxy-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC2=C1NC=N2 BTWUUHKQHOSMIN-UHFFFAOYSA-N 0.000 claims description 2
- DMBUAGDHNUPLRA-UHFFFAOYSA-N 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=C(C)C(C)=NC2=C(N)C=NN21 DMBUAGDHNUPLRA-UHFFFAOYSA-N 0.000 claims description 2
- GFJCGXFXOXSUJX-UHFFFAOYSA-N 5-butyl-1h-pyrazole Chemical compound CCCCC1=CC=NN1 GFJCGXFXOXSUJX-UHFFFAOYSA-N 0.000 claims description 2
- URGMLVWXPXSAKY-UHFFFAOYSA-N 5-methyl-1h-indol-4-ol Chemical compound CC1=CC=C2NC=CC2=C1O URGMLVWXPXSAKY-UHFFFAOYSA-N 0.000 claims description 2
- JSVCLRZBHIRDNZ-UHFFFAOYSA-N 5-methyl-2-phenylpyrazole-3,4-diamine Chemical compound NC1=C(N)C(C)=NN1C1=CC=CC=C1 JSVCLRZBHIRDNZ-UHFFFAOYSA-N 0.000 claims description 2
- CGTQMHXEGLHVFE-UHFFFAOYSA-N 5-methyl-2-propan-2-ylpyrazole-3,4-diamine Chemical compound CC(C)N1N=C(C)C(N)=C1N CGTQMHXEGLHVFE-UHFFFAOYSA-N 0.000 claims description 2
- NYEINRQDXMWWDE-UHFFFAOYSA-N 5-tert-butyl-2-methylpyrazole-3,4-diamine Chemical compound CN1N=C(C(C)(C)C)C(N)=C1N NYEINRQDXMWWDE-UHFFFAOYSA-N 0.000 claims description 2
- TUYBCLHMZFLWRY-UHFFFAOYSA-N 6-bromo-1,3-benzodioxol-5-ol Chemical compound C1=C(Br)C(O)=CC2=C1OCO2 TUYBCLHMZFLWRY-UHFFFAOYSA-N 0.000 claims description 2
- BKYQHRSVSLQLLQ-UHFFFAOYSA-N 6-methoxy-1,3-benzodioxol-5-amine Chemical compound C1=C(N)C(OC)=CC2=C1OCO2 BKYQHRSVSLQLLQ-UHFFFAOYSA-N 0.000 claims description 2
- ULRSUUNKPNRHQW-UHFFFAOYSA-N 7-methyl-3h-benzimidazol-4-ol Chemical compound CC1=CC=C(O)C2=C1N=CN2 ULRSUUNKPNRHQW-UHFFFAOYSA-N 0.000 claims description 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- RVWZJQLGEUQYMT-UHFFFAOYSA-N N1=C(C)C=C(O)N2N=CC(N)=C21 Chemical compound N1=C(C)C=C(O)N2N=CC(N)=C21 RVWZJQLGEUQYMT-UHFFFAOYSA-N 0.000 claims description 2
- PKACFTKQQUDJDA-UHFFFAOYSA-N OC1=CC=NC2=C(N)C=NN21 Chemical compound OC1=CC=NC2=C(N)C=NN21 PKACFTKQQUDJDA-UHFFFAOYSA-N 0.000 claims description 2
- 102000003992 Peroxidases Human genes 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- VGSVNUGKHOVSPK-UHFFFAOYSA-N leukoaminochrome Chemical compound C1=C(O)C(O)=CC2=C1NCC2 VGSVNUGKHOVSPK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002906 microbiologic effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- FFNJDUZBKSGSIV-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,5-diamine Chemical compound C1=CC(N)=NC2=C(N)C=NN21 FFNJDUZBKSGSIV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- TVHZGWLQGYIVFQ-UHFFFAOYSA-N 1-(2-hydroxyethylamino)ethanol Chemical compound CC(O)NCCO TVHZGWLQGYIVFQ-UHFFFAOYSA-N 0.000 claims 2
- 150000004986 phenylenediamines Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 claims 1
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 claims 1
- ZOHGOQJROHLKIB-UHFFFAOYSA-N 1h-pyrazol-5-ylhydrazine Chemical compound NNC=1C=CNN=1 ZOHGOQJROHLKIB-UHFFFAOYSA-N 0.000 claims 1
- WSTRPMKCJAVLEW-UHFFFAOYSA-N 2,5-dimethylpyrazolo[1,5-a]pyrimidine Chemical compound N1=C(C)C=CN2N=C(C)C=C21 WSTRPMKCJAVLEW-UHFFFAOYSA-N 0.000 claims 1
- LQAKMSIMGCYOAH-UHFFFAOYSA-N 6-methoxy-3h-benzimidazol-5-ol Chemical compound C1=C(O)C(OC)=CC2=C1NC=N2 LQAKMSIMGCYOAH-UHFFFAOYSA-N 0.000 claims 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 1
- 101000716740 Homo sapiens SR-related and CTD-associated factor 4 Proteins 0.000 claims 1
- 241001484259 Lacuna Species 0.000 claims 1
- 102100020878 SR-related and CTD-associated factor 4 Human genes 0.000 claims 1
- 108040007629 peroxidase activity proteins Proteins 0.000 claims 1
- QRSZMEQQBAGKPH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidin-3-amine Chemical compound C1=CC=NC2=C(N)C=NN21 QRSZMEQQBAGKPH-UHFFFAOYSA-N 0.000 claims 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 2
- 101710157860 Oxydoreductase Proteins 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 79
- 238000007792 addition Methods 0.000 description 24
- 229940088598 enzyme Drugs 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000186074 Arthrobacter globiformis Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 108010015776 Glucose oxidase Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 230000015556 catabolic process Effects 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
- 238000006731 degradation reaction Methods 0.000 description 3
- 235000019420 glucose oxidase Nutrition 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 108010001816 pyranose oxidase Proteins 0.000 description 3
- MQEFDQWUCTUJCP-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=NC(N)=C(N)C(N)=N1 MQEFDQWUCTUJCP-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 108010073450 Lactate 2-monooxygenase Proteins 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
- 108010042687 Pyruvate Oxidase Proteins 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000002535 acidifier Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002610 basifying agent Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 108010090622 glycerol oxidase Proteins 0.000 description 2
- 229920013818 hydroxypropyl guar gum Polymers 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-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
- YBMUVGQKRPSJLS-UHFFFAOYSA-N 1h-benzimidazole-5,6-diol Chemical compound C1=C(O)C(O)=CC2=C1NC=N2 YBMUVGQKRPSJLS-UHFFFAOYSA-N 0.000 description 1
- MRQOOXQWSNRMAM-UHFFFAOYSA-N 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC(C)=NC2=C(N)C(C)=NN21 MRQOOXQWSNRMAM-UHFFFAOYSA-N 0.000 description 1
- ATBJHESGXAEWOU-UHFFFAOYSA-N 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1=CC=NC2=C(N)C=NN21 ATBJHESGXAEWOU-UHFFFAOYSA-N 0.000 description 1
- ZQLZWNDBBQUIEY-UHFFFAOYSA-N 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxyethyl)amino]ethanol Chemical compound NC1=CC=NC2=C(N(CCO)CCO)C=NN12 ZQLZWNDBBQUIEY-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- CMYXTZPTHYRATM-UHFFFAOYSA-N 5-hydrazinyl-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(NN)=C1N CMYXTZPTHYRATM-UHFFFAOYSA-N 0.000 description 1
- YPKBCLZFIYBSHK-UHFFFAOYSA-N 5-methylindole Chemical compound CC1=CC=C2NC=CC2=C1 YPKBCLZFIYBSHK-UHFFFAOYSA-N 0.000 description 1
- ONYNOPPOVKYGRS-UHFFFAOYSA-N 6-methylindole Natural products CC1=CC=C2C=CNC2=C1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000228197 Aspergillus flavus Species 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 102100040443 Keratin, type I cytoskeletal 15 Human genes 0.000 description 1
- 108010066330 Keratin-15 Proteins 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- 101000941356 Nostoc ellipsosporum Cyanovirin-N Proteins 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- RWHNUWWUPZKDQP-UHFFFAOYSA-N hydron;pyridine-2,5-diamine;dichloride Chemical compound Cl.Cl.NC1=CC=C(N)N=C1 RWHNUWWUPZKDQP-UHFFFAOYSA-N 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- PNFZIEOWPDFJBH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C=NN21 PNFZIEOWPDFJBH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/66—Enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- 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
-
- 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
-
- 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
- A61K8/4953—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
Abstract
The invention concerns a ready-for-use keratin fibre oxidation dyeing composition, in particular for human keratin fibres such as hair, comprising, in a medium suitable for dyeing, at least a heterocyclic oxidation dye, at least an oxydoreductase enzyme with 2 electrons in the presence of at least a donor for said enzyme, and the dyeing method using said composition.
Description
1 COMPOSITION FOR THE OXIDATION DYEING OF KERATIN FIBRES AND DYEING PROCESS USING THIS COMPOSITION The invention relates to a composition for the oxidation dyeing of keratin fibres, and in 5 particular human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing, at least one heterocyclic oxidation dye and at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, and 10 to the 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 para 15 aminophenols and heterocyclic bases, 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, can give rise to coloured compounds 20 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, 25 meta-aminophenols, meta-diphenols and certain heterocyclic compounds. I4L 2 The variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained. The so-called "permanent" coloration obtained 5 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, 10 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 15 fibre, which may in fact be differently sensitized (i.e. damaged) between its tip and its root. The oxidation dyeing of keratin fibres is generally carried out in alkaline medium, in the presence of hydrogen peroxide. However, the use of 20 alkaline media in the presence of hydrogen peroxide has the drawback of causing appreciable degradation of the fibres, as well as bleaching of the keratin fibres, which is not always desirable. The oxidation dyeing of keratin fibres can 25 also be carried out using oxidizing systems other than hydrogen peroxide, such as enzymatic systems. Thus, it 7TF 7 5
I,
3 has already been proposed to dye keratin fibres, in particular in patent application EP-A-0,310,675, with compositions comprising an oxidation dye precursor of benzenic type, in combination with enzymes such as 5 pyranose oxidase, glucose oxidase or uricase, in the presence of a donor for the said enzymes. Although being used under conditions which do not result in a degradation of the keratin fibres which is comparable to that caused by the dyes used in the presence of 10 hydrogen peroxide, these dyeing processes nevertheless lead to colorations which are less intense. The Applicant has now discovered that it is possible to obtain novel dyes, which are capable of giving intense colorations without giving rise to any 15 significant degradation or bleaching of keratin fibres, and which are relatively unselective and show good resistance to the various attacking factors to which the hair may be subjected, by combining at least one oxidation base, at least one coupler and at least one 20 enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, the oxidation base(s) and/or the coupler(s) used being chosen from suitably selected heterocyclic compounds. This discovery forms the basis of the present 25 invention. A first subject of the invention is thus a RA4/ 4 ready-to-use composition for the oxidation dyeing of keratin fibres, and in particular human keratin fibres such as the hair, comprising the combination of at least one oxidation base and at least one coupler, 5 characterized in that it comprises, in a medium which is suitable for dyeing, at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, and in that the said oxidation base and/or the said coupler is chosen 10 from heterocyclic compounds with the exclusion of monocyclic pyridine compounds. The ready-to-use dye composition in accordance with the invention gives colorations which are more intense than those obtained with dye 15 compositions containing only benzenic dyes in the presence of an enzyme of 2-electron oxidoreductase type, and of a donor for the said enzyme, which is not the case with a conventional oxidizing system such as hydrogen peroxide. The colorations obtained with the 20 ready-to-use dye composition in accordance with the invention is moreover relatively unselective and has excellent properties of resistance both with respect to atmospheric agents such as light and bad weather and with respect to perspiration and the various treatments 25 to which the hair may be subjected (washing, permanent waving). R-1- 5 A subject of the invention is also a process for the oxidation dyeing of keratin fibres using this ready-to-use dye composition. The 2-electron oxidoreductase(s) used in the 5 ready-to-use dye composition in accordance with the invention can be chosen in particular from pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases. According to the invention, the 2-electron 10 oxidoreductase is preferably chosen from uricases of animal, microbiological or biotechnological origin. By way of example, mention may be made in particular of uricase extracted from boar liver, uricase from Arthrobacter globiformis, as well as 15 uricase from Aspergillus flavus. The 2-electron oxidoreductase(s) can be used in pure crystalline form or in a form diluted in a diluent which is inert with respect to the said 2-electron oxidoreductase. 20 The 2-electron oxidoreductase(s) in accordance with the invention preferably represent(s) from 0.01 to 20% by weight approximately relative to the total weight of the ready-to-use dye composition, and even more preferably from 0.1 to 5% by weight 25 approximately relative to this weight. According to the invention, the term "donor" R1I r .44 6 means the various substrates also necessary for the functioning of the said 2-electron oxidoreductase(s). The nature of the donor (or substrate) for the said enzyme varies depending on the nature of the 5 2-electron oxidoreductase used. For example, as donors for pyranose oxidases, mention may be made of D-glucose, L-sorbose and D-xylose; as a donor for glucose oxidases, mention may be made of D-glucose; as a donor for glycerol oxidases, mention may be made of 10 glycerol and dihydroxyacetone; as donors for lactate oxidases, mention may be made of lactic acid and its salts; as donors for pyruvate oxidases, mention may be made of pyruvic acid and its salts; and finally, as donors for uricases, mention may be made of uric acid 15 and its salts. The donor(s) (or substrate(s)) used in accordance with the invention preferably represent(s) from 0.01 to 20% by weight approximately relative to the total weight of the ready-to-use dye composition in 20 accordance with the invention, and even more preferably from 0.1 to 5% by weight approximately relative to this weight. Among the heterocyclic oxidation bases which can be used in the ready-to-use dye composition 25 according to the invention, mention may be made in particular of pyrimidine derivatives and pyrazole 7 derivatives, and the addition salts thereof with an acid. Among the pyrimidine derivatives, mention may be made more particularly of the compounds described, 5 for example, in German patent DE 2,359,399 or Japanese patents JP 88-169,571 and JP 91-106,059, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triamino pyrimidine and the addition salts thereof with an acid, as well as pyrazolopyrimidine derivatives such as 10 pyrazolo[1,5-a]pyrimidine-3,7-diamine, 2-methylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, pyrazolo[1,5-a]pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine, 15 3-aminopyrazolo[1,5-a]pyrimidin-7-ol, 3-amino 5-methylpyrazolo[1,5-a]pyrimidin-7-ol, 3-aminopyrazolo[1,5-a]pyrimidin-5-ol, 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 3-amino-7-S-hydroxyethylamino-5-methylpyrazolo[1,5-a] 20 pyrimidine, 2-(7-aminopyrazolo[1,5-a]pyrimidin 3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin 7-yl) (2-hydroxyethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin 3-yl) (2-hydroxyethyl)amino]ethanol, 25 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and
RA
8 2,5-N-7,N-7-tetramethylpyrazolo[1,5-apyrimidine 3,7-diamine, and the addition salts thereof and the tautomers thereof, when a tautomeric equilibrium exists. 5 Among the pyrazole derivatives, mention may be made more particularly of the compounds described in patents or patent applications DE 3,843,892, DE 4,133,957, DE 4,234,886, DE 4,234,887, FR 2,733,749, FR 2,735,685, WO 94/08969 and WO 94/08970, such as 10 4,5-diaminopyrazole, 4,5-diamino-1-methylpyrazole, 1-benzyl-4,5-diaminopyrazole, 3,4-diaminopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4-amino 1,3-dimethyl-5-hydrazinopyrazole, 4,5-diamino-3-methyl 1-phenylpyrazole, 4,5-diamino-3-methyl-l-tert 15 butylpyrazole, 4,5-diamino-l-methyl-3-tert butylpyrazole, 4,5-diamino-l-ethyl-3-methylpyrazole, 4,5-diamino-l-ethyl-3-(4'-methoxyphenyl)pyrazole, 4,5-diamino-l-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 20 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole and 4,5-diamino-3-methyl-l-isopropylpyrazole, and the addition salts thereof with an acid. When they are present, the heterocyclic oxidation base(s) in accordance with the invention 25 preferably represent(s) from 0.0005 to 12% by weight approximately relative to the total weight of the 9 ready-to-use dye composition, and even more preferably from 0.005 to 6% by weight approximately relative to this weight. Among the heterocyclic couplers which can be 5 used in the ready-to-use dye composition according to the invention, mention may be made in particular of indole derivatives, indoline derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyrazoloazole derivatives, pyrroloazole 10 derivatives, imidazoloazole derivatives, pyrazolopyrimidine derivatives, pyrazoline-3,5-dione derivatives, pyrrolo[3,2-d]oxazole derivatives, pyrazolo[3,4-d]thiazole derivatives, thiazoloazole S-oxide derivatives and thiazoloazole S,S-dioxide 15 derivatives, and the addition salts thereof with an acid. Among the indole derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made more 20 particularly of the compounds of formula (I) below, and the addition salts thereof with an acid: X N R R3 , 2 R, in which: 7 1 RA4/ 4U 0loqj 10
R
1 represents a hydrogen atom, a Cl-C 4 alkyl radical, a
C
2
-C
4 mono- or polyhydroxyalkyl radical or a
C
1
-C
4 aminoalkyl radical in which the amine is mono- or disubstituted with a Cl-C 4 alkyl group; 5 R 2 represents a hydrogen atom or a Cl-C 4 alkyl radical;
R
3 represents a hydrogen atom or a C,-C 4 alkyl or hydroxyl radical; X represents a hydroxyl radical or a radical NHR 4 in which R 4 represents a hydrogen atom or a Ci-C 4 alkyl or 10 Cl-C 4 hydroxyalkyi radical. Among the indole compounds of formula (I) above, mention may be made more particularly of 4-hydroxyindole, 6-hydroxyindole, 7-aminoindole, 6-aminoindole, 7-hydroxyindole, 7-ethyl 15 6-(S-hydroxyethyl)aminoindole, 4-aminoindole, 6-hydroxy-l-methylindole, 5,6-dihydroxyindole, 4-hydroxy-l-N-methylindole, 4-hydroxy-2-methylindole, 4-hydroxy-5-methylindole, 4-hydroxy-1-N (S-hydroxyethyl)indole, 4-hydroxy 20 1-N-(P-hydroxypropyl)indole, 1-N-(0,y-dihydroxypropyl) 4-hydroxyindole, 4-hydroxy-1-N-(f-hydroxyethyl) 5-methylindole and 1-N-(y-dimethylaminopropyl) 4-hydroxyindole, and the addition salts thereof with an acid. 25 Among the indoline derivatives which can be used as heterocyclic couplers in the dye composition in 11 accordance with the invention, mention may be made in particular of 4-hydroxyindoline, 6-hydroxyindoline, 6-aminoindoline and 5,6-dihydroxyindoline, and the addition salts thereof with an acid. 5 Among the benzimidazole derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made more particularly of the compounds of formula (II) below, and the addition salts thereof with an acid:
R
7
R
5 10 in which:
R
5 represents a hydrogen atom or a C 1
-C
4 alkyl radical, R. represents a hydrogen atom or a C 1
-C
4 alkyl or phenyl radical, R, represents a hydroxyl, amino or methoxy radical, 15 R, represents a hydrogen atom or a hydroxyl, methoxy or
C
1
-C
4 alkyl radical; with the proviso that: - when R, denotes an amino radical, then it occupies position 4, 20 - when R, occupies position 4, then R occupies position 7, 12 - when R, occupies position 5, then R 8 occupies position 6. Among the benzimidazole derivatives of formula (II) above, mention may be made more 5 particularly of 4-hydroxybenzimidazole, 4-aminobenzimidazole, 4-hydroxy-7-methylbenzimidazole, 4-hydroxy-2-methylbenzimidazole, 1-butyl-4-hydroxybenz imidazole, 4-amino-2-methylbenzimidazole, 5,6-dihydroxybenzimidazole, 5-hydroxy-6-methoxybenz 10 imidazole, 4,7-dihydroxybenzimidazole, 4,7-dihydroxy 1-methylbenzimidazole, 4,7-dimethoxybenzimidazole, 5,6-dihydroxy-l-methylbenzimidazole, 5,6-dihydroxy 2-methylbenzimidazole and 5,6-dimethoxybenzimidazole, and the addition salts thereof with an acid. 15 Among the benzomorpholine derivatives which can be used as heterocyclic couplers in the ready-to use dye composition in accordance with the invention, mention may be made more particularly of the compounds of formula (III) below, and the addition salts thereof 20 with an acid: R9 in which: 41 13 R, and R 1 ., which may be identical or different, represent a hydrogen atom or a C,-C 4 alkyl radical, Z represents a hydroxyl or amino radical. Among the benzomorpholine derivatives of 5 formula (III) above, mention may be made more particularly of 6-hydroxy-1, 4 -benzomorpholine, N-methyl-6-hydroxy-1, 4-benzomorpholine and 6-amino 1,4-benzomorpholine, and the addition salts thereof with an acid. 10 Among the sesamol derivatives which can be used as heterocyclic coupler in the ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the compounds of formula (IV) below, and the addition salts thereof with 15 an acid: R R 12 I (IV) 0 in which:
R
11 denotes a hydroxyl, amino, (C 1
-C
4 )alkylamino, monohydroxy (C 1
-C
4 ) alkylamino or polyhydroxy (C 2
-C
4 ) alkylamino radical, 20 R 12 denotes a hydrogen or halogen atom or a C 1
-C
4 alkoxy radical. _4 14 Among the sesamol derivatives of formula (IV) above, mention may be made more particularly of 2-bromo-4,5-methylenedioxyphenol, 2-methoxy 4,5-methylenedioxyaniline and 2-(S-hydroxyethyl)amino 5 4,5-methylenedioxybenzene, and the addition salts thereof with an acid. Among the pyrazoloazole derivatives which can be used as heterocyclic couplers in the ready-to-use dye composition in accordance with the invention, 10 mention may be made more particularly of the compounds described in the following patents and patent applications: FR 2,075,583, EP-A-119,860, EP-A-285,274, EP-A-244,160, EP-A-578,248, GB 1,458,377, US 3,227,554, US 3,419,391, US 3,061,432, US 4,500,630, US 3,725,067, 15 US 3,926,631, US 5,457,210, JP 84/99437, JP 83/42045, JP 84/162548, JP 84/171956, JP 85/33552, JP 85/43659, JP 85/172982, JP 85/190779 and in the following publications: Chem. Ber. 32, 797 (1899), Chem. Ber. 89, 2550, (1956), J. Chem. Soc. Perkin trans I, 2047, 20 (1977), J. Prakt. Chem., 320, 533, (1978); the teachings of which form an integral part of the present application. As pyrazoloazole derivatives, mention may be made most particularly of: 25 - 2-methylpyrazolo[1,5-b]-1,2,4-triazole, - 2-ethylpyrazolo[1,5-b]-1,2,4-triazole, 1 15 - 2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, - 2-phenylpyrazolo[1,5-b]-1,2,4-triazole, - 2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole, - 7-chloro-2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole, 5 - 3,6-dimethylpyrazolo[3,2-c]-1,2,4-triazole, - 6-phenyl-3-methylthiopyrazolo[3,2-c]-1,2,4-triazole and - 6-aminopyrazolo[1,5-a]benzimidazole, and the addition salts thereof with an acid. 10 Among the pyrroloazole derivatives which can be used as heterocyclic couplers in the ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the compounds described in the following patents and patent 15 applications: US 5,256,526, EP-A-557,851, EP-A-578,248, EP-A-518,238, EP-A-456,226, EP-A-488,909, EP-A-488,248, and in the following publications: - D.R. Liljegren Ber. 1964, 3436; - E.J. Browne, J.C.S., 1962, 5149; 20 - P. Magnus, J.A.C.S., 1990, 112, 2465; - P. Magnus, J.A.C.S., 1987, 109, 2711; - Angew. Chem. 1960, 72, 956; - and Rec. Trav. Chim. 1961, 80, 1075; the teachings of which form an integral part of the present application. 25 As pyrroloazole derivatives, mention may be made most particularly of: I 1 16 - 5-cyano-4-ethoxycarbonyl-8-methylpyrrolo[1,2-b] 1,2,4-triazole, - 5-cyano-8-methyl-4-phenylpyrrolo[1,2-b] 1,2,4-triazole, 5 - 7-amido-6-ethoxycarbonylpyrrolo[1,2-a]-benzimidazole, and the addition salts thereof with an acid. Among the imidazoloazole derivatives which can be used as heterocyclic couplers in the ready-to use dye composition in accordance with the invention, 10 mention may be made more particularly of the compounds described in the following patents and patent applications: US 5,441,863; JP 62-279,337; JP 06-236,011 and JP 07-092,632, the teachings of which form an integral part of the present application. 15 As imidazoloazole derivatives, mention may be made most particularly of: - 7,8-dicyanoimidazolo[3,2-a]imidazole, - 7,8-dicyano-4-methylimidazolo[3,2-a]imidazole, and the addition salts thereof with an acid. 20 Among the pyrazolopyrimidine derivatives which can be used as heterocyclic couplers in the ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the compounds described in the following patent 25 application: EP-A-304,001, the teaching of which forms an integral part of the present application.
J/
17 As pyrazolopyrimidine derivatives, mention may be made most particularly of: - pyrazolo[1,5-a]pyrimidin-7-one, - 2,5-dimethylpyrazolo[1,5-alpyrimidin-7-one, 5 - 2-methyl-6-ethoxycarbonylpyrazolo[1,5-a]pyrimidin 7-one, - 2-methyl-5-methoxymethylpyrazolo[1,5-a]pyrimidin 7-one,
-
2 -tert-butyl-5-trifluoromethylpyrazolo[1,5-al 10 pyrimidin-7-one, - 2,7-dimethylpyrazolo[1,5-alpyrimidin-5-one, and the addition salts thereof with an acid. Among the pyrazoline-3,5-dione derivatives which can be used as heterocyclic couplers in the 15 ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the compounds described in the following patents and patent applications: JP 07-036159, JP 07-084348 and US 4,128,425, and in the following publications: 20 - L. WYZGOWSKA, Acta. Pol. Pharm. 1982, 39 (1-3), 83 - E. HANNIG, Pharmazie, 1980, 35 (4), 231 - M.H. ELNAGDI, Bull. Chem. Soc. Jap., 46 (6), 1830, 1973 - G. CARDILLO, Gazz. Chim. Ital. 1966, 96, (8-9), 973, 25 the teachings of which form an integral part of the present application.
18 As pyrazoline-3,5-dione derivatives, mention may be made most particularly of: - 1, 2 -diphenylpyrazoline-3,5-dione, - 1, 2 -diethylpyrazoline-3,5-dione, 5 and the addition salts thereof with an acid. Among the pyrrolo[3,2-d]oxazole derivatives which can be used as heterocyclic couplers in the ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the 10 compounds described in patent application JP 07-325,375, the teaching of which forms an integral part of the present application. Among the pyrazolo[3,4-d]thiazole derivatives which can be used as heterocyclic couplers in the 15 ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the compounds described in patent application JP 07-244,361 and in J. Heterocycl. Chem. 16, 13, (1979). Among the thiazoloazole S-oxide and 20 thiazoloazole S,S-dioxide derivatives which can be used as heterocyclic couplers in the ready-to-use dye composition in accordance with the invention, mention may be made more particularly of the compounds described in the following documents: 25 - JP 07-098489; - Khim. Geterotsilk. Soedin, 1967, p. 93; '1
"I
19 - J. Prakt. Chem., 318, 1976, p. 12; - Indian J. Heterocycl. Chem. 1995, 5, (2), p. 135; - Acta. Pol. Pharm. 1995, 52 (5), 415; - Heterocycl. Commun. 1995, 1 (4), 297; 5 - Arch. Pharm. (Weinheim, Ger.), 1994, 327 (12), 825. When they are present, this or these heterocyclic coupler(s) preferably represent(s) from 0.0001 to 10% by weight approximately relative to the total weight of the ready-to-use dye composition and 10 even more preferably from 0.005 to 5% by weight approximately relative to this weight. The ready-to-use dye composition in accordance with the invention can also contain, in addition to the dyes defined above, other oxidation 15 bases and/or other couplers and/or other dyes such as, for example, direct dyes, in particular to modify the shades or to enrich them with glints. Among the oxidation bases which can additionally be present in the ready-to-use dye 20 composition in accordance with the invention, mention may be made in particular of para-phenylenediamines, bis (phenyl) alkylenediamines, ortho-phenylenediamines, para-aminophenols and ortho-aminophenols, and the addition salts thereof with an acid. 25 When they are used, these additional oxidation bases preferably represent from 0.0005 to 12%
I
20 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. Among the couplers which can additionally be 5 present in the ready-to-use dye composition in accordance with the invention, mention may be made in particular of meta-phenylenediamines, meta-aminophenols and meta-diphenols, and the addition salts thereof with an acid. 10 When they are present, these additional couplers preferably represent from 0.0001 to 10% by weight approximately relative to the total weight of the ready-to-use dye composition and even more preferably from 0.005 to 5% by weight approximately 15 relative to this weight. In general, the addition salts with an acid which can be used in the context of the dye compositions of the invention (oxidation bases and couplers) are chosen in particular from the 20 hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates. The medium which is suitable for dyeing (or support) for the ready-to-use dye composition in accordance with the invention generally consists of 25 water or a mixture of water and at least one organic solvent to dissolve the compounds which would not be -A1 21 sufficiently soluble in water. By way of organic solvents, mention may be made, for example, of
C
1
-C
4 alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 5 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. 10 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. 15 The pH of the ready-to-use composition in accordance with the invention is chosen such that the enzymatic activity of the 2 -electron oxidoreductase is not adversely affected. It is generally between 5 and 11 approximately and preferably between 6.5 and 10 20 approximately. It can be adjusted to the desired value using acidifying or basifying agents usually used for dyeing keratin fibres. Among the acidifying agents, mention may be made, by way of example, of inorganic or organic acids 25 such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, 22 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 5 carbonates, alkanolamines such as mono-, di- and triethanolamine, 2-methyl-2-aminopropanol and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (V) below: R13 R N-W-N (V) R R 1 6 in which W is a propylene residue optionally 10 substituted with a hydroxyl group or a C 1 -C alkyl radical; R,,, R 14 , R 1 and R 16 , which may be identical or different, represent a hydrogen atom or a C 1
-C
4 alkyl or
C
1
-C
4 hydroxyalkyl radical. The ready-to-use dye composition in 15 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 20 zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, antioxidants, enzymes other than the 2-electron oxidoreductases used in accordance with 1-)6 23 the invention, such as, for example, peroxidases, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, conditioners, such as, for example, silicones, film-forming agents, preserving 5 agents and opacifiers. Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s) such that the advantageous properties intrinsically associated with the ready-to 10 use dye composition in accordance with the invention are not, or are not substantially, adversely affected by the addition or additions envisaged. The ready-to-use dye composition in accordance with the invention can be in various forms, 15 such as in the form of liquids, creams or gels, which may be pressurized, or in any other form which is suitable for dyeing keratin fibres, and in particular human hair. In this case, the oxidation dye(s) and the 2-electron oxidoreductase(s) are present in the same 20 ready-to-use composition, and consequently the said composition must be free of gaseous oxygen, so as to avoid any premature oxidation of the oxidation dye(s). A subject of the invention is also a process for dyeing keratin fibres, and in particular human 25 keratin fibres such as the hair, using the ready-to-use dye composition as defined above. _-1
C
24 According to this process, at least one ready-to-use dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, after which the 5 fibres are rinsed, optionally washed with shampoo, rinsed again and dried. The time required to develop the coloration on the keratin fibres is usually between 3 and 60 minutes and even more precisely between 5 and 10 40 minutes. According to one specific embodiment of the invention, the process includes a preliminary step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is 15 suitable for dyeing, at least one heterocyclic oxidation base as defined above and/or at least one heterocyclic coupler as defined above, and, on the other hand, a composition (B) comprising, in a medium which is suitable for dyeing, at least one enzyme of 20 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres. The compositions A and B in accordance with 25 the invention can be packaged in a multi-compartment dyeing device or multi-compartment dyeing "kit" or any 25 other multi-compartment packaging system, a first compartment of which contains composition (A) as defined above and a second compartment of which contains composition (B) as defined above. These 5 devices can be equipped with a means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2,586,913 in the name of the Applicant. The examples which follow are intended to 10 illustrate the invention without thereby limiting its scope. EXAMPLES COMPARATIVE EXAMPLES 1 AND 2 The ready-to-use dye compositions below were 15 prepared (contents in grams): COMPOSITION 1(*) 2 para-Phenylenediamine (benzenic 0.324 oxidation base) 2,4,5,6-Tetraaminopyrimidine sulphate - 0.714 20 (heterocyclic oxidation base) Resorcinol (benzenic coupler) 0.33 0.33 Uricase from Arthrobacter globiformis, at 20 International Units (I.U.)/mg, 1.5 1.5 sold by the company Sigma 25 Uric acid 1.5 1.5 Common dye support (**) (**) (**) Demineralized water qs 100 g 100 g (*) Example not forming part of the invention RA4/ -7C 26 (**): Common dye support: - Ethanol 10.0 g - Hydroxypropyl guar gum sold under the name Jaguar HP 60 by the company 5 Mayhall 0.8 g - Poly (C 8 -C) alkylglucoside as an aqueous solution containing 60% active material (A.M.) buffered with ammonium citrate (0.5%), sold under the name 10 Oramix CG110 by the company SEPPIC 8.0 g - Monoethanolamine qs pH = 9.5 It is important to note that each of the ready-to-use dye compositions described above contains the same molar amount of each of the oxidation bases, 15 i.e. 3 x 10- mol. Each of the ready-to-use dye compositions described above was applied to locks of natural grey hair containing 90% white hairs, for 30 minutes. The hair was then rinsed, washed with a standard shampoo 20 and then dried. The colour of the locks was then evaluated before and after dyeing in the Munsell system using a Minolta CM 2002 colorimeter so as to determine the intensity of the colorations obtained with each of the 25 compositions described above. The difference between the colour of the lock before dyeing and the colour of the lock after dyeing was calculated by applying the Nickerson formula: 4U '')4 27 AE = 0.4 CoAH + 6AV + 3AC as described, for example, in "Couleur, Industrie et Technique [Colour, Industry and Technology]"; pages 14-17; Vol. No. 5; 1978. 5 In this formula, AE represents the difference in colour between two locks, AH, AV and AC represent the variation in the absolute value of the parameters H, V and C, and Co represents the purity of the lock relative to which it is desired to evaluate the 10 difference in colour. The intensity of the coloration (AE) is proportionately greater the larger the figure indicated. The results are given in Table I below: 15 Table I Colour of the Colour of the Intensity of the EXAMPLE hair before hair coloration dyeing after dyeing AH AV AC AE 1(*) 3.2 Y 5.0/1.6 3.2 Y 3.6/2.2 0 1.4 0.6 10.2 2 3.2 Y 5.0/1.6 8.3 R 3.7/2.9 14.9 1.3 1.3 21.2 (*) : Example not forming part of the invention. 20 These results show that, in the presence of the uricase/uric acid oxidizing system, the ready-to use dye composition of Example 1 not forming part of the invention, since it does not contain a heterocyclic oxidation dye, gives a coloration which is markedly RA4/ 28 less intense than that of the ready-to-use dye composition of Example 2 in accordance with the invention which contains at least one heterocyclic compound, i.e. a heterocyclic oxidation base which is 5 2,4,5,6-tetraaminopyrimidine. COMPARATIVE EXAMPLES 3 AND 4 The ready-to-use dye compositions below were prepared (contents in grams): COMPOSITION 3(*) 4(*) 10 para-Phenylenediamine (benzenic 0.648 oxidation base) 2,4,5,6-Tetraaminopyrimidine sulphate - 1.428 (heterocyclic oxidation base) Resorcinol (benzenic coupler) 0.66 0.66 15 Common dye support (***) (***) (***) Demineralized water qs 100 g 100 g (*) Example not forming part of the invention (***): Common dye support: - Ethanol 20.0 g 20 - Hydroxypropyl guar gum sold under the name Jaguar HP 60 by the company Mayhall 1.6 g - Poly(C 8 -C,)alkylglucoside as an aqueous solution containing 60% active 25 material (A.M.) buffered with ammonium citrate (0.5%), sold under the name Oramix CG110 by the company SEPPIC 8.0 g - Monoethanolamine qs pH = 9.5 It is important to note that each of the 29 ready-to-use dye compositions described above contains the same molar amount of each of the oxidation bases, i.e. 6 x 10-3 mol. At the time of use, each of the ready-to-use 5 dye compositions described above was mixed with an equal amount by weight of a 20-volume hydrogen peroxide solution (6% by weight). Each of the resulting mixtures was applied to locks of natural grey hair containing 90% white hairs, 10 for 30 minutes. The locks of hair were then rinsed, washed with a standard shampoo, rinsed again and then dried. As described before for Examples 1 and 2 above, the coloration was evaluated in the Munsell 15 system, before and after dyeing, using a Minolta CM2002 colorimeter. The intensity of the coloration was calculated by applying the Nickerson formula. The results are collated in Table II below: 20 Table II Colour of the Colour of the Intensity of the EXAMPLE hair before hair coloration dyeing after dyeing AH AV AC AE 3(*) 2.9 Y 5.9/1.5 9.3 YR 3.6 3.4 0.3 23.5 2.5/1.2 4(*) 2.9 Y 5.9/1.5 2.5 YR 10.4 1.5 1.5 19.7 4.4/3.0 (*): Example not forming part of the invention. 25 In contrast with what was demonstrated before for the Comparative Examples 1 and 2, these results show that by using a conventional oxidizing system not RA4 1 30 forming part of the invention, such as, for example, hydrogen peroxide in this case, the replacement of a benzenic dye with a heterocyclic dye (in this case para-phenylenediamine was replaced with 5 2,4,5,6-tetraaminopyrimidine) does not make it possible to increase the intensity of the colorations obtained. COMPARATIVE EXAMPLES 5 AND 6 The ready-to-use dye compositions below were prepared (contents in grams): 10 COMPOSITION 5(*) 6 2,5-Diaminopyridine dihydrochloride 0.546 (oxidation base outside the invention) 2,4,5,6-Tetraaminopyrimidine sulphate - 0.714 (heterocyclic oxidation base) 15 Resorcinol (benzenic coupler) 0.33 0.33 Uricase from Arthrobacter globiformis, at 20 (I.U.)/mg, sold by the company 1.0 1.0 Sigma Uric acid 1.0 1.0 20 Common dye support (**) (**) (**) Demineralized water qs 100 g 100 g (*) Example not forming part of the invention (**) Common dye support: This is identical to the one used for 25 Examples 1 and 2 above. It is important to note that each of the ready-to-use dye compositions described above contains the same molar amount of each of the oxidation bases,
RA,
31 i.e. 3 x 10- mol. Each of the ready-to-use dye compositions described above was applied to locks of natural grey hair containing 90% white hairs, for 30 minutes. The 5 hair was then rinsed, washed with a standard shampoo and then dried. As described before for Examples 1 and 2 above, the coloration was evaluated in the Munsell system, before and after dyeing, using a Minolta 10 CM 2002 colorimeter. The intensity of the coloration was calculated by applying the Nickerson formula. The results are collated in Table III below: Table III Colour of the Colour of the Intensity of the 15 EXAMPLE hair before hair coloration dyeing after dyeing AH AV AC AE 5(*) 2.9 Y 5.9/1.5 4.8 YR 8.1 1.1 0.6 13.3 4.8/2.1 6 2.9 Y 5.9/1.5 10.0 R 12.9 1.2 1.1 18.2 4.7/2.6 (*): Example not forming part of the invention. These results show that, in the presence of 20 the uricase/uric acid oxidizing system, the ready-to use dye composition of Example 5 not forming part of the invention, since it contains 2,5-diaminopyridine which is a monocyclic pyridine oxidation base outside the invention, gives a coloration which is markedly 25 less intense than that of the ready-to-use dye composition of Example 6 in accordance with the -7> 32 invention which contains at least one heterocyclic compound in accordance with the invention, i.e. a heterocyclic oxidation base which is 2,4,5,6-tetraaminopyrimidine. 5 EXAMPLES 7 TO 13 OF DYEING The ready-to-use dye compositions below in accordance with the invention were prepared (contents in grams): 1 33 0)0 on 01 coH Nq 01 00 o00 040 o 0 H v-i 0 a) a o; 0 0- 0 0D H 0 o1 coH H H 0 o 0 o C; 0 I~~C I IIH o 0 Ho V 04 r4 N 4 0 -44 0 C) V ro >1 0 H= M H - W 0 0n I) ICd >1 r. V. V 11 0 0 0~ m -- I 02Cm -H E ~ H >, V 4-J N1 m 1 0q 4I04 - 0 rA -I >-a)C: 1 - 10 0n 1 H) Nr 04 0-i V 04 C d HJ (H 0 4j -H- (U 0 0 d (U rd C v rI H) rz 0 4Q -H V H .-il ( 0 .- i -H >4 ' I4Ln r= > H 4 > 4 H 4 -) 0) -4 0i- Vd 4 04 0 I J N (L 0- - 4 -H >11 - H. V ( 0 m 41 H - >- 1 0 0 >1 0- Cd 0 0 : X 4 NV 04 M- 0 , U-i (dr H > -H .1-I 0o V1 0c V >d4- H H. 4-' 00C 1-V 'd-I Z~ VV -, E v - >, V Cd 0 ,O4~ 0 4 rq Cd') >410 V) '' 4 I '-I 1, 0) 4 E 0 -0 caN H- 0 0 1 H4 " P4 >iQ 0- 0 HH ZC > i =H L I I >4 4 0 CH 4 , rC -H4 00 I>- VD EU H X VO L) *-.-H ro Cd PQ HO 0- .4 d0 > 0 >1 0 '0 0'(0 V 1 0 N0~ -H A-. -H0. 4J 4-I 4 ~ -) 0 z ~ C M>4 4 C '>1 VU >-. V (1) Cd '>4 U -H 40 4 4 U 4 x x wH r -I -i Ca H - H r- E E >V -- H I I I I -0 V I-H 0 - 0 V 0.'4 r-f 0.CV N -D H CN- .0 A' Cr'I U Lii 34 (**): Common dye support: This is identical to the one used for Examples 1 and 2 above. Each of the ready-to-use dye compositions 5 described above was applied to locks of natural or permanent-waved grey hair containing 90% white hairs, for 30 minutes. The hair was then rinsed, washed with a standard shampoo and then dried. The locks of hair were dyed in the shades 10 given in Table IV below. Table IV EXAMPLE Shade obtained on Shade obtained on natural hair permanent-waved hair 7 Golden iridescent Golden iridescent 8 Iridescent Iridescent 15 9 Coppery iridescent Coppery iridescent 10 Golden ash Matt ash 11 Intense iridescent Intense iridescent 12 Dark purple Dark purple 13 Violet Violet
Claims (37)
1. Ready-to-use composition for the oxidation dyeing of keratin fibres, and in particular human keratin fibres such as the hair, comprising the 5 combination of at least one oxidation base and at least one coupler, characterized in that it comprises, in a medium which is suitable for dyeing, at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, and 10 in that the said oxidation base and/or the said coupler is chosen from heterocyclic compounds with the exclusion of monocyclic pyridine compounds.
2. Composition according to Claim 1, characterized in that the 2-electron oxidoreductase is 15 chosen from uricases of animal, microbiological or biotechnological origin.
3. Composition according to Claim 1 or 2, characterized in that the 2-electron oxidoreductase(s) represent(s) from 0.01 to 20% by weight relative to the 20 total weight of the ready-to-use dye composition.
4. Composition according to Claim 3, characterized in that the 2-electron oxidoreductase(s) represent(s) from 0.1 to 5% by weight relative to the total weight of the ready-to-use dye composition. 25
5. Composition according to Claim 2, characterized in that the donor (or substrate) for the 36 said 2-[lacuna] oxidoreductase is chosen from uric acid and its salts.
6. Composition according to any one of the preceding claims, characterized in that the donor(s) 5 represent(s) from 0.01 to 20% by weight relative to the total weight of the ready-to-use dye composition.
7. Composition according to Claim 6, characterized in that the donor(s) represent(s) from 0.1 to 5% by weight relative to the total weight of the 10 ready-to-use dye composition.
8. Composition according to any one of the preceding claims, characterized in that the heterocyclic oxidation base(s) is (are) chosen from pyrimidine derivatives and pyrazole derivatives, and 15 the addition salts thereof with an acid.
9. Composition according to Claim 8, characterized in that the pyrimidine derivatives are chosen from 2,4,5,6-tetraaminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine and pyrazolopyrimidine 20 derivatives, and the addition salts thereof with an acid.
10. Composition according to Claim 9, characterized in that the pyrazolopyrimidine derivatives are chosen from pyrazolo[1,5-a]pyrimidine 25 3,7-diamine, 2-methylpyrazolo[1,5-a]pyrimidine 3,7-diamine, 2,5-dimethylpyrazolo[1,5-a]pyrimidine SRA4 1 41 37 3,7-diamine, pyrazolo[1,5-a]pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine, 3-aminopyrazolo[1,5-a]pyrimidin-7-ol, 3-amino 5-methylpyrazolo[1,5-a]pyrimidin-7-ol, 5 3-aminopyrazolo[1,5-a]pyrimidin-5-ol, 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 3-amino-7-S-hydroxyethylamino-5-methylpyrazolo[1,5-a] pyrimidine, 2-(7-aminopyrazolo[1,5-a]pyrimidin 3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin 10 7-yl) (2-hydroxyethyl)aminoethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin 3-yl) (2-hydroxyethyl)aminoethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and 15 2,5-N-7,N-7-tetramethylpyrazolo[1,5-a]pyrimidine 3,7-diamine, and the addition salts thereof and the tautomers thereof, when a tautomeric equilibrium exists.
11. Composition according to Claim 8, 20 characterized in that the pyrazole derivatives are chosen from 4,5-diaminopyrazole, 4,5-diamino 1-methylpyrazole, 1-benzyl-4,5-diaminopyrazole, 3,4-diaminopyrazole, 1-benzyl-4,5-diamino 3-methylpyrazole, 4-amino-1,3-dimethyl 25 5-hydrazinopyrazole, 4,5-diamino-3-methyl 1-phenylpyrazole, 4,5-diamino-3-methyl-1-tert 4Lw) 38 butylpyrazole, 4,5-diamino-1-methyl-3-tert butylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4'-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 5 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole and 4,5-diamino-3-methyl-l-isopropylpyrazole, and the addition salts thereof with an acid.
12. Composition according to any one of the 10 preceding claims, characterized in that the heterocyclic oxidation base(s) represent(s) from 0.0005 to 12% by weight relative to the total weight of the ready-to-use dye composition.
13. Composition according to Claim 12, 15 characterized in that the heterocyclic oxidation base(s) represent(s) from 0.005 to 6% by weight relative to the total weight of the ready-to-use dye composition.
14. Composition according to any one of the 20 preceding claims, characterized in that the heterocyclic coupler(s) is (are) chosen from indole derivatives, indoline derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyrazoloazole derivatives, pyrroloazole 25 derivatives, imidazoloazole derivatives, pyrazolopyrimidine derivatives, pyrazoline-3,5-dione 39 derivatives, pyrrolo[3,2-d]oxazole derivatives, pyrazolo[3,4-d]thiazole derivatives, thiazoloazole S-oxide derivatives and thiazoloazole S,S-dioxide derivatives, and the addition salts thereof with an 5 acid.
15. Composition according to Claim 14, characterized in that the indole derivatives are chosen from the compounds of formula (I) below, and the addition salts thereof with an acid: x R, 10 in which: R 1 represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 2 -C 4 mono- or polyhydroxyalkyl radical or a C 1 -C 4 aminoalkyl radical in which the amine is mono- or disubstituted with a C 1 -C 4 alkyl group; 15 R 2 represents a hydrogen atom or a C 1 -C 4 alkyl radical; R 3 represents a hydrogen atom or a Cl-C 4 alkyl or hydroxyl radical; X represents a hydroxyl radical or a radical NHR 4 in which R 4 represents a hydrogen atom or a CI-C 4 alkyl or 20 C 1 -C 4 hydroxyalkyl radical.
16. Composition according to Claim 15, characterized in that the indole derivatives are chosen RA4X 71 40 from 4-hydroxyindole, 6-hydroxyindole, 7-aminoindole, 6-aminoindole, 7-hydroxyindole, 7-ethyl-6- (B-hydroxy ethyl) aminoindole, 4-aminoindole, 6-hydroxy 1-methylindole, 5, 6-dihydroxyindole, 4-hydroxy 5 1-N-methylindole, 4-hydroxy-2-methylindole, 4-hydroxy 5-methylindole, 4-hydroxy-l-N- (B-hydroxyethyl) indole, 4-hydroxy-1-N- (fB-hydroxypropyl) indole, 1-N- (IB,y-dihydroxypropyl) -4-hydroxyindole, 4-hydroxy 1-N- (B-hydroxyethyl) -5-methylindole and 10 1-N- (y-dimethylaminopropyl) -4-hydroxyindole, and the addition salts thereof with an acid.
17. Composition according to Claim 14, characterized in that the indoline derivatives are chosen from 4-hydroxyindoline, 6-hydroxyindoline, 15 6-aminoindoline and 5,6-dihydroxyindoline, and the addition salts thereof with an acid.
18. Composition according to Claim 14, characterized in that the benzimidazole derivatives are chosen from the compounds of formula (II) below, and 20 the addition salts thereof with an acid: R 7 R N R6 R in which: R. represents a hydrogen atom or a C 1 -C 4 alkyl radical, 441/ 41 R 6 represents a hydrogen atom or a C 1 -C 4 alkyl or phenyl radical, R, represents a hydroxyl, amino or methoxy radical, R. represents a hydrogen atom or a hydroxyl, methoxy or 5 Cl-C 4 alkyl radical; with the proviso that: - when R7 denotes an amino radical, then it occupies position 4, - when R, occupies position 4, then R. occupies 10 position 7, - when R, occupies position 5, then R. occupies position 6.
19. Composition according to Claim 18, characterized in that the benzimidazole derivatives are 15 chosen from 4-hydroxybenzimidazole, 4-aminobenzimid azole, 4-hydroxy-7-methylbenzimidazole, 4-hydroxy 2-methylbenzimidazole, 1-butyl-4-hydroxybenzimidazole, 4-amino-2-methylbenzimidazole, 5,6-dihydroxybenzimid azole, 5-hydroxy-6-methoxybenzimidazole, 20 4,7-dihydroxybenzimidazole, 4,7-dihydroxy 1-methylbenzimidazole, 4,7-dimethoxybenzimidazole, 5,6-dihydroxy-1-methylbenzimidazole, 5,6-dihydroxy 2-methylbenzimidazole and 5,6-dimethoxybenzimidazole, and the addition salts thereof with an acid. 25
20. Composition according to Claim 14, characterized in that the benzomorpholine derivatives 42 are chosen from the compounds of formula (III) below, and the addition salts thereof with an acid: 0 Z x 10 R9 in which: R 9 and Ri 0 , which may be identical or different, 5 represent a hydrogen atom or a C 1 -C 4 alkyl radical, Z represents a hydroxyl or amino radical.
21. Composition according to Claim 20, characterized in that the benzomorpholine derivatives are chosen from 6-hydroxy-1, 4-benzomorpholine, 10 N-methyl-6-hydroxy-1,4-benzomorpholine and 6-amino 1,4-benzomorpholine, and the addition salts thereof with an acid.
22. Composition according to Claim 14, characterized in that the sesamol derivatives are 15 chosen from the compounds of formula (IV) below, and the addition salts thereof with an acid: R R1 2 (IV) 0 in which: R 11 denotes a hydroxyl, amino, (C 1 -C 4 )alkylamino, 43 monohydroxy (C 1 -C 4 ) alkylamino or polyhydroxy (C 2 -C 4 ) alkylamino radical, R 12 denotes a hydrogen or halogen atom or a C 1 -C 4 alkoxy radical. 5
23. Composition according to Claim 22, characterized in that the sesamol derivatives are chosen from 2-bromo-4,5-methylenedioxyphenol, 2-methoxy-4,5-methylenedioxyaniline and 2- (U-hydroxyethyl) amino-4, 5-methylenedioxybenzene, and 10 the addition salts thereof with an acid.
24. Composition according to Claim 14, characterized in that the pyrazoloazole derivatives are chosen from: - 2-methylpyrazolo[1,5-b]-1,2,4-triazole, 15 - 2-ethylpyrazolo[1,5-b]-1,2,4-triazole, - 2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, - 2-phenylpyrazolo[1,5-b]-1,2,4-triazole, - 2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole, - 7-chloro-2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole, 20 - 3 ,6-dimethylpyrazolo[3,2-c]-1,2,4-triazole, - 6-phenyl-3-methylthiopyrazolo[3,2-c]-1,2,4-triazole and - 6-aminopyrazolo[1,5-a]benzimidazole, and the addition salts thereof with an acid. 25
25. Composition according to Claim 14, characterized in that the pyrroloazole derivatives are 44/ 44 chosen from: - 5-cyano-4-ethoxycarbonyl-8-methylpyrrolo[1,2-b] 1,2,4-triazole, - 5-cyano-8-methyl-4-phenylpyrrolo[1,2-b] 5 1,2,4-triazole, - 7 -amido-6-ethoxycarbonylpyrrolo[1,2-a]-benzimidazole, and the addition salts thereof with an acid.
26. Composition according to Claim 14, characterized in that the imidazoloazole derivatives 10 are chosen from: - 7,8-dicyanoimidazolo[3,2-a]imidazole, - 7 , 8 -dicyano-4-methylimidazolo[3,2-alimidazole, and the addition salts thereof with an acid.
27. Composition according to Claim 14, 15 characterized in that the pyrazolopyrimidine derivatives are chosen from: - pyrazolo[1,5-a]pyrimidin-7-one, - 2 ,5-dimethylpyrazolo[1,5-a]pyrimidin-7-one, - 2 -methyl-6-ethoxycarbonylpyrazolo[1,5-a]pyrimidin 20 7-one, - 2-methyl-5-methoxymethylpyrazolo[1,5-a]pyrimidin 7-one, - 2 -tert-butyl-5-trifluoromethylpyrazolo[1,5-a] pyrimidin-7-one, 25 - 2 , 7 -dimethylpyrazolo[1,5-a]pyrimidin-5-one, and the addition salts thereof with an acid. RRA 45
28. Composition according to Claim 14, characterized in that the pyrazoline-3,5-dione derivatives are chosen from: - 1, 2 -diphenylpyrazoline-3 ,5-dione, 5 - 1, 2 -diethylpyrazoline-3,5-dione, and the addition salts thereof with an acid.
29. Composition according to any one of the preceding claims, characterized in that the heterocyclic coupler(s) represent(s) from 0.0001 to 10% 10 by weight relative to the total weight of the ready-to use dye composition.
30. Composition according to Claim 29, characterized in that the heterocyclic coupler(s) represent(s) from 0.005 to 5% by weight relative to the 15 total weight of the ready-to-use dye composition.
31. Composition according to any one of the preceding claims, characterized in that it contains at least one additional oxidation base chosen from para phenylenediamines, bis (phenyl) alkylenediamines, ortho 20 phenylenediamines, para-aminophenols and ortho aminophenols, and the addition salts thereof with an acid and/or at least one additional coupler chosen from meta-phenylenediamines, meta-aminophenols and meta diphenols, and the addition salts thereof with an acid. 25
32. Composition according to any one of the preceding claims, characterized in that the addition RI4 441 46 salts with an acid are chosen from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
33. Composition according to any one of the 5 preceding claims, characterized in that the medium which is suitable for dyeing consists of water or a mixture of water and at least one organic solvent.
34. Composition according to any one of the preceding claims, characterized in that it has a pH of 10 between 5 and 11.
35. Composition according to any one of the preceding claims, characterized in that it contains at least one peroxidase.
36. Process for dyeing keratin fibres, and 15 in particular human keratin fibres such as the hair, characterized in that at least one ready-to-use dye composition as defined in any one of the preceding claims is applied to the said fibres, for a period which is sufficient to develop the desired coloration. 20
37. Process according to Claim 36, characterized in that it includes a preliminary step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is suitable for dyeing, at least one heterocyclic 25 oxidation base as defined in any one of Claims 1, 8 to 13 and 32 and/or at least one heterocyclic coupler as 47 defined in any one of Claims 1, 14 to 30 and 32, and, on the other hand, a composition (B) comprising, in a medium which is suitable for dyeing, at least one enzyme of 2-electron oxidoreductase type in the 5 presence of at least one donor for the said enzyme, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9706802 | 1997-06-03 | ||
FR9706802A FR2763841B1 (en) | 1997-06-03 | 1997-06-03 | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
PCT/FR1998/000913 WO1998055083A1 (en) | 1997-06-03 | 1998-05-06 | Keratin fibre oxidation dyeing composition and dyeing method using same |
Publications (2)
Publication Number | Publication Date |
---|---|
AU7660498A true AU7660498A (en) | 1998-12-21 |
AU730767B2 AU730767B2 (en) | 2001-03-15 |
Family
ID=9507525
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU76604/98A Ceased AU730767B2 (en) | 1997-06-03 | 1998-05-06 | Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP0988021B1 (en) |
JP (1) | JP3882130B2 (en) |
KR (1) | KR100411643B1 (en) |
CN (1) | CN1198572C (en) |
AT (1) | ATE253887T1 (en) |
AU (1) | AU730767B2 (en) |
BR (1) | BR9809532A (en) |
CA (1) | CA2290681A1 (en) |
DE (1) | DE69819722T2 (en) |
ES (1) | ES2212299T3 (en) |
FR (1) | FR2763841B1 (en) |
HU (1) | HUP0002411A3 (en) |
PL (1) | PL337155A1 (en) |
RU (1) | RU2187297C2 (en) |
WO (1) | WO1998055083A1 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2779952B1 (en) | 1998-06-19 | 2000-08-04 | Oreal | TINCTORIAL COMPOSITION CONTAINING PYRAZOLO- [1,5-A] - PYRIMIDINE AS OXIDATION BASE AND PYRIDINIC COUPLER, AND DYEING METHODS |
FR2779949B1 (en) * | 1998-06-19 | 2004-05-21 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
FR2791562B1 (en) * | 1999-03-29 | 2004-03-05 | Oreal | TINCTORIAL COMPOSITION CONTAINING PYRAZOLO- [1,5-A] - PYRIMIDINE AND A MONOCYCLIC POLYAMINOPYRIMIDINE AS OXIDATION BASES AND A COUPLER, AND DYEING METHODS |
FR2794972B1 (en) * | 1999-06-21 | 2001-08-10 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
CN1202804C (en) | 1999-12-24 | 2005-05-25 | 汉高狮王化妆品有限公司 | One-pack type post-foamable oxidation hair-dye composition |
FR2806908B1 (en) | 2000-03-30 | 2002-12-20 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
FR2830193B1 (en) * | 2001-09-28 | 2004-10-15 | Oreal | TINCTORIAL COMPOSITION COMPRISING AN OXIDATION BASE OF THE DIAMINOPYRAZOLE TYPE AND AN OXIDIZING AGENT OF AN ENZYMATIC NATURE |
DE102005039456A1 (en) * | 2005-08-18 | 2007-02-22 | Henkel Kgaa | Agent for dyeing keratinous fibers |
CN103077741B (en) * | 2012-12-31 | 2015-12-09 | 东南大学 | The storage unit circuit of a kind of SRAM of low voltage operating |
FR3007282B1 (en) * | 2013-06-21 | 2015-07-24 | Oreal | OXIDATION COLORING PROCESS USING A COMPOSITION COMPRISING A MONO AMINO-BENZENE AND A METAL CATALYST |
WO2023272610A1 (en) * | 2021-06-30 | 2023-01-05 | L'oreal | Dye kit |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0745385B2 (en) * | 1987-03-31 | 1995-05-17 | 協和醗酵工業株式会社 | Cosmetic composition for hair |
FR2692782B1 (en) * | 1992-06-25 | 1995-06-23 | Oreal | PROCESS FOR DYEING KERATINIC FIBERS WITH INDOLIC OR INDOLINIC DERIVATIVES, HYDROGEN PEROXIDE AND PEROXYDASE. |
CA2150596A1 (en) * | 1994-12-16 | 1996-06-17 | Yoshio Tsujino | Oxidation hair dye composition |
EP0865465B1 (en) * | 1995-11-30 | 2001-05-30 | Novozymes A/S | Laccases with improved dyeing properties |
-
1997
- 1997-06-03 FR FR9706802A patent/FR2763841B1/en not_active Expired - Fee Related
-
1998
- 1998-05-06 KR KR10-1999-7011166A patent/KR100411643B1/en not_active IP Right Cessation
- 1998-05-06 BR BR9809532-3A patent/BR9809532A/en not_active Application Discontinuation
- 1998-05-06 DE DE69819722T patent/DE69819722T2/en not_active Expired - Fee Related
- 1998-05-06 ES ES98924391T patent/ES2212299T3/en not_active Expired - Lifetime
- 1998-05-06 AU AU76604/98A patent/AU730767B2/en not_active Ceased
- 1998-05-06 AT AT98924391T patent/ATE253887T1/en not_active IP Right Cessation
- 1998-05-06 JP JP50169399A patent/JP3882130B2/en not_active Expired - Fee Related
- 1998-05-06 PL PL98337155A patent/PL337155A1/en unknown
- 1998-05-06 EP EP98924391A patent/EP0988021B1/en not_active Expired - Lifetime
- 1998-05-06 HU HU0002411A patent/HUP0002411A3/en unknown
- 1998-05-06 CA CA002290681A patent/CA2290681A1/en not_active Abandoned
- 1998-05-06 CN CNB988057255A patent/CN1198572C/en not_active Expired - Fee Related
- 1998-05-06 RU RU2000100367/14A patent/RU2187297C2/en not_active IP Right Cessation
- 1998-05-06 WO PCT/FR1998/000913 patent/WO1998055083A1/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
DE69819722T2 (en) | 2004-09-30 |
HUP0002411A3 (en) | 2003-01-28 |
HUP0002411A2 (en) | 2000-12-28 |
EP0988021B1 (en) | 2003-11-12 |
ES2212299T3 (en) | 2004-07-16 |
CA2290681A1 (en) | 1998-12-10 |
FR2763841B1 (en) | 2000-02-11 |
KR20010013181A (en) | 2001-02-26 |
BR9809532A (en) | 2000-07-25 |
EP0988021A1 (en) | 2000-03-29 |
FR2763841A1 (en) | 1998-12-04 |
ATE253887T1 (en) | 2003-11-15 |
CN1198572C (en) | 2005-04-27 |
DE69819722D1 (en) | 2003-12-18 |
AU730767B2 (en) | 2001-03-15 |
PL337155A1 (en) | 2000-07-31 |
WO1998055083A1 (en) | 1998-12-10 |
JP2000513748A (en) | 2000-10-17 |
CN1259039A (en) | 2000-07-05 |
JP3882130B2 (en) | 2007-02-14 |
KR100411643B1 (en) | 2003-12-18 |
RU2187297C2 (en) | 2002-08-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU730579B2 (en) | Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition | |
EP0994692B1 (en) | Oxidation dyeing composition for keratinous fibres containing a 3-aminopyridine azo derivative and dyeing method using said composition | |
ES2287663T3 (en) | COMPOSITION FOR THE STAINING OF KERATIN FIBERS AND PROCESSING OF DYING THAT USES THIS COMPOSITION. | |
ES2207859T3 (en) | COMPOSITION OF DYEING BY OXIDATION OF KERATIN FIBERS. | |
ES2218854T3 (en) | DYE COMPOSITION OF THE QUERATINIC FIBERS AND DYEING PROCEDURE USING THIS COMPOSITION. | |
RU99124578A (en) | COMPOSITION FOR OXIDATIVE COLORING KERATIN FIBERS AND COLORING METHOD USING THIS COMPOSITION | |
FR2791563A1 (en) | KERATIN FIBER OXIDATION DYEING COMPOSITION AND DYEING METHOD USING THE SAME | |
AU730767B2 (en) | Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition | |
EP1352636B1 (en) | Oxidation dyeing composition for keratin fibers comprising 2-chloro-6-methyl-3-aminophenol and an oxidation base, and dyeing method | |
KR100364310B1 (en) | DYEING COMPOSITION CONTAINING A PYRAZOLO-[1,5-a]-PYRIMIDINE AS OXIDATION BASE AND A PYRIDINE COUPLING AGENT, AND DYEING METHOD | |
FR2831055A1 (en) | Oxidation dye composition, useful for dyeing keratinic fibers, comprises 1-(2-hydroxyethyl)-4-hydroxyindole as a coupler and a heterocyclic developer | |
RU2000100367A (en) | COMPOSITION FOR OXIDATIVE PAINTING OF KERATIN FIBERS AND COLOR METHOD IN WHICH USE THIS COMPOSITION | |
US6890362B2 (en) | Oxidation dyeing composition for keratinous fibers and dyeing method using same | |
FR2845281A1 (en) | TINCTORIAL COMPOSITION COMPRISING AT LEAST ONE PYRAZOLOPYRIMIDINE OXIDATION BASE AND AT LEAST ONE 6-ALCOXY 2,3-DIAMINOPYRIDIMINE COUPLER | |
FR2773481A1 (en) | Composition for oxidation dyeing of keratinic fibers, especially human hair | |
CZ426799A3 (en) | Preparation for oxidative dyeing keratin fibers and dyeing process employing such preparation | |
MXPA99010758A (en) | Keratin fibre oxidation dyeing composition and dyeing method using same | |
EP1093793A2 (en) | Composition for oxidative dyeing of keratinous fibres and dyeing process using same | |
EP1093788A1 (en) | Oxydative dyeing composition for keratinic fibres and dyeing process using this composition | |
FR2845282A1 (en) | Composition useful for dyeing keratinic fibers, e.g. hair, comprises a 2,3-diaminopyridine coupler and a non-fused pyrazole developer | |
MXPA99005838A (en) | Oxidation dyeing for keratin fibres |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FGA | Letters patent sealed or granted (standard patent) |