LU87337A1 - TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS AND DYEING METHODS USING THE SAME - Google Patents
TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS AND DYEING METHODS USING THE SAME Download PDFInfo
- Publication number
- LU87337A1 LU87337A1 LU87337A LU87337A LU87337A1 LU 87337 A1 LU87337 A1 LU 87337A1 LU 87337 A LU87337 A LU 87337A LU 87337 A LU87337 A LU 87337A LU 87337 A1 LU87337 A1 LU 87337A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- amino
- methyl
- aniline
- phenol
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 75
- 239000002243 precursor Substances 0.000 title claims description 22
- 238000007254 oxidation reaction Methods 0.000 title claims description 21
- 239000000835 fiber Substances 0.000 title claims description 19
- 230000003647 oxidation Effects 0.000 title claims description 17
- 238000004043 dyeing Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 46
- 239000000975 dye Substances 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- -1 C1-C4 alkyl radical Chemical class 0.000 claims description 22
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 102000011782 Keratins Human genes 0.000 claims description 14
- 108010076876 Keratins Proteins 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 7
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- SXJQUUPSLJTKKT-UHFFFAOYSA-N 4-hydroxy-2-methoxyaniline Natural products COC1=CC(O)=CC=C1N SXJQUUPSLJTKKT-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- OSNDKMMOJAUTDW-UHFFFAOYSA-N 1,2-dimethylindol-6-ol Chemical compound C1=C(O)C=C2N(C)C(C)=CC2=C1 OSNDKMMOJAUTDW-UHFFFAOYSA-N 0.000 claims description 2
- OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 claims description 2
- OWVWIOHXPDECMB-UHFFFAOYSA-N 2,3-dimethyl-1h-indol-6-ol Chemical compound OC1=CC=C2C(C)=C(C)NC2=C1 OWVWIOHXPDECMB-UHFFFAOYSA-N 0.000 claims description 2
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 claims description 2
- 229940113489 2,4-diaminophenoxyethanol Drugs 0.000 claims description 2
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims description 2
- JKIGVFLHAJUPCP-UHFFFAOYSA-N 2-methyl-1h-indol-6-ol Chemical compound C1=C(O)C=C2NC(C)=CC2=C1 JKIGVFLHAJUPCP-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
- XRMTWJAJYBZYLZ-UHFFFAOYSA-N 4-(1-hydroxyethoxy)benzene-1,3-diol Chemical compound CC(O)OC1=CC=C(O)C=C1O XRMTWJAJYBZYLZ-UHFFFAOYSA-N 0.000 claims description 2
- BNRMHEDSMWOIMC-UHFFFAOYSA-N 4-(2-aminoethoxy)benzene-1,3-diamine Chemical compound NCCOC1=CC=C(N)C=C1N BNRMHEDSMWOIMC-UHFFFAOYSA-N 0.000 claims description 2
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 2
- YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 claims description 2
- IHWPTLPROWODBQ-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine Chemical compound CONC1=CC=C(N)C=C1 IHWPTLPROWODBQ-UHFFFAOYSA-N 0.000 claims description 2
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 2
- HJUFFOMJRAXIRF-UHFFFAOYSA-N 6-hydroxy-1h-indole-2-carboxylic acid Chemical compound C1=C(O)C=C2NC(C(=O)O)=CC2=C1 HJUFFOMJRAXIRF-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000000982 direct dye Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003380 propellant Substances 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- OSVNQUBJWRJOER-UHFFFAOYSA-N 2-(9-methyldecyl)-5-(4-methylpentyl)benzene-1,3-diol Chemical compound CC(C)CCCCCCCCC1=C(O)C=C(CCCC(C)C)C=C1O OSVNQUBJWRJOER-UHFFFAOYSA-N 0.000 claims 2
- PSTUGXWVTKXNGK-UHFFFAOYSA-N 2-anilino-n-ethylacetamide Chemical compound CCNC(=O)CNC1=CC=CC=C1 PSTUGXWVTKXNGK-UHFFFAOYSA-N 0.000 claims 2
- PTXVSDKCUJCCLC-UHFFFAOYSA-N 1-hydroxyindole Chemical compound C1=CC=C2N(O)C=CC2=C1 PTXVSDKCUJCCLC-UHFFFAOYSA-N 0.000 claims 1
- OOOVRUXKQGYTPJ-UHFFFAOYSA-N 1-methylindol-6-ol Chemical compound C1=C(O)C=C2N(C)C=CC2=C1 OOOVRUXKQGYTPJ-UHFFFAOYSA-N 0.000 claims 1
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims 1
- AXSWRCGZBWBXQD-UHFFFAOYSA-N 3-methyl-1h-indol-6-ol Chemical compound OC1=CC=C2C(C)=CNC2=C1 AXSWRCGZBWBXQD-UHFFFAOYSA-N 0.000 claims 1
- JSWVCUXQICMATE-UHFFFAOYSA-N 4-amino-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C=C1N JSWVCUXQICMATE-UHFFFAOYSA-N 0.000 claims 1
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 claims 1
- NYORHELBFKLYBG-UHFFFAOYSA-N 6-hydroxy-1h-indole-3-carboxylic acid Chemical compound OC1=CC=C2C(C(=O)O)=CNC2=C1 NYORHELBFKLYBG-UHFFFAOYSA-N 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- KIUVPPYVSMQUKM-UHFFFAOYSA-N dimethyl 6-hydroxy-1-methylindole-2,3-dicarboxylate Chemical compound C1=C(O)C=C2N(C)C(C(=O)OC)=C(C(=O)OC)C2=C1 KIUVPPYVSMQUKM-UHFFFAOYSA-N 0.000 claims 1
- FVMVBNSCNRLYIJ-UHFFFAOYSA-N ethyl 6-hydroxy-1h-indole-2-carboxylate Chemical compound C1=C(O)C=C2NC(C(=O)OCC)=CC2=C1 FVMVBNSCNRLYIJ-UHFFFAOYSA-N 0.000 claims 1
- IYOILHQLYJPODQ-UHFFFAOYSA-N ethyl 6-hydroxy-1h-indole-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OCC)=CNC2=C1 IYOILHQLYJPODQ-UHFFFAOYSA-N 0.000 claims 1
- QOGGELYMQKNPGX-UHFFFAOYSA-N methyl 1-hydroxyindole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CN(C2=C1)O QOGGELYMQKNPGX-UHFFFAOYSA-N 0.000 claims 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- 229960005323 phenoxyethanol Drugs 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 6
- 229960003742 phenol Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- GPJJASIJVRXZFI-UHFFFAOYSA-N 4-methoxybenzene-1,3-diol Chemical compound COC1=CC=C(O)C=C1O GPJJASIJVRXZFI-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical class CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- BVWOHFHLLLPJLH-UHFFFAOYSA-N 2-methoxy-3,5-dimethylbenzene-1,4-diamine Chemical compound COC1=C(C)C(N)=C(C)C=C1N BVWOHFHLLLPJLH-UHFFFAOYSA-N 0.000 description 1
- KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 description 1
- XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 description 1
- MCNBYOWWTITHIG-UHFFFAOYSA-N 4-amino-2-methoxyphenol Chemical compound COC1=CC(N)=CC=C1O MCNBYOWWTITHIG-UHFFFAOYSA-N 0.000 description 1
- PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000084 Gum arabic Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Chemical class 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical class CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000006083 mineral thickener Substances 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Chemical class [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-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
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Compositions tinctoriales pour fibres kératiniques contenant des précurseurs de colorants par oxydation et des coupleurs indoliques, et procédés de teinture mettant en oeuvre ces compositions.Dye compositions for keratin fibers containing oxidative dye precursors and indole couplers, and dyeing methods using these compositions.
La présente invention est relative à de nouvelles compositions tinctoriales pour fibres kératiniques et en particulier pour cheveux humains, contenant des précurseurs de colorants d'oxydation et des coupleurs indoliques, et un procédé de teinture mettant en oeuvre de telles compositions.The present invention relates to new dye compositions for keratin fibers and in particular for human hair, containing oxidation dye precursors and indole couplers, and a dyeing process using such compositions.
Il est connu de teindre les fibres kératiniques et en particulier les cheveux humains, avec des compositions tinctoriales contenant des précurseurs de colorants d'oxydation et en particulier des p-phénylènediamines, des ortho- ou para-aminophénols appelés généralement "base d'oxydation".It is known to dye keratin fibers and in particular human hair, with dye compositions containing precursors of oxidation dyes and in particular p-phenylenediamines, ortho- or para-aminophenols generally called "oxidation base" .
On sait également qu'on peut faire varier les nuances obtenues avec ces bases d'oxydation en utilisant, en association avec ces bases, des coupleurs encore appelés modificateurs de coloration et plus particulièrement des métadiamines aromatiques, des méta-aminophénols et des métadi£)hénols.We also know that we can vary the nuances obtained with these oxidation bases by using, in combination with these bases, couplers also called color modifiers and more particularly aromatic metadiamines, meta-aminophenols and metadi () hénols.
On recherche, dans le domaine de la teinture capillaire, des précurseurs de colorants d'oxydation ou des coupleurs permettant de conférer aux cheveux, en milieu alcalin oxydant généralement utilisé en teinture d'oxydation, une coloration ayant une résistance satisfaisante à la lumière, aux lavages, aux intempéries et à la transpiration.In the field of hair dyeing, oxidation dye precursors or couplers making it possible to impart to the hair, in an oxidizing alkaline medium generally used in oxidation dyeing, a coloring having a satisfactory resistance to light, to washes, weathering and perspiration.
La demanderesse vient de découvrir, ce qui fait l'objet de l'invention, que l'utilisation de certains dérivés indoliques à titre de coupleurs, avec des précurseurs de colorants d'oxydation de type para, permettait d'obtenir, après application sur les fibres kératiniques et en particulier les cheveux, des teintures présentant des résistances à la lumière, aux lavages, aux intempéries et à la transpiration, particulièrement remarquables.The Applicant has just discovered, which is the subject of the invention, that the use of certain indole derivatives as couplers, with precursors of para-type oxidation dyes, made it possible to obtain, after application to keratin fibers and in particular hair, dyes having resistance to light, washing, bad weather and perspiration, which are particularly remarkable.
Un objet de l'invention est donc constitué par des compositions tinctoriales d'oxydation, destinées à être utilisées pour la teinture des fibres kératiniques, contenant au moins un précurseur de colorant d'oxydation de type para avec certains dérivés indoliques définis ci-après.An object of the invention therefore consists of dyeing oxidation compositions intended to be used for dyeing keratin fibers, containing at least one oxidation dye precursor of the para type with certain indole derivatives defined below.
Un autre objet de l'invention est constitué par le procédé de coloration des fibres kératiniques, en particulier des cheveux humains, mettant en oeuvre une telle composition.Another object of the invention consists of the process for dyeing keratin fibers, in particular human hair, using such a composition.
D'autres objets de l'invention apparaîtront à la lecture de la description et des exemples qui suivent.Other objects of the invention will appear on reading the description and the examples which follow.
La composition tinctoriale d'oxydation conforme à l'invention, destinée à être utilisée pour la teinture des fibres kératiniques et en particulier des cheveux, est essentiellement caractérisée par le fait qu'elle contient dans un milieu solvant acceptable, au moins un précurseur de colorant d'oxydation para et au moins un coupleur hétérocyclique, répondant à la formule (I) :The dyeing oxidation composition according to the invention, intended to be used for dyeing keratin fibers and in particular hair, is essentially characterized in that it contains in an acceptable solvent medium, at least one dye precursor of oxidation para and at least one heterocyclic coupler, corresponding to formula (I):
( I ) dans laquelle Ri désigne un atome d'hydrogène, un radical alkyle en C1-C4; Rg et R3, identiques ou differents, désignent un atome d'hydrogène, un radical alkyle inférieur en C1-C4, un radical carboxyle ou un radical alcoxycarbonyle; ainsi que leurs sels.(I) in which Ri denotes a hydrogen atom, a C1-C4 alkyl radical; Rg and R3, identical or different, denote a hydrogen atom, a lower C1-C4 alkyl radical, a carboxyl radical or an alkoxycarbonyl radical; as well as their salts.
Parmi les composés de formule (I), les composes particulièrement préférés sont les composés dans lesquels le radical alkyle désigne méthyle, éthyle; le radical alcoxycarbonyle désigne méthoxy ou éthoxy-carbonyle.Among the compounds of formula (I), the particularly preferred compounds are the compounds in which the alkyl radical denotes methyl, ethyl; the alkoxycarbonyl radical denotes methoxy or ethoxy-carbonyl.
Parmi ces composés, on peut citer l'hydroxy-6 indole, l'hydroxy-6 méthoxycarbonyl-3 indole, l'hydroxy-6 méthyl-1 méthoxycarbonyl-3 indole, l'hydroxy-6 méthyl-1 diméthoxycarbonyl-2,3 indole, l'hydroxy-6 diméthyl-1,2 indole, l'hydroxy-6 méthyl-2 indole, l'hydroxy-6 carboxy-2 indole, l'hydroxy-6 diméthyl-2,3 indole, l'hydroxy-6 carboxy-3 indole, l'hydroxy-6 ethoxycarbony1-3 indole, l'hydroxy-6 éthoxy carbonyl-2 indole, l'hydroxy-6 méthyl-3 indole, l'hydroxy-6 mêthyl-1 indole.Among these compounds, mention may be made of 6-hydroxy indole, 6-hydroxy methoxycarbonyl-3 indole, 6-hydroxy-methyl-1 methoxycarbonyl-3 indole, 6-hydroxy-methyl-1 dimethoxycarbonyl-2,3 indole, 6-hydroxy-1,2-dimethyl indole, 6-hydroxy-2-methyl indole, 6-hydroxy-2-carboxy indole, 6-hydroxy-2,3-dimethyl indole, hydroxy- 6 carboxy-3 indole, hydroxy-6 ethoxycarbony1-3 indole, hydroxy-6 ethoxy carbonyl-2 indole, hydroxy-6 methyl-3 indole, hydroxy-6 methyl-1 indole.
Les précurseurs de colorants de type para sont des composés qui ne sont pas des colorants en eux-mêmes, mais qui forment un colorant par un processus de condensation oxydative, soit sur eux-mêmes, soit en présence d'un coupleur ou modificateur.Para type dye precursors are compounds which are not dyes in themselves, but which form a dye by an oxidative condensation process, either on themselves or in the presence of a coupler or modifier.
Ces composés comportent des groupements fonctionnels, en particulier amino ou hydroxy, en position para l'un par rapport à l'autre.These compounds contain functional groups, in particular amino or hydroxy, in the para position relative to one another.
Ces précurseurs de colorants de type para sont en particulier choisis parmi les paraphénylènediamines, les para-aminophénols, les précurseurs hétérocycliques para, comme la diamino-2,5 pyridine, l'hydroxy-2 amino-5 pyridine, la tétra-amino-pyrimidine.These para-type dye precursors are in particular chosen from paraphenylenediamines, para-aminophenols, heterocyclic para precursors, such as 2,5-diamino pyridine, 2-hydroxy-5-pyridine, tetra-amino-pyrimidine .
A titre de paraphénylènediamines, on peut plus particulièrement citer les composés répondant à la formule (II) ci-après :Mention may more particularly be made, as paraphenylenediamines, of the compounds corresponding to formula (II) below:
(II) dans laquelle R4, R5 et Rg, identiques ou différents, représentent un atome d'hydrogène ou d'halogène, un radical alkyle ayant 1 à 4 atomes de carbone, un radical alcoxy ayant 1 à 4 atomes de carbone, R7 et Rg, identiques ou différents, représentent un atome d'hydrogène, un radical alkyle, hydroxyalkyle, alcoxy-alkyle, carbamylalkyle, mésylaminoalkyle, acétylamino-alkyle, urêidoalkyle, carbéthoxyaminoalkyle, pipéridinc-alkyle, morpholinoalkyle. Ces groupes alkyle ou alcoxy ayant de 1 à 4 atomes de carbone, ou bien R7 et Rg forment, conjointement avec l'atome d'azote auquel ils sont liés, un hétérocycle pipéridino ou morpholino sous réserve que R4 ou Rg représentent un atome d'hydrogène lorsque R7 et Rg ne représentent pas un atome d'hydrogène, ainsi que les sels de ces composés.(II) in which R4, R5 and Rg, identical or different, represent a hydrogen or halogen atom, an alkyl radical having 1 to 4 carbon atoms, an alkoxy radical having 1 to 4 carbon atoms, R7 and Rg, identical or different, represent a hydrogen atom, an alkyl, hydroxyalkyl, alkoxy-alkyl, carbamylalkyl, mesylaminoalkyl, acetylamino-alkyl, ureidoalkyl, carbethoxyaminoalkyl, piperidinc-alkyl, morpholinoalkyl radical. These alkyl or alkoxy groups having from 1 to 4 carbon atoms, or else R7 and Rg form, together with the nitrogen atom to which they are linked, a piperidino or morpholino heterocycle, provided that R4 or Rg represent an atom of hydrogen when R7 and Rg do not represent a hydrogen atom, as well as the salts of these compounds.
Parmi les composés de formule (II), on peut plus particulièrement citer la p-phénylènediamine, la p-toluylènediamine, la méthoxyparaphênylènediamine, la chloroparaphénylènediamine, la dimêthyl-2,6 p-phénylène diamine, la diméthyl-2,5 paraphénylènediamine, la méthyl-2 méthoxy-5 paraphénylènediamine, la diméthyl-2,6 mêthoxy-5 paraphénylènediamine, la N,N-diméthyl paraphénylènediamine, la mêthyl-3 amino-4 N,N-diêthyl aniline, la N,N-di(ß-hydroxyéthyl)paraphénylènediamine, la mêthyl-3 amino-4 N,N-di-(ß-hydroxyéthyl)aniline, la chloro-3 amino-4 N,N-di-(ß-hydroxyéthyl)aniline, 1'amino-4 N,N-(éthyl carhamylméthyl)aniline, la mêthyl-3 amino-4 N,N-(êthyl carhamylméthyl)aniline, l'amino-4 N,N-(éthyl ß-pipéridinoéthyl)aniline, la mêthyl-3 amino-4 N,N-(êthyl ß-pipéridinoéthyl)aniline, l'amino-4 N,N-(éthyl ß-morpholinoéthyl)aniline, la méthyl-3 amino-4 N,N-(éthyl ß-morpholinoéthyl)aniline, l'amino-4 N,N-(éthyl ß-acétylaminoéthyl)aniline, l'amino-4 N-(ß-méthoxyéthyl)aniline, la méthyl-3 amino-4 N,N-(éthyl ß-acétylaminoéthyl)an.il.ine, l'amino-4 N,N-(éthyl ß-mésylaminoéthyl)aniline, la mêthyl-3 amino-4 N,N-(éthyl ß-mésylaminoéthyl)aniline, l'amino-4 N,N-(êthyl ß-sulfoéthyl)aniline, la mêthyl-3 amino-4 N,N-(êthyl ß-sulfoéthyl)aniline, laAmong the compounds of formula (II), there may be mentioned more particularly p-phenylenediamine, p-toluylenediamine, methoxyparaphenylenediamine, chloroparaphenylenediamine, 2,6-dimethylphenyl diamine, 2,5-dimethyl paraphenylenediamine, 2-methyl-5-methoxy-paraphenylenediamine, 2,6-dimethyl-5-methoxy-paraphenylenediamine, N, N-dimethyl paraphenylenediamine, 3-methyl-4-amino, N-diethyl aniline, N, N-di (ß- hydroxyethyl) paraphenylenediamine, 3-methyl-4-amino, N-di- (ß-hydroxyethyl) aniline, 3-chloro-4-amino, N-di- (ß-hydroxyethyl) aniline, 4-amino , N- (ethyl carhamylmethyl) aniline, 3-methyl-4-amino, N- (ethyl carhamylmethyl) aniline, 4-amino N, N- (ethyl ß-piperidinoethyl) aniline, 3-methyl-4 amino N, N- (ethyl ß-piperidinoethyl) aniline, amino-4 N, N- (ethyl ß-morpholinoethyl) aniline, methyl-3 amino-4 N, N- (ethyl ß-morpholinoethyl) aniline, amino-4 N, N- (ethyl ß-acetylaminoethyl) aniline , amino-4 N- (ß-methoxyethyl) aniline, methyl-3 amino-4 N, N- (ethyl ß-acetylaminoethyl) an.il.ine, amino-4 N, N- (ethyl ß -mesylaminoethyl) aniline, 3-methyl-4-amino, N- (ethyl ß-mesylaminoethyl) aniline, 4-amino, N- (ethyl ß-sulfoethyl) aniline, 3-amino-4 N, N- (ethyl ß-sulfoethyl) aniline, the
morpholine, lamorpholine, the
Ces précurseurs de colorants par oxydation de type para peuvent être introduits dans la composition tinctoriale, soit sous forme de base libre, soit sous forme de sels, tels que sous forme de chlorhydrate, de bromhydrate ou de sulfate.These para-oxidation dye precursors can be introduced into the dye composition, either in the form of a free base or in the form of salts, such as in the form of hydrochloride, hydrobromide or sulfate.
Parmi les p-aminophénols, on peut citer le p-aminophénol, le méthyl-2 amino-4 phénol, le mêthyl-3 amino-4 phénol, le chloro-2 amino-4 phénol, le chloro-3 amino-4 phenol, le diméthy1-2,6 amino-4 phénol, le dimethy1-3,5 amino-4 phénol, le diméthyl-2,3 amino-4 phénol, le diméthyl-2,5 amino-4 phénol, 1'hydroxyméthyl-2 amino-4 phénol, le (ß-hydroxyéthyl)-2 amino-4 phénol, le methoxy-2 amino-4 phénol, le méthoxy-3 amino-4 phénol.Among the p-aminophenols, mention may be made of p-aminophenol, 2-methyl-4-amino phenol, 3-methyl-4-amino phenol, 2-chloro-4 amino phenol, 3-chloro-4 amino phenol, dimethy1-2,6 amino-4 phenol, dimethy1-3,5 amino-4 phenol, dimethyl-2,3 amino-4 phenol, dimethyl-2,5 amino-4 phenol, hydroxymethyl-2 amino -4 phenol, (ß-hydroxyethyl) -2 amino-4 phenol, 2-methoxy-4-amino phenol, 3-methoxy-4-amino phenol.
Les compositions tinctoriales conformes à l'invention peuvent en outre contenir des précurseurs de colorants d'oxydation de type ortho, tels que les orthoaminophenols, comme 1'amino—1 hydroxy—2 benzène, le méthyl-6 hydroxy-1 amino-2 benzène, le méthyl-4 amino-1 hydroxy-2 benzène; les orthophênylènediamines, les orthodiphénols.The dye compositions in accordance with the invention may also contain precursors of oxidation dyes of the ortho type, such as orthoaminophenols, such as amino-1 hydroxy-2 benzene, methyl-6 hydroxy-1 amino-2 benzene , 4-methyl-1 amino-2-hydroxy benzene; orthophenylenediamines, orthodiphenols.
Les compositions tinctoriales peuvent egalement contenir en plus du coupleur hétérocyclique répondant a la formule (I) ci—dessus, d'autres coupleurs connus en eux-mêmes, tels que les métadiphénols, les metaaminophénols, les métaphénylènediamines, les metaacylaminophênols, les métauréidophénols, les métacarbalcoxyaminophénols, 1 ' C?(-naphtol, les coupleurs possédant un groupe méthylène actif tels que les composés ß-cétoniques et les pyrazolones.The dye compositions may also contain, in addition to the heterocyclic coupler corresponding to formula (I) above, other couplers known in themselves, such as metadiphenols, metaaminophenols, metaphenylenediamines, metaacylaminophenols, metaurideophenols, metacarbalcoxyaminophenols, C '(- naphthol, couplers having an active methylene group such as β-ketone compounds and pyrazolones.
On peut citer en particulier, à titre d'exemple, le dihydroxy-2,4 phénoxyéthanol, le dihydroxy-2,4 anisole, le métaaminophénol, le monornéthy léther de résorcine, le méthyl-2 amino-5 phenol, le méth^l-2 N-(ß-hydroxyéthy1)amino-5 phénol, le mêthyl-2 N-(ß-mésylaminoéthyl)amino-5 phénol, le diméthyl-2,6 amino-3 phénol, 1'hydroxy-6 benzomorpho-line, le diamino-2,4 anisole, le diamino-2,4 phénoxyéthanol, l'amino-6 benzomorpholine, le /p- ( ß-hydroxyéthy1) amino-2 amino-ÿphênox> éthanol, 1'amino-2 N-(ß-hydroxyéthyl)amino-4 anisole, le (diamino-2,4)phênyl.ß, ^-dihydroxypropyléther, la diamino-2,4 phénoxyéthylamine et leurs sels.Mention may in particular be made, by way of example, of 2,4-dihydroxy phenoxyethanol, 2,4-dihydroxy anisole, metaaminophenol, monornethy resorcin ether, 2-methyl-5-amino phenol, meth ^ 1 -2 N- (ß-hydroxyethyl) 5-amino phenol, 2-methyl N- (ß-mesylaminoethyl) 5-amino phenol, 2,6-dimethyl 3-amino phenol, 6-hydroxy benzomorpholine, 2,4-diamino anisole, 2,4-diamino phenoxyethanol, 6-amino benzomorpholine, / p- (ß-hydroxyethyl) 2-amino-amino-phenox> ethanol, 2-amino N- (ß -hydroxyethyl) amino-4 anisole, (2,4-diamino) phenyl.ß, ^ -dihydroxypropylether, 2,4-diamino phenoxyethylamine and their salts.
On peut rajouter à ces compositions, comme cela est bien connu dans l'état de la technique, notamment en vue de nuancer ou d'enrichir en reflets les colorations apportées par les précurseurs de colorants d'oxydation, des colorants directs tels que des colorants azoïques, anthraquinoniques ou les dérivés nitrês de la série benzênique.Direct dyes such as dyes can be added to these compositions, as is well known in the state of the art, in particular with a view to nuancing or enriching the coloring provided by the oxidation dye precursors. azo, anthraquinone or nitrous derivatives of the benzene series.
L'ensemble des précurseurs de colorants par oxydation de type para ainsi que les couple.urs utilisés dans les compositions tinctoriales -conformes à l'invention, représente de préférence de 0,3 à 7% en poids par rapport au poids de ladite composition. La concentration en composés (I) peut varier entre 0,05 et 3,5% en poids du poids total de la composition.All of the para-oxidation dye precursors as well as the pairs used in the dye compositions -in accordance with the invention, preferably represent from 0.3 to 7% by weight relative to the weight of said composition. The concentration of compounds (I) can vary between 0.05 and 3.5% by weight of the total weight of the composition.
Le milieu solvant acceptable est généralement aqueux et son pH peut varier entre 8 et 11, et il est de préférence compris entre 9 et 11.The acceptable solvent medium is generally aqueous and its pH can vary between 8 and 11, and it is preferably between 9 and 11.
Il est ajusté à la valeur désirée à l'aide d'un agent alcalinisant tel que l'ammoniaque, les carbonates alcalins, les alcanclamines comme la mono-, la di- ou la triéthanolamine.It is adjusted to the desired value using an alkalizing agent such as ammonia, alkali carbonates, alkanclamines such as mono-, di- or triethanolamine.
Les compositions tinctoriales conformes à l'invention contiennent également, dans leur forme de réalisation préférée, des agents tensio-actifs anioniques, cationiques, non-ioniques, amphotères ou leurs mélanges. Parmi ces agents tensio-actifs, on peut citer les alkylbenzènesulfonates, les alkylnaphtalènesulfonates, les sulfates, les éther-sulfates et les sulfonates d'alcools gras, les sels d'ammonium quaternaires tels que le bromure de triméthylcétylammonium, le bromure de cétylpyridinium; les êthanolamides d'acides gras éventuellement oxyéthylênês; les acides, les alcools ou les amines polyoxyéthylênês, les alcools polyglycérolés, les alkylphênols polyoxyéthylénés ou polyglycérolés, ainsi que les alkylsulfates polyoxyéthylénés.The dye compositions in accordance with the invention also contain, in their preferred embodiment, anionic, cationic, nonionic, amphoteric surfactants or mixtures thereof. Among these surfactants, mention may be made of alkylbenzenesulfonates, alkylnaphthalenesulfonates, sulfates, ether sulfates and sulfonates of fatty alcohols, quaternary ammonium salts such as trimethylketylammonium bromide, cetylpyridinium bromide; ethanolamides of fatty acids optionally oxyethylenated; polyoxyethylenated acids, alcohols or amines, polyglycerolated alcohols, polyoxyethylenated or polyglycerolated alkylphenols, as well as polyoxyethylenated alkylsulfates.
Ces agents tensio-actifs sont présents dans les compositions conformes à 1'invention dans des proportions comprises entre 0,5 et 55% en poids, et de préférence entre 2 et 50% en poids par rapport au poids total de la composition.These surfactants are present in the compositions in accordance with the invention in proportions of between 0.5 and 55% by weight, and preferably between 2 and 50% by weight relative to the total weight of the composition.
Ces compositions peuvent également contenir des solvants organiques pour solubiliser les composés qui ne seraient pas suffisamment solubles dans l'eau. Parmi ces solvants, on peut citer à titre d'exemple, les alcanols inférieurs en C1-C4, tels que .1'éthanol et 1'isopropanol; le glycêrol; les glycols ou éthers de glycol, comme le butoxy-2 éthanol, 1'êthylâneglycol, le propylèneglycol, le monoéthyléther et le monomêthylêther du diêthylèneglycol, ainsi que les alcools aromatiques comme l'alcool benzylique ou le phénoxyêthancl, les produits analogues ou leurs mélanges.These compositions can also contain organic solvents to dissolve the compounds which would not be sufficiently soluble in water. Among these solvents, mention may be made, by way of example, of C1-C4 lower alkanols, such as ethanol and isopropanol; glycerol; glycols or glycol ethers, such as 2-butoxyethanol, ethylane glycol, propylene glycol, monoethyl ether and the monomethyl ether of diethylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethancl, analogous products or mixtures thereof.
Les solvants sont présents de préférence dans une proportion comprise entre 1 et 40% en poids, et en particulier entre 5 et 30% en poids par rapport au poids total de la composition.The solvents are preferably present in a proportion of between 1 and 40% by weight, and in particular between 5 and 30% by weight relative to the total weight of the composition.
Les agents épaississants que l'on peut ajouter dans les compositions conformes â l'invention peuvent être choisis en particulier parmi 1'alginate de sodium, la gomme arabique, les dérivés de cellulose tels que la mêthylcellulose, 1'hydroxyêthylcellulose, 1'hydroxypropylcellulose, 1'hydroxymêthylcellulose, la carboxymêthylcellulose, les polymères d'acide acrylique, la gomme de xanthane. On peut également utiliser des agents épaississants minéraux, tels que la bentonite. Ces agents épaississants sont présents de préférence dans des proportions comprises entre 0,1 à 5%, et en particulier entre 0,2 et 3% en poids par rapport au poids total de la composition.The thickening agents which can be added to the compositions in accordance with the invention can be chosen in particular from sodium alginate, gum arabic, cellulose derivatives such as methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, Hydroxymethylcellulose, carboxymethylcellulose, acrylic acid polymers, xanthan gum. Mineral thickeners can also be used, such as bentonite. These thickening agents are preferably present in proportions of between 0.1 to 5%, and in particular between 0.2 and 3% by weight relative to the total weight of the composition.
Les agents antioxydants qui peuvent être présents dans les compositions sont choisis en particulier parmi le sulfite de sodium, l'acide thioglycolique, le bisulfite de sodium, l'acide ascorbique et 1'hydroquinone. Ces agents antioxydants sont présents dans la composition dans des proportions comprises entre 0,05 et 1,5% en poids par rapport au poids total de la composition.The antioxidant agents which may be present in the compositions are chosen in particular from sodium sulfite, thioglycolic acid, sodium bisulfite, ascorbic acid and hydroquinone. These antioxidant agents are present in the composition in proportions of between 0.05 and 1.5% by weight relative to the total weight of the composition.
Ces compositions peuvent également contenir d'autres adjuvants cosmêtiquement acceptables, tels que par exemple des agents de pénétration, . des agents séquestrants, des tampons, des parfums, etc.These compositions can also contain other cosmetically acceptable adjuvants, such as, for example, penetrating agents. sequestering agents, tampons, perfumes, etc.
Les compositions conformes à l'invention peuvent se présenter sous des formes diverses, telles que sous forme de liquides, de crèmes, de gels ou sous toute autre forme appropriée pour réaliser une teinture de fibres kératiniques et notamment des cheveux humains. Ces compositions peuvent être conditionnées en flacons aérosols en présence d'un agent propulseur.The compositions in accordance with the invention can be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratin fibers and in particular human hair. These compositions can be packaged in aerosol bottles in the presence of a propellant.
Les compositions tinctoriales' conformes à l'invention contenant un précurseur de colorant par oxydation de type para et un coupleur de formule ( I ), sont utilisées dans les procédés de teinture des fibres kératiniques et en particulier des cheveux humains, suivant un procédé mettant en oeuvre la révélation par un agent oxydant.The dye compositions' in accordance with the invention containing a para-oxidative dye precursor of the para type and a coupler of formula (I) are used in the dyeing processes for keratin fibers and in particular human hair, according to a process using revelation by an oxidizing agent.
Conformément à ce procédé, on mélange au moment de l'emploi, la composition tinctoriale décrite ci-dessus avec une solution oxydante en une quantité suffisante pour pouvoir développer une coloration, puis on applique le mélange obtenu sur les fibres kératiniques et en particulier, les cheveux humains.In accordance with this process, the dye composition described above is mixed at the time of use with an oxidizing solution in an amount sufficient to be able to develop a coloring, then the mixture obtained is applied to the keratin fibers and in particular, the human hair.
La solution oxydante contient des agents oxydants, tels que l'eau oxygénée, le peroxyde d'urée ou des perseis, tels que le persulfate d'ammonium. On utilise de préférence une solution d'eau oxygénée à 20 volumes.The oxidizing solution contains oxidizing agents, such as hydrogen peroxide, urea peroxide or perseis, such as ammonium persulfate. Preferably a solution of hydrogen peroxide at 20 volumes is used.
Le mélange obtenu est appliqué sur les cheveux et on laisse poser pendant 10 à 40 minutes, de préférence 15 à 30 minutes, après quoi on rince les cheveux, on les lave au shampooing, on les rince à nouveau et on les sèche.The mixture obtained is applied to the hair and left to stand for 10 to 40 minutes, preferably 15 to 30 minutes, after which the hair is rinsed, washed with shampoo, rinsed again and dried.
Le coupleur hétérocyclique de formule (i) défini ci-dessus peut également être mis en oeuvre dans un procédé à plusieurs étapes, consistant dans l'une des étapes, à appliquer le précurseur de colorant d'oxydation para au moyen d'une composition susdéfinie, et dans une autre étape, à appliquer le coupleur de formule (I).The heterocyclic coupler of formula (i) defined above can also be used in a multistage process, consisting in one of the stages, in applying the oxidation dye precursor para by means of a predefined composition. , and in another step, applying the coupler of formula (I).
L'agent oxydant peut être introduit tout juste avant l'application dans la composition appliquée dans le deuxième temps ou bien être additionné sur les fibres kératiniques elles-mêmes dans un troisième temps, les conditions de pose et de séchage ou de lavage étant identiques.The oxidizing agent can be introduced just before application in the composition applied in the second step or else be added to the keratin fibers themselves in a third step, the conditions for laying and drying or washing being identical.
Les exemples qui suivent sont destinés à illustrer l'invention sans pour autant présenter un caractère limitatif.The examples which follow are intended to illustrate the invention without however being limiting in nature.
EXEMPLE D'APPLICATION 1 On prépare le mélange tinctorial suivant : - Hydroxy-6 indole 0,33 g - p-phênylènediamine 0,27 g - Alcool oléique polyglycérolé à 2 moles de glycérol 4,5 g - Alcool oléique polyglycérolé à 4 moles de glycérol , 4,5 g - ETHOMEEN O 12 - Société ARMOON HESS _ 4,5 g CHEMICAL Ltd (oleylamine oxyéthylénêe à 12 moles d'oxyde d'éthylène) - COMPERLAN KD - Société HENKEL 9,0 g (diéthanolamide de coprah) - Propylèneglycol 4,0 g - Butoxy-2 éthanol 8,0 g - Ethanol 96° 6,0 g - MASQÜOL DTPA - Société PROTEX 2,0 g (sel pentasodique de l'acide diéthylène triamine pentacêtique) - Hydroquinone 0,15 g - Solution de bisulfite de sodium à 35°Ee 1,3 g - Ammoniaque 22°Be 10,0 g - Eau qsp 100,0 g - pH = 10,5APPLICATION EXAMPLE 1 The following dye mixture is prepared: - 6-hydroxy indole 0.33 g - p-phenylenediamine 0.27 g - Polyglycerolated oleic alcohol with 2 moles of glycerol 4.5 g - Polyglycerolated oleic alcohol with 4 moles glycerol, 4.5 g - ETHOMEEN O 12 - Company ARMOON HESS _ 4.5 g CHEMICAL Ltd (oleylamine oxyethylenated to 12 moles of ethylene oxide) - COMPERLAN KD - Company HENKEL 9.0 g (coconut diethanolamide) - Propylene glycol 4.0 g - Butoxy-2 ethanol 8.0 g - Ethanol 96 ° 6.0 g - MASQÜOL DTPA - PROTEX company 2.0 g (pentasodium salt of diethylene triamine pentacetic acid) - Hydroquinone 0.15 g - Sodium bisulfite solution at 35 ° Ee 1.3 g - Ammonia 22 ° Be 10.0 g - Water qs 100.0 g - pH = 10.5
Au moment de l'emploi, on ajoute 100 g d'eau oxygénée à 20 volumes. Le mélange appliqué 20 minutes à 34eC sur des cheveux naturellement blancs à 90% leur confère après shampooing et rinçage, une coloration brun moyen doré.At the time of use, 100 g of hydrogen peroxide are added to 20 volumes. The mixture applied 20 minutes at 34 ° C to naturally white hair at 90% gives them, after shampooing and rinsing, a medium golden brown coloring.
EXEMPLE D'APPLICATION 2 On prépare le mélange tinctorial suivant : - Hydroxy-6 indole 0,33 g - p-aminophénol 0,27 g - Alcool oléique polyglycérolé à 2 moles de glycérol 4,5 g - Alcool oléique polyglycérolé à 4 moles de glycérol 4,5 g - ETHOMEEN 0 12 - Société ARMOON HESS 4,5 g CHEMICAL Ltd (oleylamine oxyêthylénée à 12 moles d'oxyde d1 éthylène) - COMPERLAN KD - Société HENKEL 9,0 g (diêthanolamine de coprah) - Propylèneglycol 4,0 g - Butoxy-2 éthanol 8,0 g - Ethanol 96° 6,0 gAPPLICATION EXAMPLE 2 The following dye mixture is prepared: - 6-hydroxy indole 0.33 g - p-aminophenol 0.27 g - Polyglycerolated oleic alcohol with 2 moles of glycerol 4.5 g - Polyglycerolated oleic alcohol with 4 moles glycerol 4.5 g - ETHOMEEN 0 12 - Company ARMOON HESS 4.5 g CHEMICAL Ltd (oleylamine oxyethylenated with 12 moles of ethylene oxide) - COMPERLAN KD - Company HENKEL 9.0 g (diethanolamine from coconut) - Propylene glycol 4, 0 g - Butoxy-2 ethanol 8.0 g - Ethanol 96 ° 6.0 g
- MASQUOL DTPA - Société PROTEX- MASQUOL DTPA - PROTEX Company
(sel pentasodique de l'acide diêthylène triamine pentacêtique) 2,0 g - Hydroquinone 0,15 g - Solution de bisulfite de sodium à 35°Be 1,3 g - Ammoniaque 22°Be 10,0 g - Eau qsp 100,0 g - pH = 10,5(pentasodium salt of diethylene triamine pentacetic acid) 2.0 g - Hydroquinone 0.15 g - Sodium bisulfite solution at 35 ° Be 1.3 g - Ammonia 22 ° Be 10.0 g - Water qs 100.0 g - pH = 10.5
Au moment de l'emploi, on ajoute 100 g d'eau oxygénée à 20 volumes. Le mélange appliqué 20 minutes à 34°C sur des cheveux décolorés leur confère après shampooing et rinçage, une coloration beige doré.At the time of use, 100 g of hydrogen peroxide are added to 20 volumes. The mixture applied 20 minutes at 34 ° C to bleached hair gives them, after shampooing and rinsing, a golden beige color.
EXEMPLE D’APPLICATION 3 On prépare le mélange tinctorial suivant : - Hydroxy-6 méthyl-1 indole 0,73 g - Dichlorhydrate de bis-(ß-hydroxy éthyl)amino-4 aniline 1,34 g - CELLOSIZE ViP 03 - Société UNION CARBIDE 2,0 g (hydroxyéthylcellulose) - Laurylsulfate d'ammonium 5,0 g - Butoxy-2 éthanol 15,0 g - Alcool 96° 5,0 g - MASQUOL DTPA - Société PROTEX 2,0 g (sel pentasodique de l'acide diêthylène triamine pentacêtique) - Eau qsp 100,0 g - pH = 10,5APPLICATION EXAMPLE 3 The following dye mixture is prepared: - 6-hydroxy-1-methyl-indole 0.73 g - bis- (ß-hydroxyethyl) amino-4-aniline dihydrochloride 1.34 g - CELLOSIZE ViP 03 - Company UNION CARBIDE 2.0 g (hydroxyethylcellulose) - Ammonium lauryl sulfate 5.0 g - 2-Butoxyethanol 15.0 g - 96 ° alcohol 5.0 g - MASQUOL DTPA - PROTEX company 2.0 g (pentasodium salt of diethylene triamine pentacetic acid) - Water qs 100.0 g - pH = 10.5
Au moment de l'emploi, on ajoute 100 g d'eau oxygénée à 20 volumes. Le mélange appliqué 20 minutes à 34°C sur des cheveux naturellement blancs à 90% leur confère après shampooing et rinçage, une coloration gris violine.At the time of use, 100 g of hydrogen peroxide are added to 20 volumes. The mixture applied 20 minutes at 34 ° C to naturally white hair at 90% gives them, after shampooing and rinsing, a purple gray color.
Claims (20)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87337A LU87337A1 (en) | 1988-09-12 | 1988-09-12 | TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS AND DYEING METHODS USING THE SAME |
| CH3213/89A CH679551A5 (en) | 1988-09-12 | 1989-09-05 | |
| ZA896845A ZA896845B (en) | 1988-09-12 | 1989-09-07 | Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers,and dyeing processes using these compositions |
| AT0210089A AT400672B (en) | 1988-09-12 | 1989-09-07 | COLORING AGENTS AND DYEING METHODS FOR KERATINE FIBERS |
| GR890100568A GR1000461B (en) | 1988-09-12 | 1989-09-08 | Dying compositions for keratine fibres containing dying substances precursors by oxydation and indolic couplers and preparation process therefor |
| PT91663A PT91663B (en) | 1988-09-12 | 1989-09-08 | PROCESS FOR THE PREPARATION OF DYEING COMPOSITIONS FOR CERATINAL FIBERS CONTAINING PRECURSORS OF OXIDACAO COLORS AND INDOLIC COUPLERS, AND DYEING PROCESSES IN WHICH THESE COMPOSITIONS ARE LAID. |
| IT8967751A IT1232920B (en) | 1988-09-12 | 1989-09-11 | DYEING COMPOSITIONS FOR KERATINIC FIBERS CONTAINING PRECURSORS OF OXIDATION DYES AND PAIRS, AND DYEING PROCEDURES USING THESE COMPOSITIONS |
| AR89314892A AR245515A1 (en) | 1988-09-12 | 1989-09-11 | Tinctorial compositions for keratin fibres |
| BR898904562A BR8904562A (en) | 1988-09-12 | 1989-09-11 | DYE COMPOSITION FOR KERATIN FIBERS, SAME PREPARATION PROCESS AND DYE PROCESS FOR KERATIN FIBERS |
| GB8920524A GB2224518B (en) | 1988-09-12 | 1989-09-11 | Tinctorial compositions for keratin fibres |
| AU41207/89A AU626579B2 (en) | 1988-09-12 | 1989-09-11 | Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers, and dyeing processes using these compositions |
| ES8903090A ES2016162A6 (en) | 1988-09-12 | 1989-09-11 | DYEING COMPOSITIONS FOR KERATIN FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COULATORS AND STAINING PROCEDURE USED BY THESE COMPOSITIONS. |
| BE8900961A BE1002235A4 (en) | 1988-09-12 | 1989-09-11 | TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS AND DYEING METHODS USING THE SAME. |
| FR8911815A FR2636236B1 (en) | 1988-09-12 | 1989-09-11 | TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS, AND DYEING METHODS USING THE SAME |
| DE3930473A DE3930473B4 (en) | 1988-09-12 | 1989-09-12 | Colorants for keratinic fibers containing precursors of oxidation dyes and indole couplers, and processes for their preparation and dyeing processes using these agents |
| KR1019890013240A KR0172112B1 (en) | 1988-09-12 | 1989-09-12 | Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers, and dyeing processes using these compositions |
| JP1236768A JP2744080B2 (en) | 1988-09-12 | 1989-09-12 | Dyeing composition of keratinous fiber and method for producing the same |
| NL8902281A NL194230C (en) | 1988-09-12 | 1989-09-12 | Paint preparation for keratin-containing threads, method for preparing a paint preparation and method for dyeing keratin-containing threads. |
| CA000611132A CA1341195C (en) | 1988-09-12 | 1989-09-12 | Tinctorial compositions for keratinic fibers and dyeing process using these compositions |
| US07/871,116 US5279620A (en) | 1988-09-12 | 1992-04-20 | Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers, and dyeing processes using these compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87337A LU87337A1 (en) | 1988-09-12 | 1988-09-12 | TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS AND DYEING METHODS USING THE SAME |
| LU87337 | 1988-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87337A1 true LU87337A1 (en) | 1990-04-06 |
Family
ID=19731089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87337A LU87337A1 (en) | 1988-09-12 | 1988-09-12 | TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING OXIDATION DYE PRECURSORS AND INDOLIC COUPLERS AND DYEING METHODS USING THE SAME |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JP2744080B2 (en) |
| KR (1) | KR0172112B1 (en) |
| AR (1) | AR245515A1 (en) |
| AT (1) | AT400672B (en) |
| AU (1) | AU626579B2 (en) |
| BE (1) | BE1002235A4 (en) |
| BR (1) | BR8904562A (en) |
| CA (1) | CA1341195C (en) |
| CH (1) | CH679551A5 (en) |
| DE (1) | DE3930473B4 (en) |
| ES (1) | ES2016162A6 (en) |
| FR (1) | FR2636236B1 (en) |
| GB (1) | GB2224518B (en) |
| GR (1) | GR1000461B (en) |
| IT (1) | IT1232920B (en) |
| LU (1) | LU87337A1 (en) |
| NL (1) | NL194230C (en) |
| PT (1) | PT91663B (en) |
| ZA (1) | ZA896845B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2659228B1 (en) * | 1990-03-08 | 1994-10-14 | Oreal | PROCESS FOR DYEING KERATINIC FIBERS WITH 6 OR 7-MONOHYDROXY-INDOLES WITH ACID PH AND COMPOSITIONS USED THEREOF. |
| FR2689761B1 (en) * | 1992-04-09 | 1995-06-23 | Oreal | PROCESS FOR DYEING KERATINIC FIBERS IN AN ALKALINE MEDIUM USING SUBSTITUTED PARAAMINOPHENOLS IN POSITION 2 IN ASSOCIATION WITH 6-OR 7-HYDROXYINDOLE AND COMPOSITIONS USED IN THE PROCESS. |
| JP4373497B2 (en) | 1996-06-19 | 2009-11-25 | ローン−プーラン・ロレ・リミテツド | Substituted azabicyclo compounds and their use as inhibitors of TNF and cyclic AMP phosphodiesterase production |
| JP5990319B2 (en) | 2012-03-27 | 2016-09-14 | ザ プロクター アンド ギャンブル カンパニー | Hair dye composition comprising amino-2,6-dimethylphenol and 1,4-phenylenediamine type developer, method and kit comprising the composition |
| EP2830579B1 (en) | 2012-03-27 | 2020-02-26 | Noxell Corporation | Hair colorant compositions comprising 3-amino 2,6 dimethylphenol, methods, and kits comprising the compositions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU56102A1 (en) * | 1968-05-17 | 1970-01-14 | ||
| US4013404A (en) * | 1970-12-06 | 1977-03-22 | American Cyanamid Company | Method of dyeing hair with indolines, indoles and indazoles |
| US4776857A (en) * | 1986-11-21 | 1988-10-11 | Repligen Corporation | Use of hydroxylated indoles as dye precursors |
| LU86833A1 (en) * | 1987-04-02 | 1988-12-13 | Oreal | PROCESS FOR DYEING KERATINIC FIBERS WITH 5,6-DIHYDROXYINDOLE ASSOCIATED WITH IODIDE AND A HYDROGEN PEROXIDE COMPOSITION WITH ALKALINE PH |
| LU86947A1 (en) * | 1987-07-17 | 1989-03-08 | Oreal | PROCESS FOR DYEING KERATINIC FIBERS, ESPECIALLY HUMAN, WITH 5- (HYDROXY OR-METHOXY) 6-HYDROXYINDOLE |
-
1988
- 1988-09-12 LU LU87337A patent/LU87337A1/en unknown
-
1989
- 1989-09-05 CH CH3213/89A patent/CH679551A5/fr not_active IP Right Cessation
- 1989-09-07 ZA ZA896845A patent/ZA896845B/en unknown
- 1989-09-07 AT AT0210089A patent/AT400672B/en not_active IP Right Cessation
- 1989-09-08 GR GR890100568A patent/GR1000461B/en not_active IP Right Cessation
- 1989-09-08 PT PT91663A patent/PT91663B/en not_active IP Right Cessation
- 1989-09-11 AU AU41207/89A patent/AU626579B2/en not_active Expired
- 1989-09-11 ES ES8903090A patent/ES2016162A6/en not_active Expired - Lifetime
- 1989-09-11 FR FR8911815A patent/FR2636236B1/en not_active Expired - Lifetime
- 1989-09-11 BR BR898904562A patent/BR8904562A/en not_active IP Right Cessation
- 1989-09-11 AR AR89314892A patent/AR245515A1/en active
- 1989-09-11 IT IT8967751A patent/IT1232920B/en active
- 1989-09-11 GB GB8920524A patent/GB2224518B/en not_active Expired - Lifetime
- 1989-09-11 BE BE8900961A patent/BE1002235A4/en not_active IP Right Cessation
- 1989-09-12 JP JP1236768A patent/JP2744080B2/en not_active Expired - Lifetime
- 1989-09-12 KR KR1019890013240A patent/KR0172112B1/en not_active Expired - Lifetime
- 1989-09-12 CA CA000611132A patent/CA1341195C/en not_active Expired - Lifetime
- 1989-09-12 NL NL8902281A patent/NL194230C/en not_active IP Right Cessation
- 1989-09-12 DE DE3930473A patent/DE3930473B4/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU4120789A (en) | 1990-03-15 |
| AU626579B2 (en) | 1992-08-06 |
| GB8920524D0 (en) | 1989-10-25 |
| DE3930473A1 (en) | 1990-03-15 |
| BR8904562A (en) | 1990-05-01 |
| IT1232920B (en) | 1992-03-05 |
| AT400672B (en) | 1996-02-26 |
| JPH02121912A (en) | 1990-05-09 |
| IT8967751A0 (en) | 1989-09-11 |
| DE3930473B4 (en) | 2006-04-27 |
| NL194230C (en) | 2001-10-02 |
| CH679551A5 (en) | 1992-03-13 |
| KR0172112B1 (en) | 1999-02-01 |
| ATA210089A (en) | 1995-07-15 |
| BE1002235A4 (en) | 1990-10-30 |
| ES2016162A6 (en) | 1990-10-16 |
| GB2224518A (en) | 1990-05-09 |
| JP2744080B2 (en) | 1998-04-28 |
| PT91663A (en) | 1990-03-30 |
| ZA896845B (en) | 1991-05-29 |
| FR2636236B1 (en) | 1993-10-22 |
| AR245515A1 (en) | 1994-01-31 |
| GB2224518B (en) | 1992-07-22 |
| NL8902281A (en) | 1990-04-02 |
| KR900004317A (en) | 1990-04-12 |
| GR1000461B (en) | 1992-07-30 |
| NL194230B (en) | 2001-06-01 |
| PT91663B (en) | 1995-08-09 |
| FR2636236A1 (en) | 1990-03-16 |
| CA1341195C (en) | 2001-02-27 |
| GR890100568A (en) | 1990-10-31 |
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| CH675205A5 (en) | ||
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| CH675719A5 (en) | ||
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| FR2779948A1 (en) | TINCTORIAL COMPOSITION CONTAINING 1,8-BIS- (2,5-DIAMINOPHENOXY) -3,5-DIOXAOCTANE, AN ADDITIONAL OXIDATION BASE AND A COUPLER, AND DYEING METHODS |