NL8902281A - PAINT PREPARATIONS FOR KERATIN-CONTAINING THREADS CONTAINING PRE-PREVENTS OF OXIDATING DYES AND INDOLE-COUPLING AGENTS AND METHODS OF APPLICATION USING THESE PREPARATIONS. - Google Patents
PAINT PREPARATIONS FOR KERATIN-CONTAINING THREADS CONTAINING PRE-PREVENTS OF OXIDATING DYES AND INDOLE-COUPLING AGENTS AND METHODS OF APPLICATION USING THESE PREPARATIONS. Download PDFInfo
- Publication number
- NL8902281A NL8902281A NL8902281A NL8902281A NL8902281A NL 8902281 A NL8902281 A NL 8902281A NL 8902281 A NL8902281 A NL 8902281A NL 8902281 A NL8902281 A NL 8902281A NL 8902281 A NL8902281 A NL 8902281A
- Authority
- NL
- Netherlands
- Prior art keywords
- amino
- preparation
- aminophenol
- methyl
- aniline
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 55
- 239000007822 coupling agent Substances 0.000 title claims description 21
- 239000003973 paint Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 claims description 51
- -1 p-toluylenediamine Chemical compound 0.000 claims description 33
- 210000004209 hair Anatomy 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000000975 dye Substances 0.000 claims description 20
- 238000004043 dyeing Methods 0.000 claims description 20
- 239000002243 precursor Substances 0.000 claims description 20
- 230000001590 oxidative effect Effects 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- 102000011782 Keratins Human genes 0.000 claims description 14
- 108010076876 Keratins Proteins 0.000 claims description 14
- 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 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-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
- GPJJASIJVRXZFI-UHFFFAOYSA-N 4-methoxybenzene-1,3-diol Chemical compound COC1=CC=C(O)C=C1O GPJJASIJVRXZFI-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 claims description 3
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 claims description 3
- PSTUGXWVTKXNGK-UHFFFAOYSA-N 2-anilino-n-ethylacetamide Chemical compound CCNC(=O)CNC1=CC=CC=C1 PSTUGXWVTKXNGK-UHFFFAOYSA-N 0.000 claims description 3
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
- UBKPLLYABUUFCE-UHFFFAOYSA-N 4-amino-2,3-dimethylphenol Chemical compound CC1=C(C)C(O)=CC=C1N UBKPLLYABUUFCE-UHFFFAOYSA-N 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229960005323 phenoxyethanol Drugs 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
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-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
- 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
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims description 2
- MUQLIBVTHAUUNH-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)-2-methylanilino]ethanol Chemical compound CC1=CC(N)=CC=C1N(CCO)CCO MUQLIBVTHAUUNH-UHFFFAOYSA-N 0.000 claims description 2
- KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-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
- 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
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-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
- OMVFXCQLSCPJNR-UHFFFAOYSA-N 4-amino-2,6-dimethylphenol Chemical compound CC1=CC(N)=CC(C)=C1O OMVFXCQLSCPJNR-UHFFFAOYSA-N 0.000 claims description 2
- NZMFZUGEOCZRAX-UHFFFAOYSA-N 4-amino-2-(2-hydroxyethyl)phenol Chemical compound NC1=CC=C(O)C(CCO)=C1 NZMFZUGEOCZRAX-UHFFFAOYSA-N 0.000 claims description 2
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 claims description 2
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 claims description 2
- MCNBYOWWTITHIG-UHFFFAOYSA-N 4-amino-2-methoxyphenol Chemical compound COC1=CC(N)=CC=C1O MCNBYOWWTITHIG-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
- XCJRRZLPXALCIP-UHFFFAOYSA-N 4-n-(2-methoxyethyl)benzene-1,4-diamine Chemical compound COCCNC1=CC=C(N)C=C1 XCJRRZLPXALCIP-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
- TVOSOIXYPHKEAR-UHFFFAOYSA-N 4-piperidin-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCCCC1 TVOSOIXYPHKEAR-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
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl 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
- 239000000872 buffer Substances 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 230000001143 conditioned effect Effects 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 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 description 2
- 239000000982 direct dye Substances 0.000 claims description 2
- 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 description 2
- 239000000499 gel Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- TYLFICUVJRBFNX-UHFFFAOYSA-N methyl 6-hydroxy-1-methylindole-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=CN(C)C2=C1 TYLFICUVJRBFNX-UHFFFAOYSA-N 0.000 claims description 2
- OYZMJHNFWMBBQC-UHFFFAOYSA-N methyl 6-hydroxy-1h-indole-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=CNC2=C1 OYZMJHNFWMBBQC-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
- 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
- LXTAFGWFPZQHRB-UHFFFAOYSA-N 1-anilinobutane-2-sulfonic acid Chemical compound CCC(S(O)(=O)=O)CNC1=CC=CC=C1 LXTAFGWFPZQHRB-UHFFFAOYSA-N 0.000 claims 1
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 claims 1
- AQUZPBABSUBRLS-UHFFFAOYSA-N 2-[4-amino-2-chloro-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C(Cl)=C1 AQUZPBABSUBRLS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 claims 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 claims 1
- YGRFRBUGAPOJDU-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-2-methylphenol Chemical compound CC1=CC=C(NCCO)C=C1O YGRFRBUGAPOJDU-UHFFFAOYSA-N 0.000 claims 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims 1
- HSRWFKHHKHVPCJ-UHFFFAOYSA-N N-(1-anilinobutan-2-yl)acetamide Chemical compound C(C)C(CNC1=CC=CC=C1)NC(C)=O HSRWFKHHKHVPCJ-UHFFFAOYSA-N 0.000 claims 1
- KRXGXGPRRQMIBS-UHFFFAOYSA-N N-(2-piperidin-1-ylbutyl)aniline Chemical compound C(C)C(CNC1=CC=CC=C1)N1CCCCC1 KRXGXGPRRQMIBS-UHFFFAOYSA-N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- XOUHVMVYFOXTMN-UHFFFAOYSA-N ethyl 1h-indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CNC2=C1 XOUHVMVYFOXTMN-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- MLQKWJAVASMXOD-UHFFFAOYSA-N n-[2-(3-hydroxy-4-methylanilino)ethyl]methanesulfonamide Chemical compound CC1=CC=C(NCCNS(C)(=O)=O)C=C1O MLQKWJAVASMXOD-UHFFFAOYSA-N 0.000 claims 1
- 229960001755 resorcinol Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 14
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 5
- 229920006317 cationic polymer Polymers 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- 229940001584 sodium metabisulfite Drugs 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 3
- AIMWCCSARFYZCK-UHFFFAOYSA-N 3-methyl-1h-indol-7-ol Chemical compound C1=CC=C2C(C)=CNC2=C1O AIMWCCSARFYZCK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229960003330 pentetic acid Drugs 0.000 description 3
- 238000010992 reflux Methods 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
- AEFUSISIFJGCHA-UHFFFAOYSA-N 1-methyl-6-phenylmethoxyindole Chemical compound C1=C2N(C)C=CC2=CC=C1OCC1=CC=CC=C1 AEFUSISIFJGCHA-UHFFFAOYSA-N 0.000 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 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
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- PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- GDOIKKMNCIMDAO-UHFFFAOYSA-N 5-amino-1h-pyridin-2-one Chemical compound NC1=CC=C(O)N=C1 GDOIKKMNCIMDAO-UHFFFAOYSA-N 0.000 description 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 description 1
- FPMICYBCFBLGOZ-UHFFFAOYSA-N 6-phenylmethoxy-1h-indole Chemical compound C=1C=C2C=CNC2=CC=1OCC1=CC=CC=C1 FPMICYBCFBLGOZ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000084 Gum arabic Chemical class 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 150000001298 alcohols Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 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
- 239000000987 azo dye Substances 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
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- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000490 cosmetic additive Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 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 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
- 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 239000005457 ice water Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 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
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 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
- 239000003607 modifier Substances 0.000 description 1
- HRQSQGJJMVRATE-UHFFFAOYSA-N n-(1-anilinobutan-2-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC(CC)CNC1=CC=CC=C1 HRQSQGJJMVRATE-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- 229910000029 sodium carbonate Inorganic materials 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
- Life Sciences & Earth Sciences (AREA)
- Health & Medical 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
Verfpreparaten voor keratinehoudende draden die voorlopers van oxidatie-kleurstoffen en indoolkoppelingsmiddelen bevatten en verfwerkwijzen waarbij deze preparaten worden toegepast.Keratin-containing filament paint compositions containing precursors of oxidation dyes and indole coupling agents and dyeing processes using these preparations.
De onderhavige uitvinding heeft betrekking op nieuwe verfpreparaten voor keratine bevattende draden en in het bijzonder voor menselijke haren, die voorlopers van oxidatiekleurstoffen en indoolkoppelingsmiddelen bevatten, alsmede een verfwerkwijze waarbij dergelijke preparaten worden toegepast.The present invention relates to novel dyeing compositions for keratin-containing filaments, and in particular for human hair, containing oxidation dye precursors and indole coupling agents, and a dyeing method using such compositions.
Het is bekend keratine bevattende draden en in het bijzonder menselijke haren te verven met verfpreparaten die voorlopers van oxidatiekleurstoffen en in het bijzonder van parafenyleendiaminen, van ortho- of para-aminofenolen in het algemeen aangeduid als "oxidatie-bases", bevatten.It is known to dye keratin-containing threads, and in particular human hairs, with paint compositions containing precursors of oxidation dyes and in particular of paraphenylenediamines, of ortho or para-aminophenols generally referred to as "oxidation bases".
Men weet ook dat men de verkregen kleuren kan doen variëren met deze oxidatiebases door in combinatie met deze bases te gebruiken koppelingsmiddelen ook wel genoemd kleurmodificeermiddelen en meer in het bijzonder aromatische metadiamines, meta-aminofenolen en metadifeno-len.It is also known that the colors obtained can be varied with these oxidation bases by coupling agents also used in combination with these bases, also referred to as color modifiers and more particularly aromatic metadiamines, metamino phenols and metadiphenols.
Men zoekt, op het gebied van capillaire verving, voorlopers van oxidatiekleurstoffen of koppelingsmiddelen die het mogelijk maken aan de haren, in alkalisch oxiderend milieu dat algemeen wordt toegepast bij de oxidatieverving, een kleur die een voldoende bestandheid tegen licht, tegen wassen, tegen weer en wind en tegen zweet bezit.In the field of capillary dyeing, precursors of oxidation dyes or coupling agents which make it possible to hair, in alkaline oxidizing medium commonly used in oxidation dyeing, are being sought, a color having sufficient resistance to light, washing, weathering and wind and against sweat.
Aanvraagster heeft nu gevonden en dat is het onderwerp van de onderhavige uitvinding dat het gebruik van bepaalde indoolderivaten in de hoedanigheid van koppelingsmiddelen, met voorlopers van oxidatie-kleurmiddelen van het type para, het mogelijk maken na aanbrengen op de keratine bevattende draden en in het bijzonder haren vervingen te verkrijgen met bestandheid tegen licht, tegen wassen, tegen weer en wind en tegen zweet, hetgeen bijzonder verrassend is.Applicant has now found and that is the subject of the present invention that the use of certain indole derivatives in the capacity of coupling agents, with precursors of oxidation dyes of the type para, make it possible after application to the keratin-containing threads and in particular hair replacements to be obtained with resistance to light, washing, wind and weather and sweat, which is particularly surprising.
Een onderwerp van de uitvinding bestaat dus uit oxidatieve verfpreparaten, die bestemd zijn om te worden toegepast voor het verven van keratine bevattende draden, die ten minste één voorloper van oxidatiekleurstof van het type para met bepaalde indoolderivaten die hierna gedefinieerd worden bevatten.Thus, an object of the invention is oxidative dyeing compositions intended to be used for dyeing keratin-containing filaments containing at least one para oxidation dye precursor with certain indole derivatives defined below.
Een ander doel van de uitvinding bestaat uit de verfwerkwijze van keratine bevattende draden, in het bijzonder menselijke haren, waarbij een dergelijk preparaat wordt toegepast.Another object of the invention is the dyeing process of keratin-containing threads, in particular human hair, using such a preparation.
Andere doeleinden van de uitvinding zullen blijken bij het lezen an de beschrijving en de voorbeelden die hier volgen.Other objects of the invention will become apparent upon reading the description and the examples that follow.
Het oxidatieve verfpreparaat volgens de uitvinding, dat bestemd is om te worden gebruikt voor het verven van keratine bevattende draden en in het bijzonder haren, bestaat in hoofdzaak uit het feit dat het in een aanvaardbaar oplosmiddelmilieu, ten minste één voorloper van oxidatieve parakleurstof bevat en ten minste één heterocyclisch koppelingsmiddel, met de algemene formule (1) van het formuleblad, waarin OH de plaatsen 6 of 7 van de aromatische kern bezet en een waterstofatoom, een C^-C alkylrest betekent; R£ en gelijk of verschillend zijn en een waterstofatoom, een Cj-Cty alkylrest, een carboxylrest of een C-pCzj. alkoxycarbonylrest betekenen; alsmede hun zouten.The oxidative dyeing composition according to the invention, which is intended to be used for dyeing keratin-containing threads and in particular hairs, mainly consists in the fact that in an acceptable solvent environment it contains at least one precursor of oxidative para dye and at least one heterocyclic coupling agent, having the general formula (1) of the formula sheet, wherein OH occupies positions 6 or 7 of the aromatic core and a hydrogen atom represents a C 1 -C alkyl residue; R 1 and are the same or different and a hydrogen atom, a C 1 -C 8 alkyl radical, a carboxyl radical or a C 1 -C 12 alkyl. mean alkoxycarbonyl residue; as well as their salts.
Van de verbindingen met de formule (1), verdienen de verbindingen waarin de alkylrest methyl, ethyl, de alkoxycarbonylrest methoxy of ethoxycarbonylrest betekent in het bijzonder de voorkeur.Of the compounds of formula (1), the compounds wherein the alkyl radical represents methyl, ethyl, the alkoxycarbonyl radical represents methoxy or ethoxycarbonyl radical is particularly preferred.
Van die verbindingen worden genoemd 6-hydroxyindool, 6-hydroxy-3~ methoxycarbonylindool, 6-hydroxy-l-methyl-3-methoxycarbonylindool, 6-hydroxy-l-methyl-2,3~dimethoxycarbonylindool, 6-hydroxy-l, 2-dimethyl- indool, 6-hydroxy-2-methylindool, 6-hydroxy-2-carboxyindool, 6-hydroxy- 2,3-dimethylindool, 6-hydroxy-3~carboxyindool, 6-hydroxy-3_ethoxycarbo-nylindool, 6-hydroxy-2-ethoxycarbonylindool, 6-hydroxy-3-methylindool, 6-hydroxy-l-methylindool, 7“hydroxyindool, 7-hydroxy~3-methylindool. Van die verbindingen zijn 6-hydroxy-l-methylindool en 7"hydroxy-3_methyl-indool nieuw en hun syntheses worden in het hierna volgende beschreven.Among those compounds are mentioned 6-hydroxyindole, 6-hydroxy-3-methoxycarbonylindole, 6-hydroxy-1-methyl-3-methoxycarbonylindole, 6-hydroxy-1-methyl-2,3-dimethoxycarbonylindole, 6-hydroxy-1,2 -dimethylindole, 6-hydroxy-2-methylindole, 6-hydroxy-2-carboxyindole, 6-hydroxy-2,3-dimethylindole, 6-hydroxy-3-carboxyindole, 6-hydroxy-3-ethoxycarbonylindole, 6-hydroxy -2-ethoxycarbonylindole, 6-hydroxy-3-methylindole, 6-hydroxy-1-methylindole, 7 "hydroxyindole, 7-hydroxy-3-methylindole. Of those compounds, 6-hydroxy-1-methylindole and 7 "hydroxy-3-methyl-indole are new and their syntheses are described below.
De voorlopers van kleurstoffen van het type para zijn verbindingen die niet op zichzelf kleurstoffen zijn, maar die een kleur vormen door een oxidatieve omzetting, hetzij op zichzelf, hetzij bij aanwezigheid van een koppelingsmiddel of modificeermiddel.The precursors of dyes of the type para are compounds which are not dyes per se, but which form a color by an oxidative conversion, either by themselves or in the presence of a coupling agent or modifying agent.
Deze verbindingen bevatten functionele groepen, in het bijzonder amino of hydroxylgroepen, op de para-plaats ten opzichte van elkaar.These compounds contain functional groups, especially amino or hydroxyl groups, in the para position relative to each other.
Deze voorlopers van kleurmiddelen van het type para zijn in het bijzonder gekozen uit de parafenyleendiamines, de para-aminofenolen, de heterocyclische para-voorlopers, zoals 2,5~diaminopyridine, 2-hydroxy-5_ aminopyridine, en tetra-aminopyrimidine.These para colorant precursors are selected in particular from the paraphenylenediamines, the para-aminophenols, the heterocyclic para precursors, such as 2,5-diaminopyridine, 2-hydroxy-5-aminopyridine, and tetra-aminopyrimidine.
Als parafenyleendiamines, kan men in het bijzonder noemen de verbindingen met de formule (2), waarin Rty, R^ en Rg gelijk of verschillend zijn en een waterstofatoom of halogeenatoom, een alkylrest met 1 tot 4 koolstofatomen, een alkoxyrest met 1 tot k koolstofatomen betekenen, Bq en Rg gelijk of verschillend zijn, en een waterstofatoom, een alkylrest, een hydroxyalkylrest, een alkoxyalkylrest, een carbamyl-alkylrest, een mesylaminoalkylrest, een acetylaminoalkylrest, een ureïdoalkylrest, een carbethoxyaminoalkylrest, een piperidinoalkylrest, een morfolinoalkylrest voorstellen. Deze alkyl- of alkoxygroepen bezitten 1 tot 4 koolstof atomen, ofwel Ry en Rg vormen samen met het stikstofatoom waaraan zij gebonden zijn een heterocyclische piperidino-of morfolinorest onder voorbehoud dat R/j of Rg een waterstofatoom voorstellen, terwijl Ry en Rg niet een waterstofatoom voorstellen, evenals de zouten van deze verbindingen.As paraphenylenediamines, one can particularly mention the compounds of formula (2), wherein Rty, R 1 and R 5 are the same or different and a hydrogen atom or halogen atom, an alkyl radical with 1 to 4 carbon atoms, an alkoxy radical with 1 to k carbon atoms mean, Bq and Rg are the same or different, and represent a hydrogen atom, an alkyl radical, a hydroxyalkyl radical, an alkoxyalkyl radical, a carbamyl-alkyl radical, a mesylaminoalkyl radical, an acetylaminoalkyl radical, an ureaalkyl radical, a carbethoxyaminoalkyl radical, a piperidinoalkyl radical, a morpholinoalkyl radical. These alkyl or alkoxy groups have 1 to 4 carbon atoms, or Ry and Rg together with the nitrogen atom to which they are attached form a heterocyclic piperidino or morpholino radical provided that R / j or Rg represent a hydrogen atom, while Ry and Rg do not represent a hydrogen atom as well as the salts of these compounds.
Van de verbindingen met de formule (2) kan men in het bijzonder noemen p-fenyleendiamine, p-toluyleendiamine, methoxyparafenyleendiami-ne, chloorparaf enyleendiamine, 2,6-dimethyl-p-fenyleendiamine, 2,5” dimethylparafenyleendiamine, 2-methyl-5-methoxyparafenyleendiamine, 2,6-dimethyl-5-methoxyparaf enyleendiamine, N, N-dimethylparaf enyleendiamine, 3- methyl-4-amino-N,N-diethylaniline, N, N-di (β-hydroxyethyl)parafenyleendiamine, 3"methyl-4-amino-N,N-di-(β-hydroxyethyl)aniline, 3-chloor-4-amino-N,N-di-(β-hydroxyethyl)aniline, 4-amino-N,N-(ethylcarbamyl-methyl)aniline, 3”methyl-4-amino-N,N-(ethylcarbamylmethyl)aniline, 4-amino-N,N-(ethyl-p-piperidino-ethyl)aniline, 3”methyl-4-amino-N,N-(ethyl-p-piperidino-ethyl) aniline, 4-amino-N,N-(ethyl-fJ-morfolino-ethyl)aniline, 3-“ethyl-4-araino-N,N-(ethyl-p-morfolino-ethyl)aniline, 4-amino-Ν,Ν- (ethyl-^-acetylamino-ethyl) aniline, 4-amino-N- (β-methoxy-ethyl) aniline, 3-®ethyl-4-amino-N,N- (ethyl-β-ace tylamino-ethyl) aniline, 4- amino-N,N-(ethyl-p-mesylamino-ethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-β-mesylamino-ethyl)aniline, 4-amino-N,N-(ethyl-p-sulfo-ethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-p-sulfo-ethyl)aniline, N—[(4 * — amino)fenyl]morfoline, N-[(4'-amino)fenyl]piperidine. Deze voorlopers van de oxidatiekleurstoffen van het type para kunnen worden opgenomen in de verfpreparaten, hetzij in de vorm van de vrije base, hetzij in de vorm van zouten, zoals in de vorm van chloorhydraat, broomhydraat of sulfaat.Among the compounds of formula (2), particular mention may be made of p-phenylenediamine, p-toluylenediamine, methoxy-paraphenylenediamine, chloroparaphenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,5 ”dimethyl paraphenylenediamine, 2-methyl- 5-methoxy-paraphenylenediamine, 2,6-dimethyl-5-methoxy-paraphenylenediamine, N, N-dimethylparaphenylenediamine, 3-methyl-4-amino-N, N-diethylaniline, N, N-di (β-hydroxyethyl) paraphenylenediamine, 3 " methyl-4-amino-N, N-di- (β-hydroxyethyl) aniline, 3-chloro-4-amino-N, N-di- (β-hydroxyethyl) aniline, 4-amino-N, N- (ethylcarbamyl -methyl) aniline, 3 "methyl-4-amino-N, N- (ethylcarbamylmethyl) aniline, 4-amino-N, N- (ethyl-p-piperidinoethyl) aniline, 3" methyl-4-amino-N , N- (ethyl-p-piperidino-ethyl) aniline, 4-amino-N, N- (ethyl-F-morpholino-ethyl) aniline, 3- “ethyl-4-araino-N, N- (ethyl-p -morpholinoethyl) aniline, 4-amino-Ν, Ν- (ethyl - ^ - acetylaminoethyl) aniline, 4-amino-N- (β-methoxy-ethyl) aniline, 3-®ethyl-4-amino- N, N- (ethyl-β-ace tylamino-ethyl) aniline, 4- amino-N, N- (ethyl-p-mesylamino-ethyl) aniline, 3-methyl-4-amino-N, N- (ethyl-β-mesylamino-ethyl) aniline, 4-amino-N, N- (ethyl -p-sulfo-ethyl) aniline, 3-methyl-4-amino-N, N- (ethyl-p-sulfoethyl) aniline, N - [(4 * - amino) phenyl] morpholine, N - [(4 -amino) phenyl] piperidine. These para oxidation dye precursors can be incorporated into the paint compositions, either in the form of the free base or in the form of salts, such as in the form of chlorohydrate, bromohydrate or sulfate.
Van de p-aminofenolen, worden genoemd p-aminofenol, 2-methyl-4-aminofenol, 3“methyl-4-aminofenol, 2-chloor-4-aminofenol, 3-chloor-4-aminofenol, 2,6-dimethyl-4-aminofenol, 3,5“dimethyl-4-aminofenol, 2,3_ dimethyl-4-aminofenol, 2,5-dimethyl-4-aminofenol, 2-hydroxymethyl-4-aminofenol, 2- (β-hydroxyethyl) -4-aminofenol, 2-methoxy-4-aminofenol, 3-methoxy-4-aminofenol.Of the p-aminophenols, are mentioned p-aminophenol, 2-methyl-4-aminophenol, 3 "methyl-4-aminophenol, 2-chloro-4-aminophenol, 3-chloro-4-aminophenol, 2,6-dimethyl- 4-aminophenol, 3,5 "dimethyl-4-aminophenol, 2,3_ dimethyl-4-aminophenol, 2,5-dimethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2- (β-hydroxyethyl) -4 aminophenol, 2-methoxy-4-aminophenol, 3-methoxy-4-aminophenol.
De verfpreparaten volgens de uitvinding kunnen bovendien voorlopers van oxidatiekleurstoffen van het type ortho bevatten, zoals de örthoaminofenolen, zoals l-amino-2-hydroxybenzeen, 6-methyl-l-hydroxy-2-aminobenzeen, 4-methyl-l-amino-2-hydroxybenzeen en orthofenyleendiami-nes, de orthodifenolen.The paint compositions according to the invention may additionally contain precursors of ortho oxidation dyes, such as the orthoaminophenols, such as 1-amino-2-hydroxybenzene, 6-methyl-1-hydroxy-2-aminobenzene, 4-methyl-1-amino-2 -hydroxybenzene and orthophenylenediamines, the orthodiphenols.
De verfpreparaten kunnen naast heterocyclische koppelingsmiddelen met de algemene formule (1) die hierboven is aangegeven, bevatten andere op zichzelf bekende koppelingsmiddelen, zoals de metadifenolen, de meta-aminofenolen, de metafenyleendiamines, de meta-acylaminof enolen, de meta-ureïdofenolen, de metacarbalkoxyaminofenolen, a-naftol, koppelingsmiddelen die een actieve methyleengroep bevatten zoals de β-ketonverbin-dingen en de pyrazolonen.The paint preparations may contain, in addition to heterocyclic coupling agents of the general formula (1) indicated above, other coupling agents known per se, such as the metadiphenols, the meta-aminophenols, the meta-phenylenediamines, the meta-acylamino-phenols, the meta-urea-phenophenols, the meta-carboxoxy-aminophenols α-naphthol, coupling agents containing an active methylene group such as the β-ketone compounds and the pyrazolones.
In het bijzonder worden als voorbeeld genoemd 2,4-dihydroxyfenoxyethanol, 2,4-dihydroxyanisool, meta-aminofenol, de monomethylether van resorcinol, 2-methyl-5-aminofenol, 2-methyl-5~N-(β-hydroxyethyl)amino-fenol, 2-methyl-5~N- (β-mesylamino-ethyl) aminof enol, 2,6-dimethyl-3" aminofenol, 6-hydroxybenzomorfoline, 2,4-diaminoanisool, 2,4-diamino-fenoxyethanol, 6-aminobenzomorf oline, [2-N- (β-hydroxyethyl) amino-4-amino]fenoxyethanol, 2-amino-4-N-(β-hydroxyethyl)aminoanisool, (2,4-diamino)fenyl-β,/-dihydroxypropylether, 2,4-diaminofenoxyethylamine en hun zouten.Particularly mentioned are exemplary 2,4-dihydroxyphenoxyethanol, 2,4-dihydroxyanisole, meta-aminophenol, the monomethyl ether of resorcinol, 2-methyl-5-aminophenol, 2-methyl-5 ~ N- (β-hydroxyethyl) amino -phenol, 2-methyl-5-N- (β-mesylaminoethyl) aminophenol, 2,6-dimethyl-3 "aminophenol, 6-hydroxybenzomorpholine, 2,4-diaminoanisole, 2,4-diamino-phenoxyethanol, 6 -aminobenzomorph oline, [2-N- (β-hydroxyethyl) amino-4-amino] phenoxyethanol, 2-amino-4-N- (β-hydroxyethyl) aminoanisole, (2,4-diamino) phenyl-β, / - dihydroxypropyl ether, 2,4-diaminophenoxyethylamine and their salts.
Men kan later aan deze preparaten toevoegen, zoals volgens de stand van de techniek bekend is, vooral met het oog op het nuanceren of verrijken van de glans die bereikt is met de voorlopers van de oxidatie-ve kleurstoffen, directe kleurstoffen zoals azokleurstoffen, antrachi-nonkleurstoffen of genitreerde derivaten van de benzeenreeks.These compositions may be added later, as is known in the art, in particular with a view to nuancing or enriching the gloss achieved with the precursors of the oxidative dyes, direct dyes such as azo dyes, anthrachi. non-dyes or nitrated derivatives of the benzene series.
Het complex van voorlopers van oxidatieve kleurstoffen van het type para alsmede van de toegepaste koppelingsmiddelen in de verfpreparaten volgens de uitvinding, maakt bij voorkeur 0,3 tot 7 gew.%, betrokken op het gewicht van het gehele preparaat uit. De concentratie van de verbindingen (1) kan variëren van 0,05 tot 3.5 gew.# betrokken op het totaal van het preparaat.The complex of oxidative colorant precursors of the type para as well as of the coupling agents used in the paint compositions according to the invention preferably represents 0.3 to 7% by weight, based on the weight of the whole composition. The concentration of the compounds (1) can range from 0.05 to 3.5% by weight based on the total of the preparation.
Het aanvaardbare oplosmiddelmilieu is in het algemeen waterrijk en de pH daarvan kan variëren van 8 tot 11 en is bij voorkeur gelegen tussen 9 en 11.The acceptable solvent medium is generally water-rich and its pH can range from 8 to 11 and is preferably between 9 and 11.
De pH wordt op de gewenste waarde ingesteld met behulp van een alkaliserend middel zoals ammonia, alkalimetaalcarbonaten, alkanolamines zoals mono-, di- of triethanolamine.The pH is adjusted to the desired value using an alkalizing agent such as ammonia, alkali metal carbonates, alkanolamines such as mono-, di- or triethanolamine.
De verfpreparaten volgens de uitvinding bevatten in hun voorkeursuitvoering ook anionogene, kationogene, non-ionogene, amfotere opper-vlakte-actieve verbindingen of hun mengsels. Van deze oppervlakte-actieve middelen worden genoemd alkylbenzeensulfonaten, alkylnaftaleen-sulfonaten, de sulfaten, ethersulfaten en vetalcoholsulfonaten, kwatemaire ammoniumzouten zoals het bromide van trimethylcetylammonium, het bromide van cetylpyridine, ethanolamiden van vetzuren, die eventueel oxyethyleengroepen bevatten, de zuren, de alcoholen of de polyoxyethy-leengroepen bevattende aminen, polyglycerolgroepen bevattende alcoholen, polyoxyethyleengroepen of polyglycerolgroepen bevattende alkylfenolen, evenals de polyoxyethyleengroepen bevattende alkylsulfaten.In their preferred embodiment, the paint compositions of the invention also contain anionic, cationic, nonionic, amphoteric surfactants or their mixtures. Among these surfactants are mentioned alkylbenzene sulfonates, alkylnaphthalene sulfonates, the sulfates, ether sulfates and fatty alcohol sulfonates, quaternary ammonium salts such as the bromide of trimethylcetylammonium, the bromide of cetylpyridine, ethanolamides of fatty acids, optionally containing oxyethylene groups, the acids, the alkenes, the acids polyoxyethylene groups containing amines, polyglycerol groups containing alcohols, polyoxyethylene groups or polyglycerol groups containing alkyl phenols, as well as the polyoxyethylene groups containing alkyl sulfates.
Deze oppervlakte-actieve middelen zijn aanwezig in de preparaten volgens de uitvinding in hoeveelheden van 0,5 tot 55 gew.#, en bij voorkeur in hoeveelheden van 2 tot 50 gew.# betrokken op het gewicht van het gehele preparaat.These surfactants are present in the compositions of the invention in amounts from 0.5 to 55% by weight, and preferably in amounts from 2 to 50% by weight, based on the weight of the whole composition.
Deze preparaten kunnen ook organische oplosmiddelen bevatten om de verbindingen die niet voldoende oplosbaar zouden zijn in water te solubiliseren. Tot de oplosmiddelen die gebruikt kunnen worden behoren bijvoorbeeld de C^-C^ alkanolen, zoals ethanol en isopropanol, glycerol, de glycolen of ethers van glycol, 2-butoxyethanol, ethyleenglycol, propyleenglycol, de mono-ethylether en de monomethylether van diethy-leenglycol, evenals de aromatische alcoholen zoals benzylalcohol of fenoxyethanol, analoge produkten of hun mengsels.These preparations may also contain organic solvents to solubilize the compounds that would not be sufficiently soluble in water. Solvents which can be used include, for example, the C 1 -C 6 alkanols, such as ethanol and isopropanol, glycerol, the glycols or ethers of glycol, 2-butoxyethanol, ethylene glycol, propylene glycol, the monoethyl ether and the monomethyl ether of diethylene glycol as well as the aromatic alcohols such as benzyl alcohol or phenoxyethanol, analogous products or their mixtures.
De oplosmiddelen zijn bij voorkeur aanwezig in een hoeveelheid van 1 tot 40 gew.#, in het bijzonder van 5 tot 30 gew.# betrokken op het totale gewicht van het preparaat.The solvents are preferably present in an amount of from 1 to 40% by weight, in particular from 5 to 30% by weight, based on the total weight of the preparation.
De verdikkingsmiddelen die men aan de preparaten volgens de uitvinding kan toevoegen kunnen worden gekozen in het bijzonder uit natriumalginaat, arabische gom, cellulosederivaten zoals methylcellulo-se, hydroxyethylcellulose, hydroxypropylcellulose, hydroxymethylcellulo-se, carboxymethylcellulose, de polymeren van acrylzuur, xanthaangom. Men kan ook anorganische verdikkingsmiddelen gebruiken, zoals bentoniet. Deze verdikkingsmiddelen zijn bij voorkeur aanwezig in hoeveelheden van 0,1 tot 5 gew.# en in het bijzonder in een hoeveelheid van 0,2 tot 3 gew.# betrokken op het totale gewicht van het preparaat.The thickeners which can be added to the compositions of the invention can be selected in particular from sodium alginate, gum arabic, cellulose derivatives such as methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxymethyl cellulose, carboxymethyl cellulose, the polymers of acrylic acid, xanthan gum. Inorganic thickeners such as bentonite can also be used. These thickeners are preferably present in amounts of 0.1 to 5 wt.%, And in particular in an amount of 0.2 to 3 wt.%, Based on the total weight of the preparation.
De antioxiderende middelen die in de preparaten volgens de uitvinding aanwezig kunnen zijn worden in het bijzonder gekozen uit natriumsulfiet, thioglycolzuur, natriumbisulfiet, ascorbinezuur en hydrochinon. Deze antioxidanten zijn in het preparaat in hoeveelheden van 0,05 tot 1,5 gew.# betrokken op het totale preparaat aanwezig.The antioxidants which may be present in the compositions of the invention are selected in particular from sodium sulfite, thioglycolic acid, sodium bisulfite, ascorbic acid and hydroquinone. These antioxidants are present in the composition in amounts from 0.05 to 1.5% by weight based on the total composition.
Deze preparaten kunnen ook andere aanvaardbare kosmetische toevoegsels bevatten, zoals bijvoorbeeld penetreermiddelen, sequestreer-middelen, buffers en parfums.These formulations may also contain other acceptable cosmetic additives, such as, for example, penetrants, sequestrants, buffers and perfumes.
De preparaten volgens de uitvinding kunnen in verschillende vormen aanwezig zijn, zoals in de vorm van vloeistoffen, cremes, gelen of onder andere vorm die geschikt is voor het uitvoeren van een verving van keratine bevattende draden en in het bijzonder van menselijk haar. Deze preparaten kunnen ook worden geconditioneerd in aerosolflacons bij aanwezigheid van een drijfmiddel.The compositions of the invention may be in various forms, such as in the form of liquids, creams, gels or any other form suitable for dyeing keratin-containing threads and in particular human hair. These formulations can also be conditioned in aerosol bottles in the presence of a propellant.
De verfpreparaten volgens de uitvinding die een voorloper van oxidatieve kleurstof van het type para bevatten en een koppelingsmiddel met de formule (1), worden toegepast bij het verven van keratine bevattende draden en in het bijzonder menselijk haar, volgens een werkwijze waarbij de ontwikkeling plaatsvindt door een oxidatiemiddel.The dyeing compositions according to the invention containing a para oxidative dye precursor and a coupling agent of the formula (1) are used in the dyeing of keratin-containing threads and in particular human hair, according to a process in which development takes place by an oxidizing agent.
Volgens deze werkwijze mengt men op het moment van het gebruik het hierboven beschreven verfpreparaat met een oxiderende oplossing in een hoeveelheid die voldoende is om de kleur te kunnen ontwikkelen, vervolgens brengt men het verkregen mengsel aan op de keratine bevattende draden en in het bijzonder op menselijk haar.According to this method, at the time of use, the paint composition described above is mixed with an oxidizing solution in an amount sufficient to allow the color to develop, then the resulting mixture is applied to the keratin-containing threads and in particular to human her.
De oxiderende oplossing bevat oxidatiemiddelen, zoals met zuurstof verrijkt water, ureumperoxide of perzouten, zoals ammoniumpersulfaat♦ Men gebruikt bij voorkeur een oplossing met zuurstofrijk water in een hoeveelheid van 20 volumes.The oxidizing solution contains oxidizing agents, such as oxygen-enriched water, urea peroxide or persalts, such as ammonium persulfate. A solution with oxygen-rich water is preferably used in an amount of 20 volumes.
Het verkregen mengsel wordt op de haren aangebracht en men laat dit inwerken gedurende 10 tot 40 minuten, bij voorkeur 15 tot 30 minuten, waarna men de haren spoelt, deze wast of shamponeert, spoelt opnieuw en droogt.The resulting mixture is applied to the hair and allowed to act for 10 to 40 minutes, preferably 15 to 30 minutes, after which the hair is rinsed, washed or shampooed, rinsed again and dried.
Het heterocyclische koppelingsmiddel met de formule (1) dat hierboven gedefinieerd is, kan ook toegepast worden bij een werkwijze die in meerdere trappen wordt uitgevoerd, waarbij één trap omvat het aanbrengen van de voorloper van de oxidatieve para-kleurstof door middel van een hierboven gedefinieerd preparaat, en in een andere trap het aanbrengen van het koppelingsmiddel met de formule (1).The heterocyclic coupling agent of the formula (1) defined above can also be used in a multistage process, wherein one step involves applying the oxidative para-dye precursor by means of a composition defined above , and in another step applying the coupling agent of the formula (1).
Het oxidatiemiddel kan worden toegevoegd juist vóór het aanbrengen van het preparaat in de tweede trap ofwel worden toegevoegd op de keratine bevattende draden zelf in een derde trap, waarbij de inwerk-periode en het drogen of wassen identiek zijn.The oxidizing agent can be added just before the preparation of the second stage preparation or added to the keratin-containing threads themselves in a third stage, with the exposure period and drying or washing being identical.
De onderstaande voorbeelden zijn bestemd om de uitvinding toe te lichten zonder deze evenwel te beperken.The examples below are intended to illustrate the invention without, however, limiting it.
Toepassingsvoorbeeld 1Application example 1
Men bereidt het volgende verfmengsel: - 6-hydroxyindool 0,33 g - p-fenyleendiamine 0,27 g - oleïne-alcohol die 2 mol glycerol bevat 4,5 g - oleïne-alcohol die 4 mol glycerol bevat 4,5 g - ΕΊΉ0ΜΕΕΝ 0 12 - Société ARM00N HESS CHEMICAL Ltd (geoxyethyleneerde oleylamine met 12 mol ethyleenoxide) 4,5 gThe following paint mixture is prepared: - 6-hydroxyindole 0.33 g - p-phenylenediamine 0.27 g - oleic alcohol containing 2 moles glycerol 4.5 g - oleic alcohol containing 4 moles glycerol 4.5 g - ΕΊΉ0ΜΕΕΝ 0 12 - Société ARM00N HESS CHEMICAL Ltd (oxyethylenated oleylamine with 12 moles ethylene oxide) 4.5 g
- COMPERLAN KD - Société HENKEL- COMPERLAN KD - Société HENKEL
(diethanolamide van kopra) 9.0 g - propyleenglycol 4,0 g - 2-butoxyethanol 8,0 g - ethanol 96° 6,0 g(copra diethanolamide) 9.0 g - propylene glycol 4.0 g - 2-butoxyethanol 8.0 g - ethanol 96 ° 6.0 g
- MASQU0L DTPA - Société PR0TEX- MASQU0L DTPA - Société PR0TEX
(pentanatriumzout van diethyleentriaminepenta-azijnzuur) 2,0 g - hydrochinon 0,15 g - oplossing van natriumbisulfiet tot 35°Be 1,3 g - ammoniak 22“Be 10,0 g - water aanvullen tot 100,0 g - PH = 10,5(pentasodium salt of diethylene triamine pentaacetic acid) 2.0 g - hydroquinone 0.15 g - sodium bisulfite solution up to 35 ° Be 1.3 g - ammonia 22 “Be 10.0 g - make up to 100.0 g - PH = 10 , 5
Op het moment van het gebruik voegt men 100 g water, verrijkt met 20 volumes zuurstof, toe. Het op natuurlijk grijze haren met een witheid van 90$ aangebrachte mengsel verschaft na 20 minuten bij 34°C, shamponeren en spoelen een bruine middelmatig goudblonde kleur.At the time of use, 100 g of water, enriched with 20 volumes of oxygen, are added. The mixture applied to natural gray hairs with a whiteness of 90% provides a medium brown golden color after 20 minutes at 34 ° C, shampooing and rinsing.
Toepassingsvoorbeeld 2Application example 2
Men bereidt het volgende verfmengsel: - 6-hydroxyindool 0,33 g - p-aminofenol 0,27 g - oleïne-alcohol die 2 mol glycerol bevat 4,5 g - oleïne-alcohol die 4 mol glycerol bevat 4,5 g - ETHOMEEN 0 12 - Société ARM00N HESS CHEMICAL Ltd (geoxyethyleneerde oleylamine met 12 mol ethyleenoxide) 4,5 gThe following paint mixture is prepared: - 6-hydroxyindole 0.33 g - p-aminophenol 0.27 g - oleic alcohol containing 2 moles glycerol 4.5 g - oleic alcohol containing 4 moles glycerol 4.5 g - ETHOMENE 0 12 - Société ARM00N HESS CHEMICAL Ltd (oxyethylenated oleylamine with 12 moles ethylene oxide) 4.5 g
- COMPERLAN KD - Société HENKEL- COMPERLAN KD - Société HENKEL
(diethanolamide van kopra) 9,0 g - propyleenglycol 4,0 g - 2-butoxyethanol 8,0 g - ethanol 96° 6,0 g(copra diethanolamide) 9.0 g - propylene glycol 4.0 g - 2-butoxyethanol 8.0 g - ethanol 96 ° 6.0 g
- MASQU0L DTPA - Société PR0TEX- MASQU0L DTPA - Société PR0TEX
(pentanatriumzout van diethyleentriaminepenta-azijnzuur) 2,0 g - hydrochinon 0,15 g - oplossing van natriumbisulfiet tot 35°Be 1,3 g - ammoniak 22°Be 10,0 g - water aanvullen tot 100,0 g - pH = 10,5(pentasodium salt of diethylenetriamine pentaacetic acid) 2.0 g - hydroquinone 0.15 g - solution of sodium bisulfite up to 35 ° Be 1.3 g - ammonia 22 ° Be 10.0 g - make up water to 100.0 g - pH = 10 , 5
Op het moment van het gebruik voegt men 100 g met 20 volumes zuurstof verrijkt water toe. Het op ontkleurde haren aangebrachte mengsel verschaft na 20 minuten bij 34°C, shamponeren en spoelen, een beige goudblonde kleur.At the time of use, 100 g of water enriched with 20 volumes of oxygen are added. After 20 minutes at 34 ° C, shampooing and rinsing, the mixture applied to decolorized hair provides a beige golden blonde color.
Toepassingsvoorbeeld 3Application example 3
Men bereidt het volgende verfmengsel: - 6-hydroxy-l-methylindool 0,73 g - dichloorhydraat van 4-bis-(β-hydroxyethyl)aminoaniline 1,34 gThe following paint mixture is prepared: - 6-hydroxy-1-methylindole 0.73 g - dichlorohydrate of 4-bis- (β-hydroxyethyl) aminoaniline 1.34 g
- CELLOSIZE WP 03 - Société UNION CARBIDE- CELLOSIZE WP 03 - Société UNION CARBIDE
(hydroxyethylcellulose) 2,0 g - ammoniumlaurylsulfaat 5,0 g - 2-butoxyethanol 15,0 g - alcohol 96 5,0 g(hydroxyethyl cellulose) 2.0 g - ammonium lauryl sulfate 5.0 g - 2-butoxyethanol 15.0 g - alcohol 96 5.0 g
- MASQU0L DTPA - Société PR0TEX- MASQU0L DTPA - Société PR0TEX
(pentanatriumzout van diethyleentriaminepenta-azijnzuur) 2,0 g - water aanvullen tot 100,0 g - pH = 10,5(pentasodium salt of diethylene triamine pentaacetic acid) 2.0 g - make up water to 100.0 g - pH = 10.5
Op het moment van het gebruik voegt men 100 g water dat verrijkt is met 20 volumes zuurstof toe. Het op natuurlijk grijze haren met een witheid van 90¾ aangebrachte mengsel verschaft na 20 minuten bij 3^°C na shamponeren en spoelen, een grijs-purperen kleur.At the time of use, 100 g of water enriched with 20 volumes of oxygen are added. The mixture applied to natural gray hairs with a whiteness of 90¾ gives a gray-purple color after 20 minutes at 3 ° C after shampooing and rinsing.
Toepassingsvoorbeeld 4Application example 4
Men bereidt het volgende verfmengsel: - 6-hydroxy-l-methylindool 0,29 g - parafenyleendiamine 0,22 gThe following paint mixture is prepared: - 6-hydroxy-1-methylindole 0.29 g - paraphenylenediamine 0.22 g
-octyldodecanol verkocht onder de aanduiding EUTAN0L Goctyl dodecanol sold under the designation EUTAN0L G
door de Société HENKEL 8,0 g - oliezuur 20,0 g - mono-ethanolamine van laurylethersulfaat verkocht onder de aanduiding SIP0N LM 35 door de Société HENKEL 3.0 g - ethylalcohol 10,0 g - benzylalcohol 10,0 gby the Société HENKEL 8.0 g - oleic acid 20.0 g - monoethanolamine of lauryl ether sulfate sold under the designation SIP0N LM 35 by the Société HENKEL 3.0 g - ethyl alcohol 10.0 g - benzyl alcohol 10.0 g
- cetylstearylalcohol geoxyethyleneerd met 33 mol ethyleenoxide verkocht onder de aanduiding SIMULS0L GS- cetylstearyl alcohol oxyethylenated with 33 moles of ethylene oxide sold under the designation SIMULS0L GS
door de Société SEPPIC 2,4 g - ethyleendiaminetetra-azijnzuur 0,2 g - kationogeen polymeer bestaande uit zich herhalende eenheden met de formule 3 van het formuleblad 2,2 g - mono-ethanolamine 7.5 g - diethanolamide van linolzuur verkocht onder de aanduiding COMPERLAN F door de Société HENKEL 8,0 g - ammoniak 20% 10,2 g - 35¾'s oplossing in water van natriummetabisulfiet 1,3 g - hydrochinon 0,15 g - l-fenyl-3-methyl-5-pyrazolon 0,2 g - gedemineraliseerd water aanvullen tot 100,0 gby the Société SEPPIC 2.4 g - ethylenediaminetetraacetic acid 0.2 g - cationic polymer consisting of repeating units of the formula 3 of the formula sheet 2.2 g - monoethanolamine 7.5 g - diethanolamide of linoleic acid sold under the designation COMPERLAN F by the Société HENKEL 8.0 g - ammonia 20% 10.2 g - 35's aqueous solution of sodium metabisulfite 1.3 g - hydroquinone 0.15 g - 1-phenyl-3-methyl-5-pyrazolone 0.2 g - make up to 100.0 g demineralised water
Het preparaat wordt gemengd op het moment van het gebruik, gewicht op gewicht, met water dat met 20 volumes zuurstof verrijkt is en waarvan de pH gelijk is aan 3·The preparation is mixed at the time of use, weight by weight, with water enriched with 20 volumes of oxygen, the pH of which is equal to 3 ·
Het aldus verkregen mengsel wordt gedurende 30 minuten aangebracht op grijze haren met een witheid van 90¾. daarna gespoeld, gewassen, opnieuw gespoeld en gedroogd.The mixture thus obtained is applied to gray hairs with a whiteness of 90¾ for 30 minutes. then rinsed, washed, rinsed again and dried.
De verkregen kleuring is koperachtig beigeblond.The resulting coloring is coppery beige-blond.
Toepassingsvoorbeeld 5Application example 5
Men bereidt het volgende verfmengsel: - 6-hydroxy-2-ethoxycarbonylindool 0,4l g - parafenyleendiamine 0,22 gThe following paint mixture is prepared: - 6-hydroxy-2-ethoxycarbonylindole 0.4 l g - paraphenylenediamine 0.22 g
- octyldodecanol verkocht onder de aanduiding EUTANOL Goctyldodecanol sold under the designation EUTANOL G
door de Sociétê HENKEL 8,0 g - oliezuur 20,0 g - mono-ethanolamine van laurylethersulfaat verkocht onder de aanduiding SIPON LM 35 door de Société HENKEL 3»0 g - ethylalcohol 10,0 g - benzylalcohol 10,0 gby the Sociétê HENKEL 8.0 g - oleic acid 20.0 g - monoethanolamine of lauryl ether sulfate sold under the designation SIPON LM 35 by the Société HENKEL 3 »0 g - ethyl alcohol 10.0 g - benzyl alcohol 10.0 g
- cetylstearylalcohol geoxyethyleneerd met 33 mol ethyleenoxide verkocht onder de aanduiding SIMULS0L GS- cetylstearyl alcohol oxyethylenated with 33 moles of ethylene oxide sold under the designation SIMULS0L GS
door de Sociétê SEPPIC 2,k g - ethyleendiaminetetra-azijnzuur 0,2 g - kationogeen polymeer bestaande uit zich herhalende eenheden met de formule 3 van het formuleblad 2,2 g - mono-ethanolamine 7,5 g - diethanolamide van linolzuur verkocht onder de aanduiding COMPERLAN F door de Société HENKEL 8,0 g - ammoniak 20% 10,2 g - 35%'s oplossing in water van natriummetabisulfiet 1,3 g - hydrochinon 0,15 g - 1-fenyl-3-methyl-5-pyrazolon 0,2 g - gedemineraliseerd water aanvullen tot 100,0 gby the Sociétê SEPPIC 2, kg - ethylenediaminetetraacetic acid 0.2 g - cationic polymer consisting of repeating units of the formula 3 of the formula sheet 2.2 g - monoethanolamine 7.5 g - diethanolamide of linoleic acid sold under the designation COMPERLAN F by Société HENKEL 8.0 g - ammonia 20% 10.2 g - 35% aqueous solution of sodium metabisulfite 1.3 g - hydroquinone 0.15 g - 1-phenyl-3-methyl-5-pyrazolone 0.2 g - make up demineralized water to 100.0 g
Het preparaat wordt gemengd op het moment van het gebruik, gewicht op gewicht, met water dat met 20 volumes zuurstof verrijkt is en waarvan de pH gelijk is aan 3.The preparation is mixed at the time of use, weight by weight, with water enriched with 20 volumes of oxygen, the pH of which is equal to 3.
Het aldus verkregen mengsel wordt gedurende 30 minuten aangebracht op grijs haar met een witheid van $0%, daarna gespoeld, gewassen, opnieuw gespoeld en gedroogd.The mixture thus obtained is applied to gray hair of $ 0% whiteness for 30 minutes, then rinsed, washed, rinsed again and dried.
De verkregen kleur is blondbeige askleurig.The resulting color is blond beige ash colored.
Toepassingsvoorbeeld 6Application example 6
Men bereidt het volgende verfmengsel: - 6-hydroxy-2-carboxyindool 0,35 g - parafenyleendiamine 0,22 gThe following paint mixture is prepared: - 6-hydroxy-2-carboxyindole 0.35 g - paraphenylenediamine 0.22 g
- octyldodecanol verkocht onder de aanduiding EUTANOL Goctyldodecanol sold under the designation EUTANOL G
door de Société HENKEL 8,0 g - oliezuur 20,0 g - mono-ethanolamine van laurylethersulfaat verkocht onder de aanduiding SIP0N LM 35 door de Société HENKEL 3,0 g - ethylalcohol 10,0 g - benzylalcohol 10,0 gby the Société HENKEL 8.0 g - oleic acid 20.0 g - monoethanolamine of lauryl ether sulfate sold under the designation SIP0N LM 35 by the Société HENKEL 3.0 g - ethyl alcohol 10.0 g - benzyl alcohol 10.0 g
- cetylstearylalcohol geoxyethyleneerd met 33 mol ethyleenoxide verkocht onder de aanduiding SIMULS0L GS- cetylstearyl alcohol oxyethylenated with 33 moles of ethylene oxide sold under the designation SIMULS0L GS
door de Société SEPPIC 2,4 g - ethyleendiaminetetra-azijnzuur 0,2 g - kationogeen polymeer bestaande uit zich herhalende eenheden met de formule 3 van het formuleblad 2,2 gby the Société SEPPIC 2.4 g - ethylenediamine tetraacetic acid 0.2 g - cationic polymer consisting of repeating units of the formula 3 of the formula sheet 2.2 g
- mono-ethanolamine 7.5 S- monoethanolamine 7.5 S
- diethanolamide van linolzuur verkocht onder de aanduiding COMPERLAN F door de Société HENKEL 8,0 g - ammoniak 20% 10,2 g - 35%'s oplossing in water van natriumrnetabisulfiet 1,3 g - hydrochinon 0,15 g - l-fenyl-3-methyl-5-pyrazolon 0,2 g - gedemineraliseerd water aanvullen tot 100,0 g- diethanolamide of linoleic acid sold under the designation COMPERLAN F by the Société HENKEL 8.0 g - ammonia 20% 10.2 g - 35% aqueous solution of sodium netabisulfite 1.3 g - hydroquinone 0.15 g - l-phenyl -3-methyl-5-pyrazolone 0.2 g - make up demineralized water to 100.0 g
Het preparaat wordt gemengd op het moment van het gebruik, gewicht op gewicht, met water dat met 20 volumes zuurstof verrijkt is en waarvan de pH gelijk is aan 3·The preparation is mixed at the time of use, weight by weight, with water enriched with 20 volumes of oxygen, the pH of which is equal to 3 ·
Het aldus verkregen mengsel wordt gedurende 30 minuten aangebracht op grijs haar met een witheid van 90%, daarna gespoeld, gewassen, opnieuw gespoeld en gedroogd.The mixture thus obtained is applied to gray hair of 90% whiteness for 30 minutes, then rinsed, washed, rinsed again and dried.
De kleur is donker koperachtig beigeblond.The color is dark coppery beige blonde.
Voorbeeld 7Example 7
Men herhaalt voorbeeld 6 onder toepassing van 0,29 g 7-hydroxy-3~ methylindool in plaats van 0,35 ë 6-hydroxy-2-carboxyindool,Example 6 is repeated using 0.29 g of 7-hydroxy-3-methylindole instead of 0.35-6-hydroxy-2-carboxyindole,
De omstandigheden bij het verven zijn gelijk aan die van voorbeeld 6. De haren worden geverfd in licht blonde mahonie-parelmoerachtige kleur.Dyeing conditions are the same as in Example 6. The hairs are dyed in a light blond mahogany-pearly color.
Voorbeeld 8Example 8
Men herhaalt voorbeeld 6 onder toepassing van 0,32 g 6-hydroxy- 2,3-dimethylindool in plaats van 0,33 ë 6-hydroxy-2-carboxyindool.Example 6 is repeated using 0.32 g of 6-hydroxy-2,3-dimethylindole instead of 0.33-6-hydroxy-2-carboxyindole.
De omstandigheden bij het verven zijn gelijk aan die van voorbeeld 6. De haren worden licht blond parelmoerachtig geverfd.The dyeing conditions are the same as in Example 6. The hairs are dyed a light blond pearlescent.
Toepassingsvoorbeeld 9Application example 9
Men bereidt het volgende verfmengsel: - 7“hydroxyindool 0,27 g - parafenyleendiamine 0,22 gThe following paint mixture is prepared: - 7 "hydroxyindole 0.27 g - paraphenylenediamine 0.22 g
- octyldodecanol verkocht onder de aanduiding EUTAN0L G- octyldodecanol sold under the designation EUTAN0L G
door de Sociêté HENKEL 8,0 g - oliezuur 20,0 g - mono-ethanolamine van laurylethersulfaat verkocht onder de aanduiding SIPON LM 35 door de Société HENKEL 3.0 g - ethylalcohol 10,0 g - benzylalcohol 10,0 gby the Sociêté HENKEL 8.0 g - oleic acid 20.0 g - monoethanolamine of lauryl ether sulfate sold under the designation SIPON LM 35 by the Société HENKEL 3.0 g - ethyl alcohol 10.0 g - benzyl alcohol 10.0 g
- cetylstearylalcohol geoxyethyleneerd met 33 mol ethyleenoxide verkocht onder de aanduiding SIMULS0L GS- cetylstearyl alcohol oxyethylenated with 33 moles of ethylene oxide sold under the designation SIMULS0L GS
door de Société SEPPIC 2,4 g - ethyleendiaminetetra-azijnzuur 0,2 g - kationogeen polymeer bestaande uit zich herhalende eenheden met de formule 3 van het formuleblad 2,2 g - mono-ethanolamine 7.5 ë - diethanolamide van linolzuur verkocht onder de aanduiding COMPERLAN F door de Société HENKEL 8,0 g - ammoniak 20% 10,2 g - 35#'s oplossing in water van natriummetabisulfiet 1,3 ë - hydrochinon 0,15 ë - l-fenyl-3-methyl-5-pyrazolon 0,2 g - gedemineraliseerd water aanvullen tot 100,0 gby the Société SEPPIC 2.4 g - ethylenediaminetetraacetic acid 0.2 g - cationic polymer consisting of repeating units of the formula 3 of the formula sheet 2.2 g - monoethanolamine 7.5 ë - diethanolamide of linoleic acid sold under the designation COMPERLAN F by the Société HENKEL 8.0 g - ammonia 20% 10.2 g - 35 # aqueous solution of sodium metabisulfite 1.3 ë - hydroquinone 0.15 ë - 1-phenyl-3-methyl-5-pyrazolone 0 , 2 g - make up demineralized water to 100.0 g
Het preparaat wordt gemengd op het moment van het gebruik, gewicht op gewicht, met water dat verrijkt is met 20 volumes zuurstof en waarvan de pH 3 is.The preparation is mixed at the time of use, weight by weight, with water enriched with 20 volumes of oxygen and the pH of which is 3.
Het aldus verkregen mengsel wordt gedurende 30 minuten aangebracht op grijze haren met een witheidspercentage van 90#, daarna gespoeld, gewassen, opnieuw gespoeld en gedroogd.The mixture thus obtained is applied to gray hairs with a 90% whiteness for 30 minutes, then rinsed, washed, rinsed again and dried.
De kleuring is donker askleurig parelmoerachtig blond.The coloration is dark ash-colored pearly blond.
Toepassingsvoorbeeld 10Application example 10
Men bereidt het volgende verfmengsel: - Ί-hydroxyindool 0,53 g - p-aminofenol 0,44 gThe following paint mixture is prepared: - Ί-hydroxyindole 0.53 g - p-aminophenol 0.44 g
- octyldodecanol verkocht onder de aanduiding EUTAN0L G- octyldodecanol sold under the designation EUTAN0L G
door de Société HENKEL 8,0 g - oliezuur 20,0 g - mono-ethanolamine van laurylethersulfaat verkocht onder de aanduiding SIP0N LM 35 door de Société HENKEL 3.0 g - ethylalcohol 10,0 g - benzylalcohol 10,0 gby the Société HENKEL 8.0 g - oleic acid 20.0 g - monoethanolamine of lauryl ether sulfate sold under the designation SIP0N LM 35 by the Société HENKEL 3.0 g - ethyl alcohol 10.0 g - benzyl alcohol 10.0 g
- cetylstearylalcohol geoxyethyleneerd met 33 mol ethyleenoxide verkocht onder de aanduiding SIMULS0L GS- cetylstearyl alcohol oxyethylenated with 33 moles of ethylene oxide sold under the designation SIMULS0L GS
door de Société SEPPIC 2,4 g - ethyleendiaminetetra-azijnzuur 0,2 g - kationogeen polymeer bestaande uit zich herhalende eenheden met de formule 3 van het formuleblad 2,2 gby the Société SEPPIC 2.4 g - ethylenediamine tetraacetic acid 0.2 g - cationic polymer consisting of repeating units of the formula 3 of the formula sheet 2.2 g
- mono-ethanolamine 7,5 S- monoethanolamine 7.5 S
- diethanolamide van linolzuur verkocht onder de aanduiding COMPERLAN F door de Société HENKEL 8,0 g - ammoniak 20# 10,2 g - 35%'s oplossing in water van natriummetabisulfiet 1,3 g - hydrochinon 0,15 g - l-fenyl-3~methyl-5-pyrazolon 0,2 g - gedemineraliseerd water aanvullen tot 100,0 g- diethanolamide of linoleic acid sold under the designation COMPERLAN F by the Société HENKEL 8.0 g - ammonia 20 # 10.2 g - 35% aqueous solution of sodium metabisulfite 1.3 g - hydroquinone 0.15 g - l-phenyl -3-methyl-5-pyrazolone 0.2 g - make up demineralized water to 100.0 g
Het preparaat wordt gemengd op het moment van het gebruik, gewicht per gewicht, met water dat met 20 volumes zuurstof verrijkt is en waarvan de pH 3 bedraagt.The preparation is mixed at the time of use, weight by weight, with water enriched with 20 volumes of oxygen and the pH of which is 3.
Het aldus verkregen mengsel wordt gedurende 30 minuten aangebracht op grijze haren met een 90#'s witheid, daarna gespoeld, gewassen, opnieuw gespoeld en gedroogd.The mixture thus obtained is applied to gray hairs with a 90 # whiteness for 30 minutes, then rinsed, washed, rinsed again and dried.
De kleur is koperachtig parelmoerachtig blond.The color is coppery pearly blond.
Toepassingsvoorbeeld 11Application example 11
Men verft haarlokken met een 90%'s witheid met een preparaat (A<^) dat de volgende samenstelling heeft: - 6-hydroxyindool 2,0 g - ethanol 10,0 g - natriumlaurylethersulfaat 1,0 g - water aanvullen tot 100,0 gHair strands of 90% whiteness are dyed with a preparation (A <^) having the following composition: - 6-hydroxyindole 2.0 g - ethanol 10.0 g - sodium lauryl ether sulfate 1.0 g - make up to 100, 0 g
De inwerkingstijd bedraagt 10 minuten. Men verkrijgt op deze manier na spoelen en drogen, een grijze lok met parelmoerachtige glans. Door vervolgens 3 minuten een mengsel uit gelijke delen van een 0,5#'s oplossing van N, N-bis-fi-hydroxyethylparafenyleendiamine in water en water dat met 6% zuurstof verrijkt is (pH van het milieu ongeveer 7) aan te brengen, verkrijgt men na spoelen en drogen een haarlok die donkerblond met purperen glans gekleurd is.The exposure time is 10 minutes. In this way, after rinsing and drying, a gray strand with a pearly sheen is obtained. Then by applying a mixture of equal parts of a 0.5 # 's solution of N, N-bis-fi-hydroxyethyl paraphenylenediamine in water and water enriched with 6% oxygen (environmental pH about 7) for 3 minutes after rinsing and drying, a strand of hair which is colored dark blond with a purple sheen is obtained.
Toepassingsvoorbeeld 12Application example 12
Men bereidt een 2,5%’s oplossing van 6-hydroxyindool in hydroalco-hol met pH 9 (NaOH) die men aanbrengt op haar in een hoeveelheid van 2,5 g per g grijs haar. Men verkrijgt na een inwerkingstijd van 10 minuten, spoelen en drogen, grijze haren die licht askleurig zijn.A 2.5% solution of 6-hydroxyindole in hydroalcohol with pH 9 (NaOH) is prepared which is applied to hair in an amount of 2.5 g per g of gray hair. After an action time of 10 minutes, rinsing and drying, gray hairs which are slightly ash-colored are obtained.
Als men vervolgens een mengsel van gelijke gewichtshoeveelheden van een oplossing van 0,5# N-methoxyethylparafenyleendiamine met pH 10 en water dat met 6% zuurstof verrijkt is gedurende 3 minuten aanbrengt, verkrijgt men na spoelen en drogen, haren met een kastanje-achtige helder purperen kleur.When a mixture of equal proportions of a solution of 0.5 # N-methoxyethyl paraphenylenediamine with pH 10 and water enriched with 6% oxygen is applied for 3 minutes, then after rinsing and drying, hairs with a chestnut-like clear are obtained. purple color.
Bereidingsvoorbeeld 1Preparation example 1
Bereiding van 6-hydroxy-l-methylindoolPreparation of 6-hydroxy-1-methylindole
Eerste trap:First stage:
Bereiding van 6-benzyloxy-l-methylindoolPreparation of 6-benzyloxy-1-methylindole
Aan 125 g natriumcarbonaat in tabletvorm in 125 “1 water, voegt men 300 ml tolueen toe, 50 ml methylsulfaat en 7»36 g ammoniumwaterstof-sulfaat van tetrabutylammonium, daarna, onder roeren, 0,33 ooi (73»6 g) 6-benzyloxyindool. Na het einde van de exotherme reactie roert men nog 15 minuten. Het reactiemengsel wordt met twee volumes water verdund. Na afscheiding van de organische fase wordt de waterrijke fase met tolueen geëxtraheerd. Door indamping, na wassen met water en drogen van de organische fasen, verkrijgt men het beoogde produkt. Het smelt bij 79°G.To 125 g of sodium carbonate in tablet form in 125 µl of water, 300 ml of toluene, 50 ml of methyl sulfate and 7 µl of 36 g ammonium hydrogen sulfate of tetrabutyl ammonium are added, then, with stirring, 0.33 ml (73 µg) 6- benzyloxyindole. Stirring is continued for 15 minutes after the exothermic reaction has ended. The reaction mixture is diluted with two volumes of water. After separation of the organic phase, the aqueous phase is extracted with toluene. The intended product is obtained by evaporation, after washing with water and drying the organic phases. It melts at 79 ° G.
De analyse van het verkregen produkt, na herkristallisatie uit methanol, geeft de volgende resultaten:The analysis of the product obtained, after recrystallization from methanol, gives the following results:
Analyse Berekend voor GevondenAnalysis Calculated for Found
Cl6H15NOCl6H15NO
c 81,01 80,92 H 6,33 6,36 N 5,91 5,80 0 6,75 6,99c 81.01 80.92 H 6.33 6.36 N 5.91 5.80 0 6.75 6.99
Tweede trap:Second stage:
Bereiding van 6-hydroxy-l-methylindoolPreparation of 6-hydroxy-1-methylindole
Men verwarmt 30 minuten onder terugvloeikoeling het mengsel uit 0,24 mol (57 g) 6-benzyloxy-l-methylindool, 5,7 g 10#'s palladium op kool, 114 ml cyclohexeen en 170 ml ethanol van 96°. Men filtreert warm om de katalysator te verwijderen. Na indamping van het filtraat onder vacuum, verkrijgt men een olie die gesolubiliseerd in isopropylether, en na indamping tot droog, het gewenste produkt oplevert. Het smelt bij 74°C.The mixture is heated under reflux for 30 minutes from 0.24 mol (57 g) of 6-benzyloxy-1-methylindole, 5.7 g of 10 # 's palladium on carbon, 114 ml of cyclohexene and 170 ml of ethanol at 96 °. It is filtered hot to remove the catalyst. After evaporation of the filtrate under vacuum, an oil which is solubilized in isopropyl ether and after evaporation to dryness, yields the desired product. It melts at 74 ° C.
De analyse van het verkregen produkt geeft de volgende resultaten: Analyse Berekend voor Gevonden c9h9no C 73,47 73,57 H 6,12 6,12 N 9,52 9,39 0 10,88 11,07The analysis of the obtained product gives the following results: Analysis Calculated for Found c9h9no C 73.47 73.57 H 6.12 6.12 N 9.52 9.39 0 10.88 11.07
Bereldingsvoorbeeld 2Calculation example 2
Bereiding van 7~hydroxy-3~methylindoolPreparation of 7 ~ hydroxy-3 ~ methylindole
Eerste trap:First stage:
Bereiding van 1-f (31 -benzyloxy-5' -chloor-2’ -nitro) fenyl~l-2-cyaanpropaan Men brengt onder verwarming gedurende 8 uren het reactiemengsel uit 0,5 mol (151,2 g) van 3~benzyloxy-5~chloor-2-nitrofenylacetonitril, 152,6 g methyl jodide en 207 g kaliumcarbonaat in 500 ml aceton tot terugvloeikoeling. Het reactiemengsel wordt verdund met 4 kg ijswater dat toegevoegd is aan 500 ml azijnzuur. Het beoogde produkt precipiteert. Na herkristallisatie uit azijnzuur smelt het bij 180°C.Preparation of 1-f (31-benzyloxy-5'-chloro-2'-nitro) phenyl-1-2-cyanopropane The reaction mixture is brought under heating for 8 hours from 0.5 mol (151.2 g) of 3 ~ benzyloxy-5-chloro-2-nitrophenylacetonitrile, 152.6 g of methyl iodide and 207 g of potassium carbonate in 500 ml of acetone to reflux. The reaction mixture is diluted with 4 kg of ice water added to 500 ml of acetic acid. The intended product precipitates. After recrystallization from acetic acid, it melts at 180 ° C.
De analyse van het verkregen produkt geeft de volgende resultaten:The analysis of the product obtained gives the following results:
Analyse Berekend voor Gevonden C16H13N2°3C1 C 60,67 60,72 H 4,l4 4,12 N 8,84 8,64 0 15,15 15,01Analysis Calculated for Found C16H13N2 ° 3Cl C 60.67 60.72 H 4.14 N 8.82 8.64 0 15.15 15.01
Cl 11,19 11,34Cl 11.19 11.34
Tweede trap:Second stage:
Bereiding van 7~hydroxy-3-methylindoolPreparation of 7-hydroxy-3-methylindole
Men verwarmt onder terugvloeikoeling gedurende 4 uren het reactiemengsel uit 20 g l-[(3,-ben2yloxy-5,-chloor-2,-nitro)fenyl]-2-cyaanpropaan, 10 g 10Vs palladium op kool in 100 ml ethanol vermengd met 40 ml cyclohexeen. Aan het einde van de omzetting wordt de katalysator uit het reactiemengsel verwijderd door filtreren. Na toevoeging van kool aan het filtraat, filtrering en vervolgens indamping, verkrijgt men het beoogde produkt dat kristalliseert uit een mengsel van isopropyl-ether en chloroform. Het smelt bij 190°C.The reaction mixture is heated under reflux for 4 hours from 20 g of l - [(3-ben2yloxy-5, -chloro-2, -nitro) phenyl] -2-cyano-propane, 10 g of 10Vs palladium on carbon in 100 ml of ethanol mixed with 40 ml of cyclohexene. At the end of the reaction, the catalyst is removed from the reaction mixture by filtration. After adding carbon to the filtrate, filtration and then evaporation, the intended product is obtained which crystallizes from a mixture of isopropyl ether and chloroform. It melts at 190 ° C.
De analyse van het verkregen produkt geeft de volgende resultaten:The analysis of the product obtained gives the following results:
Analyse Berekend voor GevondenAnalysis Calculated for Found
CgHgNOCgHgNO
C 73,45 73,53 H 6,16 6,23 N 9,52 9A5 0 10,87 10,76C 73.45 73.53 H 6.16 6.23 N 9.52 9A5 0 10.87 10.76
Claims (20)
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 (3)
| Publication Number | Publication Date |
|---|---|
| NL8902281A true NL8902281A (en) | 1990-04-02 |
| NL194230B NL194230B (en) | 2001-06-01 |
| NL194230C NL194230C (en) | 2001-10-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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. |
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| 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. |
| EP2223920A3 (en) | 1996-06-19 | 2011-09-28 | Aventis Pharma Limited | Substituted azabicyclic compounds |
| WO2013148805A2 (en) | 2012-03-27 | 2013-10-03 | The Procter & Gamble Company | Hair colorant compositions comprising 3- amino -2,6- dimethylphenol and 4- aminophenol-type developers, methods, and kits comprising the compositions |
| EP2830578B1 (en) | 2012-03-27 | 2020-02-26 | Noxell Corporation | Hair colorant compositions comprising amino -2,6- dimethylphenol and 1,4- phenylenediamine-type developers, 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 BE BE8900961A patent/BE1002235A4/en not_active IP Right Cessation
- 1989-09-11 BR BR898904562A patent/BR8904562A/en not_active IP Right Cessation
- 1989-09-11 IT IT8967751A patent/IT1232920B/en active
- 1989-09-11 FR FR8911815A patent/FR2636236B1/en not_active Expired - Lifetime
- 1989-09-11 AR AR89314892A patent/AR245515A1/en active
- 1989-09-11 GB GB8920524A patent/GB2224518B/en not_active Expired - Lifetime
- 1989-09-11 AU AU41207/89A patent/AU626579B2/en not_active Expired
- 1989-09-11 ES ES8903090A patent/ES2016162A6/en not_active Expired - Fee Related
- 1989-09-12 DE DE3930473A patent/DE3930473B4/en not_active Expired - Lifetime
- 1989-09-12 CA CA000611132A patent/CA1341195C/en not_active Expired - Lifetime
- 1989-09-12 KR KR1019890013240A patent/KR0172112B1/en not_active IP Right Cessation
- 1989-09-12 JP JP1236768A patent/JP2744080B2/en not_active Expired - Lifetime
- 1989-09-12 NL NL8902281A patent/NL194230C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT91663A (en) | 1990-03-30 |
| DE3930473B4 (en) | 2006-04-27 |
| KR0172112B1 (en) | 1999-02-01 |
| ES2016162A6 (en) | 1990-10-16 |
| IT1232920B (en) | 1992-03-05 |
| AU626579B2 (en) | 1992-08-06 |
| GR1000461B (en) | 1992-07-30 |
| JPH02121912A (en) | 1990-05-09 |
| BR8904562A (en) | 1990-05-01 |
| PT91663B (en) | 1995-08-09 |
| LU87337A1 (en) | 1990-04-06 |
| AR245515A1 (en) | 1994-01-31 |
| ATA210089A (en) | 1995-07-15 |
| GB2224518A (en) | 1990-05-09 |
| GB8920524D0 (en) | 1989-10-25 |
| GR890100568A (en) | 1990-10-31 |
| CH679551A5 (en) | 1992-03-13 |
| DE3930473A1 (en) | 1990-03-15 |
| NL194230C (en) | 2001-10-02 |
| IT8967751A0 (en) | 1989-09-11 |
| FR2636236A1 (en) | 1990-03-16 |
| AT400672B (en) | 1996-02-26 |
| CA1341195C (en) | 2001-02-27 |
| FR2636236B1 (en) | 1993-10-22 |
| JP2744080B2 (en) | 1998-04-28 |
| GB2224518B (en) | 1992-07-22 |
| ZA896845B (en) | 1991-05-29 |
| NL194230B (en) | 2001-06-01 |
| AU4120789A (en) | 1990-03-15 |
| KR900004317A (en) | 1990-04-12 |
| BE1002235A4 (en) | 1990-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BC | A request for examination has been filed | ||
| V4 | Discontinued because of reaching the maximum lifetime of a patent |
Effective date: 20090912 |