KR20030070046A - 디아미노피라졸 유도체 및 케라틴 섬유의 산화 염색을위한 이들의 용도 - Google Patents
디아미노피라졸 유도체 및 케라틴 섬유의 산화 염색을위한 이들의 용도 Download PDFInfo
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- KR20030070046A KR20030070046A KR10-2003-7007496A KR20037007496A KR20030070046A KR 20030070046 A KR20030070046 A KR 20030070046A KR 20037007496 A KR20037007496 A KR 20037007496A KR 20030070046 A KR20030070046 A KR 20030070046A
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- South Korea
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- dyeing
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- 238000004043 dyeing Methods 0.000 title claims abstract description 33
- 239000000835 fiber Substances 0.000 title claims abstract description 28
- KGBBJPZIDRELDP-UHFFFAOYSA-N 1h-pyrazole-3,5-diamine Chemical class NC=1C=C(N)NN=1 KGBBJPZIDRELDP-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000003647 oxidation Effects 0.000 title claims description 8
- 238000007254 oxidation reaction Methods 0.000 title claims description 8
- 230000001590 oxidative effect Effects 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 210000004209 hair Anatomy 0.000 claims abstract description 24
- 102000011782 Keratins Human genes 0.000 claims abstract description 21
- 108010076876 Keratins Proteins 0.000 claims abstract description 21
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 29
- -1 methoxy, 2-hydroxyethyloxy, 2-hydroxyethylamino, monomethylamino Chemical group 0.000 claims description 27
- 239000002585 base Substances 0.000 claims description 24
- 239000003086 colorant Substances 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 6
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1h-pyrazole-4,5-diamine Chemical compound NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 4
- 150000003893 lactate salts Chemical class 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical compound CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 claims description 2
- HQMMXKOLXQGSPP-UHFFFAOYSA-N 2-(2-methoxyethyl)-3-n-methylpyrazole-3,4-diamine Chemical compound CNC1=C(N)C=NN1CCOC HQMMXKOLXQGSPP-UHFFFAOYSA-N 0.000 claims description 2
- XCYBHMYDBNMESR-UHFFFAOYSA-N 2-(2-methoxyethyl)pyrazole-3,4-diamine Chemical compound COCCN1N=CC(N)=C1N XCYBHMYDBNMESR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000004950 naphthalene Polymers 0.000 claims description 2
- 150000002790 naphthalenes Polymers 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HUEFSFAVCVCTAX-UHFFFAOYSA-N 3,5-dibromo-4-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C=1C(Br)=NNC=1Br HUEFSFAVCVCTAX-UHFFFAOYSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- TXQKCKQJBGFUBF-UHFFFAOYSA-N 3,4,5-tribromo-1h-pyrazole Chemical compound BrC1=NNC(Br)=C1Br TXQKCKQJBGFUBF-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- XTPFYEWNZFBALH-UHFFFAOYSA-N 3,4,5-tribromo-1-nitropyrazole Chemical compound [O-][N+](=O)N1N=C(Br)C(Br)=C1Br XTPFYEWNZFBALH-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000035900 sweating Effects 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- CBWPAXKVACVBLU-UHFFFAOYSA-N 1,3-bis[4-amino-n-(2-hydroxyethyl)anilino]propan-1-ol Chemical compound C1=CC(N)=CC=C1N(CCO)CCC(O)N(CCO)C1=CC=C(N)C=C1 CBWPAXKVACVBLU-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- XYAQUYKPDDPZHG-UHFFFAOYSA-N 1-(4-aminoanilino)propan-2-ol Chemical compound CC(O)CNC1=CC=C(N)C=C1 XYAQUYKPDDPZHG-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- WSMJTXVQAZYLAV-UHFFFAOYSA-N 1-methylindol-4-ol Chemical compound C1=CC=C2N(C)C=CC2=C1O WSMJTXVQAZYLAV-UHFFFAOYSA-N 0.000 description 1
- KQGOJGSMIRVVJL-UHFFFAOYSA-N 1-n-methyl-4-n-[4-[4-(methylamino)anilino]butyl]benzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1NCCCCNC1=CC=C(NC)C=C1 KQGOJGSMIRVVJL-UHFFFAOYSA-N 0.000 description 1
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
- BXBOXUNPNIJELB-UHFFFAOYSA-N 2,6-dimethoxypyridine-3,5-diamine Chemical compound COC1=NC(OC)=C(N)C=C1N BXBOXUNPNIJELB-UHFFFAOYSA-N 0.000 description 1
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 1
- BQHMISUMCDYQTR-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylamino)ethanol Chemical compound OCCNC1=CC=C2OCOC2=C1 BQHMISUMCDYQTR-UHFFFAOYSA-N 0.000 description 1
- WCPGNFONICRLCL-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C(N)=C1 WCPGNFONICRLCL-UHFFFAOYSA-N 0.000 description 1
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-UHFFFAOYSA-N 0.000 description 1
- SRFUTMYQBQNJAA-UHFFFAOYSA-N 2-(2-methoxyethyl)pyrazole-3,4-diamine;dihydrochloride Chemical compound Cl.Cl.COCCN1N=CC(N)=C1N SRFUTMYQBQNJAA-UHFFFAOYSA-N 0.000 description 1
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 description 1
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 description 1
- FLCAOAGLACNSPB-UHFFFAOYSA-N 2-[4-amino-n-[2-[4-amino-n-(2-hydroxyethyl)anilino]ethyl]anilino]ethanol Chemical compound C1=CC(N)=CC=C1N(CCO)CCN(CCO)C1=CC=C(N)C=C1 FLCAOAGLACNSPB-UHFFFAOYSA-N 0.000 description 1
- BCQDCROHHKDXAT-UHFFFAOYSA-N 2-[4-amino-n-[4-[4-amino-n-(2-hydroxyethyl)anilino]butyl]anilino]ethanol Chemical compound C1=CC(N)=CC=C1N(CCO)CCCCN(CCO)C1=CC=C(N)C=C1 BCQDCROHHKDXAT-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
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- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- WNYJRJRHKRZXEO-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)C1=CC(N)=CC=C1N WNYJRJRHKRZXEO-UHFFFAOYSA-N 0.000 description 1
- YFHBPZJUEOCAMK-UHFFFAOYSA-N 2-propylbenzene-1,4-diamine Chemical compound CCCC1=CC(N)=CC=C1N YFHBPZJUEOCAMK-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 description 1
- JPWMYIUGFKNDSR-UHFFFAOYSA-N 3,5-dibromo-1-(2-methoxyethyl)-4-nitropyrazole Chemical compound COCCN1N=C(Br)C([N+]([O-])=O)=C1Br JPWMYIUGFKNDSR-UHFFFAOYSA-N 0.000 description 1
- XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 description 1
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical compound CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- MWKPYVXITDAZLL-UHFFFAOYSA-N 4-[3-(2,4-diaminophenoxy)propoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1N MWKPYVXITDAZLL-UHFFFAOYSA-N 0.000 description 1
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 description 1
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 description 1
- RGKJLNMYCNSVKZ-UHFFFAOYSA-N 4-amino-2-(methoxymethyl)phenol Chemical compound COCC1=CC(N)=CC=C1O RGKJLNMYCNSVKZ-UHFFFAOYSA-N 0.000 description 1
- UPHYVIFVOBTQNW-UHFFFAOYSA-N 4-amino-2-[(2-hydroxyethylamino)methyl]phenol Chemical compound NC1=CC=C(O)C(CNCCO)=C1 UPHYVIFVOBTQNW-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- DHKIYDNMIXSKQP-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C=C1CO DHKIYDNMIXSKQP-UHFFFAOYSA-N 0.000 description 1
- MNPLTKHJEAFOCA-UHFFFAOYSA-N 4-amino-3-fluorophenol Chemical compound NC1=CC=C(O)C=C1F MNPLTKHJEAFOCA-UHFFFAOYSA-N 0.000 description 1
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 1
- XCJRRZLPXALCIP-UHFFFAOYSA-N 4-n-(2-methoxyethyl)benzene-1,4-diamine Chemical compound COCCNC1=CC=C(N)C=C1 XCJRRZLPXALCIP-UHFFFAOYSA-N 0.000 description 1
- OAQDBKQAJRFJIY-UHFFFAOYSA-N 4-n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]-4-n-ethyl-2-methylbenzene-1,4-diamine Chemical compound C=1C=C(N)C(C)=CC=1N(CC)CCN(CC)C1=CC=C(N)C(C)=C1 OAQDBKQAJRFJIY-UHFFFAOYSA-N 0.000 description 1
- OOPWJBCZQDTTNE-UHFFFAOYSA-N 4-n-[4-(4-aminoanilino)butyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NCCCCNC1=CC=C(N)C=C1 OOPWJBCZQDTTNE-UHFFFAOYSA-N 0.000 description 1
- JRZODPDWGSVOGC-UHFFFAOYSA-N 5-(2-methoxyethyl)-4-nitro-1H-pyrazole Chemical compound COCCC=1NN=CC=1[N+]([O-])=O JRZODPDWGSVOGC-UHFFFAOYSA-N 0.000 description 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
- XTTMTABORBQMGI-UHFFFAOYSA-N 5-bromo-2-(2-methoxyethyl)-n-methyl-4-nitropyrazol-3-amine Chemical compound CNC1=C([N+]([O-])=O)C(Br)=NN1CCOC XTTMTABORBQMGI-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- MTAKAHRPGIVWAG-UHFFFAOYSA-N ClOCl.CNC1=C(N)C=NN1CCOC Chemical compound ClOCl.CNC1=C(N)C=NN1CCOC MTAKAHRPGIVWAG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- OYDQPYUVQAHEJH-UHFFFAOYSA-N [3-(dimethylamino)phenyl]urea Chemical compound CN(C)C1=CC=CC(NC(N)=O)=C1 OYDQPYUVQAHEJH-UHFFFAOYSA-N 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002610 basifying agent Substances 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- BKEFUBHXUTWQED-UHFFFAOYSA-N n-(4-amino-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C(O)=C1 BKEFUBHXUTWQED-UHFFFAOYSA-N 0.000 description 1
- AOJXAWIVWZQIKP-UHFFFAOYSA-N n-benzyl-5-bromo-2-(2-methoxyethyl)-4-nitropyrazol-3-amine Chemical compound COCCN1N=C(Br)C([N+]([O-])=O)=C1NCC1=CC=CC=C1 AOJXAWIVWZQIKP-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0015837A FR2817551B1 (fr) | 2000-12-06 | 2000-12-06 | Nouveaux derives de diaminopyrazole et leur utilisation en teinture d'oxydation des fibres keratiniques |
| FR0015837 | 2000-12-06 | ||
| PCT/FR2001/003778 WO2002046165A1 (fr) | 2000-12-06 | 2001-11-29 | Derives de diaminopyrazole et leur utilisation en teinture d'oxydation des fibres keratiniques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20030070046A true KR20030070046A (ko) | 2003-08-27 |
Family
ID=8857314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2003-7007496A Ceased KR20030070046A (ko) | 2000-12-06 | 2001-11-29 | 디아미노피라졸 유도체 및 케라틴 섬유의 산화 염색을위한 이들의 용도 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7250063B2 (enExample) |
| EP (1) | EP1339693A1 (enExample) |
| JP (1) | JP2004515495A (enExample) |
| KR (1) | KR20030070046A (enExample) |
| CN (1) | CN1478079A (enExample) |
| AR (1) | AR031774A1 (enExample) |
| AU (1) | AU2002222074A1 (enExample) |
| BR (1) | BR0116190A (enExample) |
| FR (1) | FR2817551B1 (enExample) |
| MX (1) | MXPA03005029A (enExample) |
| WO (1) | WO2002046165A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100667890B1 (ko) * | 2006-07-10 | 2007-01-11 | 주식회사 건화 | 친환경적인 하천 굴곡부의 사면보호시설 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2830190B1 (fr) * | 2001-09-28 | 2004-10-01 | Oreal | Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole, une base d'oxydation heterocyclique et un coupleur |
| FR2835742B1 (fr) * | 2002-02-12 | 2006-06-02 | Oreal | Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole, une base d'oxydation cationique et un coupleur |
| US7135046B2 (en) | 2003-06-19 | 2006-11-14 | L'oreal S.A. | Dye composition comprising at least one oxidation base chosen from 4,5-diamino-1-(β-hydroxyethyl)-1H-pyrazole and 4,5-diamino-1-(β-methoxyethyl)-1H-pyrazole and the addition salts thereof and at least one coupler chosen from 6-hydroxyindole and the addition salts thereof |
| FR2856291B1 (fr) * | 2003-06-19 | 2005-08-26 | Oreal | Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole ou le 4,5-diamino-1-(b-methoxyethyl)-1h-pyrazole a titre de base d'oxydation et le 6-hydroxy indole a titre de coupleur |
| FR2856292B1 (fr) * | 2003-06-19 | 2005-08-26 | Oreal | Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole ou le 4,5-diamino-1-(b-methoxyethyl)-1h-pyrazole a titre de base d'oxydation et la 2,6-diamino pyridine a titre de coupleur |
| FR2856290B1 (fr) * | 2003-06-19 | 2005-08-26 | Oreal | Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole comme base d'oxydation et la 2,6-dihydroxy-3,4-dimethyl pyridine comme coupleur |
| FR2856293B1 (fr) * | 2003-06-19 | 2005-08-26 | Oreal | Composition tinctoriale comprenant le 4,5-diamino-1-(b-hydroxyethyl)-1h-pyrazole comme base d'oxydation et le 2,6-bis-(b-hydroxyethyl)-amino toluene comme coupleur |
| US7150765B2 (en) | 2003-07-11 | 2006-12-19 | L'oreal S.A. | Fatty acid-free liquid dye composition comprising at least one oxidation base and 2-methyl-1, 3-propanediol, dyeing process, and device |
| DE10354584A1 (de) | 2003-11-21 | 2005-06-30 | Wella Ag | Kationische Diaminopyrazole, ein Verfahren zu deren Herstellung und diese Verbindungen enthaltende Färbemittel |
| BRPI0716024B1 (pt) | 2006-08-10 | 2015-12-22 | Combe Inc | corante capilar de oxidação catalisada em contato com o ar. |
| US8444710B2 (en) | 2011-02-22 | 2013-05-21 | The Procter & Gamble Company | Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a m-aminophenol and derivatives thereof |
| US8444714B2 (en) | 2011-02-22 | 2013-05-21 | The Procter & Gamble Company | Oxidative dyeing compositions comprising an 1-Hexy1/Hepty1-4,5-diaminopyrazole and a benzene-1,3-diol and derivatives thereof |
| WO2013085553A2 (en) | 2011-02-22 | 2013-06-13 | The Procter & Gamble Company | Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzo[1,3]dioxol-5-ylamine and derivatives thereof |
| WO2013085554A2 (en) | 2011-02-22 | 2013-06-13 | The Procter & Gamble Company | Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a naphthalen-1-ol and derivatives thereof |
| MX336045B (es) | 2011-02-22 | 2016-01-07 | Procter & Gamble | Composiciones para teñido oxidante que comprenden un 1-hexil/heptilo-4,5-diaminopirazol y un 2-aminofenol y derivados de estas. |
| JP2014510057A (ja) | 2011-02-22 | 2014-04-24 | ザ プロクター アンド ギャンブル カンパニー | １−ヘキシル／ヘプチル−４，５−ジアミノピラゾール及びピリジン、並びにそれらの誘導体を含有する酸化的染色組成物 |
| EP2677991A1 (en) | 2011-02-22 | 2014-01-01 | The Procter and Gamble Company | Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzene-1,3-diamine and derivatives thereof |
| EP2628731B1 (en) | 2012-02-16 | 2014-04-23 | The Procter and Gamble Company | 1-Hexyl-1H-pyrazole-4,5-diamine hemisulfate, and its use in dyeing compositions |
| EP2628730B1 (en) | 2012-02-16 | 2017-12-06 | Noxell Corporation | Telescoping synthesis of 5-amino-4-nitroso-1-alkyl-1h-pyrazole salts |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4234885A1 (de) * | 1992-10-16 | 1994-04-21 | Wella Ag | Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten, deren Verwendung zum Färben von Haaren sowie neue Pyrazol-Derivate |
| DE4234887A1 (de) * | 1992-10-16 | 1994-04-21 | Wella Ag | Oxidationshaarfärbemittel mit einem Gehalt an 4,5-Diaminopyrazolderivaten sowie neue 4,5-Diaminopyrazolderivate und Verfahren zu ihrer Herstellung |
| US5663366A (en) | 1992-10-16 | 1997-09-02 | Wella Aktiengesellschat | Process for the synthesis of 4,5-diaminopyrazole derivatives useful for dyeing hair |
| FR2733749B1 (fr) | 1995-05-05 | 1997-06-13 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation |
| DE19643059A1 (de) | 1996-10-18 | 1998-04-23 | Wella Ag | Mittel und Verfahren zur Färbung von keratinischer Fasern |
| DE19646609A1 (de) | 1996-11-12 | 1998-05-14 | Wella Ag | Färbemittel zur Erzeugung von Metamerie-Effekten auf Keratinfasern |
| DE19730412C1 (de) * | 1997-07-16 | 1998-12-03 | Wella Ag | Neue Bispyrazolazaverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Haarfärbemittel |
| FR2788521B1 (fr) * | 1999-01-19 | 2001-02-16 | Oreal | Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
| DE20013156U1 (de) * | 2000-07-28 | 2000-10-19 | Wella Ag | Färbemittel für Keratinfasern |
-
2000
- 2000-12-06 FR FR0015837A patent/FR2817551B1/fr not_active Expired - Fee Related
-
2001
- 2001-11-29 JP JP2002547904A patent/JP2004515495A/ja active Pending
- 2001-11-29 EP EP01999561A patent/EP1339693A1/fr not_active Withdrawn
- 2001-11-29 US US10/433,683 patent/US7250063B2/en not_active Expired - Fee Related
- 2001-11-29 AU AU2002222074A patent/AU2002222074A1/en not_active Abandoned
- 2001-11-29 BR BR0116190-3A patent/BR0116190A/pt not_active IP Right Cessation
- 2001-11-29 KR KR10-2003-7007496A patent/KR20030070046A/ko not_active Ceased
- 2001-11-29 WO PCT/FR2001/003778 patent/WO2002046165A1/fr not_active Ceased
- 2001-11-29 CN CNA018200370A patent/CN1478079A/zh active Pending
- 2001-11-29 MX MXPA03005029A patent/MXPA03005029A/es unknown
- 2001-12-04 AR ARP010105625A patent/AR031774A1/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100667890B1 (ko) * | 2006-07-10 | 2007-01-11 | 주식회사 건화 | 친환경적인 하천 굴곡부의 사면보호시설 |
Also Published As
| Publication number | Publication date |
|---|---|
| AR031774A1 (es) | 2003-10-01 |
| JP2004515495A (ja) | 2004-05-27 |
| FR2817551A1 (fr) | 2002-06-07 |
| EP1339693A1 (fr) | 2003-09-03 |
| US20040083558A1 (en) | 2004-05-06 |
| FR2817551B1 (fr) | 2005-07-01 |
| BR0116190A (pt) | 2004-02-25 |
| MXPA03005029A (es) | 2003-09-05 |
| AU2002222074A1 (en) | 2002-06-18 |
| WO2002046165A1 (fr) | 2002-06-13 |
| US7250063B2 (en) | 2007-07-31 |
| CN1478079A (zh) | 2004-02-25 |
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