TWI412565B - 染料、染髮組成物及染髮之方法 - Google Patents
染料、染髮組成物及染髮之方法 Download PDFInfo
- Publication number
- TWI412565B TWI412565B TW096104463A TW96104463A TWI412565B TW I412565 B TWI412565 B TW I412565B TW 096104463 A TW096104463 A TW 096104463A TW 96104463 A TW96104463 A TW 96104463A TW I412565 B TWI412565 B TW I412565B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- hydrogen
- substituted
- phenyl
- group
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000000118 hair dye Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000004040 coloring Methods 0.000 title abstract description 3
- 239000000975 dye Substances 0.000 claims abstract description 98
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 113
- 239000001257 hydrogen Substances 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 230000001590 oxidative effect Effects 0.000 claims description 13
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 9
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical group CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- -1 alkoxy oxime Chemical class 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000982 direct dye Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000283707 Capra Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000001045 blue dye Substances 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000037308 hair color Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000001005 nitro dye Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000020681 well water Nutrition 0.000 description 4
- 239000002349 well water Substances 0.000 description 4
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000172533 Viola sororia Species 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000001000 anthraquinone dye Substances 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000001024 permanent hair color Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XXZFCJVFXKCILB-UHFFFAOYSA-N 1-methylpyrrolidine;hydrobromide Chemical compound [Br-].C[NH+]1CCCC1 XXZFCJVFXKCILB-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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-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
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000009038 Viola odorata Species 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019646 color tone Nutrition 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000001026 semi permanent hair color Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical group [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 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
- VIXBPSTZNCRCJE-UHFFFAOYSA-N 1,3-bis[4-amino-n-(2-hydroxyethyl)anilino]propan-2-ol Chemical compound C1=CC(N)=CC=C1N(CCO)CC(O)CN(CCO)C1=CC=C(N)C=C1 VIXBPSTZNCRCJE-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
- AQNZDXHBYRTSHA-UHFFFAOYSA-N 1,4-bis(2,3-dihydroxypropylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCC(O)CO)=CC=C2NCC(O)CO AQNZDXHBYRTSHA-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 description 1
- XWIBNOGPNKMAPE-UHFFFAOYSA-N 1-(2-hydroxyethylamino)-4-(3-hydroxypropylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NCCCO XWIBNOGPNKMAPE-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-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
- 229940113489 2,4-diaminophenoxyethanol Drugs 0.000 description 1
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- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-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
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- LLLILZLFKGJCCV-UHFFFAOYSA-M n-methyl-n-[(1-methylpyridin-1-ium-4-yl)methylideneamino]aniline;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=CC=CC=1N(C)\N=C\C1=CC=[N+](C)C=C1 LLLILZLFKGJCCV-UHFFFAOYSA-M 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- IPSIPYMEZZPCPY-UHFFFAOYSA-N new fuchsin Chemical compound [Cl-].C1=CC(=[NH2+])C(C)=CC1=C(C=1C=C(C)C(N)=CC=1)C1=CC=C(N)C(C)=C1 IPSIPYMEZZPCPY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 108090000623 proteins and genes Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-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
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- DJDYMAHXZBQZKH-UHFFFAOYSA-M sodium;1-amino-4-(cyclohexylamino)-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1CCCCC1 DJDYMAHXZBQZKH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/501—Amino-hydroxy-anthraquinones; Ethers and esters thereof containing onium groups
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
- A61K8/355—Quinones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
- C07C225/36—Amino anthraquinones the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/207—Dyes with amino groups and with onium groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
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| EP06101466A EP1820826A1 (en) | 2006-02-09 | 2006-02-09 | Dyestuffs and Hair Dye Compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200732427A TW200732427A (en) | 2007-09-01 |
| TWI412565B true TWI412565B (zh) | 2013-10-21 |
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| TW096104463A TWI412565B (zh) | 2006-02-09 | 2007-02-07 | 染料、染髮組成物及染髮之方法 |
| TW096104464A TW200731994A (en) | 2006-02-09 | 2007-02-07 | Hair dye compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096104464A TW200731994A (en) | 2006-02-09 | 2007-02-07 | Hair dye compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20090249564A1 (enExample) |
| EP (3) | EP1820826A1 (enExample) |
| JP (2) | JP5176026B2 (enExample) |
| KR (2) | KR20080093115A (enExample) |
| CN (2) | CN101379144B (enExample) |
| AU (2) | AU2007213796A1 (enExample) |
| CA (2) | CA2641863A1 (enExample) |
| RU (2) | RU2008136055A (enExample) |
| TW (2) | TWI412565B (enExample) |
| WO (2) | WO2007090799A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2329809A4 (en) * | 2008-08-19 | 2015-04-15 | Kao Corp | hair dye |
| WO2012084817A2 (en) | 2010-12-20 | 2012-06-28 | L'oreal | Dye composition comprising benzyl alcohol, a monoalcohol and a particular direct dye |
| EP2468245A1 (en) * | 2010-12-27 | 2012-06-27 | KPSS-Kao Professional Salon Services GmbH | Dyeing composition for keratin fibers |
| DE102011089218A1 (de) * | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Färbemittel mit kationischen direktziehenden Farbstoffen und Lecithine |
| DE102011089220A1 (de) | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern enthaltend kationische Anthrachinonfarbstoffe und Fettsäuretriglyceride |
| DE102011089216A1 (de) * | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Färbemittel mit direktziehenden Farbstoffen und amphotere Tensiden |
| DE102011089217A1 (de) | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern enthaltend hationische Anthrachinonfarbstoffe und anionische Polymere |
| DE102011089219A1 (de) | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Färbemittel mit direktziehenden Farbstoffen und nichtionischen Tensiden |
| DE102011089222A1 (de) | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Mittel zum Färben von keratinischen Fasern enthaltend kationische Anthrachinonfarbstoffe und Fettsäurediester von Alkandiolen |
| DE102011089221A1 (de) * | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Färbemittel mit direktziehenden Farbstoffen und Phospat-Tensiden |
| DE102011089223A1 (de) | 2011-12-20 | 2013-06-20 | Henkel Ag & Co. Kgaa | Färbemittel mit direktziehenden Farbstoffen und zwitterionischen Tensiden |
| RU2742123C1 (ru) * | 2017-09-20 | 2021-02-02 | Као Корпорейшн | Порошковая композиция, включающая прямые красители для волос |
| TW202228634A (zh) * | 2020-09-30 | 2022-08-01 | 日商花王股份有限公司 | 含藍色染料之染毛組合物 |
| EP4221843A1 (en) * | 2020-09-30 | 2023-08-09 | Kao Corporation | Hair dyeing composition with improved durability |
| TW202228635A (zh) * | 2020-09-30 | 2022-08-01 | 日商花王股份有限公司 | 包含直接染料之用於角蛋白纖維之漂白及著色組合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5891200A (en) * | 1995-08-07 | 1999-04-06 | Lim; Mu-Ill | Hair dye compositions containing anthraquinone dyes having a quaternary ammonium side chain and neutral direct dyes |
| US6437149B1 (en) * | 1998-11-30 | 2002-08-20 | L'oreal S.A. | Cationic aminoanthraquinones, their use for dyeing keratinous fibers, dyeing compositions containing them and methods of dyeing |
| CN1549700A (zh) * | 2001-09-12 | 2004-11-24 | P&G | 包含直接染料的毛发增亮着色剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR13564E (fr) * | 1908-06-25 | 1911-05-12 | Farbenfab Vorm Bayer F & Co | Procédé de production de nouveaux dérivés de la série de l'anthracène et les produits qui en résultent |
| US2737517A (en) * | 1954-05-25 | 1956-03-06 | Du Pont | Quaternary ammonium anthraquinone salts |
| DE1150652B (de) * | 1955-08-30 | 1963-06-27 | Bayer Ag | Faerben von Polyacrylnitrilfasern |
| BE581785A (enExample) * | 1957-06-13 | |||
| DE1286666B (de) * | 1962-04-05 | 1969-01-09 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen, kationischen Farbstoffen |
| FR1363216A (fr) * | 1962-04-05 | 1964-06-12 | Hoechst Ag | Colorants cationiques hydrosolubles et leur préparation |
| NL302452A (enExample) * | 1962-10-29 | |||
| DE1203915B (de) * | 1963-09-04 | 1965-10-28 | Therachemie Chem Therapeut | Haarfaerbemittel |
| DE1248865C2 (de) * | 1963-09-04 | 1975-01-09 | Henkel & Cie GmbH, 4000 Düsseldorf | Mittel zum faerben von haaren |
| CH463666A (de) * | 1964-09-10 | 1968-10-15 | Sandoz Ag | Verfahren zur Herstellung von Farbstoffen |
| GB1050863A (enExample) * | 1964-02-05 | |||
| CH476798A (de) | 1965-04-05 | 1969-08-15 | Allied Chem | Verfahren zur Herstellung von Anthrachinonfarbstoffen |
| CH488781A (de) * | 1966-07-04 | 1970-04-15 | Ciba Geigy | Verfahren zur Herstellung basischer Azofarbstoffe |
| DE1619365A1 (de) * | 1967-04-14 | 1969-09-04 | Basf Ag | Verfahren zum Faerben von sauer modifizierten Polyamiden |
| US3652601A (en) * | 1968-02-12 | 1972-03-28 | Sandoz Ltd | Anthraquinone dyes |
| GB1248652A (en) * | 1968-04-25 | 1971-10-06 | Du Pont | Water-insoluble dye salts |
| GB1270107A (en) * | 1968-05-15 | 1972-04-12 | Ici Ltd | Anthraquinone dyestuffs |
| GB1205365A (en) * | 1969-05-27 | 1970-09-16 | Gillette Industries Ltd | Anthraquinone dyes |
| DE2533428A1 (de) * | 1975-07-25 | 1977-02-10 | Bayer Ag | Kationische farbstoffe |
| GB1537253A (en) * | 1976-05-28 | 1978-12-29 | Ici Ltd | Disperse anthraquinone dyestuffs |
| FR2667788B1 (fr) * | 1990-10-12 | 1994-12-02 | Oreal | Utilisation d'hydroxyalkylamino-9,10-anthraquinones pour la teinture de fibres keratiniques humaines, composition cosmetique les contenant en association avec des colorants azouiques et nitres. |
| JP2561185B2 (ja) * | 1991-07-31 | 1996-12-04 | 株式会社粘土科学研究所 | プロテクトクリーム |
| DE4225644A1 (de) * | 1992-08-03 | 1994-02-10 | Koerber Ag | Vorrichtung zum Abstreifen von Tabakpartikeln von einem Förderer |
| US5486629A (en) * | 1992-09-01 | 1996-01-23 | Clairol, Inc. | Direct dyes having a quaternary center with a long aliphatic chain |
| GB9402607D0 (en) * | 1994-02-10 | 1994-04-06 | Zeneca Ltd | Process |
| JPH08217652A (ja) * | 1994-12-16 | 1996-08-27 | Yamahatsu Sangyo Kk | 酸化染毛剤組成物 |
| US5746779A (en) * | 1996-07-12 | 1998-05-05 | Bristol-Myers Squibb Company | Quaternized blue anthraqinone hair dyes in an isatin/amine dye system |
| EP0852136A1 (de) * | 1996-11-19 | 1998-07-08 | Ciba SC Holding AG | Verfahren zum Färben von keratinhaltigen Fasern |
| US5961664A (en) * | 1997-07-10 | 1999-10-05 | Bristol-Myers Squibb Company | Direct hair dye compositions and methods containing novel anthraquinone mixtures |
| JP3854736B2 (ja) * | 1998-11-06 | 2006-12-06 | ライオン株式会社 | 染毛剤組成物 |
| JP4471051B2 (ja) * | 1999-06-22 | 2010-06-02 | ライオン株式会社 | 染毛剤組成物及びその製造方法 |
-
2006
- 2006-02-09 EP EP06101466A patent/EP1820826A1/en not_active Withdrawn
-
2007
- 2007-02-02 KR KR1020087018957A patent/KR20080093115A/ko not_active Ceased
- 2007-02-02 US US12/278,715 patent/US20090249564A1/en not_active Abandoned
- 2007-02-02 JP JP2008553733A patent/JP5176026B2/ja not_active Expired - Fee Related
- 2007-02-02 KR KR1020087018980A patent/KR20080094674A/ko not_active Withdrawn
- 2007-02-02 WO PCT/EP2007/051041 patent/WO2007090799A2/en not_active Ceased
- 2007-02-02 RU RU2008136055/04A patent/RU2008136055A/ru not_active Application Discontinuation
- 2007-02-02 AU AU2007213796A patent/AU2007213796A1/en not_active Abandoned
- 2007-02-02 EP EP07704328A patent/EP1984458A2/en not_active Withdrawn
- 2007-02-02 US US12/279,003 patent/US7776106B2/en not_active Expired - Fee Related
- 2007-02-02 RU RU2008136053/04A patent/RU2008136053A/ru not_active Application Discontinuation
- 2007-02-02 CN CN2007800048244A patent/CN101379144B/zh not_active Expired - Fee Related
- 2007-02-02 CA CA002641863A patent/CA2641863A1/en not_active Abandoned
- 2007-02-02 WO PCT/EP2007/051043 patent/WO2007090800A2/en not_active Ceased
- 2007-02-02 JP JP2008553732A patent/JP5286567B2/ja active Active
- 2007-02-02 CN CNA2007800048348A patent/CN101379145A/zh active Pending
- 2007-02-02 CA CA002641838A patent/CA2641838A1/en not_active Abandoned
- 2007-02-02 EP EP07704330A patent/EP1984459A2/en not_active Withdrawn
- 2007-02-02 AU AU2007213797A patent/AU2007213797A1/en not_active Abandoned
- 2007-02-07 TW TW096104463A patent/TWI412565B/zh active
- 2007-02-07 TW TW096104464A patent/TW200731994A/zh unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5891200A (en) * | 1995-08-07 | 1999-04-06 | Lim; Mu-Ill | Hair dye compositions containing anthraquinone dyes having a quaternary ammonium side chain and neutral direct dyes |
| US6437149B1 (en) * | 1998-11-30 | 2002-08-20 | L'oreal S.A. | Cationic aminoanthraquinones, their use for dyeing keratinous fibers, dyeing compositions containing them and methods of dyeing |
| CN1549700A (zh) * | 2001-09-12 | 2004-11-24 | P&G | 包含直接染料的毛发增亮着色剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1984458A2 (en) | 2008-10-29 |
| EP1820826A1 (en) | 2007-08-22 |
| WO2007090799A3 (en) | 2008-01-10 |
| AU2007213797A1 (en) | 2007-08-16 |
| CN101379144B (zh) | 2012-08-22 |
| WO2007090799A2 (en) | 2007-08-16 |
| TW200732427A (en) | 2007-09-01 |
| US20090217466A1 (en) | 2009-09-03 |
| RU2008136055A (ru) | 2010-03-20 |
| WO2007090800A3 (en) | 2007-12-21 |
| TW200731994A (en) | 2007-09-01 |
| JP5176026B2 (ja) | 2013-04-03 |
| WO2007090800A2 (en) | 2007-08-16 |
| KR20080094674A (ko) | 2008-10-23 |
| CA2641838A1 (en) | 2007-08-16 |
| KR20080093115A (ko) | 2008-10-20 |
| JP2009529582A (ja) | 2009-08-20 |
| CA2641863A1 (en) | 2007-08-16 |
| JP2009531285A (ja) | 2009-09-03 |
| AU2007213796A1 (en) | 2007-08-16 |
| JP5286567B2 (ja) | 2013-09-11 |
| CN101379144A (zh) | 2009-03-04 |
| US20090249564A1 (en) | 2009-10-08 |
| US7776106B2 (en) | 2010-08-17 |
| RU2008136053A (ru) | 2010-03-20 |
| EP1984459A2 (en) | 2008-10-29 |
| CN101379145A (zh) | 2009-03-04 |
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