CN101945640A - 从2-氯-3-氨基-6-甲基苯酚获得的偶氮甲碱直接染料或这些染料的还原前体、以及从这些染料或前体开始的染发方法 - Google Patents
从2-氯-3-氨基-6-甲基苯酚获得的偶氮甲碱直接染料或这些染料的还原前体、以及从这些染料或前体开始的染发方法 Download PDFInfo
- Publication number
- CN101945640A CN101945640A CN2008801271696A CN200880127169A CN101945640A CN 101945640 A CN101945640 A CN 101945640A CN 2008801271696 A CN2008801271696 A CN 2008801271696A CN 200880127169 A CN200880127169 A CN 200880127169A CN 101945640 A CN101945640 A CN 101945640A
- Authority
- CN
- China
- Prior art keywords
- amino
- formula
- chemical compound
- alkyl
- direct dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000982 direct dye Substances 0.000 title claims abstract description 43
- 238000004040 coloring Methods 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000002243 precursor Substances 0.000 title abstract description 18
- XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 title abstract description 9
- 230000009467 reduction Effects 0.000 title abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 238000004043 dyeing Methods 0.000 claims abstract description 26
- -1 inorganic acid salt Chemical class 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 239000000975 dye Substances 0.000 claims description 26
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 13
- 125000000129 anionic group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000001768 cations Chemical group 0.000 claims description 12
- 239000002537 cosmetic Substances 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 7
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229940097275 indigo Drugs 0.000 claims description 5
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 102000004316 Oxidoreductases Human genes 0.000 claims description 3
- 108090000854 Oxidoreductases Proteins 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 2
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 230000002421 anti-septic effect Effects 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 150000001538 azepines Chemical class 0.000 claims description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 229940078916 carbamide peroxide Drugs 0.000 claims description 2
- 229940106189 ceramide Drugs 0.000 claims description 2
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000002322 conducting polymer Substances 0.000 claims description 2
- 229920001940 conductive polymer Polymers 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003605 opacifier Substances 0.000 claims description 2
- 230000000149 penetrating effect Effects 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 235000013599 spices Nutrition 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
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 abstract description 10
- 230000002085 persistent effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 22
- 125000001841 imino group Chemical group [H]N=* 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- 239000000835 fiber Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- 239000000908 ammonium hydroxide Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 102000011782 Keratins Human genes 0.000 description 11
- 108010076876 Keratins Proteins 0.000 description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- MMJSNRLQVUQXKY-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol;hydrochloride Chemical compound Cl.CC1=CC=C(N)C(Cl)=C1O MMJSNRLQVUQXKY-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 235000011167 hydrochloric acid Nutrition 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical group NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 4
- GFAZBXKENDSJEB-UHFFFAOYSA-N 2,5-dihydroxy-3-methoxy-6-methylcyclohexa-2,5-diene-1,4-dione Chemical compound COC1=C(O)C(=O)C(C)=C(O)C1=O GFAZBXKENDSJEB-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 241001597008 Nomeidae Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- WDGFFVCWBZVLCE-UHFFFAOYSA-N purpurogallin Chemical compound C1=CC=C(O)C(=O)C2=C1C=C(O)C(O)=C2O WDGFFVCWBZVLCE-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 4
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 3
- OXZSHMLHGBOHFO-UHFFFAOYSA-N 3-amino-2-chloro-4-(4-hydroxyanilino)-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(NC=2C=CC(O)=CC=2)=C1N OXZSHMLHGBOHFO-UHFFFAOYSA-N 0.000 description 3
- WBDUMMMJVCKNHX-UHFFFAOYSA-N 3-amino-4-(4-aminoanilino)-2-chloro-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(NC=2C=CC(N)=CC=2)=C1N WBDUMMMJVCKNHX-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 3
- 229940006460 bromide ion Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 238000012805 post-processing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- LFOUYKNCQNVIGI-UHFFFAOYSA-N 2-(2-nitroanilino)ethanol Chemical compound OCCNC1=CC=CC=C1[N+]([O-])=O LFOUYKNCQNVIGI-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 206010049865 Achromotrichia acquired Diseases 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 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 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Natural products CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WLKAMFOFXYCYDK-UHFFFAOYSA-N [5-amino-4-[[3-[(2-amino-4-azaniumyl-5-methylphenyl)diazenyl]-4-methylphenyl]diazenyl]-2-methylphenyl]azanium;dichloride Chemical compound [Cl-].[Cl-].CC1=CC=C(N=NC=2C(=CC([NH3+])=C(C)C=2)N)C=C1N=NC1=CC(C)=C([NH3+])C=C1N WLKAMFOFXYCYDK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- IOFZRMMOGGEAGZ-UHFFFAOYSA-N 1,4-diamino-5-(2-hydroxyethyl)anthracene-9,10-dione Chemical compound O=C1C2=C(CCO)C=CC=C2C(=O)C2=C1C(N)=CC=C2N IOFZRMMOGGEAGZ-UHFFFAOYSA-N 0.000 description 1
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- KDUBHOYAJNACMY-UHFFFAOYSA-N 1-(2,3-dihydroxypropylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCC(O)CO KDUBHOYAJNACMY-UHFFFAOYSA-N 0.000 description 1
- UXFYNFPNBZUUIB-UHFFFAOYSA-N 1-(2-aminoethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCCN UXFYNFPNBZUUIB-UHFFFAOYSA-N 0.000 description 1
- NLXFWUZKOOWWFD-UHFFFAOYSA-N 1-(2-hydroxyethylamino)-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NC NLXFWUZKOOWWFD-UHFFFAOYSA-N 0.000 description 1
- ZJMNPETYAPSLTO-UHFFFAOYSA-N 1-amino-2-(1-aminopropyl)-4-(methylamino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(N)CC)=CC(NC)=C3C(=O)C2=C1 ZJMNPETYAPSLTO-UHFFFAOYSA-N 0.000 description 1
- ZYDHNFUOTQMBKJ-UHFFFAOYSA-N 1-amino-2-(1-aminopropyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(N)CC)=CC=C3C(=O)C2=C1 ZYDHNFUOTQMBKJ-UHFFFAOYSA-N 0.000 description 1
- ICVRBKCRXNVOJC-UHFFFAOYSA-N 1-amino-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2NC ICVRBKCRXNVOJC-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
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- OWMQBFHMJVSJSA-UHFFFAOYSA-N 2-(2-amino-4-nitroanilino)ethanol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1NCCO OWMQBFHMJVSJSA-UHFFFAOYSA-N 0.000 description 1
- AIVNWLRRKGRNCF-UHFFFAOYSA-N 2-(3-methyl-2-nitroanilino)ethanol Chemical compound CC1=CC=CC(NCCO)=C1[N+]([O-])=O AIVNWLRRKGRNCF-UHFFFAOYSA-N 0.000 description 1
- QNJWQAYYVNKOKR-UHFFFAOYSA-N 2-(4-amino-2-chloro-5-nitroanilino)ethanol Chemical compound NC1=CC(Cl)=C(NCCO)C=C1[N+]([O-])=O QNJWQAYYVNKOKR-UHFFFAOYSA-N 0.000 description 1
- LGZSBRSLVPLNTM-UHFFFAOYSA-N 2-(4-amino-2-methyl-5-nitroanilino)ethanol Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1NCCO LGZSBRSLVPLNTM-UHFFFAOYSA-N 0.000 description 1
- DAGCJJZWDAVKRE-UHFFFAOYSA-N 2-(4-amino-3-nitroanilino)ethanol Chemical compound NC1=CC=C(NCCO)C=C1[N+]([O-])=O DAGCJJZWDAVKRE-UHFFFAOYSA-N 0.000 description 1
- VPRLWNAMKBZKRR-UHFFFAOYSA-N 2-(4-nitroanilino)ethanol Chemical compound OCCNC1=CC=C([N+]([O-])=O)C=C1 VPRLWNAMKBZKRR-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NJZCRXQWPNNJNB-UHFFFAOYSA-N 2-[2-nitro-4-(trifluoromethyl)anilino]ethanol Chemical compound OCCNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O NJZCRXQWPNNJNB-UHFFFAOYSA-N 0.000 description 1
- NZKTVPCPQIEVQT-UHFFFAOYSA-N 2-[4-[(4-aminophenyl)diazenyl]-n-(2-hydroxyethyl)anilino]ethanol Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(N(CCO)CCO)C=C1 NZKTVPCPQIEVQT-UHFFFAOYSA-N 0.000 description 1
- SSRBPSAPLFYFAX-UHFFFAOYSA-N 2-[4-[ethyl(2-hydroxyethyl)amino]-2-nitroanilino]ethanol Chemical compound OCCN(CC)C1=CC=C(NCCO)C([N+]([O-])=O)=C1 SSRBPSAPLFYFAX-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- CDFNUSAXZDSXKF-UHFFFAOYSA-N 2-chloro-6-(ethylamino)-4-nitrophenol Chemical compound CCNC1=CC([N+]([O-])=O)=CC(Cl)=C1O CDFNUSAXZDSXKF-UHFFFAOYSA-N 0.000 description 1
- YPNZJHFXFVLXSE-UHFFFAOYSA-N 2-chloro-6-methylphenol Chemical compound CC1=CC=CC(Cl)=C1O YPNZJHFXFVLXSE-UHFFFAOYSA-N 0.000 description 1
- CVOFKRWYWCSDMA-UHFFFAOYSA-N 2-chloro-n-(2,6-diethylphenyl)-n-(methoxymethyl)acetamide;2,6-dinitro-n,n-dipropyl-4-(trifluoromethyl)aniline Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl.CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O CVOFKRWYWCSDMA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 1
- XDHQHBSDKYPJRG-UHFFFAOYSA-N 3-[2-nitro-4-(trifluoromethyl)anilino]propane-1,2-diol Chemical compound OCC(O)CNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O XDHQHBSDKYPJRG-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UXKLYBMQAHYULT-UHFFFAOYSA-N 4-(2-hydroxyethylamino)-3-nitrophenol Chemical compound OCCNC1=CC=C(O)C=C1[N+]([O-])=O UXKLYBMQAHYULT-UHFFFAOYSA-N 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 1
- SEVMQEIGENUPIE-UHFFFAOYSA-N 4-bromo-1-fluoro-2-methoxybenzene Chemical compound COC1=CC(Br)=CC=C1F SEVMQEIGENUPIE-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- GYQDOAKHUGURPD-UHFFFAOYSA-N 5,7-Dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride Chemical compound [Cl-].C1=CC(O)=CC=C1C1=CC=C(C(O)=CC(O)=C2)C2=[O+]1 GYQDOAKHUGURPD-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- CQPFMGBJSMSXLP-ZAGWXBKKSA-M Acid orange 7 Chemical compound OC1=C(C2=CC=CC=C2C=C1)/N=N/C1=CC=C(C=C1)S(=O)(=O)[O-].[Na+] CQPFMGBJSMSXLP-ZAGWXBKKSA-M 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- AOMZHDJXSYHPKS-DROYEMJCSA-L Amido Black 10B Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC=CC=3)C(O)=C2C(N)=C1\N=N\C1=CC=C(N(=O)=O)C=C1 AOMZHDJXSYHPKS-DROYEMJCSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- SKOROHCZPSASOW-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C(=C(C=C1)[As](O)(O)=O)O)NC(C)=O Chemical compound C1(=CC=CC=C1)C1=C(C(=C(C=C1)[As](O)(O)=O)O)NC(C)=O SKOROHCZPSASOW-UHFFFAOYSA-N 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- MOCDKTQQXVFPRJ-LICLKQGHSA-N CC(C(C(Cl)=C1N)=O)=C/C1=N\c(cc1)ccc1N Chemical compound CC(C(C(Cl)=C1N)=O)=C/C1=N\c(cc1)ccc1N MOCDKTQQXVFPRJ-LICLKQGHSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- 241000628997 Flos Species 0.000 description 1
- GZGZVOLBULPDFD-UHFFFAOYSA-N HC Red No. 3 Chemical compound NC1=CC=C(NCCO)C([N+]([O-])=O)=C1 GZGZVOLBULPDFD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229930182559 Natural dye Natural products 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229940099540 acid violet 43 Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229920013822 aminosilicone Polymers 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MCIURFJELJKSNV-UHFFFAOYSA-N benzene-1,4-diamine;hydron;chloride Chemical compound Cl.NC1=CC=C(N)C=C1 MCIURFJELJKSNV-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- VYTBDSUNRJYVHL-UHFFFAOYSA-N beta-Hydrojuglone Natural products O=C1CCC(=O)C2=C1C=CC=C2O VYTBDSUNRJYVHL-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000004161 brilliant blue FCF Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- DGQLVPJVXFOQEV-NGOCYOHBSA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-NGOCYOHBSA-N 0.000 description 1
- 229940114118 carminic acid Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000012754 curcumin Nutrition 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 229940109262 curcumin Drugs 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- LGWXIBBJZQOXSO-UHFFFAOYSA-L disodium 5-acetamido-4-hydroxy-3-[(2-methylphenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1C LGWXIBBJZQOXSO-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- RNQBLUNNAYFBIW-NPULLEENSA-M hexadecyl(trimethyl)azanium (2S)-2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound COc1ccc2cc(ccc2c1)[C@H](C)C([O-])=O.CCCCCCCCCCCCCCCC[N+](C)(C)C RNQBLUNNAYFBIW-NPULLEENSA-M 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- JGIDSJGZGFYYNX-YUAHOQAQSA-N indian yellow Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CC=C(OC=2C(=C(O)C=CC=2)C2=O)C2=C1 JGIDSJGZGFYYNX-YUAHOQAQSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- CXORMDKZEUMQHX-UHFFFAOYSA-N kermesic acid Chemical compound O=C1C2=C(O)C(O)=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C CXORMDKZEUMQHX-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229960003371 protocatechualdehyde Drugs 0.000 description 1
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 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
- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- VRDAELYOGRCZQD-NFLRKZIHSA-M sodium;4-[(2z)-2-[(5e)-5-[(2,4-dimethylphenyl)hydrazinylidene]-4,6-dioxocyclohex-2-en-1-ylidene]hydrazinyl]benzenesulfonate Chemical compound [Na+].CC1=CC(C)=CC=C1N\N=C(/C(=O)C=C\1)C(=O)C/1=N\NC1=CC=C(S([O-])(=O)=O)C=C1 VRDAELYOGRCZQD-NFLRKZIHSA-M 0.000 description 1
- FTUYQIPAPWPHNC-UHFFFAOYSA-M sodium;4-[[4-[benzyl(ethyl)amino]phenyl]-[4-[benzyl(ethyl)azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=CC=CC=2)C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC=C1 FTUYQIPAPWPHNC-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000979 synthetic dye Substances 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
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- DWKARHJHPSUOBW-UHFFFAOYSA-N trimethyl-[3-[(2e)-2-(3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)hydrazinyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(O)=C1N=NC1=CC=CC([N+](C)(C)C)=C1 DWKARHJHPSUOBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
- C07C251/22—Quinone imines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/413—Indoanilines; Indophenol; Indoamines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- 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
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C09B53/00—Quinone imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及使用从2-氯-3-氨基-6-甲基苯酚获得的式(I)的偶氮甲碱直接染料或式(II)的偶氮甲碱直接染料的还原前体进行的角蛋白纤维染色。本发明的一个主题是包含至少一种氯化偶氮甲碱直接染料或一种氯化偶氮甲碱直接染料的还原前体的染色组合物、使用所述组合物将角蛋白纤维染色的方法、及所述组合物在角蛋白纤维染色中的用途。该组合物可能获得特别稳定而持久的着色。
Description
本发明涉及使用从2-氯-3-氨基-6-甲基苯酚获得的偶氮甲碱直接染料或偶氮甲碱直接染料的还原前体进行的角蛋白纤维(keratinous fibre)染色。
已知按照“直接染色”方法,用包含直接染料的染色组合物将角蛋白纤维(尤其毛发)染色。
直接染色中中常规使用的方法包括将对所述纤维有亲合力的直接染料或着色分子施涂到角蛋白纤维上,使所述直接染料或着色分子静置,然后冲洗纤维。迄今使用的直接染料为硝基苯染料、蒽醌、硝基吡啶或偶氮染料、呫吨、吖啶、吖嗪或三芳基甲烷、苯衍生物类型。
其他染料从氧化显色碱(oxidation bases)和氧化成色(oxidation couplers)获得,一旦缩合,将其施涂到毛发上。例如文献FR 233 036、FR 2 262 022、FR 2 262 024、US 4 221 729和FR 2 261 750中,将二苯胺单独或与其他染料组合用于染色组合物,所述二苯胺如靛酚、靛胺和靛苯胺的无色衍生物。对应于无色衍生物的氧化衍生物的其他化合物(如文献FR 2 254 557和FR 2 234 277中描述的那些)也已知用于将角蛋白纤维染色。
直接染料产生的着色剂是临时或半永久性着色,因为将直接染料结合至角蛋白纤维的相互作用的性质和直接染料从纤维表面和/或芯的脱附导致其染色力差,且在洗涤或排汗时其染色牢度差。此外,这些直接染料一般对氧化剂(如过氧化氢水溶液)的作用敏感,这使得染料一般不能用于基于过氧化氢水溶液和基于碱化剂的增亮(lightening)直接染色组合物,其类似于氧化染色。
直接染料还显示出一定程度的光稳定性缺乏,这与发色团对光化学攻击的低抗性有关。此外,它们对光的敏感性依赖于其分子在基材中的分布(均匀或聚集)。
因此,确实需要找到有可能将角蛋白纤维染色的直接染料,所述直接染料对光稳定,所述直接染料还耐坏气候、耐洗涤操作和排汗,并在氧化剂(如过氧化氢水溶液)的存在下足够稳定,以能够同时获得纤维的增亮和上述优点,同时具有改善的并与角蛋白纤维上使用的化妆品相容的毒理学特性(profile)。
用本发明实现这些目标。本发明的主题是从式(I)的直接染料、其有机酸盐或无机酸盐、其几何异构体、其互变异构体和其溶剂合物(如水合物)开始将角蛋白纤维染色的方法:
在式(I)中:
·R1表示:
-氯原子;
-(C1-C3)烷基,其任选被一个或多个羟基取代;
-(C1-C3)烷氧基,其任选被一个或多个羟基取代;
·X表示:
-羟基;
--NR4R5基团,其中R4和R5各自独立地表示:
i)氢原子;
ii)C1-C5烷基,其任选被一个或多个选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、氨基羰基、羧基-COOH、磺基-SO3H、三(C1-C3)烷基铵(alkylammonio)和(C1-C3)烷基咪唑鎓(imidazolio)的基团取代;
-吡咯烷基,其任选被选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代;
-哌啶基,其任选被选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代;
·n表示0-3之间的整数,包括0和3;
·R2和R3相同或不同,如R4和R5所定义;
应当理解,当X和/或R2和/或R3和/或R4和/或R5包含阳离子基团时,通过化妆品上可接受的(cosmetically acceptable)阴离子抗衡离子或化妆品上可接受的阴离子抗衡离子的混合物实现式(I)的化合物的电中性。所述阴离子抗衡离子如氯离子(chlorides)、溴离子(bromides)和硫酸根(sulphates)。
本发明的另一个主题是从氯化偶氮甲碱染料的无色还原前体开始的染色方法,所述还原前体一旦被氧化,就产生如上定义的式(I)化合物。这些前体对应式(II)的化合物、其有机酸盐或无机酸盐、其几何异构体、其互变异构体和其溶剂合物(如水合物):
在式(II)中,R1、R2、R3、X和n如上所定义;
应当理解:
-当X和/或R2和/或R3和/或R4和/或R5包含阳离子基团时,通过化妆品上可接受的阴离子抗衡离子或化妆品上可接受的阴离子抗衡离子的混合物实现式(II)的化合物的电中性。所述阴离子抗衡离子如氯离子、溴离子和硫酸根。
本发明的另一个主题是如上所定义的式(I)或(II)的化合物。
本发明的另一个主题是用于将角蛋白纤维染色的染色组合物,其在化妆品介质中包含至少一种如上所定义的式(I)或(II)的化合物。
式(I)的直接染料使得有可能克服以前常规使用的直接染料的缺陷,并通过直接染色获得染色,所述染色对光、坏气候、洗涤操作、排汗和摩擦作用具有非常好的耐受性。它们对氧化剂(如过氧化氢水溶液)的良好稳定性也使得有可能将它们用于增亮直接染色方法。
此外,已发现从式(II)的2-氯-3-氨基-6-甲基苯酚衍生物得到的还原形式的偶氮甲碱衍生物在氧化条件下使用时,也可得到对光、坏气候、洗涤操作、排汗和摩擦作用具有非常好的耐受性的着色。
在本发明的含义中,除非另有说明:
-“有机酸盐或无机酸盐”选自例如衍生自以下酸的盐:i)盐酸HCl;ii)氢溴酸HBr;iii)硫酸H2SO4;iv)烷基磺酸:烷基-S(O)2OH,如甲磺酸和乙磺酸;v)芳基磺酸:芳基-S(O)2OH,如苯磺酸和甲苯磺酸;vi)柠檬酸;vii)琥珀酸;viii)酒石酸;ix)乳酸;x)烷氧基亚磺酸:烷基-O-S(O)OH,如甲氧基亚磺酸和乙氧基亚磺酸;xi)芳氧基亚磺酸,如甲苯氧基亚磺酸和苯氧基亚磺酸;xii)磷酸H3PO4;xiii)乙酸CH3C(O)OH;xiv)三氟甲磺酸CF3SO3H;以及xv)四氟硼酸HBF4;
-“阴离子抗衡离子”是与染料的阳离子电荷缔合的阴离子或阴离子基团;更具体地,所述阴离子抗衡离子选自:i)卤素离子(halide),如氯离子或溴离子;ii)硝酸根;iii)磺酸根,包括C1-C6烷基磺酸根(烷基-S(O)2O-),如甲磺酸根(methanesulfonate或mesylate)和乙磺酸根;iv)芳基磺酸根(芳基-S(O)2O-),如苯磺酸根和甲苯磺酸根(toluenesulfonate或tosylate);v)柠檬酸根;vi)琥珀酸根;vii)酒石酸根;viii)乳酸根;ix)烷基硫酸根(烷基-O-S(O)O-),如甲基硫酸根和乙基硫酸根;x)芳基硫酸根(芳基-O-S(O)O-),如苯硫酸根和甲苯硫酸根;xi)烷氧基硫酸根(烷基-O-S(O)2O-),如甲氧基硫酸根和乙氧基硫酸根;xii)芳氧基硫酸根(芳基-O-S(O)2O-);xiii)磷酸根;xiv)乙酸根;xv)三氟甲磺酸根;以及xvi)硼酸根,如四氟硼酸根;
-“烷基”是包含1-6个碳原子(尤其1-3个碳原子)的饱和直链或支化烃基,如甲基或乙基;
-“烷氧基”是“烷基-氧基”(烷基-O-基团),其中烷基部分如上所定义;
-跟随“任选被……取代的”后的烷基、烷氧基或杂环烷基指所述基团可有一个或多个氢原子被一个或多个所讨论的取代基(尤其一个或两个所讨论的取代基)置换。
本发明的主题是式(I)的直接染料或式(II)的染色前体。
本发明的具体实施方式涉及式(I)或(II)的化合物,其中n的值为0。
根据本发明的另一个具体实施方式,本发明组合物中存在的一种或多种式(I)或(II)的化合物是这样的:其中n的值为1,R1表示(C1-C3)烷基,如甲基。
一种另选形式(alternative form)涉及式(I)或(II)的化合物,其中X表示羟基。
本发明的另一种另选形式涉及式(I)或(II)的化合物,其中X表示-NR4R5基团,其中R4和R5各自独立地表示:i)氢原子;或ii)C1-C5烷基,其任选被一个或多个选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、氨基羰基、羧基-COOH、磺基-SO3H、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代。更具体地,X表示选自以下的基团:i)二(C1-C3)烷基氨基;ii)二[羟基(C1-C3)烷基]氨基;iii)(C1-C3)烷基咪唑鎓(C1-C3)烷基氨基;iv)[N-(C1-C3)烷基,N-(C1-C3)烷基咪唑鎓(C1-C3)烷基]氨基;v)三(C1-C3)烷基铵(C1-C5)烷基氨基和vi)二[三(C1-C3)烷基铵(C1-C5)烷基]氨基。
根据本发明的另一个具体实施方式,式(I)或(II)的化合物是这样的:其中X表示吡咯烷基,其任选被三(C1-C3)烷基铵或(C1-C3)烷基咪唑鎓基团取代。更具体地,X表示1-吡咯烷基(pyrrolidino),其任选被三(C1-C3)烷基铵或(C1-C3)烷基咪唑鎓基团取代。
根据一个具体实施方式,式(I)或(II)的化合物是这样的:其中NR2R3表示氨基NH2基团。
作为本发明组合物中存在的式(I)或(II)的化合物的例子,可提及以下染料(1a)-(1t)和前体(2a)-(2p)及其有机酸盐或无机酸盐、其几何异构体、其互变异构体和其溶剂合物(如水合物):
式(I)的染料:
式(II)的前体:
其中An-可以相同或不同,表示阴离子抗衡离子(如卤素离子);An-尤其表示氯离子。
更具体地,组合物中存在的染料选自前述染料(1a)、(1b)、(1c)、(1d)、(1e)、(1f)、(1g)和(1i)及其有机酸盐或无机酸盐、其几何异构体、其互变异构体和其溶剂合物(如水合物)。根据本发明的另一个具体形式,优选的化合物是化合物(1m)和(1p)。
按照以下通用合成路线制备本发明式(I)或(II)的化合物:
1-获得对应于式(I)的化合物:
总的来说,通过以下方式获得对应于式(I)的化合物:在氧化剂存在下,优选在碱性介质中,使2-氯-3-氨基-6-甲基苯酚衍生物与对氨基苯酚衍生物(X=OH)或对苯二胺衍生物(X=NR4R5)反应。所用的碱优选为氨水或氢氧化钠水溶液,氧化剂优选选自过氧化氢水溶液、铁氰化钾、空气、过硫酸铵和氧化锰。
类似的合成方法描述于专利FR 2 234 277、FR 2 047 932、FR 2 106 661和FR 2 121 101中。
2-获得对应于式(II)的化合物:
总的来说,通过使式(I)化合物与还原剂反应获得对应于式(II)的化合物。该优选的还原剂是连二亚硫酸钠(sodium hydrosulfite)。
类似的合成方法描述于专利FR 2 056 799、FR 2 047 932、FR 2 165 965和FR 2 262 023中。
本发明的另一个主题涉及用于将角蛋白纤维(尤其人的角蛋白纤维,如头发)染色的染色组合物,其在化妆品介质中包含式(I)的直接染料或式(II)的染色前体。
本发明所用的染色组合物一般包含一定量的式(I)染料或式(II)前体,相对于组合物的总重量计,其占0.001重量%-30重量%。优选地,相对于组合物的总重量计,该量为0.005重量%-10重量%,更优选0.01重量%-6重量%。
包含式(I)染料或优选包含式(II)前体的染色组合物还可包含氧化剂,如过氧化氢、过氧化氢脲、碱金属溴酸盐、过酸盐、过酸和氧化酶(oxidase enzymes)。
染色组合物可另外含有不同于式(I)或(II)的那些的另外直接染料。这些直接染料例如选自中性、酸性或阳离子硝基苯直接染料;中性、酸性或阳离子偶氮直接染料;四氮杂五甲炔染料(tetraazapentamethine dyes);中性、酸性或阳离子醌(尤其蒽醌)染料,吖嗪直接染料,三芳基甲烷直接染料,靛胺(indoamine)直接染料和天然直接染料。
可以非限制性方式提及的硝基苯直接染料中有以下化合物:
1,4-二氨基-2-硝基苯、1-氨基-2-硝基-4-(β-羟乙基氨基)苯、1-氨基-2-硝基-4-[二(β-羟乙基)氨基]苯、1,4-二(β-羟乙基氨基)-2-硝基苯、1-(β-羟乙基氨基)-2-硝基-4-[二(β-羟乙基)]氨基苯、1-(β-羟乙基氨基)-2-硝基-4-氨基苯、1-(β-羟乙基氨基)-2-硝基-4-[(乙基)(β-羟乙基)氨基]苯、1-氨基-3-甲基-4-(β-羟乙基氨基)-6-硝基苯、1-氨基-2-硝基-4-(β-羟乙基氨基)-5-氯苯、1,2-二氨基-4-硝基苯、1-氨基-2-(β-羟乙基氨基)-5-硝基苯、1,2-二(β-羟乙基氨基)-4-硝基苯、1-氨基-2-[三(羟甲基)甲基氨基]-5-硝基苯、1-羟基-2-氨基-5-硝基苯、1-羟基-2-氨基-4-硝基苯、1-羟基-3-硝基-4-氨基苯、1-羟基-2-氨基-4,6-二硝基苯、1-(β-羟乙基氧基)-2-(β-羟乙基氨基)-5-硝基苯、1-甲氧基-2-(β-羟乙基氨基)-5-硝基苯、1-(β-羟乙基氧基-3-甲基氨基)-4-硝基苯、1-(β,γ-二羟基丙氧基)-3-甲基氨基-4-硝基苯、1-(β-羟乙基氨基)-4-(β,γ-二羟基丙氧基)-2-硝基苯、1-(β,γ-二羟基丙基氨基)-4-三氟甲基-2-硝基苯、1-(β-羟乙基氨基)-4-三氟甲基-2-硝基苯、1-(β-羟乙基氨基)-3-甲基-2-硝基苯、1-(β-氨基乙基氨基)-5-甲氧基-2-硝基苯、1-羟基-2-氯-6-乙基氨基-4-硝基苯、1-羟基-2-氯-6-氨基-4-硝基苯、1-羟基-6-[二(β-羟乙基)氨基]-3-硝基苯、1-(β-羟乙基氨基)-2-硝基苯或1-羟基-4-(β-羟乙基氨基)-3-硝基苯。
偶氮直接染料中,可提及专利申请WO 95/15144、WO-95/01772和EP-714 954中描述的阳离子偶氮染料,所述专利申请的内容构成本发明的组成部分。
在这些化合物中,可特别提及以下染料:氯化1,3-二甲基-2-[[4-(二甲基氨基)苯基]偶氮]-1H-咪唑鎓、氯化1,3-二甲基-2-[(4-氨基苯基)偶氮]-1H-咪唑鎓或者1-甲基-4-[(甲基苯基亚肼基)甲基]吡啶鎓甲基硫酸盐。
在偶氮直接染料中,还可提及《国际颜色索引》(Colour Index International,第3版)中描述的以下染料:
分散红17、酸性黄9、酸性黑1、碱性红22、碱性红76、碱性黄57、碱性棕16、酸性黄36、酸性橙7、酸性红33、酸性红35、碱性棕17、酸性黄23、酸性橙24和分散黑9。
还可提及1-(4’-氨基二苯基偶氮)-2-甲基-4-[二(β-羟乙基)氨基]苯和4-羟基-3-(2-甲氧基苯基偶氮)-1-萘磺酸。
在醌直接染料中,可提及以下染料:
分散红15、溶剂紫13、酸性紫43、分散紫1、分散紫4、分散蓝1、分散紫8、分散蓝3、分散红11、酸性蓝62、分散蓝7、碱性蓝22、分散紫15和碱性蓝99,以及以下化合物:1-(N-甲基吗啉鎓丙基氨基)-4-羟基蒽醌、1-氨基丙基氨基-4-甲基氨基蒽醌、1-氨基丙基氨基蒽醌、5-(β-羟乙基)-1,4-二氨基蒽醌、2-氨基乙基氨基蒽醌和1,4-二(β,γ-二羟基丙基氨基)蒽醌。
在吖嗪染料中,可提及以下化合物:
-碱性蓝17和碱性红2。
在三芳基甲烷染料中,可提及以下化合物:碱性绿1、酸性蓝9、碱性紫3、碱性紫14、碱性蓝7、酸性紫49、碱性蓝26和酸性蓝7。
在靛胺染料中,可提及以下化合物:
-2-(β-羟乙基氨基-5-[二(β-4’-羟乙基)氨基]苯胺基-1,4-苯醌;-2-(β-羟乙基氨基-5-(2’-甲氧基-4’-氨基苯胺基)-1,4-苯醌;-3-N-(2’-氯-4’-羟基)苯基乙酰氨基-6-甲氧基-1,4-苯醌亚胺;-3-N-(3’-氯-4’-甲基氨基)苯基脲基-6-甲基-1,4-苯醌亚胺;-3-[4’-N-(乙基,氨基甲酰甲基)-氨基]苯基脲基-6-甲基-1,4-苯醌亚胺。
天然直接染料中,可提及指甲花醌、胡桃醌、茜素、紫红素、胭脂红酸、胭脂酮酸、红棓酚(purpurogallin)、原儿茶醛(protocatechaldehyde)、靛蓝、靛红、姜黄色素、小刺青霉素(spinulosin)和芹菜定(apigenidine)。也可能使用包含这些天然染料的提取物或煎煮剂,尤其基于指甲花的糊剂(cataplasms)或提取物。
染色组合物可包含常规用于角蛋白纤维染色的一种或多种氧化显色碱和/或一种或多种成色剂。
在氧化显色碱中,可提及对苯二胺、二苯基亚烷基二胺、对氨基苯酚、二-对氨基苯酚、邻氨基苯酚、杂环碱及其加成盐。
在成色剂中,可特别提及间苯二胺、间氨基苯酚、间二苯酚(meta-diphenols)、萘成色剂和杂环成色剂、及其加成盐。
相对于染色组合物的总重量计,一种或多种成色剂各自的存在量一般为0.001重量%-10重量%,优选0.005重量%-6重量%。
相对于染色组合物的总重量计,存在于染色组合物中的一种或多种氧化显色碱各自的存在量一般约为0.001重量%-10重量%,优选0.005重量%-6重量%。
一般地,可用于本发明上下文中的氧化显色碱与成色剂的加成盐特别选自与酸的加成盐,如盐酸盐、氢溴酸盐、硫酸盐、柠檬酸盐、琥珀酸盐、酒石酸盐、乳酸盐、甲苯磺酸盐、苯磺酸盐、磷酸盐和乙酸盐;以及与碱的加成盐,如碱金属氢氧化物(如氢氧化钠或氢氧化钾)、氨、胺或烷醇胺。
适用于染色的介质(也称为染料载体)是化妆品介质,一般包含水或者水与至少一种有机溶剂的混合物。可提及的有机溶剂例如为低级C1-C4烷醇(如乙醇和异丙醇)、多元醇和多元醇醚(如2-丁氧基乙醇、丙二醇、丙二醇单甲醚、二甘醇单甲醚和二甘醇单甲醚)、芳族醇(如苄醇或苯氧基乙醇)、以及它们的混合物。
若存在溶剂,则其优选以以下比例存在:相对于染色组合物的总重量计,优选约1重量%-约50重量%,更优选约5重量%-约40重量%。
染色组合物还可包含常规用于染发组合物中的各种辅助剂,如阴离子、阳离子、非离子、两性或两性离子表面活性剂或其混合物;阴离子、阳离子或非离子、两性或两性离子聚合物或其混合物;无机或有机增稠剂,尤其阴离子、阳离子、非离子和两性聚合物缔合性增稠剂;抗氧化剂;渗透剂;螯合剂;香料;缓冲剂;分散剂;调理剂(例如挥发性或非挥发性的改性或未改性硅氧烷,如氨基硅氧烷);成膜剂;神经酰胺;防腐剂;遮光剂或导电聚合物。
相对于组合物重量计,上述辅助剂各自的存在量一般为0.01重量%-20重量%。
当然,本领域技术人员将小心选择这种或这些任选的另外化合物,以使本发明染色组合物固有的有利性质不受到或基本不受到所设想的一种或多种添加物的不利影响。
染色组合物的pH一般大约为3-14,可通过常用于角蛋白纤维染色的酸化剂或碱化剂或者使用常规缓冲体系将其调节到所需值。
根据本发明的一个具体形式,当染色组合物包含至少一种式(I)染料时,组合物的pH为6-11。根据本发明的另一个具体形式,当组合物包含至少一种式(II)染色前体时,组合物的pH为6-11。
在酸化剂中,可提及的例子为无机酸或有机酸,如盐酸、正磷酸、硫酸、羧酸(如乙酸)、酒石酸、柠檬酸或乳酸或磺酸。
在碱化剂中,可提及的例子为氨、碱金属碳酸盐、烷醇胺(如单乙醇胺、二乙醇胺和三乙醇胺)及其衍生物、氢氧化钠、氢氧化钾和下式(γ)的化合物:
其中Wa是任选被羟基或C1-C4烷基取代的亚丙基残基;Ra1、Ra2、Ra3和Ra4可相同或不同,表示氢原子、C1-C4烷基或C1-C4羟烷基。
染色组合物可以各种形式提供,如液体形式、乳膏形式或凝胶形式,或者适用于将角蛋白纤维(尤其毛发)染色的任何其他形式。
本发明的另一个主题是将角蛋白纤维(尤其毛发)染色的方法,其包括在存在或不存在氧化剂的情况下,将染色组合物施涂到角蛋白材料上,所述染色组合物在化妆品介质中包含至少一种如上所定义的式(I)的偶氮甲碱染料或式(II)的染色前体。
保留一定时间(a leave-in time)后,冲洗角蛋白纤维,以显露被染色的纤维。保留时间一般约为3-50分钟,优选约5-40分钟。
一般在室温下进行本发明染色组合物的施涂,然而,可在20-80℃的温度下进行。
以下实施例用于阐述本发明,但非限制本发明。以下实施例中的染料通过标准光谱学和光谱测量方法(spectroscopic and spectrometric methods)充分表征。
实施例
合成实施例
实施例1:3-氨基-2-氯-4-(4-羟基苯基亚氨基)-6-甲基环己-2,5-二烯酮1
(化合物(1a))的合成
将9.7g(0.05mol)3-氨基-2-氯-6-甲基苯酚溶解在250ml水中,并加入到锥形烧瓶中的包含5.45g(0.05mol)对氨基苯酚、150ml水和80ml 20%的氢氧化铵水溶液的溶液中。
然后,加入溶解在150ml水中的32.9g(0.1mol)铁氰化钾的溶液,环境温度下搅拌反应介质2小时。
滤出所形成的固体,用水洗涤,然后从乙醇/水的75/25混合物中重结晶,得到4.4g式(1a)的3-氨基-2-氯-4-(4-羟基苯基亚氨基)-6-甲基环己-2,5-二烯酮。
实施例2:3-氨基-4-(4-氨基苯基亚氨基)-2-氯-6-甲基环己-2,5-二烯酮2
(化合物(1b))的合成
在锥形烧瓶中,将9g(0.05mol)二盐酸对苯二胺在250ml水中的溶液与9.7g(0.05mol)3-氨基-2-氯-6-甲基苯酚在250ml水和80ml的20%氢氧化铵水溶液中的溶液混合。然后,分批加入32.9g(0.1mol)铁氰化钾,用150ml水稀释反应介质。环境温度下搅拌12小时后,滤出所形成的固体,然后用水洗涤。
然后,通过二氧化硅柱色谱(chromatography on a silica column)(洗脱液:二氯甲烷-二氯甲烷/甲醇:90/10)纯化所得粗产物,得到2.1g式(1b)的3-氨基-4-(4-氨基苯基亚氨基)-2-氯-6-甲基环己-2,5-二烯酮。
实施例3:3-氨基-4-(4-氨基-甲基苯基亚氨基)-2-氯-6-甲基环己-2,5-二
烯酮3(式(1c)的化合物)的合成
将9.7g(0.05mol)3-氨基-2-氯-6-甲基苯酚溶解在250ml水中,并加入到锥形烧瓶中的包含9.75g(0.05mol)对甲苯二胺、250ml水和40ml 20%的氢氧化铵水溶液的溶液中。
然后,加入32.9g(0.1mol)铁氰化钾溶解在150ml水中的溶液,环境温度下搅拌反应介质3小时20分钟。
滤出所形成的固体,用水洗涤,然后通过二氧化硅柱色谱(洗脱液:二氯甲烷/甲醇:99/1)纯化,得到2.98g式(1c)的3-氨基-4-(4-氨基-甲基苯基亚氨基)-2-氯-6-甲基环己-2,5-二烯酮。
实施例4:3-氨基-4-[(4-氨基苯基)氨基]-2-氯-6-甲基苯酚(2b)的合成
将10mg(0.04mol)(4Z)-3-氨基-4-[(4-氨基苯基)亚氨基]-2-氯-6-甲基环己-2,5-二烯-1-酮加入到包含连二亚硫酸钠(16mg)的甲醇(500μl)溶液和5μL氢氧化钠水溶液的溶液中。搅拌反应介质,然后按照常用程序后处理并表征该溶液,得到3-氨基-4-[(4-氨基苯基)氨基]-2-氯-6-甲基苯酚(2b)。
实施例5:3-氨基-4-[(4-氨基-2-甲基苯基)氨基]-2-氯-6-甲基苯酚/3-氨基
-4-[(4-氨基-3-甲基苯基)氨基]-2-氯-6-甲基苯酚(2c)的合成
将10mg(0.04mol)3-氨基-4-[(4-氨基-2-甲基苯基)亚氨基]-2-氯-6-甲基环己-2,5-二烯-1-酮和3-氨基-4-[(4-氨基-3-甲基苯基)亚氨基]-2-氯-6-甲基环己-2,5-二烯-1-酮加入到包含连二亚硫酸钠(16mg)的甲醇(500μl)溶液和5μl氢氧化钠水溶液的溶液中。搅拌反应介质,然后根据常用程序后处理并表征该溶液,得到3-氨基-4-[(4-氨基-2-甲基苯基)氨基]-2-氯-6-甲基苯酚/3-氨基-4-[(4-氨基-3-甲基苯基)氨基]-2-氯-6-甲基苯酚(2c)。
实施例6:3-氨基-2-氯-4-[(4-羟基苯基)氨基]-6-甲基苯酚(2a)的合成
将10mg(0.04mol)3-氨基-2-氯-4-[(4-羟基苯基)亚氨基]-6-甲基环己-2,5-二烯-1-酮加入到包含连二亚硫酸钠(16mg)的甲醇(500μl)溶液和5μl氢氧化钠水溶液的溶液中。搅拌反应介质,然后根据常用程序后处理并表征该溶液,得到3-氨基-2-氯-4-[(4-羟基苯基)氨基]-6-甲基苯酚(2a)。
实施例7:3-氨基-2-氯-4-({4-[乙基(2-羟乙基)氨基]苯基}亚氨基)-6-甲基
环己-2,5-二烯-1-酮(1k)的合成
将1.94g盐酸3-氨基-2-氯-6-甲基苯酚加入到2.53g盐酸2-[(4-氨基苯基)(乙基)氨基]乙醇在20ml水和10ml乙醇中的溶液中。用20%氢氧化铵水溶液将pH调节到9.5。随后加入36ml 9%过氧化氢水溶液,在环境温度下搅拌反应介质4小时30分钟。滤出固体形式,用水洗涤,得到2.44g 3-氨基-2-氯-4-({4-[乙基(2-羟乙基)氨基]苯基}亚氨基)-6-甲基环己-2,5-二烯-1-酮(1k)。
实施例8:3-氨基-2-氯-4-{[4-(3-羟基吡咯烷-1-基)苯基]亚氨基}-6-甲基
环己-2,5-二烯-1-酮(1l)的合成
将1.94g盐酸3-氨基-2-氯-6-甲基苯酚加入到2.51g二盐酸1-(4-氨基苯基)吡咯烷-3-醇在20ml水和20ml乙醇中的溶液中。用20%氢氧化铵将pH调节至9.5,然后加入18ml 9%过氧化氢水溶液。在环境温度下将混合物搅拌8小时,然后滤出形成的沉淀。从而得到2.79g 3-氨基-2-氯-4-{[4-(3-羟基吡咯烷-1-基)苯基]亚氨基}-6-甲基环己-2,5-二烯-1-酮(1l)。
实施例9:3-氨基-2-氯-6-甲基-4-[(4-吡咯烷-1-基苯基)亚氨基]环己-2,5-
二烯-1-酮(1m)的合成
将1.94g盐酸3-氨基-2-氯-6-甲基苯酚加入到2.35g二盐酸4-(吡咯烷-1-基)苯胺在15ml水和15ml乙醇中的溶液中。用20%氢氧化铵将pH调节至9.5,然后加入18ml 9%过氧化氢水溶液。在环境温度下将混合物搅拌4小时,然后滤出形成的沉淀。从而得到1.7g 3-氨基-2-氯-6-甲基-4-[(4-吡咯烷-1-基苯基)亚氨基]环己-2,5-二烯-1-酮(1m)。
实施例10:3-氨基-2-氯-6-甲基-4-{[4-(甲基氨基)苯基]亚氨基}环己-2,5-
二烯-1-酮(1n)的合成
用20%氢氧化铵水溶液使2g二盐酸N-甲基苯-1,4-二胺、2g盐酸3-氨基-2-氯-6-甲基苯酚、20ml水、20ml乙醇和7.6ml 9%过氧化氢水溶液的混合物达到pH 9.5,并在环境温度下搅拌5小时,得到2.5g 3-氨基-2-氯-6-甲基-4-{[4-(甲基氨基)苯基]亚氨基}环己-2,5-二烯-1-酮(1n)。
实施例11:3-氨基-2-氯-4-{[4-(二戊基氨基)苯基]亚氨基}-6-甲基环己
-2,5-二烯-1-酮(1o)的合成
将0.48g盐酸3-氨基-2-氯-6-甲基苯酚加入到0.8g二盐酸N,N-二戊基苯-1,4-二胺在5ml水和40ml乙醇中的溶液中。用20%氢氧化铵将pH调节至9.5,然后加入1.7ml 9%过氧化氢水溶液。在环境温度下将混合物搅拌5小时,然后滤出形成的沉淀。从而得到0.72g 3-氨基-2-氯-4-{[4-(二戊基氨基)苯基]亚氨基}-6-甲基环己-2,5-二烯-1-酮(1o)。
实施例12:3-氨基-4-({4-[二(2-羟乙基)氨基]苯基}亚氨基)-2-氯-6-甲基
环己-2,5-二烯-1-酮(1p)的合成
将1.69g盐酸3-氨基-2-氯-6-甲基苯酚加入到2.715g硫酸2,2′-[(4-氨基苯基)亚氨基]二乙醇在32ml水和32ml乙醇中的溶液中。用20%氢氧化铵将pH调节至9.5,然后加入31.5ml 9%过氧化氢水溶液。在环境温度下将混合物搅拌6小时,然后滤出形成的沉淀。从而得到1.68g 3-氨基-4-({4-[二(2-羟乙基)氨基]苯基}亚氨基)-2-氯-6-甲基环己-2,5-二烯-1-酮(1p)。
实施例13:3-氨基-4-[(4-氨基-2-甲基苯基)亚氨基]-2-氯-6-甲基环己
-2,5-二烯-1-酮与3-氨基-4-[(4-氨基-3-甲基苯基)亚氨基]-2-氯-6-甲基环己
-2,5-二烯-1-酮异构体的混合物(1q)的合成
将9.7g(0.05mol)3-氨基-2-氯-6-甲基苯酚溶解在250ml水中,并加入到锥形烧瓶中的包含9.75g(0.05mol)二盐酸2-甲基苯-1,4-二胺、250ml水和40ml 20%氢氧化铵水溶液的溶液中。
随后,滴加溶解于150ml水中的32.9g(0.1ml)铁氰化钾溶液,在环境温度下搅拌反应介质2小时。
滤出所形成的固体,用水洗涤,干燥,然后通过二氧化硅色谱(洗脱液:二氯甲烷99/甲醇1)纯化。从而得到2.98g 3-氨基-4-[(4-氨基-2-甲基苯基)亚氨基]-2-氯-6-甲基环己-2,5-二烯-1-酮与3-氨基-4-[(4-氨基-3-甲基苯基)亚氨基]-2-氯-6-甲基环己-2,5-二烯-1-酮异构体的混合物(1q)。
实施例14:氯化1-[1-(4-{[2-氨基-3-氯-5-甲基-4-氧代环己-2,5-二烯-1-
亚基]氨基}苯基)吡咯烷-3-基]-3-甲基-1H-咪唑-3-鎓(1r)的合成
称取315mg盐酸1-[1-(4-氨基苯基)吡咯烷-3-基]-3-甲基-1H-咪唑-3-鎓氯化物和194.1mg盐酸3-氨基-2-氯-6-甲基苯酚,置于烧瓶中,加入1ml水,用20%氢氧化铵水溶液将pH调节至9.5。
滴加0.5ml 30%过氧化氢水溶液。反应放热,温度升至60℃。
将混合物搅拌18小时。滤出沉淀,用丙酮冲洗。第二天早晨,滤液中形成第二份沉淀,将其滤出。从而得到81mg氯化1-[1-(4-{[2-氨基-3-氯-5-甲基-4-氧代环己-2,5-二烯-1-亚基]氨基}苯基)吡咯烷-3-基]-3-甲基-1H-咪唑-3-鎓(1r)。
实施例15:氯化1-(4-{[2-氨基-3-氯-5-甲基-4-氧代环己-2,5-二烯-1-亚基]
氨基}苯基)-N,N,N-三甲基吡咯烷-3-铵(1t)的合成
称取292.5mg盐酸氯化1-(4-氨基苯基)-N,N,N-三甲基吡咯烷-3-铵和194.1mg盐酸3-氨基-2-氯-6-甲基苯酚,置于烧瓶中,加入1ml水,用20%氢氧化铵水溶液将pH调节至9.5。滴加1.1ml 30%过氧化氢水溶液。将混合物搅拌24小时。滤出沉淀,用丙酮冲洗。从而得到80mg氯化1-(4-{[2-氨基-3-氯-5-甲基-4-氧代环己-2,5-二烯-1-亚基]氨基}苯基)-N,N,N-三甲基吡咯烷-3-铵(1t)。
染色实施例
在中性介质中染色
从上面合成的染料化合物(1b)和化合物(1c)制备以下染色组合物(A)和(B)。
(*):染色载体(1)pH=7,该染色载体由以下物质构成:
96°乙醇 | 20.8g |
二亚乙基三胺五乙酸五钠盐,为40%水溶液 | 0.48g A.M |
C8-C10烷基多聚葡糖苷,为60%水溶液 | 3.6g A.M |
苄醇 | 2.0g |
含8个环氧乙烷单元的聚乙二醇 | 3.0g |
Na2HPO4 | 0.28g |
KH2PO4 | 0.46g |
将组合物(A)和(B)施涂于几绺含90%白头发的白发上。30分钟停留时间后,冲洗所述发绺,用标准洗发剂洗涤,再次冲洗,然后干燥。
获得的色调在下表中给出:
组合物 | (A) | (B) |
处理之后观察到的色调 | 紫红 | 鲜紫 |
在碱性介质中染色
分别从化合物(1a)-(1c)制备以下染色组合物(C)-(E)。
(*):染色载体(2)pH=9.5,该染色载体由以下物质构成:
96°乙醇 | 20.8g |
二亚乙基三胺五乙酸五钠盐,为40%水溶液 | 0.48g A.M |
C8-C10烷基聚葡糖苷,为60%水溶液 | 3.6g A.M |
苄醇 | 2.0g |
包含8个环氧乙烷单元的聚乙二醇 | 3.0g |
NH4Cl | 4.32g |
包含20%NH3的氨水 | 2.94g |
将组合物(C)-(E)施涂于几绺含90%白头发的白发上。30分钟停留时间后,冲洗所述发绺,用标准洗发剂洗涤,再次冲洗,然后干燥。
获得的色调在下表中给出:
组合物 | (C) | (D) | (E) |
处理之后观察到的色调 | 淡橙色 | 深红色 | 紫色 |
Claims (17)
1.式(I)或式(II)的化合物、其有机酸盐或无机酸盐、其几何异构体、其互变异构体和其溶剂合物如水合物:
在式(I)或(II)中:
·R1表示:
-氯原子;
-(C1-C3)烷基,其任选被一个或多个羟基取代;
-(C1-C3)烷氧基,其任选被一个或多个羟基取代;
·X表示:
-羟基;
--NR4R5基团,其中R4和R5各自独立地表示:
i)氢原子;
ii)C1-C5烷基,其任选被一个或多个选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、氨基羰基、羧基-COOH、磺基-SO3H、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代;
-吡咯烷基,其任选被选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代;
-哌啶基,其任选被选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代;
·n表示0-3之间的整数,包括0和3;
·R2和R3相同或不同,如R4和R5所定义;
应当理解,当X和/或R2和/或R3和/或R4和/或R5包含阳离子基团时,通过化妆品上可接受的阴离子抗衡离子或化妆品上可接受的阴离子抗衡离子的混合物实现式(I)或(II)的化合物的电中性。
2.式(I)或(II)的化合物,其中n的值为1,R1表示(C1-C3)烷基。
3.式(I)或(II)的化合物,其中n是0。
4.根据前述权利要求中任一项所述式(I)或(II)的化合物,其中X表示羟基。
5.根据权利要求1-3中任一项所述式(I)或(II)的化合物,其中X表示-NR4R5基团,R4和R5各自独立地表示:i)氢原子;或ii)C1-C5烷基,其任选被一个或多个选自羟基、(C1-C3)烷氧基、氨基、(C1-C3)烷基氨基、二(C1-C3)烷基氨基、氨基羰基、羧基-COOH、磺基-SO3H、三(C1-C3)烷基铵和(C1-C3)烷基咪唑鎓的基团取代。
6.根据权利要求1-3中任一项所述式(I)或(II)的化合物,其中X表示吡咯烷基,其任选被三(C1-C3)烷基铵或(C1-C3)烷基咪唑鎓取代。
8.用于将角蛋白纤维染色的染色组合物,其在化妆品介质中包含至少一种前述权利要求中任一项所定义的式(I)或(II)的化合物。
9.根据前一项权利要求所述组合物,其中相对于组合物的总重量计,式(I)或(II)的化合物的存在量为0.001重量%-30重量%。
10.根据权利要求8或9所述组合物,其中当组合物包含至少一种式(I)的化合物时,组合物的pH为6-11。
11.根据权利要求8或9所述组合物,其中当组合物包含至少一种式(II)的化合物时,组合物的pH为6-11。
12.根据权利要求8-11中任一项所述组合物,其另外包含至少一种氧化剂。
13.根据前一项权利要求所述组合物,其中所述氧化剂选自过氧化氢、过氧化氢脲、碱金属溴酸盐、过酸盐、过酸和氧化酶。
14.根据权利要求8-13中任一项所述组合物,其另外包含选自以下的至少一种不同于式(I)或(II)的化合物的直接染料:中性、酸性或阳离子硝基苯直接染料;中性、酸性或阳离子偶氮直接染料;四氮杂五甲炔染料;中性、酸性或阳离子醌,尤其蒽醌染料;吖嗪直接染料;三芳基甲烷直接染料;靛胺直接染料以及天然直接染料。
15.根据权利要求8-14中任一项所述组合物,其另外包含至少一种选自以下的辅剂:阴离子、阳离子、非离子、两性和两性离子表面活性剂或其混合物;阴离子、阳离子、非离子、两性或两性离子聚合物或其混合物;无机或有机增稠剂;抗氧化剂;渗透剂;螯合剂;香料;缓冲剂;分散剂;调理剂;成膜剂;神经酰胺;防腐剂;遮光剂和导电聚合物。
16.将角蛋白纤维染色的方法,其中将前述权利要求中任一项所述的适当染料组合物施涂到材料上。
17.权利要求1-7中任一项所定义的式(I)或(II)的化合物用于将角蛋白纤维染色的用途。
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0759848 | 2007-12-14 | ||
FR0759848A FR2925056B1 (fr) | 2007-12-14 | 2007-12-14 | Colorants directs azomethiniques ou precurseurs reduits de ces colorants obtenus a partir du 2-chloro-3-amino-6-methylphenol, procede de coloration capillaire a partir de ces colorants et precurseurs |
US627908P | 2008-01-04 | 2008-01-04 | |
US61/006,279 | 2008-01-04 | ||
US61/006279 | 2008-01-04 | ||
PCT/EP2008/067152 WO2009077393A1 (en) | 2007-12-14 | 2008-12-09 | Azomethine direct dyes or reduced precursors of these dyes obtained from 2-chloro-3-amino-6-methylphenol, and hair dyeing method starting from these dyes and precursors |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101945640A true CN101945640A (zh) | 2011-01-12 |
CN101945640B CN101945640B (zh) | 2013-08-28 |
Family
ID=39689019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2008801271696A Expired - Fee Related CN101945640B (zh) | 2007-12-14 | 2008-12-09 | 从2-氯-3-氨基-6-甲基苯酚获得的偶氮甲碱直接染料或这些染料的还原前体、以及从这些染料或前体开始的染发方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8083809B2 (zh) |
EP (1) | EP2229140B1 (zh) |
CN (1) | CN101945640B (zh) |
AT (1) | ATE518518T1 (zh) |
BR (1) | BRPI0819372A2 (zh) |
FR (1) | FR2925056B1 (zh) |
WO (1) | WO2009077393A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103998417A (zh) * | 2011-12-13 | 2014-08-20 | 欧莱雅 | 特定的醌直接染料、包含至少一种此染料的染料组合物、其实施方法及其用途 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2968947B1 (fr) * | 2010-12-20 | 2013-04-26 | Oreal | Composition de coloration comprenant de l'alcool benzylique, un monoalcool et un colorant azomethinique particulier |
US8801808B2 (en) | 2010-12-20 | 2014-08-12 | L'oreal | Dye composition comprising benzyl alcohol, a monoalcohol and a particular direct dye |
FR2983710B1 (fr) * | 2011-12-13 | 2014-01-10 | Oreal | Colorants directs azomethiniques particuliers, composition tinctoriale comprenant au moins un tel colorant, procede de mise en oeuvre et utilisation |
FR2983857B1 (fr) * | 2011-12-13 | 2014-02-14 | Oreal | Colorants directs azomethiniques tri-aromatiques comprenant au moins un motif derive du 3-amino-2-hydroxypyridine, composition tinctoriale, procede et utilisation |
FR3006181B1 (fr) * | 2013-05-29 | 2015-05-15 | Oreal | Colorants directs iminoazomethiniques a un groupe aniline encombre, composition tinctoriale comprenant au moins un tel colorant, procede de mise en œuvre et utilisation |
FR3060331B1 (fr) * | 2016-12-16 | 2020-06-19 | L'oreal | Nouveaux colorants direct azomethiniques symetriques, composition cosmetique comprenant au moins un tel colorant, procede de mise en œuvre et utilisation |
WO2024025869A1 (en) * | 2022-07-25 | 2024-02-01 | Kinnos Inc. | Triarylmethane dyes |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4246181A (en) * | 1969-06-11 | 1981-01-20 | L'oreal | Quinonediimine intermediates for indoanilines |
US3838965A (en) * | 1970-07-13 | 1974-10-01 | Oreal | Dyeing keratinous fibers with azaindoanilines |
LU58848A1 (zh) * | 1969-06-11 | 1971-03-09 | ||
US3956342A (en) * | 1969-06-11 | 1976-05-11 | L'oreal | 4-[4-(2,6-Diaminopyridylimino)]-2,5-cyclohexadien-1-one |
US3929403A (en) * | 1969-06-11 | 1975-12-30 | Oreal | Process for producing indoanilines and keratin fiber dye composition containing the same |
NL139303C (zh) * | 1969-06-25 | |||
US3893802A (en) * | 1970-04-10 | 1975-07-08 | Oreal | Indamines and method of using the same |
LU61316A1 (zh) | 1970-07-13 | 1972-04-04 | ||
US3884625A (en) * | 1970-12-21 | 1975-05-20 | Oreal | Indophenols dyes for coloring keratin fibers |
US4093806A (en) * | 1973-06-22 | 1978-06-06 | L'oreal | Indoanilines |
LU67860A1 (zh) * | 1973-06-22 | 1975-03-27 | ||
LU69456A1 (zh) * | 1974-02-22 | 1975-12-09 | ||
FR2739554B1 (fr) * | 1995-10-06 | 1998-01-16 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant de la 2-amino 3-hydroxy pyridine et une base d'oxydation, et procede de teinture |
JP2004107222A (ja) * | 2002-09-13 | 2004-04-08 | Kao Corp | 染毛剤組成物 |
-
2007
- 2007-12-14 FR FR0759848A patent/FR2925056B1/fr not_active Expired - Fee Related
-
2008
- 2008-12-09 CN CN2008801271696A patent/CN101945640B/zh not_active Expired - Fee Related
- 2008-12-09 US US12/808,100 patent/US8083809B2/en not_active Expired - Fee Related
- 2008-12-09 BR BRPI0819372-0A2A patent/BRPI0819372A2/pt not_active IP Right Cessation
- 2008-12-09 AT AT08860954T patent/ATE518518T1/de not_active IP Right Cessation
- 2008-12-09 WO PCT/EP2008/067152 patent/WO2009077393A1/en active Application Filing
- 2008-12-09 EP EP08860954A patent/EP2229140B1/en not_active Not-in-force
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103998417A (zh) * | 2011-12-13 | 2014-08-20 | 欧莱雅 | 特定的醌直接染料、包含至少一种此染料的染料组合物、其实施方法及其用途 |
CN103998417B (zh) * | 2011-12-13 | 2016-10-19 | 欧莱雅 | 特定的醌直接染料、包含至少一种此染料的染料组合物、其实施方法及其用途 |
Also Published As
Publication number | Publication date |
---|---|
FR2925056B1 (fr) | 2010-01-08 |
EP2229140B1 (en) | 2011-08-03 |
WO2009077393A1 (en) | 2009-06-25 |
US8083809B2 (en) | 2011-12-27 |
CN101945640B (zh) | 2013-08-28 |
US20110041261A1 (en) | 2011-02-24 |
ATE518518T1 (de) | 2011-08-15 |
EP2229140A1 (en) | 2010-09-22 |
BRPI0819372A2 (pt) | 2014-10-14 |
FR2925056A1 (fr) | 2009-06-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101945640B (zh) | 从2-氯-3-氨基-6-甲基苯酚获得的偶氮甲碱直接染料或这些染料的还原前体、以及从这些染料或前体开始的染发方法 | |
CN101945850A (zh) | 从2-烷基间苯二酚获得的偶氮甲碱直接染料或偶氮甲碱直接染料的还原前体、以及使用这些染料或前体的染发方法 | |
CN101124218A (zh) | 不对称重氮化合物、包含其的组合物、染色方法以及包含所述组合物的装置 | |
JP4094624B2 (ja) | 特定のモノカチオン性モノアゾ染料を含有するヒトのケラチン繊維を染色するための組成物 | |
CN102712592B (zh) | 阳离子型氨基吡啶、含阳离子型氨基吡啶的染料组合物及其方法和用途 | |
JPH11508278A (ja) | 酸化染料前駆体および粉末直接染料を用いるケラチン繊維の染色方法 | |
JP2007146122A (ja) | アンスラキノン発色団を含む混合カチオン性染料及び毛髪染色におけるその使用 | |
US20060026777A1 (en) | N-alkylpolyhydroxylated secondary para-phenylenediamines, dye compositions comprising them, processes, and uses thereof | |
CN103998531B (zh) | 三芳香族偶氮甲碱直接染料、包含至少一种此类染料的染料组合物、实施方法及用途 | |
CN102015646B (zh) | 从2-氨基-3-羟基吡啶获得的偶氮甲碱直接染料或这些染料的还原前体、以及使用这些染料或前体的染发方法 | |
US4511360A (en) | Dyeing compositions based on oxidation dyestuff precursors and on nitro benzene dyestuffs and their use for dyeing keratin fibres | |
CN103582680A (zh) | 二硫化物染料 | |
JP2017186573A (ja) | 特定のアゾメチン直接染料、少なくとも1つのこのような化合物を含む染料組成物、そのための実施方法及びその使用 | |
JP2007084510A (ja) | 毛髪化粧料およびそれに含まれる有機顔料ナノ粒子の製造方法 | |
CN107428709A (zh) | 阳离子直接染料 | |
KR20060054013A (ko) | 2가 양이온성 비스-하이드라존 화합물, 하나 이상의 상기화합물을 포함하는 염색 조성물, 그의 사용방법 및 그의용도 | |
JP2007008940A (ja) | 飽和環状基を含む架橋によって結合されている新規なダブルパラ−フェニレンジアミン類及び染色におけるこれの使用 | |
CN107257797A (zh) | 携带两个吡唑并吡啶单元的偶氮甲碱类化合物用于染色角蛋白纤维的用途 | |
JP6207521B2 (ja) | 特定のキノン直接染料、少なくとも1つのこのような染料を含む染料組成物、そのための実施方法及びその使用 | |
CN107501991A (zh) | 包含源自间苯二酚的至少一个单元的三芳香族偶氮甲碱直接染料、染色组合物、方法及用途 | |
CN102971290A (zh) | 阳离子型6-氨基二氢吲哚、包含其的染色组合物、其方法和用途 | |
CN107223124B (zh) | 携带吡唑并吡啶单元的偶氮甲碱类型的化合物用于染色角蛋白纤维的用途 | |
JPH06207114A (ja) | 新規な3−ピリジンアゾ染料並びに3−ピリジンアゾ染料を含有する毛髪染色用薬剤 | |
KR20050069909A (ko) | 특별한 이중 이차 파라-페닐렌디아민, 이를 함유하는 염색조성물 및 상기 조성물을 사용하는 염색 방법 | |
DE602004008730T2 (de) | Synthese von Tetraazapentanmethin-Verbindungen und Verfahren zum Färben von Keratinfasern unter Anwendung dieses Syntheseverfahrens |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130828 Termination date: 20201209 |
|
CF01 | Termination of patent right due to non-payment of annual fee |