US20020002748A1 - Composition for the direct dyeing of keratin fibres with a cationic direct dye and a polyol and/or a polyol ether - Google Patents
Composition for the direct dyeing of keratin fibres with a cationic direct dye and a polyol and/or a polyol ether Download PDFInfo
- Publication number
- US20020002748A1 US20020002748A1 US09/321,890 US32189099A US2002002748A1 US 20020002748 A1 US20020002748 A1 US 20020002748A1 US 32189099 A US32189099 A US 32189099A US 2002002748 A1 US2002002748 A1 US 2002002748A1
- Authority
- US
- United States
- Prior art keywords
- chosen
- hydrogen atom
- alkyl radicals
- radicals
- composition
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 229920005862 polyol Polymers 0.000 title claims abstract description 57
- 150000003077 polyols Chemical class 0.000 title claims abstract description 56
- 239000000982 direct dye Substances 0.000 title claims abstract description 39
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 32
- 102000011782 Keratins Human genes 0.000 title claims abstract description 30
- 108010076876 Keratins Proteins 0.000 title claims abstract description 30
- 238000009967 direct dyeing Methods 0.000 title claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 22
- 210000004209 hair Anatomy 0.000 claims abstract description 23
- 238000004043 dyeing Methods 0.000 claims abstract description 16
- 102000004316 Oxidoreductases Human genes 0.000 claims abstract description 14
- 108090000854 Oxidoreductases Proteins 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000000835 fiber Substances 0.000 claims abstract 20
- -1 C1-C4 alkyl radicals Chemical class 0.000 claims description 116
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000011630 iodine Substances 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 150000008378 aryl ethers Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- 239000002453 shampoo Substances 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 claims description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 2
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 claims description 2
- KJBPYIUAQLPHJG-UHFFFAOYSA-N 1-phenylmethoxypropan-2-ol Chemical compound CC(O)COCC1=CC=CC=C1 KJBPYIUAQLPHJG-UHFFFAOYSA-N 0.000 claims description 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 2
- ZUAURMBNZUCEAF-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethanol Chemical compound OCCOCCOC1=CC=CC=C1 ZUAURMBNZUCEAF-UHFFFAOYSA-N 0.000 claims description 2
- LJVNVNLFZQFJHU-UHFFFAOYSA-N 2-(2-phenylmethoxyethoxy)ethanol Chemical compound OCCOCCOCC1=CC=CC=C1 LJVNVNLFZQFJHU-UHFFFAOYSA-N 0.000 claims description 2
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 2
- CUZKCNWZBXLAJX-UHFFFAOYSA-N 2-phenylmethoxyethanol Chemical compound OCCOCC1=CC=CC=C1 CUZKCNWZBXLAJX-UHFFFAOYSA-N 0.000 claims description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 229940113120 dipropylene glycol Drugs 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 4
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 4
- 238000001035 drying Methods 0.000 claims 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 23
- 0 *[2H]=[2H]C1=CC=C(N(C)C)C=C1.CC.CC Chemical compound *[2H]=[2H]C1=CC=C(N(C)C)C=C1.CC.CC 0.000 description 11
- ORKBASUJBNGFJB-UHFFFAOYSA-N BN=NC1=CC=C(N(C)C)C=C1.CC.CC.II Chemical compound BN=NC1=CC=C(N(C)C)C=C1.CC.CC.II ORKBASUJBNGFJB-UHFFFAOYSA-N 0.000 description 5
- HXUBKFKNOPHIPO-UHFFFAOYSA-N CC1=C2C=CC=CC2=[N+](C)C=C1.CC1=CC(C)=[N+](C)S1.CC1=CC=C2C=CC=CC2=[N+]1C.CC1=CSC(C)=[N+]1C.CC1=N[N+](C)=C(C)S1.CC1=[N+](C)N=C(N(C)C)S1 Chemical compound CC1=C2C=CC=CC2=[N+](C)C=C1.CC1=CC(C)=[N+](C)S1.CC1=CC=C2C=CC=CC2=[N+]1C.CC1=CSC(C)=[N+]1C.CC1=N[N+](C)=C(C)S1.CC1=[N+](C)N=C(N(C)C)S1 HXUBKFKNOPHIPO-UHFFFAOYSA-N 0.000 description 5
- KCUGPPHNMASOTE-UHFFFAOYSA-N CC1=[N+](C)C=CN1C Chemical compound CC1=[N+](C)C=CN1C KCUGPPHNMASOTE-UHFFFAOYSA-N 0.000 description 5
- VTTYEZVJDUBAHW-UHFFFAOYSA-N C.CC1=C(C)[N+](C)=C(C)N1C.CC1=CC(C)=[N+](C)N1C.CC1=CC2=C(C=C1)C=[N+](C)N2C.CC1=CC2=[N+](C)C=CC=C2C=C1.CC1=CC=[N+](C)C=C1.CC1=CC=[N+](C)N1C.CC1=N[N+](C)=C(C)N1C.CC1=[N+](C)C=CN1C.CC1=[N+](C)N(C)C2=CC=CC=C21.CC1=[N+](C)N=CN1C Chemical compound C.CC1=C(C)[N+](C)=C(C)N1C.CC1=CC(C)=[N+](C)N1C.CC1=CC2=C(C=C1)C=[N+](C)N2C.CC1=CC2=[N+](C)C=CC=C2C=C1.CC1=CC=[N+](C)C=C1.CC1=CC=[N+](C)N1C.CC1=N[N+](C)=C(C)N1C.CC1=[N+](C)C=CN1C.CC1=[N+](C)N(C)C2=CC=CC=C21.CC1=[N+](C)N=CN1C VTTYEZVJDUBAHW-UHFFFAOYSA-N 0.000 description 4
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 239000002535 acidifier Substances 0.000 description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
- 239000002610 basifying agent Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BQMSXKNOERIPLE-UHFFFAOYSA-N CC1=C(C)N(C)=C(C)N1C.CC1=CC(C)=[N+](C)N1C.CC1=CC2=C(C=C1)C=N(C)N2C.CC1=CC2=[N+](C)C=CC=C2C=C1.CC1=CC=N(C)C=C1.CC1=CC=[N+](C)N1C.CC1=N(C)N=CN1C.CC1=N[N+](C)=C(C)N1C.CC1=[N+](C)C=CN1C.CC1=[N+](C)N(C)C2=CC=CC=C21 Chemical compound CC1=C(C)N(C)=C(C)N1C.CC1=CC(C)=[N+](C)N1C.CC1=CC2=C(C=C1)C=N(C)N2C.CC1=CC2=[N+](C)C=CC=C2C=C1.CC1=CC=N(C)C=C1.CC1=CC=[N+](C)N1C.CC1=N(C)N=CN1C.CC1=N[N+](C)=C(C)N1C.CC1=[N+](C)C=CN1C.CC1=[N+](C)N(C)C2=CC=CC=C21 BQMSXKNOERIPLE-UHFFFAOYSA-N 0.000 description 1
- DGLHBQQYSLBIMF-UHFFFAOYSA-O CC1=C(O)C=CC2=C1N(C)[N+](C)=C2.CC1=CC(C)=[N+](C)C(=O)N1C.CC1=CC=CC=[N+]1C.CC1=CC=C[N+](C)=C1.CC1=CC=[N+](C)C=C1.CC1=[N+](C)C(=O)N(C)C=C1.CC1=[N+](C)C2=CC=CC=C2S1.CC1=[N+](C)N=CC1C Chemical compound CC1=C(O)C=CC2=C1N(C)[N+](C)=C2.CC1=CC(C)=[N+](C)C(=O)N1C.CC1=CC=CC=[N+]1C.CC1=CC=C[N+](C)=C1.CC1=CC=[N+](C)C=C1.CC1=[N+](C)C(=O)N(C)C=C1.CC1=[N+](C)C2=CC=CC=C2S1.CC1=[N+](C)N=CC1C DGLHBQQYSLBIMF-UHFFFAOYSA-O 0.000 description 1
- IYLZFJJNTDQYPL-UHFFFAOYSA-M CC1=CSC(/N=N/C2=CC=C(N(C)C)C=C2C#N)=[N+]1C.CC1=CSC(N=NC2=CC=C(N(C)C)C=C2)=[N+]1C.CC1=N[N+](C)=C(N=NC2=CC=C(N(C)C)C=C2)S1.CC1=[N+](C)SC(N=NC2=CC=C(N(C)C)C=C2)=C1.CN(C)C1=CC=C(N=NC2=C3C=CC=CC3=[N+](C)C=C2)C=C1.CN(C)C1=CC=C(N=NC2=CC=C3C=CC=CC3=[N+]2C)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N(C)C)S2)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N)S2)C=C1.CNC1=N[N+](C)=C(N=NC2=CC(C)=C(N(C)C)C=C2)S1.CS(=O)(=O)O[O-].[Cl-].[Cl-] Chemical compound CC1=CSC(/N=N/C2=CC=C(N(C)C)C=C2C#N)=[N+]1C.CC1=CSC(N=NC2=CC=C(N(C)C)C=C2)=[N+]1C.CC1=N[N+](C)=C(N=NC2=CC=C(N(C)C)C=C2)S1.CC1=[N+](C)SC(N=NC2=CC=C(N(C)C)C=C2)=C1.CN(C)C1=CC=C(N=NC2=C3C=CC=CC3=[N+](C)C=C2)C=C1.CN(C)C1=CC=C(N=NC2=CC=C3C=CC=CC3=[N+]2C)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N(C)C)S2)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N)S2)C=C1.CNC1=N[N+](C)=C(N=NC2=CC(C)=C(N(C)C)C=C2)S1.CS(=O)(=O)O[O-].[Cl-].[Cl-] IYLZFJJNTDQYPL-UHFFFAOYSA-M 0.000 description 1
- UJVOPKKQRGZOTB-UHFFFAOYSA-N CC1=CSC(/N=N/C2=CC=C(N(C)C)C=C2C#N)=[N+]1C.CC1=CSC(N=NC2=CC=C(N(C)C)C=C2)=[N+]1C.CC1=N[N+](C)=C(N=NC2=CC=C(N(C)C)C=C2)S1.CC1=[N+](C)SC(N=NC2=CC=C(N(C)C)C=C2)=C1.CN(C)C1=CC=C(N=NC2=C3C=CC=CC3=[N+](C)C=C2)C=C1.CN(C)C1=CC=C(N=NC2=CC=C3C=CC=CC3=[N+]2C)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N(C)C)S2)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N)S2)C=C1.CNC1=N[N+](C)=C(N=NC2=CC(C)=C(N(C)C)C=C2)S1.[Cl-] Chemical compound CC1=CSC(/N=N/C2=CC=C(N(C)C)C=C2C#N)=[N+]1C.CC1=CSC(N=NC2=CC=C(N(C)C)C=C2)=[N+]1C.CC1=N[N+](C)=C(N=NC2=CC=C(N(C)C)C=C2)S1.CC1=[N+](C)SC(N=NC2=CC=C(N(C)C)C=C2)=C1.CN(C)C1=CC=C(N=NC2=C3C=CC=CC3=[N+](C)C=C2)C=C1.CN(C)C1=CC=C(N=NC2=CC=C3C=CC=CC3=[N+]2C)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N(C)C)S2)C=C1.CN(C)C1=CC=C(N=NC2=[N+](C)N=C(N)S2)C=C1.CNC1=N[N+](C)=C(N=NC2=CC(C)=C(N(C)C)C=C2)S1.[Cl-] UJVOPKKQRGZOTB-UHFFFAOYSA-N 0.000 description 1
- KFCCMMDIQCCRBJ-UHFFFAOYSA-M CN(C)[W]N(C)C.[V]I Chemical compound CN(C)[W]N(C)C.[V]I KFCCMMDIQCCRBJ-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- 150000001783 ceramides Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
-
- 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
- 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
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
Definitions
- the invention relates to a direct dye composition for keratin fibres, in particular for human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing and which is free of oxidases or oxidoreductases, at least one cationic direct dye of given formula and at least one specific polyol and/or polyol ether.
- Subjects of the invention are also the dyeing processes and devices using the said composition.
- semi-permanent or temporary dyeing, or direct dyeing involves dyes capable of giving the hair's natural colour a more or less pronounced change which may withstand shampooing several times.
- These dyes are known as direct dyes; they can be used with or without an oxidizing agent.
- the aim is to obtain a lightening coloration.
- the lightening coloration is carried out by applying to the hair the mixture, prepared at the time of use, of a direct dye and an oxidizing agent, and in particular makes it possible to obtain, by lightening the melanin in the hair, an advantageous effect such as a uniform colour in the case of grey hair, or to bring out the colour in the case of naturally pigmented hair.
- a first subject of the present invention is thus a composition for the direct dyeing of keratin fibres, and in particular human keratin fibres such as the hair, containing, in a medium which is suitable for dyeing, (i) at least one cationic direct dye whose structure corresponds to the following formulae, characterized in that it also contains (ii) at least one specific polyol and/or polyol ether.
- the cationic direct dye which can be used according to the present invention is a compound chosen from those of formulae (I), (II), (III) and (III′) below:
- D is chosen from a nitrogen atom and a —CH group
- R 1 and R 2 which may be identical or different, are chosen from a hydrogen atom, C 1 -C 4 alkyl radicals having a substituent chosen from —CN, —OH, and —NH 2 radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C 1 -C 4 alkyl radicals,
- R 3 and R′ 3 which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, and acetyloxy radicals,
- X ⁇ is an anion, preferably chosen from chloride, methyl sulphate, and acetate,
- A is a group chosen from structures A 1 to A 18 below:
- R 4 is chosen from C 1 -C 4 alkyl radicals which can be substituted with a hydroxyl radical and R 5 is chosen from C 1 -C 4 alkoxy radicals, with the proviso that when D is —CH, when A is A 4 or A 13 and when R 3 is other than an alkoxy radical, then R 1 and R 2 are not simultaneously a hydrogen atom;
- R 6 is chosen from a hydrogen atom and C 1 -C 4 alkyl radicals
- R 7 is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R 6 , a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C 1 -C 4 alkyl radicals,
- R 8 and R 9 which may be identical or different, are chosen from a hydrogen atom, halogen atoms, such as bromine, chlorine, or fluorine, and C 1 -C 4 alkyl, C 1 -C 4 alkoxy, and —CN radicals,
- X ⁇ is an anion
- B is a group chosen from structures B1 to B6 below:
- R 10 is chosen from C 1 -C 4 alkyl radicals
- R 11 and R 12 which may be identical or different, are chosen from a hydrogen atom and C 1 -C 4 alkyl radicals
- R 13 is chosen from a hydrogen atom, C 1 -C 4 alkoxy radicals, halogen atoms, such as bromine, chlorine, iodine and fluorine, and unsubstituted and substituted amino radicals,
- R 14 is chosen from a hydrogen atom, and C 1 -C 4 alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C 1 -C 4 alkyl radicals,
- R 15 is chosen from a hydrogen atom and halogen atoms, such as bromine, chlorine, iodine and fluorine,
- R 16 and R 17 which may be identical or different, are chosen from a hydrogen atom and C 1 -C 4 alkyl radicals,
- D 1 and D 2 which may be identical or different, are chosen from a nitrogen atom and a —CH group,
- m is 0 or 1
- X ⁇ is an anion
- E is a group chosen from structures E1 to E8 below:
- R′ is chosen from C 1 -C 4 alkyl radicals
- E when m is 0 and when D 1 is a nitrogen atom, then E can also be a group of structure E9 below:
- R′ is chosen from C 1 -C 4 alkyl radicals.
- cationic direct dyes of formulae (I), (II), (III) and (III′) which can be used in the dye compositions in accordance with the invention are known compounds and are described, for example, in patent applications WO 95/01772, WO 95/15144 and EP-A-0,714,954 (the disclosures of which are specifically incorporated by reference herein).
- the compounds most particularly preferred are those corresponding to structures (I1), (I2), (I14) and (I31).
- the cationic direct dye(s) used according to the invention preferably represent(s) from 0.001 to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
- polyol denotes a compound of linear, branched or cyclic, saturated or unsaturated alkyl type bearing at least two —OH functions on the alkyl chain, as well as the polymers (polyethers) of these polyhydroxyalkyl compounds.
- the alkyl compound preferably contains from 2 to 12 carbon atoms and even more preferably from 2 to 9.
- the polyols used according to the invention can be chosen in particular from C 2 -C 9 polyols, as well as polyalkylene glycols such as, more particularly, polyethylene glycols and polypropylene glycols.
- C 2 -C 9 polyols mention may be made in particular of glycerol, propylene glycol, 1,3-propanediol, 2-butene-1,4-diol, pentane-1,5-diol, 2,2-dimethylpropane-1,3-diol, 3-methylpentane-1,5-diol, pentane-1,2-diol, 2,2,4-trimethylpentane-1,3-diol, 2-methhylpropane-1,3-diol, hexylene glycol, 1,3-butylene glycol, dipropylene glycol, diethylene glycol and triethylene glycol.
- glycerol propylene glycol
- 1,3-propanediol 1,3-propanediol
- 2-butene-1,4-diol pentane-1,5-diol
- the specific polyol ethers according to the invention are chosen from C 1 -C 8 aliphatic ethers of C 3 -C 9 polyols and C 6 -C 8 aromatic ethers of C 2 -C 9 polyols.
- C 1 -C 8 aliphatic ethers of C 3 -C 9 polyols mention may be made in particular of propylene glycol monomethyl ether, propylene glycol monoethyl ether, isopropylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether and diethylene glycol dimethyl ether.
- C 6 -C 8 aromatic ethers of C 2 -C 9 polyols mention may be made in particular of ethylene glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monophenyl ether, propylene glycol monobenzyl ether, diethylene glycol monophenyl ether and diethylene glycol monobenzyl ether.
- the polyol(s) and/or the polyol ether(s) described for the purposes of the invention are present in the dye composition in accordance with the invention in proportions generally ranging from 0.1 to 40% by weight, and even more particularly from 0.5 to 20% by weight, relative to the total weight of the composition.
- the medium which is suitable for dyeing (or support) generally comprises a mixture of water and at least one polyol and/or polyol ether as defined above. It can also contain one or more organic solvents other than the polyol(s) and/or polyol ether(s) used in accordance with the invention, in order to dissolve the compounds which would not be sufficiently soluble in the medium.
- Organic solvents which may be mentioned, for example, are C 1 -C 4 alkanols, such as ethanol and isopropanol, as well as aromatic alcohols such as benzyl alcohol, similar products and mixtures thereof.
- the said additional organic solvents can be present in proportions preferably ranging from 0.5 to 40% by weight approximately relative to the total weight of the dye composition, and even more preferably from 1 to 20% by weight approximately.
- the pH of the dye composition in accordance with the invention generally ranges from 2 to 11 approximately, and preferably from 5 to 10 approximately. It can be adjusted to the desired value using acidifying or basifying agents usually used for the direct dyeing of keratin fibres.
- the acidifying agents mention may be made of, for example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
- inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
- basifying agents mention may be made of, for example, aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (IV) below:
- W is a propylene residue optionally having a substituent chosen from a hydroxyl group and C 1 -C 6 alkyl radicals
- R 18 , R 19 , R 20 and R 21 which may be identical or different, are chosen from a hydrogen atom and C 1 -C 6 alkyl and C 1 -C 6 hydroxylalkyl radicals.
- the dye composition in accordance with the invention can contain one or more additional direct dyes which may be chosen, for example, from nitrobenzene dyes, anthraquinone dyes, naphthoquinone dyes, triarylmethane dyes, xanthene dyes and azo dyes which are non-cationic.
- the dye composition in accordance with the invention can also contain various adjuvants conventionally used in compositions for the direct dyeing of the hair, such as antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, surfactants, film-forming agents, ceramides, preserving agents, screening agents and opacifiers.
- adjuvants conventionally used in compositions for the direct dyeing of the hair, such as antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, surfactants, film-forming agents, ceramides, preserving agents, screening agents and opacifiers.
- the direct dye composition according to the invention can be in various forms, such as in the form of liquids, shampoos, creams or gels or any other form which is suitable for dyeing keratin fibres, and in particular human hair. It can be obtained by mixing, at the time of use, a composition, which may be a in pulverulent form, containing the cationic direct dye(s) with a composition containing the specific polyol(s) and/or polyol ether(s).
- the dye composition in accordance with the invention also contains at least one oxidizing agent other than an enzyme such as oxidases and oxidoreductases but chosen, for example, from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates.
- oxidases and oxidoreductases but chosen, for example, from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates.
- the use of hydrogen peroxide is particularly preferred.
- Another subject of the invention is a process for the direct dyeing of keratin fibres, and in particular human keratin fibres such as the hair, using the dye composition as defined above.
- At least one dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo, rinsed again and dried.
- the time required to develop the coloration on the keratin fibres generally ranges from 3 to 60 minutes and even more precisely from 5 to 40 minutes.
- At least one dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, without final rinsing.
- the dyeing process includes a preliminary step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is suitable for dyeing, at least one cationic direct dye as defined above and, on the other hand, a composition (B) containing, in a medium which is suitable for dyeing, at least one oxidizing agent, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres, composition (A) or composition (B) containing at least one polyol and/or polyol ether as defined above.
- a preliminary step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is suitable for dyeing, at least one cationic direct dye as defined above and, on the other hand, a composition (B) containing, in a medium which is suitable for dyeing, at least one oxidizing agent, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibre
- Another subject of the invention is a multi-compartment dyeing device or “kit” or any other multi-compartment packaging system, a first compartment of which contains composition (A) as defined above and a second compartment of which contains composition (B) as defined above.
- These devices can be equipped with means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2,586,913 in the name of L'Oréal, the disclosure of which is specifically incorporated by reference herein.
- the dye composition below was prepared: Cationic direct dye of formula I(14) 0.2 g Propylene glycol 10.0 g 2-Amino-2-methylpropanol qs pH 9 Demineralized water qs 100 g
- the dye composition below was prepared: Cationic direct dye of formula I(1) 0.2 g Propylene glycol monomethyl ether 10.0 g 2-Amino-2-methylpropanol qs pH 9 Demineralized water qs 100 g
Abstract
The invention relates to a direct dye composition for keratin fibers, in particular for human keratin fibers such as the hair, comprising, in a medium which is suitable for dyeing and which is free of oxidases or oxidoreductases, at least one cationic direct dye of given formula and at least one specific polyol and/or polyol ether. Subjects of the invention are also the dyeing processes and devices/kits using the said composition.
Description
- The invention relates to a direct dye composition for keratin fibres, in particular for human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing and which is free of oxidases or oxidoreductases, at least one cationic direct dye of given formula and at least one specific polyol and/or polyol ether.
- Subjects of the invention are also the dyeing processes and devices using the said composition.
- In the hair sector, semi-permanent or temporary dyeing, or direct dyeing, involves dyes capable of giving the hair's natural colour a more or less pronounced change which may withstand shampooing several times. These dyes are known as direct dyes; they can be used with or without an oxidizing agent. In the presence of an oxidizing agent, the aim is to obtain a lightening coloration. The lightening coloration is carried out by applying to the hair the mixture, prepared at the time of use, of a direct dye and an oxidizing agent, and in particular makes it possible to obtain, by lightening the melanin in the hair, an advantageous effect such as a uniform colour in the case of grey hair, or to bring out the colour in the case of naturally pigmented hair.
- Among the cationic direct dyes available in the field of dyeing keratin fibres, in particular human keratin fibres, compounds which are already known are those whose structure is developed in the text which follows; nevertheless, these dyes lead to colorations which have properties that are still insufficient as regards the staying power, in terms of resistance to the various attacking factors to which the hair may be subjected (light, bad weather, shampooing).
- After considerable research conducted in this matter, the Applicant has now discovered that it is possible to obtain novel compositions for the direct dyeing of keratin fibres, which are capable of leading to colorations which can be particularly resistant to the various attacking factors to which the hair may be subjected, by combining at least one specific polyol and/or polyol ether with at least one cationic direct dye known in the prior art, and of formulae respectively defined below.
- This discovery forms the basis of the present invention.
- A first subject of the present invention is thus a composition for the direct dyeing of keratin fibres, and in particular human keratin fibres such as the hair, containing, in a medium which is suitable for dyeing, (i) at least one cationic direct dye whose structure corresponds to the following formulae, characterized in that it also contains (ii) at least one specific polyol and/or polyol ether.
- (i) The cationic direct dye which can be used according to the present invention is a compound chosen from those of formulae (I), (II), (III) and (III′) below:
- a) the compounds of formula (I) below:
- in which formula (I):
- D is chosen from a nitrogen atom and a —CH group,
- R 1 and R2, which may be identical or different, are chosen from a hydrogen atom, C1-C4 alkyl radicals having a substituent chosen from —CN, —OH, and —NH2 radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C1-C4 alkyl radicals,
- R 3 and R′3, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C1-C4 alkoxy, C1-C4 alkyl, and acetyloxy radicals,
- X − is an anion, preferably chosen from chloride, methyl sulphate, and acetate,
- A is a group chosen from structures A 1 to A18 below:
- in which R 4 is chosen from C1-C4 alkyl radicals which can be substituted with a hydroxyl radical and R5 is chosen from C1-C4 alkoxy radicals, with the proviso that when D is —CH, when A is A4 or A13 and when R3 is other than an alkoxy radical, then R1 and R2 are not simultaneously a hydrogen atom;
- b) the compounds of formula (II) below:
- in which formula (II):
- R 6 is chosen from a hydrogen atom and C1-C4 alkyl radicals,
- R 7 is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R6, a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C1-C4 alkyl radicals,
- R 8 and R9, which may be identical or different, are chosen from a hydrogen atom, halogen atoms, such as bromine, chlorine, or fluorine, and C1-C4 alkyl, C1-C4 alkoxy, and —CN radicals,
- X − is an anion,
- B is a group chosen from structures B1 to B6 below:
- in which R 10 is chosen from C1-C4 alkyl radicals, and R11 and R12, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals;
- c) the compounds of formulae (III) and (III′) below:
- in which formulae (III) and (III′):
- R 13 is chosen from a hydrogen atom, C1-C4 alkoxy radicals, halogen atoms, such as bromine, chlorine, iodine and fluorine, and unsubstituted and substituted amino radicals,
- R 14 is chosen from a hydrogen atom, and C1-C4 alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C1-C4 alkyl radicals,
- R 15 is chosen from a hydrogen atom and halogen atoms, such as bromine, chlorine, iodine and fluorine,
- R 16 and R17, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals,
- D 1 and D2, which may be identical or different, are chosen from a nitrogen atom and a —CH group,
- m is 0 or 1,
- it being understood that when R 13 is an unsubstituted amino radical, then D1 and D2 are simultaneously a —CH group and m is 0,
- X − is an anion,
- E is a group chosen from structures E1 to E8 below:
- in which R′ is chosen from C 1-C4 alkyl radicals;
- when m is 0 and when D 1 is a nitrogen atom, then E can also be a group of structure E9 below:
- in which R′ is chosen from C 1-C4 alkyl radicals.
- The cationic direct dyes of formulae (I), (II), (III) and (III′) which can be used in the dye compositions in accordance with the invention are known compounds and are described, for example, in patent applications WO 95/01772, WO 95/15144 and EP-A-0,714,954 (the disclosures of which are specifically incorporated by reference herein).
- Among the cationic direct dyes of formula (I) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (I1) to (I52) below:
- Among the compounds of structures (I1) to (I52) described above, the compounds most particularly preferred are those corresponding to structures (I1), (I2), (I14) and (I31).
- Among the cationic direct dyes of formula (II) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (II1) to (II9) below:
- Among the cationic direct dyes of formula (III) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (III1) to (III18) below:
- Among the specific compounds of structures (III1) to (III18) described above, the compounds most particularly preferred are those corresponding to structures (III4), (III5) and (III13).
- Among the cationic direct dyes of formula (III′) which can be used in the dye compositions in accordance with the invention, mention may be made more particularly of the compounds corresponding to structures (III′1) to (III′3) below:
- The cationic direct dye(s) used according to the invention preferably represent(s) from 0.001 to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
- (ii) For the purposes of the invention, the term “polyol” denotes a compound of linear, branched or cyclic, saturated or unsaturated alkyl type bearing at least two —OH functions on the alkyl chain, as well as the polymers (polyethers) of these polyhydroxyalkyl compounds.
- The alkyl compound preferably contains from 2 to 12 carbon atoms and even more preferably from 2 to 9.
- The polyols used according to the invention can be chosen in particular from C 2-C9 polyols, as well as polyalkylene glycols such as, more particularly, polyethylene glycols and polypropylene glycols.
- Among the C 2-C9 polyols, mention may be made in particular of glycerol, propylene glycol, 1,3-propanediol, 2-butene-1,4-diol, pentane-1,5-diol, 2,2-dimethylpropane-1,3-diol, 3-methylpentane-1,5-diol, pentane-1,2-diol, 2,2,4-trimethylpentane-1,3-diol, 2-methhylpropane-1,3-diol, hexylene glycol, 1,3-butylene glycol, dipropylene glycol, diethylene glycol and triethylene glycol.
- The specific polyol ethers according to the invention are chosen from C 1-C8 aliphatic ethers of C3-C9 polyols and C6-C8 aromatic ethers of C2-C9 polyols.
- Among the C 1-C8 aliphatic ethers of C3-C9 polyols, mention may be made in particular of propylene glycol monomethyl ether, propylene glycol monoethyl ether, isopropylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether and diethylene glycol dimethyl ether.
- Among the C 6-C8 aromatic ethers of C2-C9 polyols, mention may be made in particular of ethylene glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monophenyl ether, propylene glycol monobenzyl ether, diethylene glycol monophenyl ether and diethylene glycol monobenzyl ether.
- The polyol(s) and/or the polyol ether(s) described for the purposes of the invention are present in the dye composition in accordance with the invention in proportions generally ranging from 0.1 to 40% by weight, and even more particularly from 0.5 to 20% by weight, relative to the total weight of the composition.
- The medium which is suitable for dyeing (or support) generally comprises a mixture of water and at least one polyol and/or polyol ether as defined above. It can also contain one or more organic solvents other than the polyol(s) and/or polyol ether(s) used in accordance with the invention, in order to dissolve the compounds which would not be sufficiently soluble in the medium. Organic solvents which may be mentioned, for example, are C 1-C4 alkanols, such as ethanol and isopropanol, as well as aromatic alcohols such as benzyl alcohol, similar products and mixtures thereof.
- The said additional organic solvents can be present in proportions preferably ranging from 0.5 to 40% by weight approximately relative to the total weight of the dye composition, and even more preferably from 1 to 20% by weight approximately.
- The pH of the dye composition in accordance with the invention generally ranges from 2 to 11 approximately, and preferably from 5 to 10 approximately. It can be adjusted to the desired value using acidifying or basifying agents usually used for the direct dyeing of keratin fibres.
- Among the acidifying agents, mention may be made of, for example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
- Among the basifying agents, mention may be made of, for example, aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (IV) below:
- in which W is a propylene residue optionally having a substituent chosen from a hydroxyl group and C 1-C6 alkyl radicals; R18, R19, R20 and R21, which may be identical or different, are chosen from a hydrogen atom and C1-C6 alkyl and C1-C6 hydroxylalkyl radicals.
- In addition to the cationic direct dye(s) (i) defined above, the dye composition in accordance with the invention can contain one or more additional direct dyes which may be chosen, for example, from nitrobenzene dyes, anthraquinone dyes, naphthoquinone dyes, triarylmethane dyes, xanthene dyes and azo dyes which are non-cationic.
- The dye composition in accordance with the invention can also contain various adjuvants conventionally used in compositions for the direct dyeing of the hair, such as antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, surfactants, film-forming agents, ceramides, preserving agents, screening agents and opacifiers.
- Needless to say, a person skilled in the art will take care to select this or these optional complementary compound(s) such that the advantageous properties intrinsically associated with the direct dye composition in accordance with the invention are not, or are not substantially, adversely affected by the addition(s) envisaged.
- The direct dye composition according to the invention can be in various forms, such as in the form of liquids, shampoos, creams or gels or any other form which is suitable for dyeing keratin fibres, and in particular human hair. It can be obtained by mixing, at the time of use, a composition, which may be a in pulverulent form, containing the cationic direct dye(s) with a composition containing the specific polyol(s) and/or polyol ether(s).
- When the combination of the cationic direct dye (i) and the polyol and/or polyol ether (ii) according to the invention is used in a composition intended for lightening direct dyeing, then the dye composition in accordance with the invention also contains at least one oxidizing agent other than an enzyme such as oxidases and oxidoreductases but chosen, for example, from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates. The use of hydrogen peroxide is particularly preferred.
- Another subject of the invention is a process for the direct dyeing of keratin fibres, and in particular human keratin fibres such as the hair, using the dye composition as defined above.
- According to a first variant of this direct dyeing process in accordance with the invention, at least one dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo, rinsed again and dried.
- The time required to develop the coloration on the keratin fibres generally ranges from 3 to 60 minutes and even more precisely from 5 to 40 minutes.
- According to a second variant of this direct dyeing process in accordance with the invention, at least one dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, without final rinsing.
- According to another specific embodiment of this direct dyeing process, and when the dye composition in accordance with the invention contains at least one oxidizing agent, the dyeing process includes a preliminary step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is suitable for dyeing, at least one cationic direct dye as defined above and, on the other hand, a composition (B) containing, in a medium which is suitable for dyeing, at least one oxidizing agent, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres, composition (A) or composition (B) containing at least one polyol and/or polyol ether as defined above.
- Another subject of the invention is a multi-compartment dyeing device or “kit” or any other multi-compartment packaging system, a first compartment of which contains composition (A) as defined above and a second compartment of which contains composition (B) as defined above. These devices can be equipped with means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2,586,913 in the name of L'Oréal, the disclosure of which is specifically incorporated by reference herein.
- The examples which follow are intended to illustrate the invention without, however, limiting its scope.
- The dye composition below was prepared:
Cationic direct dye of formula I(14) 0.2 g Propylene glycol 10.0 g 2-Amino-2-methylpropanol qs pH 9 Demineralized water qs 100 g - The above composition was applied for 30 minutes to locks of natural grey hair containing 90% white hairs. The locks of hair were then rinsed, washed with a standard shampoo and then dried.
- They were dyed an intense orange shade.
- The dye composition below was prepared:
Cationic direct dye of formula I(1) 0.2 g Propylene glycol monomethyl ether 10.0 g 2-Amino-2-methylpropanol qs pH 9 Demineralized water qs 100 g - The above composition was applied for 30 minutes to locks of natural grey hair containing 90% white hairs. The locks of hair were then rinsed, washed with a standard shampoo and then dried.
- They were dyed an intense red shade.
Claims (31)
1. A composition for the direct dyeing of keratin fibers comprising:
(i) at least one cationic direct dye chosen from those of formulae (I), (II), (III) and (III′) below:
in which formula (I):
D is chosen from a nitrogen atom and a —CH group,
R1 and R2, which may be identical or different, are chosen from a hydrogen atom, C1-C4 alkyl radicals having a substituent chosen from —CN, —OH, and —NH2 radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C1-C4 alkyl radicals,
R3 and R′3, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C1-C4 alkoxy, C1-C4 alkyl, and acetyloxy radicals,
X− is an anion,
A is a group chosen from structures A1 to A18 below:
in which R4 is chosen from C1-C4 alkyl radicals which can be substituted with a hydroxyl radical and R5 is chosen from C1-C4 alkoxy radicals, with the proviso that when D is —CH, when A is A4 or A13 and when R3 is other than an alkoxy radical, then R1 and R2 are not simultaneously a hydrogen atom;
in which formula (II):
R6 is chosen from a hydrogen atom and C1-C4 alkyl radicals,
R7 is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R6, a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C1-C4 alkyl radicals,
R8 and R9, which may be identical or different, are chosen from a hydrogen atom, halogen atoms, and C1-C4 alkyl, C1-C4 alkoxy, and —CN radicals,
X− is an anion,
B is a group chosen from structures B1 to B6 below:
in which R10 is chosen from C1-C4 alkyl radicals, and R11 and R12, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals;
in which formulae (Ill) and (III′):
R13 is chosen from a hydrogen atom, C1-C4 alkoxy radicals, halogen atoms chosen from bromine, chlorine, iodine and fluorine and unsubstituted and substituted amino radicals,
R14 is chosen from a hydrogen atom, and C1-C4 alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C1-C4 alkyl radicals,
R15 is chosen from a hydrogen atom and halogen atoms chosen from bromine, chlorine, iodine and fluorine,
R16 and R17, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals,
D1 and D2, which may be identical or different, are chosen from a nitrogen atom and a —CH group,
m is 0 or 1,
it being understood that when R13 is an unsubstituted amino radical, then D1 and D2 are simultaneously a —CH group and m is 0,
X− is an anion,
E is a group chosen from structures E1 to E8 below:
in which R′ is chosen from C1-C4 alkyl radicals;
when m is 0 and when D1 is a nitrogen atom, then E can also be a group of structure E9 below:
in which R′ is chosen from C1-C4 alkyl radicals; and
(ii) at least one compound chosen from polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols, said composition being free of oxidases or oxidoreductases.
2. The composition according to claim 1 , wherein X is chosen from chloride, methyl sulphate and acetate and wherein for R8 and R9, said halogen atoms are chosen from bromine, chlorine, iodine, and fluorine.
3. The composition according to claim 1 , wherein said keratin fibers are human keratin fibers.
4. The composition according to claim 3 , where said human keratin fibers are hair.
5. The composition according to claim 1 , wherein said at least one cationic direct dye of formula (I) is chosen from structures (I1) to (I54) below:
6. The composition according to claim 5 , wherein said at least one cationic direct dye is chosen from structures (I1), (I2), (I14) and (I31).
7. The composition according to claim 1 , wherein said at least one cationic direct dye of formula (II) is chosen from structures (II1) to (II9) below:
8. The composition according to claim 1 , wherein said at least one cationic direct dye of formula (III) is chosen from structures (III1) to (III18) below:
9. The composition according to claim 8 , wherein said at least one cationic direct dye of formula (III) is chosen from structures (III4), (III5) and (III13).
10. The composition according to claim 1 , wherein said at least one cationic direct dye of formula (III′) is chosen from structures (III′1) to (III′3) below:
11. The composition according to claim 1 , wherein said polyols are chosen from C2-C9 polyols and polyalkylene glycols.
12. The composition according to claim 11 , wherein said polyalkylene glycols are chosen from polyethylene glycols and polypropylene glycols.
13. The composition according to claim 11 , wherein said C2-C9 polyols are chosen from glycerol, propylene glycol, 1,3-propanediol, 2-butene-1,4-diol, pentane-1,5-diol, 2,2-dimethylpropane-1,3-diol, 3-methylpentane-1,5-diol, pentane-1,2-diol, 2,2,4-trimethylpentane-1,3-diol, 2-methylpropane-1,3-diol, hexylene glycol, 1,3-butylene glycol, dipropylene glycol, diethylene glycol and triethylene glycol.
14. The composition according to claim 1 , wherein said C1-C8 aliphatic ethers of C3-C9 polyols are chosen from propylene glycol monomethyl ether, propylene glycol monoethyl ether, isopropylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether and diethylene glycol dimethyl ether.
15. The composition according to claim 1 , wherein said C6-C8 aromatic ethers of C2-C9 polyols are chosen from ethylene glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monophenyl ether, propylene glycol monobenzyl ether, diethylene glycol monophenyl ether and diethylene glycol monobenzyl ether.
16. The composition according to claim 1 , wherein said at least one cationic direct dye is present in an amount ranging from 0.001 to 10% by weight relative to the total weight of the composition.
17. The composition according to claim 16 , wherein said at least one cationic direct dye is present in an amount ranging from 0.005 to 5% by weight relative to the total weight of the composition.
18. The composition according to claim 1 , wherein said at least one compound chosen from polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols is present in an amount ranging from 0.1 to 40% by weight relative to the total weight of the composition.
19. The composition according to claim 18 , wherein said at least one compound is present in an amount ranging from 0.5 to 20% by weight relative to the total weight of the composition.
20. The composition according to claim 1 , wherein said composition further comprises additional direct dyes.
21. The composition according to claim 1 , wherein said composition further comprises water.
22. The composition according to claim 21 , wherein composition further comprises at least one organic solvent other than polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols.
23. The composition according claim 1 , wherein said composition has a pH ranging from 2 to 11.
24. The composition according to claim 23 , wherein said pH ranges from 5 to 10.
25. The composition according to claim 1 , wherein said composition further comprises at least one oxidizing agent.
26. A process for the direct dyeing of keratin fibers, comprising applying to said fibers, for a period which is sufficient to develop the desired coloration, at least one composition for the direct dyeing of keratin fibers comprising:
(i) at least one cationic direct dye chosen from those of formulae (I), (II), (III) and (III′) below:
in which formula (I):
D is chosen from a nitrogen atom and a —CH group,
R1 and R2, which may be identical or different, are chosen from a hydrogen atom, C1-C4 alkyl radicals having a substituent chosen from —CN, —OH, and —NH2 radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C1-C4 alkyl radicals,
R3and R′3, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C1-C4 alkoxy, C1-C4 alkyl, and acetyloxy radicals,
X− is an anion,
A is a group chosen from structures A1 to A18 below:
in which R4 is chosen from C1-C4 alkyl radicals which can be substituted with a hydroxyl radical and R5 is chosen from C1-C4 alkoxy radicals, with the proviso that when D is —CH, when A is A4 or A13 and when R3 is other than an alkoxy radical, then R1 and R2 are not simultaneously a hydrogen atom;
in which formula (II):
R6 is chosen from a hydrogen atom and C1-C4 alkyl radicals,
R7 is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R6, a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C1-C 4 alkyl radicals,
R8 and R9, which may be identical or different, are chosen from a hydrogen atom, halogen atoms, and C1-C4 alkyl, C1-C4 alkoxy, and —CN radicals,
X− is an anion,
B is a group chosen from structures B1 to B6 below:
in which R10 is chosen from C1-C4 alkyl radicals, and R11 and R12, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals;
in which formulae (III) and (III′):
R13 is chosen from a hydrogen atom, C1-C4 alkoxy radicals, halogen atoms chosen from bromine, chlorine, iodine and fluorine and unsubstituted and substituted amino radicals,
R14 is chosen from a hydrogen atom, and C1-C4 alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C1-C4 alkyl radicals,
R15 is chosen from a hydrogen atom and halogen atoms chosen from bromine, chlorine, iodine and fluorine,
R16 and R17, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals,
D1 and D2, which may be identical or different, are chosen from a nitrogen atom and a —CH group,
m is 0 or 1,
it being understood that when R13 is an unsubstituted amino radical, then D1 and D2 are simultaneously a —CH group and m is 0,
X− is an anion,
E is a group chosen from structures E1 to E8 below:
in which R′ is chosen from C1-C4 alkyl radicals;
when m is 0 and when D1 is a nitrogen atom, then E can also be a group of structure E9 below:
in which R′ is chosen from C1-C4 alkyl radicals; and
(ii) at least one compound chosen from polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols,
said composition being free of oxidases or oxidoreductases, and
rinsing the fibers, optionally washing said fibers with shampoo, then rinsing again and drying.
27. A process for dyeing keratin fibers according to claim 26 , wherein said keratin fibers are human keratin fibers.
28. A process for dyeing keratin fibers according to claim 27 , wherein said human keratin fibers are hair.
29. A process for the direct dyeing of keratin fibers according to claim 26 , wherein said fibers are not rinsed a second time before drying.
30. A process for the direct dyeing of keratin fibers comprising:
separately storing a first composition comprising
(i) at least one cationic direct dye chosen from those of formulae (I), (II), (III) and (III′) below:
in which formula (I):
D is chosen from a nitrogen atom and a —CH group,
R1 and R2, which may be identical or different, are chosen from a hydrogen atom, C1-C4 alkyl radicals having a substituent chosen from —CN, —OH, and —NH2 radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C1-C4 alkyl radicals,
R3 and R′3, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C1-C4 alkoxy, C1-C4 alkyl, and acetyloxy radicals,
X− is an anion,
A is a group chosen from structures A1 to A18 below:
in which R4 is chosen from C1-C4 alkyl radicals which can be substituted with a hydroxyl radical and R5 is chosen from C1-C4 alkoxy radicals, with the proviso that when D is —CH, when A is A4 or A13 and when R3 is other than an alkoxy radical, then R1 and R2 are not simultaneously a hydrogen atom;
in which formula (II):
R6 is chosen from a hydrogen atom and C1-C4 alkyl radicals,
R7 is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R6, a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C1-C4 alkyl radicals,
R8 and R9, which may be identical or different, are chosen from a hydrogen atom, halogen atoms, and C1-C4 alkyl, C1-C4 alkoxy, and —CN radicals,
X− is an anion,
B is a group chosen from structures B1 to B6 below:
in which R10 is chosen from C1-C4 alkyl radicals, and R11 and R12, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals;
in which formulae (III) and (III′):
R13 is chosen from a hydrogen atom, C1-C4 alkoxy radicals, halogen atoms chosen from bromine, chlorine, iodine and fluorine and unsubstituted and substituted amino radicals,
R14 is chosen from a hydrogen atom, and C1-C4 alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C1-C4 alkyl radicals,
R15 is chosen from a hydrogen atom and halogen atoms chosen from bromine, chlorine, iodine and fluorine,
R16 and R17, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals,
D1 and D2, which may be identical or different, are chosen from a nitrogen atom and a —CH group,
m is 0 or 1,
it being understood that when R13 is an unsubstituted amino radical, then D1 and D2 are simultaneously a —CH group and m is 0,
X− is an anion,
E is a group chosen from structures E1 to E8 below:
in which R′ is chosen from C1-C4 alkyl radicals;
when m is 0 and when D1 is a nitrogen atom, then E can also be a group of structure E9 below:
in which R′ is chosen from C1-C4 alkyl radicals; and
(ii) at least one compound chosen from polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols;
separately storing a second composition comprising at least one oxidizing agent other than oxidases or oxidoreductases and
thereafter mixing said first composition with said second composition and applying this mixture to said keratin fibers, wherein said first or said second composition additionally comprises at least one compound chosen from polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols.
31. A multi-compartment dyeing kit comprising at least two separate
compartments wherein a first compartment contains a composition comprising: at least one cationic direct dye chosen from those of formulae (I), (II), (III) and (III′) below:
in which formula (I):
D is chosen from a nitrogen atom and a —CH group,
R1 and R2, which may be identical or different, are chosen from a hydrogen atom, C1-C4 alkyl radicals having a substituent chosen from —CN, —OH, and —NH2 radicals, and a 4′-aminophenyl radical; or form, with a carbon atom of the benzene ring, a nitrogenous heterocycle, optionally oxygenated and optionally having at least one substituent chosen from C1-C4 alkyl radicals,
R3 and R′3, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, and cyano, C1-C4 alkoxy, C1-C4 alkyl, and acetyloxy radicals,
X− is an anion,
A is a group chosen from structures A1 to A18 below:
in which R4 is chosen from C1-C4 alkyl radicals which can be substituted with a hydroxyl radical and R5 is chosen from C1-C4 alkoxy radicals, with the proviso that when D is —CH, when A is A4 or A13 and when R3 is other than an alkoxy radical, then R1 and R2 are not simultaneously a hydrogen atom;
in which formula (II):
R6 is chosen from a hydrogen atom and C1-C4 alkyl radicals,
R7 is chosen from a hydrogen atom, alkyl radicals having a substituent chosen from —CN and amino radicals, and a 4′-aminophenyl radical, or forms, with R6, a nitrogenous heterocycle optionally oxygenated and optionally having a substituent chosen from C1-C4 alkyl radicals,
R8 and R9, which may be identical or different, are chosen from a hydrogen atom, halogen atoms, and C1-C4 alkyl, C1-C4 alkoxy, and —CN radicals,
X− is an anion,
B is a group chosen from structures B1 to B6 below:
in which R10 is chosen from C1-C4 alkyl radicals, and R11and R12, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals;
in which formulae (III) and (III′):
R13 is chosen from a hydrogen atom, C1-C4 alkoxy radicals, halogen atoms chosen from bromine, chlorine, iodine and fluorine and unsubstituted and substituted amino radicals,
R14 is chosen from a hydrogen atom, and C1-C4 alkyl radicals or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and optionally has a substituent chosen from C1-C4 alkyl radicals,
R15 is chosen from a hydrogen atom and halogen atoms chosen from bromine, chlorine, iodine and fluorine,
R16 and R17, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals,
D1 and D2, which may be identical or different, are chosen from a nitrogen atom and a —CH group,
m is 0 or 1,
it being understood that when R13 is an unsubstituted amino radical, then D1 and D2 are simultaneously a —CH group and m is 0,
X− is an anion,
E is a group chosen from structures E1 to E8 below:
in which R′ is chosen from C1-C4 alkyl radicals;
when m is 0 and when D1 is a nitrogen atom, then E can also be a group of structure E9 below:
in which R′ is chosen from C1-C4 alkyl radicals; and
a second compartment contains a composition comprising at least one oxidizing agent other than oxidases or oxidoreductases, wherein either the composition in the first compartment or the composition in the second compartment additionally comprises at least one compound chosen from polyols, C1-C8 aliphatic ethers of C3-C9 polyols, and C6-C8 aromatic ethers of C2-C9 polyols.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9806751 | 1998-05-28 | ||
| FR9806751A FR2779055B1 (en) | 1998-05-28 | 1998-05-28 | DIRECT DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND POLYOL AND / OR POLYOL ETHER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20020002748A1 true US20020002748A1 (en) | 2002-01-10 |
| US6436153B2 US6436153B2 (en) | 2002-08-20 |
Family
ID=9526824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/321,890 Expired - Lifetime US6436153B2 (en) | 1998-05-28 | 1999-05-28 | Composition for the direct dyeing of keratin fibres with a cationic direct dye and a polyol and/or a polyol ether |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6436153B2 (en) |
| EP (1) | EP0962219B2 (en) |
| JP (1) | JP3814442B2 (en) |
| KR (1) | KR100329413B1 (en) |
| CN (1) | CN1217648C (en) |
| AT (1) | ATE278378T1 (en) |
| AU (1) | AU722600B2 (en) |
| BR (1) | BR9901829B1 (en) |
| CA (1) | CA2273416C (en) |
| DE (1) | DE69920801T3 (en) |
| ES (1) | ES2230815T5 (en) |
| FR (1) | FR2779055B1 (en) |
| HU (1) | HUP9901746A3 (en) |
| MX (1) | MX221183B (en) |
| PL (1) | PL204182B1 (en) |
| PT (1) | PT962219E (en) |
| RU (1) | RU2166930C2 (en) |
| ZA (1) | ZA993199B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030177591A1 (en) * | 2000-10-12 | 2003-09-25 | Peter Mockli | Method of dyeing keratin-containing fibers |
| US20040093676A1 (en) * | 2001-04-03 | 2004-05-20 | Laurent Vidal | Novel dyeing composition for dyeing keratinous fibres comprising a particular dicationic monoazo dye |
| US20040187225A1 (en) * | 2001-04-02 | 2004-09-30 | Laurent Vidal | Novel dyeing composition for dyeing keratinous fibres comprising a particular dicationic diazo dye |
| US20040244125A1 (en) * | 2001-10-10 | 2004-12-09 | Peter Mockli | Method of dyeing keratin-containing fibres |
| WO2005115322A1 (en) * | 2004-05-19 | 2005-12-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of special polyols for inhibiting the crystallization of onium aldehydes and onium ketones |
| US20070125261A1 (en) * | 2005-08-26 | 2007-06-07 | Nicolas Daubresse | Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing |
| EP3153153A4 (en) * | 2014-06-06 | 2017-11-15 | Kao Corporation | Hair-dye composition |
| US20180331670A1 (en) * | 2017-05-11 | 2018-11-15 | Eagantu Ltd. | Compact band pass filter |
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| FR2853236B1 (en) * | 2003-04-01 | 2007-10-12 | Oreal | COLORING COMPOSITION FOR HUMAN KERATINIC MATERIALS COMPRISING A FLUORESCENT COLORANT AND A POLYOL, METHOD AND USE |
| US7192454B2 (en) * | 2003-04-01 | 2007-03-20 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof |
| US7147673B2 (en) * | 2003-04-01 | 2006-12-12 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof |
| US7204860B2 (en) * | 2003-04-01 | 2007-04-17 | L'oreal | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof |
| US7250064B2 (en) * | 2003-04-01 | 2007-07-31 | L'oreal S.A. | Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof |
| US7195650B2 (en) * | 2003-04-01 | 2007-03-27 | L'oreal S.A. | Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye |
| US7303589B2 (en) | 2003-04-01 | 2007-12-04 | L'oreal S.A. | Process for dyeing human keratin fibers, having a lightening effect, comprising at least one fluorescent compound and compositions of the same |
| US7208018B2 (en) * | 2003-04-01 | 2007-04-24 | L'oreal | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof |
| US7195651B2 (en) * | 2003-04-01 | 2007-03-27 | L'oreal S.A. | Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor |
| US20040244126A1 (en) * | 2003-06-04 | 2004-12-09 | Vena Lou Ann Christine | Method, compositions, and kit for coloring hair |
| US20050125913A1 (en) | 2003-12-11 | 2005-06-16 | Saroja Narasimhan | Method and compositions for coloring hair |
| JP2008512498A (en) * | 2004-09-13 | 2008-04-24 | ロレアル | POSS-containing cosmetic composition having improved adhesion and / or flexibility and method for producing improved cosmetic composition |
| KR20090015113A (en) | 2006-06-13 | 2009-02-11 | 시바 홀딩 인코포레이티드 | Tricationic dyes |
| RU2680068C2 (en) | 2013-09-02 | 2019-02-14 | Л'Ореаль | Method for dyeing keratin fibres using cationic styryl disulphide dyes, and composition including said dyes |
| WO2017194151A1 (en) | 2016-05-12 | 2017-11-16 | Hewlett-Packard Development Company, L.P. | Build material containers |
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-
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- 1998-05-28 FR FR9806751A patent/FR2779055B1/en not_active Expired - Lifetime
-
1999
- 1999-05-05 PT PT99401099T patent/PT962219E/en unknown
- 1999-05-05 AT AT99401099T patent/ATE278378T1/en active
- 1999-05-05 EP EP99401099A patent/EP0962219B2/en not_active Expired - Lifetime
- 1999-05-05 DE DE69920801T patent/DE69920801T3/en not_active Expired - Lifetime
- 1999-05-05 ES ES99401099T patent/ES2230815T5/en not_active Expired - Lifetime
- 1999-05-10 ZA ZA9903199A patent/ZA993199B/en unknown
- 1999-05-12 AU AU28082/99A patent/AU722600B2/en not_active Ceased
- 1999-05-21 MX MX9904753A patent/MX221183B/en not_active IP Right Cessation
- 1999-05-25 BR BRPI9901829-2B1A patent/BR9901829B1/en active IP Right Grant
- 1999-05-26 KR KR19990019063A patent/KR100329413B1/en not_active IP Right Cessation
- 1999-05-27 CA CA002273416A patent/CA2273416C/en not_active Expired - Fee Related
- 1999-05-27 PL PL333399A patent/PL204182B1/en not_active IP Right Cessation
- 1999-05-27 HU HU9901746A patent/HUP9901746A3/en unknown
- 1999-05-27 CN CN991092465A patent/CN1217648C/en not_active Expired - Fee Related
- 1999-05-27 RU RU99111265/14A patent/RU2166930C2/en not_active IP Right Cessation
- 1999-05-28 JP JP14911399A patent/JP3814442B2/en not_active Expired - Lifetime
- 1999-05-28 US US09/321,890 patent/US6436153B2/en not_active Expired - Lifetime
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030177591A1 (en) * | 2000-10-12 | 2003-09-25 | Peter Mockli | Method of dyeing keratin-containing fibers |
| US20040187225A1 (en) * | 2001-04-02 | 2004-09-30 | Laurent Vidal | Novel dyeing composition for dyeing keratinous fibres comprising a particular dicationic diazo dye |
| US6884265B2 (en) | 2001-04-02 | 2005-04-26 | L'oreal S.A. | Dyeing composition for dyeing keratinous fibers comprising at least one particular dicationic diazo dye |
| US7060110B2 (en) | 2001-04-03 | 2006-06-13 | L'oreal | Dyeing composition for dyeing keratinous fibres comprising a particular dicationic monoazo dye |
| US20040093676A1 (en) * | 2001-04-03 | 2004-05-20 | Laurent Vidal | Novel dyeing composition for dyeing keratinous fibres comprising a particular dicationic monoazo dye |
| US20040244125A1 (en) * | 2001-10-10 | 2004-12-09 | Peter Mockli | Method of dyeing keratin-containing fibres |
| US7354572B2 (en) | 2001-10-10 | 2008-04-08 | Ciba Specialty Chemicals Corp. | Method of dyeing keratin-containing fibres |
| WO2005115322A1 (en) * | 2004-05-19 | 2005-12-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of special polyols for inhibiting the crystallization of onium aldehydes and onium ketones |
| US20070125261A1 (en) * | 2005-08-26 | 2007-06-07 | Nicolas Daubresse | Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing |
| US7582122B2 (en) | 2005-08-26 | 2009-09-01 | L'oreal S.A. | Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing |
| EP3153153A4 (en) * | 2014-06-06 | 2017-11-15 | Kao Corporation | Hair-dye composition |
| US10485747B2 (en) | 2014-06-06 | 2019-11-26 | Kao Corporation | Hair-dye composition |
| US20180331670A1 (en) * | 2017-05-11 | 2018-11-15 | Eagantu Ltd. | Compact band pass filter |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0962219A3 (en) | 2000-03-08 |
| PL204182B1 (en) | 2009-12-31 |
| CA2273416A1 (en) | 1999-11-28 |
| HUP9901746A3 (en) | 2000-11-28 |
| EP0962219A2 (en) | 1999-12-08 |
| ES2230815T3 (en) | 2005-05-01 |
| ES2230815T5 (en) | 2011-01-20 |
| FR2779055B1 (en) | 2001-05-04 |
| US6436153B2 (en) | 2002-08-20 |
| PT962219E (en) | 2005-02-28 |
| ZA993199B (en) | 1999-11-15 |
| HUP9901746A2 (en) | 2000-07-28 |
| EP0962219B1 (en) | 2004-10-06 |
| EP0962219B2 (en) | 2010-08-04 |
| BR9901829A (en) | 2000-05-30 |
| FR2779055A1 (en) | 1999-12-03 |
| DE69920801T3 (en) | 2011-02-17 |
| ATE278378T1 (en) | 2004-10-15 |
| PL333399A1 (en) | 1999-12-06 |
| AU2808299A (en) | 1999-12-09 |
| DE69920801D1 (en) | 2004-11-11 |
| JPH11349458A (en) | 1999-12-21 |
| RU2166930C2 (en) | 2001-05-20 |
| HU9901746D0 (en) | 1999-08-30 |
| KR100329413B1 (en) | 2002-03-20 |
| CN1237409A (en) | 1999-12-08 |
| JP3814442B2 (en) | 2006-08-30 |
| CA2273416C (en) | 2006-12-12 |
| BR9901829B1 (en) | 2013-06-18 |
| KR19990088571A (en) | 1999-12-27 |
| CN1217648C (en) | 2005-09-07 |
| MX221183B (en) | 2004-06-29 |
| AU722600B2 (en) | 2000-08-10 |
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