RU98122213A - METHOD OF DIRECT PAINTING OF KERATIN FIBERS IN TWO STEPS OF DIRECT BASIC DYES - Google Patents
METHOD OF DIRECT PAINTING OF KERATIN FIBERS IN TWO STEPS OF DIRECT BASIC DYESInfo
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- RU98122213A RU98122213A RU98122213/14A RU98122213A RU98122213A RU 98122213 A RU98122213 A RU 98122213A RU 98122213/14 A RU98122213/14 A RU 98122213/14A RU 98122213 A RU98122213 A RU 98122213A RU 98122213 A RU98122213 A RU 98122213A
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- carbon atoms
- radical
- group
- alkyl radical
- hydrogen atom
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- 239000000835 fiber Substances 0.000 title claims 8
- 102000011782 Keratins Human genes 0.000 title claims 7
- 108010076876 Keratins Proteins 0.000 title claims 7
- 239000000981 basic dye Substances 0.000 title claims 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims 50
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 20
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 239000000975 dye Substances 0.000 claims 10
- -1 alkali metal bromates Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 238000004040 coloring Methods 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000011630 iodine Substances 0.000 claims 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 5
- 239000000843 powder Substances 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 4
- 150000001450 anions Chemical class 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 4
- 230000001590 oxidative Effects 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 238000004061 bleaching Methods 0.000 claims 3
- 239000000982 direct dye Substances 0.000 claims 3
- 238000002845 discoloration Methods 0.000 claims 3
- 125000005842 heteroatoms Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N iodine atom Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 150000002829 nitrogen Chemical group 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- WIJOZBDYRBXOOW-UHFFFAOYSA-N [8-[(4-amino-2-nitrophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1[N+]([O-])=O WIJOZBDYRBXOOW-UHFFFAOYSA-N 0.000 claims 2
- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atoms Chemical group 0.000 claims 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000000306 component Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-Naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 229940106189 Ceramides Drugs 0.000 claims 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N Hydrogen peroxide - urea Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims 1
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims 1
- 241000158728 Meliaceae Species 0.000 claims 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N Neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 claims 1
- RFQSMLBZXQOMKK-UHFFFAOYSA-N [3-[(4,8-diamino-6-bromo-1,5-dioxonaphthalen-2-yl)amino]phenyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC(NC=2C(C3=C(N)C=C(Br)C(=O)C3=C(N)C=2)=O)=C1 RFQSMLBZXQOMKK-UHFFFAOYSA-N 0.000 claims 1
- HSWXSHNPRUMJKI-UHFFFAOYSA-N [8-[(2-methoxyphenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].COC1=CC=CC=C1N\N=C/1C2=CC([N+](C)(C)C)=CC=C2C=CC\1=O HSWXSHNPRUMJKI-UHFFFAOYSA-N 0.000 claims 1
- CMPPYVDBIJWGCB-UHFFFAOYSA-N [8-[(4-amino-3-nitrophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N\NC1=CC=C(N)C([N+]([O-])=O)=C1 CMPPYVDBIJWGCB-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 230000000111 anti-oxidant Effects 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- 150000001783 ceramides Chemical class 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- 230000003750 conditioning Effects 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000000490 cosmetic additive Substances 0.000 claims 1
- 238000009967 direct dyeing Methods 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 230000002335 preservative Effects 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- GRYBZNLNHVSHPY-UHFFFAOYSA-N sodium;4-hydroxy-5-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]naphthalene-2,7-disulfonic acid Chemical compound [Na+].C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1NC=C1C=CC=CC1=O GRYBZNLNHVSHPY-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- NWKBFCIAPOSTKG-UHFFFAOYSA-M trimethyl-[3-[(3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)diazenyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC([N+](C)(C)C)=C1 NWKBFCIAPOSTKG-UHFFFAOYSA-M 0.000 claims 1
- 0 Cc1*(CO)*c[n]1 Chemical compound Cc1*(CO)*c[n]1 0.000 description 2
- UJUIGRLCOGSWIQ-UHFFFAOYSA-N Cc1c(CO)cc[nH]1 Chemical compound Cc1c(CO)cc[nH]1 UJUIGRLCOGSWIQ-UHFFFAOYSA-N 0.000 description 1
Claims (19)
в которой D означает атом азота или группу -СН; R1 и R2, одинаковые или разные, означают атом водорода; алкильный радикал с 1-4 атомами углерода, который может быть замещен радикалом -CN, -ОН или -NH2, или вместе с атомом углерода бензольного цикла образуют возможно содержащий кислород или азот гетероцикл, который может быть замещен одним или несколькими алкильными радикалами с 1-4 атомами углерода; 4'-аминофенильный радикал; R3 и R'3, одинаковые или разные, означают атом водорода или атом галогена, выбираемый среди атомов хлора, брома, иода и фтора; цианогруппу, алкоксил с 1-4 атомами углерода или ацетилоксигруппу; X- означает анион, предпочтительно выбираемый среди хлор-аниона, метилсульфат-аниона и ацетат-аниона; А означает группу, выбираемую среди следующих структур A1 - A19
в которых R4 означает алкильный радикал с 1-4 атомами углерода, который может быть замещен гидроксилом, и R5 означает алкоксил с 1-4 атомами углерода;
при условии, что, когда D означает группу -СН, А означает А4 или A13 и R3 отличается от алкоксила, тогда R1 и R2 одновременно не означают атом водорода; б) соединения следующей формулы (II)
в которой: R6 означает атом водорода или алкильный радикал с 1-4 атомами углерода; R7 означает атом водорода, алкильный радикал, который может быть замещен радикалом -CN или аминогруппой; 4'-аминофенильный радикал или вместе с R6 образует возможно содержащий кислород и/или азот гетероцикл, который может быть замещен алкильным радикалом с 1-4 атомами углерода; R8 и R9, одинаковые или разные, означают атом водорода, атом галогена, такой, как атом брома, хлора, иода или фтора; алкильный радикал с 1-4 атомами углерода или алкоксил с 1-4 атомами углерода; радикал -CN; Х- означает анион, предпочтительно выбираемый среди хлор-аниона, метилсульфат-аниона и ацетат-аниона; В означает группу, выбираемую среди следующих структур В1 - B6:
в которых R10 означает алкильный радикал с 1-4 атомами углерода, R11 и R12, одинаковые или разные, означают атом водорода или алкильный радикал с 1-4 атомами углерода; в) соединения следующих формул (III) и (III')
в которых R13 означает атом водорода, алкоксил с 1-4 атомами углерода, атом галогена, такой, как атом брома, хлора, иода или фтора, или аминогруппу; R14 означает атом водорода, алкильный радикал с 1-4 атомами углерода или вместе с атомом углерода бензольного цикла образует гетероцикл, возможно содержащий кислород, и/или замещенный одной или несколькими алкильными группами с 1-4 атомами углерода; R15 означает атом водорода или атом галогена, такой, как атом брома, хлора, иода или фтора; R16 и R17, одинаковые или разные, означают атом водорода или алкильный радикал с 1-4 атомами углерода; D1 и D2, одинаковые или разные, означают атом азота или группу -СН; m означает 0 или 1;
при условии, что, когда R13 означает незамещенную аминогруппу, тогда D1 и D2 одновременно означают группу -СН и m = 0; X- означает анион, предпочтительно выбираемый среди хлор-аниона, метилсульфат-аниона и ацетат-аниона; Е означает группу, выбираемую среди следующих структур Е1 - Е8
в которых R' означает алкильный радикал с 1-4 атомами углерода;
причем, когда m = 0 и D1 означает атом азота, тогда Е также может означать группу следующей структуры Е9
в которой R' означает алкильный радикал с 1-4 атомами углерода; г) соединения следующей формулы (IV)
G-N=N-J
в которой: символ G означает группу, выбираемую среди следующих структур G1-G3
в которых R18 означает алкильный радикал с 1-4 атомами углерода, фенил, который может быть замещен алкильным радикалом с 1-4 атомами углерода или атомом галогена, выбираемым среди атомов хлора, брома, иода или фтора; R19 означает алкильный радикал с 1-4 атомами углерода или фенил; R20 и R21, одинаковые или разные, означают алкильный радикал с 1-4 атомами углерода, фенил, или в случае G1 вместе образуют бензольный цикл, замещенный одним или несколькими алкильными радикалами с 1-4 атомами углерода, алкоксильными радикалами с 1-4 атомами углерода или NO2, или в случае G2 вместе образуют бензольный цикл, возможно замещенный одним или несколькими алкильными радикалами с 1-4 атомами углерода, алкоксильными радикалами с 1-4 атомами углерода или NO2; R20 может означать, кроме того, атом водорода; Z означает атом кислорода, серы или группу -NR19; М означает группу -СН, -CR (где R означает алкил с 1-4 атомами углерода) или группу -NR22(X-)r; К означает группу -СН, -CR (где R означает алкил с 1-4 атомами углерода) или группу -NR22(X-)r; Р означает группу -СН, -CR (где R означает алкил с 1-4 атомами углерода) или группу -NR22(X-)r; r означает нуль или 1; R22 означает атом О-, алкоксил с 1-4 атомами углерода или алкильный радикал с 1-4 атомами углерода; R23 и R24, одинаковые или разные, означают атом водорода или атом галогена, выбираемый среди атомов хлора, брома, иода и фтора; алкильный радикал с 1-4 атомами углерода, алкоксил с 1-4 атомами углерода, радикал -NO2; X- означает анион, предпочтительно выбираемый среди хлор-аниона, иод-аниона, метилсульфат-аниона, этилсульфат-аниона, ацетат-аниона и перхлорат-аниона; при условии, что если R22 означает О-, то r означает нуль; если К или Р или М означают -N-(С1-С4)-алкил-Х-, то R23 или R24,
отличается от атома водорода; если К означает -NR22(X-)r, то М=Р=-СН, -CR; если М означает -NR22(X-)r, то К= Р= -СН, -CR; если Р означает -NR22(X-)r, то К= М и означают -СН или -CR; если Z означает атом серы, R21 означает алкил с 1-4 атомами углерода, то R20 отличается от атома водорода; если Z означает -NR22, R19 означает алкил с 1-4 атомами углерода, то по крайней мере один из радикалов R18, R20 или R21 группы со структурой G2 отличается от алкильного радикала с 1-4 атомами углерода; символ J означает: - (а) группу следующей структуры J1
в которой R25 означает атом водорода, атом галогена, выбираемый среди атомов хлора, брома, иода и фтора; алкильный радикал с 1-4 атомами углерода, алкокси-радикал с 1-4 атомами углерода, гидроксил, нитрогруппу, радикал -NHR28, -NR29R30, -NHCOалкил с 1-4 атомами углерода или вместе с R26 образует пяти- или шестичленный цикл, содержащий или нет один или несколько гетероатомов, выбираемых среди атомов азота, кислорода или серы; R26 означает атом водорода, атом галогена, выбираемый среди атомов хлора, брома, иода и фтора; алкильный радикал с 1-4 атомами углерода, алкоксил с 1-4 атомами углерода, или вместе с R27 или R28 образует пяти- или шестичленный цикл, содержащий или нет один или несколько гетероатомов, выбираемых среди атомов азота, кислорода или серы; R27 означает атом водорода, гидроксил, радикал -NHR28, радикал -NR29R30; R28 означает атом водорода, алкильный радикал с 1-4 атомами углерода, моногидроксиалкильный радикал с 1-4 атомами углерода, полигидроксиалкильный радикал с 2-4 атомами углерода, фенил; R29 и R30, одинаковые или разные, означают алкильный радикал с 1-4 атомами углерода, моногидроксиалкильный радикал с 1-4 атомами углерода, полигидроксиалкильный радикал с 2-4 атомами углерода; -(б) азотсодержащую пяти- или шестичленную гетероциклическую группу, которая может включать другие гетероатомы и/или карбонилированные группы и может быть замещена одним или несколькими алкильными радикалами с 1-4 атомами углерода, аминогруппами или фенильными радикалами, и особенно группу следующей структуры J2
в которой R31 и R32, одинаковые или разные, означают атом водорода, алкильный радикал с 1-4 атомами углерода, фенил; Y означает радикал -СО- или радикал
n означает 0 или 1, причем, если n означает 1, то U означает радикал -СО-.13. A method according to any one of claims. 1-10, characterized in that the main direct dye or main direct dyes are selected from the following compounds: a) compounds of the following formula (I)
in which D represents a nitrogen atom or a —CH group; R 1 and R 2 , which are the same or different, represent a hydrogen atom; an alkyl radical with 1-4 carbon atoms, which may be substituted by the radical -CN, -OH or -NH 2 , or together with the carbon atom of the benzene ring form a heterocycle containing oxygen or nitrogen that may be replaced by one or more alkyl radicals with 1 -4 carbon atoms; 4'-aminophenyl radical; R 3 and R ' 3 , which are the same or different, represent a hydrogen atom or a halogen atom selected among chlorine, bromine, iodine and fluorine atoms; cyano, alkoxy with 1-4 carbon atoms or acetyloxy; X - means an anion, preferably chosen among the chlorine anion, methyl sulfate anion and acetate anion; A means a group selected among the following structures A 1 - A 19
in which R 4 means an alkyl radical with 1-4 carbon atoms, which may be substituted by hydroxyl, and R 5 means alkoxy with 1-4 carbon atoms;
with the proviso that when D means the group —CH, A means A 4 or A 13 and R 3 is different from alkoxy, then R 1 and R 2 do not simultaneously mean a hydrogen atom; b) compounds of the following formula (II)
in which: R 6 means a hydrogen atom or an alkyl radical with 1-4 carbon atoms; R 7 means a hydrogen atom, an alkyl radical which may be substituted by a —CN radical or an amino group; 4'-aminophenyl radical or, together with R 6, forms a heterocycle containing possibly oxygen and / or nitrogen, which may be substituted by an alkyl radical with 1-4 carbon atoms; R 8 and R 9 , which are the same or different, represent a hydrogen atom, a halogen atom, such as a bromine, chlorine, iodine or fluorine atom; an alkyl radical with 1-4 carbon atoms or alkoxy with 1-4 carbon atoms; the radical-CN; X - means an anion, preferably selected among the chlorine anion, methyl sulfate anion and acetate anion; B means a group selected among the following structures B1 - B6:
in which R 10 is an alkyl radical with 1-4 carbon atoms, R 11 and R 12 are the same or different, a hydrogen atom or an alkyl radical with 1-4 carbon atoms; C) compounds of the following formulas (III) and (III ')
in which R 13 means a hydrogen atom, alkoxy with 1-4 carbon atoms, a halogen atom such as a bromine, chlorine, iodine or fluorine atom, or an amino group; R 14 means a hydrogen atom, an alkyl radical with 1-4 carbon atoms or together with the carbon atom of the benzene ring forms a heterocycle, possibly containing oxygen, and / or substituted by one or more alkyl groups with 1-4 carbon atoms; R 15 means a hydrogen atom or a halogen atom, such as a bromine, chlorine, iodine or fluorine atom; R 16 and R 17 , which are the same or different, represent a hydrogen atom or an alkyl radical with 1-4 carbon atoms; D 1 and D 2 , the same or different, represent a nitrogen atom or a —CH group; m is 0 or 1;
with the proviso that when R 13 is an unsubstituted amino group, then D 1 and D 2 simultaneously denote the group —CH and m = 0; X - means an anion, preferably chosen among the chlorine anion, methyl sulfate anion and acetate anion; E means a group selected among the following structures E1 - E8
in which R 'denotes an alkyl radical with 1-4 carbon atoms;
moreover, when m = 0 and D 1 means a nitrogen atom, then E can also mean a group of the following structure E9
in which R 'denotes an alkyl radical with 1-4 carbon atoms; g) compounds of the following formula (IV)
GN = NJ
in which: the symbol G means a group selected among the following structures G 1 -G 3
in which R 18 means an alkyl radical with 1-4 carbon atoms, phenyl, which can be substituted with an alkyl radical with 1-4 carbon atoms or a halogen atom selected from chlorine, bromine, iodine or fluorine atoms; R 19 means an alkyl radical with 1-4 carbon atoms or phenyl; R 20 and R 21 , the same or different, mean an alkyl radical with 1-4 carbon atoms, phenyl, or in the case of G 1 together form a benzene cycle, substituted by one or more alkyl radicals with 1-4 carbon atoms, alkoxy radicals with 1- 4 carbon atoms or NO 2 , or in the case of G 2 together form a benzene cycle, possibly substituted by one or more alkyl radicals with 1-4 carbon atoms, alkoxy radicals with 1-4 carbon atoms or NO 2 ; R 20 may also mean a hydrogen atom; Z represents an oxygen atom, a sulfur or the group —NR 19 ; M represents an —CH group; —CR (where R is alkyl with 1-4 carbon atoms) or —NR 22 (X - ) r ; K means a group —CH — —CR (where R is alkyl with 1-4 carbon atoms) or a group —NR 22 (X - ) r ; P means a group —CH — —CR (where R is alkyl with 1-4 carbon atoms) or a group —NR 22 (X - ) r ; r is zero or 1; R 22 means an atom O - , alkoxy with 1-4 carbon atoms or an alkyl radical with 1-4 carbon atoms; R 23 and R 24 , which are the same or different, represent a hydrogen atom or a halogen atom selected from chlorine, bromine, iodine and fluorine atoms; alkyl radical with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, radical -NO 2 ; X - means an anion, preferably selected among chlorine anion, iodine anion, methyl sulfate anion, ethyl sulfate anion, acetate anion and perchlorate anion; provided that if R 22 is O - , then r is zero; if K or P or M means -N- (C 1 -C 4 ) -alkyl-X - , then R 23 or R 24 ,
different from the hydrogen atom; if K means -NR 22 (X - ) r , then M = P = -CH, -CR; if M means -NR 22 (X - ) r , then K = P = -CH, -CR; if P means -NR 22 (X - ) r , then K = M and means-CH or-CR; if Z is a sulfur atom, R 21 is alkyl with 1-4 carbon atoms, then R 20 is different from a hydrogen atom; if Z is —NR 22 , R 19 is alkyl with 1-4 carbon atoms, then at least one of the radicals R 18 , R 20 or R 21 groups with the structure of G 2 is different from the alkyl radical with 1-4 carbon atoms; symbol J means: - (a) a group of the following structure J 1
in which R 25 means a hydrogen atom, a halogen atom selected among the atoms of chlorine, bromine, iodine and fluorine; alkyl radical with 1-4 carbon atoms, alkoxy radical with 1-4 carbon atoms, hydroxyl, nitro group, radical —NHR 28 , —NR 29 R 30 , —NHCO alkyl with 1-4 carbon atoms or together with R 26 forms five or a six-membered cycle, containing or not one or more heteroatoms selected from nitrogen, oxygen or sulfur; R 26 means a hydrogen atom, a halogen atom selected from among chlorine, bromine, iodine and fluorine atoms; an alkyl radical with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, or together with R 27 or R 28 forms a five- or six-membered cycle, containing or not one or more heteroatoms selected among nitrogen, oxygen or sulfur; R 27 means a hydrogen atom, hydroxyl, a radical —NHR 28 , a radical —NR 29 R 30 ; R 28 means a hydrogen atom, an alkyl radical with 1-4 carbon atoms, a monohydroxyalkyl radical with 1-4 carbon atoms, a polyhydroxyalkyl radical with 2-4 carbon atoms, phenyl; R 29 and R 30 , the same or different, mean an alkyl radical with 1-4 carbon atoms, a monohydroxyalkyl radical with 1-4 carbon atoms, a polyhydroxyalkyl radical with 2-4 carbon atoms; - (b) a nitrogen-containing five- or six-membered heterocyclic group, which may include other heteroatoms and / or carbonylated groups and may be substituted by one or more alkyl radicals with 1-4 carbon atoms, amino groups or phenyl radicals, and especially the group of the following structure J 2
in which R 31 and R 32 , identical or different, mean a hydrogen atom, an alkyl radical with 1-4 carbon atoms, phenyl; Y means radical -CO- or radical
n means 0 or 1, and if n means 1, then U means the radical -CO-.
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FR9715413 | 1997-12-05 | ||
FR9715413 | 1997-12-05 |
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RU2161479C2 RU2161479C2 (en) | 2001-01-10 |
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RU98122213/14A RU2161479C2 (en) | 1997-12-05 | 1998-12-04 | Method of direct coloring keratin fibers in two stages by direct main colors |
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US (1) | US6045591A (en) |
EP (1) | EP0920856B1 (en) |
JP (1) | JP3681295B2 (en) |
KR (1) | KR100305335B1 (en) |
CN (1) | CN1227097A (en) |
AT (1) | ATE258420T1 (en) |
AU (1) | AU711808B2 (en) |
BR (1) | BR9805515A (en) |
CA (1) | CA2253680A1 (en) |
DE (1) | DE69821324T2 (en) |
ES (1) | ES2215284T3 (en) |
HU (1) | HU222990B1 (en) |
MX (1) | MX214446B (en) |
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RU (1) | RU2161479C2 (en) |
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FR3136976A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136972A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136968A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3136975A1 (en) | 2022-06-22 | 2023-12-29 | L'oreal | Composition for lightening keratin fibers and process for lightening keratin fibers using this composition |
FR3144512A1 (en) | 2022-12-29 | 2024-07-05 | L'oreal | Composition comprising at least N,N-dicarboxymethyl glutamic acid, at least one coloring agent, and at least one fatty amine |
FR3144510A1 (en) | 2022-12-29 | 2024-07-05 | L'oreal | Composition comprising at least N,N-dicarboxymethyl glutamic acid, at least one direct dye, at least one cationic polysaccharide, and at least one non-cationic polysaccharide |
FR3144511A1 (en) | 2022-12-29 | 2024-07-05 | L'oreal | Composition comprising at least one direct dye, at least N,N-dicarboxymethyl glutamic acid, at least one cationic surfactant and at least one non-silicone fatty substance in a particular content |
FR3144513A1 (en) | 2022-12-29 | 2024-07-05 | L'oreal | Composition comprising at least N,N-dicarboxymethyl glutamic acid, at least one direct dye, and at least one associative polymer |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB880798A (en) * | 1959-08-20 | 1961-10-25 | Unilever Ltd | Compositions for dyeing human hair |
GB1113661A (en) * | 1965-01-25 | 1968-05-15 | Unilever Ltd | Process for dyeing hair |
US3497493A (en) * | 1966-10-04 | 1970-02-24 | Durand & Huguenin Ag | Water-soluble cationic metal complexes of formazan dyestuffs |
CH480839A (en) * | 1967-01-16 | 1969-11-15 | Sandoz Ag | Hair dyes |
FR1585308A (en) * | 1967-10-10 | 1970-01-16 | ||
LU61452A1 (en) * | 1970-07-31 | 1972-02-10 | ||
FR2106662A5 (en) * | 1970-09-18 | 1972-05-05 | Oreal | |
US3985499A (en) * | 1971-06-04 | 1976-10-12 | L'oreal | Diazamerocyanines for dyeing keratinous fibers |
LU65539A1 (en) * | 1972-06-19 | 1973-12-21 | ||
LU71015A1 (en) * | 1974-09-27 | 1976-08-19 | ||
US4182612A (en) * | 1977-01-31 | 1980-01-08 | The Gillette Company | Method for dyeing human hair with cationic polymeric dyes |
US4824768A (en) * | 1987-12-03 | 1989-04-25 | General Motors Corporation | Method for forming patterned alumina film element |
FR2676173B1 (en) * | 1991-05-06 | 1993-08-13 | Oreal | COSMETIC COMPOSITION CONTAINING AN ODORLESS ALKALINATING AGENT. |
FR2703589B1 (en) * | 1993-04-05 | 1995-05-19 | Oreal | Bleaching composition in granulated form usable for bleaching hair and process for the preparation of said composition. |
FR2703588B1 (en) * | 1993-04-05 | 1995-06-23 | Oreal | GRANULATED COMPOSITION BASED ON PEROXIDE DERIVATIVES USEFUL FOR THE DISCOLORATION OF HAIR AND PROCESS FOR PREPARING THE SAME. |
TW311089B (en) * | 1993-07-05 | 1997-07-21 | Ciba Sc Holding Ag | |
TW325998B (en) * | 1993-11-30 | 1998-02-01 | Ciba Sc Holding Ag | Dyeing keratin-containing fibers |
FR2715065B1 (en) * | 1994-01-14 | 1996-04-26 | Oreal | Cosmetic compositions for bleaching hair, method of synthesis and use. |
FR2716804B1 (en) * | 1994-03-02 | 1996-04-05 | Oreal | Cosmetic compositions for bleaching the hair, preparation process and use. |
JPH0859445A (en) * | 1994-05-04 | 1996-03-05 | L'oreal Sa | Method for improving effect of make-up treatment performed on bleached hair |
FR2719471B1 (en) * | 1994-05-04 | 1996-07-05 | Oreal | Method for bleaching hair by irradiation with a laser, and device. |
FR2719470B1 (en) * | 1994-05-04 | 1996-06-28 | Oreal | Method for bleaching hair by laser irradiation with cooling, and device for implementing it. |
ES2215944T3 (en) * | 1994-11-03 | 2004-10-16 | Ciba Specialty Chemicals Holding Inc. | CATIONIC IMIDAZOLAZOIC COLORS. |
US5688291A (en) * | 1996-06-27 | 1997-11-18 | L'avante Garde, Inc. | Composition for simultaneously lightening and coloring hair |
-
1998
- 1998-11-20 ES ES98402901T patent/ES2215284T3/en not_active Expired - Lifetime
- 1998-11-20 AT AT98402901T patent/ATE258420T1/en not_active IP Right Cessation
- 1998-11-20 EP EP98402901A patent/EP0920856B1/en not_active Expired - Lifetime
- 1998-11-20 DE DE1998621324 patent/DE69821324T2/en not_active Expired - Lifetime
- 1998-11-27 AU AU94209/98A patent/AU711808B2/en not_active Ceased
- 1998-12-01 MX MX9810109A patent/MX214446B/en not_active IP Right Cessation
- 1998-12-02 BR BR9805515-1A patent/BR9805515A/en not_active Application Discontinuation
- 1998-12-03 CA CA002253680A patent/CA2253680A1/en not_active Abandoned
- 1998-12-04 PL PL98330107A patent/PL330107A1/en unknown
- 1998-12-04 RU RU98122213/14A patent/RU2161479C2/en not_active IP Right Cessation
- 1998-12-04 CN CN98111649A patent/CN1227097A/en active Pending
- 1998-12-04 JP JP34618198A patent/JP3681295B2/en not_active Expired - Fee Related
- 1998-12-04 HU HU9802817A patent/HU222990B1/en not_active IP Right Cessation
- 1998-12-05 KR KR19980053241A patent/KR100305335B1/en not_active IP Right Cessation
- 1998-12-07 US US09/206,694 patent/US6045591A/en not_active Expired - Lifetime
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