MXPA99004755A - Composition of dyeing for keratinic fibers with a direct cationic coloring and a polymer sustant - Google Patents
Composition of dyeing for keratinic fibers with a direct cationic coloring and a polymer sustantInfo
- Publication number
- MXPA99004755A MXPA99004755A MXPA/A/1999/004755A MX9904755A MXPA99004755A MX PA99004755 A MXPA99004755 A MX PA99004755A MX 9904755 A MX9904755 A MX 9904755A MX PA99004755 A MXPA99004755 A MX PA99004755A
- Authority
- MX
- Mexico
- Prior art keywords
- composition
- dyeing
- radical
- composition according
- designates
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 238000004043 dyeing Methods 0.000 title claims abstract description 70
- 229920000642 polymer Polymers 0.000 title claims abstract description 40
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 35
- 239000000835 fiber Substances 0.000 title claims abstract description 34
- 238000004040 coloring Methods 0.000 title description 4
- 102000011782 Keratins Human genes 0.000 claims abstract description 27
- 108010076876 Keratins Proteins 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000975 dye Substances 0.000 claims description 38
- -1 alkyl radical Chemical class 0.000 claims description 33
- 230000003647 oxidation Effects 0.000 claims description 21
- 238000007254 oxidation reaction Methods 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 16
- 239000000982 direct dye Substances 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 12
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 10
- 229920001519 homopolymer Polymers 0.000 claims description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000002453 shampoo Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- BDHGFCVQWMDIQX-UHFFFAOYSA-O 3-ethenyl-2-methyl-1h-imidazol-3-ium Chemical group CC=1NC=C[N+]=1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-O 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- VZTGWJFIMGVKSN-UHFFFAOYSA-O trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium Chemical group CC(=C)C(=O)NCCC[N+](C)(C)C VZTGWJFIMGVKSN-UHFFFAOYSA-O 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229920000289 Polyquaternium Polymers 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- GGZKJFGVSZKFLD-UHFFFAOYSA-N 1-prop-1-enyl-1h-imidazol-1-ium;chloride Chemical compound [Cl-].CC=CN1C=C[NH+]=C1 GGZKJFGVSZKFLD-UHFFFAOYSA-N 0.000 description 2
- 206010001488 Aggression Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 2
- 230000016571 aggressive behavior Effects 0.000 description 2
- 230000003113 alkalizing effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229920002553 poly(2-methacrylolyloxyethyltrimethylammonium chloride) polymer Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- WAROVFJVCBYVHY-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C=CN1CCCC1=O.CC(=C)C(=O)NCCC[N+](C)(C)C WAROVFJVCBYVHY-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- HQLVRJJDJGNYQW-UHFFFAOYSA-O 3-prop-1-enyl-1H-imidazol-3-ium Chemical compound CC=C[NH+]1C=NC=C1 HQLVRJJDJGNYQW-UHFFFAOYSA-O 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108010029541 Laccase Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 108091007187 Reductases Proteins 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
- 239000002253 acid Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 230000006399 behavior Effects 0.000 description 1
- 239000003139 biocide 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
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000002304 perfume Substances 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
- 235000011118 potassium hydroxide Nutrition 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
- 238000007670 refining Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 238000012360 testing method Methods 0.000 description 1
- DGXNWWJYEMQHED-UHFFFAOYSA-N trimethyl-(4-methyl-3-oxopent-4-enyl)azanium Chemical compound CC(=C)C(=O)CC[N+](C)(C)C DGXNWWJYEMQHED-UHFFFAOYSA-N 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention relates to a dyeing composition for keratin fibers, in particular for human keratin fibers such as hair, comprising, in a medium suitable for dyeing, at least one direct cationic dye of the given formula, and which is characterized by the fact that it also contains at least one particular cationic or amphoteric substantive polymer. The invention also relates to the dyeing processes and devices used by the
Description
COMPOSITION OF DYEING FOR QUEKATINIC FIBERS WITH A CATIONIC DIRECT COLORING AND A SUBSTANTIVE POLYMER
The invention relates to a dyeing composition for keratin fibers, in particular for human keratin fibers such as hair, comprising, in a medium suitable for dyeing, at least one direct cationic dye of the given formula, and at least one polymer particular cationic or amphoteric noun. The invention also has as its object the dyeing methods and devices which use the said composition. In the capillary field, two types of coloration can be distinguished. The first is the semi-permanent or temporary coloration, or direct coloring, which uses dyes that are able to contribute to the natural coloration of the hair, a more or less pronounced color modification resistant eventually to several shampoos. These dyes are called direct dyes; they can be carried out with or without oxidizing agents. In the presence of an oxidant, the purpose is to obtain a clarified coloration. The rinsed coloration is carried out by applying the extemporaneous mixture of a direct dye and an oxidant on the hair, and it is possible in particular to obtain by refining REF .: 30188 of the melanin of the hair, an advantageous effect such as a uniform color in the case of hair. gray hair or highlight the color in the case of naturally pigmented hair. The second is the permanent coloration or oxidation coloration. This is carried out with dyes called "oxidation" which comprise oxidation dye precursors and copulators. Oxidation staining precursors, commonly called "oxidation base", are initially colorless or weakly colored compounds that develop their dyeing power in the hair in the presence of oxidizing agents added at the time of use, leading to the formation of colored compounds and colorants. The formation of these colored compounds and dyes, either by an oxidative condensation of the "oxidation bases" on themselves, or by an oxidative condensation of the "oxidation bases" on coloring modifying compounds commonly called "couplers" and generally present in the dyeing compositions used in oxidation dyeing. To vary the shades obtained with the indicated oxidation dyes, or enrich them with reflections, it happens that they are added direct dyes.
Among the cationic direct dyes available in the field of dyeing of particularly human keratin fibers, the compounds whose structure will be developed in the text that follows are already known; However, these dyes lead to colorations that have still insufficient characteristics, while at the same time in the plane of homogeneity of the color distributed along the fiber ("unisson") (uniformity), it is said then that the coloration is too selective, and in the plañe of the tenacity, in terms of resistance to the various aggressions that can experience the hair (light, bad weather, lavas with shampoo). However, after important investigations carried out on the subject, the applicant firm has now discovered that it is possible new compositions for the dyeing of keratin fibers capable of leading to less selective colorations and that better resist the various aggressions that can experiencing the hair, associated with at least one particular cationic or amphoteric substantive polymer with at least one known cationic direct dye of the prior art and of the formula (I) defined below. This discovery forms the basis of the present invention.
The present invention therefore has as its first objective a composition for dyeing keratin fibers and in particular human keratin fibers such as hair, which includes in a medium suitable for dyeing, (i) at least one direct cationic dye whose structure corresponds to the following formula (I), characterized in that it also contains (ii) at least one cationic or amphoteric substantive polymer particular. (i) The cationic direct dye usable according to the present invention is a compound of formula (I) below: A - N = N - B (I) in which: the symbol A represents a group selected from the structures Al to A3 following :
structures A1 to A3 in which Ri denotes an alkyl radical of C? -C4 / a phenyl radical which can be substituted by an alkyl radical of C? -C4 or a halogen atom selected from chlorine, bromine, iodine and fluorine; R 2 denotes a C 1 -C 4 alkyl radical or a phenyl radical; R3 and R4, which are identical or different, represent a C1-C4 alkyl radical, a phenyl radical, or, in the case of the Al structure, can together form a substituted benzene ring, and in the case of the A2 structure, can together form a benzene ring optionally substituted by one or more C1-C4 alkyl radicals, C1-C4 alkoxy, or N02; R3 can also designate a hydrogen atom, -Z designates an oxygen atom, sulfur or a group -NR2; M represents a group -CH, -CR (designating R C 1 -C 4 alkyl), or -NR 5 (β -) r; K represents a group -CH, -CR (designated R C 1 -C 4 alkyl) or -NR 5 (X ") r P represents a group -CH, -CR (designating R C 1 -C 4 alkyl), or -NR 5 (X ") r; r designates zero or 1; R5 represents a 0"atom, a C1-C4 olkoxy radical, or an alkyne radical of C? -C4; R6 and R7, identical or different, represent a hydrogen or halogen atom, selected from chlorine, bromine, iodine and fluorine, a C 1 -C 4 alkyl radical, C 1 -C 4 alkoxy / a radical -N 0 2, X "represents an anion preferably selected from chloride, iodide, methyl sulfate, ethyl sulfate, acetate and perchlorate; with the proviso that, if R 4 designates a C 1 -C 4 alkyl radical and Z designates a sulfur atom, R 3 does not designate a hydrogen atom; if R5 designates O ", then r designates zero, if K or P or M designates -N-C1-C4 alkyl X", then R6 or R7 is different from a hydrogen atom; if K designates -NR5 (X ~) r, then M = P = -CH; -CR; if M designates -NR5 (X ") r, then K = P = -CH; -CR; if P designates -NR5 (X") r, then K = M and designate -CH or -CR; if Z denotes -NR2 and R2 designates an alkyl radical of C? -C4, then at least one of the radicals Ri, R3 or R4 of A2 is different from a C1-C4 alkyl radical; symbol B represents: - (a) a group of structure Bl following:
structure Bl in which R8 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine, and fluorine, an alkyl radical of C? -C4 / C1-C4 alkoxy, an OH radical , -N02, -NHRn, -NR? 2R? 3 / -NHCOalkyl of C1-C4, or form with R9 a cycle of 5 or 6 links containing or not one or more heteroatoms selected from nitrogen, oxygen or sulfur; R9 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, a C1-C4 alkyl radical, C?-C alco alkoxy or a R 10 or Rn form; or 6 links containing or not one or more heteroatoms selected from nitrogen, oxygen or sulfur; Rio represents a hydrogen atom, a radical -OH, a radical -NHRn, a radical -NR12R13; R n represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, C 2 -C 4 polyhydroxyalkyl, a phenyl radical; R12 and Ri3 identical or different, represent a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, C 2 -C 4 polyhydroxyalkyl radical; - (b) a 5- or 6-membered heterocyclic nitrogenous group capable of including other heteroatoms and / or carbonylated groups and which can be substituted by one or more C 1 -C 4 alkyl, amino or phenyl radicals, and particularly a group of structure B2 following: structure B2 in which identical or different Ri4 and R15 represent a hydrogen atom, an alkyl radical of C? -C / a phenyl radical; CH3 I Y designates the radical -CO- or the radical -C =; n = 0 or 1, with, when n designates 1, U designates the radical -CO. In the structures defined above, the C 1 -C 4 alkyl or alkoxy group preferably designates methyl, ethyl, butyl, methoxy, ethoxy. The cationic direct dyes of formula (I) which can be used in the dyeing compositions according to the invention are known compounds and are described, for example, in patent applications FR-2189006, FR-2285851 and FR-2140205 and their certificates of addition. Among the direct cationic dyes of formula
(I) which can be used in the dyeing compositions according to the invention, those of the formula (I) in which the symbol A designates the structure A3 while the symbol B designates the structure Bl or B2 are particularly preferred. Among these compounds, mention may be made more particularly of the compounds of structures (Di a (I) 77
following:
l_ O
CH3S04"
CH3S04"CH3S04"
CH3S04"
CH, SO
fifteen
CH3S04"
twenty
CH3S04"CH3S04"
twenty
20
C4H9
fifteen
twenty
15 20
20
CH3SO4 10
(I) 72 i Ó "
twenty
The cationic direct dye (s) used according to the invention preferably represent from 0.001 to 10% by weight approximately of the total weight of the dyeing composition and even more preferably from 0.005 to 5% by weight approximately of this weight. (ii) The cationic or amphoteric substantive polymer usable according to the present invention is chosen from the group consisting of: 1 / - the omopolymers - and the dimethyldiallylammonium halide copolymers; 2 / - methacryloyloxyethyltrimethylammonium halide homopolymers and copolymers; 3 / - the polyammonium quaternary polymers selected from those described below; 4 / - the copolymers of vinylpyrrolidone with methacrylamidopropyltrimethylammonium units or with methyl vinylimidazolium units; 5 / - its mixtures. The substantive character (ie the behavior in the deposit on the hair) of the polymers used according to the invention is classically determined by means of the test described by Richard J. Crawford, Journal of the Society of Cosmetic Chemists, 1980, 31- (5 ) - page 273 to 278 (developed by Red 80 acid dye). Among the substantive polymers of the homopolymer type and methacryloyloxyethyltrimethylammonium halide copolymer usable according to the invention, mention may be made in particular of the products which are referred to in the CTFA dictionary (5 * edition, 1993) "Polyquaternium 37", "Polyquaternium 32" and " Polyquaternium 35", corresponding, respectively, with respect to" Polyquaternium 37", to the crosslinked homopolymer of methacryloyloxyethyltrimethylammonium chloride, in 50% dispersion in mineral oil, and sold under the name Saleare SC95 by the Allied Colloids Company, Regarding the
"Polyquaternium 32", to the crosslinked copolymer of acrylamide and methacryloyloxyethyltrimethylammonium chloride
(20/80 by weight), in 50% dispersion in mineral oil, and sold under the name Saleare SC92 by the Allied Colloids Company, and with respect to "Polyquaternium 35", methacrylate of methacryloylethyltrimethylammonium and methacryloyloxyethyldimethylacetylammonium copolymer , sold under the name Plex 7525L by the company Rohm GmbH.
Among the substantive polymers of the dimethyldiallylammonium halide polymer type which can be used according to the invention, mention may be made, in particular, of the homopolymers of dimethyldiallylammonium chloride such as that sold under the name "Marquat 100", by the Merck Company; the copolymers of diallyldimethylammonium chloride and of acrylic acid as the proportions (80/20 by weight) sold under the name Merquat 280 by the Calgon Company; the copolymers of dimethyldiallylammonium chloride and of acrylamide sold under the names Merquat 550 and Merquat S by the Merck Company. Among the substantive polymers of the quaternary polyammonium type which can be used according to the invention, mention may be made of:
The polymers prepared and described in French patent 2,270,846, consisting of recurring units corresponding to the following formula (II):
CH, CH, CH CH, and particularly those whose molecular but, determined by gel permeation chromatography, is between 9500 and 9900; the polymers prepared and described by the French patent 2,270,846, constituted by recurring units corresponding to the following formula (III):
f- II) CH C2H5
and particularly those whose molecular weight, determined by gel permeation chromatography, is about 1200; the polymers described and prepared in the patents US 4,157,388, 4,390,689, 4,702,906, 4,719,282, and constituted by recurring units corresponding to the formula (IV), following:
CH, CH, c? - Cl- 1+ (IV)
-N + CH 2 > NH-CO-D-NH- (CH2i-N- (CH2) -O- (CH2 2) > 2 CH, CH, wherein p designates an integer ranging from 1 to about 6, D may be null or can represent a group - (CH2) r-CO- in which r designates a number equal to 4 or 7, the molecular mass of said polymers preferably being less than 100 000, and more preferably still less than or equal to 50 000, such polymers are sold in particular by the company Miranol under the names "Mirapol A15", "Mirapol AD1", "Mirapol AZI" and "Mirapol 175; Among the polymers of vinylpyrrolidone (PVP) with methacrylamidopropyltrimethylammonium units (MAPTAC), Mention may be made particularly of those sold under the trade names GAFQUAT ACP 1011 and GAFQUAT HS 100 by the company ISP. Among the polymers of vinylpyrrolidone (PVP) with methyl vinylimidazolium units, there may be mentioned more particularly: PVP / Methylvinylimidazolium chloride, sold under the names LUVIQUAT FC 3 70, FC 550, FC 905, HM 552 by the B.A.S.F. ^ -the PVP / methylvinylimidazolium chloride / vinylimidazole, sold under the name LUVIQUAT 8155 by the company B.A.S.F. -the PVP / Methylvinylimidazolium methosulfate, sold under the name LUVIQUAT MS 370 by the company B.A.S.F.
The concentration of substantive polymers (ii) in the dyeing composition according to the invention may vary between 0.01, and approximately 10% relative to the total weight of the dyeing composition, and preferably between 0.1 and 5%. The suitable medium for the dye (or support) is generally constituted by water or by a mixture of water and by at least one organic solvent to solubilize the compounds that were not sufficiently soluble in water. As the organic solvent, Cx-C4 lower alkanols, such as ethanol and isopropanol, can be mentioned, for example; the aromatic alcohols, such as benzyl alcohol, as well as analogous products and their mixtures. The solvents may be present in proportions preferably comprised between 1 and 40% by weight approximately relative to the total weight of the dyeing composition, and even more preferably approximately 5 and 30% by weight. The pH of the composition according to the invention is generally between approximately 2 and 11, and preferably between approximately 5 and 10. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used in the dyeing of keratin fibers. Among the acidulating agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, acid lactic, sulfonic acids. Examples of alkalizing agents which may be mentioned include ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of the formula (V) following:
in which is a propylene residue optionally substituted by a hydroxyl group or an alkyl radical of C? -C3; Ri6, R17, R-18 and Ri9 / identical or different, represent a hydrogen atom, an alkyl radical of C6-C6 or hydroxyalkyl of Cx-Ce. The dyeing composition according to the invention can contain, in addition to the cationic direct dye (s) defined above, containing one or more additional direct dyes which can be chosen, for example, from nitrobenzene dyes, anthraquinone dyes, naphthoquinone dyes, triarylmetanic dyes, xanthic dyes, non-cationic azo dyes. When it is intended for oxidation dyeing, the dyeing composition according to the invention contains, in addition to the cationic direct dye (i) one or more oxidation bases selected from the oxidation bases conventionally used for oxidation dyeing and between the oxidation dyes. which may be particularly cited paraphenylenediamines, bis-phenylalkydiamines, para-aminophenols, ortho-aminophenols and heterocyclic bases. When used, the oxidation base or bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dyeing composition, and even more preferably from 0.005 to 6% by weight approximately of this weight . When it is intended for oxidation dyeing, the dyeing composition according to the invention can also include, in addition to the direct cationic dye (i) and the substantive polymer (ii) as well as the oxidation bases, one or more couplers for the purpose to modify or enrich with reflections the shades obtained using the direct cationic dye (s) and the oxidation base (s). The copulators which can be used in the dyeing composition according to the invention can be chosen from the couplers conventionally used in oxidation dyeing, among which metaphenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers can be particularly mentioned. When present, the coupler (s) preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dyeing composition and even more preferably from 0.005 to 5% by weight approximately of this weight. The dyeing composition according to the invention can also include various adjuvants conventionally used in dyeing compositions for hair, such as antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, surface active agents, smoke-killing agents, ceramides. , preservatives, filtering agents, opacifying agents. Of course, the person skilled in the art will try to choose this or these possible complementary compounds in such a way that the advantageous properties intrinsically related to the dyeing composition according to the invention are not substantially alternating with the addition (s) considered. The dye composition according to the invention can be in various forms, such as in the form of liquids, shampoos, creams, gels, or in any other form suitable for dyeing the keratin fibers, and particularly the human hair. It can be obtained by extemporaneous mixing of a composition, possibly pulverulent, containing the cationic dye (s) with a composition containing the particular substantive polymer (s). When the combination of cationic direct dyes (i) and polymer substantives (ii) according to the invention is used in a composition intended for oxidation dyeing (one or more oxidation bases are then used, optionally in the presence of one or more couplers) ) or when used in a composition intended for direct lightening dye, then the dyeing composition according to the invention further includes at least one oxidizing agent, selected for example between hydrogen peroxide, urea peroxide, alkali metal bromates , persalts such as perborates and persulfates, and enzymes such as peroxidases, laccases and two-electron oxide reductases. The use of hydrogen peroxide or enzymes is particularly preferred. Another object of the invention is a process for dyeing keratin fibers and in particular human keratin fibers such as hair using the dyeing composition as defined above. According to a first variant of this dyeing process according to the invention, at least one dyeing composition as defined above is applied to the fibers for a sufficient time to develop the desired coloration, after which it is rinsed, washed with shampoo, rinsed again and dried. The time necessary for the development of the coloration on the keratin fibers is generally between 3 and 60 minutes and even more precisely between 5 and 40 minutes. According to a second variant of this direct dyeing process according to the invention, at least one dyeing composition as defined above is applied to the fibers for a sufficient time to develop the desired dyeing, without final rinsing. According to a particular embodiment of this dyeing process, and when the dyeing composition according to the invention includes at least one oxidation base and at least one oxidizing agent, the dyeing process includes a preliminary step consisting of storing separately , on the one hand, a composition (Al) comprising, in a medium suitable for dyeing, at least one direct cationic dye (i) as defined above and at least one oxidation base and, on the other hand
• part, a composition (Bl) that includes, in a suitable medium for the dye, at least one oxidizing agent, then in proceeding to its mixing at moments of use before applying this mixture on the keratin fibers, containing the composition ( Al) or composition (Bl) the cationic or amphoteric substantive polymer (ii) as defined above. According to another particular embodiment of this dyeing process, and when the dyeing composition according to the invention includes at least one oxidizing agent, the dyeing process includes a preliminary step consisting of storing separately, on the one hand, a composition (A2) comprising, in a medium suitable for dyeing, at least one direct cationic dye (i) as defined above and, on the other hand, a composition
(B2) which includes, in a suitable medium for the dye, at least one oxidizing agent, then in mixing it at the time of use before applying this mixture on the keratin fibers, containing the composition (A2) or the composition (B2) the cationic or amphoteric substantive polymer as defined above. Another object of the invention in a multi-compartment device or "kit" of dyes or any other conditioning system of several compartments of which a first compartment includes the composition (Al) or (A2) as defined above and a second compartment includes composition (Bl) or (B2) as defined above. These devices can be equipped with a means for providing the desired mixture on the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant firm. The following examples are intended to illustrate the invention without thereby limiting the scope. EXAMPLES EXAMPLE 1 The following dye composition was prepared: Cationic direct dye of formula Iao) 0.12 g
Nonyl phenol in 9 moles of ethylene oxides 8.0 g
Substantial polymer of the quaternary polyammonium type of formula (II) 1.0 gM.A. *
Ethanol 10.0 g 2-amino-2-methyl-1-propanol c.s pH 9 Demineralized water c.s.p 100 g
M: A. *: Active Matter The composition indicated above was applied for 30 minutes on natural gray hair strands at 90% white. The hair strands were then rinsed, washed with a conventional shampoo and then dried. They were stained in an intense red tone. A similar result was obtained with the dye
(1) 1. EXAMPLE 2: The following dye composition was prepared. Direct cationic dye of formula I < 27) 0.10 g Polymer substantive: diallyldimethylammonium chloride homopolymer sold under the name Merquat 100 by the company CALGON 1.0 gM.A. *
Ethanol 10.0 g Nonyl phenol in 9 moles of ethylene oxides 8.0 g
2-amino-2-methytic-propanol c.s pH 9
Demineralized water .'... c.s.p 100 g
M.A. *: Active Matter The composition indicated above was applied for 30 minutes on natural gray hair strands with 90% white. The hair strands were then rinsed, washed with a conventional shampoo and then dried. They were stained in an intense purple hue.
A similar result was obtained with the dye
(1) 32.
It is noted that in relation to this date, the best method known by the applicant to implement the said invention, from the manufacture of the objects to which they refer. Having described the invention as above, the content of the following is claimed as property.
Claims (24)
- CLAIMS 1. Composition for dyeing keratin fibers and in particular human keratin fibers such as hair, including in a medium suitable for dyeing, (i) at least one direct cationic dye of formula (I) below: A - N = N - B (I) in which: symbol A represents a group selected from the following Al a A3 structures: structures A1 to A3 in which Ri denotes an alkyl radical of C? -C4, a phenyl radical which can be substituted by an alkyl radical of C? -C4 or a halogen atom selected from chlorine, bromine, iodine and fluorine; R 2 denotes a C 1 -C 4 alkyl radical or a phenyl radical; R3 and R4, identical or different, represent an alkyl radical of C? -C4 / a phenyl radical, or, in the case of the structure Al, can together form a substituted benzene ring, and in the case of structure A2, can together form a benzene ring optionally substituted by one or more C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or N 0 2 radicals; R3 may also designate a hydrogen atom; Z denotes an oxygen atom, sulfur or a group -NR2; M represents a group -CH, -CR (designated R C 1 -C 4 alkyl), or -NR 5, (X ~) r; K represents a group -CH, -CR (designated R C 1 -C 4 alkyl), or -NR 5 (X ") r; P represents a group -CH, -CR (designated R C 1 -C 4 alkyl), or - NR5 (X ") r; r designates zero or 1; R5 represents an O "atom, a C1-C4 alkoxy radical, or an alkyl radical of C? -C4; R6 and R7, identical or different, represents a hydrogen or halogen atom, selected from chlorine, bromine, iodine and fluorine, a C1-C4 alkyl radical, C1-C4 alkoxy, a radical -N02; X "represents an anion of preference by selecting from chloride, iodide, methyl sulfate, ethyl sulfate, acetate and perchlorate; with the proviso that, if R denotes C 1 -C 4 alkyl radical and Z designates a sulfur atom, R 3 does not designate a hydrogen atom; if R5 designates O ", then r designates zero, if K or P or M designates -N-C1-C4 alkyl X", then R6 or R7 is different from a hydrogen atom; if K designates -NR5 (X ") r, then M = P = -CH; -CR; if M designates -NR5 (X") r, then K = P = -CH; -CR; if P designates -NR5 (X ~) r, then K = M and designate -CH or -CR; if Z designates -NR2 and R2 denotes a C1-C4 alkyl radical, then at least one of the radicals R1 t R3 or R4 of A2 is different from a C 1 -C 4 alkyl radical; symbol B represents: - (a) a group of structure Bl following: structure Bl in which R8 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, an alkyl radical of C?-C4, alkoxy of C?-C4, an OH radical , -N02, -NHRn, -NR? 2R? 3, -NHCOalkyl of C? -C4, forms with R9 a cycle of 5 or 6 links containing or not one or more heteroatoms selected from nitrogen, oxygen or sulfur; R9 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, an alkyl radical of C? -C4, alkoxy of C? -C4, or forms with Ri0 or Rn a cycle of 5 or 6 links containing or not one or more heteroatoms selected from nitrogen, oxygen or sulfur; Rio represents a hydrogen atom, a radical -OH, a radical -NHRn, a radical -NR12R13; R n represents a hydrogen atom, an alkyl radical of C? -C, a monohydroxyalkyl radical of C 1 -C 4, polyhydroxyalkyl of C 2 -C 4, a phenyl radical; R 12 and R 3, identical or different, represent a C 1 -C 4 alkyl radical / a C 1 -C 4 monohydroxyalkyl radical, C 2 -C 4 polyhydroxyalkyl radical; - (b) a 5- or 6-membered nitrogenous heterocyclic group capable of including other heteroatoms and / or carbonylated groups and which can be substituted by one or more C?-C / amino or phenyl alkyl radicals, and particularly a structure group B2 following: structure B2 in which, R12 and Ri5 / identical or different, represent a hydrogen atom, a C1-C4 alkyl radical, a phenyl radical CH3 Y designates the radical -CO- or the radical -C =; n = 0 or 1, with, when n designates 1, U designates the radical -CO- characterizing the said composition by the fact that it also contains: (ii) at least one cationic or amphoteric substantive polymer selected from the group consisting of: 1 / - the homopolymers and copolymers of dimethyldiallylammonium halide; 2 / - methacryloyloxyethyltrimethylammonium halide homopolymers and copolymers; 3 / - the polyammonium quaternary polymers selected from the group consisting of: polymers consisting of recurring units corresponding to formula (II) below: CH, CH, CH CH, - the polymers formed by recurring units corresponding to formula (III) below: CH, C2H5 N ^ (CH2) 3 -N + -fCH2) 3 (III) Br Br] CH C2H5 - the polymers formed by recurring units corresponding to the following formula (IV): CH, CH, in which p designates an integer ranging from 1 to approximately 6, D may be null or may represent n group - (CH2) r-CO- in which r denotes a number equal to 4 or 7; 4 / - the copolymers of vinylpyrrolidone with methacrylamidopropyltrimethylammonium units or with methyl vinylimidazolium units; 5 / - its mixtures.
- 2. Composition according to claim 1, characterized in that in the formula (I), the C? -C alkyl radicals and the C? -C4 alkoxy radicals are methyl, ethyl, butyl, methoxy and ethoxy radicals.
- 3. Composition according to claim 2, characterized in that the direct cationic dyes respond to the structures (I)? a (I) 77 following: 25 fifteen twenty 25 15 O " 25 CH3S04"CH3S04" CH3S04" CH3S04" fifteen CH3S04" twenty CH, S0. " 25 CH3S04" CH3S04" twenty CH3S04" 25 20 25 C4H9 twenty 25 15 twenty 10 20 25 10 fifteen -N 25 H, C * OH. 25 20 25 CH3SO4 10 20 25
- 4. Composition according to any one of the preceding claims, characterized in that the cationic direct dye (s) of formula (I) represent from 0.001 to 10% by weight of the total weight of the composition.
- Composition according to claim 4, characterized in that the cationic direct dye (s) of formula (I) represent from 0.005 to 5% by weight of the total weight of the composition.
- Composition according to any one of Claims 1 to 5, characterized in that the substantive polymer is a homopolymer of dimethyldiallylammonium chloride.
- Composition according to any one of Claims 1 to 5, characterized in that the substantive polymer of the dimethyldiallylammonium halide copolymer type is a copolymer of dimethyldiallylammonium chloride and acrylic acid (80/20 by weight).
- Composition according to any one of Claims 1 to 5, characterized in that the substantive polymers of the homopolymer and methacryloyloxyethyltrimethylammonium halide copolymer type are selected from the crosslinked homopolymer of methacryloyloxyethyltrimethylammonium chloride, in 50% dispersion in mineral oil , the crosslinked copolymer of acrylamide and methacryloyloxyethyltrimethylammonium chloride (20/80 by weight), in 50% dispersion in mineral oil, the methacryloylate of the methacryloyloxyethyltrimethylammonium and methacryloyloxyethyldimethylacetylammonium copolymer.
- Composition according to any one of the preceding claims, characterized in that the substantive polymer (s) represent from 0.01 to 10% by weight of the total weight of the composition.
- Composition according to claim 9, characterized in that the substantive polymer (s) represent 0.1 to 5% by weight of the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that the appropriate medium for the dye (or support) is constituted by water or by a mixture of water and at least one organic solvent.
- Composition according to any one of the preceding claims, characterized in that it has a pH comprised between 2 and 11, and preferably between 5 and 10.
- Composition according to any one of the preceding claims, characterized by fact that it is intended for oxidation dyeing and because it contains one or more oxidation bases selected from para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
- Composition according to claim 13, characterized in that the oxidation base (s) represent from 0.0005 to 12% by weight of the total weight of the dyeing composition.
- 15. Composition according to claim 14, characterized in that the oxidation base (s) represent from 0.005 to 6% by weight of the total weight of the dyeing composition.
- Composition according to any one of claims 13 to 15, characterized in that it includes one or more couplers selected from meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers.
- 17. Composition according to claim 16, characterized in that the copulator (s) represent from 0.0001 to 10% by weight of the total weight of the dyeing composition.
- 18. Composition according to claim 17, characterized in that the coupler (s) represent from 0.005 to 5% by total weight of the dyeing composition.
- Composition according to any one of the preceding claims, characterized in that it is intended for oxidation dyeing or direct lightening dyeing and because it includes at least one oxidizing agent.
- Procedure for dyeing keratin fibers and in particular human keratin fibers such as hair, characterized in that at least one dyeing composition as defined in any one of claims 1 to 19 is applied to the fibers. , for a sufficient time to develop the desired coloration, after which it is clarified, it is eventually washed with shampoo, rinsed again and dried.
- 21. Process for dyeing keratin fibers and in particular human keratin fibers such as hair, characterized in that at least one dyeing composition is applied to the fibers as defined in any one of claims 1 to 19, for a sufficient time to develop the desired coloration, without final rinse.
- Procedure for dyeing keratin fibers and in particular human keratin fibers, such as hair, characterized in that it comprises a preliminary step consisting in storing separately a composition on the one hand (Al) comprising, in a medium suitable for dyeing, at least one direct cationic dye of formula (I) as defined in claims 1 to 5 and at least one oxidation base and, another part, a composition (Bl) which includes, in a suitable medium for the dye, at least one oxidizing agent, then in proceeding to its mixing at the time of use before applying this mixture on the keratin fibers, containing the composition (Al) or the composition (Bl) the substantive polymer as defined in claims 6 to 10.
- 23. Process for dyeing the keratin fibers and in particular the human keratin fibers such as the hair, characterized in that it comprises a step preliminary, consisting of storing separately a composition on the one hand (A2) comprising, in a medium suitable for dyeing, at least one direct cationic dye of formula (I) as defined in claims 1 to 5 and, on the other hand, a composition (B2) including, in a suitable medium for the dye, at least one oxidizing agent, then in proceeding to its mixing at the time of use before applying this mixture on the keratin fibers, containing the composition (A2) or the composition (B2) the polymer noun as defined in claims 6 to 10.
- 24. Multi-compartment dyeing device or "kit" of several compartments, characterized in that a first compartment includes the composition (Al) or (A2) as defined in claim 22 or 23 and a second compartment includes the composition (Bl) or (B2) as defined in claim 22 or 23.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9806549 | 1998-05-25 | ||
| FR9806549A FR2778845B1 (en) | 1998-05-25 | 1998-05-25 | DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND SUBSTANTIVE POLYMER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MXPA99004755A true MXPA99004755A (en) | 2000-08-01 |
| MX216728B MX216728B (en) | 2003-10-03 |
Family
ID=9526670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9904755A MX216728B (en) | 1998-05-25 | 1999-05-21 | Dye composition for keratin fibres, with a cationic direct dye and a substantive polymer |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6592633B2 (en) |
| EP (1) | EP0960617B1 (en) |
| JP (1) | JP2000007542A (en) |
| KR (1) | KR100330384B1 (en) |
| CN (1) | CN1236608A (en) |
| AR (1) | AR019309A1 (en) |
| AT (1) | ATE278377T1 (en) |
| AU (1) | AU726541B2 (en) |
| BR (1) | BR9902311A (en) |
| CA (1) | CA2272831A1 (en) |
| DE (1) | DE69920798T2 (en) |
| ES (1) | ES2230813T3 (en) |
| FR (1) | FR2778845B1 (en) |
| HU (1) | HUP9901703A3 (en) |
| MX (1) | MX216728B (en) |
| PL (1) | PL333321A1 (en) |
| RU (1) | RU2166311C2 (en) |
| ZA (1) | ZA992935B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2778845B1 (en) * | 1998-05-25 | 2001-05-04 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND SUBSTANTIVE POLYMER |
| FR2803198B1 (en) * | 1999-12-30 | 2003-09-26 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING TWO PARTICULAR QUATERNARY POLYAMMONIUMS |
| FR2803195B1 (en) | 1999-12-30 | 2002-03-15 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING A THICKENING POLYMER COMPRISING AT LEAST ONE FATTY CHAIN AND A SINGLE- OR POLY-GLYCEROLE FATTY ALCOHOL |
| DE10007776A1 (en) * | 2000-02-21 | 2001-09-06 | Goldwell Gmbh | Hair dye |
| FR2807650B1 (en) * | 2000-04-18 | 2002-05-24 | Oreal | KERATIN FIBER OXIDATION DYE COMPOSITION COMPRISING 1- (4-AMINOPHENYL) -PYRROLIDINE AND A PARTICULAR DIRECT DYE |
| US7101406B2 (en) | 2002-12-13 | 2006-09-05 | L'oreal | Dyeing composition comprising a cationic tertiary para-phenylenediamine and a heterocyclic cationic direct dye, methods and uses |
| FR2848439A1 (en) * | 2002-12-13 | 2004-06-18 | Oreal | TINCTORIAL COMPOSITION COMPRISING CATIONIC TERAPHARY PARAPHENYLENEDIAMINE AND CATIONIC HETEROCYCLIC DIRECT COLOR, METHODS AND USES |
| ATE428399T1 (en) * | 2003-07-26 | 2009-05-15 | Kpss Kao Gmbh | CONDITIONING HAIR DYE COMPOSITION |
| JP2005248256A (en) * | 2004-03-04 | 2005-09-15 | Shimano Inc | SURFACE HARDENING TREATMENT METHOD FOR beta TYPE TITANIUM, beta TYPE TITANIUM BASED MEMBER AND SURFACE HARDENING TREATMENT DEVICE FOR beta TYPE TITANIUM |
| US7497878B2 (en) * | 2005-06-30 | 2009-03-03 | L'oreal, S.A. | Azo dyes containing a sulphonamide or amide function for the dyeing of human keratin fibers and method of dyeing and dyeing compositions containing them |
| FR2887769B1 (en) * | 2005-06-30 | 2010-12-17 | Oreal | USE OF AZO COLORANTS COMPRISING A SULFONAMIDE OR AMIDE FUNCTION FOR THE COLORING OF HUMAN KERATIN FIBERS AND A COLORING PROCESS AND A TINCTORIAL COMPOSITION COMPRISING THE SAME |
| GB0617024D0 (en) * | 2006-08-30 | 2006-10-11 | Unilever Plc | Hair treatment compositions incorporating hair substantive polymers |
| CN102159698B (en) * | 2008-09-23 | 2013-04-24 | 荷兰联合利华有限公司 | Cationic pyridine and pyridazine dyes |
| US9884004B2 (en) | 2013-06-28 | 2018-02-06 | L'oreal | Compositions and methods for treating hair |
| US9789051B2 (en) | 2013-06-28 | 2017-10-17 | L'oreal | Compositions and methods for treating hair |
| US9884003B2 (en) | 2013-06-28 | 2018-02-06 | L'oreal | Compositions and methods for treating hair |
| US9795555B2 (en) | 2013-06-28 | 2017-10-24 | L'oreal | Compositions and methods for treating hair |
| US9839600B2 (en) | 2013-06-28 | 2017-12-12 | L'oreal | Compositions and methods for treating hair |
| US9884002B2 (en) | 2013-06-28 | 2018-02-06 | L'oreal | Compositions and methods for treating hair |
| US9795556B2 (en) | 2013-06-28 | 2017-10-24 | L'oreal | Compositions and methods for treating hair |
| US9789050B2 (en) | 2013-06-28 | 2017-10-17 | L'oreal | Compositions and methods for treating hair |
| US9801804B2 (en) | 2013-06-28 | 2017-10-31 | L'oreal | Compositions and methods for treating hair |
| US9788627B2 (en) | 2013-06-28 | 2017-10-17 | L'oreal | Compositions and methods for treating hair |
| US9801808B2 (en) | 2014-12-19 | 2017-10-31 | Loreal | Hair styling compositions comprising latex polymers and wax dispersions |
| US10195122B2 (en) | 2014-12-19 | 2019-02-05 | L'oreal | Compositions and methods for hair |
| US9750678B2 (en) | 2014-12-19 | 2017-09-05 | L'oreal | Hair coloring compositions comprising latex polymers |
| US9814668B2 (en) | 2014-12-19 | 2017-11-14 | L'oreal | Hair styling compositions comprising latex polymers |
| US9814669B2 (en) | 2014-12-19 | 2017-11-14 | L'oreal | Hair cosmetic composition containing latex polymers and a silicone-organic polymer compound |
| US10813853B2 (en) | 2014-12-30 | 2020-10-27 | L'oreal | Compositions and methods for hair |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH560539A5 (en) * | 1971-06-04 | 1975-04-15 | Oreal | |
| US3985499A (en) * | 1971-06-04 | 1976-10-12 | L'oreal | Diazamerocyanines for dyeing keratinous fibers |
| LU65539A1 (en) * | 1972-06-19 | 1973-12-21 | ||
| US3986825A (en) * | 1972-06-29 | 1976-10-19 | The Gillette Company | Hair coloring composition containing water-soluble amino and quaternary ammonium polymers |
| BE829081A (en) | 1974-05-16 | 1975-11-14 | NEW COSMETIC AGENTS BASED ON QUATERNIZED POLYMERS | |
| LU71015A1 (en) | 1974-09-27 | 1976-08-19 | ||
| US4157388A (en) | 1977-06-23 | 1979-06-05 | The Miranol Chemical Company, Inc. | Hair and fabric conditioning compositions containing polymeric ionenes |
| FR2471777A1 (en) | 1979-12-21 | 1981-06-26 | Oreal | NOVEL COSMETIC AGENTS BASED ON POLYCATIONIC POLYMERS, AND THEIR USE IN COSMETIC COMPOSITIONS |
| FR2471997B1 (en) | 1979-12-21 | 1987-08-28 | Oreal | NOVEL POLYCATION POLYMERS, THEIR PREPARATION AND THEIR USE |
| DE3524263A1 (en) * | 1985-07-06 | 1987-01-08 | Wella Ag | AGENT FOR CARE OF THE HAIR |
| FR2586913B1 (en) | 1985-09-10 | 1990-08-03 | Oreal | PROCESS FOR FORMING IN SITU A COMPOSITION CONSISTING OF TWO SEPARATELY PACKED PARTS AND DISPENSING ASSEMBLY FOR THE IMPLEMENTATION OF THIS PROCESS |
| US4719282A (en) | 1986-04-22 | 1988-01-12 | Miranol Inc. | Polycationic block copolymer |
| US4772462A (en) * | 1986-10-27 | 1988-09-20 | Calgon Corporation | Hair products containing dimethyl diallyl ammonium chloride/acrylic acid-type polymers |
| US5067966A (en) * | 1988-12-23 | 1991-11-26 | Wella Aktiengesellschaft | 2-amino-6-chloro-4-nitro-phenol derivatives, process to their production and hair dyes containing those compounds |
| FR2687570A1 (en) * | 1992-02-21 | 1993-08-27 | Oreal | COSMETIC COMPOSITION BASED ON NON-IONIC SURFACTANT AGENTS AND CATIONIC OR AMPHOTERIC SUBSTANTIVE POLYMERS AND ITS USE AS A DYE OR DECOLORATION SUPPORT. |
| TW311089B (en) * | 1993-07-05 | 1997-07-21 | Ciba Sc Holding Ag | |
| US5393305A (en) * | 1993-08-26 | 1995-02-28 | Bristol-Myers Squibb Company | Two-part aqueous composition for coloring hair, which forms a gel on mixing of the two parts |
| TW325998B (en) * | 1993-11-30 | 1998-02-01 | Ciba Sc Holding Ag | Dyeing keratin-containing fibers |
| FR2713926B1 (en) * | 1993-12-22 | 1996-02-09 | Oreal | Process for the direct dyeing of human keratin fibers using sulfonic dyes and water vapor. |
| FR2717383B1 (en) * | 1994-03-21 | 1996-04-19 | Oreal | Composition for dyeing oxidation of keratin fibers comprising a derivative of paraphenylenediamine and a cationic or amphoteric substantive polymer and use. |
| DE69700686T2 (en) * | 1996-07-15 | 2000-04-06 | Kao Corp | Preparation for coloring human hair |
| FR2757385B1 (en) * | 1996-12-23 | 1999-01-29 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2757384B1 (en) * | 1996-12-23 | 1999-01-15 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2757387B1 (en) * | 1996-12-23 | 1999-01-29 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2757388B1 (en) * | 1996-12-23 | 1999-11-12 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
| US6007585A (en) * | 1997-10-15 | 1999-12-28 | Avlon Industries, Inc. | Hair brightening system |
| FR2778845B1 (en) * | 1998-05-25 | 2001-05-04 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND SUBSTANTIVE POLYMER |
| FR2779054B1 (en) | 1998-05-26 | 2001-06-29 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
-
1998
- 1998-05-25 FR FR9806549A patent/FR2778845B1/en not_active Expired - Fee Related
-
1999
- 1999-04-21 DE DE69920798T patent/DE69920798T2/en not_active Expired - Fee Related
- 1999-04-21 EP EP99400978A patent/EP0960617B1/en not_active Expired - Lifetime
- 1999-04-21 AT AT99400978T patent/ATE278377T1/en not_active IP Right Cessation
- 1999-04-21 ES ES99400978T patent/ES2230813T3/en not_active Expired - Lifetime
- 1999-04-23 AU AU23918/99A patent/AU726541B2/en not_active Ceased
- 1999-04-26 ZA ZA9902935A patent/ZA992935B/en unknown
- 1999-05-07 BR BR9902311-3A patent/BR9902311A/en not_active IP Right Cessation
- 1999-05-20 CA CA002272831A patent/CA2272831A1/en not_active Abandoned
- 1999-05-21 AR ARP990102425A patent/AR019309A1/en not_active Application Discontinuation
- 1999-05-21 HU HU9901703A patent/HUP9901703A3/en unknown
- 1999-05-21 MX MX9904755A patent/MX216728B/en not_active IP Right Cessation
- 1999-05-21 KR KR19990018508A patent/KR100330384B1/en not_active Expired - Fee Related
- 1999-05-24 CN CN99107017A patent/CN1236608A/en active Pending
- 1999-05-24 RU RU99110739/14A patent/RU2166311C2/en not_active IP Right Cessation
- 1999-05-24 PL PL99333321A patent/PL333321A1/en unknown
- 1999-05-25 JP JP11145014A patent/JP2000007542A/en active Pending
- 1999-05-25 US US09/318,209 patent/US6592633B2/en not_active Expired - Fee Related
-
2003
- 2003-05-21 US US10/442,211 patent/US6899739B2/en not_active Expired - Fee Related
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