MXPA99003129A - 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
- MXPA99003129A MXPA99003129A MXPA/A/1999/003129A MX9903129A MXPA99003129A MX PA99003129 A MXPA99003129 A MX PA99003129A MX 9903129 A MX9903129 A MX 9903129A MX PA99003129 A MXPA99003129 A MX PA99003129A
- Authority
- MX
- Mexico
- Prior art keywords
- composition
- dyeing
- composition according
- carbon atoms
- radical
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 238000004043 dyeing Methods 0.000 title claims abstract description 79
- 229920000642 polymer Polymers 0.000 title claims abstract description 49
- 239000000835 fiber Substances 0.000 title claims abstract description 34
- 125000002091 cationic group Chemical group 0.000 title claims description 45
- 238000004040 coloring Methods 0.000 title description 5
- 102000011782 Keratins Human genes 0.000 claims abstract description 27
- 108010076876 Keratins Proteins 0.000 claims abstract description 27
- 241000282414 Homo sapiens Species 0.000 claims abstract description 11
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 42
- 239000000975 dye Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 21
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 21
- 238000007254 oxidation reaction Methods 0.000 claims description 21
- 239000000982 direct dye Substances 0.000 claims description 19
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-Dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 230000000875 corresponding Effects 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
- 229920000289 Polyquaternium Polymers 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000002453 shampoo Substances 0.000 claims description 7
- -1 acrylic acid halide Chemical class 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 229920001519 homopolymer Polymers 0.000 claims description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical group CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 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 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 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 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N Cyano radical Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl radical Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 101700035385 lili Proteins 0.000 claims description 2
- 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 2
- 125000004429 atoms Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- IGJVJJYVRVZWBP-UHFFFAOYSA-O C(C(=C)C)(=O)OCC[NH2+]C(C(C)C)=O Chemical compound C(C(=C)C)(=O)OCC[NH2+]C(C(C)C)=O IGJVJJYVRVZWBP-UHFFFAOYSA-O 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000002585 base Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N Oleyl alcohol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-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
- BQMFRJXCPLVEND-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;2-(methylamino)ethyl 2-methylprop-2-enoate Chemical compound C=CN1CCCC1=O.CNCCOC(=O)C(C)=C BQMFRJXCPLVEND-UHFFFAOYSA-N 0.000 description 2
- 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
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 102000014961 Protein Precursors Human genes 0.000 description 2
- 108010078762 Protein Precursors Proteins 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N Xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 230000016571 aggressive behavior Effects 0.000 description 2
- 230000003113 alkalizing Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 230000002335 preservative Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-Naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-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
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1H-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- CWSZBVAUYPTXTG-UHFFFAOYSA-N 5-[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-[4-hydroxy-3-(2-hydroxyethoxy)-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OCCO)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 CWSZBVAUYPTXTG-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L 7681-57-4 Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N Aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- GAICDFZAFKJKLG-UHFFFAOYSA-M C(C(=C)C)(=O)[O-].C(C(=C)C)(=O)OCC[N+](C)(C)C Chemical compound C(C(=C)C)(=O)[O-].C(C(=C)C)(=O)OCC[N+](C)(C)C GAICDFZAFKJKLG-UHFFFAOYSA-M 0.000 description 1
- GCAYAPOBOHFAOE-UHFFFAOYSA-N C(CCC(=O)N(CCCCCCCCCCCC)N)(=O)OCCCN(CC)CC Chemical compound C(CCC(=O)N(CCCCCCCCCCCC)N)(=O)OCCCN(CC)CC GCAYAPOBOHFAOE-UHFFFAOYSA-N 0.000 description 1
- HQLVRJJDJGNYQW-UHFFFAOYSA-O CC=C[NH+]1C=NC=C1 Chemical compound CC=C[NH+]1C=NC=C1 HQLVRJJDJGNYQW-UHFFFAOYSA-O 0.000 description 1
- 210000001736 Capillaries Anatomy 0.000 description 1
- 229940106189 Ceramides Drugs 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N Dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N Hydrogen peroxide - urea Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 108010029541 Laccase Proteins 0.000 description 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 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 108090000437 Peroxidases Proteins 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N Phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 229960005323 Phenoxyethanol Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000240 adjuvant Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 230000003078 antioxidant Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 150000001783 ceramides Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000295 complement Effects 0.000 description 1
- 230000003750 conditioning Effects 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-O dodecyl(dimethyl)azanium Chemical group CCCCCCCCCCCC[NH+](C)C YWFWDNVOPHGWMX-UHFFFAOYSA-O 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 210000003702 immature single positive T cell Anatomy 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LRPCLTPZMUIPFK-UHFFFAOYSA-L methane;sulfate Chemical compound C.[O-]S([O-])(=O)=O LRPCLTPZMUIPFK-UHFFFAOYSA-L 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000149 penetrating Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920002553 poly(2-methacrylolyloxyethyltrimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940075420 xanthine Drugs 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 canonical dye of the given formula, and which is characterized by the fact that it also contains at least one particular canonical or amphoteric subjective polymer. The invention also relates to the dyeing methods and devices used by the
Description
COMPOSITION OF DYEING FOR KERATINIC FIBERS WITH A CATIONIC DIRECT COLORING AND A SUBSTANTPOLYMER
FIELD OF THE INVENTION 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 g formula, and at least one cationic substantpolymer to particular amphoteric. BACKGROUND OF THE INVENTION The invention also has as its object the dyeing methods and devices that use said composition. In the capillary field, two types of coloration can be distinguished. The first is the semi-permanent to temporary coloration, direct coloration, which uses dyes that are able to provide natural hair color, a more or less pronounced color modification resistant eventually to several shampoos. These dyes are called direct dyes, they can be made with or without oxidizing agent. In the presence of oxidant, the purpose is to obtain a lightening coloration. The i REF .: 29929
Ambering is carried out by applying to the hair the extemporaneous mixture of a direct dye and an oxidant and makes it possible in particular to obtain, by clearing the melanin of the hair, an advantageous effect such as a uniform color in the case of the gray hair to be highlighted the color in the case of naturally pigmented hair. The second is permanent coloring or oxidation coloring. This is carried out with dyes called "oxidation" which comprise oxidation dye precursors and copulators. Oxidation staining precursors, commonly called "oxidation bases", are initially colorless or sparsely 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 compounds colored and dyes. The formation of these colored compounds and dyes results either from an oxidatcondensation of the "oxidation bases" on themselves, or from an oxidatcondensation of the "oxidation bases" on coloring modifying compounds commonly called "couplers" and usually
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 direct dyes are added. Among the cationic direct dyes available in the field of dyeing of particularly human keratin fibers, the compounds whose structure is developed in the text that follows are already known; however, these dyes lead to colorations that still have insufficient characteristics, while at the same time in the plane of the homogeneity of the color distributed along the fiber, ("unison"), it is said then that the coloration is too select as in the plane of tenacity, in terms of resistance to the various aggressions that the hair can experience (light, bad weather, shampooing). However, after important research carried out on the subject, the applicant now finishes discovering that it is possible to obtain new compositions for the dyeing of keratin fibers capable of leading to less selectcolorations and that better resist the various aggressions.
that the hair can undergo, associating at least one particular polymer, cationic or amphoteric noun in at least one cationic direct dye known from the prior art and with the formulas respecty defined below. This discovery forms the basis of the present invention. Description of the invention The present invention therefore has as its first object a composition for dyeing keratin fibers and in particular human keratin fibers such as hair, which include in a medium suitable for dyeing, (i) at least one direct cationic dye whose structure corresponds to the following formulas, characterized in that it also contains (ii) at least one particular cationic or amphoteric substantive polymer. (i) The cationic direct dye usable according to the present invention is a compound selected from those of formula (I), (II), (III), (III ') below: a) the compounds of formula (I) below:
in which
D represents a nitrogen atom or the group -CH,
Ri and R2, identical or different, represent a hydrogen atom; an alkyl radical of 1 to 4 carbon atoms, which can be substituted by a radical -CN, -OH or -NH2 or form with a carbon atom of the benzene ring a heterocycle optionally oxygenated or nitrogenated, which can be replaced by one or various alkyl radicals of 1 to 4 carbon atoms; a radical 4'-aminophenyl, R3 and R'3, identical or different, represent a hydrogen or halogen atom selected from chlorine, bromine, iodine and fluorine, a cyano radical, alkoxy of 1 to 4 carbon atoms, carbon or acetyloxy, X 'represents an anion preferably chosen from chloride, methyl sulfate and acetate, A represents a group selected by the following structures Al a Al9
* 2. 3
A7 A *,
A "A12
13 14 A. 15
^ 16 to 18
in which R represents an alkyl radical of 1 to 4 carbon atoms which can be substituted by a hydroxyl radical and R 5 represents an alkoxy radical of 1 to 4 carbon atoms, with the proviso that when D represents -CH, A represents -ao A? 3 and R3 is different from an alkoxy radical, then Rx and R2 do not simultaneously designate a hydrogen atom; b) the compounds of formula (II) below:
wherein R6 represents a hydrogen atom or an alkyl radical of
1 to 4 carbon atoms, R7 represents a hydrogen atom, an alkyl radical which can be substituted by a -CN radical or by an amino group, a 4'-aminophenyl radical or a R6-a heterocycle optionally oxygenated and / or nitrogenated which can be substituted by an alkyl radical of 1 to 4 carbon atoms, R8 and R9, identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine or fluorine, a radical alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, a radical -CN, X 'represents an anion preferably chosen from chloride, methyl sulfate and acetate, B represents a group selected by the structures Bl a
B6 following:
in which R 10 represents an alkyl radical of 1 to 4 carbon atoms, Ru and R 2, which are identical or different, represent a hydrogen atom or a radical of 1 to 4 carbon atoms;
c) the following compounds of formulas (III) and (III '):
AND-
in which:
R13 represents a hydrogen atom, an alkoxy radical of 1 to 4 carbon atoms, a halogen atom such as bromine, chlorine, iodine or fluorine or an amino radical, Ri4 represents a hydrogen atom, an alkyl radical from 1 to 4 carbon atoms or form with a carbon atom of the benzene ring a heterocycle optionally oxygenated and / or substituted by one or more alkyl groups of 1 to 4 carbon atoms, Ris represents a hydrogen or halogen atom such as bromine, chlorine, iodine or fluorine, Rie and R17, identical or different, represent a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, Di and D2, identical or different, represent a nitrogen atom or the group -CH,
m - 0 or 1,
it being understood that when Ri3 represents an unsubstituted amino group, then Di and D2 simultaneously represent a group -CH and m = 0,
X 'represents an anion preferably chosen from chloride, methyl sulfate and acetate, E represents a group selected by the following El a E8 structures:
E6 E7 E8
wherein R 'represents an alkyl radical of 1 to 4 carbon atoms; when m = 0 and Di, represents a nitrogen atom, then E can also designate a group of structure E9 below:
wherein R 'represents an alkyl radical of 1 to 4 carbon atoms. Direct cationic dyes of formulas
(I), (II) and (III ') which can be used in the dyeing compositions according to the invention are known compounds and are described, for example, in patent applications WO 95/01772, WO 95/15144 and EP-A-0714 954. Among the direct cationic dyes of formula (I) which can be used in the dyeing compositions according to the invention, compounds which respond to the structures (I1) can be more particularly mentioned.
152) following:
Cl (126)
cr (141)
Among the compounds of structures (II) to (152) described above, compounds which respond to structures (II), (12), (114) and (131) are very particularly preferred. Among the direct cationic dyes of formula (II) which can be used in the dyeing compositions according to the invention, compounds which respond to the following structures (III) to (III2) can be mentioned more particularly:
Among the cationic direct dyes of formula (III), which can be used in the dyeing compositions according to the invention, compounds which respond to the following structures (III1) to (III18) can be mentioned more particularly:
Cl '(1115)
CH3SO4 (11113)
CHXOO "(une)
Among the particular compounds of structures (lili) to (III18) described above, compounds which respond to structures (III4), (III5) and (III3) are very particularly preferred.
Among the direct cationic dyes of formula (III ') which can be used in the dyeing compositions according to the invention, compounds which respond to the following structures (III' 1) to (III '3) can be mentioned more particularly:
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 selected from the group consisting of:
1 / - cationic cellulose derivatives with the exception of Polyquaternium 10; 2 / - the copolymers of dimethyldiallylammonium halide and (meth) acrylic acid; 3 / - methacryloyloxyethyltrimethylammonium halide homopolymers and copolymers; 4 / - polyammonium quaternary polymers selected from: - polymers consisting of recurring units corresponding to formula (IV) below:
CH, CH3
CH3 CH,
- polymers consisting of recurring units corresponding to formula (V) below:
CH, C2H5
CH, P2H5
- the polymers formed by recurring units corresponding to the following formula (VI):
(SAW)
wherein p designates an integer ranging from about 1 to about 6, D may be null or may represent a group - (CH2) r-CO- in which r denotes a number equal to 4 or to 7; 5 / - the vinylpyrrolidone copolymers with cationic units; 6 / - its mixtures. The substantive character (ie the behavior in the deposit on the hair) of the polymers used according to the invention was classically determined by means of the test described by Richard J. Crawford, Journal of the Society of Cosmetic Chemists, 1980, 31- ( 5) - pages 273 to 278 (developed by Red 80 acid dye).
These substantive polymers may be chosen from those previously described in the literature, in particular in the patent application EP-A-0557203, page 4, line 19, page 12, line 14. Mention may be made, among the derivatives cationic cellulosics, the quaternized cellulose ether derivatives such as those described in the application EP-A-0189 935, and in particular the polymer marketed under the name "Quatrisoft LM 200" by the Union Carbide Company; these polymers are also defined in the CTFA dictionary (5th edition, 1993) as quaternary ammonium hydroxyethylcellulose which has reacted with an epoxide substituted by a lauryldimethylammonium group and are repertoriated under the name of "Polyquaternium 24". Among the substantive polymers of the homopolymer and methacryloyloxyethyltrimethylammonium halide copolymer type usable according to the invention, the products referred to in the CTFA dictionary (5th edition, 1993) "Polyquaternium 35", "Polyquaternium 32" and "Polyquaternium 35", corresponding respectively to the "Polyquaternium 37", can be cited. to the crosslinked poly (methacryloyloxyethyltrimethylammonium chloride) homopolymer, in dispersion
50% in mineral oil, and sold under the name Saleare SC95 by the Allied Colloids Company, as regards "Polyquaternium 32", 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 as regards "Polyquaternium 35", methacryloyloxyethyltrimethyl-ammonium methacrylate and methacryloyloxyethyldimethylacetylammonium copolymer, sold under the name Plex 7525L by the Rohm GmbH Company. Among the substantive polymers of the type dimethyldiallylammonium halide copolymer and of (meth) acrylic acid which can be used according to the invention, mention may be made in particular of the copolymers of diallyldimethylammonium chloride and of acrylic acid, such as that of the proportions (80/20 by weight) sold under the name Merquat 280 by the Calgon Society. Among the substantive polymers of the quaternary polyammonium type which can be used according to the invention, mention may be made in particular of: the polymers prepared and described in French Patent 2 270,846, consisting of recurring units corresponding to the following formula (IV):
CH, CH,
CH3 CH3
and particularly those whose molecular weight, determined by gel permeation chromatography, is between 9500 and 9900; -the polymers prepared and described in the French patent 2 270 846, consisting of recurring units corresponding to the following formula (V):
CH, C, 2Hp5
CH3 C2H5
and particularly those whose molecular weight, determined by gel permeation chromatography, is about 1200; - the polymers described and prepared in US Patents 4,157,388, 4,390,689, 4,702,906, 4,719,282, and
constituted -by recurring units that respond to the following formula (VI):
where p designates an integer, which varies from 1 to 6 approximately, D can be null or can represent a group - (CH2) r-C0- in which r designates a number equal to 4 or 7, the mass being molecular weight of said polymers preferably less than 100 000, and more preferably still internal or equal to 50 000; such polymers are sold in particular by the Miranol Company under the names "Mirapol A15", "Mirapol AD1", "Mirapol AZI" and "Mirapol 175". Among the polymers of vinylpyrrolidone (PVP) swon cationic units usable according to the invention, mention may be made in particular of: a) vinylpyrrolidone polymers including dimethylaminoethyl methacrylate units; they can be cited among these;
the copolymer, vinylpyrrolidone / dimethylaminoethyl methacrylate (20/80 by weight) sold under the trade name COPOLYMER 845 by the Company I.S.P. the vinylpyrrolidone / dimethylaminoethyl methacrylate copolymers quaternized by diethyl sulfate, sold under the names GAFQUAT 734, 755, 755 S and 755 L by the company I.S.P. - the PVP / dimethylaminoethyl ethacrylate / hydrophilic polyurethane sold under the trade name PECOGEL GC-310 by the U.C.I.B. or even under the names AQUAMERE C 1031 and C 1511 by the company BLAGDEN CHEMICALS, - the PVP / methacrylate dimethylaminoethyl / olefin of 8 to 16 carbon atoms, quaternized or non-quaternized, sold under the names GANEX ACP 1050 to 1057, 1062 to 1069, 1079 to 1086, by the ISP Society
- the PVP / dimethylaminoethylmethacrylate / vinylcaprolactam, sold under the name GAFFIX VC 713 by the Company I.S.P.
b) vinylpyrrolidone polymers comprising methacrylamidopropyltrimethylammonium units (M.A. P.T.A.C.), among which may be mentioned in particular: vinylpyrrolidone / M.A copolymers. P.T.A.C. , sold under the trade names GAFQUAT ACP 1011 and GAFQUAT HS 100 by the I.S.P. c) vinylpyrrolidone polymers comprising methyl vinylimidazolium units and among which may be more particularly cited: - PVP / methylvinylimidazolium chloride, sold under the names LUVIQUAT FC 370, FC 550, FC 905, HM 552 by the Company B.A.S.F. - the PVP / methylvinylimidazolium chloride / vinylimidazole, sold, under the LUVIQUAT 8155 denamination by the B.A.S.F. the PVP / methylvinylimidazolium methanesulfate sold under the name LUVIQUAT MS 370 by the Company B.A.S.F. The concentration of substantive polymer (ii) in the dyeing composition according to the invention may vary between about 0.01 and about 10% relative to the total weight of the dye composition, and preferably between 0.1 and 5%. The appropriate medium for dyeing (or support) is generally constituted by water or a mixture of water
and by at least one organic solvent to solubilize compounds that are not sufficiently soluble in water. As the organic solvent, there may be mentioned, for example, the lower alkanols of 1 to 4 carbon atoms, such as ethanol and isopropanol; aromatic alcohols such as benzyl alcohol or phenoxyethanol, as well as analogous products and their mixtures. The solvents can 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 between 5 and 30% by weight approximately. The pH of the dyeing composition according to the invention is generally between approximately 2 and 11, and preferably between approximately 5 and approximately 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, lactic acid, sulfonic acids. Among alkalizing agents, mention may be made, by way of example, of ammonia, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula ( VII) next:
wherein W is a propylene moiety optionally substituted by a hydroxyl group or an alkyl radical of 1 to 6 carbon atoms; R 8, R 19, R 2 and R 21, identical or different, represent a hydrogen atom, an alkyl radical of 1 to 6 carbon atoms or hydroxyalkyl of 1 to 6 carbon atoms. The dyeing composition according to the invention can, in addition to the cationic direct dye (s)
(i) defined above, contain one or more additional direct dyes which may for example be
chosen from nitrated benzene dyes, anthraquinone dyes, naphthoquinone dyes, triarylmetanic dyes, xanthine 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 dyeing by oxidation and among which may be particularly mentioned para-phenylenediamines, bis-phenylalkylenediamines, 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 polymer, substantive (ii) as well as the oxidation bases, one or more couplers with the In order to modify or enrich with reflections the shades
obtained using the direct dye (s) cationic (s) (i) 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 the dye by oxidation and among which, metaphenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers can be particularly mentioned. When present, the copulator (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 optionally include various adjuvants conventionally used in the dyeing compositions of the hair, such as antioxidant agents, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, surfactants, smoke 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 dye composition according to the invention are not, or substantially, altered by the addition (s) considered. The dyeing composition according to the invention can be present 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 in particular human hair. The presentation in the form of a shampoo is particularly preferred. When the association of the cationic direct dye (ii) and the polymer, noun (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 several copulators) or when used in a composition intended for direct lightening dyeing, then the dyeing composition according to the invention further includes at least one oxidizing agent, selected for example between hydrogen peroxide, urea peroxide, alkali metals, persalts such as perborates and persulfates, and enzymes such as peroxidases, laccases and oxidoreductases of
two electrons. 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 dyeing, after which it is rinsed, it is eventually washed with shampoo, it is 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 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 cationic direct dye (i) as defined above and at least one oxidation base and, on the other hand, 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 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, for
another part, a composition (B2) that includes, in a medium suitable for dyeing, 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 cationic or amphoteric substantive polymer as defined above. Another object of the invention is a multi-compartment device or dye "kit" or any other multi-compartment conditioning system of which a first compartment includes the composition (Al) or (A2) as defined above and a second compartment includes the composition (Bl) or (B2) as defined above. These devices can be equipped with a means that allows to provide 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:
Direct cationic dye of formula 1 (2) 0.125 g
Paraaminophenol 0, 120 g
-N-β-hydroxyethylamino-2-methyl-phenol 0.125 g
Substantial polymer: copolymer of diallyldimethylammonium chloride and acrylic acid (80/20 by weight) sold under the name Merquat 280 by the company. CALGON 1.0 g M.A. *
Polyglycerolated oleic alcohol in 2 moles of glycerol 4.0 g Polyglycerolated oleic alcohol in 4 moles of glycerol, 78% of active substances (M.A.) 5.69g M.A. *
Oleic acid 3.0 g Oleic amines in 2 moles of ethylene oxide sold under the trade name ETHOMEEN 012 by AKZO Society 7, 0 g Diethylaminopropyl lauryl amino succinamate, sodium salt, 55% of M.A 3.0 g M.A.
Oleo alcohol 5.0 g Oleyl alcohol diethanolamide 12.0 g Propylene glycol 3.5 g Dipropylene glycol 0.5 g Propylene glycol monomethyl ether 9.0 g Ethanol 7.0 g
Sodium metabisulfite in aqueous solution, 35% of M.A 0.455g M.A. *
Ammonium acetate 0.8 g Antioxidant, sequestrant c. s. Perfume, preservative c. s. Ammonia at 20% NH3 10.0 g M.A. *: Active Material At the time of use, this composition was mixed with an equal amount of an aqueous solution of hydrogen peroxide in 20 volumes (6% by weight). The resulting composition was applied for 30 minutes on wicks of natural gray hair at 90% white. The hair strands were then rinsed, washed with a conventional shampoo and then dried. They were stained in a light blond tone with intense red reflection.
EXAMPLE 2: The following dye composition was prepared: Cationic direct dye of formula 1 (14) 0.09 g
Substantial polymer of quaternary polyammonium type of formula (IV) 1.0 g M.A. *
Nonyl phenol in 9 moles of ethylene oxide 8.0 g 2-amino-2-methyl-propanol c.s pH 9
Demineralized Aqua c.s.p 100 g M.A. : Active Matter The composition indicated above was applied for 30 minutes on wicks of natural gray hair with 90% white. The hair strands were then rinsed, washed with a conventional shampoo and then dried. They were stained in an intense copper color.
It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, property is claimed as contained in the following:
Claims (29)
1. Composition for dyeing keratin fibers and in particular human keratin fibers such as hair, characterized in that it includes in a medium suitable for dyeing, (i) at least one direct cationic dye of the following formulas (I), (II) ), (III), (III '): formula (I) in which: D represents a nitrogen atom or the group -CH, Ri and > , identical or different, represent a hydrogen atom; an alkyl radical of 1 to 4 carbon atoms which can be substituted by a radical -CN, -OH or -NH2 or form with a carbon atom of the benzene ring a heterocycle optionally oxygenated or nitrogenated, which can be replaced by one or more alkyl radicals of 1 to 4 carbon atoms; a radical 4'-aminophenyl, R3 and R'3, identical or different, represent an hydrogen or halogen selected from chlorine, bromine, iodine and fluorine, a cyano radical, alkoxy of 1 to 4 carbon atoms to acetyloxy, X "represents an anion preferably chosen from chloride, methyl sulfate and acetate, A represents a group selected by Al structures Al9 following: , A3 TO,, A1C A? 12 3 A 14 M5 M6? 17? 18 19 wherein R4 represents an alkyl radical of 1 to 4 carbon atoms which can be substituted by a hydroxyl radical and R5 represents an alkoxy radical of 1 to 4 carbon atoms, with the proviso that when D represents -CH, A represents s, o? 3 and R3 is different from an alkoxy radical, then Ri and R do not simultaneously designate a hydrogen atom; formula (II) in which: Re represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, R7 represents a hydrogen atom, an alkyl radical that can be substituted by a -CN radical or by a group amino, a 4'-aminophenyl radical to form with R6 an optionally oxygenated and / or nitrogenated heterocycle can be substituted by an alkyl radical of 1 to 4 carbon atoms, Rβ and 9, identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine to fluorine, an alkyl radical of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, a radical -CN, X "represents an anion preferably chosen from chloride, methyl sulfate and acetate, B represents a group selected by the structures Bl to B6 following: B4 B5 B6 in which Rio represents an alkyl radical of 1 to 4 carbon atoms, Rp and R12, identical or different represent a hydrogen atom or a radical of 1 to 4 carbon atoms; formulas (III) and (III ') in which: RX3 represents a hydrogen atom, an alkoxy radical of 1 to 4 carbon atoms, a halogen atom such as bromine, chlorine, iodine or fluorine or a amino radical, R 4, a halogen atom such as bromine, chlorine, iodine or fluorine or an amino radical, Ri 4 represents a hydrogen atom, an alkyl radical of 1 to 4 carbon atoms or an atom with a carbon, of the benzene ring a heterocycle optionally oxygenated and / or substituted by one or more alkyl groups of 1 to 4 carbon atoms, Ri5 represents a hydrogen or halogen atom such as bromine, chlorine, iodine or fluorine, Rie and 17, identical or different, represent an atom, of hydrogen or an alkyl radical of 1 to 4 carbon atoms, Di and D2, identical or different, represent a nitrogen atom or the group -CH, m = o or 1, it being understood that when R13 represents an unsubstituted amino group, then Di and D2 simultaneously represent a group -CH and m = 0, X "represents an anion of preference chosen from chloride, methyl sulfate and acetate, E represents a group selected by the structures El a E8 following: E6 E7 E8 wherein R 'represents an alkyl radical of 1 to 4 carbon atoms; when m = 0 and Di represents a nitrogen atom, then E may also designate a group of structure E9 below: wherein R 'represents an alkyl radical of 1 to 4 carbon atoms; said composition being characterized in that it also contains (ii) at least one cationic or amphoteric substantive polymer selected from the group consisting of: 1 / - cationic cellulose derivatives with the exception of Polyquaternium 10; 2 / -the copolymers of dimethyldiallylammonium halide and (meth) acrylic acid halide; 3 / - methacryloyloxyethyltrimethylammonium halide homopolymers and copolymers; 4 / - polyammonium quaternary polymers selected from: - polymers consisting of recurring units corresponding to formula (IV) below: CH, CH, 45 -. { -Ni- (CH2) 3-W * - (CH2) 6] (IV) C C CH CH, polymers consisting of recurring units corresponding to the following formula (V): CH, C2HS CH C, 2Hr, 5 the polymers constituted by recurring units corresponding to the following formula (VI): CH2? -0- (CH22) '2 (VI) wherein p designates an integer that varies from about 1 to about 6, D may be null or may represent a group - (CH2), -CO- in which r denotes a number equal to 4 or to 7; 5 / - vinylpyrralidone copolymers with cationic units; 6 / - its mixtures.
2. Composition according to claim 1, characterized in that the cationic direct dyes of formula (I) are chosen from the compounds that respond to the structures (II) to (152) below: 10 - fifteen twenty -
3. Composition according to claim 2, characterized in that the direct cationic dyes respond to structures (II), (12), (114), and (131).
4. Compositions according to claim 1, characterized in that the direct cationic dyes of formula (II) are chosen from the compounds that respond to structures (III) to (1112) below:
5. Composition according to claim 1, characterized in that the cationic direct dyes of formula (III) are chosen from among the compounds that respond to the following structures (lili) to (III18); CH3SO4 (11110)
6. Composition according to claim 5, characterized in that the direct cationic dyes of formula (III) are chosen from the compounds that respond to structures (III4), (III5) and (III13).
Composition according to claim 1, characterized in that the direct cationic dyes of formula (III ') are chosen from the compounds that respond to the structures (III' 1) a (III'3) following: Cl (lll'1)
8. Composition according to any one of the preceding claims, characterized in that the cationic direct dye (s) of formulas (I), (II), (III) or (III1) represent from 0.001 to 10% by weight of the total weight of the composition.
9. Composition according to claim 8, characterized in that the cationic direct dye (s) of formulas (I), (II), (III) or (III ') they represent from 0.005 to 5% by weight of the total weight of the composition.
10. Composition according to any one of the preceding claims, characterized in that the polymer substantive cellulose is a Polycuaternium 24.
11. Composition according to any one of claims 1 to 9, characterized in that the substantive polymer of the type copolymer of Dimethyldiallylammonium halide and (meth) acrylic acid halide is a copolymer of dimethyldiallylammonium chloride and acrylic acid (80/20 by weight).
12. Composition according to any one of claims 1 to 9, characterized in that the substantive polymers of the homopolymer and metatriloyloxyethyltrimethylammonium halide copolymer type are chosen from the crosslinked poly (methacryloyloxyethyltrimethylammonium chloride) homopolymer, in 50% dispersion in mineral oil, the crosslinked copolymer of the acrylamide and of methacryloyloxyethyltrimethylammonium chloride (20/80 by weight), in 50% dispersion in mineral oil, the methosulphate of the copolymer of methacryloyloxy'ethyltrimethylammonium and methacryloyloxyethyl-dimethylacetylammonium.
Composition according to any one of Claims 1 to 9, characterized in that the substantive polymers of the vinylpyrrolidone polymer type with cationic units are chosen from: a) vinylpyrrolidone polymers including dimethylaminoethyl methacrylate units; b) vinylpyrrolidone polymers comprising methacrylamidopropyltrimethylammonium units; c) vinylpyrrolidone polymers comprising methyl vinylimidazolium units.
Composition according to any one of claims 1 and 10 to 13, characterized in that the a substantive polymers (ii) represent from 0.01 to 10% by weight of the total weight of the composition.
15. Composition according to claim 14, characterized in that the substantive polymer (s) (ii) 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 medium suitable for dyeing (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 in that which is intended for oxidation dyeing and because it contains one to several oxidation bases selected from para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
Composition according to claim 18, characterized in that the oxidation base (s) represent from 0.0005 to 12% by weight of the total weight of the dyeing composition.
20. Composition according to claim 19, 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 18 to 20, characterized in that it includes one or more couplers selected from among the metaphenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers.
22. Composition according to claim 21, characterized in that the copulator (s) represent from 0.0001 to 10% by weight of the total weight of the dyeing composition.
Composition according to claim 22, characterized in that the coupler (s) represent from 0.005 to 5% by weight of the 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.
25, 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 24, for a sufficient time to develop the desired coloration, after which it is clarified, washed eventually with shampoo, rinsed again and dried.
26. Dyeing process of keratin fibers and in particular of human keratin fibers such as hair, characterized in that at least one dyeing composition as defined in any one of claims 1 to 24 is applied to the fibers, for a sufficient time to develop the desired coloration, without final rinse.
Method for dyeing keratin fibers and in particular human keratin fibers, such as hair, characterized in that it comprises a preliminary step consisting of storing separately a composition on the one hand (Al) comprising, in a medium suitable for dyeing, at least one direct cationic dye (i) as defined in the preceding claims and at least one oxidation base and, on the other hand, a composition (Bl) which includes, in a medium suitable 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 (Al) or the composition (Bl ) the substantive polymer (ii) as defined in the preceding claims.
28. Procedure for dyeing keratin fibers and in particular keratin fibers human beings such as hair, characterized in that it comprises 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 in the preceding claims and, on the other hand, a composition (B2) that includes, in a medium suitable for dyeing, at least one oxidizing agent, then in proceeding to its mixing at the time of the use before applying this mixture on the keratin fibers, the composition (A2) or composition (/ B2) containing the substantive polymer (ii) as defined in the preceding claims.
29. Multi-compartment multi-compartment dyeing kit, characterized by the fact that a first compartment includes composition (Al) or (A2) as defined in claim 27 or 28 and a second compartment includes the composition (Bl) or (B2) as defined in claim 27 or 28.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9804234 | 1998-04-06 | ||
FR9804234A FR2776923B1 (en) | 1998-04-06 | 1998-04-06 | DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND SUBSTANTIVE POLYMER |
Publications (3)
Publication Number | Publication Date |
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MX9903129A MX9903129A (en) | 2000-04-30 |
MXPA99003129A true MXPA99003129A (en) | 2000-07-01 |
MX231224B MX231224B (en) | 2005-10-10 |
Family
ID=9524889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX9903129A MX231224B (en) | 1998-04-06 | 1999-04-05 | COMPOSITION AND PROCEDURES FOR THE MAINTENANCE OF KERATIN FIBERS AND IN PARTICULAR HUMAN KERATIN FIBERS SUCH AS HAIRS AND A DEVICE OF VARIOUS COMPARTMENTS OR KIT OF VARIOUS COMPARTMENTS. |
Country Status (21)
Country | Link |
---|---|
US (3) | US20030019053A9 (en) |
EP (1) | EP0953334B1 (en) |
JP (2) | JP3899204B2 (en) |
KR (1) | KR100293004B1 (en) |
CN (1) | CN1289055C (en) |
AR (1) | AR017729A1 (en) |
AT (1) | ATE279903T1 (en) |
AU (1) | AU722097B2 (en) |
BR (1) | BR9901590B1 (en) |
CA (1) | CA2266053C (en) |
CZ (1) | CZ114599A3 (en) |
DE (1) | DE69921225T2 (en) |
DK (1) | DK0953334T3 (en) |
ES (1) | ES2232091T3 (en) |
FR (1) | FR2776923B1 (en) |
HU (1) | HUP9900867A3 (en) |
MX (1) | MX231224B (en) |
PL (3) | PL392259A1 (en) |
PT (1) | PT953334E (en) |
RU (1) | RU2160087C1 (en) |
ZA (1) | ZA992429B (en) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2776923B1 (en) * | 1998-04-06 | 2003-01-10 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND SUBSTANTIVE POLYMER |
KR20000021741A (en) * | 1998-09-30 | 2000-04-25 | 토니헬샴 | Method for preventing parking brake of construction heavy equipment from releasing |
DE10007776A1 (en) * | 2000-02-21 | 2001-09-06 | Goldwell Gmbh | Hair dye |
JP2001288054A (en) * | 2000-04-07 | 2001-10-16 | Kao Corp | 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 |
FR2825622B1 (en) | 2001-06-11 | 2007-06-29 | Oreal | COMPOSITION FOR DYING KERATIN FIBERS COMPRISING A PARTICULAR DIAZOIC DYE DYE |
FR2829926B1 (en) * | 2001-09-26 | 2004-10-01 | Oreal | COMPOSITION FOR DYEING KERATINIC FIBERS COMPRISING A SPECIAL DICATION DIAZOIC DYE |
FR2830189B1 (en) * | 2001-09-28 | 2004-10-01 | Oreal | LIGHTENING EFFECT DYE COMPOSITION FOR HUMAN KERATINIC FIBERS |
WO2004020530A1 (en) | 2002-08-30 | 2004-03-11 | Ciba Specialty Chemicals Holding Inc. | Coloured gloss pigments having at least one coating of siox, with x=0.03 to 0.95 for use in cosmetic and personal care formulations |
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 |
FR2848835B1 (en) * | 2002-12-19 | 2005-03-11 | Oreal | COMPOSITION FOR COLORING KERATIN FIBERS CONTAINING AN OXIDATION BASE AND A PARTICULAR POLYMER, PROCESS FOR THE PREPARATION OF SAID COMPOSITION AND METHOD FOR COLORING THE SAME |
FR2848834B1 (en) * | 2002-12-19 | 2005-03-11 | Oreal | COMPOSITION FOR COLORING KERATIN FIBERS CONTAINING A DIRECT DYE AND A PARTICULAR POLYMER, PROCESS FOR THE PREPARATION OF SAID COMPOSITION AND METHOD FOR COLORING THE SAME |
US7261744B2 (en) * | 2002-12-24 | 2007-08-28 | L'oreal S.A. | Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener |
US7250064B2 (en) * | 2003-04-01 | 2007-07-31 | L'oreal S.A. | Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof |
US7198650B2 (en) * | 2003-04-01 | 2007-04-03 | L'oreal S.A. | Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor |
FR2853238A1 (en) * | 2003-04-01 | 2004-10-08 | Oreal | COLORING CMPOSITION FOR HUMAN KERATINIC MATERIALS COMPRISING A FLUORESCENT COLORANT AND AN INSOLUBLE POLYORGANOSILOXANE CONDITIONING POLYMER, PROCESS AND USE |
US7195650B2 (en) * | 2003-04-01 | 2007-03-27 | L'oreal S.A. | Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye |
US7195651B2 (en) * | 2003-04-01 | 2007-03-27 | L'oreal S.A. | Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor |
US7186278B2 (en) * | 2003-04-01 | 2007-03-06 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor |
FR2853239B1 (en) * | 2003-04-01 | 2010-01-29 | Oreal | USE OF COMPOSITIONS COMPRISING A FLUORESCENT COLORANT AND A PARTICULARLY AMPHOTERIC OR NON-IONIC SURFACTANT FOR COLORING WITH A LIGHTENING EFFECT OF HUMAN KERATINIC MATERIALS |
FR2853237B1 (en) * | 2003-04-01 | 2006-07-14 | Oreal | METHOD FOR COLORING WITH LIGHTENING EFFECT OF HUMAN KERATIN FIBERS HAVING BEEN PERMANENT DEFORMATION BY MEANS OF A COMPOSITION COMPRISING A FLUORESCENT COLOR |
FR2853236B1 (en) * | 2003-04-01 | 2007-10-12 | Oreal | COLORING COMPOSITION FOR HUMAN KERATINIC MATERIALS COMPRISING A FLUORESCENT COLORANT AND A POLYOL, METHOD AND USE |
US7736631B2 (en) * | 2003-04-01 | 2010-06-15 | L'oreal S.A. | Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing |
US7208018B2 (en) * | 2003-04-01 | 2007-04-24 | L'oreal | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof |
FR2853233B1 (en) * | 2003-04-01 | 2007-10-05 | Oreal | COLORING COMPOSITION FOR HUMAN KERATINIC MATERIALS COMPRISING A FLUORESCENT COLORANT AND AN AMINO SILICONE, PROCESS AND USE |
FR2853235B1 (en) * | 2003-04-01 | 2008-10-03 | Oreal | COLORING COMPOSITION FOR HUMAN KERATINIC MATERIALS COMPRISING A FLUORESCENT COLOR AND A PARTICULAR COMPOUND HAVING ACID FUNCTION, METHOD AND USE |
US7150764B2 (en) * | 2003-04-01 | 2006-12-19 | L'oreal S.A. | Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof |
US7204860B2 (en) * | 2003-04-01 | 2007-04-17 | L'oreal | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof |
FR2853228B1 (en) * | 2003-04-01 | 2006-07-14 | Oreal | COLORING COMPOSITION FOR HUMAN KERATINIC MATERIALS COMPRISING FLUORESCENT COLORANT AND INSOLUBLE CONDITIONER AGENT, PROCESS AND USE |
US7192454B2 (en) * | 2003-04-01 | 2007-03-20 | L'oreal S.A. | Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof |
US7503939B2 (en) | 2004-02-03 | 2009-03-17 | Mitsubishi Pencil Co., Ltd. | Hair color |
DE102004005768A1 (en) * | 2004-02-05 | 2005-08-25 | Wella Ag | Pearlescent dye for keratin fibers |
DE102004006142A1 (en) * | 2004-02-07 | 2005-08-25 | Wella Ag | Neutral and cationic naphthalene derivatives and colorants for keratin fibers containing these compounds |
US20070274941A9 (en) * | 2004-07-16 | 2007-11-29 | Xavier Blin | Two-coat cosmetic product comprising at least one silicone polymer |
JP5063596B2 (en) | 2005-06-23 | 2012-10-31 | チバ ホールディング インコーポレーテッド | Nitrosulfide dye |
CN101300309B (en) | 2005-08-30 | 2013-01-16 | 西巴特殊化学制品控股公司 | Dyes containing a thiol group |
JP5254950B2 (en) * | 2006-03-24 | 2013-08-07 | ロレアル | Composition for dyeing comprising a thiol / disulfide fluorescent colorant containing a heterocyclic ring having an external cationic charge, and a method for lightening keratin materials using said colorant |
WO2007110534A2 (en) * | 2006-03-24 | 2007-10-04 | L'oréal | Dyeing composition comprising a thiol/disulphide fluorescent colorant having an external cationic charge, and method for lightening keratin materials using said colorant |
KR101088332B1 (en) * | 2006-03-24 | 2011-11-30 | 로레알 | Dyeing composition containing a thiol/disulphide fluorescent colorant comprising amine groups and having an internal cationic charge, and method for lightening keratin materials using said colorant |
EP2004755B1 (en) * | 2006-03-24 | 2011-08-03 | L'Oréal | Dyeing composition containing a thiol/disulphide fluorescent colorant having an external cationic charge and an interrupted alkylene chain, and method for lightening keratin materials using said colorant |
EP2001960B1 (en) * | 2006-03-24 | 2014-03-05 | L'Oréal | Dyeing composition containing a thiol/disulphide fluorescent colorant comprising an ortho-pyridinium group with an interrupted alkylene chain and an external cationic load, and method for lightening keratin materials using said colorant |
BRPI0712992A2 (en) | 2006-06-13 | 2012-04-17 | Ciba Holding Inc | three-color dyes |
GB0617024D0 (en) * | 2006-08-30 | 2006-10-11 | Unilever Plc | Hair treatment compositions incorporating hair substantive polymers |
US7780954B2 (en) * | 2008-02-19 | 2010-08-24 | Conopco, Inc. | Glow and sunless tanning color enhancement by cationic copolymers |
WO2011006946A2 (en) * | 2009-07-15 | 2011-01-20 | Basf Se | Polymeric hair dyes |
EP2415451A1 (en) * | 2010-08-05 | 2012-02-08 | KPSS-Kao Professional Salon Services GmbH | Cleansing composition |
FR2971937B1 (en) * | 2011-02-25 | 2013-02-15 | Oreal | COMPOSITION FOR COLORING KERATIN FIBERS COMPRISING A DIRECT DYE WITH DISULFURE / THIOL FUNCTION, A NON-CELLULOSIC THICKENING POLYMER, AN ALKALI AGENT, AND A REDUCING AGENT |
DE102011085906A1 (en) * | 2011-11-08 | 2013-05-08 | Henkel Ag & Co. Kgaa | Zwitterionic azo dyes for dyeing keratin-containing fibers |
KR102244166B1 (en) | 2013-09-02 | 2021-04-26 | 로레알 | Method for dyeing keratin fibres using cationic styryl disulphide dyes, and composition including said dyes |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4151162A (en) * | 1971-06-04 | 1979-04-24 | L'oreal | Diazomerocyanines and mesomeric forms thereof |
US3985499A (en) * | 1971-06-04 | 1976-10-12 | L'oreal | Diazamerocyanines for dyeing keratinous fibers |
LU70835A1 (en) * | 1974-08-30 | 1976-08-19 | ||
FR2140205B1 (en) * | 1971-06-04 | 1977-12-23 | Oreal | |
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 |
FR2471997B1 (en) * | 1979-12-21 | 1987-08-28 | Oreal | NOVEL POLYCATION POLYMERS, THEIR PREPARATION AND THEIR USE |
FR2471777A1 (en) * | 1979-12-21 | 1981-06-26 | Oreal | NOVEL COSMETIC AGENTS BASED ON POLYCATIONIC POLYMERS, AND THEIR USE IN COSMETIC COMPOSITIONS |
US4559057A (en) * | 1983-07-01 | 1985-12-17 | Clairol Incorporated | Process and composition for coloring hair with pigments |
US4663159A (en) | 1985-02-01 | 1987-05-05 | Union Carbide Corporation | Hydrophobe substituted, water-soluble cationic polysaccharides |
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 |
ATE96015T1 (en) | 1988-10-10 | 1993-11-15 | Blendax Werke Schneider Co | HAIR DYE AND HAIR TONING AGENTS. |
DE4129926C1 (en) * | 1991-09-09 | 1992-07-23 | Kao Corporation Gmbh, 4000 Duesseldorf, De | |
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 |
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. |
DE4421031A1 (en) * | 1994-06-16 | 1995-12-21 | Henkel Kgaa | Direct hair dye |
EP1219683B1 (en) | 1994-11-03 | 2004-03-24 | Ciba SC Holding AG | Cationic imidazolazo dyestuffs |
DE29512302U1 (en) * | 1995-07-31 | 1996-11-28 | Kao Corporation, Tokio/Tokyo | Means for tinting human hair |
DE19527978C2 (en) | 1995-07-31 | 1998-08-20 | Kao Corp | Means for coloring and tinting human hair and the use of hydroxy-C¶2¶_C¶4¶-alkyl guar gum in such agents |
PL329562A1 (en) | 1996-04-25 | 1999-03-29 | Oreal | Method of dyeing creatine fibres using precursors of oxidable dyes and powwdewred direct dyes |
ATE185967T1 (en) * | 1996-07-15 | 1999-11-15 | 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 |
FR2757387B1 (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 |
FR2757388B1 (en) * | 1996-12-23 | 1999-11-12 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
US5876412A (en) * | 1997-06-06 | 1999-03-02 | Piraka; Hadi A. | Surgical suturing device |
US6007585A (en) * | 1997-10-15 | 1999-12-28 | Avlon Industries, Inc. | Hair brightening system |
FR2776923B1 (en) * | 1998-04-06 | 2003-01-10 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS WITH CATIONIC DIRECT DYE AND SUBSTANTIVE POLYMER |
-
1998
- 1998-04-06 FR FR9804234A patent/FR2776923B1/en not_active Expired - Lifetime
-
1999
- 1999-03-23 DE DE69921225T patent/DE69921225T2/en not_active Revoked
- 1999-03-23 DK DK99400711T patent/DK0953334T3/en active
- 1999-03-23 PT PT99400711T patent/PT953334E/en unknown
- 1999-03-23 EP EP99400711A patent/EP0953334B1/en not_active Revoked
- 1999-03-23 ES ES99400711T patent/ES2232091T3/en not_active Expired - Lifetime
- 1999-03-23 AT AT99400711T patent/ATE279903T1/en not_active IP Right Cessation
- 1999-03-30 AU AU22540/99A patent/AU722097B2/en not_active Ceased
- 1999-03-30 ZA ZA9902429A patent/ZA992429B/en unknown
- 1999-03-31 CZ CZ991145A patent/CZ114599A3/en unknown
- 1999-04-01 CN CNB991073053A patent/CN1289055C/en not_active Expired - Fee Related
- 1999-04-02 PL PL392259A patent/PL392259A1/en not_active Application Discontinuation
- 1999-04-02 HU HU9900867A patent/HUP9900867A3/en unknown
- 1999-04-02 PL PL392260A patent/PL392260A1/en not_active Application Discontinuation
- 1999-04-02 PL PL99332363A patent/PL332363A1/en not_active IP Right Cessation
- 1999-04-05 MX MX9903129A patent/MX231224B/en active IP Right Grant
- 1999-04-05 AR ARP990101518A patent/AR017729A1/en active IP Right Grant
- 1999-04-05 RU RU99107636/14A patent/RU2160087C1/en not_active IP Right Cessation
- 1999-04-05 BR BRPI9901590-0B1A patent/BR9901590B1/en active IP Right Grant
- 1999-04-05 JP JP09757499A patent/JP3899204B2/en not_active Expired - Lifetime
- 1999-04-06 KR KR19990011879A patent/KR100293004B1/en not_active IP Right Cessation
- 1999-04-06 CA CA2266053A patent/CA2266053C/en not_active Expired - Fee Related
- 1999-04-06 US US09/287,176 patent/US20030019053A9/en not_active Abandoned
-
2004
- 2004-01-22 US US10/761,213 patent/US20040148711A1/en not_active Abandoned
-
2006
- 2006-03-06 JP JP2006060143A patent/JP4563947B2/en not_active Expired - Lifetime
-
2007
- 2007-03-28 US US11/727,834 patent/US7485157B2/en not_active Expired - Fee Related
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