DE10034812A1 - New N,N'-bis-(3-aminophenyl)-alkylene diamines and salts are used as coupler components in oxidation colorants for keratin fibers, e.g. wool, feathers and fur, and especially human hair - Google Patents
New N,N'-bis-(3-aminophenyl)-alkylene diamines and salts are used as coupler components in oxidation colorants for keratin fibers, e.g. wool, feathers and fur, and especially human hairInfo
- Publication number
- DE10034812A1 DE10034812A1 DE2000134812 DE10034812A DE10034812A1 DE 10034812 A1 DE10034812 A1 DE 10034812A1 DE 2000134812 DE2000134812 DE 2000134812 DE 10034812 A DE10034812 A DE 10034812A DE 10034812 A1 DE10034812 A1 DE 10034812A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- aminophenyl
- oxidation
- developer
- hair
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 28
- 230000003647 oxidation Effects 0.000 title claims abstract description 27
- 210000004209 hair Anatomy 0.000 title claims abstract description 24
- 239000003086 colorant Substances 0.000 title claims abstract description 15
- 150000003839 salts Chemical class 0.000 title claims abstract description 10
- 239000000835 fiber Substances 0.000 title claims abstract description 8
- 108010076876 Keratins Proteins 0.000 title claims abstract description 7
- 102000011782 Keratins Human genes 0.000 title claims abstract description 7
- 210000003746 feather Anatomy 0.000 title description 2
- 210000002268 wool Anatomy 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 22
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 6
- 239000000982 direct dye Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008365 aqueous carrier Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical class NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims description 2
- 150000005005 aminopyrimidines Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 150000004989 p-phenylenediamines Chemical class 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- 239000002243 precursor Substances 0.000 description 9
- 238000004040 coloring Methods 0.000 description 8
- 239000000118 hair dye Substances 0.000 description 8
- -1 heterocyclic hydrazones Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 description 3
- 229940113489 2,4-diaminophenoxyethanol Drugs 0.000 description 3
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- MWKPYVXITDAZLL-UHFFFAOYSA-N 4-[3-(2,4-diaminophenoxy)propoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1N MWKPYVXITDAZLL-UHFFFAOYSA-N 0.000 description 3
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 3
- OZCJSIBGTRKJGX-UHFFFAOYSA-N 4-methylcyclohexa-1,5-diene-1,4-diamine Chemical compound CC1(N)CC=C(N)C=C1 OZCJSIBGTRKJGX-UHFFFAOYSA-N 0.000 description 3
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 244000208060 Lawsonia inermis Species 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 3
- 229960001755 resorcinol Drugs 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- HHVMYUPMJJDVPG-UHFFFAOYSA-N 1-(2,5-diaminophenyl)ethanol Chemical compound CC(O)C1=CC(N)=CC=C1N HHVMYUPMJJDVPG-UHFFFAOYSA-N 0.000 description 2
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 description 2
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 2
- VVHJJADICJTYFU-UHFFFAOYSA-N 3-[4-(3-aminophenyl)piperazin-1-yl]aniline;hydrochloride Chemical compound Cl.NC1=CC=CC(N2CCN(CC2)C=2C=C(N)C=CC=2)=C1 VVHJJADICJTYFU-UHFFFAOYSA-N 0.000 description 2
- SYRZWFBWUASJJI-UHFFFAOYSA-N 3-amino-2,4-dichlorophenol Chemical compound NC1=C(Cl)C=CC(O)=C1Cl SYRZWFBWUASJJI-UHFFFAOYSA-N 0.000 description 2
- XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- ZQBHGSSAKLGUBH-UHFFFAOYSA-N 4,5,6-triamino-1h-pyrimidin-2-one Chemical compound NC1=NC(=O)NC(N)=C1N ZQBHGSSAKLGUBH-UHFFFAOYSA-N 0.000 description 2
- VTXBLQLZQLHDIL-UHFFFAOYSA-N 4-(3-hydroxypropylamino)-3-nitrophenol Chemical compound OCCCNC1=CC=C(O)C=C1[N+]([O-])=O VTXBLQLZQLHDIL-UHFFFAOYSA-N 0.000 description 2
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 description 2
- HLIGKHFHQXRAOX-UHFFFAOYSA-N 4-amino-2-[(5-amino-2-hydroxyphenyl)methyl]phenol Chemical compound NC1=CC=C(O)C(CC=2C(=CC=C(N)C=2)O)=C1 HLIGKHFHQXRAOX-UHFFFAOYSA-N 0.000 description 2
- BBTNLADSUVOPPN-UHFFFAOYSA-N 5,6-diaminouracil Chemical compound NC=1NC(=O)NC(=O)C=1N BBTNLADSUVOPPN-UHFFFAOYSA-N 0.000 description 2
- WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 description 2
- GHVHDYYKJYXFGU-UHFFFAOYSA-N Beta-Orcinol Chemical compound CC1=CC(O)=C(C)C(O)=C1 GHVHDYYKJYXFGU-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical class NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- BNQJVRXJLZUDMV-UHFFFAOYSA-N 1,1-diamino-1-(4-aminophenyl)propan-2-ol Chemical compound CC(O)C(N)(N)C1=CC=C(N)C=C1 BNQJVRXJLZUDMV-UHFFFAOYSA-N 0.000 description 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- VIXBPSTZNCRCJE-UHFFFAOYSA-N 1,3-bis[4-amino-n-(2-hydroxyethyl)anilino]propan-2-ol Chemical compound C1=CC(N)=CC=C1N(CCO)CC(O)CN(CCO)C1=CC=C(N)C=C1 VIXBPSTZNCRCJE-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- PJIOZYFAGNOQOF-UHFFFAOYSA-N 1-(2,5-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC(N)=CC=C1N PJIOZYFAGNOQOF-UHFFFAOYSA-N 0.000 description 1
- NLXFWUZKOOWWFD-UHFFFAOYSA-N 1-(2-hydroxyethylamino)-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NC NLXFWUZKOOWWFD-UHFFFAOYSA-N 0.000 description 1
- ICVRBKCRXNVOJC-UHFFFAOYSA-N 1-amino-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2NC ICVRBKCRXNVOJC-UHFFFAOYSA-N 0.000 description 1
- QFFLWFJPXWCDFQ-UHFFFAOYSA-N 1-butyl-2,3-dihydroindole-5,6-diol Chemical compound OC1=C(O)C=C2N(CCCC)CCC2=C1 QFFLWFJPXWCDFQ-UHFFFAOYSA-N 0.000 description 1
- ODEFWHTWLAESJT-UHFFFAOYSA-N 1-butylindole-5,6-diol Chemical compound OC1=C(O)C=C2N(CCCC)C=CC2=C1 ODEFWHTWLAESJT-UHFFFAOYSA-N 0.000 description 1
- YWVXDPWCLPPBSF-UHFFFAOYSA-N 1-ethyl-2,3-dihydroindole-5,6-diol Chemical compound OC1=C(O)C=C2N(CC)CCC2=C1 YWVXDPWCLPPBSF-UHFFFAOYSA-N 0.000 description 1
- OREUKLHWMRALGC-UHFFFAOYSA-N 1-methyl-2,3-dihydroindole-5,6-diol Chemical compound OC1=C(O)C=C2N(C)CCC2=C1 OREUKLHWMRALGC-UHFFFAOYSA-N 0.000 description 1
- HZIJNHVIXKKNIT-UHFFFAOYSA-N 1-n,2-n-bis(3-nitrophenyl)propane-1,2-diamine Chemical compound C=1C=CC([N+]([O-])=O)=CC=1NC(C)CNC1=CC=CC([N+]([O-])=O)=C1 HZIJNHVIXKKNIT-UHFFFAOYSA-N 0.000 description 1
- SVCXUHURTDIETO-UHFFFAOYSA-N 1-propyl-2,3-dihydroindole-5,6-diol Chemical compound OC1=C(O)C=C2N(CCC)CCC2=C1 SVCXUHURTDIETO-UHFFFAOYSA-N 0.000 description 1
- KGZSAZJZJMJKRX-UHFFFAOYSA-N 1-propylindole-5,6-diol Chemical compound OC1=C(O)C=C2N(CCC)C=CC2=C1 KGZSAZJZJMJKRX-UHFFFAOYSA-N 0.000 description 1
- MIMYTSWNVBMNRH-UHFFFAOYSA-N 1h-indol-6-amine Chemical compound NC1=CC=C2C=CNC2=C1 MIMYTSWNVBMNRH-UHFFFAOYSA-N 0.000 description 1
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
- MXXKDNVTCQXXHU-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-amine Chemical compound NC1=CC=CC2=C1CCN2 MXXKDNVTCQXXHU-UHFFFAOYSA-N 0.000 description 1
- UMXPKGQJQAQXLU-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-amine Chemical compound NC1=CC=C2CCNC2=C1 UMXPKGQJQAQXLU-UHFFFAOYSA-N 0.000 description 1
- JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 description 1
- KULOFVMDAJSPOK-UHFFFAOYSA-N 2-(2,5-diaminophenoxy)ethanol Chemical compound NC1=CC=C(N)C(OCCO)=C1 KULOFVMDAJSPOK-UHFFFAOYSA-N 0.000 description 1
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-UHFFFAOYSA-N 0.000 description 1
- KDBUTNSQYYLYOY-UHFFFAOYSA-N 2-(4,5-diaminopyrazol-1-yl)ethanol Chemical compound NC=1C=NN(CCO)C=1N KDBUTNSQYYLYOY-UHFFFAOYSA-N 0.000 description 1
- LGZSBRSLVPLNTM-UHFFFAOYSA-N 2-(4-amino-2-methyl-5-nitroanilino)ethanol Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1NCCO LGZSBRSLVPLNTM-UHFFFAOYSA-N 0.000 description 1
- YESOPQNVGIQNEV-UHFFFAOYSA-N 2-(4-amino-2-nitroanilino)benzoic acid Chemical compound [O-][N+](=O)C1=CC(N)=CC=C1NC1=CC=CC=C1C(O)=O YESOPQNVGIQNEV-UHFFFAOYSA-N 0.000 description 1
- NZKTVPCPQIEVQT-UHFFFAOYSA-N 2-[4-[(4-aminophenyl)diazenyl]-n-(2-hydroxyethyl)anilino]ethanol Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(N(CCO)CCO)C=C1 NZKTVPCPQIEVQT-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- YAIGMGRTYGNQAM-UHFFFAOYSA-N 3-[4-(3-aminophenyl)piperazin-1-yl]aniline Chemical compound NC1=CC=CC(N2CCN(CC2)C=2C=C(N)C=CC=2)=C1 YAIGMGRTYGNQAM-UHFFFAOYSA-N 0.000 description 1
- XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 description 1
- VSTCLRLLVRTSFH-UHFFFAOYSA-N 3-amino-6-methoxy-2-(methylamino)phenol Chemical compound CNC1=C(N)C=CC(OC)=C1O VSTCLRLLVRTSFH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/53—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino groups
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Abstract
Description
Die Erfindung betrifft neue N,N'-Bis-(3'-aminophenyl)-alkylendiamine und -diazacy cloalkane sowie deren Verwendung als Kupplerkomponenten zur Erzeugung von Oxidati onsfärbungen mit bekannten Entwicklerverbindungen.The invention relates to new N, N'-bis- (3'-aminophenyl) -alkylenediamines and -diazacy cloalkanes and their use as coupler components for generating oxidati ons staining with known developer compounds.
Für das Färben von Keratinfasern, insbesondere von Haaren, spielen die sogenannten Oxi dationsfärbemittel wegen ihrer intensiven Farben und guten Echtheitseigenschaften, die bei relativ niedriger Färbetemperatur und in kurzen Färbezeiten erzielt werden, eine besondere Rolle. Solche Färbemittel enthalten in einem geeigneten, meist wäßrigen Träger eine Oxi dationsbase, die auch als Entwicklerkomponente bezeichnet wird und die unter dem Ein fluß von Luftsauerstoff oder von Oxidationsmitteln durch oxidative Polymerisation einen Farbstoff ausbildet. Dieser Farbstoff kann durch Kupplung mit einer anderen Entwickler verbindung oder mit sogenannten Kupplerverbindungen, die selbst keine Farbstoffe ausbil den können, intensiviert und in der Nuance modifiziert werden.The so-called oxi play a role in dyeing keratin fibers, especially hair dation dyes because of their intense colors and good fastness properties relatively low dyeing temperature and can be achieved in short dyeing times, a special one Role. Such colorants contain an oxide in a suitable, usually aqueous, carrier dationsbase, which is also known as the developer component and which is available under the Ein a flow of atmospheric oxygen or of oxidizing agents through oxidative polymerization Forms dye. This dye can be made by coupling with another developer compound or with so-called coupler compounds that do not form any dyes themselves can be intensified and modified in the nuance.
Gute Oxidationsfarbstoffvorprodukte sollen in erster Linie folgende Voraussetzungen er füllen: Sie müssen bei der oxidativen Kupplung die gewünschten Farbnuancen in ausrei chender Intensität und Echtheit ausbilden. Sie müssen ferner ein gutes Aufziehvermögen auf die Faser besitzen, wobei insbesondere bei menschlichen Haaren keine merklichen Unterschiede zwischen strapaziertem und frisch nachgewachsenem Haar bestehen dürfen (Egalisiervermögen). Sie sollen beständig sein gegen Licht, Wärme, Reibung und den Ein fluß chemischer Reduktionsmittel, z. B. Dauerwellenflüssigkeiten. Schließlich sollen sie - falls als Haarfärbemittel zur Anwendung kommend - die Kopfhaut nicht zu sehr anfärben, und vor allem sollen sie in toxikologischer und dermatologischer Hinsicht unbedenklich sein. Weiterhin soll die erzielte Färbung durch Blondierung leicht wieder aus dem Haar entfernt werden können, falls sie doch nicht den individuellen Wünschen der einzelnen Person entspricht und rückgängig gemacht werden soll. Good oxidation dye precursors should primarily meet the following requirements fill: you have to get the desired color nuances in the oxidative coupling train with appropriate intensity and authenticity. You must also be able to pull yourself up on the fiber, with no noticeable in human hair in particular There may be differences between damaged and newly grown hair (Equalizing ability). They should be resistant to light, heat, friction and the onslaught flow of chemical reducing agents, e.g. B. Permanent wave fluids. After all, they should - if used as a hair dye - do not dye the scalp too much, and above all, they should be toxicologically and dermatologically harmless be. Furthermore, the coloring achieved should easily be removed from the hair by bleaching can be removed if they do not meet the individual needs of each Person corresponds and should be reversed.
Als Entwicklerkomponenten werden üblicherweise primäre aromatische Amine mit einer weiteren, in para- oder ortho-Position befindlichen, freien oder substituierten Hydroxy- oder Aminogruppe, Diaminopyridinderivate, heterocyclische Hydrazone, 4- Aminopyrazolonderivate sowie 2,4,5,6-Tetraaminopyrimidin und dessen Derivate einge setzt.Primary aromatic amines with a further, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4- Aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives are included puts.
Spezielle Vertreter sind beispielsweise p-Phenylendiamin, p-Toluylendiamin, 2,4,5,6-Te traaminopyrimidin, p-Aminophenol, N,N-Bis(2'-hydroxyethyl)-p-phenylendiamin, 2- (2',5'-Diaminophenyl)-ethanol, 2-(2',5'-Diaminophenoxy)-ethanol, 1-Phenyl-3-car boxyamido-4-amino-pyrazolon-5, 4-Amino-3-methylphenol, 2-Aminomethyl-4- aminophenol, 2-Hydroxy-4,5,6-triaminopyrimidin, 2,4-Dihydroxy-5,6-diaminopyrimidin, 2,5,6-Triamino-4-hydroxypyrimidin und 1,3-N,N'-Bis(2'-hydroxyethyl)-N,N'-bis(4'- aminophenyl)-diaminopropan-2-ol.Special representatives are, for example, p-phenylenediamine, p-tolylenediamine, 2,4,5,6-Te traaminopyrimidine, p-aminophenol, N, N-bis (2'-hydroxyethyl) -p-phenylenediamine, 2- (2 ', 5'-diaminophenyl) -ethanol, 2- (2', 5'-diaminophenoxy) -ethanol, 1-phenyl-3-car boxyamido-4-amino-pyrazolon-5, 4-amino-3-methylphenol, 2-aminomethyl-4- aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine and 1,3-N, N'-bis (2'-hydroxyethyl) -N, N'-bis (4'- aminophenyl) diaminopropan-2-ol.
Als Kupplerkomponenten werden in der Regel m-Phenylendiaminderivate, Naphthole, Re sorcin und Resorcinderivate, Pyrazolone und m-Aminophenole verwendet. Als Kuppler substanzen eignen sich insbesondere 1-Naphthol, 1,5-, 2,7- und 1,7-Dihydroxynaphthalin, 5-Amino-2-methylphenol, m-Aminophenol, Resorcin, Resorcinmonomethylether, m- Phenylendiamin, 1-Phenyl-3-methyl-pyrazolon-5, 2,4-Dichlor-3-aminophenol, 1,3-Bis- (2,4-diaminophenoxy)-propan, 2-Chlor-resorcin, 4-Chlor-resorcin, 2-Chlor-6-methyl-3- aminophenol, 2-Methylresorcin, 5-Methylresorcin, 2-Methyl-4-chlor-5-aminophenol, 2,4- Diaminophenoxyethanol und 2-Amino-3-Hydroxypyridin.As a rule, m-phenylenediamine derivatives, naphthols, Re sorcin and resorcinol derivatives, pyrazolones and m-aminophenols are used. As a matchmaker substances are particularly suitable 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethylether, m- Phenylenediamine, 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2,4-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro-6-methyl-3- aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2-methyl-4-chloro-5-aminophenol, 2,4- Diaminophenoxyethanol and 2-amino-3-hydroxypyridine.
Allein mit einer Entwicklerkomponente oder einer speziellen Kuppler/Entwickler- Kombination gelingt es in der Regel nicht, eine auf dem Haar natürlich wirkende Farbnu ance zu erhalten. In der Praxis werden daher üblicherweise Kombinationen verschiedener Entwicklerkomponenten und Kupplerkomponenten eingesetzt. Es besteht daher ständig Bedarf an neuen, verbesserten Farbstoff-Vorprodukten.Alone with a developer component or a special coupler / developer The combination does not usually succeed in creating a color that looks natural on the hair to get ance. In practice, therefore, combinations of different Developer components and coupler components used. It therefore persists Need for new, improved dye precursors.
Aus DE 29 34 329 C2 waren N,N'-Bis-(4'-methoxy-5'-aminophenyl)-alkylendiamine als Kuppler für Oxidationshaarfärbemittel bekannt. Die dort offenbarten Kuppler machen aber noch nicht alle erwünschten Farbnuancierungen zugänglich. Sie weisen auch nicht die ge forderten Echtheitseigenschaften auf. Es bestand daher die Aufgabe, neue Kupplerverbindungen zu finden, die mit den gängigen Entwicklerkomponenten zu besonders intensiven Oxidationsfärbungen mit hohen Licht- und Waschechtheitseigenschaften und günstigeren dermatologischen Eigenschaften führen.From DE 29 34 329 C2 N, N'-bis (4'-methoxy-5'-aminophenyl) -alkylenediamines were as Coupler for oxidation hair dye known. The couplers revealed there do, however Not all desired color nuances are available yet. They also do not have the ge requested authenticity properties. The task was therefore to find new coupler compounds to find that with the common developer components to be particularly intensive Oxidation dyeings with high light and washfastness properties and cheaper ones dermatological properties lead.
Gegenstand der Erfindung sind N.N'-Bis-(3-aminophenyl)-alkylendiamine- oder -diazacy
cloalkane der allgemeinen Formel I oder II,
The invention relates to N.N'-bis (3-aminophenyl) alkylenediamines or diazacy cloalkanes of the general formula I or II,
in welchen R1, R2 und R3 unabhängig voneinander Wasserstoff, C1-C4-Alkylgruppen oder C2-C4-Hydroxyalkylgruppen und R3 auch eine C2-C4-Alkoxy- oder Hydroxyalkoxygruppe sein kann, n eine ganze Zahl von 2-8 und x = 2 oder 3 ist, und deren wasserlösliche Salze.in which R 1 , R 2 and R 3 independently of one another hydrogen, C 1 -C 4 -alkyl groups or C 2 -C 4 -hydroxyalkyl groups and R 3 can also be a C 2 -C 4 -alkoxy or hydroxyalkoxy group, n is a whole Number from 2-8 and x = 2 or 3, and their water-soluble salts.
Es wurde nun gefunden, daß diese neuen N,N'-Bis-(3-aminophenyl)-alkylendiamine- oder diazacycloalkane sich in besonders vorteilhafter Weise als Kupplerverbindungen zur Er zeugung von Oxidationsfärbungen mit bekannten Entwicklerkomponenten eignen. Ein besonders bevorzugter Gegenstand der Erfindung sind N,N'-Bis-(3-aminophenyl)- alkylendiamine und diazacycloalkane der Formeln I oder II, in welchen R1, R2 und R3 Wasserstoff sind und n = eine ganze Zahl von 2-4 und X = 2 ist. Diese bevorzugten Verbin dungen liefern mit üblichen Oxidationsbasen intensive gelbe, rötliche und blaue Nuancen von hoher Echtheit. Die erfindungsgemäßen Verbindungen der Formeln I und II eignen sich insbesondere zur Herstellung von Oxidationsfärbemitteln für Keratinfasern, bevorzugt fit Haare.It has now been found that these new N, N'-bis (3-aminophenyl) alkylenediamines or diazacycloalkanes are particularly advantageous as coupler compounds for generating oxidation colorations with known developer components. A particularly preferred subject of the invention are N, N'-bis (3-aminophenyl) alkylenediamines and diazacycloalkanes of the formulas I or II, in which R 1 , R 2 and R 3 are hydrogen and n = an integer from 2- 4 and X = 2. With conventional oxidation bases, these preferred compounds produce intense yellow, reddish and blue nuances of high authenticity. The compounds of the formulas I and II according to the invention are particularly suitable for the production of oxidation colorants for keratin fibers, preferably fit hair.
Die neuen Kupplerverbindungen der Formeln I oder II können als freie Basen oder auch in Form ihrer wasserlöslichen Säureadditionssalze, z. B. als Hydrochloride, Sulfate, Phosphate, Lactate, Acetate oder Glycolate eingesetzt werden. The new coupler compounds of the formulas I or II can be used as free bases or in Form of their water-soluble acid addition salts, e.g. B. as hydrochloride, sulfate, phosphate, Lactates, acetates or glycolates can be used.
Ein weiterer Gegenstand der Erfindung sind daher Oxidationsfärbemittel für Keratinfasern, insbesondere für Haare, die in einem wäßrigen Träger wenigstens eine Entwicklerkomponente und wenigstens ein N,N'-Bis-(3-aminophenyl)-alkylendiamin- oder -diazacycloalkane der Formel I oder II oder deren wasserlösliche Salze als Kuppler enthalten. Unter Keratinfasern sind dabei Wolle, Federn und Pelze, insbesondere aber menschliche Haare zu verstehen.The invention therefore also relates to oxidation colorants for keratin fibers, especially for hair that contains at least one developer component in an aqueous vehicle and at least one N, N'-bis (3-aminophenyl) alkylenediamine or diazacycloalkane of Formula I or II or their water-soluble salts contain as couplers. Under keratin fibers are wool, feathers and furs, but especially human hair.
Geeignete Entwicklerverbindungen zur Herstellung der erfindungsgemäßen Haarfärbemittel sind z. B. p-Phenylendiamin, p-Toluylendiamin, 2,5-Diaminophenyl-ethanol, 2,5- Diaminophenoxy-ethanol, N,N-Bis(2'-hydroxyethyl)-p-phenylendiamin, p-Aminophenol, 3- Methyl-4-aminophenol, 2-Hydroxyethylaminomethyl-4-aminophenol, 2-Aminomethyl-4- aminophenol, 2-(2'-Hydroxyethoxy)-4-aminophenol, 2-Hydroxymethyl-4-aminophenol, Bis- (2-hydroxy-5-aminophenyl)-methan, N,N'-Bis-(2'-hydroxyethyl)-N,N'-bis-(4'-aminophenyl)- 1,3-diaminopropan-2-ol, 1-Phenyl-3-carboxyamido-4-amino-pyrazolon, 4,4'-Diamino diphenylamin, 1,4-Bis-4-aminophenyl-diazycloheptan, 4,5-Diamino-1(2'-hydroxyethyl)- pyrazol, 2,4,5,6-Tetraamino-pyrimidin, 2-Hydroxy-4,5,6-triaminopyrimidin, 4-Hydroxy- 2,5,6-triaminopyrimidin, 2,4-Dihydroxy-5,6-diaminopyrimidin, o-Aminophenole und o- Phenylendiamine.Suitable developer compounds for the preparation of the hair colorants according to the invention are z. B. p-phenylenediamine, p-tolylenediamine, 2,5-diaminophenyl-ethanol, 2,5- Diaminophenoxyethanol, N, N-bis (2'-hydroxyethyl) -p-phenylenediamine, p-aminophenol, 3- Methyl-4-aminophenol, 2-hydroxyethylaminomethyl-4-aminophenol, 2-aminomethyl-4- aminophenol, 2- (2'-hydroxyethoxy) -4-aminophenol, 2-hydroxymethyl-4-aminophenol, bis- (2-hydroxy-5-aminophenyl) -methane, N, N'-bis- (2'-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) - 1,3-diaminopropan-2-ol, 1-phenyl-3-carboxyamido-4-aminopyrazolone, 4,4'-diamino diphenylamine, 1,4-bis-4-aminophenyl-diazycloheptane, 4,5-diamino-1 (2'-hydroxyethyl) - pyrazole, 2,4,5,6-tetraamino-pyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy- 2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, o-aminophenols and o- Phenylenediamines.
Zur Nuancierung können die erfindungsgemäßen Oxidationsfärbemittel weitere übliche Kupplerverbindungen und gegebenenfalls auch Direktfarbstoffe enthalten.The oxidation colorants according to the invention can be further customary for shading purposes Contain coupler compounds and optionally also direct dyes.
Erfindungsgemäß bevorzugte Kupplerkomponenten sind 1-Naphthol, Pyrogallol, 1,5-, 2,7- und 1,7-Dihydroxynaphthalin, o-Aminophenol, 5-Amino-2-methylphenol, m-Aminophe nol, Resorcin, Resorcinmonomethylether, m-Phenylendiamin, 1-Phenyl-3-methyl-pyrazo lon-5, 2,4-Dichlor-3-aminophenol, 1,3-Bis-(2',4'-diaminophenoxy)-propan, 4-Chlorresor cin, 2-Chlor-6-methyl-3-aminophenol, 2-Methylresorcin, 5-Methylresorcin, 2,5- Dimethylresorcin, 2,6-Dihydroxypyridin, 2,6-Diaminopyridin, 2-Amino-3- hydroxypyridin, 2,6-Dihydroxy-3,4-diaminopyridin, 3-Amino-2-methylamino-6- methoxypyridin, 4-Amino-2-hydroxytoluol, 2,6-Bis-(2'-hydroxyethylamino)-toluol, 2,4- Diaminophenoxyethanol, 1-Methoxy-2-amino-4-(2'-hydroxyethylamino)-benzol, 2- Methyl-4-chlor-5-amino-phenol, 6-Met-hyl-1,2,3,4-tetrahydro-chinoxalin, 3,4- Methylendioxyphenol, 3,4-Methylendioxyanilin, 2,6-Dimethyl-3-amino-phenol, 3-Amino- 6-methoxy-2-methylaminophenol, 2-Hydroxy-4-aminophenoxyethanol, 2-Methyl-5-(2'- hydroxyethylamino)-phenol und 2,6-Dihydroxy-3,4-dimethylpyridin. According to the invention preferred coupler components are 1-naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, o-aminophenol, 5-amino-2-methylphenol, m-aminophe nol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazo ion-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2 ', 4'-diaminophenoxy) propane, 4-chlorine resor cin, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5- Dimethylresorcinol, 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2-amino-3- hydroxypyridine, 2,6-dihydroxy-3,4-diaminopyridine, 3-amino-2-methylamino-6- methoxypyridine, 4-amino-2-hydroxytoluene, 2,6-bis- (2'-hydroxyethylamino) -toluene, 2,4- Diaminophenoxyethanol, 1-methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 2- Methyl-4-chloro-5-aminophenol, 6-methyl-1,2,3,4-tetrahydroquinoxaline, 3,4- Methylenedioxyphenol, 3,4-methylenedioxyaniline, 2,6-dimethyl-3-aminophenol, 3-amino- 6-methoxy-2-methylaminophenol, 2-hydroxy-4-aminophenoxyethanol, 2-methyl-5- (2'- hydroxyethylamino) phenol and 2,6-dihydroxy-3,4-dimethylpyridine.
Darüber hinaus können zur Erzielung bestimmter Färbewirkungen auch direktziehende Farbstoffe verwendet werden.In addition, direct coloring can be used to achieve certain coloring effects Dyes are used.
In einer bevorzugten Ausführungsform enthalten die erfindungsgemäßen Haarfärbemittel zur weiteren Modifizierung der Farbnuancen neben den Oxidationsfarbstoffvorprodukten zusätzlich übliche direktziehende Farbstoffe, z. B. aus der Gruppe der Nitrophenylendiamine, Nitroaminophenole, Anthrachinone oder Indophenole, wie z. B. die unter den internationalen Bezeichnungen bzw. Handelsnamen HC Yellow 2, HC Yellow 4, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Nitroblau, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16, Pikraminsäure und Rodol 9 R bekannten Verbindungen, in einer Menge von 0,01 bis 20 Gew.-%, bezogen auf das gesamte Oxidationshaarfärbemittel. 4-Amino-2-nitro diphenylamin-2'-carbonsäure, 6-Nitro-1,2,3,4-tetrahydrochinoxalin, Rodol 9 R und HC Red BN sind erfindungsgemäß besonders bevorzugte direktziehende Farbstoffe.In a preferred embodiment, the hair colorants according to the invention contain for further modification of the color nuances in addition to the oxidation dye precursors additional conventional substantive dyes, e.g. B. from the group of nitrophenylenediamines, Nitroaminophenols, anthraquinones or indophenols, such as. B. those among the international Designations or trade names HC Yellow 2, HC Yellow 4, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Nitro Blue, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16, picric acid and Rodol 9 R known compounds, in an amount of 0.01 up to 20% by weight, based on the total oxidation hair colorant. 4-amino-2-nitro diphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, Rodol 9 R and HC Red BN are substantive dyes which are particularly preferred according to the invention.
Weiterhin können die erfindungsgemäßen Zubereitungen auch in der Natur vorkommende Farbstoffe wie beispielsweise Henna rot, Henna neutral, Henna schwarz, Kamillenblüte, Sandelholz, schwarzen Tee, Faulbaumrinde, Salbei, Blauholz, Krappwurzel, Catechu, Sedre und Alkannawurzel enthalten.Furthermore, the preparations according to the invention can also occur naturally Dyes such as red henna, neutral henna, black henna, chamomile blossom, Sandalwood, black tea, buckthorn bark, sage, blue wood, madder root, catechu, Contains sedre and alkanna root.
Weitere in den erfindungsgemäßen Färbemitteln enthaltene Farbstoffkomponenten können auch Indole und Indoline, sowie deren physiologisch verträgliche Salze, sein. Bevorzugte Beispiele sind 5,6-Dihydroxyindol, N-Methyl-5,6-dihydroxyindol, N-Ethyl-5,6-dihy droxyindol, N-Propyl-5,6-dihydroxyindol, N-Butyl-5,6-dihydroxyindol, 5,6- Dihydroxyindol-2-carbonsäure, 6-Hydroxyindol, 6-Aminoindol und 4-Aminoindol. Wei terhin bevorzugt sind 5,6-Dihydroxyindolin, N-Methyl-5,6-dihydroxyindolin, N-Ethyl-5,6- dihydroxyindolin, N-Propyl-5,6-dihydroxyindolin, N-Butyl-5,6-dihydroxyindolin, 5,6- Dihydroxyindolin-2-carbonsäure, 6-Hydroxyindolin, 6-Aminoindolin und 4-Aminoindolin.Further dye components contained in the colorants according to the invention can also indoles and indolines, as well as their physiologically tolerable salts. Preferred Examples are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihy droxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6- Dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole. White furthermore preferred are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6- dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 5,6- Dihydroxyindoline-2-carboxylic acid, 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
Es ist nicht erforderlich, daß die Oxidationsfarbstoffvorprodukte oder die direktziehenden Farbstoffe jeweils einheitliche Verbindungen darstellen. Vielmehr können in den erfin dungsgemäßen Haarfärbemitteln, bedingt durch die Herstellungsverfahren für die einzel nen Farbstoffe, in untergeordneten Mengen noch weitere Komponenten enthalten sein, soweit diese nicht das Färbeergebnis nachteilig beeinflussen oder aus anderen Gründen, z. B. toxikologischen, ausgeschlossen werden müssen.It is not necessary that the oxidation dye precursors or the substantive Dyes each represent uniform compounds. Rather, in the inven proper hair dyes, due to the manufacturing process for the individual colorants, other components may be contained in minor amounts, as long as these do not adversely affect the dyeing result or for other reasons, z. B. toxicological, must be excluded.
Bezüglich der in den erfindungsgemäßen Haarfärbe- und -tönungsmitteln einsetzbaren Farbstoffe wird weiterhin ausdrücklich auf die Monographie Ch. Zviak, The Science of Hair Care, Kapitel 7 (Seiten 248-250; direktziehende Farbstoffe), sowie Kapitel 8, Seiten 264-267; Oxidationsfarbstoffvorprodukte), erschienen als Band 7 der Reihe "Dermato logy" (Hrg.: Ch. Culnan und H. Maibach), Verlag Marcel Dekker Inc., New York, Basel, 1986, sowie das "Europäische Inventar der Kosmetik-Rohstoffe", herausgegeben von der Europäischen Gemeinschaft, erhältlich in Diskettenform vom Bundesverband Deutscher Industrie- und Handelsunternehmen für Arzneimittel, Reformwaren und Körperpflegemit tel e. V., Mannheim, Bezug genommen.With regard to those which can be used in the hair coloring and tinting compositions according to the invention Dyes is also expressly referred to the monograph Ch. Zviak, The Science of Hair Care, Chapter 7 (pages 248-250; substantive dyes), and Chapter 8, pages 264-267; Oxidation dye precursors), published as Volume 7 of the series "Dermato logy "(Ed .: Ch. Culnan and H. Maibach), Marcel Dekker Inc., New York, Basel, 1986, as well as the "European Inventory of Cosmetic Raw Materials" published by European Community, available in diskette form from the Bundesverband Deutscher Industrial and trading company for pharmaceuticals, health foods and personal care products tel e. V., Mannheim, referred to.
Zur Herstellung der erfindungsgemäßen Oxidationsfärbemittel werden die Oxdationsfarb stoffvorprodukte in einen geeigneten wässrigen Träger eingearbeitet. Solche Träger sind z. B. verdickte wässrige Lösungen, Cremes (Emulsionen), Gele oder tensidhaltige, schäu mende Zubereitungen, z. B. Shampoos oder Schaumaerosole oder andere Zubereitungen, die für die Anwendung auf dem Haar geeignet sind.To produce the oxidation colorants according to the invention, the oxidation color material precursors incorporated into a suitable aqueous carrier. Such carriers are z. B. thickened aqueous solutions, creams (emulsions), gels or surfactants, schäu Mende preparations, e.g. B. shampoos or foam aerosols or other preparations, which are suitable for use on the hair.
Als Trägerkomponenten werden bevorzugt
Carrier components are preferred
- - Netz- und Emulgiermittel- Wetting and emulsifying agents
- - Verdickungsmittel- thickeners
- - Reduktionsmittel (Autioxidantien)- reducing agents (auto-oxidants)
- - haarpflegende Zusätze- hair care additives
- - Duftstoffe und- Fragrances and
- - Lösungsmittel wie z. B. Wasser, Glycole oder niedere Alkohole- solvents such as B. water, glycols or lower alcohols
eingesetzt.used.
Als Netz- und Emulgiermittel eignen sich z. B. anionische, zwitterionische, ampholytische und nichtionische Tenside. Auch kationische Tenside können zur Erzielung bestimmter Effekte eingesetzt werden. Suitable wetting and emulsifying agents are, for. B. anionic, zwitterionic, ampholytic and nonionic surfactants. Cationic surfactants can also be used to achieve certain Effects are used.
Als Verdickungsmittel eignen sich einmal die wasserlöslichen hochmolekularen Polysac charid-Derivate oder Polypeptide, z. B. Cellulose- oder Stärkeether, Gelatine, Pflanzen gumme, Biopolymere (Xanthan-Gum) oder wasserlösliche synthetische Polymere wie z. B. Polyvinylpyrrolidon, Polyvinylalkohol, Polyethylenoxide, Polyacrylamide, Polyurethane, Polyacrylate und andere.The water-soluble, high-molecular Polysacs are suitable as a thickening agent charid derivatives or polypeptides, e.g. B. cellulose or starch ethers, gelatin, plants gums, biopolymers (xanthan gum) or water-soluble synthetic polymers such as. B. Polyvinylpyrrolidone, polyvinyl alcohol, polyethylene oxides, polyacrylamides, polyurethanes, Polyacrylates and others.
Zum anderen kann man tensidhaltige Zubereitungen auch durch Solubilisierung oder Emulgierung von polaren Lipiden verdicken. Solche Lipide sind z. B. Fettalkohole mit 12-18 C-Atomen, (freie) Fettsäuren mit 12-18 C-Atomen, Fettsäurepartialglyceride, Sorbitanfettsäureester, Fettsäurealkanolamide, niedrig oxethylierte Fettsäuren oder Fettal kohole, Lecithine, Sterine. Schließlich kann man gelförmige Träger auch auf Basis wässri ger Seifengele, z. B. von Ammonium-Oleat, erzeugen.On the other hand, preparations containing surfactants can also be used by solubilization or Thicken emulsification of polar lipids. Such lipids are e.g. B. fatty alcohols with 12-18 carbon atoms, (free) fatty acids with 12-18 carbon atoms, fatty acid partial glycerides, Sorbitan fatty acid esters, fatty acid alkanolamides, low ethoxylated fatty acids or fatty al alcohols, lecithins, sterols. Finally, gel-like carriers can also be based on aqueous media ger soap gels, e.g. B. of ammonium oleate.
Reduktionsmittel (Antioxidantien), die dem Träger zugesetzt werden, um eine vorzeitige oxidative Entwicklung des Farbstoffs vor der Anwendung auf dem Haar zu verhindern, sind z. B. Natriumsulfit oder Natriumascorbat.Reducing agents (antioxidants) that are added to the carrier to prevent premature to prevent oxidative development of the dye before application on the hair, are z. B. sodium sulfite or sodium ascorbate.
Haarpflegende Zusätze können z. B. Fette, Öle oder Wachse in emulgierter Form, struktur gebende Additive wie z. B. Glucose oder Pyridoxin, avivierende Komponenten wie z. B. wasserlösliche Proteine, Proteinabbauprodukte, Aminosäuren, wasserlösliche kationische Polymere, Silicone, Vitamine, Panthenol oder Pflanzenextrakte sein.Hair care additives can, for. B. fats, oils or waxes in emulsified form, structure giving additives such as B. glucose or pyridoxine, enhancing components such. B. water-soluble proteins, protein breakdown products, amino acids, water-soluble cationic Polymers, silicones, vitamins, panthenol or plant extracts.
Schließlich können Duftstoffe und Lösungsmittel wie z. B. Glycole wie 1,2- Propylenglycole, Glycerin, Glycolether wie z. B. Butylglycol, Ethyldiglycol oder niedere einwertige Alkohole wie Ethanol oder Isopropanol enthalten sein.Finally, fragrances and solvents such as. B. glycols such as 1,2- Propylene glycols, glycerin, glycol ethers such as. B. butyl glycol, ethyl diglycol or lower may contain monohydric alcohols such as ethanol or isopropanol.
Zusätzlich können noch weitere Hilfsmittel enthalten sein, die die Stabilität und Anwen dungseigenschaften der Oxidationsfärbemittel verbessern, z. B. Komplexbildner wie EDTA, NTA oder Organophosphonate, Quell- und Penetrationsmittel wie z. B. Harnstoff, Guanidin, Hydrogencarbonate, Puffersalze wie z. B. Ammoniumchlorid, Ammoniumcitrat, Ammoniumsulfat oder Alkanolammoniumsalze und gegebenenfalls Treibgase.In addition, other aids can be included that improve stability and application Improve manure properties of the oxidation colorants, e.g. B. complexing agents such as EDTA, NTA or organophosphonates, swelling and penetrating agents such. B. urea, Guanidine, hydrogen carbonates, buffer salts such as. B. ammonium chloride, ammonium citrate, Ammonium sulfate or alkanolammonium salts and optionally propellants.
Die erfindungsgemäßen Haarfärbemittel enthalten sowohl die Entwicklerkomponenten als auch die Kupplerkomponenten bevorzugt in einer Menge von 0,005 bis 20 Gew.-%, vor zugsweise 0,1 bis 5 Gew.-%, jeweils bezogen auf das gesamte Oxidationsfärbemittel. Dabei werden Entwicklerkomponenten und Kupplerkomponenten im allgemeinen in etwa äquimolaren Mengen zueinander eingesetzt. Wenn sich auch der äquimolare Einsatz als zweckmäßig erwiesen hat, so ist ein gewisser Überschuß einzelner Oxidations farbstoffvorprodukte nicht nachteilig, so daß Entwicklerkomponenten und Kupplerkompo nenten in einem Mol-Verhältnis von 1 : 0,5 bis 1 : 2 enthalten sein können.The hair colorants according to the invention contain both the developer components the coupler components are also preferably present in an amount of from 0.005 to 20% by weight preferably 0.1 to 5% by weight, based in each case on the total oxidation colorant. Included developer components and coupler components are generally about equimolar amounts used to each other. Even if the equimolar use as Has proven expedient, so is a certain excess of individual oxidation dye precursors are not disadvantageous, so that developer components and coupler components nenten in a molar ratio of 1: 0.5 to 1: 2 can be included.
Die oxidative Entwicklung der Färbung kann grundsätzlich mit Luftsauerstoff erfolgen. Bevorzugt wird jedoch ein chemisches Oxidationsmittel eingesetzt, besonders dann, wenn neben der Färbung ein Aufhelleffekt an menschlichem Haar gewünscht ist. Als Oxidations mittel kommen Persulfate, Chlorite und insbesondere Wasserstoffperoxid oder dessen An lagerungsprodukte an Harnstoff, Melamin sowie Natriumborat in Frage. Weiterhin ist es möglich, die Oxidation mit Hilfe von Enzymen durchzuführen. Dabei können die Enzyme zur Übertragung von Luftsauerstoff auf die Entwicklerkomponente oder zur Verstärkung der Wirkung geringer Mengen vorhandener Oxidationsmittel dienen. Ein Beispiel für ein enzymatisches Verfahren stellt das Vorgehen dar, die Wirkung geringer Mengen (z. B. 1% und weniger, bezogen auf das gesamte Mittel) Wasserstoffperoxid durch Peroxidasen zu verstärken.The oxidative development of the color can in principle take place with atmospheric oxygen. However, a chemical oxidizing agent is preferably used, especially when In addition to the coloring, a lightening effect on human hair is desired. As an oxidation medium come persulfates, chlorites and especially hydrogen peroxide or its type storage products of urea, melamine and sodium borate in question. Furthermore it is possible to carry out the oxidation with the help of enzymes. The enzymes for transferring atmospheric oxygen to the developer component or for amplification serve the effect of small amounts of oxidizing agents present. An example of a enzymatic process represents the procedure, the effect of small amounts (e.g. 1% and less, based on the total agent) hydrogen peroxide by peroxidases strengthen.
Zweckmäßigerweise wird die Zubereitung des Oxidationsmittels unmittelbar vor dem Haa refärben mit der Zubereitung aus den Oxidationsfarbstoffvorprodukten vermischt. Das da bei entstehende gebrauchsfertige Haarfärbepräparat sollte bevorzugt einen pH-Wert im Bereich von 6 bis 10 aufweisen. Besonders bevorzugt ist die Anwendung der Haar färbemittel in einem schwach alkalischen Milieu. Die Anwendungstemperaturen können in einem Bereich zwischen 15 und 40°C liegen. Nach einer Einwirkungszeit von ca. 30 Mi nuten wird das Haarfärbemittel durch Ausspülen von dem zu färbenden Haar entfernt. Das Nachwaschen mit einem Shampoo entfällt, wenn ein stark tensidhaltiger Träger, z. B. ein Färbeshampoo, verwendet wurde.The preparation of the oxidizing agent is expediently carried out immediately before the hair re-dye mixed with the preparation from the oxidation dye precursors. That there The resulting ready-to-use hair dye preparation should preferably have a pH value in Range from 6 to 10. The use of the hair is particularly preferred dyes in a weakly alkaline medium. The application temperatures can be in range between 15 and 40 ° C. After an exposure time of approx. 30 Wed uten the hair dye is removed from the hair to be colored by rinsing. That After washing with a shampoo is not necessary if a strong surfactant-containing carrier, z. B. a Coloring shampoo.
Die nachfolgenden Beispiele sollen den Erfindungsgegenstand näher erläutern. The following examples are intended to explain the subject matter of the invention in more detail.
2,5 g N,N'-Bis-(3'-nitrophenyl)-propylendiamin (aus 3-Nitroanilin und 1,3- Dibrompropan) wurden in 150 ml Ethanol gelöst und die Lösung mit 0,1 g Pd/C (5 Gew.-% Pd) versetzt und bei 25°C und 1 at H2-Überdruck hydriert. Nach Auf nahme der berechneten Menge H2 wurde der Ansatz vom Katalysator abgetrennt und mit verdünnter Salzsäure angesäuert. Dann wurde die Lösung zur Trockene eingeengt. Es wurden 2,0 g rötliche Kristalle erhalten.2.5 g of N, N'-bis (3'-nitrophenyl) propylenediamine (from 3-nitroaniline and 1,3-dibromopropane) were dissolved in 150 ml of ethanol and 0.1 g of Pd / C (5 Wt .-% Pd) and hydrogenated at 25 ° C and 1 atm H 2 overpressure. After taking on the calculated amount of H 2 , the batch was separated from the catalyst and acidified with dilute hydrochloric acid. Then the solution was concentrated to dryness. 2.0 g of reddish crystals were obtained.
10 g 1,4-Bis-(3'-nitrophenyl)- piperazin (Ber. (1907), 40, 5014) wurden in 90 ml Ethanol gelöst und die Lösung mit 0,2 g Pd/C (5 Gew.-% Pd) ver setzt. Die Lösung wurde bei 100°C unter einem Wasserstoffdruck von 50 bar hy driert. Nach Aufnahme der berechneten Menge an Wasserstoff wurde die Lösung mit verdünnter Salzsäure angesäuert. Dann wurde der Ansatz vom Katalysator ab getrennt (filtriert) und angesäuert. Nach dem Einengen zur Trockene wurden 8 g rosa Kristalle erhalten.10 g 1,4-bis (3'-nitrophenyl) piperazine (Ber. (1907), 40, 5014) were dissolved in 90 ml of ethanol and the solution with 0.2 g of Pd / C (5 wt .-% Pd) ver puts. The solution was at 100 ° C under a hydrogen pressure of 50 bar hy dries. After absorbing the calculated amount of hydrogen, the solution became acidified with dilute hydrochloric acid. Then the batch was removed from the catalyst separated (filtered) and acidified. After concentration to dryness, 8 g pink crystals received.
Es wurde eine Basis-Creme der folgenden Zusammensetzung hergestellt:
A base cream with the following composition was prepared:
Es wurden Färbecremes der folgenden Zusammensetzung hergestellt:
Coloring creams were made with the following composition:
Für die Ausfärbung wurden folgende Entwickler- und Kupplerkomponenten einge setzt.The following developer and coupler components were used for coloring puts.
E1: p-Toluylendiamin
E2: 2,5-Diaminophenyl-ethanol
E3: 2,4,5,6-Tetraaminopyrimidin
E4: 2,4,5-Triamino-6-hydroxypyrimidin
E5: 2,5-Diaminopyridin
E6: p-Aminophenol
E7: 3-Methyl-4-aminophenol
E8: Bis-(2-hydroxy-5-aminophenyl)-methan
E9: 1,3-N,N'-Bis-(2-hydroxyethyl)-N,N'-bis-(4'-aminophenyl)-diaminopropan-2-ol.
E10: 1,4-Bis-(4'-aminophenyl)-diazacycloheptanE1: p-tolylenediamine
E2: 2,5-diaminophenyl ethanol
E3: 2,4,5,6-tetraaminopyrimidine
E4: 2,4,5-triamino-6-hydroxypyrimidine
E5: 2,5-diaminopyridine
E6: p-aminophenol
E7: 3-methyl-4-aminophenol
E8: bis (2-hydroxy-5-aminophenyl) methane
E9: 1,3-N, N'-bis- (2-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -diaminopropan-2-ol.
E10: 1,4-bis (4'-aminophenyl) diazacycloheptane
K1: N,N'-Bis-(3'-aminophenyl)-propylendiamin (hydrochlorid), erfindungsgemäß
K2: N,N'-Bis-(3'-aminophenyl)-piperazin (hydrochlorid), erfindungsgemäß
K3: 2,4-Diaminophenoxyethanol
K4: 1,3-Bis-(2',4'-diaminophenoxy)-propanK1: N, N'-bis (3'-aminophenyl) propylenediamine (hydrochloride), according to the invention
K2: N, N'-bis- (3'-aminophenyl) -piperazine (hydrochloride), according to the invention
K3: 2,4-diaminophenoxyethanol
K4: 1,3-bis (2 ', 4'-diaminophenoxy) propane
In den Beispielen mit Entwickler- oder Kuppler-Kombinationen wurden von jedem der Entwickler oder Kuppler 3,75 mmol eingesetzt, so daß die Gesamtmenge an Entwickler bzw. Kuppler in der Färbecreme bei 7,5 m mol/100 g lag. In the examples with developer or coupler combinations of each the developer or coupler used 3.75 mmol, so that the total amount of Developer or coupler in the coloring cream was 7.5 m mol / 100 g.
Die Bestandteile wurden der Reihe nach miteinander vermischt. Nach Zugabe der Oxidationsfarbstoffvorprodukte, des Inhibitors und des (NH4)2SO4 wurde mit kon zentrierter Ammoniaklösung der pH-Wert der Emulsion auf 10 eingestellt, dann wurde mit Wasser auf 100 g aufgefüllt.The ingredients were mixed together in sequence. After the oxidation dye precursors, the inhibitor and the (NH 4 ) 2 SO 4 had been added , the pH of the emulsion was adjusted to 10 with concentrated ammonia solution, and the mixture was then made up to 100 g with water.
Die oxidative Entwicklung der Färbung wurde in einer Versuchsreihe mit Luftsau erstoff, in einer zweiten Versuchsreihe mit 1 Gew.-%-iger Wasserstoffperoxidlö sung und in einer dritten Versuchsreihe mit 9 Gew.-%-iger Wasserstoffperoxidlö sung durchgeführt.The oxidative development of the coloration was carried out in a series of experiments with Luftsau erstoff, in a second series of experiments with 1% by weight hydrogen peroxide solution solution and in a third series of experiments with 9 wt .-% - hydrogen peroxide solution solution carried out.
Hierzu wurden zu 100 g der Emulsion
To this end, 100 g of the emulsion were added
- - in der ersten Versuchsreihe mit 50 g Wasser- In the first series of experiments with 50 g of water
- - in der zweiten Versuchsreihe mit 50 g H2O2-Lösung (1%-ig) und- In the second series of experiments with 50 g of H 2 O 2 solution (1%) and
- - in der dritten Versuchsreihe mit 50 g H2O2-Lösung (9%-ig) versetzt und vermischt.- In the third series of experiments, 50 g of H 2 O 2 solution (9%) are added and mixed.
Die gebrauchsfertigen Färbeansätze wurden dann auf 5 cm lange Strähnen standar disierten, zu 80% ergrauten, aber nicht besonders vorbehandelten Menschenhaars (Kerling) aufgetragen. Nach 30 Minuten Einwirkzeit bei 32°C wurde das Haar mit Wasser gespült, mit einem üblichen Shampoo ausgewaschen, erneut gespült und getrocknet. Die Ergebnisse der Färbeversuche sind der Tabelle zu entnehmen. The ready-to-use dye batches were then standardized on 5 cm long tresses 80% gray, but not specially treated human hair (Kerling) applied. After a contact time of 30 minutes at 32 ° C, the hair was with Rinsed with water, washed out with a standard shampoo, and rinsed again dried. The results of the dyeing tests are shown in the table.
Claims (6)
in denen R1, R2, und R3 Wasserstoff, Alkylgruppen mit 1-4 C-Atomen oder Hydroxyal kylgruppen mit 2-4 C-Atomen sind und R3 auch eine Alkoxy- oder Hydroxyalkoxy gruppe mit 2-4 C-Atomen sein kann, n eine ganze Zahl von 2-8 und x = 2 oder 3 ist, und deren wasserlösliche Salze.1. N, N'-bis (3'-aminophenyl) alkylenediamines or diazacycloalkanes of the general formula I or II
in which R 1 , R 2 and R 3 are hydrogen, alkyl groups with 1-4 C atoms or Hydroxyal kyl groups with 2-4 C atoms and R 3 can also be an alkoxy or hydroxyalkoxy group with 2-4 C atoms can, n is an integer from 2-8 and x = 2 or 3, and their water-soluble salts.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000134812 DE10034812A1 (en) | 2000-07-18 | 2000-07-18 | New N,N'-bis-(3-aminophenyl)-alkylene diamines and salts are used as coupler components in oxidation colorants for keratin fibers, e.g. wool, feathers and fur, and especially human hair |
| AU2001285811A AU2001285811A1 (en) | 2000-07-18 | 2001-07-07 | Novel coupling components for oxidation colouring agents |
| EP01965086A EP1301496A2 (en) | 2000-07-18 | 2001-07-07 | Novel coupling components for oxidation colouring agents |
| PCT/EP2001/007828 WO2002006207A2 (en) | 2000-07-18 | 2001-07-07 | Novel coupling components for oxidation colouring agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000134812 DE10034812A1 (en) | 2000-07-18 | 2000-07-18 | New N,N'-bis-(3-aminophenyl)-alkylene diamines and salts are used as coupler components in oxidation colorants for keratin fibers, e.g. wool, feathers and fur, and especially human hair |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10034812A1 true DE10034812A1 (en) | 2002-01-31 |
Family
ID=7649265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2000134812 Withdrawn DE10034812A1 (en) | 2000-07-18 | 2000-07-18 | New N,N'-bis-(3-aminophenyl)-alkylene diamines and salts are used as coupler components in oxidation colorants for keratin fibers, e.g. wool, feathers and fur, and especially human hair |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1301496A2 (en) |
| AU (1) | AU2001285811A1 (en) |
| DE (1) | DE10034812A1 (en) |
| WO (1) | WO2002006207A2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7422609B2 (en) | 2005-06-29 | 2008-09-09 | Oreal | Double para-phenylenediamines joined by an aromatic group for dyeing keratin fibers |
| US7413580B2 (en) | 2005-06-29 | 2008-08-19 | L'oreal S.A. | Double para-phenylenediamines joined by a linker arm substituted with one or more carboxylic radicals and/or derivatives and use in dyeing |
| FR2887874A1 (en) * | 2005-06-29 | 2007-01-05 | Oreal | NEW DOUBLE PARA-PHENYLENEDIAMINES CONNECTED BY A BRANCHED ALIPHATIC GROUP AND USE IN COLORING |
| WO2013148805A2 (en) | 2012-03-27 | 2013-10-03 | The Procter & Gamble Company | Hair colorant compositions comprising 3- amino -2,6- dimethylphenol and 4- aminophenol-type developers, methods, and kits comprising the compositions |
| WO2013148804A2 (en) | 2012-03-27 | 2013-10-03 | The Procter & Gamble Company | Hair colorant compositions comprising amino -2,6- dimethylphenol and 1,4- phenylenediamine-type developers, methods, and kits comprising the compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2934329A1 (en) * | 1979-08-24 | 1981-03-12 | Henkel KGaA, 4000 Düsseldorf | Oxidn. hair-dye compsns. - contg. bis:4-methoxy-5-aminophenyl-alkylene di:amine or salt deriv. as coupling component |
| EP0917531B1 (en) * | 1996-07-03 | 2002-01-09 | Hans Schwarzkopf GmbH & Co. KG | Piperazine derivatives and oxydation dyes |
-
2000
- 2000-07-18 DE DE2000134812 patent/DE10034812A1/en not_active Withdrawn
-
2001
- 2001-07-07 EP EP01965086A patent/EP1301496A2/en not_active Withdrawn
- 2001-07-07 AU AU2001285811A patent/AU2001285811A1/en not_active Abandoned
- 2001-07-07 WO PCT/EP2001/007828 patent/WO2002006207A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002006207A2 (en) | 2002-01-24 |
| AU2001285811A1 (en) | 2002-01-30 |
| WO2002006207A3 (en) | 2002-04-18 |
| EP1301496A2 (en) | 2003-04-16 |
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