DE4205329A1 - P-PHENYLENDIAMINE DERIVATIVES AS OXIDATING PREPARED PRODUCTS - Google Patents
P-PHENYLENDIAMINE DERIVATIVES AS OXIDATING PREPARED PRODUCTSInfo
- Publication number
- DE4205329A1 DE4205329A1 DE19924205329 DE4205329A DE4205329A1 DE 4205329 A1 DE4205329 A1 DE 4205329A1 DE 19924205329 DE19924205329 DE 19924205329 DE 4205329 A DE4205329 A DE 4205329A DE 4205329 A1 DE4205329 A1 DE 4205329A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- salts
- hair
- atom
- methyl
- 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- Withdrawn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
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 title description 2
- 230000003647 oxidation Effects 0.000 claims abstract description 22
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 22
- 239000000975 dye Substances 0.000 claims abstract description 19
- 239000000118 hair dye Substances 0.000 claims abstract description 19
- 150000004989 p-phenylenediamines Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 239000002243 precursor Substances 0.000 claims description 18
- 238000004043 dyeing Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052801 chlorine Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- KOHBEDRJXKOYHL-UHFFFAOYSA-N 2-methoxy-n-methylethanamine Chemical compound CNCCOC KOHBEDRJXKOYHL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003581 cosmetic carrier Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- -1 heterocyclic hydrazone derivatives Chemical class 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000007800 oxidant agent Substances 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- NXQAGUOCSMBQRH-UHFFFAOYSA-N 2-chloro-1-n-(2-methoxyethyl)-1-n-methylbenzene-1,4-diamine Chemical compound COCCN(C)C1=CC=C(N)C=C1Cl NXQAGUOCSMBQRH-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
- 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 2
- JDTNQUFJDMXMMY-UHFFFAOYSA-N 4-n-(2-methoxyethyl)-4-n-methylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.COCCN(C)C1=CC=C(N)C=C1 JDTNQUFJDMXMMY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000037308 hair color Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- CRRPJMGQJLYCIU-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)-n-methyl-4-nitroaniline Chemical compound COCCN(C)C1=CC=C([N+]([O-])=O)C=C1Cl CRRPJMGQJLYCIU-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
- JLULDHAWXYOPSJ-UHFFFAOYSA-N 2-fluoro-n-(2-methoxyethyl)-n-methyl-4-nitroaniline Chemical compound COCCN(C)C1=CC=C([N+]([O-])=O)C=C1F JLULDHAWXYOPSJ-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 description 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
- WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- FVFJGQJXAWCHIE-UHFFFAOYSA-N [4-(bromomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CBr)C=C1 FVFJGQJXAWCHIE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229960002163 hydrogen peroxide Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FYTRVVJHEWUARG-UHFFFAOYSA-N n-(2-aminophenyl)nitramide Chemical class NC1=CC=CC=C1N[N+]([O-])=O FYTRVVJHEWUARG-UHFFFAOYSA-N 0.000 description 1
- DKCCZJWXODOUCH-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methyl-4-nitroaniline Chemical compound COCCN(C)C1=CC=C([N+]([O-])=O)C=C1 DKCCZJWXODOUCH-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
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Abstract
Description
Die Erfindung betrifft die Verwendung von p-Phenylendiaminderivaten als Oxidationsfarbstoffvorprodukte, insbesondere als Entwicklerkomponenten in Oxidationsfärbemitteln für Keratinfasern.The invention relates to the use of p-phenylenediamine derivatives as Oxidation dye precursors, especially as developer components in Oxidation dyes for keratin fibers.
Für das Färben von Keratinfasern, insbesondere von Haaren, Pelzen und Fel len spielen die sogenannten Oxidationshaarfärbemittel wegen ihren inten siven Farben und guten Echtheitseigenschaften eine bevorzugte Rolle. Sol che Haarfärbemittel enthalten Oxidationsfarbstoffvorprodukte in einem wäß rigen Träger. Als Oxidationsfarbstoffvorprodukte werden Entwicklersubstan zen und Kupplersubstanzen eingesetzt. Die Entwicklerkomponenten bilden unter dem Einfluß von Oxidationsmitteln oder von Luftsauerstoff unterein ander oder unter Kupplung mit einer oder mehreren Kupplerkomponenten die eigentlichen Farbstoffe aus.For dyeing keratin fibers, especially hair, fur and fel len play the so-called Oxidationshaarfärbemittel because of their inten intense colors and good fastness properties a preferred role. Sol che hair colorants contain oxidation dye precursors in an aqueous ry carrier. As oxidation dye precursors are developing sub zen and couplers used. Form the developer components under the influence of oxidizing agents or atmospheric oxygen other or under coupling with one or more coupler components the actual dyes from.
Als Entwicklersubstanzen werden üblicherweise primäre aromatische Amine mit einer weiteren in Para- oder Orthoposition befindlichen freien oder substituierten Hydroxy- oder Aminogruppe, ferner Diaminopyridinderivate, heterocyclische Hydrazonderivate und 4-Aminopyrazolonderivate eingesetzt. Als sogenannte Kupplersubstanzen werden Metaphenylendiaminderivate, Dihydroxynaphthaline, Naphthole, Resorcinderivate, meta-Aminophenole und Pyrazolone verwendet.As developer substances are usually primary aromatic amines with another located in para or ortho position free or substituted hydroxy or amino group, furthermore diaminopyridine derivatives, heterocyclic hydrazone derivatives and 4-aminopyrazolone derivatives used. As so-called coupler substances Metaphenylendiaminderivate, Dihydroxynaphthalenes, naphthols, resorcinol derivatives, meta-aminophenols and Pyrazolone used.
Eine bestimmte Entwicklersubstanz kann durch Kombination mit unterschied lichen Kupplern sehr unterschiedliche Farbnuancen bilden, trotzdem gelingt es oft nicht, mit Hilfe einer einzigen Entwicklersubstanz zu der Vielzahl natürlicher Haarfarbnuancen zu kommen. In der Praxis ist daher meist eine Kombination verschiedener Entwicklerkomponenten und Kupplerkomponenten erforderlich, um eine einzige natürlich wirkende Haarfärbung zu erhalten. Daher besteht ständig Bedarf an neuen Entwicklerkomponenten. A certain developer substance can be distinguished by combination with union couplers form very different shades, still succeed Often it does not, with the help of a single developer substance to the multiplicity natural hair shades to come. In practice, therefore, is usually one Combination of different developer components and coupler components required to obtain a single natural hair coloring. Therefore, there is a constant need for new developer components.
Gute Oxidationsfarbstoffvorprodukte müssen in erster Linie folgende Vor aussetzungen erfüllen:Good oxidation dye precursors must first and foremost following fulfill the requirements:
Sie müssen bei der oxidativen Kupplung die gewünschten Farbnuancen in aus reichender Intensität und Echtheit ausbilden. Bei ihrer Anwendung in Haar färbemitteln sollen sie bereits bei niedrigen Temperaturen unterhalb 40 °C ein gutes Aufziehvermögen auf menschlichem Haar besitzen, wobei keine merk lichen Unterschiede zwischen strapaziertem und frisch nachgewachsenen Haar bestehen dürfen, und sie sollen beständig sein gegen Licht, Wärme und den Einfluß chemischer Reduktionsmittel z. B. gegen Dauerwellflüssigkeiten; schließlich sollen sie die Kopfhaut nicht zu sehr anfärben und vor allem sollen sie in toxikologischer und dermatologischer Hinsicht unbedenklich sein.You have in the oxidative coupling the desired color shades in train reaching intensity and authenticity. When applied in hair Dyes should already at low temperatures below 40 ° C. have a good absorption on human hair, with no noticeable differences between strained and newly regrown hair and they should be resistant to light, heat and the Influence of chemical reducing agents z. B. against perming fluids; after all, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view his.
p-Phenylendiamin und Derivate dieser Verbindung sind zwar als Oxidationsfarbstoffvorprodukte seit langem bekannt. Viele dieser Verbin dungen sind jedoch toxikologisch und dermatologisch bedenklich, da sie allergisierende Eigenschaften aufweisen. Es besteht daher ein hohes In teresse an Oxidationsfarbstoffvorprodukten, die einerseits intensive Far ben mit hohen Echtheitseigenschaften ausbilden, andererseits aber in to xikologischer und dermatologischer Hinsicht unbedenklich sind.Although p-phenylenediamine and derivatives of this compound are known as Oxidation dye precursors have long been known. Many of these verbin however, toxicological and dermatological have allergenic properties. There is therefore a high In interest in oxidation dye precursors, on the one hand intense Far training with high fastness properties, but on the other hand in to xikologischer and dermatological regard are harmless.
Die deutsche Auslegeschrift DE 27 37 291 beschreibt N-(2-Alkoxyalkyl)-p-phenylendiaminderivate, wobei Alkoxy entweder Methoxy oder Ethoxy und Alkyl entweder Ethyl oder Propyl darstellen, als Entwick lerkomponenten in Oxidationshaarfärbemitteln.German Auslegeschrift DE 27 37 291 describes N- (2-alkoxyalkyl) -p-phenylenediamine derivatives wherein alkoxy is either methoxy or ethoxy and alkyl are either ethyl or propyl, as a developer lerkomponenten in Oxidationshaarfärbemitteln.
Auch in der US-Patentschrift 38 84 627 sind Oxidationsfärbemittel mit substituierten p-Phenylendiaminen beschrieben. Die Druckschrift beschreibt neben p-Phenylendiaminen mit tertiärer Aminogruppe und nicht substitu iertem Benzolkern auch p-Phenylendiamine mit sekundärer Aminogruppe, deren Benzolkern obligatorisch mindestens einen Substituenten aufweist. Diese Verbindungstypen sind jedoch entweder mit Nachteilen hinsichtlich der Hautverträglichkeit behaftet oder sie sind zur Erzielung tieferer Haar färbungen weniger geeignet. Also in US Patent 38 84 627 are oxidation with Substituted p-phenylenediamines described. The document describes in addition to p-phenylenediamines having a tertiary amino group and not substituted ierten Benzolkern also p-phenylenediamines with secondary amino group, whose Benzene core compulsorily having at least one substituent. These However, connection types are either disadvantageous in terms of Skin irritability or they are to achieve deeper hair dyeings less suitable.
Es wurde nun gefunden, daß durch die Verwendung von p-Phenylendiaminderi vaten der Formel I als Entwicklerkomponente in Oxidationshaarfärbemitteln Haarfärbungen hinsichtlich Lichtechtheit, Wärmestabilität, Kaltwellecht heit und Egalisiervermögen deutlich verbessert werden können.It has now been found that by the use of p-Phenylendiaminderi of the formula I as a developer component in Oxidationshaarfärbemitteln Hair dyeing with regard to light fastness, thermal stability, cold wave fastness and leveling ability can be significantly improved.
Gegenstand der Erfindung ist die Verwendung von p-Phenylendiaminderivaten der Formel IThe invention relates to the use of p-phenylenediamine derivatives the formula I
in der R1 und R2 unabhängig voneinander Alkylgruppen mit 1 bis 4 C-Atomen darstellen, X ein Wasserstoffatom oder ein Halogenatom ist und n eine gan ze Zahl zwischen 2 und 4 ist, oder deren Salzen als Vorprodukt zur Erzeu gung von Oxidationsfärbungen.in which R 1 and R 2 independently represent alkyl groups having 1 to 4 carbon atoms, X is a hydrogen atom or a halogen atom and n is a gan number between 2 and 4, or their salts as a precursor for the generation of Oxidationsfärbungen.
Ein besonders günstiges Färbeverhalten zeigen die Verbindungen der Formel I oder deren Salze, in denen R1 und R2 Methylgruppen sind und n gleich 2 ist. Die Verwendung dieser Verbindungen oder deren Salze als Vorprodukte zur Erzeugung von Oxidationsfärbungen ist daher ein weiterer Erfindungs gegenstand.A particularly favorable dyeing behavior show the compounds of formula I or their salts, in which R 1 and R 2 are methyl groups and n is 2. The use of these compounds or their salts as precursors for the production of oxidation dyeings is therefore a further subject of the invention.
Die p-Phenylendiaminderivate der Formel I sind Oxidationsfarbstoffvorpro dukte vom Typ der Entwicklersubstanzen, d. h. sie vermögen unter der Ein wirkung von Oxidationsmitteln Farbstoffe auszubilden. In Gegenwart von Kupplersubstanzen werden jedoch besonders brillante und intensive Farben gebildet. Als Kupplersubstanzen eignen sich vor allem Verbindungen wie z. B. α-Naphthol, Ortho-kresol, Meta-kresol, 2,6-Dimethylphenol, 2,5-Dimethyl phenol, Brenzcatechin, Pyrogallol, 1,5- bzw. 1,7-Dihydroxynaphthalin, 5-Ami no-2-methylphenol, Meta-aminophenol, 2,4-Diaminoanisol, Meta-toluylendia min, Resorcin, Resorcinmonomethylether, Meta-phenylendiamin, 1-Phenyl-3- methyl-pyrazolon-5, 1-Amino-3-nitrobenzol, 2,4-Dichlor-3-aminophenol, 1,3- Bis-(2,4-diaminophenoxy)-propan, 2-Chlorresorcin, 2-Chlor-6-methyl-3-amino phenol, 2,7-Dihydroxynaphthalin, 2-Methylresorcin, 2,4-Diaminophenol.The p-phenylenediamine derivatives of the formula I are Oxidationsfarbstoffvorpro Products of the type of developer substances, d. H. they can do under the one effect of oxidizing agents to form dyes. In the presence of Coupler substances, however, become particularly brilliant and intense colors educated. As couplers are especially compounds such. B. α-naphthol, ortho-cresol, meta-cresol, 2,6-dimethylphenol, 2,5-dimethyl phenol, catechol, pyrogallol, 1,5- or 1,7-dihydroxynaphthalene, 5-Ami no-2-methylphenol, meta-aminophenol, 2,4-diaminoanisole, meta-toluylenedia min, resorcinol, resorcinol monomethyl ether, meta-phenylenediamine, 1-phenyl-3- methyl-pyrazolone-5, 1-amino-3-nitrobenzene, 2,4-dichloro-3-aminophenol, 1,3- Bis- (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 2-chloro-6-methyl-3-amino phenol, 2,7-dihydroxynaphthalene, 2-methylresorcinol, 2,4-diaminophenol.
Mit diesen und anderen bekannten Kupplersubstanzen bilden die p-Phenylen diaminderivate der Formel I ein breites Spektrum von Farbnuancen, von denen besonders diejenigen, die im Rubin- bis Blau-Bereich liegen, aufgrund ihrer guten Echtheitseigenschaften hervorzuheben sind. Die erfindungsge mäßen p-Phenylendiaminderivate der Formel I eignen sich daher hervorragend zur Verwendung als Oxidationsfarbstoffvorprodukte vom Entwicklertyp in Haarfärbemitteln.With these and other known coupler substances form the p-phenylene diamine derivatives of the formula I a wide range of color shades, of which especially those in the ruby to blue range due to Their good fastness properties are to be emphasized. The erfindungsge Mäß p-phenylenediamine derivatives of the formula I are therefore ideal for use as developer type oxidation dye precursors Hair dyes.
Die p-Phenylendiaminderivate der Formel I können entweder als solche oder in Form ihrer wasserlöslichen Salze mit anorganischen oder organischen Säuren, z. B. als Hydrochloride, Sulfate, Phosphate, Acetate, Propionate, Lactate oder Citrate eingesetzt werden.The p-phenylenediamine derivatives of the formula I can be used either as such or in the form of their water-soluble salts with inorganic or organic Acids, e.g. As hydrochlorides, sulfates, phosphates, acetates, propionates, Lactates or citrates are used.
Die meisten Verbindungen der Formel I sind bereits bekannt, diejenigen Verbindungen der allgemeinen Formel I, in denen R1 und R2 Methylgruppen sind, n gleich 2 ist und X ein Fluoratom oder ein Chloratom darstellt, und deren Salze sind neu; sie sind daher selbst Gegenstand der vorliegenden Erfindung.Most compounds of the formula I are already known, those compounds of the general formula I in which R 1 and R 2 are methyl groups, n is 2 and X represents a fluorine atom or a chlorine atom, and their salts are new; They are therefore themselves the subject of the present invention.
Auch das Verfahren zu ihrer Herstellung ist ein Gegenstand der Erfindung. Man setzt dazu nach an sich literaturbekannten Syntheseverfahren Methyl-2- methoxyethylamin (CH3-NH-(CH2)2-OCH3) mit einem Nitrobenzolderivat der Formel II um, wobei Y ein Fluoratom darstellt, wenn X ein Wasserstoff- oder ein Fluoratom ist und Y ein Chloratom darstellt, wenn X ein Chloratom ist, und überführt dann in dem Reaktionsprodukt der Formel III die Nitro gruppe durch katalytische Hydrierung in die Aminogruppe.The process for their preparation is also an object of the invention. This is done according to the literature-known synthesis method methyl-2-methoxyethylamine (CH 3 -NH- (CH 2 ) 2 -OCH 3 ) with a nitrobenzene derivative of the formula II, wherein Y represents a fluorine atom, when X is a hydrogen or a fluorine atom and Y represents a chlorine atom when X is a chlorine atom, and then converted in the reaction product of formula III, the nitro group by catalytic hydrogenation in the amino group.
Ein weiterer Gegenstand der Erfindung sind Haarfärbemittel mit einem Ge halt an Oxidationfarbstoffvorprodukten in einem kosmetischen Träger, die als Oxidationsfarbstoffvorprodukte p-Phenylendiaminderivate der Formel I, wobei R1 und R2 unabhängig voneinander Alkylgruppen mit 1-4 C-Atomen darstellen, X ein Wasserstoffatom oder ein Halogenatom ist und n eine ganze Zahl von 2 bis 4 ist, oder deren Salze als Entwicklerkomponente in einer Menge von 0,05 bis 10 mMol pro 100 g des Haarfärbemittels und gege benenfalls übliche Kupplerkomponenten enthalten.Another object of the invention are hair dyes with a content of Ge oxidation dye precursors in a cosmetic carrier, the oxidation dye precursors p-phenylenediamine derivatives of the formula I, wherein R 1 and R 2 independently represent alkyl groups having 1-4 carbon atoms, X is a hydrogen atom or is a halogen atom and n is an integer of 2 to 4, or their salts as a developer component in an amount of 0.05 to 10 mmol per 100 g of the hair dye and optionally contain conventional coupler components.
In den erfindungsgemäßen Haarfärbemitteln werden die Entwicklerstubstanzen und die Kupplersubstanzen im allgemeinen in äquimolaren Mengen eingesetzt, ein gewisser Überschuß einzelner Oxidationsfarbstoffvorprodukte ist je doch nicht nachteilig, so daß Entwicklersubstanzen und Kupplersubstanzen in einem Molverhältnis von 1 : 0,5 bis 1 : 2 eingesetzt werden können.In the hair colorants according to the invention, the developer substances become and the coupler substances are generally used in equimolar amounts, a certain excess of individual oxidation dye precursors is ever but not disadvantageous, so that developers and couplers in a molar ratio of 1: 0.5 to 1: 2 can be used.
Es ist aber nicht erforderlich, daß die Verbindung der Formel I einheit liche Verbindungen sind. Vielmehr können auch Gemische von Verbindungen der Formel I oder auch Gemische von Verbindungen der Formel I mit üblichen Entwicklersubstanzen zum Einsatz kommen.However, it is not necessary that the compound of formula I unit are connections. Rather, mixtures of compounds of formula I or mixtures of compounds of formula I with conventional Developers are used.
Zur Modifikation der Haaranfärbung können den erfindungsgemäßen Haarfär bemitteln auch bekannte direktziehende Haarfarbstoffe z. B. Nitrophenylendiaminderivat, Antrachinonfarbstoffe oder Indophenole zuge setzt werden.For the modification of hair coloring the hair dye according to the invention averaging also known direct hair dyes z. B. Nitrophenylenediamine derivative, anthraquinone dyes or indophenols be set.
Zur Herstellung der erfindungsgemäßen Haarfärbemittel werden die Oxidationsfarbstoffvorprodukte und gegebenenfalls direktziehende Haar farbstoffe in einen wäßrigen kosmetischen Träger eingearbeitet. Solche Träger sind z. B. Cremes, Emulsionen, Gele oder auch tensidhaltige schäu mende Lösungen z. B. Shampoos oder andere Zubereitungen, die für die An wendung auf dem Haar geeignet sind.For the preparation of the hair dye according to the invention are Oxidation dye precursors and optionally direct hair dyes incorporated in an aqueous cosmetic carrier. Such Carriers are z. As creams, emulsions, gels or surfactant-containing future solutions z. As shampoos or other preparations for the An are suitable for the hair.
Übliche Bestandteile solcher kosmetischer Zubereitungen sind z. B. Netz- und Emulgiermittel wie anionische, nichtionische oder ampholytische Tenside, z. B. Fettalkoholsulfate, Alkansulfonate, α-Olephinsulfonate, Fettalkoholpolyglycolethersulfate, Ethylenoxidanlagerungsprodukte an Fettalkohole, Fettsäuren und Alkylphenole, Sorbitanfettsäureester und Fettsäurepartialglyceride, Fettsäurealkanolamide sowie Verdickungsmittel, wie z. B. Methyl- oder Hydroxyethylcellulose, Stärke, Fettalkohole, Par affinöle, Fettsäuren, ferner Parfumöle und haarpflegende Zusätze, wie z. B. wasserlösliche kationische Polymere, Proteinderivate, Pantothensäure und Cholesterin.Usual components of such cosmetic preparations are, for. Eg network and emulsifiers such as anionic, nonionic or ampholytic Surfactants, e.g. Fatty alcohol sulfates, alkanesulfonates, α-olefinsulfonates, Fatty alcohol polyglycol ether sulfates, ethylene oxide addition products Fatty alcohols, fatty acids and alkylphenols, sorbitan fatty acid esters and Fatty acid partial glycerides, fatty acid alkanolamides and thickening agents, such as For example, methyl or hydroxyethyl cellulose, starch, fatty alcohols, par affine oils, fatty acids, perfume oils and hair care additives, such as. B. water-soluble cationic polymers, protein derivatives, pantothenic acid and cholesterol.
Die Bestandteile der kosmetischen Träger werden zur Herstellung der erfindungsgemäßen Haarfärbemittel in für diesen Zweck üblichen Mengen eingesetzt; z. B. werden Emulgiermittel in Konzentrationen von 0,5 bis 30 Gew.-% und Verdickungsmittel in Konzentrationen von 0,1 bis 25 Gew.-% des gesamten Färbemittels eingesetzt.The ingredients of the cosmetic carriers are used to prepare the Hair colorants according to the invention in amounts customary for this purpose used; z. B. become emulsifiers in concentrations of 0.5 to 30 Wt .-% and thickener in concentrations of 0.1 to 25 wt .-% of entire colorant used.
Besonders geeignet als Träger ist ein Gel mit einem Gehalt von 1 bis 20 Gew.-% einer Seife, bevorzugt Ammoniumoleat, oder eine Öl-in-Wasser- Emulsion mit einem Gehalt von 1 bis 25 Gew.-% einer Fettkomponente mit 0,5 bis 30 Gew.-% eines Emulgiermittels aus der Gruppe der anionischen, nichtionischen, ampholytischen oder zwitterionischen Tenside.Particularly suitable as a carrier is a gel with a content of 1 to 20 % By weight of a soap, preferably ammonium oleate, or an oil-in-water Emulsion containing 1 to 25% by weight of a 0.5% fat component to 30% by weight of an emulsifier from the group of anionic, nonionic, ampholytic or zwitterionic surfactants.
Die Oxidationsfarbstoffvorprodukte werden in Mengen von 0,2 bis 5 Gew.-%, vorzugsweise 1 bis 3 Gew.-%, des gesamten Färbemittels in den Träger ein gemischt.The oxidation dye precursors are in amounts of from 0.2 to 5 wt .-%, preferably 1 to 3% by weight of the total colorant in the carrier mixed.
Die oxidative Entwicklung der Färbung kann grundsätzlich mit Luftsauer stoff erfolgen, bevorzugt wird jedoch ein chemisches Oxidationsmittel eingesetzt, besonders dann, wenn neben der Färbung ein aufhellender Effekt am Haar gewünscht wird. Als Oxidationsmittel kommen insbesondere Wasser stoffperoxid oder dessen Anlagerungsprodukte an Harnstoff, Melamin oder Natriumborat, sowie Gemische aus derartigen Wasserstoffperoxidanlagerungsprodukten mit Kaliumperoxiddisulfat in Be tracht.The oxidative development of staining can basically be done with air-acid fabric, but preferred is a chemical oxidant used, especially if in addition to the coloring a whitening effect is desired on the hair. The oxidizing agents are in particular water peroxide or its addition products of urea, melamine or Sodium borate, as well as mixtures of such Hydrogen peroxide addition products with potassium peroxide disulfate in Be costume.
Bevorzugt wird eine Zubereitung des Oxidationsmittels unmittelbar vor dem Haarefärben mit der Zubereitung aus Oxidationsfarbstoffvorprodukten und Träger vermischt. Das dabei entstehende gebrauchsfertige Haarfärbepräparat sollte bevorzugt einen pH-Wert im Bereich von 6 bis 10 aufweisen.Preference is given to a preparation of the oxidizing agent immediately before Hair dyeing with the preparation of oxidation dye precursors and Carrier mixed. The resulting ready-to-use hair dye preparation should preferably have a pH in the range of 6 to 10.
Besonders bevorzugt ist die Anwendung des Haarfärbemittels in einem schwach alkalischen Milieu, die Anwendungstemperaturen können in einem Bereich zwischen 15 und 40°C liegen. Nach einer Einwirkungszeit von ca. 30 Minuten 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.Particularly preferred is the application of the hair dye in one weak alkaline environment, the application temperatures can be in one Range between 15 and 40 ° C. After an exposure time of approx. For 30 minutes, the hair dye by rinsing of the to be dyed Hair removed. The washing with a shampoo is eliminated if a strong surfactant-containing carrier, for. As a dyeing shampoo was used.
Die nachfolgenden Beispiele sollen den Erfindungsgegenstand näher erläu tern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to explain the subject matter of the invention in more detail but without limiting it to it.
Eine Mischung bestehend aus 7 g (0,05 Mol 4-Fluornitroben zol), 3,8 g (0,028 Mol) Caliumcarbonat und 4,46 g (0,05 Mol) Me thyl-2-methoxyethylamin in 80 ml Aceton wurde für vier Stun den unter Rückfluß gekocht. Nach dem Abkühlen und Abfiltrie ren des Niederschlags wurde zur Trockene eingeengt, das Öl wurde ohne Reinigung weiter verwendet.A mixture consisting of 7 g (0.05 mol 4-Fluornitroben zol) 3.8 g (0.028 mol) of potassium carbonate and 4.46 g (0.05 mol) of Me Thyl-2-methoxyethylamine in 80 ml of acetone was used for four hours cooked under reflux. After cooling and filtration The precipitate was concentrated to dryness, the oil was used without purification.
Das Öl aus Stufe 1 wurde in 200 ml Ethanol aufgenommen und in Gegenwart von ca. 0,5 g Pa/C bei ca. 20°C und 1 bar hydriert.The oil from step 1 was taken up in 200 ml of ethanol and poured into Presence of about 0.5 g Pa / C at about 20 ° C and 1 bar hydrogenated.
Nach beendeter H2-Aufnahme wurde vom Katalysator abfiltriert. Nach dem Ansäuern mit Salzsäure wurde zur Trockene eingeengt.After completion of the H 2 uptake, the catalyst was filtered off. After acidification with hydrochloric acid was evaporated to dryness.
Farblose Kristalle, Schmelzpunkt: ab 178°C Zersetzung.Colorless crystals, melting point: from 178 ° C decomposition.
9,6 g (0,05 Mol) 3,4-Dichlornitrobenzol und 8,9 g (0,1 Mol) Methyl-2-methoxyethylamin wurden sieben Stunden bei 120°C ge rührt. Nach dem Abkühlen wurden 100 ml einer H2O/HCl-Mischung hinzugegeben und 5 mal mit je 50 ml Ether extrahiert. Nach Ent fernen des Lösungsmittels verblieb ein Öl, das sogleich weiter verwendet wurde. 9.6 g (0.05 mol) of 3,4-dichloronitrobenzene and 8.9 g (0.1 mol) of methyl-2-methoxyethylamine were stirred for seven hours at 120 ° C ge. After cooling, 100 ml of a H 2 O / HCl mixture were added and extracted 5 times with 50 ml of ether. After removing the solvent, an oil remained and was immediately used.
Analog Beispiel 1, Stufe 2.Analogously to Example 1, stage 2.
Beige Kristalle, Schmelzpunkt: ab 150°C Zersetzung.Beige crystals, melting point: from 150 ° C decomposition.
8,0 g (0,05 Mol) 3,4 Difluornitrobenzol und 8,9 g (0,1 Mol) Methyl-2-methoxyethylamin wurden sieben Stunden bei 120°C ge rührt. Nach dem Abkühlen wurden 100 ml einer H2O/HCl-Mischung hinzugegeben und 5 mal mit je 50 ml Ether extrahiert. Nach dem Entfernen des Lösungsmittels verblieben gelbe Kristalle, Schmelzpunkt: 62 bis 63°C.8.0 g (0.05 mol) of 3,4-difluoronitrobenzene and 8.9 g (0.1 mol) of methyl 2-methoxyethylamine were stirred for seven hours at 120 ° C ge. After cooling, 100 ml of a H 2 O / HCl mixture were added and extracted 5 times with 50 ml of ether. After removal of the solvent left yellow crystals, melting point: 62 to 63 ° C.
Analog Beispiel 1, Stufe 2.Analogously to Example 1, stage 2.
Beige Kristalle, sehr hygroskopisch.Beige crystals, very hygroscopic.
Es wurden erfindungsgemäße Haarfärbemittel in Form einer Haarfärbecreme- Emulsion der folgenden Zusammensetzung hergestellt:Hair colorants according to the invention in the form of a hair dye cream Emulsion of the following composition:
Die Bestandteile wurden der Reihe nach miteinander vermischt, nach Zugabe der Entwicklerkomponenten und des Inhibitors wurde zunächst die konzen trierte Ammoniaklösung der pH-Wert der Emulsion auf 9,5 eingestellt, dann wurde mit Wasser auf 100 g aufgefüllt.The ingredients were mixed together in order, after addition the developer components and the inhibitor was initially the concentrated trated ammonia solution adjusted the pH of the emulsion to 9.5, then was made up to 100 g with water.
Die oxidative Entwicklung der Färbung wurde mit 3 %iger Wasserstoffper oxidlösung als Oxidationslösung durchgeführt. Hierzu wurden 100 g der Emulsion mit 50 g Wasserstoffperoxidlösung (3 %ig) versetzt und vermischt.The oxidative development of the dyeing was carried out with 3% hydrogen per oxide solution carried out as an oxidation solution. For this purpose, 100 g of Emulsion with 50 g of hydrogen peroxide solution (3%) and mixed.
Die Färbecreme wurde auf ca. 5 cm lange Strähnen standardisierten, zu 90 ergrauten, aber nicht besonders vorbehandelten Menschenhaars aufgetragen und dort 30 Minuten bei 27°C belassen. Nach Beendigung des Färbeprozesses wurde das Haar gespült, mit einem üblichen Haarwaschmittel gewaschen und anschließend getrocknet.The staining cream was standardized to about 5 cm long strands, to 90 graying, but not particularly pre-treated human hair applied and leave it at 27 ° C for 30 minutes. After completion of the dyeing process The hair was rinsed, washed with a usual shampoo and then dried.
Als Entwicklerkomponenten wurden die erfindungsgemäßen Entwicklerkompo nenten E1 bis E3 eingesetzt.As developer components, the developer compo used E1 to E3.
Als Kupplerkomponenten wurden die folgenden Verbindungen verwendet:As coupler components, the following compounds were used:
Die erzielten Farbnuancen sind Tabelle 1 zu entnehmen.The shades obtained are shown in Table 1.
Claims (5)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19924205329 DE4205329A1 (en) | 1992-02-21 | 1992-02-21 | P-PHENYLENDIAMINE DERIVATIVES AS OXIDATING PREPARED PRODUCTS |
| PCT/EP1993/000351 WO1993016679A1 (en) | 1992-02-21 | 1993-02-13 | p-PHENYLENE DIAMINE DERIVATIVES AS INITIAL PRODUCTS FOR OXIDATION DYES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19924205329 DE4205329A1 (en) | 1992-02-21 | 1992-02-21 | P-PHENYLENDIAMINE DERIVATIVES AS OXIDATING PREPARED PRODUCTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4205329A1 true DE4205329A1 (en) | 1993-08-26 |
Family
ID=6452276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19924205329 Withdrawn DE4205329A1 (en) | 1992-02-21 | 1992-02-21 | P-PHENYLENDIAMINE DERIVATIVES AS OXIDATING PREPARED PRODUCTS |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE4205329A1 (en) |
| WO (1) | WO1993016679A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015766A1 (en) * | 1994-11-17 | 1996-05-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation dyes |
| FR2767687A1 (en) * | 1997-09-01 | 1999-03-05 | Oreal | COMPOSITION FOR KERATIN FIBER OXIDATION STAIN COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL, OXIDATION BASE AND ADDITIONAL COUPLER, AND DYEING PROCESS |
| FR2767686A1 (en) * | 1997-09-01 | 1999-03-05 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL AND TWO OXIDATION BASES, AND DYEING METHOD |
| WO2000021496A1 (en) * | 1998-10-13 | 2000-04-20 | Wella Aktiengesellschaft | Agent and method for dyeing fibres |
| US6277156B1 (en) | 1997-09-01 | 2001-08-21 | L'ORéAL S.A. | Oxidation dyeing composition for keratin fibres comprising 2-chloro-6-methyl-3-aminophenol and an oxidation base, and dyeing method |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005000795A2 (en) * | 2003-06-10 | 2005-01-06 | Smithkline Beecham Corporation | Aniline derivatived androgen-, glucocorticoid-, mineralcorticoid- and progesterone- receptor modulators |
| EP3727599B8 (en) | 2017-12-21 | 2023-11-22 | Laboratoire Biosthetique Kosmetik GmbH & Co. KG | Composition for dyeing keratin fibers containing a combination of a p-phenylene derivative and 2,7-naphthalenediol and use thereof for reducing a yellow tinge in a hairstyle |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE786710A (en) * | 1971-10-04 | 1973-01-25 | Bristol Myers Co | COMPOSITION FOR HAIR DYE WITH |
| US3970423A (en) * | 1971-10-04 | 1976-07-20 | Clairol Incorporated | Oxidative hair dye compositions |
| CA1025881A (en) * | 1973-10-15 | 1978-02-07 | Alexander Halasz | Dyeing keratin fibers with 2-substituted m-toluenediamines |
| US4113491A (en) * | 1975-02-10 | 1978-09-12 | Konishiroku Photo Industry Co., Ltd. | Color photographic developing composition |
| FR2362112A1 (en) * | 1976-08-20 | 1978-03-17 | Oreal | NEW PARAPHENYLENEDIAMINES AND TINCTORIAL COMPOSITIONS FOR KERATINIC FIBERS CONTAINING THEM |
| DE2830497B1 (en) * | 1978-07-12 | 1980-01-17 | Schwarzkopf Gmbh Hans | Process for dyeing human hair and means for carrying it out |
| DE3149458A1 (en) * | 1981-12-14 | 1983-06-23 | Henkel KGaA, 4000 Düsseldorf | NEW P-PHENYLENE DIAMINE, THEIR PRODUCTION AND USE |
| LU87128A1 (en) * | 1988-02-08 | 1989-09-20 | Oreal | KERATINIC FIBER DYEING COMPOSITION USING 5,6-DIHYDROXYINDOLE AND AT LEAST ONE PARAPHENYLENEDIAMINE DISUBSTITUTED ON ONE OF THE AMINO GROUPS AND METHOD OF IMPLEMENTING |
-
1992
- 1992-02-21 DE DE19924205329 patent/DE4205329A1/en not_active Withdrawn
-
1993
- 1993-02-13 WO PCT/EP1993/000351 patent/WO1993016679A1/en not_active Ceased
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015766A1 (en) * | 1994-11-17 | 1996-05-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation dyes |
| US6277156B1 (en) | 1997-09-01 | 2001-08-21 | L'ORéAL S.A. | Oxidation dyeing composition for keratin fibres comprising 2-chloro-6-methyl-3-aminophenol and an oxidation base, and dyeing method |
| FR2767686A1 (en) * | 1997-09-01 | 1999-03-05 | Oreal | COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL AND TWO OXIDATION BASES, AND DYEING METHOD |
| WO1999011228A1 (en) * | 1997-09-01 | 1999-03-11 | L'oreal | Oxidation dyeing composition for keratin fibres comprising 2-chloro 6 methyl 3-aminophenol, an oxidation base and an additional coupler, and dyeing method |
| WO1999011229A1 (en) * | 1997-09-01 | 1999-03-11 | L'oreal | Oxidation dyeing composition for keratin fibres comprising 2-chloro 6-methyl 3-aminophenol and two oxidation bases, and dyeing method |
| FR2767687A1 (en) * | 1997-09-01 | 1999-03-05 | Oreal | COMPOSITION FOR KERATIN FIBER OXIDATION STAIN COMPRISING 2-CHLORO 6-METHYL 3-AMINOPHENOL, OXIDATION BASE AND ADDITIONAL COUPLER, AND DYEING PROCESS |
| US6306180B1 (en) | 1997-09-01 | 2001-10-23 | L'oreal, S.A. | Oxidation dyeing composition for keratin fibers comprising 2-chloro-6-methyl-3-aminophenol, an oxidation base and an additional coupler, and dyeing method |
| US6379396B1 (en) | 1997-09-01 | 2002-04-30 | L'ORéAL S.A. | Oxidation dyeing composition for keratin fibres comprising 2-chloro 6-methyl 3-aminophenol and two oxidation bases, and dyeing method |
| EP1410788A1 (en) * | 1997-09-01 | 2004-04-21 | L'oreal | Oxidation dyeing composition for keratinous fibres comprising 2-chloro 6 methyl 3-aminophenol, an oxidation base and an additional coupler, and dyeing method |
| EP0966252B1 (en) * | 1997-09-01 | 2004-11-03 | L'oreal | Oxidation dyeing composition for keratin fibres comprising 2-chloro 6 methyl 3-aminophenol and an oxidation base, and dyeing method |
| EP1352636B1 (en) * | 1997-09-01 | 2009-04-22 | L'oreal | Oxidation dyeing composition for keratin fibers comprising 2-chloro-6-methyl-3-aminophenol and an oxidation base, and dyeing method |
| EP1348422B1 (en) * | 1997-09-01 | 2009-04-29 | L'oreal | Oxidation dyeing composition for keratin fibers comprising 2-chloro-6-methyl-3-aminophenol and an oxidation base, and dyeing method |
| WO2000021496A1 (en) * | 1998-10-13 | 2000-04-20 | Wella Aktiengesellschaft | Agent and method for dyeing fibres |
| US6379400B1 (en) | 1998-10-13 | 2002-04-30 | Wella Aktiengesellschaft | Dye compositions and methods of dyeing keratin fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1993016679A1 (en) | 1993-09-02 |
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