WO1998001106A2 - Oxidationsfärbemittel - Google Patents
Oxidationsfärbemittel Download PDFInfo
- Publication number
- WO1998001106A2 WO1998001106A2 PCT/EP1997/003521 EP9703521W WO9801106A2 WO 1998001106 A2 WO1998001106 A2 WO 1998001106A2 EP 9703521 W EP9703521 W EP 9703521W WO 9801106 A2 WO9801106 A2 WO 9801106A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ppm
- alkyl
- amino
- group
- stage
- Prior art date
Links
- 230000003647 oxidation Effects 0.000 title claims abstract description 44
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 44
- 239000000975 dye Substances 0.000 title claims abstract description 36
- -1 2,3-dihydroxypropyl group Chemical group 0.000 claims abstract description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 102000011782 Keratins Human genes 0.000 claims abstract description 9
- 108010076876 Keratins Proteins 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 238000004043 dyeing Methods 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- AXKVOSSFZLZIDC-UHFFFAOYSA-N n,n-diaminoaniline Chemical compound NN(N)C1=CC=CC=C1 AXKVOSSFZLZIDC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004931 azocinyl group Chemical group N1=C(C=CC=CC=C1)* 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004040 coloring Methods 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 239000000982 direct dye Substances 0.000 claims description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 abstract description 7
- 150000007524 organic acids Chemical class 0.000 abstract description 7
- 235000005985 organic acids Nutrition 0.000 abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000003725 azepanyl group Chemical group 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 125000004069 aziridinyl group Chemical group 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000005505 thiomorpholino group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 66
- 238000002360 preparation method Methods 0.000 description 64
- 239000000047 product Substances 0.000 description 61
- 238000005481 NMR spectroscopy Methods 0.000 description 57
- 238000002844 melting Methods 0.000 description 47
- 230000008018 melting Effects 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000003086 colorant Substances 0.000 description 29
- 238000010531 catalytic reduction reaction Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 244000172533 Viola sororia Species 0.000 description 16
- 210000004209 hair Anatomy 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Chemical group 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 11
- 229910052737 gold Inorganic materials 0.000 description 11
- 239000010931 gold Substances 0.000 description 11
- KUAYZLXOOIEGDN-UHFFFAOYSA-N n-(3-chloro-4-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(Cl)=C1 KUAYZLXOOIEGDN-UHFFFAOYSA-N 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000029936 alkylation Effects 0.000 description 10
- 238000005804 alkylation reaction Methods 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 7
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 7
- 239000003444 phase transfer catalyst Substances 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000000118 hair dye Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 5
- SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 229940093915 gynecological organic acid Drugs 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 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 5
- 239000002994 raw material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002888 zwitterionic surfactant Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 4
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- OQBOMBGZJBBZLA-UHFFFAOYSA-N 3-n,3-n-dimethyl-4-nitrobenzene-1,3-diamine Chemical compound CN(C)C1=CC(N)=CC=C1[N+]([O-])=O OQBOMBGZJBBZLA-UHFFFAOYSA-N 0.000 description 4
- GRLKSWWADWGIEU-UHFFFAOYSA-N 3-nitro-4-piperidin-1-ylaniline Chemical compound [O-][N+](=O)C1=CC(N)=CC=C1N1CCCCC1 GRLKSWWADWGIEU-UHFFFAOYSA-N 0.000 description 4
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical class [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 4
- 239000003093 cationic surfactant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002563 ionic surfactant Substances 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000003531 protein hydrolysate Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 description 3
- HHUSNKSIHCUBGP-UHFFFAOYSA-N 2-n,2-n-dimethylbenzene-1,2,4-triamine;sulfuric acid Chemical compound OS(O)(=O)=O.CN(C)C1=CC(N)=CC=C1N HHUSNKSIHCUBGP-UHFFFAOYSA-N 0.000 description 3
- JVEPRDUDSZBOAO-UHFFFAOYSA-N 2-pyrrolidin-1-ylbenzene-1,4-diamine;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC=C(N)C(N2CCCC2)=C1 JVEPRDUDSZBOAO-UHFFFAOYSA-N 0.000 description 3
- CTOCHLXJMWOVHA-UHFFFAOYSA-N 3-[3-amino-4-(azepan-1-yl)anilino]propan-1-ol;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC(NCCCO)=CC=C1N1CCCCCC1 CTOCHLXJMWOVHA-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 3
- AXCMPAWDTLJSBP-UHFFFAOYSA-N 4-(azepan-1-yl)-3-nitroaniline Chemical compound [O-][N+](=O)C1=CC(N)=CC=C1N1CCCCCC1 AXCMPAWDTLJSBP-UHFFFAOYSA-N 0.000 description 3
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000208060 Lawsonia inermis Species 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229960005141 piperazine Drugs 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002453 shampoo Substances 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
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- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin 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
Definitions
- the invention relates to oxidation colorants with special diaminoaniols as oxidation dye precursors.
- oxidation colorants For dyeing keratin fibers, especially human hair, the so-called oxidation colorants play a preferred role because of their intense colors and good fastness properties.
- colorants contain oxidation dye precursors, so-called developer components and coupler components.
- developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
- oxidation dyes must first and foremost meet the following requirements: They must develop the desired color shades with sufficient intensity and authenticity in the oxidative coupling. They must also have a good ability to draw onto the fiber, whereby there must be no noticeable differences between stressed and freshly regrown hair, especially with human hair (leveling ability). They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against perm fluids. After all, if they are used as a hair dye, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view.
- Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-amino-pyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives are examples of developer components used.
- Coupler components usually m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and pyridine derivatives are used as coupler components used.
- coupler components usually m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and pyridine derivatives are used as coupler components used.
- red component is disadvantageous, in particular in the case of lighter shades, but also in order to achieve natural shades which are to have a sufficient depth of color and adequate gray coverage.
- a first subject of the present invention are therefore oxidation colorants for dyeing keratin fibers, which as oxidation dye product have at least one diaminoaniline of the general formula (I),
- R, and R 2 and / or R 3 and R 4 and / or K $ and R "together with the nitrogen atom to which they are attached can also represent an aziridine, azetidine, pyrrolidine, piperidine, azepane -, Azocin ring or a Mo ⁇ holino-, Thiomo ⁇ holino- or Piperazinooire, which carries on the nitrogen atom another substituent R 7 , which is selected from hydrogen, a (C, -C 4 ) alkyl, a hydroxy (C 2 - C 3 ) alkyl, a (C, -C 4 ) alkoxy (C 2 -C 3 ) alkyl, an amino (C 2 -C 3 ) alkyl or a 2,3-dihydroxypropyl group O 98/01106
- the three remaining hydrogen atoms on the benzene ring can also be replaced independently of one another by a halogen atom or a (C, -C 4 ) -alkyl group, or their physiologically tolerable salts with inorganic and organic acids.
- Agents which contain a compound of the formula (I) in which at least two of the groups R to R do not represent hydrogen have particularly excellent coloring properties.
- R to R ⁇ are hydrogen, methyl, ethyl, 2-hydroxyethyl and 3-hydroxypropyl.
- Preferred groups -NR, R 2 , -NR 3 R, and -NR-jR « are pyrrolidine, piperidine, azepane, Mo ⁇ holin and piperazine, the latter bearing hydrogen on the other nitrogen atom.
- the compounds of formula (I) can be used both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, e.g. the hydrochloride, the sulfate and hydrobromide.
- inorganic or organic acids e.g. the hydrochloride, the sulfate and hydrobromide.
- Other acids suitable for salt formation are phosphoric acid and acetic acid, propionic acid, lactic acid and citric acid. The statements made below on the compounds of the formula (I) therefore always include these salts.
- Keratin fibers are to be understood as furs, wool, feathers and in particular human hair.
- oxidation colorants of the invention primarily for 98/011
- Dyeing keratin fibers are suitable, in principle there is nothing to prevent them from being used in other areas, particularly in color photography.
- the hair colorants according to the invention preferably contain the compounds of the formula (I) in an amount of 0.001 to 10% by weight, preferably 0.1 to 5% by weight, in each case based on the total oxidation colorant.
- this agent can either be directly or after mixing with water or e.g. an aqueous solution of an oxidizing agent can be applied to the hair.
- the compounds of the formula (I) can act both as developer and as coupler components in the oxidation colorants according to the invention.
- the agents according to the invention only contain the compounds of the formula (I) as oxidation dye precursors.
- the number of available color shades is significantly increased, however, if the agent contains at least one further oxidation dye product in addition to the compounds of the formula (I).
- the agents according to the invention therefore contain at least one further oxidation dye product of the coupler type.
- Coupler components preferred according to the invention are 1-naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, o-aminophenol, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, l-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 4-chlororesorcinol, 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-
- 1,7-dihydroxynaphthalene, m-aminophenol, 2-methylresorcinol, 4-amino-2-hydroxytoluene, 2-amino-4-hydroxyethylamino-anisole and 2,4-diaminophenoxyethanol are particularly preferred.
- Coupler combinations preferred according to the invention are
- the agents according to the invention therefore contain, if desired, at least one further oxidation dye pre-product of the coupler type, if desired, at least one further oxidation dye pre-product of the developer type.
- Preferred developer components according to the invention are p-phenylenediamine, p-toluenediamine, p-aminophenol, 3-methyl-1,4-diaminobenzene, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis- ( 2-hydroxy-ethyl) -p-phenylenediamine, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolone-5, 4-amino-3-methylphenol , 2-methylamino-4-aminophenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6, -triaminopyrimidine, 2,4-dihydroxy- 5,6-diaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine and 2-hydroxyethy
- p-toluenediamine p-aminophenol, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, 4-amino-3-methylphenol, 2-methylamino-4-aminophenol and 2,4,5, 6-tetraaminopyrimidine.
- this embodiment also includes the use of several additional 98/01106
- Coupler combinations preferred according to the invention are:
- Developer components and coupler components are usually used in approximately molar amounts to one another. If the molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components can preferably be present in the colorant in a molar ratio of 1: 0.5 to 1: 2.
- the total amount of oxidation dye products is generally at most 20% by weight, based on the total agent.
- the colorants according to the invention optionally in addition to further oxidation dye products, additionally contain direct dyes, for example for further modification of the color shades, e.g. from the group of nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols.
- Preferred direct dyes are those with the international names 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, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16, Basic Brown 17, Picramic Acid and Rodol 9 R known compounds as well as 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro -l, 2,3,4-tetrahydroquinoxaline, (N-2,3-dihydroxypropyl-2-nitro-4-trifluoromethyl) amino-benzene and 4-N-ethyl 1 - 1, 4-bis (2 '- hydroxyethylamino) -2-nitrobenzene hydrochloride.
- the agents according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
- the colorants according to the invention can also include naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, 98/01106
- the mandatory or optional oxidation dyes or the optional direct dyes each represent uniform compounds. Rather, in the hair colorants according to the invention, due to the production processes for the individual dyes, further components may also be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. toxicological, must be excluded.
- Usual formulations for the oxidation coloring agents according to the invention are agents based on water or non-aqueous solvents as well as powders.
- the oxidation dye pre-products are incorporated into a suitable water-containing carrier.
- suitable water-containing carrier e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions, e.g. Shampoos, aerosols or other preparations that are suitable for use on the hair.
- the colorants according to the invention are preferably adjusted to a pH of 6.5 to 11.5, in particular 9 to 10.
- the colorants according to the invention can contain all active ingredients, additives and auxiliaries known in such preparations.
- the colorants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle.
- anionic surfactants can be very particularly preferred.
- Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms. In addition, in the molecule 98/01106
- Glycol or polyglycol ether groups, ether, amide and hydroxyl groups and usually also ester groups may be included.
- suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
- Atoms in the alkyl group and 1 to 6 oxyethyl groups linear alkanesulfonates with 12 to 18 C atoms, linear alpha-olefin sulfonates with 12 to 18 C atoms,
- Alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 carbon atoms are alpha-sulfofatty acids methyl esters of fatty acids with 12 to 18 carbon atoms,
- RO (-CH2-CH2 ⁇ ) ⁇ -S ⁇ 3H in which R is a preferably linear alkyl group with 10 to
- esters of tartaric acid and citric acid with alcohols the additive
- Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C8-C22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
- Zwitterionic surfactants are those surface-active compounds which contain at least one quaternary ammonium group and at least one -CO ⁇ ( " ) - or wear.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyl dimethyl-onium-glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacyl-aminoethyl-hydroxyethylcarboxymethylglycinate.
- a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamido
- Ampholytic surfactants are surface-active compounds which, in addition to a C8-C18-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts.
- ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkylimino dipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C12-18 acylsarcosine.
- Nonionic surfactants contain z as a hydrophilic group.
- B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
- Such connections are, for example
- Examples of the cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
- Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for.
- the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
- cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning® 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quatemium-80).
- alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
- esters such as the dialkylammo- sold under the trademark Stepantex ® , are also readily biodegradable. 98/01106
- a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to CTFA nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
- the compounds with alkyl groups used as surfactants can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
- both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
- “Normal” homolog distribution is understood to mean mixtures of homologues which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
- narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
- non-ionic polymers such as, for example, vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyl amidolamethylamethylamidylamethylamidylamethylamidylamethylamidylamethylamidylamethylamidylamethylamidylamethylamidylamethylamidylamidylamethylamidylamidylamethylpolymer Imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, 1106
- zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate tert.butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate
- Copolymers such as polyacrylic acids, cross-linked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride tert-copolymers and acrylic acid / acrylic acid / acrylic acid copolymers.
- anionic polymers such as polyacrylic acids, cross-linked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride tert-copolymers and acrylic acid / acrylic acid / acrylic acid copolymers.
- Butylacrylamide polymers such as polyacrylic acids, cross-linked polyacrylic
- Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans,
- Cellulose derivatives e.g. B. methyl cellulose, hydroxyalkyl cellulose and
- Amylopectin and dextrins clays such as e.g. B. bentonite or fully synthetic
- Hydrocolloids such as Polyvinyl alcohol,
- Structurants such as glucose, maleic acid and lactic acid, hair-conditioning compounds such as phospholipids, for example
- Soy lecithin, egg lecithin and cephaline, as well as silicone oils are soy lecithin, egg lecithin and cephaline, as well as silicone oils,
- Protein hydrolyzates especially elastin, collagen, keratin, milk protein,
- Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol,
- Anti-dandruff agents such as piroctone olamine and zinc omadine
- Alkalizing agents such as ammonia, monoethanolamine, 2-amino
- Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins,
- Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
- Fats and waxes such as whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, 98/01106
- Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether,
- Pearlescent agents such as ethylene glycol mono- and distearate
- Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and
- constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; e.g. emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
- the oxidative development of the coloring can in principle take place with atmospheric oxygen or an oxidizing agent contained in the agent or added to it immediately before use.
- a chemical oxidizing agent is used. This is particularly advantageous in cases where, in addition to the coloring, a lightening effect on human hair is desired.
- Particularly suitable oxidizing agents are hydrogen peroxide or its adducts with urea, melamine or alkali borate.
- the colorant according to the invention is mixed with the preparation of the oxidizing agent, in particular an aqueous H 2 O 2 solution, immediately before use.
- the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
- the application temperatures can range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is removed from the hair to be colored by rinsing.
- washing with a shampoo is not necessary if a strong surfactant carrier, e.g. a coloring shampoo was used.
- the preparation with the oxidation dye pre-products can be applied to the hair without prior mixing with the oxidation component. After an exposure time of 20 to 30 minutes, the oxidation component is then applied, if necessary after an intermediate rinse. After a further exposure time of 10 to 20 minutes, rinsing is then carried out and, if desired, re-shampooing.
- the coloring takes place with atmospheric oxygen. It is advantageous to add an oxidation catalyst to the colorant according to the invention.
- Suitable oxidation catalysts are metal salts or metal complexes, with transition metals being preferred. Copper, manganese, cobalt, selenium, molybdenum, bismuth and ruthenium compounds are preferred. Copper (II) chloride, sulfate and acetate can be preferred oxidation catalysts.
- the complexes with ammonia, ethylenediamine, phenanthroline, triphenylphosphine, 1,2-diphenylphosphinoethane, 1,3-diphenylphosphinopropane or amino acids can be preferred as metal complexes.
- the metal salts or metal complexes are preferably present in the agents according to the invention in amounts of 0.0001 to 1% by weight, based on the total agent.
- suitable catalysts reference is made to the corresponding disclosure in EP 0 709 365 AI (page 4, lines 19 to 42), to which reference is expressly made.
- the enzymes can be used both to produce oxidizing per compounds and to enhance the effect of a small amount of oxidizing agents present.
- An example of an enzymatic process is the procedure to increase the effect of small amounts (e.g. 1% and less, based on the total agent) of hydrogen peroxide by peroxidases.
- Another object of the invention is the use of diaminoanilines of the general formula (I) according to claim 1 for dyeing keratin fibers.
- the following examples are intended to explain the subject of the invention in more detail
- Suitable phase transfer catalysts are, for example, methyl or benzyl tri (C 6 - C 8 ) alkylammonium chloride.
- This reaction can optionally be carried out in an autoclave under pressure if the boiling point of the amine is lower than the reaction temperature or the conversion is not complete.
- the compounds of the general formula (IV) are reduced to the compounds of the general formula (V), optionally alkylated or oxyalkylated to the compounds of the general formula (I) according to the invention and optionally converted into their salts with inorganic or organic acids.
- the compounds of the general formula (III) are common chemical raw materials and can be purchased.
- the compounds of the general formula (I) according to the invention can be obtained by first substituting substituted 4-amino-2-nitrohalobenzenes of the general formula (VI) with amines of the general formula (III) to give compounds of the general formula (VII) be implemented.
- the compounds of the general formula (VII) are converted into the compounds of the general formula (I) by reduction and, if appropriate, subsequent alkylation or oxalkylation.
- the compounds of the general formula (I) according to the invention can be obtained by substituting substituted 2-amino-4-nitrohalobenzenes of the general formula (Via) with amines of the general formula
- the compounds of the general formula (VIIa) are converted into the compounds of the general formula (I) by reduction and, if appropriate, subsequent alkylation or oxalkylation.
- the compounds of the general formula (I) according to the invention can be obtained by substituting 3-amino-4-nitrohalobenzenes of the general formula (VIb) with amines of the general formula
- phase transfer catalysts are, for example, methyl or benzyl tri (C 6 -C g ) alkylammonium chloride. This reaction can optionally be carried out in an autoclave under pressure if the boiling point of the amine is lower than the reaction temperature or the conversion is not complete.
- the compounds of the general formula (purple) are common chemical raw materials and can be purchased.
- the compounds of the general formula (IV) are converted into the compounds of the general formula (I) and, if appropriate, with acids in their salts by hydrolysis and, if appropriate, alkylation or oxyalkylation, reduction and, if appropriate, further alkylation or oxyalkylation.
- the compounds of the general formula (I) according to the invention can be obtained by substituting 2-nitro-5-aminohalobenzenes of the general formula (VI) ', where R 5 and R ⁇ have the meaning given in claim 1 Amines of the general formula (III) initially
- the compounds of the general formula (VHb) are then converted into the compounds of the general formula (I) by reduction and, if appropriate, subsequent alkylation or oxalkylation.
- phase transfer catalysts are, for example, methyl- or benzyl-tri (C 6 -C 8 ) alkylammonium chloride. This reaction can optionally be carried out in an autoclave under pressure if the boiling point of the amine is lower than the reaction temperature or the conversion is not complete.
- the compounds of the general formula (IV) "are hydrolyzed to the compounds of the general formula (VHb) and, if appropriate, reduced and reduced after alkylation or oxalkylation the compounds of general formula (I) according to the invention are further alkylated or oxyalkylated and optionally converted into their salts with inorganic or organic acids.
- the compounds of the general formula (IIIb) are customary chemical raw materials and can be purchased.
- the first stage of these processes consists in principle of replacing a halogen substituent with an amine substituent on the phenyl ring.
- an amine excess of about 40-80% is usually used; the products are obtained in yields of approx. 90% and with a purity of 95-96%.
- the amine excess is 30% and less, in particular 5 to 10 mol%, based on the amounts of the compound of the formula (II), (VI ), (Via), (VIb), (II) ', (VI)' and (II) ".
- the reaction of the amines (III), (purple) or (Illb) with compounds of the formula (II), ( VI), (Via), (VIb), (II) ', (VI)' and (II) " is preferably carried out in the presence of alkali carbonates as acid-binding agents. It is also preferred to carry out the reaction in an organic solvent.
- the reaction is preferably carried out under a pressure of from 1 to 15 bar, in particular from 1 to 8 bar and very particularly preferably from 1 to 2.5 bar.
- the compounds of the general formula (I) can be prepared by reducing the compounds of the general formula (V) ', (IV), (VII), (VIIa) or (VHb), optionally after alkylation or oxalkylation, with base metals or by catalytic reduction take place.
- conventional catalysts e.g. B. Raney nickel, palladium on activated carbon or platinum on activated carbon.
- the reaction temperature is between room temperature and 120 ° C, preferably between 35 and 100 ° C, the pressure is between normal pressure and 20 bar, preferably between 2 and 7 bar.
- Common solvents such as water, toluene, glacial acetic acid, lower alcohols or ethers are used as solvents.
- the known compounds dimethyl and diethyl sulfate have proven to be suitable as alkylating agents and the known compounds ethylene oxide and propylene oxide have proven useful as oxyalkylating agents.
- the product of the general formula (I) is preferably converted under a protective gas by adding a 1.0 to 1.1 equivalent amount of an acid into a salt which either precipitates directly or is obtained after removal of the solvent.
- inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid and as organic acids acetic acid, propionic acid, lactic acid or citric acid suitable for salt formation.
- the compounds prepared have been characterized by IR or IR (KBr compact) and 'H-NMR spectra (in D 6 -DMSO). Only the very strong and strong bands are listed in the IR spectra.
- IR or IR KBr compact
- 'H-NMR spectra s singlet, d doublet, dd doublet from the doublet, t triplet, q quartet, qi quintet, m multiple «, 3 J or 4 J mean the coupling via three or four bonds , as well as H ⁇ H ⁇ H 4 , H 5 and H 6 the hydrogen atoms in position 2, 3, 4, 5 and 6 of the benzene ring.
- the mixture was allowed to cool to room temperature while stirring and then to 10 ° C. in an ice bath, the product precipitating out.
- the precipitated product was filtered off, washed twice with about 100 ml of water and dried at 40 ° C in a vacuum.
- stage a 150 ml of methanol were placed in a 0.3 l autoclave, 42.2 g (0.2 mol) of NN-dimethyl-2,4-dinitroaniline (stage a; alternatively also the compound according to Example 1.3.8 stage a) were dissolved and 2 g of palladium on activated carbon 10% (Degussa) were added. After sealing and inerting with nitrogen, the mixture was hydrogenated at a pressure of 3 bar and a temperature of 35-40 ° C. until no more hydrogen was taken up. 1.3 g of activated carbon were added to the warm solution under nitrogen and the catalyst was filtered off.
- Washed water and dried at 40 ° C in a vacuum Washed water and dried at 40 ° C in a vacuum.
- Stage a) was carried out analogously to Example 1.3.1. Stage a) through
- Stage a) was carried out analogously to Example 1.3.1. Stage a) through
- Stage a) was carried out analogously to Example 1.3.5. Step a) by reacting 2,4-dinitrochlorobenzene with pyrrolidine.
- stage a) The reaction in stage a) was carried out analogously to example 1.3.1. Stage a) below
- Stage a) was analogous to Example 1.3.1. Stage a) by implementing 2.4-
- Step b) 4- (2-chloroethoxycarbonylamino) -2-nitro-N, N-dimethylaniline 28.5 g (160 mmol) of 4-amino-2-nitro-N, N-dime were added to 100 ml of 1,2-dimethoxyethane - Thylaniline and 9 g (80 mmol) calcium carbonate presented. 22.5 g (160 mmol) of 2-chloroethyl chloroformate were added dropwise to this solution at room temperature and the mixture was stirred until the conversion was complete. The pH was then adjusted to 3-4 using concentrated hydrochloric acid and 100 g of ice / water mixture were added. The precipitated product was filtered off and washed twice with 100 ml of water.
- Stage a) was carried out analogously to Example 1.3.9. Stage a) through
- stage b) N- [4- (2-chloroethoxycarbonylamino) -2-nitrophenyl] morpholine
- the preparation in stage b) was carried out analogously to Example 1.3.9.
- Step b) by reaction of N- (4-amino-2-nitrophenyl) mo ⁇ holin with 2-chloroethyl chloroformate.
- Stage c) was analogous to Example 1.3.9. Stage c) by converting N- [4- (2-chloroethoxycarbonylamino) -2-nitrophenyl] mo ⁇ holin with potassium hydroxide solution. Yield: 20 g (93.5% of theory)
- stage ⁇ ) N- [4- (2-hydroxyethylamino) -2-aminophenyl] morpholine sulfate The reaction in stage d) was carried out analogously to Example 1.3.9 stage d) by catalytic reduction of the product obtained in stage c) and subsequent Precipitation with sulfuric acid. Yield: 7.4 g (28.3% of theory)
- Stage a) was carried out analogously to Example 1.3.9. Step a) by reaction of 4-fluoro-3-nitraniline with piperidine.
- N- [4- (2-chloroethoxycarbonylamino) -2-nitrophenyl] piperidine stage b) was carried out analogously to Example 1.3.9.
- Step b) was carried out by reacting N- (4-amino-2-nitrophenyl) piperidine with 2-chloroethyl chloroformate. Yield: 31.1 g (94.8% of theory)
- stage d) The reaction in stage d) was carried out analogously to example 1.3.9. Stage d) by catalytic reduction of the product obtained in stage c) and subsequent precipitation with sulfuric acid.
- Stage a) was carried out by reacting 4-fluoro-3-nitraniline with
- the compound was formed by conversion of N- (4-amino-2-nitrophenyl) mo ⁇ holin with
- the compound was obtained by converting N- [4- (3-chloropropoxycarbonylarnino) -2-nitrophenyljmo ⁇ holin with sodium hydroxide solution in analogy to Example 1.3.10. Stage c) made.
- the product was obtained by catalytic reduction of the product obtained in step c) above and salt formation with hydrochloric acid.
- Stage a) was carried out analogously to Example 1.3.9. Step a) by reaction of 4-fluoro-3-nitraniline with piperidine.
- Stage b) was analogous to Example 1.3.9.
- Step b) was carried out by reacting N- (4-amino-2-nitrophenyl) piperidine with 3-chloroformate chloroformate.
- stage d) The reaction in stage d) was carried out analogously to example 1.3.9. Stage d) by catalytic reduction of the product obtained in stage c) and subsequent precipitation with sulfuric acid.
- Stage a) was carried out analogously to Example 1.3.9. Step a) by reaction of 4-fluoro-3-nitraniline with pyrrolidine.
- Stage b) was analogous to Example 1.3.9.
- Step b) was carried out by reacting N- (4-amino-2-nitrophenyl) pyrrolidine with 3-chloroformate chloroformate.
- stage d) The reaction in stage d) was carried out analogously to example 1.3.9. Stage d) by catalytic reduction of the product obtained in stage c) and subsequent precipitation with sulfuric acid.
- Stage a) was carried out analogously to Example 1.3.9. Step a) by reaction of 4-fluoro-3-nitraniline with azepane.
- Stage b) was analogous to Example 1.3.9.
- Step b) carried out by reacting N- (4-amino-2-nitrophenyl) azepane with 3-chloroformate chloroformate.
- stage d) The reaction in stage d) was carried out analogously to example 1.3.9 stage d) by catalytic reduction of the product obtained in stage c) and subsequent precipitation with sulfuric acid.
- stage b) The reaction in stage b) was carried out analogously to example 1.3.9.
- Stage d) by catalytic reduction of the product obtained in stage a) and subsequent precipitation with sulfuric acid.
- the product was filtered off and washed with water.
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N-ethyl-2-nitro-5-aminoaniline. Yield: 15.4 g (85.8% of theory)
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N - «- propyl-2-nitro-5-aminoaniline. Yield: 12.1 g (83.5% of theory)
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.17. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N-wo-butyl-2-nitro-5-aminoaniline.
- Stage a) was carried out analogously to Example 1.3.17. Step a) by reacting 2-nitro-5-acetylaminochlorobenzene with dimethylamine. Yield: 16.8 g (75.5% of theory) of yellow crystals
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.17. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N, N-dimethyl-2-nitro-5-aminoaniline.
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.17. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N, N-diethyI-2-nitro-5-aminoaniline. Yield: 10.1 g (64.3% of theory)
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.17. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N- (5-amino-2-nitrophenyl) pyrrolidine. Yield: 13.5 g (59.5% of theory)
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.17. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N- (5-amino-2-nitrophenyl) piperidine.
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.17. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N- (5-amino-2-nitrophenyl) azepane.
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N- (5-amino-2-nitrophenyl) mo ⁇ holin. Yield: 22.3 g (95.7% of theory)
- Stage a) was carried out analogously to Example 1.3.17. Stage a) through
- stage c) The preparation in stage c) was carried out analogously to Example 1.3.17. Step c) by catalytic reduction of N- (5-amino-2-nitrophenyl) piperazine. Yield: 13.2 g (75.8% of theory)
- Stage a) was carried out analogously to Example 1.3.28. Stage a) through
- stage b) The preparation in stage b) was carried out analogously to Example 1.3.28. Stage b) through
- stage c) The preparation in stage c) was carried out analogously to example 1.3.28. Step c) by catalytic reduction of N- (4-nitro-3-aminophenyl) -m ⁇ holin.
- Oleic acid 12.0 g
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97931764A EP0912160A2 (de) | 1996-07-03 | 1997-07-03 | Oxidationsfärbemittel |
JP10504764A JP2000514073A (ja) | 1996-07-03 | 1997-07-03 | 酸化染料 |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19626682.3 | 1996-07-03 | ||
DE19626617.3 | 1996-07-03 | ||
DE19626682 | 1996-07-03 | ||
DE19626744 | 1996-07-03 | ||
DE19626744.7 | 1996-07-03 | ||
DE19626617 | 1996-07-03 |
Publications (2)
Publication Number | Publication Date |
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WO1998001106A2 true WO1998001106A2 (de) | 1998-01-15 |
WO1998001106A3 WO1998001106A3 (de) | 1998-03-05 |
Family
ID=27216407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/003521 WO1998001106A2 (de) | 1996-07-03 | 1997-07-03 | Oxidationsfärbemittel |
Country Status (4)
Country | Link |
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US (1) | US20010005914A1 (de) |
EP (1) | EP0912160A2 (de) |
JP (1) | JP2000514073A (de) |
WO (1) | WO1998001106A2 (de) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11349564A (ja) * | 1998-05-13 | 1999-12-21 | Bristol Myers Squibb Co | 1―(4―アミノフェニル)―2―ピロリジンメタノ―ルを含有する酸化染毛組成物及び方法 |
WO2001041724A2 (fr) * | 1999-12-08 | 2001-06-14 | L'oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement azetidinyle |
EP1110942A2 (de) * | 1999-12-18 | 2001-06-27 | Wella Aktiengesellschaft | Verfahren zur Herstellung von 2-Aminomethyl-1,4-diamino-benzol und dessen Salzen sowie die Verwendung dieser Verbindungen in Färbemitteln für Keratinfasern |
FR2807651A1 (fr) * | 2000-04-18 | 2001-10-19 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant une 1-(4-aminophenyl)-pyrrolidine et un polymere epaississant a motif sucre |
FR2807650A1 (fr) * | 2000-04-18 | 2001-10-19 | Oreal | Composition de teinture d'oxydation des fibres keratiniques comprenant 1-(4-aminophenyl)-pyrrolidine et un colorant direct particulier |
FR2807652A1 (fr) * | 2000-04-18 | 2001-10-19 | Oreal | Composition pour la teinture d'oxydation des fibres comprenant une 1-(4-aminophenyl)-pyrrolidine et un polymere cationique |
WO2001078665A1 (de) * | 2000-04-12 | 2001-10-25 | Henkel Kommanditgesellschaft Auf Aktien | Färbemittel mit rutheniumverbindungen |
WO2004031164A1 (de) * | 2002-09-27 | 2004-04-15 | Henkel Kommanditgesellschaft Auf Aktien | Haarfärbemittel mit m-phenylendiaminderivaten als kupplerkomponenten |
EP1512684A1 (de) * | 2003-09-04 | 2005-03-09 | L'oreal | Verwendung von Phenylen-Diamino Derivate substituirte durch ein Homopiperidine zum Färben von Keratinhaltigen Fasern |
TWI691641B (zh) * | 2018-04-27 | 2020-04-21 | 虹運鋼鐵有限公司 | 可拆式管件固定座 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2992646B1 (fr) * | 2012-07-02 | 2014-06-20 | Oreal | Composition tinctoriale comprenant une meta-phenylenediamine cationique |
ITUA20161586A1 (it) * | 2016-03-11 | 2017-09-11 | Beauty & Business S P A | Composizione per colorare la fibra cheratinica |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1136996A (fr) * | 1955-11-18 | 1957-05-22 | Oreal | Procédé et composition pour teindre les cheveux et fibres analogues |
FR1505442A (fr) * | 1965-09-23 | 1967-12-15 | Gillette Co | Composés trisubstitués de benzène utilisables dans la teinture des matières kératineuses |
GB2018836A (en) * | 1978-04-06 | 1979-10-24 | Oreal | Two-stage process for dyeing keratin fibres and composition for use therein |
-
1997
- 1997-07-03 US US09/214,062 patent/US20010005914A1/en not_active Abandoned
- 1997-07-03 WO PCT/EP1997/003521 patent/WO1998001106A2/de not_active Application Discontinuation
- 1997-07-03 JP JP10504764A patent/JP2000514073A/ja active Pending
- 1997-07-03 EP EP97931764A patent/EP0912160A2/de not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1136996A (fr) * | 1955-11-18 | 1957-05-22 | Oreal | Procédé et composition pour teindre les cheveux et fibres analogues |
FR1505442A (fr) * | 1965-09-23 | 1967-12-15 | Gillette Co | Composés trisubstitués de benzène utilisables dans la teinture des matières kératineuses |
GB2018836A (en) * | 1978-04-06 | 1979-10-24 | Oreal | Two-stage process for dyeing keratin fibres and composition for use therein |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11349564A (ja) * | 1998-05-13 | 1999-12-21 | Bristol Myers Squibb Co | 1―(4―アミノフェニル)―2―ピロリジンメタノ―ルを含有する酸化染毛組成物及び方法 |
WO2001041724A3 (fr) * | 1999-12-08 | 2001-12-20 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement azetidinyle |
WO2001041724A2 (fr) * | 1999-12-08 | 2001-06-14 | L'oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement azetidinyle |
FR2802091A1 (fr) * | 1999-12-08 | 2001-06-15 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement azetidinyle |
EP1110942A2 (de) * | 1999-12-18 | 2001-06-27 | Wella Aktiengesellschaft | Verfahren zur Herstellung von 2-Aminomethyl-1,4-diamino-benzol und dessen Salzen sowie die Verwendung dieser Verbindungen in Färbemitteln für Keratinfasern |
EP1310479A1 (de) * | 1999-12-18 | 2003-05-14 | Wella Aktiengesellschaft | Verfahren zur Herstellung von 2-Aminomethyl-1,4-diamino-benzol und dessen Salzen |
US6461390B1 (en) | 1999-12-18 | 2002-10-08 | Wella Aktiengesellschaft | Process for making 2-aminomethyl-1, 4-diaminobenzene and its salts and compositions and methods for dyeing keratin fibers using same |
EP1110942A3 (de) * | 1999-12-18 | 2002-02-06 | Wella Aktiengesellschaft | Verfahren zur Herstellung von 2-Aminomethyl-1,4-diamino-benzol und dessen Salzen sowie die Verwendung dieser Verbindungen in Färbemitteln für Keratinfasern |
WO2001078665A1 (de) * | 2000-04-12 | 2001-10-25 | Henkel Kommanditgesellschaft Auf Aktien | Färbemittel mit rutheniumverbindungen |
FR2807651A1 (fr) * | 2000-04-18 | 2001-10-19 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant une 1-(4-aminophenyl)-pyrrolidine et un polymere epaississant a motif sucre |
EP1149575A1 (de) * | 2000-04-18 | 2001-10-31 | L'oreal | Mittel zum oxidativen Färben von Keratinfasern enthaltend 1-(4-Aminophenyl)pyrrolidin und einen direktziehenden bestimmten Farbstoff |
EP1149576A1 (de) * | 2000-04-18 | 2001-10-31 | L'oreal | Mittel zum oxidativen Färben von Keratinfasern enthaltend 1-(4-Aminophenyl)pyrrolidin und ein Verdickendes Polymer auf Basis von Zucker |
EP1149577A1 (de) * | 2000-04-18 | 2001-10-31 | L'oreal | Mittel zum oxidativen Färben von Keratinfasern enthaltend 1-Aminophenylpyrrolidin und ein kationisches Polymer |
FR2807652A1 (fr) * | 2000-04-18 | 2001-10-19 | Oreal | Composition pour la teinture d'oxydation des fibres comprenant une 1-(4-aminophenyl)-pyrrolidine et un polymere cationique |
FR2807650A1 (fr) * | 2000-04-18 | 2001-10-19 | Oreal | Composition de teinture d'oxydation des fibres keratiniques comprenant 1-(4-aminophenyl)-pyrrolidine et un colorant direct particulier |
WO2004031164A1 (de) * | 2002-09-27 | 2004-04-15 | Henkel Kommanditgesellschaft Auf Aktien | Haarfärbemittel mit m-phenylendiaminderivaten als kupplerkomponenten |
EP1512684A1 (de) * | 2003-09-04 | 2005-03-09 | L'oreal | Verwendung von Phenylen-Diamino Derivate substituirte durch ein Homopiperidine zum Färben von Keratinhaltigen Fasern |
TWI691641B (zh) * | 2018-04-27 | 2020-04-21 | 虹運鋼鐵有限公司 | 可拆式管件固定座 |
Also Published As
Publication number | Publication date |
---|---|
JP2000514073A (ja) | 2000-10-24 |
WO1998001106A3 (de) | 1998-03-05 |
EP0912160A2 (de) | 1999-05-06 |
US20010005914A1 (en) | 2001-07-05 |
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