NL194164C - N of N' (mono- of N,N'di) gesubstitueerde 2,4-diamino -5-halogeennitrobenzeenverbindingen en verfpreparaten voor keratinevezels, welke ten minste een dergelijke 2,4-diaminonitrobenzeenverbinding bezitten. - Google Patents
N of N' (mono- of N,N'di) gesubstitueerde 2,4-diamino -5-halogeennitrobenzeenverbindingen en verfpreparaten voor keratinevezels, welke ten minste een dergelijke 2,4-diaminonitrobenzeenverbinding bezitten. Download PDFInfo
- Publication number
- NL194164C NL194164C NL8601506A NL8601506A NL194164C NL 194164 C NL194164 C NL 194164C NL 8601506 A NL8601506 A NL 8601506A NL 8601506 A NL8601506 A NL 8601506A NL 194164 C NL194164 C NL 194164C
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- formula
- hair
- nitro
- water
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 36
- 239000003973 paint Substances 0.000 title claims description 20
- -1 2,4-diamino nitrobenzene compound Chemical class 0.000 title claims description 17
- 239000000835 fiber Substances 0.000 title claims description 17
- 102000011782 Keratins Human genes 0.000 title claims description 10
- 108010076876 Keratins Proteins 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000975 dye Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 238000004043 dyeing Methods 0.000 claims description 9
- 238000004040 coloring Methods 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 claims description 4
- 229940063953 ammonium lauryl sulfate Drugs 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 239000001005 nitro dye Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 claims description 4
- LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- CGFLXNWWUXLUIX-UHFFFAOYSA-M hexadecyl-(2-hydroxyethyl)-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCO CGFLXNWWUXLUIX-UHFFFAOYSA-M 0.000 claims description 2
- 229910000906 Bronze Inorganic materials 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000010974 bronze Substances 0.000 claims 1
- 239000004359 castor oil Substances 0.000 claims 1
- 235000019438 castor oil Nutrition 0.000 claims 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000005457 ice water Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- IBRBMZRLVYKVRF-UHFFFAOYSA-N 1,2,4-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1Cl IBRBMZRLVYKVRF-UHFFFAOYSA-N 0.000 description 3
- JBXZCPXEYAEMJS-UHFFFAOYSA-N 2,5-dichloro-4-nitroaniline Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl JBXZCPXEYAEMJS-UHFFFAOYSA-N 0.000 description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 239000007800 oxidant agent Substances 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- DPRUDYUABBVYEQ-UHFFFAOYSA-N 1,2-diethyl-1-(4-nitrophenyl)hydrazine Chemical compound C(C)NN(C1=CC=C(C=C1)[N+](=O)[O-])CC DPRUDYUABBVYEQ-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- HIWDXBJNFAODRX-UHFFFAOYSA-N 2,5-dichloro-n-ethyl-4-nitroaniline Chemical compound CCNC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl HIWDXBJNFAODRX-UHFFFAOYSA-N 0.000 description 2
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- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- KVAANWDMOIROOR-UHFFFAOYSA-N 4,5-dichloro-n-methyl-2-nitroaniline Chemical compound CNC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O KVAANWDMOIROOR-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
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- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000003113 alkalizing effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
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- 239000000118 hair dye Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
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- 125000005647 linker group Chemical group 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- CZWAKKXKPYAFFV-UHFFFAOYSA-N n-(2,5-dichloro-4-nitrophenyl)benzenesulfonamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(Cl)=C1NS(=O)(=O)C1=CC=CC=C1 CZWAKKXKPYAFFV-UHFFFAOYSA-N 0.000 description 2
- BMXVRLGVIWBKCC-UHFFFAOYSA-N n-(2,5-dichlorophenyl)benzenesulfonamide Chemical compound ClC1=CC=C(Cl)C(NS(=O)(=O)C=2C=CC=CC=2)=C1 BMXVRLGVIWBKCC-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- 235000010288 sodium nitrite Nutrition 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical class CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
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- FTJRNKKDQVQZHU-UHFFFAOYSA-N 2-ethyl-N-phenylbenzenesulfonamide Chemical compound C(C)C1=C(C=CC=C1)S(=O)(=O)NC1=CC=CC=C1 FTJRNKKDQVQZHU-UHFFFAOYSA-N 0.000 description 1
- BVWOHFHLLLPJLH-UHFFFAOYSA-N 2-methoxy-3,5-dimethylbenzene-1,4-diamine Chemical compound COC1=C(C)C(N)=C(C)C=C1N BVWOHFHLLLPJLH-UHFFFAOYSA-N 0.000 description 1
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 1
- UVUGDGRIYQQKIT-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-amine Chemical compound O1CCNC2=CC(N)=CC=C21 UVUGDGRIYQQKIT-UHFFFAOYSA-N 0.000 description 1
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 description 1
- XEMWHIJWZOJWNP-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-7-amine Chemical compound N1CCOC2=CC(N)=CC=C21 XEMWHIJWZOJWNP-UHFFFAOYSA-N 0.000 description 1
- LGCKDTFGHANYMI-UHFFFAOYSA-N 3,6-dichloro-6-(4-nitrophenyl)sulfonylcyclohexa-2,4-dien-1-amine Chemical compound ClC1(C(N)C=C(C=C1)Cl)S(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-] LGCKDTFGHANYMI-UHFFFAOYSA-N 0.000 description 1
- BEJQXBXPRXFJDP-UHFFFAOYSA-N 3-(3,3-dihydroxypropoxy)propane-1,1-diol Chemical compound OC(O)CCOCCC(O)O BEJQXBXPRXFJDP-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- OKWKVPHHASDMRZ-UHFFFAOYSA-N 4-(2-phenyldiazenylphenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1N=NC1=CC=CC=C1 OKWKVPHHASDMRZ-UHFFFAOYSA-N 0.000 description 1
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 description 1
- PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 description 1
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 1
- DPIZKMGPXNXSGL-UHFFFAOYSA-N 4-nitro-1,3-phenylenediamine Chemical class NC1=CC=C([N+]([O-])=O)C(N)=C1 DPIZKMGPXNXSGL-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
- 244000215068 Acacia senegal Species 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000640882 Condea Species 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Chemical class 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000205 acacia gum Chemical class 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- GQZYJXVNALEKLC-UHFFFAOYSA-N aniline;ethanol Chemical compound CCO.NC1=CC=CC=C1 GQZYJXVNALEKLC-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- HLKZFSVWBQSKKH-UHFFFAOYSA-N but-3-enoic acid;1-ethenylpyrrolidin-2-one Chemical compound OC(=O)CC=C.C=CN1CCCC1=O HLKZFSVWBQSKKH-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008407 cosmetic solvent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical class CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UMVWJRMJMOPKKM-UHFFFAOYSA-N ethyl n-(3-hydroxy-4-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(C)C(O)=C1 UMVWJRMJMOPKKM-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- RFUORPICHNGUJN-UHFFFAOYSA-N n-(3-hydroxy-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(O)=C1 RFUORPICHNGUJN-UHFFFAOYSA-N 0.000 description 1
- ZUUVIUQJGHXICN-UHFFFAOYSA-N n-ethyl-n-phenylnitramide Chemical compound CCN([N+]([O-])=O)C1=CC=CC=C1 ZUUVIUQJGHXICN-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000000230 xanthan gum Chemical class 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Chemical class 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- 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
- A61K8/418—Amines containing nitro groups
-
- 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/16—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU85939A LU85939A1 (fr) | 1985-06-10 | 1985-06-10 | Nouvelles metaphenylenediamines nitrees,halogenees en position 6 et leur utilisation en teinture des matieres keratiiques |
| LU85939 | 1985-06-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8601506A NL8601506A (nl) | 1987-01-02 |
| NL194164B NL194164B (nl) | 2001-04-02 |
| NL194164C true NL194164C (nl) | 2001-08-03 |
Family
ID=19730482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8601506A NL194164C (nl) | 1985-06-10 | 1986-06-10 | N of N' (mono- of N,N'di) gesubstitueerde 2,4-diamino -5-halogeennitrobenzeenverbindingen en verfpreparaten voor keratinevezels, welke ten minste een dergelijke 2,4-diaminonitrobenzeenverbinding bezitten. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4666453A (en, 2012) |
| JP (1) | JPH0639455B2 (en, 2012) |
| AT (1) | AT401343B (en, 2012) |
| BE (1) | BE904890A (en, 2012) |
| CA (1) | CA1266488A1 (en, 2012) |
| CH (1) | CH670086A5 (en, 2012) |
| DE (1) | DE3619227C2 (en, 2012) |
| FR (1) | FR2583044B1 (en, 2012) |
| GB (3) | GB2176494B (en, 2012) |
| IT (1) | IT1190586B (en, 2012) |
| LU (1) | LU85939A1 (en, 2012) |
| NL (1) | NL194164C (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3543020A1 (de) * | 1985-12-05 | 1987-06-11 | Wella Ag | Verfahren zur herstellung von 4-(ethyl-(2'hydroxyethyl)-amino)-1-((2'-hydroxyethyl)-amino)-2-nitro-benzol |
| LU86309A1 (fr) * | 1986-02-14 | 1987-09-10 | Oreal | Composition pour fibres keratiniques et en particulier pour cheveux humains,a base de nitroanilines halogenes,procede de teinture utilisant ladite composition tinctoriale et nouvelles 2-nitroanilines halogenees utilisees |
| US4871372A (en) * | 1987-07-17 | 1989-10-03 | Kao Corporation | Dye composition for keratinous fiber |
| JP2640822B2 (ja) * | 1988-02-22 | 1997-08-13 | 北興化学工業株式会社 | イソオキサゾリジン類の製造方法 |
| DE3917114C3 (de) * | 1989-05-26 | 1996-08-14 | Schwarzkopf Gmbh Hans | Neue Nitro-p-phenylendiaminderivate, Verfahren zu ihrer Herstellung sowie Färbemittel für keratinische Fasern, die diese enthalten |
| US5260488A (en) * | 1991-09-13 | 1993-11-09 | Clairol Inc. | N1 -trifluoroalkyl substituted 2-nitro-p-phenylenediamine dyes |
| FR2687570A1 (fr) * | 1992-02-21 | 1993-08-27 | Oreal | Composition cosmetique a base d'agents tensio-actifs non-ioniques et de polymeres substantifs cationiques ou amphoteres et son utilisation comme support de teinture ou de decoloration. |
| DE4206416A1 (de) * | 1992-02-29 | 1993-09-02 | Wella Ag | Mittel zur oxidativen faerbung von haaren und neue 5-halogen-2,4-bis(alkylamino)-1-alkylbenzole |
| DE19728143A1 (de) * | 1996-07-03 | 1998-01-08 | Schwarzkopf Gmbh Hans | Färbemittel |
| JP4642976B2 (ja) * | 2000-07-14 | 2011-03-02 | ホーユー株式会社 | 酸化染毛剤組成物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2087689A (en) * | 1934-11-24 | 1937-07-20 | Firm Of Chemical Works | 2.4-dinitro-3.6-dihalogenanilines and a process for their manufacture |
| FR798141A (fr) * | 1934-11-24 | 1936-05-09 | Prod Chim Fab De | 2.4-dinitro-3.6-dihalogénanilines et procédé de préparation de ces corps |
| US2621175A (en) * | 1950-02-02 | 1952-12-09 | Merck & Co Inc | 6,7-dichloro-9-(1'-d-sorbityl)-isoalloxazine |
| AT226679B (de) * | 1961-02-24 | 1963-04-10 | Siegfried Ag | Verfahren zur Herstellung von neuen o-Phenylendiaminen |
| NL130871C (en, 2012) * | 1965-07-30 | |||
| US4018556A (en) * | 1965-12-03 | 1977-04-19 | Societe Anonyme Dite: L'oreal | Hair dye compounds |
| US3904690A (en) * | 1965-12-03 | 1975-09-09 | Oreal | 2-Nitro-meta-phenylenediamines |
| LU49990A1 (en, 2012) * | 1965-12-03 | 1967-06-05 | ||
| CH468188A (fr) * | 1966-02-15 | 1969-02-15 | Oreal | Procédé de teinture décolorante pour cheveux et composition tinctoriale pour la mise en oeuvre dudit procédé |
| DE1569662B1 (de) * | 1966-10-06 | 1970-06-04 | Basf Ag | Verfahren zur Herstellung von wasserunloeslichen Farbstoffen |
| US3743678A (en) * | 1968-02-28 | 1973-07-03 | Clairol Inc | Hair dyeing compositions |
| GB1286738A (en) * | 1970-10-20 | 1972-08-23 | United States Borax Chem | Substituted 1,3-phenylenediamine herbicides |
| CH609959A5 (en, 2012) * | 1976-12-17 | 1979-03-30 | Basf Ag | |
| FR2506303A1 (fr) * | 1981-05-25 | 1982-11-26 | Oreal | Nouvelles nitro-paraphenylenediamines chlorees, leur procede de preparation et leur utilisation en teinture des fibres keratiniques |
| DE3323207A1 (de) * | 1983-06-28 | 1985-01-03 | Wella Ag, 6100 Darmstadt | 1,4-diamino-5-chlor-2-nitrobenzolderivate, verfahren zu ihrer herstellung und mittel zur faerbung von haaren |
| LU85098A1 (fr) * | 1983-11-21 | 1985-07-17 | Oreal | Composition tinotoriale pour fibres keratiniques renfermant au moins une nitro-2 paraphenylenediamine n-substituee cosolubilisee et procedes de teinture de fibres keratiniques correspondants |
-
1985
- 1985-06-10 LU LU85939A patent/LU85939A1/fr unknown
-
1986
- 1986-06-04 CH CH2260/86A patent/CH670086A5/fr not_active IP Right Cessation
- 1986-06-06 AT AT0154086A patent/AT401343B/de not_active IP Right Cessation
- 1986-06-07 DE DE3619227A patent/DE3619227C2/de not_active Expired - Lifetime
- 1986-06-09 BE BE0/216759A patent/BE904890A/fr not_active IP Right Cessation
- 1986-06-09 FR FR868608300A patent/FR2583044B1/fr not_active Expired - Lifetime
- 1986-06-10 US US06/872,401 patent/US4666453A/en not_active Expired - Lifetime
- 1986-06-10 IT IT67478/86A patent/IT1190586B/it active
- 1986-06-10 NL NL8601506A patent/NL194164C/nl not_active IP Right Cessation
- 1986-06-10 JP JP61132890A patent/JPH0639455B2/ja not_active Expired - Lifetime
- 1986-06-10 CA CA000511227A patent/CA1266488A1/fr active Granted
- 1986-06-10 GB GB8614063A patent/GB2176494B/en not_active Expired
-
1988
- 1988-12-22 GB GB888829963A patent/GB8829963D0/en active Pending
-
1989
- 1989-03-17 GB GB8906163A patent/GB2213820B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2176494A (en) | 1986-12-31 |
| GB2213820B (en) | 1989-11-29 |
| FR2583044A1 (fr) | 1986-12-12 |
| GB8829963D0 (en) | 1989-02-15 |
| AT401343B (de) | 1996-08-26 |
| NL194164B (nl) | 2001-04-02 |
| ATA154086A (de) | 1996-01-15 |
| IT8667478A0 (it) | 1986-06-10 |
| GB8614063D0 (en) | 1986-07-16 |
| IT8667478A1 (it) | 1987-12-10 |
| FR2583044B1 (fr) | 1990-01-12 |
| US4666453A (en) | 1987-05-19 |
| CH670086A5 (en, 2012) | 1989-05-12 |
| GB2176494B (en) | 1989-11-22 |
| CA1266488A1 (fr) | 1990-03-06 |
| BE904890A (fr) | 1986-12-09 |
| JPH0639455B2 (ja) | 1994-05-25 |
| DE3619227A1 (de) | 1986-12-11 |
| JPS61286352A (ja) | 1986-12-16 |
| GB2213820A (en) | 1989-08-23 |
| LU85939A1 (fr) | 1987-01-13 |
| GB8906163D0 (en) | 1989-05-04 |
| IT1190586B (it) | 1988-02-16 |
| CA1270854C (en, 2012) | 1990-06-26 |
| DE3619227C2 (de) | 2002-11-21 |
| NL8601506A (nl) | 1987-01-02 |
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