LU86904A1 - Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions - Google Patents
Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions Download PDFInfo
- Publication number
- LU86904A1 LU86904A1 LU86904A LU86904A LU86904A1 LU 86904 A1 LU86904 A1 LU 86904A1 LU 86904 A LU86904 A LU 86904A LU 86904 A LU86904 A LU 86904A LU 86904 A1 LU86904 A1 LU 86904A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- amino
- dye composition
- composition according
- aniline
- ethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 150000001875 compounds Chemical class 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 25
- 230000003647 oxidation Effects 0.000 title claims abstract description 23
- 238000004043 dyeing Methods 0.000 title claims abstract description 19
- 239000000835 fiber Substances 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000000975 dye Substances 0.000 claims description 63
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 52
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- -1 alkyl radical Chemical class 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 239000002243 precursor Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 102000011782 Keratins Human genes 0.000 claims description 12
- 108010076876 Keratins Proteins 0.000 claims description 12
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- DWAGDHCKFIRKDO-UHFFFAOYSA-N NC1=C(C(=CC=C1OC)Cl)OC Chemical compound NC1=C(C(=CC=C1OC)Cl)OC DWAGDHCKFIRKDO-UHFFFAOYSA-N 0.000 claims description 6
- GPCCOYMAIQOSPF-UHFFFAOYSA-N 5-chloro-2,4-dimethoxybenzene-1,3-diamine Chemical compound COC1=C(N)C=C(Cl)C(OC)=C1N GPCCOYMAIQOSPF-UHFFFAOYSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- SXJQUUPSLJTKKT-UHFFFAOYSA-N 4-hydroxy-2-methoxyaniline Natural products COC1=CC(O)=CC=C1N SXJQUUPSLJTKKT-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 claims description 2
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 claims description 2
- UBKPLLYABUUFCE-UHFFFAOYSA-N 4-amino-2,3-dimethylphenol Chemical compound CC1=C(C)C(O)=CC=C1N UBKPLLYABUUFCE-UHFFFAOYSA-N 0.000 claims description 2
- JSWVCUXQICMATE-UHFFFAOYSA-N 4-amino-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C=C1N JSWVCUXQICMATE-UHFFFAOYSA-N 0.000 claims description 2
- OMVFXCQLSCPJNR-UHFFFAOYSA-N 4-amino-2,6-dimethylphenol Chemical compound CC1=CC(N)=CC(C)=C1O OMVFXCQLSCPJNR-UHFFFAOYSA-N 0.000 claims description 2
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 claims description 2
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
- PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 claims description 2
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 claims description 2
- YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 claims description 2
- GDOIKKMNCIMDAO-UHFFFAOYSA-N 5-amino-1h-pyridin-2-one Chemical compound NC1=CC=C(O)N=C1 GDOIKKMNCIMDAO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000000982 direct dye Substances 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000035515 penetration Effects 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003380 propellant Substances 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims description 2
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims 2
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 claims 1
- YFZNTUOMAQXCQZ-UHFFFAOYSA-N 4-n-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(N)C=C1 YFZNTUOMAQXCQZ-UHFFFAOYSA-N 0.000 claims 1
- RCZAPWMTLKZMNH-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-1-n-methylbenzene-1,3-diamine Chemical compound CNC1=CC(Cl)=C(OC)C(N)=C1OC RCZAPWMTLKZMNH-UHFFFAOYSA-N 0.000 claims 1
- PBVMEWIPMBMMGX-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-3-n-methylbenzene-1,3-diamine Chemical compound CNC1=C(OC)C(N)=CC(Cl)=C1OC PBVMEWIPMBMMGX-UHFFFAOYSA-N 0.000 claims 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-ethyl-N-phenylamine Natural products CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical class C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002610 basifying agent Substances 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 239000000118 hair dye Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- XAXXXFOWCPSWLO-UHFFFAOYSA-N 3-n-chlorobenzene-1,3-diamine Chemical class NC1=CC=CC(NCl)=C1 XAXXXFOWCPSWLO-UHFFFAOYSA-N 0.000 abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- 239000000047 product Substances 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000012429 reaction media Substances 0.000 description 18
- 238000007792 addition Methods 0.000 description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 8
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000010802 sludge Substances 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000223 polyglycerol Polymers 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PXYFKGIRWVWHRV-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-3-nitroaniline Chemical compound COC1=C(N)C=C(Cl)C(OC)=C1[N+]([O-])=O PXYFKGIRWVWHRV-UHFFFAOYSA-N 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- 239000012256 powdered iron Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 3
- WSZUAGXEGAISLM-UHFFFAOYSA-N 1-chloro-2,4-dimethoxy-3,5-dinitrobenzene Chemical compound COC1=C(Cl)C=C([N+]([O-])=O)C(OC)=C1[N+]([O-])=O WSZUAGXEGAISLM-UHFFFAOYSA-N 0.000 description 2
- GPJJASIJVRXZFI-UHFFFAOYSA-N 4-methoxybenzene-1,3-diol Chemical compound COC1=CC=C(O)C=C1O GPJJASIJVRXZFI-UHFFFAOYSA-N 0.000 description 2
- KVZDSNIWXQNBBS-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-n-methyl-3-nitroaniline Chemical compound CNC1=CC(Cl)=C(OC)C([N+]([O-])=O)=C1OC KVZDSNIWXQNBBS-UHFFFAOYSA-N 0.000 description 2
- 241000640882 Condea Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 2
- OFMRACCIIIDSDN-UHFFFAOYSA-N 1,2,4-trichloro-3,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C([N+]([O-])=O)=C1Cl OFMRACCIIIDSDN-UHFFFAOYSA-N 0.000 description 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- FVMMDDSAOLYJGM-UHFFFAOYSA-N 1-amino-1-(4-aminophenoxy)ethanol Chemical compound NC(C)(O)OC1=CC=C(C=C1)N FVMMDDSAOLYJGM-UHFFFAOYSA-N 0.000 description 1
- WEJYCHRHCANQLH-UHFFFAOYSA-N 1-chloro-2,3-dimethoxybenzene dihydrochloride Chemical compound COC1=C(C(=CC=C1)Cl)OC.Cl.Cl WEJYCHRHCANQLH-UHFFFAOYSA-N 0.000 description 1
- OACCRGFGCIQFNR-UHFFFAOYSA-N 1-chloro-2,4-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C(OC)=C1 OACCRGFGCIQFNR-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- LIJLYNWYKULUHA-UHFFFAOYSA-N 2-chloroethyl carbamate Chemical compound NC(=O)OCCCl LIJLYNWYKULUHA-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-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
- XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BNRMHEDSMWOIMC-UHFFFAOYSA-N 4-(2-aminoethoxy)benzene-1,3-diamine Chemical compound NCCOC1=CC=C(N)C=C1N BNRMHEDSMWOIMC-UHFFFAOYSA-N 0.000 description 1
- MCNBYOWWTITHIG-UHFFFAOYSA-N 4-amino-2-methoxyphenol Chemical compound COC1=CC(N)=CC=C1O MCNBYOWWTITHIG-UHFFFAOYSA-N 0.000 description 1
- BZWJOZNPOSYQTJ-UHFFFAOYSA-N 4-amino-3-methylbenzene-1,2-diol Chemical compound CC1=C(N)C=CC(O)=C1O BZWJOZNPOSYQTJ-UHFFFAOYSA-N 0.000 description 1
- GCWYXRHXGLFVFE-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylaniline Chemical compound CC1=CC(O)=CC(C)=C1N GCWYXRHXGLFVFE-UHFFFAOYSA-N 0.000 description 1
- IHWPTLPROWODBQ-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine Chemical compound CONC1=CC=C(N)C=C1 IHWPTLPROWODBQ-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
- NCJXWADUPNGWQK-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-1-n-methylbenzene-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC(Cl)=C(OC)C(N)=C1OC NCJXWADUPNGWQK-UHFFFAOYSA-N 0.000 description 1
- GBBDSAVMEZPFCN-UHFFFAOYSA-N 5-chloro-2,4-dimethoxybenzene-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=C(N)C=C(Cl)C(OC)=C1N GBBDSAVMEZPFCN-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000928106 Alain Species 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 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 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 101150034459 Parpbp gene Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- BMJXMAAIWXBKBD-UHFFFAOYSA-N aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1 BMJXMAAIWXBKBD-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 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
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- XILYOLONIFWGMT-UHFFFAOYSA-N benzene;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC=C1 XILYOLONIFWGMT-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- JGDMWJXFSAHEKS-UHFFFAOYSA-N chlorobenzene;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=CC=C1 JGDMWJXFSAHEKS-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 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 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- MLOKBPBARNTXBM-UHFFFAOYSA-N n-(3-amino-5-chloro-2,4-dimethoxyphenyl)acetamide Chemical compound COC1=C(Cl)C=C(NC(C)=O)C(OC)=C1N MLOKBPBARNTXBM-UHFFFAOYSA-N 0.000 description 1
- XPGXSWPADIZALV-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxy-3-nitrophenyl)acetamide Chemical compound COC1=C(Cl)C=C(NC(C)=O)C(OC)=C1[N+]([O-])=O XPGXSWPADIZALV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 208000003383 pontocerebellar hypoplasia type 3 Diseases 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PVTQTOGPOPGQGE-SAMSIYEGSA-N prostaglandin H3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O PVTQTOGPOPGQGE-SAMSIYEGSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- QGLITUFXHVRMGV-UHFFFAOYSA-M sodium;tetratriacontyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOS([O-])(=O)=O QGLITUFXHVRMGV-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 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 Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 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
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86904A LU86904A1 (fr) | 1987-05-29 | 1987-05-29 | Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions |
| EP88108493A EP0295474B1 (de) | 1987-05-29 | 1988-05-27 | Clorometaphenylendiamine, deren Verwendung als Kuppler für die oxidative Färbung von Keratinfasern, Haarfärbezusammensetzungen, die diese Verbindungen enthalten und Färbeverfahren mit diesen Zusammensetzungen |
| JP63130029A JP2551628B2 (ja) | 1987-05-29 | 1988-05-27 | フエニレンジアミン化合物および染毛組成物 |
| AT88108493T ATE65241T1 (de) | 1987-05-29 | 1988-05-27 | Clorometaphenylendiamine, deren verwendung als kuppler fuer die oxidative faerbung von keratinfasern, haarfaerbezusammensetzungen, die diese verbindungen enthalten und faerbeverfahren mit diesen zusammensetzungen. |
| ES88108493T ES2022950B3 (es) | 1987-05-29 | 1988-05-27 | Nuevas clorometafenilenodiaminas, su utilizacion como acopladoras en tintura de oxidacion de fibras queratinicas, composiciones de tintura para cabellos que contienen estos compuestos y proceso de tinte utilizando dichas composiciones |
| DE8888108493T DE3863700D1 (de) | 1987-05-29 | 1988-05-27 | Clorometaphenylendiamine, deren verwendung als kuppler fuer die oxidative faerbung von keratinfasern, haarfaerbezusammensetzungen, die diese verbindungen enthalten und faerbeverfahren mit diesen zusammensetzungen. |
| CA000568076A CA1314564C (fr) | 1987-05-29 | 1988-05-30 | Chlorometaphenylenediamines, leur utilisation en tant que coupleurs en teinture d'oxydation des fibres keratiniques, compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions |
| US07/200,399 US4865618A (en) | 1987-05-29 | 1988-05-31 | New chloro-meta-phenylenediamines, their use as couplers in the oxidation dyeing of keratinous fibres, dyeing compositions for hair containing these compounds and dyeing process using the said |
| US07/566,109 USRE34300E (en) | 1987-05-29 | 1990-08-13 | Chloro-meta-phenylenediamines, their use as couplers in the oxidation dyeing of keratinous fibres, dyeing compositions for hair containing these compounds and dyeing process using the said compositions |
| GR91400935T GR3002325T3 (en) | 1987-05-29 | 1991-07-18 | Chlorometaphenylenediamines, their use as coupling agents in oxydation colouring of keratinic fibres, colourity compositions for hair containing these compounds and colouring process using these compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86904 | 1987-05-29 | ||
| LU86904A LU86904A1 (fr) | 1987-05-29 | 1987-05-29 | Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU86904A1 true LU86904A1 (fr) | 1989-01-19 |
Family
ID=19730933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU86904A LU86904A1 (fr) | 1987-05-29 | 1987-05-29 | Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4865618A (de) |
| EP (1) | EP0295474B1 (de) |
| JP (1) | JP2551628B2 (de) |
| AT (1) | ATE65241T1 (de) |
| CA (1) | CA1314564C (de) |
| DE (1) | DE3863700D1 (de) |
| ES (1) | ES2022950B3 (de) |
| GR (1) | GR3002325T3 (de) |
| LU (1) | LU86904A1 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU86905A1 (fr) * | 1987-05-29 | 1989-01-19 | Oreal | Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains |
| FR2628104B1 (fr) * | 1988-03-03 | 1990-07-27 | Oreal | Para-aminophenols 3-substitues, leur procede de preparation, leur utilisation pour la teinture des fibres keratiniques et les composes intermediaires utilises dans le procede de preparation |
| LU87396A1 (fr) * | 1988-11-22 | 1990-06-12 | Oreal | Nouvelles metaphenylenediamines trialcoxy-substituees,leur procede de preparation,et leur utilisation en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains |
| US5206349A (en) * | 1990-08-10 | 1993-04-27 | Toyo Gosei Kogy Co., Ltd. | Aromatic diazo compounds and photosensitive compositions using the same |
| US5192333A (en) * | 1990-09-04 | 1993-03-09 | Combe Incorporated | Aqueous progressive hair colorant having soluble sulfur source and amphoteric surfactant |
| 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. |
| DE4342009C2 (de) * | 1993-12-09 | 1996-05-23 | Goldwell Gmbh | Haarfärbemittel |
| CA2181797A1 (en) * | 1994-01-25 | 1995-07-27 | Jeffrey John Scheibel | Polyhydroxy diamines and their use in detergent compositions |
| US7190491B2 (en) * | 1999-05-25 | 2007-03-13 | Silverbrook Research Pty Ltd | Interactive publication printer and binder |
| US7170499B1 (en) * | 1999-05-25 | 2007-01-30 | Silverbrook Research Pty Ltd | Handwritten text capture via interface surface |
| DE10245426A1 (de) * | 2002-09-27 | 2004-04-08 | Henkel Kgaa | Neue Kupplerkomponenten |
| JP2010534657A (ja) * | 2007-07-27 | 2010-11-11 | クローダ，インコーポレイティド | ポリマーのカチオン性化合物堆積助剤としてのリン含有界面活性剤 |
| PL2968092T3 (pl) | 2013-03-15 | 2020-11-16 | Croda, Inc. | Etery alkilowe alkoksylowanych alkoholi tłuszczowych i produkty je zawierające |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3137473A1 (de) * | 1981-09-21 | 1983-04-07 | Henkel KGaA, 4000 Düsseldorf | "n-substituierte 2.4-diamino-m-xylole und diese enthaltende haarfaerbemittel" |
| US4566876A (en) * | 1983-03-10 | 1986-01-28 | Clairol Incorporated | Meta-phenylenediamine coupler compounds and oxidative hair dye compositions and methods using same |
-
1987
- 1987-05-29 LU LU86904A patent/LU86904A1/fr unknown
-
1988
- 1988-05-27 JP JP63130029A patent/JP2551628B2/ja not_active Expired - Lifetime
- 1988-05-27 ES ES88108493T patent/ES2022950B3/es not_active Expired - Lifetime
- 1988-05-27 AT AT88108493T patent/ATE65241T1/de not_active IP Right Cessation
- 1988-05-27 DE DE8888108493T patent/DE3863700D1/de not_active Expired - Lifetime
- 1988-05-27 EP EP88108493A patent/EP0295474B1/de not_active Expired - Lifetime
- 1988-05-30 CA CA000568076A patent/CA1314564C/fr not_active Expired - Fee Related
- 1988-05-31 US US07/200,399 patent/US4865618A/en not_active Ceased
-
1990
- 1990-08-13 US US07/566,109 patent/USRE34300E/en not_active Expired - Lifetime
-
1991
- 1991-07-18 GR GR91400935T patent/GR3002325T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4865618A (en) | 1989-09-12 |
| EP0295474A1 (de) | 1988-12-21 |
| JPS6463509A (en) | 1989-03-09 |
| GR3002325T3 (en) | 1992-12-30 |
| DE3863700D1 (de) | 1991-08-22 |
| EP0295474B1 (de) | 1991-07-17 |
| ATE65241T1 (de) | 1991-08-15 |
| USRE34300E (en) | 1993-07-06 |
| CA1314564C (fr) | 1993-03-16 |
| ES2022950B3 (es) | 1991-12-16 |
| JP2551628B2 (ja) | 1996-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1306952C (fr) | Utilisation comme coupleur du 2,4-diamino-1,3-dimethoxybenzene ou l'un de ses sels, en association avec des precurseurs de colorants d'oxydation, pour la teinture des cheveux humains, composition de teinture capillairecontenant ledit coupleur et procede de preparation dudit coupleur | |
| EP0591373B1 (de) | Meta-aminophenolen,verwendung als kupplungen für oxydationsfarbstoffe für keratinische fäser, zusammensetzungen und farbenprozessen | |
| CA1327975C (fr) | Para-aminophenols 3-substitues, leur procede de preparation, leur utilisation pour la teinture des fibres keratiniques et les composes intermediaires utilises dans le procede de preparation | |
| EP0294669B1 (de) | Metaphenylendiamine, Verfahren zu deren Herstellung, Zwischenprodukte und Verwendung dieser Metaphenylendiamine als Kuppler für die oxidative Färbung von Keratinfasern insbesondere von menschlichem Haar | |
| FR2630438A1 (fr) | Nouvelles p-phenylenediamines, leur procede de preparation, composition tinctoriale les contenant et procede de teinture correspondant | |
| CA1341194C (fr) | Composition de teinture de fibre keratinique contenant des bases d'oxydation dites "doubles" et des bases d'oxydation dites "simples", et procede de teinture la mettant en oeuvre | |
| LU86904A1 (fr) | Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions | |
| FR2547300A1 (fr) | Nouveaux metaaminophenols substitues, leur procede de preparation, compositions tinctoriales pour cheveux les contenant et procede de teinture de cheveux correspondant | |
| CA1305184C (fr) | 2-nitro metaphenylene-diamines substituees, leur procede de preparation et leurutilisation en teinture des fibres keratiniques et en particulier des cheveux humains | |
| EP0359618B1 (de) | 2-Substituierte Paraaminophenole und ihre Verwendung für die Färbung von keratinischen Fasern | |
| CA1182130A (fr) | Colorants nitres, leur procede de preparation, composes intermediaires utilises pour leur preparation et utilisation de ces colorants en teinture des fibres keratiniques | |
| EP0366542B1 (de) | 5-Substituierte Ortho-Aminophenole, Verfahren zu ihrer Herstellung und ihre Verwendung als Oxydationsfärbemittel von keratinischen Fasern | |
| FR2579103A1 (fr) | Utilisation de 4,5-methylenedioxyphenol halogene dans la teinture des fibres keratiniques | |
| LU87396A1 (fr) | Nouvelles metaphenylenediamines trialcoxy-substituees,leur procede de preparation,et leur utilisation en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains | |
| FR2566269A1 (fr) | Composition tinctoriale pour fibres keratiniques renfermant au moins une nitro-2 paraphenylenediamines n-substituee cosolubilisee et procedes de teinture de fibres keratiniques correspondants | |
| EP0589952B1 (de) | Verwendung von schwefelhaltigen meta-aminophenolen zum färben von keratinfasern, färbezusammensetzungen und neue verbindungen | |
| CA1305183C (fr) | 2,4-diamino-1,3,5-trimethoxybenzene, son procede de preparation et son utilisation comme coupleur dans les teintures d'oxydation pour fibres keratiniques | |
| FR2497662A1 (fr) | Composition tinctoriale pour fibres keratiniques a base de nitro-3 orthophenylenediamines, nouvelles nitro-3 orthophenylenediamines utilisees et leurs procedes de preparation | |
| CA1254908A (fr) | Nitro-2, amino-4,hydroxyalkyl-6 anilines, leur procede de preparation et leur utilisation en teinture des fibres keratiniques, et en particulier des cheveux humains | |
| CA1258681A (fr) | Amino-2, nitro-4,hydroxyalkyl-6 anilines, leur procede de preparation et leur utilisation en teintures des fibres keratiniques | |
| FR2569401A1 (fr) | Nouveaux derives dimethyles de nitro-3 amino-4 aniline, leur procede de preparation et leur utilisation en teinture des fibres keratiniques |