CH615096A5 - - Google Patents
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- Publication number
- CH615096A5 CH615096A5 CH820976A CH820976A CH615096A5 CH 615096 A5 CH615096 A5 CH 615096A5 CH 820976 A CH820976 A CH 820976A CH 820976 A CH820976 A CH 820976A CH 615096 A5 CH615096 A5 CH 615096A5
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- methyl
- composition according
- coupler
- sulfate
- Prior art date
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 39
- 229910021529 ammonia Inorganic materials 0.000 claims description 20
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 18
- 239000000975 dye Substances 0.000 claims description 15
- -1 arylsulfonamidoalkyl Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 12
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 5
- DQPBABKTKYNPMH-UHFFFAOYSA-M amino sulfate Chemical compound NOS([O-])(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-M 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- JBESLYPTBIFSNQ-UHFFFAOYSA-N 2-methoxy-3,5-dimethylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=C(C)C(N)=C(C)C=C1N JBESLYPTBIFSNQ-UHFFFAOYSA-N 0.000 claims description 2
- IETCWPPCZSNWTI-UHFFFAOYSA-N 2-methoxy-4-n-methylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC=C(N)C(OC)=C1 IETCWPPCZSNWTI-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
- CIDLHQAOJOCQDS-UHFFFAOYSA-N 4-amino-3-methylphenol;hydrobromide Chemical compound Br.CC1=CC(O)=CC=C1N CIDLHQAOJOCQDS-UHFFFAOYSA-N 0.000 claims description 2
- QMBFWTZVNXFXEV-UHFFFAOYSA-N 4-n,2-dimethylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC=C(N)C(C)=C1 QMBFWTZVNXFXEV-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
- AWDKQDCYEIIDKA-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CONC1=CC=C(N)C=C1 AWDKQDCYEIIDKA-UHFFFAOYSA-N 0.000 claims description 2
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 2
- 244000060011 Cocos nucifera Species 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002535 acidifier Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 230000003113 alkalizing effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- RWHNUWWUPZKDQP-UHFFFAOYSA-N hydron;pyridine-2,5-diamine;dichloride Chemical compound Cl.Cl.NC1=CC=C(N)N=C1 RWHNUWWUPZKDQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- FMEJKACEWHCCNV-UHFFFAOYSA-N methoxy hydrogen sulfate Chemical compound COOS(O)(=O)=O FMEJKACEWHCCNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 8
- 239000002453 shampoo Substances 0.000 claims 2
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 claims 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims 1
- BUEFNCLNVXCFFS-UHFFFAOYSA-N 4-(2-piperidin-1-ylethyl)aniline Chemical compound C1=CC(N)=CC=C1CCN1CCCCC1 BUEFNCLNVXCFFS-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 238000000862 absorption spectrum Methods 0.000 claims 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000008135 aqueous vehicle Substances 0.000 claims 1
- 239000002610 basifying agent Substances 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 229960001484 edetic acid Drugs 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000265 homogenisation Methods 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 125000004964 sulfoalkyl group Chemical group 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- QKMNFFSBZRGHDJ-UHFFFAOYSA-N 1,4-dichloro-2-methoxybenzene Chemical compound COC1=CC(Cl)=CC=C1Cl QKMNFFSBZRGHDJ-UHFFFAOYSA-N 0.000 description 2
- SAUYCNWXEOCLNC-UHFFFAOYSA-N 2-(4-aminophenyl)ethanesulfonic acid Chemical compound NC1=CC=C(CCS(O)(=O)=O)C=C1 SAUYCNWXEOCLNC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IAEDWDXMFDKWFU-UHFFFAOYSA-N (4-azaniumylphenyl)-dimethylazanium;dichloride Chemical compound Cl.Cl.CN(C)C1=CC=C(N)C=C1 IAEDWDXMFDKWFU-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PDBSRMMSASAGJJ-UHFFFAOYSA-N 2-(4-amino-2-methoxyanilino)acetamide Chemical compound COC1=CC(N)=CC=C1NCC(N)=O PDBSRMMSASAGJJ-UHFFFAOYSA-N 0.000 description 1
- MAUAYDDABCDBRG-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC(N)=C(C)C=C1N MAUAYDDABCDBRG-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- RFJVQGMBFQGZPV-UHFFFAOYSA-N 4-amino-3-chlorophenol;hydrochloride Chemical compound Cl.NC1=CC=C(O)C=C1Cl RFJVQGMBFQGZPV-UHFFFAOYSA-N 0.000 description 1
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 1
- BXCWUHLEFQDLCY-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC=C(N)C=C1 BXCWUHLEFQDLCY-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- SKFFBLHFAMMHFE-UHFFFAOYSA-N anisole;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1 SKFFBLHFAMMHFE-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PAHPAZJFFVGVAB-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO.OO.OO.OO.OO PAHPAZJFFVGVAB-UHFFFAOYSA-N 0.000 description 1
- XEFRHJPGBKUEIN-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO.OO.OO.OO XEFRHJPGBKUEIN-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- JOWPOHZYWVVXGZ-UHFFFAOYSA-N n-(2-anilinoethyl)acetamide Chemical compound CC(=O)NCCNC1=CC=CC=C1 JOWPOHZYWVVXGZ-UHFFFAOYSA-N 0.000 description 1
- UOZQNVWSYKGFFU-UHFFFAOYSA-N n-(3-aminophenyl)nitramide Chemical compound NC1=CC=CC(N[N+]([O-])=O)=C1 UOZQNVWSYKGFFU-UHFFFAOYSA-N 0.000 description 1
- OXHJCNSXYDSOFN-UHFFFAOYSA-N n-hexylaniline Chemical compound CCCCCCNC1=CC=CC=C1 OXHJCNSXYDSOFN-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent 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
- A61K8/415—Aminophenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7520154A FR2315255A1 (fr) | 1975-06-26 | 1975-06-26 | Coupleurs glycoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615096A5 true CH615096A5 (en, 2012) | 1980-01-15 |
Family
ID=9157133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH820976A CH615096A5 (en, 2012) | 1975-06-26 | 1976-06-25 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4065255A (en, 2012) |
| JP (1) | JPS527450A (en, 2012) |
| AT (1) | AT352287B (en, 2012) |
| AU (1) | AU504384B2 (en, 2012) |
| BE (1) | BE843418A (en, 2012) |
| CA (1) | CA1077397A (en, 2012) |
| CH (1) | CH615096A5 (en, 2012) |
| DE (1) | DE2628641C3 (en, 2012) |
| FR (1) | FR2315255A1 (en, 2012) |
| GB (1) | GB1513704A (en, 2012) |
| IT (1) | IT1068733B (en, 2012) |
| NL (1) | NL179541C (en, 2012) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2628999C2 (de) * | 1976-06-28 | 1987-03-26 | Henkel KGaA, 4000 Düsseldorf | Haarfärbemittel |
| DE2924089C2 (de) * | 1979-06-15 | 1987-04-02 | Henkel KGaA, 4000 Düsseldorf | Dichlor-hydroxyethylaminophenole, deren Herstellung sowie diese bzw. deren Salze enthaltende Haarfärbemittel |
| DE2951377A1 (de) * | 1979-12-20 | 1981-07-02 | Wella Ag, 6100 Darmstadt | Mittel zum faerben von haaren |
| DE3016008A1 (de) * | 1980-04-25 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Neue kupplerkomponenten fuer oxidationshaarfarben, deren herstellung und verwendung, sowie diese enthaltende haarfaerbemittel |
| DE3413693A1 (de) * | 1984-04-11 | 1985-10-17 | Boehringer Mannheim Gmbh, 6800 Mannheim | Fluorierte anilinderivate und ihre verwendung |
| FR2571364B1 (fr) * | 1984-10-09 | 1987-07-17 | Oreal | Nouveau procede de preparation de nitroparaphenylenediamines n,n'-disubstituees, nouvelles oxazolidones utilisees dans ce procede, nouvelles nitroparaphenylenediamines n,n'-disubstituees obtenues selon ce procede et compositions tinctoriales contenant les nitroparaphenylenediamines n,n'-disubstituees obtenues selon ledit procede |
| DE3524329A1 (de) * | 1985-07-08 | 1987-01-08 | Henkel Kgaa | Neue aminophenole und deren verwendung in oxidationshaarfaerbemitteln |
| DE3610396A1 (de) * | 1986-03-27 | 1987-10-01 | Wella Ag | Mittel und verfahren zur oxidativen faerbung von haaren |
| JPH0294201U (en, 2012) * | 1989-01-10 | 1990-07-26 | ||
| US5183941A (en) * | 1989-05-18 | 1993-02-02 | Clairol Incorporated | Hair dye coupler compounds |
| US5073173A (en) * | 1990-05-18 | 1991-12-17 | Clairol Incorporated | Dye couplers |
| KR100276113B1 (ko) * | 1992-05-15 | 2000-12-15 | 죤엠.산드레 | 가속 초임계 유체 추출법 |
| US5344463A (en) | 1993-05-17 | 1994-09-06 | Clairol, Inc. | Hair dye compositions and methods utilizing 2-substituted-1-naphthol couplers |
| US5703266A (en) * | 1993-05-25 | 1997-12-30 | L'oreal | 3-substituted para-aminophenols |
| FR2706297B1 (fr) * | 1993-06-16 | 1995-08-18 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un paraaminophénol, un méta-aminophénol et un ortho-aminophénol, et procédé de teinture utilisant une telle composition. |
| FR2707488B1 (fr) * | 1993-07-13 | 1995-09-22 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un para-aminophénol, un méta-aminophénol et une paraphénylènediamine et/ou une bis-phénylalkylènediamine. |
| FR2707487B1 (fr) * | 1993-07-13 | 1995-09-08 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un para-aminophénol, un méta-aminophénol et une métaphénylènediamine, et procédé de teinture utilisant une telle composition. |
| FR2707489B1 (fr) * | 1993-07-13 | 1995-09-22 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un para-aminophénol, le 2-méthyl 5-aminophénol et une paraphénylènediamine et/ou une bis-phénylalkylènediamine. |
| FR2713928B1 (fr) * | 1993-12-22 | 1996-01-19 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un 3-fluoroparaaminophénol, un métaaminophénol et/ou une métaphénylène diamine et procédé de teinture utilisant une telle composition. |
| FR2715297B1 (fr) * | 1994-01-24 | 1996-02-23 | Oreal | Composition de teinture d'oxydation des fibres kératiniques comprenant un dérivé de paraphénylènediamine et un dérivé de métaaminophénol, et procédé de teinture utilisant une telle composition. |
| DE4421032A1 (de) * | 1994-06-16 | 1995-12-21 | Henkel Kgaa | Oxidationshaarfärbemittel in Gel-Form |
| FR2769212B1 (fr) * | 1997-10-03 | 2000-02-11 | Oreal | Composition de teinture des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| FR2769211B1 (fr) * | 1997-10-03 | 1999-12-24 | Oreal | Composition de teinture des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| DE19751777A1 (de) * | 1997-11-21 | 1999-05-27 | Wella Ag | Verfahren zur Herstellung von 5-((2-Hydroxyethyl)-amino)-2-methylphenol-sulfat und 5-((2-Hydroxyethyl)-amino)-2-methylphenol |
| FR2786093B1 (fr) * | 1998-11-20 | 2002-11-29 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| US6040482A (en) * | 1999-03-05 | 2000-03-21 | Milliken & Company | Oxyalkylene-substituted aminophenol intermediate |
| US6540793B1 (en) * | 2000-02-01 | 2003-04-01 | Clairol Incorporated | Coupler for use in oxidative hair dyeing |
| US6200353B1 (en) | 2000-02-01 | 2001-03-13 | Bristol Myers Squibb Company | Coupler for use in oxidative hair dyeing |
| MXPA03004379A (es) * | 2000-11-17 | 2005-01-25 | P & G Clariol Inc | Nuevo acoplador para usarse en la tincion oxidativa del cabello. |
| JP2004513907A (ja) * | 2000-11-17 | 2004-05-13 | ピーアンドジー−クレイロール・インコーポレイテッド | 酸化毛髪染色において使用する新規のカップラー |
| MXPA03004378A (es) | 2000-11-17 | 2005-01-25 | P & G Clariol Inc | Acoplador novedoso para utilizarse en el tenido oxidativo del cabello. |
| EP1333794A4 (en) * | 2000-11-17 | 2005-08-10 | P & G Clairol Inc | NOVEL COUPLING AGENT TO BE USED FOR OXIDIZING HAIR COLORING |
| US6409773B1 (en) | 2000-12-14 | 2002-06-25 | Clairol Incorporated | Coupler for use in oxidative hair dyeing |
| US7097668B2 (en) * | 2002-09-16 | 2006-08-29 | Combe Incorporated | Temporary hair dye composition |
| JP5324298B2 (ja) * | 2009-04-15 | 2013-10-23 | 昭和化学工業株式会社 | ヒドロキシアルキルアミノフェノール誘導体の製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL284202A (en, 2012) * | 1961-10-26 | 1900-01-01 | ||
| BE625116A (en, 2012) * | 1961-11-22 | |||
| US3415608A (en) * | 1968-01-26 | 1968-12-10 | Lowenstein Dyes & Cosmetics In | Stabilized oxidation dye compositions |
| LU56722A1 (en, 2012) * | 1968-08-14 | 1970-02-16 | ||
| LU59063A1 (en, 2012) * | 1969-07-08 | 1971-03-09 | ||
| US3834866A (en) * | 1972-04-04 | 1974-09-10 | Alberto Culver Co | Oxidation dye compositions containing 5-aminoguaiacols as couplers |
| US3893803A (en) * | 1972-10-10 | 1975-07-08 | Procter & Gamble | Hair dyeing premixes containing peroxidase enzymes stabilized with heme complexing agents |
| US3981677A (en) | 1974-01-02 | 1976-09-21 | Clairol Incorporated | Oxidative hair dye compositions containing N-substituted o-phenylenediamines and method for their use |
-
1975
- 1975-06-26 FR FR7520154A patent/FR2315255A1/fr active Granted
-
1976
- 1976-06-23 US US05/699,169 patent/US4065255A/en not_active Expired - Lifetime
- 1976-06-25 BE BE168320A patent/BE843418A/xx not_active IP Right Cessation
- 1976-06-25 CA CA255,713A patent/CA1077397A/fr not_active Expired
- 1976-06-25 DE DE2628641A patent/DE2628641C3/de not_active Expired
- 1976-06-25 CH CH820976A patent/CH615096A5/fr not_active IP Right Cessation
- 1976-06-25 AT AT467476A patent/AT352287B/de not_active IP Right Cessation
- 1976-06-25 NL NLAANVRAGE7606950,A patent/NL179541C/xx not_active IP Right Cessation
- 1976-06-25 AU AU15302/76A patent/AU504384B2/en not_active Expired
- 1976-06-25 JP JP51075409A patent/JPS527450A/ja active Granted
- 1976-06-25 IT IT68574/76A patent/IT1068733B/it active
- 1976-06-25 GB GB26590/76A patent/GB1513704A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2628641B2 (de) | 1980-12-04 |
| US4065255A (en) | 1977-12-27 |
| JPS6133801B2 (en, 2012) | 1986-08-04 |
| FR2315255B1 (en, 2012) | 1980-04-18 |
| JPS527450A (en) | 1977-01-20 |
| AU1530276A (en) | 1978-01-05 |
| IT1068733B (it) | 1985-03-21 |
| AU504384B2 (en) | 1979-10-11 |
| AT352287B (de) | 1979-09-10 |
| DE2628641A1 (de) | 1977-01-13 |
| GB1513704A (en) | 1978-06-07 |
| FR2315255A1 (fr) | 1977-01-21 |
| NL7606950A (nl) | 1976-12-28 |
| NL179541C (nl) | 1986-10-01 |
| DE2628641C3 (de) | 1981-08-13 |
| ATA467476A (de) | 1979-02-15 |
| BE843418A (fr) | 1976-12-27 |
| CA1077397A (fr) | 1980-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |