LU85681A1 - NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS AND IN PARTICULAR HUMAN HAIR - Google Patents
NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS AND IN PARTICULAR HUMAN HAIR Download PDFInfo
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- LU85681A1 LU85681A1 LU85681A LU85681A LU85681A1 LU 85681 A1 LU85681 A1 LU 85681A1 LU 85681 A LU85681 A LU 85681A LU 85681 A LU85681 A LU 85681A LU 85681 A1 LU85681 A1 LU 85681A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- formula
- compound
- nitro
- amino
- composition
- Prior art date
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- 239000000835 fiber Substances 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 15
- 238000004043 dyeing Methods 0.000 title claims description 13
- 150000001448 anilines Chemical class 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000000975 dye Substances 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- -1 alkylene radical Chemical class 0.000 claims description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- 102000011782 Keratins Human genes 0.000 claims description 12
- 108010076876 Keratins Proteins 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000982 direct dye Substances 0.000 claims description 4
- 238000009967 direct dyeing Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000002453 shampoo Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 150000002334 glycols Chemical class 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002535 acidifier Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- 238000007281 aminoalkylation reaction Methods 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 230000035515 penetration Effects 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 241000928106 Alain Species 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 238000004040 coloring Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 7
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 7
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- JURNNMWQCBIRJK-UHFFFAOYSA-N 2-amino-2-(3-amino-5-nitrophenyl)ethanol Chemical compound NC(CO)C1=CC(=CC(=C1)[N+](=O)[O-])N JURNNMWQCBIRJK-UHFFFAOYSA-N 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000005639 Lauric acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001348 alkyl chlorides Chemical class 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- OSVNQUBJWRJOER-UHFFFAOYSA-N 2-(9-methyldecyl)-5-(4-methylpentyl)benzene-1,3-diol Chemical compound CC(C)CCCCCCCCC1=C(O)C=C(CCCC(C)C)C=C1O OSVNQUBJWRJOER-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 2
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 229940116335 lauramide Drugs 0.000 description 2
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N n-(4-aminophenyl)nitramide Chemical class NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000001005 nitro dye Substances 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229920000223 polyglycerol Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VSKCCZIUZNTICH-ZPYUXNTASA-N (e)-but-2-enoic acid;ethenyl acetate Chemical compound C\C=C\C(O)=O.CC(=O)OC=C VSKCCZIUZNTICH-ZPYUXNTASA-N 0.000 description 1
- 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 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- UOOZFWHXYFFZCJ-UHFFFAOYSA-N 1-phenoxyethanol;dihydrochloride Chemical compound Cl.Cl.CC(O)OC1=CC=CC=C1 UOOZFWHXYFFZCJ-UHFFFAOYSA-N 0.000 description 1
- WYTRYIUQUDTGSX-UHFFFAOYSA-N 1-phenylpropan-2-ol Chemical compound CC(O)CC1=CC=CC=C1 WYTRYIUQUDTGSX-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- YCGBOLMHJWHYDM-UHFFFAOYSA-N 4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC2=C1CCC2 YCGBOLMHJWHYDM-UHFFFAOYSA-N 0.000 description 1
- BTJYWJVLRHNVAP-UHFFFAOYSA-N 5,6-dimethylbenzimidazol-1-amine Chemical compound C1=C(C)C(C)=CC2=C1N(N)C=N2 BTJYWJVLRHNVAP-UHFFFAOYSA-N 0.000 description 1
- DVTLVWPPECNISQ-UHFFFAOYSA-N 5,7-dinitro-1-benzofuran Chemical compound [N+](=O)([O-])C=1C=C(C2=C(C=CO2)C=1)[N+](=O)[O-] DVTLVWPPECNISQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-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
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- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 241000382928 Oxya Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000003973 alkyl amines 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VHFSMDHANDABQK-UHFFFAOYSA-N azane;2-sulfanylpropanoic acid Chemical compound [NH4+].CC(S)C([O-])=O VHFSMDHANDABQK-UHFFFAOYSA-N 0.000 description 1
- 239000002610 basifying agent 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
- 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N butyl vinyl ether Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 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
- 238000005266 casting Methods 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 229940093476 ethylene glycol Drugs 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
- 238000001914 filtration Methods 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
- 230000037308 hair color Effects 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 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
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 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
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012857 repacking 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
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000003981 vehicle Substances 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
Description
**
Nouvelles nitro-2,amino-4,hydroxyalkyl-6 anilines, leur procédé de préparation et leur utilisation en teinture des fibres kératiniques, et en particulier des cheveux humains.New nitro-2, amino-4, hydroxyalkyl-6 anilines, process for their preparation and their use in dyeing keratin fibers, and in particular human hair.
. 5 La présente invention est relative à de nouvelles nitro-2,amino-4, hydroxyalkyl-6 anilines, ä leur procédé de préparation et à leur utilisation en teinture des fibres kératiniques, et plus particulièrement des cheveux humains.. The present invention relates to new nitro-2, amino-4, hydroxyalkyl-6 anilines, to their preparation process and to their use in dyeing keratin fibers, and more particularly human hair.
Il est bien connu que, pour conférer aux cheveux une coloration 1Q. directe ou des reflets complémentaires dans le cas de la coloration d’oxydation, on peut utiliser les dérivés nitrés de la série benzénique.It is well known that to give hair 1Q coloring. direct or additional reflections in the case of oxidation coloring, the nitro derivatives of the benzene series can be used.
On a déjà préconisé l’utilisation de nitroparaphénylènediamines dont les atomes d’azote sont mono- ou disubstituës, tant en teinture directe qu’en teinture d’oxydation.The use of nitroparaphenylenediamines, the nitrogen atoms of which are mono- or disubstituted, has already been recommended, both in direct dyeing and in oxidation dyeing.
15 Malheureusement, on a constaté d’une manière générale, que ces nitroparaphénylènediamines possédaient une stabilité insuffisante aux intempéries et au lavage. La demanderesse a donc recherché de nouveaux colorants nitrés présentant une meilleure stabilité à la lumière et au lavage, et c’est ainsi qu’elle a découvert les nouveaux composés de 20 formule (I) :Unfortunately, it has generally been found that these nitroparaphenylenediamines have insufficient stability to weathering and washing. The Applicant therefore sought new nitro dyes having better light and washing stability, and this is how it discovered the new compounds of formula (I):
R2NH ^ X-OHR2NH ^ X-OH
| (I) ----NHR^ 25 N02 dans laquelle : X désigne un radical alkylène ramifié ou non, comportant 2 à 6 atomes de carbone, l’un de ces atomes pouvant être éventuellement substitué î. par un ou plusieurs radicaux hydroxyle; 30 et R2 désignent, indépendamment l’un de l’autre, un atome d'hydrogène, un radical alkyle, mono- ou polÿhydroxyalkyle ou aminoalkyle dont la fonction amine peut être mono- ou disubstituée par un radical alkyle ou mono- ou polyhydroxyalkyle, l’atome d’azote pouvant aussi faire partie d’un hétêrocycle, le radical alkyle comportant 1 à 4 atomes de carbone; 35 R’ désigne un atome d’hydrogène ou un radical alkyle en à C^.| (I) ---- NHR ^ 25 N02 in which: X denotes a branched or unbranched alkylene radical containing 2 to 6 carbon atoms, one of these atoms being possibly substituted. by one or more hydroxyl radicals; 30 and R2 denote, independently of one another, a hydrogen atom, an alkyl, mono- or polyhydroxyalkyl or aminoalkyl radical, the amine function of which can be mono- or disubstituted by an alkyl or mono- or polyhydroxyalkyl radical, the nitrogen atom can also be part of a heterocycle, the alkyl radical having 1 to 4 carbon atoms; 35 R ′ denotes a hydrogen atom or a C 1 -C 4 alkyl radical.
/ // 2 λ/ // 2 λ
La présente Invention a donc pour objet les nouvelles nitro-2, amino-4,hydroxyalkyl-6 anilines de formule (I) indiquée ci-dessus, ainsi que leurs sels cosmétiquement acceptables.The present invention therefore relates to the new nitro-2, amino-4, hydroxyalkyl-6 anilines of formula (I) indicated above, as well as their cosmetically acceptable salts.
A titre de radicaux X préférés, on peut citer les radicaux éthy-5 lène, propylène, diméthyl-1,1 éthylène, diméthyl-1,2 éthylène et tri- méthyl-1,1,2 éthylène.Mention may be made, as preferred X radicals, of 5-ethylene, propylene, 1,1-dimethyl ethylene, 1,2-dimethyl ethylene and tri-1,1,2 ethylene radicals.
- A titre de radicaux R^ et R£ plus particulièrement préférés selon l’invention, on peut citer l’hydrcgène, les radicaux méthyle, éthyle, n-propyle, ft> -hydroxyéthyle, ^-hydroxypropyle, , V^-dihydroxypropyle, 10 amlnoéthyle, |3-diéthylaminoéthyle.As radicals R ^ and R £ which are more particularly preferred according to the invention, mention may be made of hydrogenene, methyl, ethyl, n-propyl, ft> -hydroxyethyl, ^ -hydroxypropyl,, V ^ -dihydroxypropyle radicals, Aminoethyl, 3-diethylaminoethyl.
Les radicaux R’ préférés selon l’invention sont 1’hydrogène et le radical méthyle.The preferred radicals R ′ according to the invention are hydrogen and the methyl radical.
Des composés de formule (I) préférés selon l’invention sont : - le (diamino-2,5,nitro-3)phényl-2 éthanol-1; 15 - le (diamino-2,5,nitro-3)phényl-l propanol-2; - l’£amino-2,(^-hydroxyéthyl)amino-5,nitro-3)phényl-l propanol-2, , ainsi que leurs sels.Compounds of formula (I) preferred according to the invention are: - (2,5-diamino, 3-nitro) 2-phenyl-1-ethanol; - (diamino-2,5, nitro-3) phenyl-l propanol-2; - £ amino-2, (^ - hydroxyethyl) amino-5, nitro-3) phenyl-l propanol-2, as well as their salts.
La présente Invention a également pour objet un procédé de préparation des composés de formule (I).The present invention also relates to a process for the preparation of the compounds of formula (I).
20 Les nitro-2,amino-4 ,hydroxyalkyl-6 anilines de formule (I), selon l’invention, sont préparées selon un procédé qui consiste à faire réagir une solution aqueuse d'ammoniac sur un composé hétérocyclique de formule (IV) ci-après, puis à procéder à une réduction sélective de la dinitro- 2,4,hydroxyalkyl-6 aniline de formule (III) obtenue, pour obtenir une 25 nitro-2,amino-4,hydroxyalkyl-6 aniline de formule (II), qu’on soumet ensuite éventuellement à un procédé chimique classique d’alkylation, d’hydroxyalkylations ou d’aminoalkylation pour obtenir le composé final de formule (I) . .........-.......The nitro-2, amino-4, hydroxyalkyl-6 anilines of formula (I), according to the invention, are prepared according to a process which consists in reacting an aqueous ammonia solution with a heterocyclic compound of formula (IV) below, then to carry out a selective reduction of the dinitro-2,4, hydroxyalkyl-6 aniline of formula (III) obtained, to obtain a nitro-2, amino-4, hydroxyalkyl-6 aniline of formula (II) ), which is then optionally subjected to a conventional chemical process of alkylation, hydroxyalkylations or aminoalkylation to obtain the final compound of formula (I). .........-.......
Le schéma du procédé est le suivant : 30 . R’ R’ R’The process diagram is as follows: 30. R ’R’ R ’
°2NY^^i^'X\ 02V^A0H Rëductlo\ H2V^W-X-0H° 2NY ^^ i ^ 'X \ 02V ^ A0H Rëductlo \ H2V ^ W-X-0H
J + NH^—^ sélective^ j N02 * N02 no2 35 (IV) (III) (II) R’ et X ayant la signification indiquée ci-dessus.J + NH ^ - ^ selective ^ j N02 * N02 no2 35 (IV) (III) (II) R ’and X having the meaning indicated above.
33
Ce procédé permet d’obtenir d’excellents rendements en composé final de formule (II) ou (I).This process makes it possible to obtain excellent yields of final compound of formula (II) or (I).
La réaction de l’ammoniac sur le composé hétérocyclique de formule (IV) s’effectue à une température comprise entre 20 et 120°C, éventuel-5 lement sous pression et éventuellement en présence de solvants protiques polaires tels que l’eau, les alcools, les glycols ou éthers de glycols, ou de solvants aprotiques polaires tels que le formamide, le dimëthyl-formamide, le dioxane, le tétrahydrofuranne.The reaction of ammonia with the heterocyclic compound of formula (IV) takes place at a temperature between 20 and 120 ° C, optionally under pressure and optionally in the presence of polar protic solvents such as water, alcohols, glycols or glycol ethers, or polar aprotic solvents such as formamide, dimethyl-formamide, dioxane, tetrahydrofuran.
La réduction sélective du composé de formule (III) s’effectue par 10 transfert d’hydrogène du cyclohexène au composé (III), le Pd/C étant utilisé comme catalyseur, en présence d’alcool, d’eau et d’un acide minéral tel que l’acide chlorhydrique concentré.The selective reduction of the compound of formula (III) is carried out by hydrogen transfer from cyclohexene to compound (III), Pd / C being used as catalyst, in the presence of alcohol, water and an acid. mineral such as concentrated hydrochloric acid.
Les composés (II) peuvent être également obtenus par réduction sélective des composés III, dans un solvant polaire tel qu’un alcool en 15 Cj-C^, par introduction d'hydrogène, en présence d’un catalyseur d’hy drogénation tel que le Pd/C et d’une solution aqueuse d’un acide minéral tel que HCl, ou H^PO^, à une température comprise entre 20 et 90°C.The compounds (II) can also be obtained by selective reduction of the compounds III, in a polar solvent such as a Cj-C ^ alcohol, by the introduction of hydrogen, in the presence of a hydrogenation catalyst such as Pd / C and an aqueous solution of a mineral acid such as HCl, or H ^ PO ^, at a temperature between 20 and 90 ° C.
Ce procédé est décrit dans le brevet français 1 303 215.This process is described in French patent 1,303,215.
Les composés de formule (IV) sont obtenus par nitration des com-20 posés de formule (V) suivante : ^ ) (y) -°y 25 dans laquelle X et R’ ont les significations indiquées ci-dessus.The compounds of formula (IV) are obtained by nitration of the compounds of formula (V) below: ^) (y) - ° y 25 in which X and R ’have the meanings indicated above.
Les composés de formule (V) sont connus.The compounds of formula (V) are known.
La nitration s'effectue en ajoutant le composé (V) à l’acide nitrique fumant à une température comprise entre 30 et 35°C selon G. CHATELUS, Ann. Chlm. 4_, 505-547 (1949) ou en ajoutant le composé (V) 30 â un mélange sulfonitrique à une température voisine de 5°C, selon Charles D. HURD, Rostyslaw DOWBENKO, JACS 80, p. 4711-14 (1958). Le composé dinitré (IV) est isolé par dilution du milieu réactionnel à 1’eau.Nitration is carried out by adding compound (V) to fuming nitric acid at a temperature between 30 and 35 ° C according to G. CHATELUS, Ann. Chlm. 4_, 505-547 (1949) or by adding compound (V) 30 to a sulfonitric mixture at a temperature in the region of 5 ° C, according to Charles D. HURD, Rostyslaw DOWBENKO, JACS 80, p. 4711-14 (1958). The dinitrated compound (IV) is isolated by dilution of the reaction medium with water.
Les composés de formule (IV) dans laquelle X désigne le radical 35 éthylène, propylène, diméthyl-1,1 éthylène, diméthyl-1,2 éthylène ou trlméthyl-1,1,2 éthylène, sont connus.The compounds of formula (IV) in which X denotes the radical ethylene, propylene, 1,1-dimethyl ethylene, 1,2-dimethyl ethylene or methyl 1,1,2 ethylene, are known.
4 *4 *
La présente invention a également pour objet une composition tinctoriale pour fibres kératiniques, et plus particulièrement pour cheveux humains, contenant une n itr o-2, am in o-4, hydr oxya 1 kyl-6 aniline de formule (I) ci-dessus, ainsi qu’un procédé de coloration des fibres këratiniques, 5 et plus particulièrement des cheveux humains, utilisant ladite composi tion tinctoriale.The present invention also relates to a dye composition for keratin fibers, and more particularly for human hair, containing a n itr o-2, am in o-4, hydr oxya 1 kyl-6 aniline of formula (I) above , as well as a process for dyeing keratin fibers, and more particularly human hair, using said dye composition.
- Les compositions tinctoriales conformes à l’invention contiennent, dans un milieu solvant, au moins un composé répondant I la formule (I) ou l’un de ses sels cosmétiquement acceptables, et peuvent être utili— 1Q sées pour la coloration directe des fibres këratiniques ou pour la coloration d’oxydation de ces fibres, auquel cas les composés de formule * (I) confèrent des reflets complémentaires à la coloration de base obtenue par développement oxydant de précurseurs de colorants d’oxydation.- The dye compositions in accordance with the invention contain, in a solvent medium, at least one compound corresponding to formula (I) or one of its cosmetically acceptable salts, and can be used for direct dyeing of fibers keratinous or for the oxidation coloring of these fibers, in which case the compounds of formula * (I) confer reflections complementary to the basic coloring obtained by oxidative development of oxidation dye precursors.
Ces compositions contiennent les composés selon l’invention dans 15 des proportions comprises entre 0,001 et 5% en poids et de préférence entre 0,05 et 2% en poids par rapport au poids total de la composition.These compositions contain the compounds according to the invention in proportions of between 0.001 and 5% by weight and preferably between 0.05 and 2% by weight relative to the total weight of the composition.
Le milieu solvant est de préférence un véhicule cosmétique généralement constitué par de l’eau, mais on peut également ajouter, dans * les compositions, des solvants organiques pour solubiliser des ccmpo- 20 ses qui ne seraient pas suffisamment solubles dans l’eau. Parmi ces .vfînlvants, on peut citer les alcanols inférieurs tels que l’éthanol et l’isopropanol, les alcools aromatiques comme l’alcool benzylique, les polyols tels que le glycërol, les glycols ou éthers de glycols comme 'le butoxy-2 éthanol ou l’êthoxy-2 éthanol, l’éthylèneglycol, le pro-25 pylèneglycol, le moncméthyléther et le monoéthyléther du diéthylène-giycol ainsi que les produits analogues et leurs mélanges.The solvent medium is preferably a cosmetic vehicle generally consisting of water, but it is also possible to add, in the compositions, organic solvents to dissolve compounds which are not sufficiently soluble in water. Among these solvents, mention may be made of lower alkanols such as ethanol and isopropanol, aromatic alcohols such as benzyl alcohol, polyols such as glycerol, glycols or glycol ethers such as 2-butoxyethanol or 2-ethoxyethanol, ethylene glycol, pro-pylene glycol, monethylethyl ether and monoethyl ether of diethylene glycol as well as analogues and mixtures thereof.
Ces solvants sont de préférence présents^dans des proportions allant de 1 à 75Z en poids et en particulier de 5 à 50% en poids par rapport au poids total de la composition.These solvents are preferably present in proportions ranging from 1 to 75% by weight and in particular from 5 to 50% by weight relative to the total weight of the composition.
30 Ces compositions peuvent contenir des agents tensio-actifs anio niques, cationiques, non-ioniques, amphotères ou leurs mélanges. Ces produits tensio-actifs sont présents dans les compositions de l’invention dans des proportions comprises entre 0,5 et 55% en poids et de 5 préférence entre 4 et 40% en poids par rapport au poids total de la composition.These compositions may contain anionic, cationic, nonionic, amphoteric surfactants or mixtures thereof. These surfactants are present in the compositions of the invention in proportions of between 0.5 and 55% by weight and preferably between 4 and 40% by weight relative to the total weight of the composition.
Les compositions peuvent être épaissies de préférence avec des composés choisis parmi l'alglnate de sodium, la gomme arabique, les 5 dérivés de la cellulose tels que la méthylcellulose, l’hydroxyéthyl- cellulose, l’hydroxypropylméthylcellulose, la carboxyméthylcellulose et les polymères divers ayant la fonction d’épaississant tels que plus particulièrement les dérivés d’acide acrylique. Il est également possible d'utiliser des agents épaississants minéraux tels que la 1Q bentonite. Ces agents épaississants sont présents de préférence dans des proportions comprises entre 0,5 et 10% en poids et en particulier . entre 0,5 et 2% en poids par rapport au poids total de la composition.The compositions may preferably be thickened with compounds chosen from sodium alglnate, gum arabic, cellulose derivatives such as methylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose and various polymers having thickening function such as more particularly acrylic acid derivatives. It is also possible to use mineral thickening agents such as 1Q bentonite. These thickening agents are preferably present in proportions of between 0.5 and 10% by weight and in particular. between 0.5 and 2% by weight relative to the total weight of the composition.
Les compositions selon l'invention peuvent également contenir divers adjuvants habituellement utilisés dans les compositions tinc-15 toriales pour cheveux et en particulier des agents de pénétration, des agents dispersants, des agents séquestrants, des agents filmpgènes, des tampons et des parfums.The compositions according to the invention can also contain various adjuvants usually used in hair dye compositions and in particular penetration agents, dispersing agents, sequestering agents, film-forming agents, buffers and perfumes.
Ces compositions peuvent se présenter sous des formes diverses telles que liquide, crème, gel ou toute autre forme appropriée pour 20 réaliser une teinture des cheveux. Elles peuvent en outre être con ditionnées en flacons aérosols en présence d'un agent propulseur.'These compositions can be in various forms such as liquid, cream, gel or any other form suitable for dyeing the hair. They can also be packaged in aerosol bottles in the presence of a propellant.
Le pH de ces compositions tinctoriales peut être compris entre 3 et 11,5, de préférence entre 5 et 11,5. On l’ajuste à la valeur souhaitée à l'aide d'un agent alcallnisant tel que l’ammoniaque, le 25 carbonate de sodium, de potassium ou d'ammonium, les hydroxydes de sodium ou de potassium, les alcanolamines telles que la mono, la dieu la triéthanolamine, l'amino-2 méthyl-2 propanol-1, l'amino-2 méthyl-2 propanediol-1,3, les alkylamines telles que l'ëthylamine ou la triéthylamine ou à l'aide d’un agent d’acidification tel que les 30 acides phosphorique, chlorhydrique, tartrique, acétique, lactique ou citrique.The pH of these dye compositions can be between 3 and 11.5, preferably between 5 and 11.5. It is adjusted to the desired value using an alkalizing agent such as ammonia, sodium, potassium or ammonium carbonate, sodium or potassium hydroxides, alkanolamines such as mono , the god triethanolamine, 2-amino-2-methyl-propanol-1, 2-amino-2-methyl-propanediol-1,3, alkylamines such as ethylamine or triethylamine or using a acidifying agent such as phosphoric, hydrochloric, tartaric, acetic, lactic or citric acids.
Lorsque les compositions sont destinées à être utilisées dans un procédé de coloration directe des cheveux, elles peuvent contenir en ä - plus des composés conformes à l’invention d’autres colorants direts 35 tels que des colorants azolques ou anthraquinoniques, comme par 6 exemple la tétra-amino-1,4,5,8 anthraquinone, des indophénols, des indoanilines et des colorants nitrés de la série benzénique différents des composés de formule (I).When the compositions are intended to be used in a direct hair coloring process, they may contain, in addition to compounds according to the invention, other direct dyes such as azole or anthraquinone dyes, such as, for example, tetra-amino-1,4,5,8 anthraquinone, indophenols, indoanilines and nitro dyes of the benzene series different from the compounds of formula (I).
Les concentrations de ces colorants directs autres que les colo-5 rants de formule (I) peuvent être comprises entre 0,001 et 5% en poids par rapport au poids total de la composition.The concentrations of these direct dyes other than the 5-dyes of formula (I) can be between 0.001 and 5% by weight relative to the total weight of the composition.
= Ces compositions, mises en oeuvre dans un procédé de teinture par coloration directe, sont appliquées sur les fibres kératiniques pendant un temps de pose variant de 5 à 50 minutes, puis les fibres sont jq rincées, éventuellement lavées au shampooing, rincées à nouveau et séchées.= These compositions, used in a dyeing process by direct dyeing, are applied to the keratin fibers for an exposure time varying from 5 to 50 minutes, then the fibers are jq rinsed, optionally washed with shampoo, rinsed again and dried.
Les compositions selon l’invention peuvent également être mises en oeuvre sous forme de lotions capillaires de mise en plis destinées tout à la fois à conférer aux cheveux une légère coloration ou des reflets et à améliorer la tenue de la mise en plis. Dans ce cas, elles 25 se présentent sous forme de solutions aqueuses, alcooliques ou hydroalcooliques renfermant au moins une résine cosmétique et leur application s’effectue sur des cheveux humides préalablement lavés et rincés qui sont éventuellement enroulés puis séchés.The compositions according to the invention can also be used in the form of hair styling lotions intended at the same time to give the hair a light coloring or reflections and to improve the hold of styling. In this case, they are in the form of aqueous, alcoholic or hydroalcoholic solutions containing at least one cosmetic resin and their application is carried out on damp hair previously washed and rinsed which are optionally coiled and then dried.
Les résines cosmétiques utilisées dans les lotions de mise en 20 plis peuvent être en particulier la polyvinylpyrrolidone, les copo-.lymeres acide crotonique-acëtate de vinyle, vinylpyrrolidone-acétate de vinyle, anhydride maléique-éther butylvinylique, anhydride malé-, ique-éther mëthylvinylique ainsi que tout autre polymère cationique, anionique, non ionique ou amphotère habituellement utilisé dans ce 25 type de composition. Ces résines cosmétiques entrent dans les compo--sd-tions de l’invention à raison de 0,5 à 4% en poids, et de préférence de 1 à 3% en poids sur la base du poids total de la composition.The cosmetic resins used in the styling lotions may be in particular polyvinylpyrrolidone, copotyllyers crotonic acid-vinyl acetate, vinylpyrrolidone-vinyl acetate, maleic anhydride-butylvinyl ether, maleic anhydride-ether methyl vinyl as well as any other cationic, anionic, nonionic or amphoteric polymer usually used in this type of composition. These cosmetic resins are included in the compositions of the invention in an amount of 0.5 to 4% by weight, and preferably from 1 to 3% by weight based on the total weight of the composition.
Lorsque les compositions selon l’invention constituent des teintures d’oxydation impliquant la révélation par un oxydant, les ccmpo-30 sés de formule (I) conformes à l’invention sont essentiellement uti-; lisës en vue d’apporter des reflets à la teinture finale.When the compositions according to the invention constitute oxidation dyes involving revelation by an oxidant, the ccmpo-30s of formula (I) in accordance with the invention are essentially used; read in order to bring reflections to the final dye.
Ces compositions contiennent alors en association avec au moins un colorant nitré de formule (I) et éventuellement d’autres colorants directs, des précurseurs de colorants par oxydation.These compositions then contain, in combination with at least one nitrated dye of formula (I) and optionally other direct dyes, dye precursors by oxidation.
t i ! ! / /) 7t i! ! / /) 7
Elles peuvent contenir par exemple des paraphënylènedlamines telles que : la paraphénylènediamine, la paratoluylènediamine, la chloro-2 paraphénylènediamine, la diméthyl-2,6 paraphénylènediamine, la diméthyl-2,6 méthoxy-3 paraphénylènediamine, la N-(yô-méthoxy-5 ëthyl)paraphénylènediamine, la N,N-( ^3r-hydroxyéthyl)paraphénylène diamine, la N,N-(éthyl, carbamylméthyl) amino-4 aniline, ainsi que leurs sels.They may for example contain paraphenylenedlamines such as: paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-dimethyl-3-methoxy-3-paraphenylenediamine, N- (yô-methoxy-5 ethyl) paraphenylenediamine, N, N- (^ 3r-hydroxyethyl) paraphenylene diamine, N, N- (ethyl, carbamylmethyl) 4-amino aniline, as well as their salts.
Elles peuvent également contenir des paraaminophénols, par exemple : le paraaminophénol, le N-méthyl paraaminophénol, le chloro-jp 2-amino-4 phénol, le ehloro-3 amino-4 phénol, le méthyl-2 amino-4 phénol, et leurs sels.They can also contain paraaminophenols, for example: paraaminophenol, N-methyl paraaminophenol, chloro-jp 2-amino-4 phenol, ehloro-3 amino-4 phenol, methyl-2 amino-4 phenol, and their salts.
Elles peuvent également contenir de l’orthoaminpphénol.They may also contain orthoaminpphenol.
Elles peuvent aussi contenir des dérivés hétérocycliques, par ~ exemple : la diamino-2,5 pyridine, l’amino-7 benzomorpholine.They can also contain heterocyclic derivatives, for example: 2,5-diamino pyridine, 7-amino benzomorpholine.
Les compositions selon l’Invention peuvent contenir en association avec les précurseurs de colorants par oxydation, des coupleurs bien connus dans l’état de la technique.The compositions according to the invention may contain, in combination with the dye precursors by oxidation, couplers well known in the state of the art.
A titre de coupleurs, on peut citer notamment : les métadiphénols, les métaaminophénols et leurs sels, les métaphënylènediamines et leurs 20 sels, les métaacylaminophënols, les mëtaurëidophénols, les métacarbal- c oxyamin ophén ol s.As couplers, there may be mentioned in particular: metadiphenols, metaaminophenols and their salts, metaphenylenediamines and their salts, metaacylaminophenols, metaurideidophenols, metacarbal-c oxyamin ophen ol s.
On peut enfin mentionner comme autres coupleurs utilisables dans les compositions de l’invention : 1’ -naphtol, les coupleurs possédant un groupement méthylène actif tels que les composés dicétoniques 25 et les pyrazolones et les coupleurs hétérocycliques dérivés de la pyridine et de la benzomorpholine.Finally, mention may be made of other couplers which can be used in the compositions of the invention: 1 ′ -naphthol, couplers having an active methylene group such as diketonic compounds and pyrazolones and heterocyclic couplers derived from pyridine and benzomorpholine.
Ces compositions contiennent, en plus des précurseurs de colorants par oxydation, des agents réducteurs présents dans des proportions comprises entre 0,05 et 3% en poids par rapport au poids total de la . 30 composition.These compositions contain, in addition to dye precursors by oxidation, reducing agents present in proportions of between 0.05 and 3% by weight relative to the total weight of the. 30 composition.
Les précurseurs de colorants par oxydation peuvent être utilisés, dans les compositions de l’invention, à des concentrations comprises entre 0,001 et 5% en poids et de préférence entre 0,03 et 2% en poids sur la base du poids total de la composition. Les coupleurs peuventThe dye precursors by oxidation can be used, in the compositions of the invention, at concentrations of between 0.001 and 5% by weight and preferably between 0.03 and 2% by weight based on the total weight of the composition. . The couplers can
AAT
/'(/ 8 également être présents dans des proportions comprises entre 0,001 et 5% en poies, de préférence entre 0,015 et 2% en poids. Le pH de ces compositions de teinture par oxydation est de préférence compris entre 7 et 11,5 et est ajusté à l’aide d'agents alcalinisants définis 5 ci-dessus./ '(/ 8 also be present in proportions of between 0.001 and 5% by weight, preferably between 0.015 and 2% by weight. The pH of these oxidation dyeing compositions is preferably between 7 and 11.5 and is adjusted using basifying agents defined above.
Le procédé de teinture des fibres kératiniques, en particulier - des cheveux humains, mettant en oeuvre la révélation par un oxydant, consiste à appliquer sur les cheveux la composition tinctoriale comprenant à la fois un colorant selon l’invention et les précurseurs 1Q de colorants. Le développement de la coloration peut alors s’effectuer lentement en présence de l’oxygène de l’air, mais on utilise de pré-• férence un système révélateur chimique qui est le plus souvent choisi parmi l’eau oxygénée, le peroxyde d’urée et les persels. On utilise en particulier une solution d’eau oxygénée à 20 volumes.The process for dyeing keratin fibers, in particular - human hair, using revelation by an oxidant, consists in applying to the hair the dye composition comprising both a dye according to the invention and the 1Q dye precursors. The development of the coloring can then be carried out slowly in the presence of oxygen from the air, but preferably a chemical developing system is used which is most often chosen from hydrogen peroxide, peroxide of urea and persalts. In particular, a 20-volume hydrogen peroxide solution is used.
15 Une fois que l’on a appliqué sur les fibres kêratiniques la com position avec l’agent oxydant, on laisse poser pendant 10 à 50 minutes, de préférence 15 à 30 minutes, après quoi on rince les fibres kérati-niques, on les lave éventuellement au shampooing, on les rince à nouveau et on sèche.Once the composition with the oxidizing agent has been applied to the keratin fibers, it is left to stand for 10 to 50 minutes, preferably 15 to 30 minutes, after which the keratin fibers are rinsed, they are optionally wash with shampoo, rinse again and dry.
20 Les exemples qui suivent sont destinés à illustrer l’invention -sans présenter un caractère limitatif.The examples which follow are intended to illustrate the invention - without being limiting in nature.
EXEMPLE DE PREPARATION 1 , Préparation du (diamino-2,5,nitro-3)phényl-2 éthanol-1 _ o2n_x^^v_ch2ch2ohPREPARATION EXAMPLE 1, Preparation of (2,5-diamino, 3-nitro) 2-phenyl-1-ethanol _ o2n_x ^^ v_ch2ch2oh
25 I NH„/HC0NH„ I25 I NH „/ HC0NH„ I
I —J_2—v | lo2 ko2 H2NVxX^Y^CH2CH2OH Réduction j.I —J_2 — v | lo2 ko2 H2NVxX ^ Y ^ CH2CH2OH Reduction j.
3030
To2 1ère étapeTo2 1st stage
Préparation de 1’ (amino-2,dinitro-3,5)phënyl-2 ëthanol-1 ; On met en suspension dans 350 ml d’ammoniaque à 20% et 220 ml de 35 formamide, 0,17 mole (35,7 g) de dihydro-2,3,dinitro-5,7 benzofurane y fy 9 préparé selon Chatelus Ann. Chim. QJJ» A» 505-547 (1949).Preparation of 1 ’(2-amino, 3,5-dinitro) 2-phenyl 1-ethanol; Suspended in 350 ml of 20% ammonia and 220 ml of formamide, 0.17 mole (35.7 g) of 2,3-dihydro, 5,7-dinitro benzofuran and fy 9 prepared according to Chatelus Ann . Chim. QJJ "A" 505-547 (1949).
Après 8 heures de chauffage à 110°C, on rajoute 100 ml d’ammoniaque à 20%. Le chauffage est maintenu pendant 4 heures. Par refroidissement du milieu réactionnel, le produit attendu précipite.After 8 hours of heating at 110 ° C., 100 ml of 20% ammonia are added. Heating is maintained for 4 hours. By cooling the reaction medium, the expected product precipitates.
5 Après essorage, lavage à l’eau glacée jusqu’à neutralité et séchage sous vide, on obtient 0,13 mole (30,3 g) d’un produit fondant à 151°C, que l’on recristallise du dioxane.5 After wringing, washing with ice-cold water until neutral and drying under vacuum, 0.13 mol (30.3 g) of a product melting at 151 ° C. is obtained, which is recrystallized from dioxane.
L’analyse du produit donne les résultats suivants :The analysis of the product gives the following results:
Analyse Calculé pour Trouvé !0 C8H9N305 %C 42,29 42,24 %H 3,99 3,91 %N 18,50 18,60 %0 35,21 35,14 15 2ëme étapeAnalysis Calculated for Found! 0 C8H9N305% C 42.29 42.24% H 3.99 3.91% N 18.50 18.60% 0 35.21 35.14 15 2nd step
Préparation du (diamino-2,5 nitro-3)phënyl-2 éthanol-1 A une suspension de 15,7 g de Pd/C à 10% dans 290 ml d’éthanol absolu additionné de 35 ml d’acide chlorhydrique concentré et de 64 ml . de cyclohexène, on ajoute 0,141 mole (32 g) d’ (amino-2,dinitro-3,5) 20 phënyl-2 éthanol-1. Après 1 h 45 de chauffage au reflux, le milieu réactionnel est filtré à chaud pour éliminer le catalyseur. Le filtrat est évaporé à sec sous vide et l’extrait sec, après avoir été lavé à l'éthanol absolu, est solubilisé à chaud dans l'eau. On ajoute 15 ml d’ammoniaque à 20%. Par-refroidissement, on obtient un précipité rouge 25 du produit attendu qui, après essorage, est recristallisé du Méthyl-caLlosolve. Après séchage, le produit fond à 190°C.Preparation of (2,5-diamino-3-nitro) 2-phenyl-1-ethanol To a suspension of 15.7 g of Pd / C at 10% in 290 ml of absolute ethanol supplemented with 35 ml of concentrated hydrochloric acid and of 64 ml. of cyclohexene, 0.141 mol (32 g) of (2-amino, 3,5-dinitro) 20 2-phenyl-1-ethanol is added. After 1 h 45 of heating at reflux, the reaction medium is filtered hot to remove the catalyst. The filtrate is evaporated to dryness under vacuum and the dry extract, after being washed with absolute ethanol, is dissolved hot in water. 15 ml of 20% ammonia are added. By cooling, a red precipitate is obtained of the expected product which, after spinning, is recrystallized from methyl-caLlosolve. After drying, the product melts at 190 ° C.
Masse moléculaire calculée pour C0H N_0_ : 197.Molecular mass calculated for C0H N_0_: 197.
O il j JO he j J
Masse moléculaire trouvée par dosage potentiométrique dans l’acide acétique par l’acide perchlorique : 199,5.Molecular mass found by potentiometric determination in acetic acid with perchloric acid: 199.5.
30 L'analyse du produit obtenu donne les résultats suivants :Analysis of the product obtained gives the following results:
Analyse Calculé pour Trouvé C8H11N3°3 %C 48,72 48,88 %H 5,62 . 5,67 35 %N 21,31 21,33 ; - %0 24,34 24,60 t i j /y 10 EXEMPLE DE PREPARATION 2Analysis Calculated to Found C8H11N3 ° 3% C 48.72 48.88% H 5.62. 5.67 35% N 21.31 21.33; -% 0 24.34 24.60 t i d / y 10 PREPARATION EXAMPLE 2
Préparation du (diamino-2,5,nitro-3)phényl-l propanol-2Preparation of (2,5-diamino, 3-nitro) phenyl-1-propanol-2
°2N° 2N
NÏÏ3/CH3OCH2CH2OH INÏÏ3 / CH3OCH2CH2OH I
^ 5 ^ \^^-nh2 N02 N02 H2li^v^s_.CH2CHOHCH3 Réduction v -7 —nh2 10 Ï02 1ère étape^ 5 ^ \ ^^ - nh2 N02 N02 H2li ^ v ^ s_.CH2CHOHCH3 Reduction v -7 —nh2 10 Ï02 1st stage
Préparation de 1'(amino-2,dinitro-3,5)phényl-l propanol-2 On met en suspension dans 1,1 litre d'ammoniaque à 20% et 600 ml de Méthylcellosolve 0,39 mole (88 g) de dihydro-2,3,dinitro-5,7,mithyl-2 15 benzofurane préparé selon J.A.C.S. 80 p. 4711-4714 (1958). .Après 18 heures de chauffage à 70°C, le milieu réactionnel est refroidi. On essore le précipité formé qui, après réempatage dans l'eau jusqu’à neutralité, puis séchage sous vide, est recristallisé de 170 ml de dioxane. On obtient, après séchage sous vide, 0,30 mole (72 g) du produit attendu; il fond à 20 177°C.Preparation of 1 '(2-amino, 3,5-dinitro) phenyl-1-propanol-2 Is suspended in 1.1 liters of 20% ammonia and 600 ml of methylcellosolve 0.39 mole (88 g) of 2,3-dihydro, 5,7 dinitro, 2-mithyl benzofuran prepared according to JACS 80 p. 4711-4714 (1958). .After 18 hours of heating at 70 ° C, the reaction medium is cooled. The precipitate formed is drained which, after repacking in water until neutral, then drying under vacuum, is recrystallized from 170 ml of dioxane. After drying under vacuum, 0.30 mol (72 g) of the expected product is obtained; it melts at 20,177 ° C.
'L'analyse donne les résultats suivants : j Analyse Calculé pour Trouvé C9H11N3°5 %C 44,81 44,87 25 %H 4,60 4,62 %N 17,42 17,45 %0 “ 33,17 33,08 2ëme étape ’ Préparation du (diamino-2,5,nitro-3)phényl-l propanol-2 30 A une suspension de 5,6 g de Pd/C à 10% dans 100 ml d’éthanol absolu additionné de 12,5 ml d’acide chlorhydrique concentré et de 23 ml de cyclohexène, on ajoute 0,05 mole (12,05 g) d’(amdno-2,dinitro-3,5)phényl-l propanol-2. Après 3 heures de chauffage au reflux, le : milieu réactionnel est filtré à chaud pour éliminer le catalyseur. Le 11 filtrat est évaporé à sec, l’extrait sec est réempité dans un mélange éthanol/éther éthylique, puis solubilisé à chaud dans le minimum d’eau.The analysis gives the following results: j Analysis Calculated for Found C9H11N3 ° 5% C 44.81 44.87 25% H 4.60 4.62% N 17.42 17.45% 0 “33.17 33, 08 2nd step 'Preparation of (2,5-diamino, 3-nitro) phenyl-1-propanol-2 30 To a suspension of 5.6 g of Pd / C at 10% in 100 ml of absolute ethanol supplemented with 12, 5 ml of concentrated hydrochloric acid and 23 ml of cyclohexene, 0.05 mol (12.05 g) of (2-amdno, 3,5-dinitro) phenyl-1-propanol-2 is added. After 3 hours of heating at reflux, the reaction medium is filtered hot to remove the catalyst. The 11 filtrate is evaporated to dryness, the dry extract is re-stirred in an ethanol / ethyl ether mixture, then dissolved hot in the minimum amount of water.
On ajoute 15 ml d’ammoniaque à 20% afin de libérer le chlorhydrate. Le produit attendu précipite. Après essorage, lavage à l’eau et recristal-5 lisation de l’éthanol à 96°, il fond à 168°C.15 ml of 20% ammonia are added to release the hydrochloride. The expected product precipitates. After spinning, washing with water and recrystallization of the ethanol at 96 °, it melts at 168 ° C.
Hasse moléculaire calculée pour : 211Molecular weight calculated for: 211
Masse moléculaire trouvée par dosage potentiométrique dans l’acide acétique par l’acide perchlorique : 210.Molecular mass found by potentiometric determination in acetic acid with perchloric acid: 210.
L’analyse du produit obtenu donne les résultats suivants : 1Q Analyse Calculé pour Trouvé C9H13^3°3 %C 51,17 51,31 %H 6,20 6,21 %N 19,90 20,03 15 %0 22,73 22,66 EXEMPLE DE PREPARATION 3Analysis of the product obtained gives the following results: 1Q Analysis Calculated for Found C9H13 ^ 3 ° 3% C 51.17 51.31% H 6.20 6.21% N 19.90 20.03 15% 0 22, 73 22.66 PREPARATION EXAMPLE 3
Préparation de 1’/amino-2,(^-hydroxyéthyl)amino-5,nitro-33phënyl-l propanol-2 ΝΗ2ν^ν-^2εΗΟΗΟΗ3 Cl (CH^OOCNH ^^^vjC^CHOHCH^ - 1 ^ Il —-NÏÏ2 C1C00CH2CH2C1Preparation of 1 '/ amino-2, (^ - hydroxyethyl) amino-5, nitro-33phenyl-l propanol-2 ΝΗ2ν ^ ν- ^ 2εΗΟΗΟΗ3 Cl (CH ^ OOCNH ^^^ vjC ^ CHOHCH ^ - 1 ^ Il—- NÏÏ2 C1C00CH2CH2C1
~*î™3 ^ S~ * î ™ 3 ^ S
f-1f-1
\ I CH30Na/CH30H\ I CH30Na / CH30H
HOCH2CHjjH ,CH2CHOHCH3 >y^s^£H2CHOHCH3HOCH2CHjjHH, CH2CHOHCH3> y ^ s ^ £ H2CHOHCH3
I ( Na0H III (Na0H II
"°2 H"° 2 H
30 1ère étape30 1st stage
Préparation de 1’Qamino-4,|£>-hydroxypropyl-5,nitro-3)phëny]Q carbamate de Λ -chlorëthylePreparation of amino-4, | £> -hydroxypropyl-5, nitro-3) phëny] Q Λ -chlorethyl carbamate
On dissout 0,07 mole (14,8 g) de (diamino-2,5,nitro-3)phényl-l propanol-2 obtenu dans l’exemple de préparation 2, dans 59 ml de dioxane /! 12 additionnés de 22 ml d’eau. On ajoute 0,0385 mole (5,3 g) de carbonate de potassium. On élève la température à 90°C, puis on Introduit peu à peu, sous agitation, 0,077 mole (11 g) de chloroformiate de y^-chloré- thyle. L’addition terminée, on verse le mélange réactionnel sur 400 g 5 d’un mélange eau-glace. Le produit attendu précipite; après essorage « et séchage sous vide, on obtient 21,8 g du produit attendu. Il fond à 115°C.0.07 mole (14.8 g) of (2.5-diamino, 3-nitro-3) phenyl-1-propanol-2 obtained in Preparation Example 2 is dissolved in 59 ml of dioxane /! 12 added with 22 ml of water. 0.0385 mole (5.3 g) of potassium carbonate is added. The temperature is raised to 90 ° C., then 0.077 mol (11 g) of γ-chloroethyl chloroformate is gradually introduced, with stirring. When the addition is complete, the reaction mixture is poured onto 400 g 5 of a water-ice mixture. The expected product precipitates; after spinning "and drying under vacuum, 21.8 g of the expected product are obtained. It melts at 115 ° C.
2ëme étape2nd stage
Préparation de la tj -£(amino-4^ fo -hydroxypropyl-5 ,nitro-3)phényl3 10 oxazolidone C —Preparation of tj - £ (4-amino ^ fo-hydroxypropyl-5, 3-nitro) phenyl3 10 oxazolidone C -
On met en suspension 0,056 mole (17,8 g) d’ £(amino-4, y3-hydroxy-> propyl-5,nitr0-3)phénylj carbamate de ^2>-chloréthyle dans 107 ml d’alcool à 96°. On coule goutte à goutte 12 ml d’une solution de méthylate de sodium à30% dans le mêthanol en maintenant la température à 10°C. Après 15 essorage et rêempâtage dans l’eau, on obtient 0,041 mole (11,6 g) du produit attendu.0.056 mol (17.8 g) of £ (amino-4, y3-hydroxy-> propyl-5, nitr0-3) phenylj ^ 2> -chloroethyl carbamate are suspended in 107 ml of 96 ° alcohol . 12 ml of a 30% sodium methylate solution in methanol are added dropwise while maintaining the temperature at 10 ° C. After 15 wringing and repasting in water, 0.041 mol (11.6 g) of the expected product is obtained.
3ëme étape3rd stage
Préparation de l’£amino-2,(^rhydraxyéthyl)amino-5,nitr0-3*1} phényl-1 propanol-2 20 Dans 46 ml d'alcool à 96°, on introduit 0,041 mole (11,5 g) de N-ßamino-4,ß-hydroxypropy 1-5,nitro-3)phényl]oxazol±done. On élève la température à 85?C et on coule goutte è goutte 8,2 ml de soude 10 N.Preparation of £ amino-2, (^ rhydraxyethyl) amino-5, nitr0-3 * 1} phenyl-1 propanol-2 20 0.041 mol (11.5 g) is introduced into 46 ml of 96 ° alcohol of N-ßamino-4, ß-hydroxypropy 1-5, nitro-3) phenyl] oxazol ± done. The temperature is raised to 85 ° C. and 8.2 ml of 10N sodium hydroxide are poured dropwise.
Le chauffage est maintenu 15 minutes après la fin de la coulée. Après filtration, le filtrat est évaporé à sec, puis le résidu est repris par 25 40 ml d’eau. Le produit attendu cristallise; après recristallisation de . .lleau, il fond â 130°C.Heating is maintained 15 minutes after the end of the casting. After filtration, the filtrate is evaporated to dryness, then the residue is taken up in 40 ml of water. The expected product crystallizes; after recrystallization of. .lleau, it melts at 130 ° C.
Masse moléculaire calculée pour : 255Molecular mass calculated for: 255
Masse moléculaire trouvée par dosage potentianétrique dans l'acide acétique par l’acide perchlorique : 256.Molecular mass found by potentianetric determination in acetic acid with perchloric acid: 256.
30 L’analyse du produit obtenu donne les résultats suivants :The analysis of the product obtained gives the following results:
Analyse Calculé pour Trouvé C11H17N3°4 %C 51,75 51,80 %H _ 6,71 - 6,70 35 ZN 16,46 16,62 %0 25,07 25,18 | i iAnalysis Calculated for Found C11H17N3 ° 4% C 51.75 51.80% H _ 6.71 - 6.70 35 ZN 16.46 16.62% 0 25.07 25.18 | i i
* /,G* /, G
i 13 EXEMPLE 1i 13 EXAMPLE 1
On prépare la composition tinctoriale suivante : (diamino-2,5,nitro-3)phënyl-2,ëthanol-l 0,54 gThe following dye composition is prepared: (2.5-diamino, 3-nitro) 2-phenyl, 1-ethanol-0.54 g
Butoxy-2 éthanol 15 g 5 CELLOSIZE WP 03 2gButoxy-2 ethanol 15 g 5 CELLOSIZE WP 03 2g
Chlorure d’alkyl(suif)dimëthyl hydroxyéthyl ammonium 2 gAlkyl chloride (tallow) dimethyl hydroxyethyl ammonium 2 g
Monoéthanolamine en solution aqueuse à 20% 1 gMonoethanolamine in 20% aqueous solution 1 g
Eau qsp 100 g pH = 9,8 10 Ce mélange, appliqué 15 minutes à 30°C sur cheveux, leur confère, . après shampooing et rinçage, une coloration : 7.5 R 5/10 sur cheveux décolorés au blanc ' 7,5 R 5,5/6 sur cheveux naturellement blancs à 90%, ces couleurs étant exprimées selon la notation de Munsell, 15 EXEMPLE 2Water qs 100 g pH = 9.8 10 This mixture, applied for 15 minutes at 30 ° C on hair, gives them,. after shampooing and rinsing, coloring: 7.5 R 5/10 on hair bleached in white '7.5 R 5.5 / 6 on hair naturally white at 90%, these colors being expressed according to the Munsell notation, 15 EXAMPLE 2
On prépare la composition tinctoriale suivante : (diamino-2,5,nitro-3)phényl-l propanol-2 0,3 gThe following dye composition is prepared: (2,5-diamino, 3-nitro) phenyl-1 propanol-2 0.3 g
Butoxy-2 éthanol 10 g 2o Alcool à 96° 5 g CELLOSIZE WP 03 2 gButoxy-2 ethanol 10 g 2o 96 ° alcohol 5 g CELLOSIZE WP 03 2 g
Laurylsulfate d'ammonium 5 gAmmonium lauryl sulfate 5 g
Eau qsp 100 g pH = 6,9 25 Ce mélange, appliqué 20 minutes à 28°C sur cheveux, leur confère, après shampooing et rinçage, une coloration : 8 R 5/10 sur cheveux décolorés au blanc 7.5 R 5,5/6 sur cheveux naturellement blancs à 90%, ces couleurs étant exprimées selon la notation de Munsell.Water qs 100 g pH = 6.9 25 This mixture, applied for 20 minutes at 28 ° C on hair, gives them, after shampooing and rinsing, a coloring: 8 R 5/10 on hair bleached white 7.5 R 5.5 / 6 on naturally white hair at 90%, these colors being expressed according to the Munsell rating.
14 EXEMPLE 314 EXAMPLE 3
On prépare la composition tinctoriale suivante : t^mlno-2, ( ^-hydroxyéthyl) amino-5 ,nitro-3^ phényl-1 •propanol-2 0,7 g >- 5 Alcool à 96° 10 g ALFOL C16/lg 8 gThe following dye composition is prepared: t ^ mlno-2, (^ -hydroxyethyl) amino-5, nitro-3 ^ phenyl-1 • propanol-2 0.7 g> - 5 Alcohol at 96 ° 10 g ALFOL C16 / lg 8 g
Cire de Lanette E 0,5 g CEMULSOL B 1 gLanette wax E 0.5 g CEMULSOL B 1 g
Diëthanolamide oléique 1,5 g *10 Ammoniaque à 5Z qs pH = 9,9Oleic diethanolamide 1.5 g * 10 Ammonia at 5Z qs pH = 9.9
Eau qsp 10Ô gWater qs 10Ô g
Ce mélange, appliqué 10 minutes à 28°C sur cheveux, leur confère, . . après shampooing et rinçage, une coloration : , 7,5 RP 4/9 sur cheveux décolorés au blanc 15 7,5 RP 5,5/4 sur cheveux naturellement blancs ä 90%, ces couleurs étant exprimées selon la notation de Munsell.This mixture, applied 10 minutes at 28 ° C on hair, gives them,. . after shampooing and rinsing, a coloring:, 7.5 RP 4/9 on hair bleached with white 15 7.5 RP 5.5 / 4 on hair naturally white at 90%, these colors being expressed according to the Munsell notation.
EXEMPLE 4EXAMPLE 4
On prépare la composition tinctoriale suivante : 20 (diamino-2,5,nitro-3)phênyl-l prqpanol-2 0,16 gThe following dye composition is prepared: 20 (2.5-diamino, 3-nitro) phenyl-1 prqpanol-2 0.16 g
Amin0-2,nitro-3 toluène 0,095 gAmin0-2, 3-nitro toluene 0.095 g
Nitro-3, A*-hydroxypropylamino-4 aniline 0,12 g 7 -Tétraamino-1,4,5,8 anthraquinone 0,12 g (bleu saphir cibacète microdispersé) 25 LAURAM1DE 1^5 gNitro-3, A * -hydroxypropylamino-4 aniline 0.12 g 7 -Tetraamino-1,4,5,8 anthraquinone 0.12 g (blue sapphire cibacete microdispersed) 25 LAURAM1DE 1 ^ 5 g
Acide laurique 1 g CELLOSIZE WP 03 5g ’ Monoéthanolamine 2 gLauric acid 1 g CELLOSIZE WP 03 5g ’Monoethanolamine 2 g
Eau qsp 100 g ; 3q pH = 9,5 i Ce mélange, appliqué 20 minutes à 28°C sur cheveux naturellement blancs à 90%, leur confère, après shampooing et rinçage, une coloration blond cuivré.Water qs 100 g; 3q pH = 9.5 i This mixture, applied 20 minutes at 28 ° C to naturally white hair at 90%, gives them, after shampooing and rinsing, a coppery blond coloring.
j ' - i i /1/1 // i7 15 » EXEMPLE 5i - i i / 1/1 // i7 15 »EXAMPLE 5
On prépare la composition tinctoriale suivante : (diamino-2,5,nitro-3)phényl-2 éthanol-1 0,2 gThe following dye composition is prepared: (2.5-diamino, 3-nitro) 2-phenyl-1-ethanol 0.2 g
Amino-2,nitro-3 phénol 0,15 g 5 Bromhydrate de nitro-3,méthylamino-4,N-( ^-amino- êthyl)aniline 0,08 gAmino-2, 3-nitro phenol 0.15 g 5 Nitro-3 hydrobromide, 4-methylamino, N- (^ -amino-ethyl) aniline 0.08 g
Alcool à 96° 10 g LAURAMIDE 1,5 gAlcohol at 96 ° 10 g LAURAMIDE 1.5 g
Acide laurique 1 g 10 CELLOSIZE WP 03 5 g , Monoéthanolamlne 2 gLauric acid 1 g 10 CELLOSIZE WP 03 5 g, Monoethanolamine 2 g
Eau , qsp 100 g ‘ PH = 9,7Water, qs 100 g ‘PH = 9.7
Ce mélange, appliqué 25 minutes à 28°C sur cheveux décolorés au ]_5 blanc, leur confère, après shampooing et rinçage, une coloration cuivre rouge.This mixture, applied for 25 minutes at 28 ° C on hair bleached with white _5, gives them, after shampooing and rinsing, a red copper coloring.
EXEMPLE 6EXAMPLE 6
On prépare la composition tinctoriale suivante : £amin o-2, nitr o-3 (/¾ -hydr oxyëthy 1) amino-5j phény 1-1 2o jpropanol-2 0,36 gThe following dye composition is prepared: £ amin o-2, nitr o-3 (/ ¾ -hydr oxyëthy 1) amino-5j pheny 1-1 2o jpropanol-2 0.36 g
Nitro-3,amlno-4 phénol 0,13 g ^»-hydroxyéthylamdno-2, (dl- ß*-hydr oxyëthy lamino-4 anillno)-5 benzoquinone-1,4 0,17 gNitro-3, amlno-4 phenol 0.13 g ^ »- hydroxyethylamdno-2, (dl- ß * -hydr oxyëthy lamino-4 anillno) -5 benzoquinone-1,4 0.17 g
Alcool à 96° 20 g 25 CELLOSIZE WP 03 2 g96 ° alcohol 20 g 25 CELLOSIZE WP 03 2 g
Chlorure d’alkyl(suif)dlméthyl hydroxy éthyl ammonium 2 gAlkyl chloride (tallow) dlmethyl hydroxy ethyl ammonium 2 g
Triéthanolamine à 5% 0,2 g0.2% triethanolamine 0.2 g
Eau qsp 100 g pH = 7,7 30 Ce mélange, appliqué 20 minutes à 28°C sur cheveux naturellement blancs à 90%, leur confère, après shampooing et rinçage, une coloration blond cuivré.Water qs 100 g pH = 7.7 30 This mixture, applied for 20 minutes at 28 ° C to naturally white hair at 90%, gives them, after shampooing and rinsing, a coppery blond coloring.
16 EXEMPLE 7 (Diamino-2,5,nitro-3)phényl-1 propanol-2 0,7 g £Amino-2, (^3-hydr oxyêthyl)amino-5 ,nitro-£] phënyl-1 propanol-2 * 0,06 g „ 5 Dichlorhydrate de diamino-2,5 pyridine 0,05 g16 EXAMPLE 7 (2,5-Diamino, 3-nitro) 1-phenyl-2-propanol-0.7 g £ Amino-2, (^ 3-hydr oxyethyl) amino-5, nitro- £] 1-phenyl-2-propanol * 0.06 g „5 Diamino-2,5 dihydrochloride pyridine 0.05 g
Para-amin ophénol 0,08 g °(-naphtol 0,035 gPara-amin ophenol 0.08 g ° (-naphthol 0.035 g
Hydroxy-7 benzomorphollne 0,07 gHydroxy-7 benzomorphollne 0.07 g
Dichlorhydrate de (diamino-2,4)phënoxy-1 propanediol-10 2,3 0,04 g(2,4-diamino) phenoxy-1-propanediol-10 dihydrochloride 2.3 0.04 g
Dichlorhydrate de Ν-^δ -méthoxyéthyl paraphënylëne ' diamine 0,04 gΝ- ^ δ -methoxyethyl paraphenylene diamine 'dihydrochloride 0.04 g
Alcool oléique polyglycérolë à 2 moles de glycérol 4,5 gPolyglycerol oleic alcohol with 2 moles of glycerol 4.5 g
Alcool oléique polyglycérolë à 4 moles de glycérol 4,5 g 15 ETHCMEEN TO 12 4,5 g CCMPERLAN KD 9g . Prqpylèneglycol 4 gPolyglycerol oleic alcohol with 4 moles of glycerol 4.5 g 15 ETHCMEEN TO 12 4.5 g CCMPERLAN KD 9g. Prqpylene glycol 4 g
Butoxy-2 éthanol 8 gButoxy-2 ethanol 8 g
Ethanol à 96° 6 g 20 MASQUOL DTPA 2 gEthanol at 96 ° 6 g 20 MASQUOL DTPA 2 g
Hydroquinone 0,15 gHydroquinone 0.15 g
Solution de bisulfite de sodium à 35°Bé 1,3 g - Ammoniaque à 22°Bë 10 gSodium bisulfite solution at 35 ° Be 1.3 g - Ammonia at 22 ° Be 10 g
Eau qsp 100 g 25 pH *= 10,5Water qs 100 g 25 pH * = 10.5
Au moment de l’emploi, on ajoute 110 g d’eau oxygénée à 20 volumes.At the time of use, 110 g of hydrogen peroxide is added to 20 volumes.
Le mélange, appliqué 20 minutes a 28°C sur des cheveux naturellement blancs à 90%, leur confère après shampooing et rinçage,une coloration blond cendré.The mixture, applied for 20 minutes at 28 ° C to naturally white hair at 90%, gives them, after shampooing and rinsing, an ash blonde coloring.
30 · EXEMPLE 830 EXAMPLE 8
On prépare le mélange tinctorial suivant : jAmino^Cß -hydroxyéthyl) amino-5,nitro-3j phényl-1 propanol-2 0,1 g D^hydr oxyêthy 1) amin o-2, dinitr o-3,5] phënyl-2 35 éthanol-1 0,08 g 17 Méthyl-2 résorcine 0,06 gThe following dye mixture is prepared: jAmino ^ Cß-hydroxyethyl) amino-5, nitro-3j phenyl-1 propanol-2 0.1 g D ^ hydr oxyêthy 1) amin o-2, dinitr o-3,5] phenyl- 2 35 ethanol-1 0.08 g 17 2-methyl resorcin 0.06 g
Para-phénylènediamine 0,05 gPara-phenylenediamine 0.05 g
Dichlorhydrate de diamino-2,4 phénoxyéthan61 0,03 g CEMULSOL NP 4 21 g 5 CEMULSOL NP 9 24 g2,4-diamino-dihydrochloride phenoxyethan61 0.03 g CEMULSOL NP 4 21 g 5 CEMULSOL NP 9 24 g
Acide oléique 4 gOleic acid 4 g
Butoxy-2 éthanol 3 gButoxy-2 ethanol 3 g
Ethanol â 96° 10 g MASQUOL DTPA 2,5 g 10 Solution de bisulfite de sodium à 35°Bé 1 gEthanol at 96 ° 10 g MASQUOL DTPA 2.5 g 10 Sodium bisulfite solution at 35 ° Be 1 g
Ammoniaque â 22°Bé 10 gAmmonia at 22 ° Be 10 g
Eau qsp 100 g pH .10,6Water qs 100 g pH .10.6
Au moment de l'emploi, on ajoute 100 g d'eau oxygénée à 20 volumes. 15 Le mélange, appliqué 30 minutes à 28°C sur des cheveux décolorés, leur confère, après shampooing et rinçage, une coloration gris bleuté.At the time of use, 100 g of hydrogen peroxide are added to 20 volumes. The mixture, applied 30 minutes at 28 ° C to bleached hair, gives them, after shampooing and rinsing, a bluish gray coloring.
EXEMPLE 9EXAMPLE 9
On prépare le mélange tinctorial suivant : (Diamino2,5,nitro-3)phényl-2 éthanol-1 0,08 g 20 (p-hydroxyéthylam±no-2,dinitro-3,5)phënyl-2 éthanol-1 0,07 gThe following dye mixture is prepared: (Diamino2.5, nitro-3) 2-phenyl ethanol-1 0.08 g 20 (p-hydroxyethylam ± no-2, dinitro-3.5) 2-phenyl ethanol-1 0, 07 g
Para-phénylènediamine 0,06 g Résorcine 0,035 gPara-phenylenediamine 0.06 g Resorcin 0.035 g
Acétamido-5,méthyl-2 phénol 0,09 g phényl-l,méthyl-3,pyrazolone-5 0,065 g 25 CARBOPOL 934 3 gAcetamido-5, 2-methyl phenol 0.09 g phenyl-1, methyl-3, pyrazolone-5 0.065 g 25 CARBOPOL 934 3 g
Alcool â 96° 11 g96 ° alcohol 11 g
Butoxy-2 éthanol 5 gButoxy-2 ethanol 5 g
Chlorure d'alkyl(suif)diméthyl hydroxyéthyl ammonium 2 g TRILON B 0,2 g 30 Ammoniaque à 22°Bë 10 gAlkyl chloride (tallow) dimethyl hydroxyethyl ammonium 2 g TRILON B 0.2 g 30 Ammonia at 22 ° Bë 10 g
Bisulfite de sodium à 35°Bë 1 gSodium bisulfite at 35 ° Bë 1 g
Eau qsp 100 g pH - 10,2Water qs 100 g pH - 10.2
Au moment de l'emploi, on ajoute 100 g d'eau oxygénée à 20 volumes.At the time of use, 100 g of hydrogen peroxide are added to 20 volumes.
1818
Le mélange, appliqué 20 minutes à 28°C sur des cheveux naturellement blancs à 90%, leur confère, après shampooing et rinçage, une coloration blond foncé rosé.The mixture, applied 20 minutes at 28 ° C to naturally white hair at 90%, gives them, after shampooing and rinsing, a dark pinkish pink coloring.
EXEMPLE 10 o 5 On prépare le mélange tinctorial suivant : £Âmino-2y(|55-hydr oxyéthyl) amino-5 ,nitro-i]phényl-l propanol-2 0,08 gEXAMPLE 10 o 5 The following dye mixture is prepared: £ Amino-2y (| 55-hydr oxyethyl) amino-5, nitro-i] phenyl-1-propanol-2 0.08 g
Para-amdnophénol 0,09 gPara-amdnophenol 0.09 g
Dichlorhydrate de diamino-l,4,dimëthyl-2,6 benzène 0,04 g 20 Rêsorcine 0,06 g1,4-diamino dihydrochloride, 2,6-dimethyl benzene 0.04 g 20 Resorcinin 0.06 g
Dichlorhydrate de £amino-2(^9-hydroxyéthyl)amino-4^ phénoxy éthanol 0,05 g CELLOSIZE WP 03 2 g£ amino-2 (^ 9-hydroxyethyl) amino-4 ^ dihydrochloride phenoxy ethanol 0.05 g CELLOSIZE WP 03 2 g
Laurylsulfate d’ammonium 5 g 25 Butoxy-2 éthanol 15 gAmmonium lauryl sulfate 5 g 25 Butoxy-2 ethanol 15 g
Alcool à 96° 5 g96 ° alcohol 5 g
Ammoniaque â 22°Bé 10 gAmmonia at 22 ° Be 10 g
Thiolactate d’ammonium 0,8 gAmmonium thiolactate 0.8 g
Eau qsp 100 g 2o PH - 10,1Water qs 100 g 2o PH - 10.1
Au moment de l’emploi, on ajoute 120 g d’eau oxygénée à 20 volumes.At the time of use, 120 g of hydrogen peroxide are added to 20 volumes.
Le mélange, appliqué 40 minutes à 30°C sur des cheveux naturellement -blancs à 90%, leur confère, après shampooing et rinçage, une coloration gris clair nacré.The mixture, applied 40 minutes at 30 ° C to naturally-white hair at 90%, gives them, after shampooing and rinsing, a pearly light gray coloring.
/i y 19/ i y 19
Les différents noms commerciaux utilisés dans les exemples qui précèdent sont explicités plus en détail ci-après : ALFOL : Alcool cétylstéarylique vendu par laThe different trade names used in the above examples are explained in more detail below: ALFOL: Cetylstearyl alcohol sold by the
Société Condéa.Condéa company.
5 Cire de Lanette E : Alcool cétylstéarylique partiellement sulfaté vendu par Henkel.5 Lanette wax E: Partially sulfated cetylstearyl alcohol sold by Henkel.
CEMULSOL B : Huile de ricin ëthoxylée vendue parCEMULSOL B: Ethoxylated castor oil sold by
Rhône Poulenc.Rhône Poulenc.
CELLOSIZE WP 03 : Hydroxyëthylcellulose vendue par 10 UNION CARBIDE.CELLOSIZE WP 03: Hydroxyethylcellulose sold by 10 UNION CARBIDE.
LAURAMIDE : Monoêthanolamide d’acide laurique vendu par Witco.LAURAMIDE: Monoethanolamide of lauric acid sold by Witco.
ETHCMEEN TO 12 ; Olëylamine oxyëthylénée â 12 moles d’oxyde d’éthylène vendue par 15 AKMAK.ETHCMEEN TO 12; Oxylethylenated oleylamine containing 12 moles of ethylene oxide sold by 15 AKMAK.
COMPERLAN KD : Diéthanolamide d’acide gras de coprah vendu par HENKEL.COMPERLAN KD: Diethanolamide of coconut fatty acid sold by HENKEL.
MASQUOL DTPA : Sel pentasodique de l’acide diéthy- lène triamine pentacétique vendu par 20 PROTEX.MASQUOL DTPA: Pentasodium salt of diethylene triamine pentacetic acid sold by 20 PROTEX.
• 'CEMULSOL NP 4 : Nonylphénol oxyéthyléné à 4 moles d’oxyde d’éthylène vendu par RHONE-POULENC.• 'CEMULSOL NP 4: Nonylphenol oxyethylenated with 4 moles of ethylene oxide sold by RHONE-POULENC.
CEMULSOL NP 9 : Nonylphénol oxyéthyléné â 9 moles 25 d’oxyde d’éthylène vendu par RHONE- POULENC.CEMULSOL NP 9: Nonylphenol oxyethylenated to 9 moles of ethylene oxide sold by RHONE-POULENC.
i f CARBOPOL 934 : Polymère de l’acide acrylique de PMi f CARBOPOL 934: Polymer of PM acrylic acid
j 2 â 3 millions vendu par GOODRICHj 2 to 3 million sold by GOODRICH
I · CHEMICAL COMPANY.I · CHEMICAL COMPANY.
! 30 TRILON B : Acide éthylènediamine tétracétique.! 30 TRILON B: Ethylenediamine tetracetic acid.
i i | a t- i j ‘i i | has i i ‘
Claims (16)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU85681A LU85681A1 (en) | 1984-12-13 | 1984-12-13 | NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS AND IN PARTICULAR HUMAN HAIR |
| IT68043/85A IT1189605B (en) | 1984-12-13 | 1985-12-12 | 2 NITRO 4 AMINO 6 HYDROXIALKYLANILINS THEIR PREPARATION PROCEDURE AND THEIR USE IN THE DYING OF KERATINIC FIBERS IN PARTICULAR OF HUMAN HAIR |
| CH5315/85A CH669596A5 (en) | 1984-12-13 | 1985-12-12 | |
| BE1/216003A BE903845A (en) | 1984-12-13 | 1985-12-12 | NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, THEIR PREPARATION PROCESS AND THEIR USE IN DYEING KERATINIC FIBERS AND PARTICULARLY HUMAN HAIR. |
| DE19853543963 DE3543963A1 (en) | 1984-12-13 | 1985-12-12 | 2-NITRO-4-AMINO-6-HYDROXYALKYLANILINE, METHOD FOR THE PRODUCTION THEREOF AND COLOR CONTAINING THESE COMPOUNDS FOR KERATIN FIBERS AND IN PARTICULAR FOR HUMAN HAIR |
| FR8518404A FR2574789B1 (en) | 1984-12-13 | 1985-12-12 | NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS, AND PARTICULARLY HUMAN HAIR |
| CA000497634A CA1254908A (en) | 1984-12-13 | 1985-12-13 | 2-nitro-4-amino-6-hydroxyalkyl-anilines; process for preparing the same and their use for dyeing keratinic fibers and especially human hair |
| US06/808,814 US4727192A (en) | 1984-12-13 | 1985-12-13 | 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibers, and especially human hair |
| JP60280882A JPS61190565A (en) | 1984-12-13 | 1985-12-13 | Nitro-2, amino-4, hydroxy-6 aniline, manufacture and hair dye composition |
| GB08530759A GB2168371B (en) | 1984-12-13 | 1985-12-13 | New 2-nitro-4-amino anilines |
| US07/119,083 US4888445A (en) | 1984-12-13 | 1987-11-10 | New 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibres, and especially human hair |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU85681 | 1984-12-13 | ||
| LU85681A LU85681A1 (en) | 1984-12-13 | 1984-12-13 | NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS AND IN PARTICULAR HUMAN HAIR |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85681A1 true LU85681A1 (en) | 1986-07-17 |
Family
ID=19730368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85681A LU85681A1 (en) | 1984-12-13 | 1984-12-13 | NOVELS NITRO-2, AMINO-4, HYDROXYALKYL-6 ANILINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN DYEING KERATINIC FIBERS AND IN PARTICULAR HUMAN HAIR |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS61190565A (en) |
| BE (1) | BE903845A (en) |
| CA (1) | CA1254908A (en) |
| CH (1) | CH669596A5 (en) |
| DE (1) | DE3543963A1 (en) |
| FR (1) | FR2574789B1 (en) |
| GB (1) | GB2168371B (en) |
| IT (1) | IT1189605B (en) |
| LU (1) | LU85681A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4865987B2 (en) * | 2003-10-06 | 2012-02-01 | 花王株式会社 | Hair dye composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130871C (en) * | 1965-07-30 |
-
1984
- 1984-12-13 LU LU85681A patent/LU85681A1/en unknown
-
1985
- 1985-12-12 CH CH5315/85A patent/CH669596A5/fr not_active IP Right Cessation
- 1985-12-12 FR FR8518404A patent/FR2574789B1/en not_active Expired
- 1985-12-12 BE BE1/216003A patent/BE903845A/en not_active IP Right Cessation
- 1985-12-12 DE DE19853543963 patent/DE3543963A1/en not_active Withdrawn
- 1985-12-12 IT IT68043/85A patent/IT1189605B/en active
- 1985-12-13 CA CA000497634A patent/CA1254908A/en not_active Expired
- 1985-12-13 JP JP60280882A patent/JPS61190565A/en active Pending
- 1985-12-13 GB GB08530759A patent/GB2168371B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2574789A1 (en) | 1986-06-20 |
| CA1254908A (en) | 1989-05-30 |
| CH669596A5 (en) | 1989-03-31 |
| IT1189605B (en) | 1988-02-04 |
| GB2168371A (en) | 1986-06-18 |
| DE3543963A1 (en) | 1986-06-26 |
| FR2574789B1 (en) | 1988-10-14 |
| JPS61190565A (en) | 1986-08-25 |
| GB8530759D0 (en) | 1986-01-22 |
| BE903845A (en) | 1986-06-12 |
| IT8568043A0 (en) | 1985-12-12 |
| GB2168371B (en) | 1988-11-02 |
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