CH618343A5 - - Google Patents
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- Publication number
- CH618343A5 CH618343A5 CH820276A CH820276A CH618343A5 CH 618343 A5 CH618343 A5 CH 618343A5 CH 820276 A CH820276 A CH 820276A CH 820276 A CH820276 A CH 820276A CH 618343 A5 CH618343 A5 CH 618343A5
- Authority
- CH
- Switzerland
- Prior art keywords
- composition according
- formula
- amino
- methyl
- nitro
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
- 239000000975 dye Substances 0.000 claims description 44
- 239000002585 base Substances 0.000 claims description 42
- 230000003647 oxidation Effects 0.000 claims description 32
- 238000007254 oxidation reaction Methods 0.000 claims description 32
- 235000019441 ethanol Nutrition 0.000 claims description 31
- -1 monoalkyl-aminoalkyl Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 26
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 26
- 239000007800 oxidant agent Substances 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 239000000982 direct dye Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000004040 coloring Methods 0.000 claims description 17
- 230000001590 oxidative effect Effects 0.000 claims description 17
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 16
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000006210 lotion Substances 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- 239000002537 cosmetic Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 229920001897 terpolymer Polymers 0.000 claims description 5
- 239000003981 vehicle Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000000129 anionic group Chemical group 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
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 239000008135 aqueous vehicle Substances 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 235000011197 perejil Nutrition 0.000 claims description 2
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 241000208317 Petroselinum Species 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 51
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 19
- 229910052709 silver Inorganic materials 0.000 description 19
- 239000004332 silver Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- 210000000988 bone and bone Anatomy 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 14
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 12
- 239000012429 reaction media Substances 0.000 description 12
- XFXPUDGLXYMEBL-UHFFFAOYSA-N 3-amino-6-methyl-2-nitrophenol Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1O XFXPUDGLXYMEBL-UHFFFAOYSA-N 0.000 description 11
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 11
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 11
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 9
- 102000011782 Keratins Human genes 0.000 description 9
- 108010076876 Keratins Proteins 0.000 description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 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 8
- WELKBINNNXKQQS-UHFFFAOYSA-N 1,4-benzoquinone imine Chemical compound N=C1C=CC(=O)C=C1 WELKBINNNXKQQS-UHFFFAOYSA-N 0.000 description 7
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 7
- IRBDHDCSANDNFC-UHFFFAOYSA-N n-(3-hydroxy-4-methyl-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(O)=C1[N+]([O-])=O IRBDHDCSANDNFC-UHFFFAOYSA-N 0.000 description 7
- 150000002828 nitro derivatives Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 description 6
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 5
- DPVVNJKOVOHMGQ-UHFFFAOYSA-N 3-amino-6-chloro-2-nitrophenol Chemical compound NC1=CC=C(Cl)C(O)=C1[N+]([O-])=O DPVVNJKOVOHMGQ-UHFFFAOYSA-N 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- BLCZXLGRKKRKJJ-UHFFFAOYSA-N 3-amino-2-nitrophenol Chemical compound NC1=CC=CC(O)=C1[N+]([O-])=O BLCZXLGRKKRKJJ-UHFFFAOYSA-N 0.000 description 4
- AWDKQDCYEIIDKA-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CONC1=CC=C(N)C=C1 AWDKQDCYEIIDKA-UHFFFAOYSA-N 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 4
- 244000038561 Modiola caroliniana Species 0.000 description 4
- 235000010703 Modiola caroliniana Nutrition 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 241000083869 Polyommatus dorylas Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- GHYDMJFKTBCMGR-UHFFFAOYSA-N ethyl n-(3-hydroxy-4-methyl-2-nitrophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(C)C(O)=C1[N+]([O-])=O GHYDMJFKTBCMGR-UHFFFAOYSA-N 0.000 description 4
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HQHZFBHHZQINAK-UHFFFAOYSA-N 1,2,3,4-tetraaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=C(N)C(N)=C3C(=O)C2=C1 HQHZFBHHZQINAK-UHFFFAOYSA-N 0.000 description 3
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCDBMAGIBIBYQN-UHFFFAOYSA-N 2-[carboxy(phenyl)methoxy]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OC(C(O)=O)C1=CC=CC=C1 ZCDBMAGIBIBYQN-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 3
- LXYNBTGFURMNAB-UHFFFAOYSA-N 6-methyl-3-(methylamino)-2-nitrophenol Chemical compound CNC1=CC=C(C)C(O)=C1[N+]([O-])=O LXYNBTGFURMNAB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000001543 Corylus americana Nutrition 0.000 description 3
- 235000007466 Corylus avellana Nutrition 0.000 description 3
- 244000178870 Lavandula angustifolia Species 0.000 description 3
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 3
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 3
- 244000086363 Pterocarpus indicus Species 0.000 description 3
- 235000009984 Pterocarpus indicus Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- DQPBABKTKYNPMH-UHFFFAOYSA-M amino sulfate Chemical compound NOS([O-])(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 3
- 239000001102 lavandula vera Substances 0.000 description 3
- 235000018219 lavender Nutrition 0.000 description 3
- FMEJKACEWHCCNV-UHFFFAOYSA-N methoxy hydrogen sulfate Chemical compound COOS(O)(=O)=O FMEJKACEWHCCNV-UHFFFAOYSA-N 0.000 description 3
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- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- JOWPOHZYWVVXGZ-UHFFFAOYSA-N n-(2-anilinoethyl)acetamide Chemical compound CC(=O)NCCNC1=CC=CC=C1 JOWPOHZYWVVXGZ-UHFFFAOYSA-N 0.000 description 1
- GDVBIJQRIMRQLF-UHFFFAOYSA-N n-(3-hydroxy-2-nitro-4-propanoylphenyl)acetamide Chemical compound CCC(=O)C1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1O GDVBIJQRIMRQLF-UHFFFAOYSA-N 0.000 description 1
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N n-(4-aminophenyl)nitramide Chemical class NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 description 1
- SZYJOHLOFGFXSF-UHFFFAOYSA-N n-(4-chloro-3-hydroxy-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C(O)=C1[N+]([O-])=O SZYJOHLOFGFXSF-UHFFFAOYSA-N 0.000 description 1
- FWPNOLFNLHAULD-UHFFFAOYSA-N n-(4-chloro-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C(O)=C1 FWPNOLFNLHAULD-UHFFFAOYSA-N 0.000 description 1
- AIYFITVQMIFCGJ-UHFFFAOYSA-N n-(5-hydroxy-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(O)=CC=C1[N+]([O-])=O AIYFITVQMIFCGJ-UHFFFAOYSA-N 0.000 description 1
- VUJKKJZZVFVUTD-UHFFFAOYSA-N n-(5-hydroxy-4-methyl-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(O)=C(C)C=C1[N+]([O-])=O VUJKKJZZVFVUTD-UHFFFAOYSA-N 0.000 description 1
- SXHIEJQAGMGCQR-UHFFFAOYSA-N n-methylaniline;sulfuric acid Chemical compound OS(O)(=O)=O.CNC1=CC=CC=C1 SXHIEJQAGMGCQR-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 150000004060 quinone imines Chemical class 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000011031 topaz Substances 0.000 description 1
- 229910052853 topaz Inorganic materials 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/418—Amines containing nitro groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7520155A FR2315256A1 (fr) | 1975-06-26 | 1975-06-26 | Coupleurs nitres utilisables en teintures directes, teintures d'oxydation et teintures mixtes |
| FR7534208A FR2330673A1 (fr) | 1975-11-07 | 1975-11-07 | Coupleurs nitres utilisables en teintures directes, teintures d'oxydation et teintures mixtes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618343A5 true CH618343A5 (en, 2012) | 1980-07-31 |
Family
ID=26218946
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH820276A CH618343A5 (en, 2012) | 1975-06-26 | 1976-06-25 | |
| CH1084079A CH621537A5 (en, 2012) | 1975-06-26 | 1979-12-06 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1084079A CH621537A5 (en, 2012) | 1975-06-26 | 1979-12-06 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4330291A (en, 2012) |
| JP (1) | JPS523836A (en, 2012) |
| AU (1) | AU498883B2 (en, 2012) |
| CA (1) | CA1088066A (en, 2012) |
| CH (2) | CH618343A5 (en, 2012) |
| DE (2) | DE2661057C2 (en, 2012) |
| GB (1) | GB1544127A (en, 2012) |
| IT (1) | IT1070051B (en, 2012) |
| NL (1) | NL182534C (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2430932A1 (fr) * | 1978-07-12 | 1980-02-08 | Oreal | Metaphenylenediamines et compositions tinctoriales les contenant |
| DE3016008A1 (de) * | 1980-04-25 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Neue kupplerkomponenten fuer oxidationshaarfarben, deren herstellung und verwendung, sowie diese enthaltende haarfaerbemittel |
| DE3038284C2 (de) * | 1980-10-10 | 1985-08-22 | Wella Ag, 6100 Darmstadt | Mittel und Verfahren zur oxidativen Färbung von Haaren |
| LU83686A1 (fr) * | 1981-10-08 | 1983-06-08 | Oreal | Composition tinctoriale pour fibres keratiniques a base de colorants nitres benzeniques |
| DE3301398A1 (de) * | 1983-01-18 | 1984-07-19 | Chemische Fabrik Kalk GmbH, 5000 Köln | Verfahren zur herstellung von soda aus den bei der aufarbeitung von kalirohsalzen anfallenden rueckstaenden |
| DE3302817A1 (de) * | 1983-01-28 | 1984-08-02 | Hans Schwarzkopf Gmbh, 2000 Hamburg | Substituierte 4-amino-3-nitrophenole, verfahren zu ihrer herstellung sowie haarfaerbemittel, die diese enthalten |
| DE3413693A1 (de) * | 1984-04-11 | 1985-10-17 | Boehringer Mannheim Gmbh, 6800 Mannheim | Fluorierte anilinderivate und ihre verwendung |
| EP0178413A1 (en) * | 1984-08-17 | 1986-04-23 | Beecham Group Plc | Benzimidazoles |
| CA1331143C (en) * | 1986-10-27 | 1994-08-02 | Farouk M. Shami | Method for lightening and permanently coloring hair |
| EP0352285B1 (en) * | 1987-03-25 | 1994-12-28 | Commonwealth Scientific And Industrial Research Organisation | Process for dyeing wool and other keratin fibres |
| FR2628104B1 (fr) * | 1988-03-03 | 1990-07-27 | Oreal | Para-aminophenols 3-substitues, leur procede de preparation, leur utilisation pour la teinture des fibres keratiniques et les composes intermediaires utilises dans le procede de preparation |
| JPH0720852B2 (ja) * | 1988-06-08 | 1995-03-08 | 花王株式会社 | 角質繊維用染色組成物 |
| US4980158A (en) * | 1989-04-04 | 1990-12-25 | Clairol Incorporated | Nitroaniline dyes with a cyano substituent group |
| JP2843938B2 (ja) * | 1989-07-19 | 1999-01-06 | 日東電工株式会社 | 導電性有機重合体組成物フイルム及びその製造方法 |
| DE4011481A1 (de) * | 1990-04-09 | 1991-10-10 | Henkel Kgaa | Oxidationsfaerbemittel |
| US5078749A (en) * | 1990-07-19 | 1992-01-07 | Clairol, Inc. | Nitroso compounds as direct dyes |
| US5000755A (en) * | 1990-07-19 | 1991-03-19 | Clairol Incorporated | Nitroso compounds as direct dyes |
| US5628799A (en) * | 1991-09-26 | 1997-05-13 | Clairol Incorporated | Hair dying methods and kits which contain a dopa species, reactive direct dye, and a ferricyanide oxidant |
| KR100276113B1 (ko) * | 1992-05-15 | 2000-12-15 | 죤엠.산드레 | 가속 초임계 유체 추출법 |
| JPH07508886A (ja) * | 1992-07-10 | 1995-10-05 | ノバテック，インク． | シリカコロイド含有味増進剤並びにその製造法と使用法 |
| US5607667A (en) * | 1993-06-11 | 1997-03-04 | Novatech, Inc. | Body care compositions, method of using same, and method of generating a relatively stable aqueous suspension of colloidal silica for use therein |
| FR2713927B1 (fr) * | 1993-12-22 | 1996-01-19 | Oreal | Procédé de coloration directe des fibres kératiniques humaines à l'aide de vapeur d'eau. |
| FR2753093B1 (fr) * | 1996-09-06 | 1998-10-16 | Oreal | Composition de teinture d'oxydation pour fibres keratiniques comprenant un polymere amphiphile anionique |
| US6187058B1 (en) * | 1998-05-20 | 2001-02-13 | Combe, Inc., | Low water no volatile organic compound hair lightener and dyeing composition |
| US20060026773A1 (en) * | 2004-02-27 | 2006-02-09 | Stephane Sabelle | Ortho-and/or meta-substituted N-alkylamino secondary para-phenylenediamine, composition for dyeing keratin fibers containing such a para-phenylenediamine, processes using this composition and uses thereof |
| US7338536B2 (en) * | 2004-02-27 | 2008-03-04 | L'oreal S. A. | N-alkylamino secondary para-phenylenediamine, composition for dyeing keratin fibers comprising such a para-phenylenediamine, processes using this composition and uses thereof |
| FR2866875A1 (fr) * | 2004-02-27 | 2005-09-02 | Oreal | Para-phenylenediamine secondaire n-alkylhydroxylee ortho- et/ou meta-substituee, composition de teinture des fibres keratiniques contenant une telle para-phenylenediamine, procedes mettant en oeuvre cette composition et utilisations |
| FR2866874B1 (fr) * | 2004-02-27 | 2007-10-12 | Oreal | Para-phenylenediamine secondaire n-alkylhydroxylee, composition de teinture des fibres keratiniques contenant une telle para-phenylenediamine, procedes mettant en oeuvre cette composition et utilisations |
| US7435268B2 (en) * | 2004-02-27 | 2008-10-14 | L'oreal S.A. | N-alkylhydroxylated secondary para-phenylenediamine compounds, composition for dyeing keratin fibers comprising the same, and dyeing processes using the composition |
| US7445645B2 (en) * | 2004-02-27 | 2008-11-04 | L'oreal S.A. | Ortho-and/or meta-substituted N-alkylhydroxylated secondary para-phenylenediamine compounds, compositions for dyeing keratin fibers comprising such compounds, and processes of dyeing therewith |
| CN104168876B (zh) | 2012-03-27 | 2017-11-03 | 诺赛尔股份有限公司 | 包含3‑氨基‑2,6‑二甲基苯酚和1,4‑苯二胺型显色剂的毛发着色剂组合物、方法以及包含所述组合物的套盒 |
| EP2830579B1 (en) | 2012-03-27 | 2020-02-26 | Noxell Corporation | Hair colorant compositions comprising 3-amino 2,6 dimethylphenol, methods, and kits comprising the compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE928909C (de) * | 1951-02-07 | 1955-06-13 | Kleinol Produktion G M B H | Verfahren zum Faerben von tierischen Fasern, insbesondere von menschlichen Haaren, ohne Zuhilfenahme von Oxydationsmitteln |
| GB889327A (en) * | 1958-04-10 | 1962-02-14 | Gillette Industries Ltd | Improvements in or relating to shampoo compositions |
| US3488138A (en) * | 1962-10-18 | 1970-01-06 | Clairol Inc | Stabilized nitro-aminobenzene dyeing compositions |
-
1976
- 1976-06-25 DE DE2661057A patent/DE2661057C2/de not_active Expired
- 1976-06-25 DE DE19762628716 patent/DE2628716A1/de active Granted
- 1976-06-25 NL NLAANVRAGE7606948,A patent/NL182534C/xx not_active IP Right Cessation
- 1976-06-25 CA CA255,711A patent/CA1088066A/fr not_active Expired
- 1976-06-25 CH CH820276A patent/CH618343A5/fr not_active IP Right Cessation
- 1976-06-25 JP JP51075408A patent/JPS523836A/ja active Granted
- 1976-06-25 AU AU15303/76A patent/AU498883B2/en not_active Expired
- 1976-06-25 IT IT7668575A patent/IT1070051B/it active
- 1976-06-25 GB GB26586/76A patent/GB1544127A/en not_active Expired
-
1979
- 1979-12-06 CH CH1084079A patent/CH621537A5/fr not_active IP Right Cessation
-
1980
- 1980-03-05 US US06/127,461 patent/US4330291A/en not_active Expired - Lifetime
-
1982
- 1982-02-22 US US06/351,300 patent/US4473374A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4330291A (en) | 1982-05-18 |
| JPS523836A (en) | 1977-01-12 |
| NL182534C (nl) | 1988-04-05 |
| AU498883B2 (en) | 1979-03-29 |
| DE2661057C2 (en, 2012) | 1988-08-04 |
| GB1544127A (en) | 1979-04-11 |
| DE2628716A1 (de) | 1977-01-20 |
| DE2628716C2 (en, 2012) | 1988-06-16 |
| NL7606948A (nl) | 1976-12-28 |
| NL182534B (nl) | 1987-11-02 |
| IT1070051B (it) | 1985-03-25 |
| JPS6234752B2 (en, 2012) | 1987-07-28 |
| CH621537A5 (en, 2012) | 1981-02-13 |
| AU1530376A (en) | 1978-01-26 |
| US4473374A (en) | 1984-09-25 |
| CA1088066A (fr) | 1980-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |