JP5431735B2 - ケラチン繊維の明色化及び染色を同時に行うための薬剤の使用 - Google Patents
ケラチン繊維の明色化及び染色を同時に行うための薬剤の使用 Download PDFInfo
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- JP5431735B2 JP5431735B2 JP2008551946A JP2008551946A JP5431735B2 JP 5431735 B2 JP5431735 B2 JP 5431735B2 JP 2008551946 A JP2008551946 A JP 2008551946A JP 2008551946 A JP2008551946 A JP 2008551946A JP 5431735 B2 JP5431735 B2 JP 5431735B2
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- Prior art keywords
- ethyl
- amino
- phenyl
- diazenyl
- bromide
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- 239000000835 fiber Substances 0.000 title claims abstract description 15
- 102000011782 Keratins Human genes 0.000 title claims abstract description 11
- 108010076876 Keratins Proteins 0.000 title claims abstract description 11
- 239000003814 drug Substances 0.000 title description 5
- 229940079593 drug Drugs 0.000 title description 2
- 239000000987 azo dye Substances 0.000 claims abstract description 19
- 125000002091 cationic group Chemical group 0.000 claims abstract description 19
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- -1 4-Methyl-1,3-thiazol-2-yl Chemical group 0.000 claims description 40
- 239000007800 oxidant agent Substances 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- 238000004043 dyeing Methods 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- ULIPQUITJRPDOM-UHFFFAOYSA-M 2-[4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(C)=C(C)S1 ULIPQUITJRPDOM-UHFFFAOYSA-M 0.000 claims description 7
- 239000000982 direct dye Substances 0.000 claims description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- HLEDRXAXXSBBAI-UHFFFAOYSA-M 2-[4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-n-ethyl-3-methylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].CC1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(C)=C(C)S1 HLEDRXAXXSBBAI-UHFFFAOYSA-M 0.000 claims description 3
- 241001024304 Mino Species 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- ZLPSDWNPNIZOCC-UHFFFAOYSA-M 2-[3-chloro-4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].ClC1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(C)=C(C)S1 ZLPSDWNPNIZOCC-UHFFFAOYSA-M 0.000 claims description 2
- ATRVWDYCSVLEAJ-UHFFFAOYSA-M 2-[3-chloro-n-ethyl-4-[(4-methyl-1,3-thiazol-2-yl)diazenyl]anilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].ClC1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(C)=CS1 ATRVWDYCSVLEAJ-UHFFFAOYSA-M 0.000 claims description 2
- FLWISULAZDLJDX-UHFFFAOYSA-M 2-[4-[(3-chloro-1,2,4-thiadiazol-5-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(Cl)=NS1 FLWISULAZDLJDX-UHFFFAOYSA-M 0.000 claims description 2
- MDSIYMGUKYDHAS-UHFFFAOYSA-M 2-[4-[(4,6-dinitro-1,3-benzothiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C2S1 MDSIYMGUKYDHAS-UHFFFAOYSA-M 0.000 claims description 2
- HSTYJWUBIWNFET-UHFFFAOYSA-M 2-[N-ethyl-4-(1H-1,2,4-triazol-5-yldiazenyl)anilino]ethyl-trimethylazanium bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC=NN1 HSTYJWUBIWNFET-UHFFFAOYSA-M 0.000 claims description 2
- AFTRFOXDRNDJGD-UHFFFAOYSA-M 2-[n-ethyl-4-[(4-methyl-1,3-thiazol-2-yl)diazenyl]anilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(C)=CS1 AFTRFOXDRNDJGD-UHFFFAOYSA-M 0.000 claims description 2
- KMXKZFJYGMLVLJ-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=CC=C([N+]([O-])=O)C=C2S1 KMXKZFJYGMLVLJ-UHFFFAOYSA-M 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 229910021538 borax Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 2
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 2
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims description 2
- ZTEHHVGUEGZCJX-UHFFFAOYSA-M 2-[4-(1,3-benzothiazol-2-yldiazenyl)-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=CC=CC=C2S1 ZTEHHVGUEGZCJX-UHFFFAOYSA-M 0.000 claims 1
- BXZMAQWYHDUNPH-UHFFFAOYSA-M 2-[4-[(4-chloro-6-nitro-1,3-benzothiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=C(Cl)C=C([N+]([O-])=O)C=C2S1 BXZMAQWYHDUNPH-UHFFFAOYSA-M 0.000 claims 1
- INKSLKMINANXRS-UHFFFAOYSA-M 2-[4-[(5-chloro-[1,3]thiazolo[5,4-b]pyridin-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=CC=C(Cl)N=C2S1 INKSLKMINANXRS-UHFFFAOYSA-M 0.000 claims 1
- RJLQZHQTZWMYSF-UHFFFAOYSA-M 2-[n-ethyl-4-(1,3-thiazol-2-yldiazenyl)anilino]ethyl-dimethyl-phenylazanium;bromide Chemical compound [Br-].C=1C=C(N=NC=2SC=CN=2)C=CC=1N(CC)CC[N+](C)(C)C1=CC=CC=C1 RJLQZHQTZWMYSF-UHFFFAOYSA-M 0.000 claims 1
- LCBNQKRMMOYOMI-UHFFFAOYSA-M 2-[n-ethyl-4-[(4-methyl-6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=C(C)C=C([N+]([O-])=O)C=C2S1 LCBNQKRMMOYOMI-UHFFFAOYSA-M 0.000 claims 1
- CGLWCPDRJVXJKV-UHFFFAOYSA-M 2-[n-ethyl-4-[(5-methoxy-[1,3]thiazolo[5,4-b]pyridin-2-yl)diazenyl]anilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=CC=C(OC)N=C2S1 CGLWCPDRJVXJKV-UHFFFAOYSA-M 0.000 claims 1
- JSBSEGNPJCABGK-UHFFFAOYSA-M 4-[n-ethyl-3-methyl-4-[(1-methylimidazol-2-yl)diazenyl]anilino]butan-2-yl-trimethylazanium;bromide Chemical compound [Br-].CC1=CC(N(CCC(C)[N+](C)(C)C)CC)=CC=C1N=NC1=NC=CN1C JSBSEGNPJCABGK-UHFFFAOYSA-M 0.000 claims 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims 1
- 239000000980 acid dye Substances 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 239000000981 basic dye Substances 0.000 claims 1
- 239000001005 nitro dye Substances 0.000 claims 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 abstract description 6
- 210000004209 hair Anatomy 0.000 description 42
- 239000000203 mixture Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000118 hair dye Substances 0.000 description 18
- 230000001590 oxidative effect Effects 0.000 description 17
- 239000003086 colorant Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000002516 radical scavenger Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000001099 ammonium carbonate Substances 0.000 description 6
- 125000004404 heteroalkyl group Chemical group 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000003113 alkalizing effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- XYTUTNQRQLAZLK-UHFFFAOYSA-N 4,5-dimethyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.CC=1N=C(N)SC=1C XYTUTNQRQLAZLK-UHFFFAOYSA-N 0.000 description 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- JDRSMPFHFNXQRB-CMTNHCDUSA-N Decyl beta-D-threo-hexopyranoside Chemical compound CCCCCCCCCCO[C@@H]1O[C@H](CO)C(O)[C@H](O)C1O JDRSMPFHFNXQRB-CMTNHCDUSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 3
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 3
- 235000012501 ammonium carbonate Nutrition 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 238000006149 azo coupling reaction Methods 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940073499 decyl glucoside Drugs 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical class [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
- UOFGSWVZMUXXIY-UHFFFAOYSA-N 1,5-Diphenyl-3-thiocarbazone Chemical compound C=1C=CC=CC=1N=NC(=S)NNC1=CC=CC=C1 UOFGSWVZMUXXIY-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
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- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- SHNIKUXMZFPPCS-UHFFFAOYSA-N chembl1433124 Chemical compound OC1=CC(O)=CC=C1N=NC1=NC=CS1 SHNIKUXMZFPPCS-UHFFFAOYSA-N 0.000 description 1
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SKQBQIHCZOXMMV-UHFFFAOYSA-M diethyl-[2-[n-ethyl-4-(1,3-thiazol-2-yldiazenyl)anilino]ethyl]-methylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(CC)CC)CC)=CC=C1N=NC1=NC=CS1 SKQBQIHCZOXMMV-UHFFFAOYSA-M 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HAECXVUPWKTFLJ-UHFFFAOYSA-N dimethyl-[3-[[4-(methylamino)-9,10-dioxoanthracen-1-yl]amino]propyl]-propylazanium;bromide Chemical compound [Br-].O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NCCC[N+](C)(C)CCC HAECXVUPWKTFLJ-UHFFFAOYSA-N 0.000 description 1
- AAEAIKHSRKUDGH-UHFFFAOYSA-N dimethyl-[3-[[4-(methylamino)-9,10-dioxoanthracen-1-yl]amino]propyl]-propylazanium;chloride Chemical compound [Cl-].O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NCCC[N+](C)(C)CCC AAEAIKHSRKUDGH-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 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
- 150000002337 glycosamines Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000004919 hair shaft Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- KDNFLUWYIMPBSA-UHFFFAOYSA-N hydrogen peroxide;1,3,5-triazine-2,4,6-triamine Chemical compound OO.NC1=NC(N)=NC(N)=N1 KDNFLUWYIMPBSA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- LLLILZLFKGJCCV-UHFFFAOYSA-M n-methyl-n-[(1-methylpyridin-1-ium-4-yl)methylideneamino]aniline;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=CC=CC=1N(C)\N=C\C1=CC=[N+](C)C=C1 LLLILZLFKGJCCV-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229950004354 phosphorylcholine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- OESSQZSTPKCQOE-UHFFFAOYSA-M sodium;2,4-dinitronaphthalen-1-olate Chemical compound [Na+].C1=CC=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 OESSQZSTPKCQOE-UHFFFAOYSA-M 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
-
- 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
Landscapes
- 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)
Description
国際公開特許WO95/01722 A1及びWO97/20545 A1ではカチオン性アゾ染料を含む着色剤を開示し、カチオン性アゾ染料中では正電荷が共役系で非局在化している。カチオン性染料は、その中の側鎖において正電荷を局在化していて、例えば、欧州特許EP56578に記載のように、合成繊維を染色することが知られている。ドイツ特許DE10118271 A1では、数ある中でも、カチオン的にジアゾジアゾール化する(cationic disazodiazole)誘導体及びそれらの染毛剤への利用を開示している。
2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]−3−メチルフェニル}(エチル)−アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{3−クロロ−4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4−メチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4−メチル−1,3−チアゾール−2−イル)ジアゼニル]−3−メチルフェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{3−クロロ−4−[(4−メチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(1,3−ベンゾチアゾール−2−イルジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[(6−ニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[(4−[(5,6−ジニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[(4−[(4,6−ジニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−エチル{4−[(4−メチル−6−ニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[(4−[(4−クロロ−6−ニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[1H[1,3]チアゾロ[5,4−f]インダゾール−6−イルジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[5−クロロ[1,3]チアゾロ[5,4−b]ピリジン−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[5−メチル[1,3]チアゾロ[5,4−b]ピリジン−2−イル)ジアゼニル]−フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、N,N−ジエチル−2−(エチル{4−[1,3−チアゾール−2−イルジアゼニル]フェニル}アミノ)−N−メチルエタナミニウムブロミド、N−[2−(エチル{4−[1,3−チアゾール−2−イルジアゼニル]フェニル}アミノ)エチル]−N,N,−ジメチルベンゼナミニウムブロミド、2−(エチル{4−[1,2,4−チアジアゾール−5−イルジアゼニル]フェニル}アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[(3−フェニル−1,2,4−チアジアゾール−5−イル)ジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(3−クロロ−1,2,4−チアジアゾール−5−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[1H−1,2,4−トリアゾール−5−イルジアゼニル]フェニル}−アミノ)−N,N,N−トリメチルエタナミニウムブロミド、1−[2−(エチル{4−[(1−メチル−1H−イミダゾール]−2−イル)ジアゼニル]−フェノール}アミノ)エチル]−N,N,N−トリメチルエタナミニウムブロミド、1−[2−(エチル{3−メチル−4−[(1−メチル−1H−イミダゾール−2−イル)ジアゼニル]フェニル}アミノ)エチル]−N,N,N−トリメチルエタナミニウムブロミド、及び1−{2−[{3−クロロ−4−[(1−メチル−1H−イミダゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]エチル}−N,N,N−トリメチルエタナミニウムブロミドから選択される。
本発明による組成物は、少なくとも1つの酸化剤供給源を含んでもよい。本明細書に用いるのに好ましい酸化剤は、水溶性過酸素酸化剤である。本明細書で定義するとき、「水溶性」とは、標準状態で少なくとも0.1g、好ましくは1g、より好ましくは10gの前記酸化剤を1リットルの脱イオン水に溶解できることを意味する。酸化剤は、初期可溶化及びメラニンの脱色(脱色)に有用であり、毛幹中での酸化染料前駆体の酸化(酸化染色)を促進する。
本発明によると、前記組成物は、必要に応じて、少なくとも1つのアルカリ化剤、好ましくはアンモニウムイオン及び又はアンモニアの供給源を更に含んでも良い。アルカノールアミド類、例えばモノエタノールアミン、ジエタノールアミン、トリエタノールアミン、モノプロパノールアミン、ジプロパノールアミン、トリプロパノールアミン、2−アミノ−2−メチル−1,3−プロパンジオール、2−アミノ−2−メチル−1プロパノール、並びに2−アミノ−2−ヒドロキシメチル−1,3−プロパンジオール及びグアニジウム塩類のような当該技術分野において既知のいかなる剤を用いてもよい。特に、好ましいアルカリ化剤は、アンモニウムイオンの供給源を与えるものである。いずれのアンモニウムイオン供給源も本明細書で用いるのに好適である。好ましい供給源としては、塩化アンモニウム、硫酸アンモニウム、硝酸アンモニウム、リン酸アンモニウム、酢酸アンモニウム、炭酸アンモニウム、炭酸水素アンモニウム、カルバミン酸アンモニウム、水酸化アンモニウム、過炭酸塩、アンモニア、及びこれらの混合物が挙げられる。特に好ましいのは、炭酸アンモニウム、カルバミン酸アンモニウム、炭酸水素アンモニウム、アンモニア、及びこれらの混合物である。本発明の組成物は、約0.1重量%〜約10重量%、好ましくは約0.5重量%〜約5重量%、最も好ましくは約1重量%〜約3重量%のアルカリ化剤、好ましくはアンモニウムイオンを含んでもよい。
本発明によれば、組成物は、ラジカルスカベンジャー供給源を更に含んでもよい。本明細書で使用する時、「ラジカルスカベンジャー」という用語は、反応性ラジカル、好ましくは炭酸塩ラジカル類と反応して、前記反応性ラジカルを一連の高速反応によって、より反応性の低い種に変換させることのできる種を指す。
式中、YはNR2、O、又はS、好ましくはNR2であり、nは0〜2であり、R4は一価又は二価であって、次の、(i)置換若しくは非置換の直鎖状若しくは分枝状のアルキル系、モノ不飽和若しくはポリ不飽和アルキル系、ヘテロアルキル系、脂肪族系、ヘテロ脂肪族系、又はヘテロオレフィン系、(ii)置換若しくは非置換の単環式若しくは多環式の脂肪族系、アリール系、又は複素環式系、或いは(iii)置換若しくは非置換のモノフルオロ、ポリフルオロ若しくはペルフルオロアルキル系、から選択される。(i)、(ii)及び(iii)の系は、炭素原子1〜12個と、O、S、N、P並びにSiから選択される0〜5個のヘテロ原子とを含み、且つR4はR3又はR5に結合して5、6、若しくは7員環を形成でき、且つ式中、R1、R2、R3、R5、及びR6は一価であり本明細書の上記の(i),(ii)及び(iii)又はH、から独立して選択される。
若しくは分枝状のアルキル系、モノ不飽和若しくはポリ不飽和アルキル系、ヘテロアルキル系、脂肪族系、ヘテロ脂肪族系、又はヘテロオレフィン系、置換若しくは非置換の単環式若しくは多環式脂肪族系、アリール系、又は複素環式、又は置換若しくは非置換のモノフルオロ、ポリフルオロ若しくはペルフルオロアルキル系、から構成され、前記系は1〜10個の炭素原子及びO、S、N、P、並びにSiから選択される0〜5個のヘテロ原子を含む。(ii)はS結合型の一価の置換基の群であって、SA1、SCN、SO2A1、SO3A1、SSA1、SOA1、SO2NA1A2、SNA1A2、及びSONA1A2の置換基から構成される。(iii)はO結合型の一価の置換基の群であって、OA1、OCN及びONA1A2の置換基から構成される。(iv)はN結合型の一価の置換基の群であって、NA1A2、(NA1A2A3)+、NC、NA1OA2、NA1SA2、NCO、NCS、NO2、N=NA1、N=NOA1、NA1CN、NA1NA2A3の置換基から構成される。(v)は一価の置換基の群であって、COOA1、CON3、CONA1 2、CONA1COA2、C(=NA1)NA1A2、CHO、CHS、CN、NC、及びXの置換基から構成される。さらに(vi)は、1〜12個の炭素原子及び0〜4個のヘテロ原子を含むモノフルオロ、ポリフルオロ若しくはペルフルオロアルキル系から成る群である。
実施例1a2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)−アミノ]−N,N,N−トリメチルエタナミニウムブロミド(標準的アゾカップリング方式)
11.5g(69.6ミリモル)の2−アミノ−4,5−ジメチル−1,3−チアゾールハイドロクロライドを300mLの酢酸及び10.2gの濃硫酸の混合物に、温度を30℃まで高めながら、溶解した。混合物を15℃に冷却し、続いて33.2g(104.4ミリモル)の40%水性ニトロシル硫酸を滴下式で添加し1.5時間攪拌した。別のビーカー中で、20g(69.6ミリモル)の2−[エチル(フェニル)アミノ]−N,N,N−トリメチルエタナミニウムブロミドの80mLの酢酸、8.3gの塩酸(32%)及び120gの氷の溶液を調製した。先に調製したジアゾニウム塩溶液をこの溶液に、温度が5℃を超えないようにゆっくり添加した。その溶液を室温で2時間更に攪拌した。適切な量の30%水酸化ナトリウム水溶液を添加してpH値を4に調節した。得られた沈殿物をろ過し、水で洗浄し、40℃で真空乾燥した。エタノール/水中で再結晶し、赤色結晶として20.3g(理論の68%)の2−[{4−[{4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミドを得た。
1H NMR(300MHz、DMSO):δ=7.78(d、J=9.3、2H、H(3)及びH(5)−フェニル)、6.94(d、J=9.3、2H、H(2)及びH(6)−フェニル)、3.91(m、2H、N+CH2)、3.55(m、4H、2×NCH2)、3.21(s、9H、3×CH3)、2.38(s、3H、CH3)、2.32(s、3H、CH3)、1.19(t、J=6.9、3H、CH3)。
FAB−MS:346[M+](100)
1H NMR(300MHz、DMSO):δ=7.70(d、J=9.0、1H、H(5)−フェニル)、6.77(dd、J=9.0、J=2.7,1H、H(6)−フェニル)、6.75(d、J=2.7、1H、H(2)−フェニル)、3.90(m、2H、N+CH2)、3.52(m、4H、2×NCH2)、3.21(s、9H、3×CH3)、2.57(s、3H、CH3)、2.37(s、3H、CH3)、2.31(s、3H、CH3)、1.18(t、J=6.9、3H、CH3)。
2−[{3−クロロ−4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)−アミノ]−N,N,N−トリメチルエタナミニウムメチル硫酸塩を44%収率で得た。
1H NMR(300MHz、DMSO):δ=7.78(d、J=9.3、1H、H(5)−フェニル)、7.00(d、J=2.4、1H、H(2)−フェニル)、6.90(dd、J=9.0、J=2.7、1H、H(6)−フェニル)、3.92(m、2H、N+CH2)、3.55(m、4H、2×NCH2)、3.19(s、9H、3×CH3)、2.39(s、3H、CH3)、2.33(s、3H、CH3)、1.18(t、J=6.9、3H、CH3)。
0.33g 表1によるカチオン性アゾ染料
5.0g エタノール
4.0g デシルグリコシド
0.2g エチレンジアミン四酢酸2ナトリウム塩
脱イオンした水、100.0g、添加
0.66g 表2によるカチオン性アゾ染料
5.0g エタノール
4.0g デシルグルコシド
0.2g エチレンジアミン四酢酸2ナトリウム塩
脱イオン水、100.0g、添加
染色結果を、下記表2にまとめた。
0.33g 表3によるカチオン性アゾ染料
5.0g エタノール
4.0g デシルグルコシド
0.2g エチレンジアミン四酢酸2ナトリウム塩
脱イオン水、100g、添加
得られた使用準備の整った(ready-to-use)染毛剤を、地毛(L=34.24、C=14.62、h=66.7)に適用し、ブラシを使用して均一に広げる。40℃にて30分の接触時間後、毛髪をぬるま湯ですすぎ、シャンプーで洗浄し、ぬるま湯ですすいだ後、乾燥させる。前記洗浄プロセスを、5回繰り返した。色は、視覚的には変化しない。
0.66g 表4によるカチオン性アゾ染料
5.0g エタノール
4.0g デシルグルコシド
0.2g エチレンジアミン四酢酸2ナトリウム塩
脱イオン水、100g、添加
0.33g 2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)−アミノ]−N,N,N−トリメチルエタナミニウムブロミド(1a)
5.00g エタノール
4.00g セチルトリメチルアンモニウムクロライド、25%水溶液
脱イオン水、100.00g、添加
0.33g 2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)−アミノ]−N,N,N−トリメチルエタナミニウムブロミド(1a)
5.00g エタノール
7.50g ココナツ脂肪酸アミドプロピルベタイン
脱イオン水、100g、添加
Claims (4)
- 少なくとも1つの酸化剤と、2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]−3−メチルフェニル}(エチル)−アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{3−クロロ−4−[(4,5−ジメチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4−メチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4−メチル−1,3−チアゾール−2−イル)ジアゼニル]−3−メチルフェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{3−クロロ−4−[(4−メチル−1,3−チアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[1,3−ベンゾチアゾール−2−イルジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[(6−ニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(5,6−ジニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4,6−ジニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[(4−メチル−6−ニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(4−クロロ−6−ニトロ−1,3−ベンゾチアゾール−2−イル)ジアゼニル]−フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[1H−[1,3]チアゾロ[5,4−f]インダゾール−6−イルジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(5−クロロ[1,3]チアゾロ[5,4−b]ピリジン−2−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(5−メトキシ[1,3]チアゾロ[5,4−b]ピリジン−2−イル)ジアゼニル]−フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、N,N−ジエチル−2−(エチル{4−[1,3−チアゾール−2−イルジアゼニル]フェニル}アミノ)−N−メチルエタナミニウムブロミド、N−[2−(エチル{4−[1,3−チアゾール−2−イルジアゼニル]フェニル}アミノ)エチル]−N,N−ジメチルベンゼナミニウムブロミド、2−(エチル{4−[1,2,4−チアジアゾール−5−イルジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[(3−フェニル−1,2,4−チアジアゾール−5−イル)ジアゼニル]フェニル}アミノ)−N,N,N−トリメチルエタナミニウムブロミド、2−[{4−[(3−クロロ−1,2,4−チアジアゾール−5−イル)ジアゼニル]フェニル}(エチル)アミノ]−N,N,N−トリメチルエタナミニウムブロミド、2−(エチル{4−[1H−1,2,4−トリアゾール−5−イルジアゼニル]フェニル}−アミノ)−N,N,N−トリメチルエタナミニウムブロミド、1−[2−(エチル{4−[(1−メチル−1H−イミダゾール−2−イル)ジアゼニル]−フェニル}アミノ)エチル]−N,N,N−トリメチルエタナミニウムブロミド、1−[2−(エチル{3−メチル−4−[(1−メチル−1H−イミダゾール−2−イル)ジアゼニル]フェニル}アミノ)エチル]−N,N,N−トリメチルエタナミニウムブロミド、及び1−{2−[{3−クロロ−4−[(1−メチル−1H−イミダゾール−2−イル)ジアゼニル]フェニル}(エチル)アミノ]エチル}−N,N,N−トリメチルエタナミニウムブロミドからなる群から選択される少なくとも1つのカチオン性アゾ染料とを含む、ケラチン繊維の明色化及び染色を同時に行うための薬剤の使用。
- 前記酸化剤は、過酸化水素、又は過酸化水素を、尿素、メラミン、ホウ酸ナトリウム、若しくは炭酸ナトリウム上に付加した化合物、及び過硫酸塩、から選択されることを特徴とする、請求項1に記載の使用。
- 前記カチオン性アゾ染料は、0.01重量%〜10重量%の量で存在することを特徴とする、請求項1又は2に記載の使用。
- ニトロ染料類、アゾ染料類、アントラキノン染料類、トリフェニルメタン染料類、及び塩基性染料類又は酸性染料類、から成る群由来の少なくとも1種の更なる直接染料を追加的に含むことを特徴とする、請求項1〜3のいずれか一項に記載の使用。
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EP06003343.8 | 2006-02-18 | ||
EP06003343A EP1820536B1 (en) | 2006-02-18 | 2006-02-18 | Coloring agents for keratin fibers |
PCT/IB2007/050428 WO2007093943A1 (en) | 2006-02-18 | 2007-02-09 | Coloring agents for keratin fibers |
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EP (1) | EP1820536B1 (ja) |
JP (1) | JP5431735B2 (ja) |
CN (1) | CN101384303B (ja) |
AT (1) | ATE536915T1 (ja) |
MX (1) | MX2008010403A (ja) |
WO (1) | WO2007093943A1 (ja) |
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EP1820536B1 (en) * | 2006-02-18 | 2011-12-14 | Wella GmbH | Coloring agents for keratin fibers |
US8609074B2 (en) * | 2011-12-30 | 2013-12-17 | L'oreal | Methods for making up a keratinous substrate |
WO2016149432A1 (en) | 2015-03-19 | 2016-09-22 | The Procter & Gamble Company | Method of coloring hair with direct dye compounds |
WO2016149491A1 (en) | 2015-03-19 | 2016-09-22 | The Procter & Gamble Company | Fluorescent compounds for treating hair |
EP3271025A1 (en) | 2015-03-19 | 2018-01-24 | Noxell Corporation | Method of coloring hair with direct dye compounds |
EP3270874A1 (en) | 2015-03-19 | 2018-01-24 | Noxell Corporation | Compositions for dyeing hair with cationic direct dyes |
US9913791B2 (en) | 2015-03-19 | 2018-03-13 | Noxell Corporation | Method for improving acid perspiration resistance of fluorescent compounds on hair |
US9943472B2 (en) | 2015-03-19 | 2018-04-17 | Noxell Corporation | Acid perspiration resistant fluorescent compounds for treating hair |
EP3271423B1 (en) * | 2015-03-19 | 2022-08-31 | Basf Se | Cationic direct dyes |
MX366544B (es) | 2015-03-19 | 2019-07-12 | Noxell Corp | Composiciones para teñir el cabello con colorantes directos cationicos. |
US9872823B2 (en) | 2015-03-19 | 2018-01-23 | Noxell Corporation | Method for improving fastness properties of fluorescent compounds on hair |
US9982138B2 (en) | 2016-09-13 | 2018-05-29 | Noxell Corporation | Hair color compositions comprising stable violet-blue to blue imidazolium dyes |
US10034823B2 (en) | 2016-09-16 | 2018-07-31 | Noxell Corporation | Method of coloring hair with washfast blue imidazolium direct dye compounds |
US9918919B1 (en) | 2016-09-16 | 2018-03-20 | Noxell Corporation | Method of coloring hair with washfast yellow imidazolium direct dye compounds |
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GB1162665A (en) * | 1966-09-27 | 1969-08-27 | Du Pont | Cationic and Basic Benzothiazolylazo Dyes, their preparation and use |
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DE3101140A1 (de) * | 1981-01-16 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von loesungen kationischer azofarbstoffe |
EP0514336B1 (de) * | 1991-05-17 | 1996-12-11 | Ciba-Geigy Ag | Verfahren zur Herstellung hochkonzentrierter wässriger Lösungen von kationischen Azofarbstoffen |
DE4322211A1 (de) | 1993-07-03 | 1995-01-12 | Basf Ag | Wäßrige, mehrphasige, stabile Fertigformulierung für Pflanzenschutz-Wirkstoffe und Verfahren zu ihrer Herstellung |
FR2741798B1 (fr) | 1995-12-01 | 1998-01-09 | Oreal | Composition de teinture eclaircissante pour fibres keratiniques comprenant un colorant direct specifique |
DE19618595A1 (de) | 1996-05-09 | 1997-11-13 | Wella Ag | Färbemittel |
DE19835575A1 (de) * | 1998-08-06 | 2000-03-02 | Mannesmann Sachs Ag | Parallelhybridantrieb für ein Kraftfahrzeug mit in die elektrische Maschine integrierter Kupplung und zugehörige Elektromotorbaueinheit |
DE10118271A1 (de) | 2001-04-12 | 2002-03-14 | Henkel Kgaa | Diazothiazol-Farbstoffe |
CN1197916C (zh) | 2002-03-20 | 2005-04-20 | 上海市染料研究所 | 一种橄榄绿色阳离子染料及其制备方法 |
FR2838338B1 (fr) * | 2002-04-11 | 2004-05-28 | Oreal | Kit pour la teinture des fibres keratiniques |
EP1820536B1 (en) * | 2006-02-18 | 2011-12-14 | Wella GmbH | Coloring agents for keratin fibers |
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2006
- 2006-02-18 EP EP06003343A patent/EP1820536B1/en not_active Not-in-force
- 2006-02-18 AT AT06003343T patent/ATE536915T1/de active
-
2007
- 2007-02-09 WO PCT/IB2007/050428 patent/WO2007093943A1/en active Application Filing
- 2007-02-09 MX MX2008010403A patent/MX2008010403A/es active IP Right Grant
- 2007-02-09 JP JP2008551946A patent/JP5431735B2/ja not_active Expired - Fee Related
- 2007-02-09 CN CN200780005873XA patent/CN101384303B/zh not_active Expired - Fee Related
- 2007-02-16 US US11/707,371 patent/US7513917B2/en active Active
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2009
- 2009-02-26 US US12/393,539 patent/US7658771B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN101384303B (zh) | 2012-07-04 |
CN101384303A (zh) | 2009-03-11 |
EP1820536A1 (en) | 2007-08-22 |
US20090158532A1 (en) | 2009-06-25 |
EP1820536B1 (en) | 2011-12-14 |
ATE536915T1 (de) | 2011-12-15 |
US20070199161A1 (en) | 2007-08-30 |
JP2009531279A (ja) | 2009-09-03 |
MX2008010403A (es) | 2008-09-23 |
WO2007093943A1 (en) | 2007-08-23 |
US7513917B2 (en) | 2009-04-07 |
US7658771B2 (en) | 2010-02-09 |
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