JP2018505255A - ケラチン繊維を染色するための、ピラゾロピリジン単位を担持するアゾメチンタイプの化合物の使用 - Google Patents
ケラチン繊維を染色するための、ピラゾロピリジン単位を担持するアゾメチンタイプの化合物の使用 Download PDFInfo
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- JP2018505255A JP2018505255A JP2017532887A JP2017532887A JP2018505255A JP 2018505255 A JP2018505255 A JP 2018505255A JP 2017532887 A JP2017532887 A JP 2017532887A JP 2017532887 A JP2017532887 A JP 2017532887A JP 2018505255 A JP2018505255 A JP 2018505255A
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- Prior art keywords
- radical
- alkyl
- optionally
- hydrogen atom
- substituted
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- 150000001875 compounds Chemical group 0.000 title claims abstract description 99
- 239000000835 fiber Substances 0.000 title claims abstract description 30
- 102000011782 Keratins Human genes 0.000 title claims abstract description 29
- 108010076876 Keratins Proteins 0.000 title claims abstract description 29
- 238000004043 dyeing Methods 0.000 title claims abstract description 24
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical group C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000000975 dye Substances 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000012453 solvate Substances 0.000 claims abstract description 11
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- -1 hydroxyl radicals Chemical group 0.000 claims description 134
- 150000003254 radicals Chemical group 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000007792 addition Methods 0.000 claims description 22
- 239000007800 oxidant agent Substances 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000002091 cationic group Chemical group 0.000 claims description 13
- 230000001590 oxidative effect Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000005936 piperidyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002610 basifying agent Substances 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000010561 standard procedure Methods 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 238000006722 reduction reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 229910001748 carbonate mineral Inorganic materials 0.000 claims description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- CQWXKASOCUAEOW-UHFFFAOYSA-N 2-[2-(carboxymethoxy)ethoxy]acetic acid Chemical class OC(=O)COCCOCC(O)=O CQWXKASOCUAEOW-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 abstract 1
- 238000003419 tautomerization reaction Methods 0.000 abstract 1
- 239000000982 direct dye Substances 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 4
- 235000019233 fast yellow AB Nutrition 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005638 hydrazono group Chemical group 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 description 2
- GFAZBXKENDSJEB-UHFFFAOYSA-N 2,5-dihydroxy-3-methoxy-6-methylcyclohexa-2,5-diene-1,4-dione Chemical compound COC1=C(O)C(=O)C(C)=C(O)C1=O GFAZBXKENDSJEB-UHFFFAOYSA-N 0.000 description 2
- KEEQZNSCYCPKOJ-UHFFFAOYSA-N 2,6-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=CC(CC)=C1N KEEQZNSCYCPKOJ-UHFFFAOYSA-N 0.000 description 2
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 2
- KULOFVMDAJSPOK-UHFFFAOYSA-N 2-(2,5-diaminophenoxy)ethanol Chemical compound NC1=CC=C(N)C(OCCO)=C1 KULOFVMDAJSPOK-UHFFFAOYSA-N 0.000 description 2
- HFFCVKYVJNYQLA-UHFFFAOYSA-N 2-(3-aminopyrazolo[1,5-a]pyridin-2-yl)oxyethanol;hydrochloride Chemical compound Cl.C1=CC=CC2=C(N)C(OCCO)=NN21 HFFCVKYVJNYQLA-UHFFFAOYSA-N 0.000 description 2
- AVKBLCWBDLLVRL-UHFFFAOYSA-N 2-(methoxymethyl)benzene-1,4-diamine Chemical compound COCC1=CC(N)=CC=C1N AVKBLCWBDLLVRL-UHFFFAOYSA-N 0.000 description 2
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 description 2
- RSRYAYQRBHJYCG-UHFFFAOYSA-N 2-anilinocyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(NC=2C=CC=CC=2)=C1 RSRYAYQRBHJYCG-UHFFFAOYSA-N 0.000 description 2
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 2
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- WNYJRJRHKRZXEO-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)C1=CC(N)=CC=C1N WNYJRJRHKRZXEO-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- ONLSZHNKCZRPCP-UHFFFAOYSA-M 4-n-[3-(3-methylimidazol-3-ium-1-yl)propyl]benzene-1,4-diamine;chloride Chemical compound [Cl-].C1=[N+](C)C=CN1CCCNC1=CC=C(N)C=C1 ONLSZHNKCZRPCP-UHFFFAOYSA-M 0.000 description 2
- XURABDHWIADCPO-UHFFFAOYSA-N 4-prop-2-enylhepta-1,6-diene Chemical compound C=CCC(CC=C)CC=C XURABDHWIADCPO-UHFFFAOYSA-N 0.000 description 2
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- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- FTUYQIPAPWPHNC-UHFFFAOYSA-M sodium;4-[[4-[benzyl(ethyl)amino]phenyl]-[4-[benzyl(ethyl)azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=CC=CC=2)C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC=C1 FTUYQIPAPWPHNC-UHFFFAOYSA-M 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- PVEFEIWVJKUCLJ-UHFFFAOYSA-N sulfuric acid;toluene Chemical compound OS(O)(=O)=O.CC1=CC=CC=C1 PVEFEIWVJKUCLJ-UHFFFAOYSA-N 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000002888 zwitterionic surfactant 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/22—Peroxides; Oxygen; Ozone
-
- 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
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Abstract
Description
式(I)及び(II)中:
・Z1は、酸素原子又は基−N(R6)−を示し;
Z1が、−N(R6)−を示すとき、R1及びR6は、それらが結合する窒素原子と一緒に、任意選択で置換された、任意選択でカチオン性の、5〜8員の、飽和、不飽和若しくは芳香族ヘテロ環を形成することができ;
・R1及びR6は、各々独立に、以下:
− 水素原子;
− 任意選択で1個又は複数個の非隣接ヘテロ原子、好ましくは酸素で分断され、且つ/又は好ましくはi)ヒドロキシル、ii)任意選択で置換された、5〜8員の、飽和、不飽和若しくは芳香族(ヘテロ)環、iii)−N(R’)R’’、iv)−N+R’R’’R’’’(R’、R’’及びR’’’は各々独立に、C1〜C6アルキル基を示す)から選択される1つ又は複数の基で、任意選択で置換されたC1〜C10アルキルラジカル;
− 任意選択で置換された、飽和、不飽和若しくは芳香族5〜8員(ヘテロ)環基
を示し;
特に、R1は、(ポリ)ヒドロキシ(C1〜C6アルキル)、好ましくはヒドロキシ(C1〜C6アルキル)基を示し、またZ1は、酸素原子を示し;
・R2、R3、R4及びR5は、各々独立に、以下:
− 水素原子;
− 任意選択で置換されたC1〜C4アルキルラジカル、
− −NH2、−N(H)−R10、−N(R11)−R12、OH及び−OR9から選択される基(ここで、R9及びR10は、任意選択で置換された、直鎖若しくは分岐状C1〜C6アルキルを示し、R11及びR12は、同じでも異なっていてもよく、任意選択で置換された、直鎖若しくは分岐状C1〜C6アルキルを示し、ここで、R11及びR12は、それらが結合する窒素原子と一緒に、任意選択で酸素及び窒素から選択される1個又は複数個の他のヘテロ原子若しくは基を含む、飽和、不飽和若しくは芳香族5〜8員ヘテロ環を形成することが可能であり、このヘテロ環は、任意選択で置換されている)
を示し;
・R2、R3、R4及びR5は、隣接するラジカルとペアで、任意選択で置換された、飽和若しくは不飽和又は芳香族(ヘテロ)環を形成することができ;
・R’2及びR’3は、同じでも異なっていてもよく、以下:
− 水素原子;
− 任意選択で1つ又は複数のヒドロキシルラジカルで置換された、C1〜C6、好ましくはC1〜C4アルキルラジカル;
− C1〜C6アルキルカルボキシレートラジカル;
− カルボキシルラジカル
を示し;
・R’は、以下:
− 水素原子;
− C1〜C6アルキルラジカル
を示し;
・R’6は、以下:
− 水素原子;
− ハロゲン原子;
− 任意選択で、1個又は複数個の非隣接酸素原子及び/又は1つ又は複数の非隣接二価基−N(R’9)−で分断され、且つ任意選択で、−OH及び−N(R’7)R’8から選択される、同じでも異なっていてもよい1つ又は複数のラジカルで置換された直鎖又は分岐状C1〜C10アルキルラジカル;
− カルボキシルラジカル;
− C1〜C10アルキルカルボキシレート;
− ラジカル−CONR’ 7R’8;
− C1〜C10アルコキシラジカル又はC1〜C10(ポリ)ヒドロキシアルコキシラジカル;
− (ポリ)(C1〜C10アルコキシ)−(C1〜C10アルコキシ)ラジカル;
− ラジカル−O−Ak−N(R’9)R’10(ここで、Akは、任意選択で、1個又は複数個の酸素原子及び/又は非隣接二価基−N(R’7)−で分断された、直鎖C1〜C8又は分岐状C3〜C8二価アルキレンラジカルである)
を示し;
・R’7及びR’8は、同じでも異なっていてもよく、以下:
− 水素原子;
− 任意選択で1つ又は複数のヒドロキシルラジカルで置換された、C1〜C8アルキルラジカル;
を示し;
・R’9及びR’10は、同じでも異なっていてもよく、i)直鎖若しくは分岐状C1〜C6アルキルラジカル、ii)C2〜C6アルケニルラジカル又はiii)C2〜C6アルキニルラジカルを示し;
・R’9及びR’10は、それらを質量担持する窒素と一緒に、飽和若しくは不飽和5〜8員ヘテロ環を形成することができ、この鎖員の1つは、場合により、酸素原子若しくは窒素原子、又は二価ラジカル−N(R’11)−であり、ここで、R’11は、水素原子、又は任意選択で、−OH、−N(R’7)R’8及びC1〜C4アルキルから選択される1つ又は複数のラジカルで置換された、C1〜C4アルキル基を示し;
・R’’は、以下:
− 水素原子;
− 任意選択で酸素原子又は二価基−N(R)−(Rは、水素原子又はC1〜C4アルキル基を示す)で分断された、直鎖若しくは分岐状C1〜C10アルキルラジカル
を示し;
ここで、式(I)又は(II)の化合物は、陽荷電されている場合、分子の電気的中性を達成するために、カチオン電荷と同数のアニオン対イオンを含むことが理解される。
・R’7及びR’8は、独立に、水素原子、又は任意選択でヒドロキシルラジカルで置換されたC1〜C4アルキルラジカルを示し、
・R’9及びR’10は、独立に、直鎖又は分岐状C1〜C4アルキルラジカルを示し;あるいは、
・R’9及びR’10は、それらを担持する窒素原子と一緒に、飽和若しくは不飽和5〜8員ヘテロ環を形成し、この鎖員の1つは、場合により、酸素若しくは窒素原子、又はラジカルNR’11であり、ここで、R’11は、水素原子、又は任意選択で−OH、−NR’7R’8及びC1〜C4アルキルから選択される1つ又は複数のラジカルで置換された、C1〜C4アルキル基を示す)
を示すような化合物である。
・R’9及びR’10は、独立に、飽和の、直鎖若しくは分岐状C1〜C4アルキルラジカルを示すか;あるいは、
・R’9及びR’10は、それらを担持する窒素原子と一緒に、ピロリジニル、モルホリニル、イミダゾリル、ピペラジニル及びピペリジルから選択されるヘテロ環を形成し、前記ヘテロ環は、任意選択で、−OH及びメチルなどのC1〜C4アルキルから選択される1つ又は複数のラジカルで置換されている;好ましくは、前記ヘテロ環は、任意選択で、メチルなどのC1〜C4アルキル基で置換されている)
を示すような化合物である。
を示すような化合物である。
式(I)及び(II)中:
Z1=Oであるとき、R1=−CH2CH2OH、−CH2CH2N(CH3)2、−CH2CH2CH2N(CH3)2であり、
Z1=−N(R6)−で、且つR6が、水素原子を示すとき、R1=−CH2CH2N(CH3)2、−CH2CH2CH2N(CH3)2であり、
R’、R2、R3、R4及びR5は、水素原子を示し、
R’2、R’3及びR’’は、同じでも異なっていてもよく、水素原子又はメチルラジカルを示し、
R’6は、水素原子若しくはメチル、エチル、−O−(CH2)2−OH、−O−(CH2)3−OH、−O−(CH2)2−Het又は−O−(CH2)3−Hetラジカルを示し、ここで、Hetは、ピロリジニル若しくはモルホリノ若しくはイミダゾリル又はN−メチルピペラジノ若しくはピペリジノ基を表す。
− 第1段階で、3位にアミノ基を含むピラゾロ[1,5−a]ピリジン化合物A1を、5位がフリーで、4位にアミノ基を含むインドール化合物A2と反応させるが、
好ましくは、この反応は、i)水又は水/C1〜C10アルコール(例えば、エタノール)の混合物などの極性プロトン性溶媒中、ii)且つ/又は、特に水酸化ナトリウム、水酸化カリウム、炭酸カリウムなどの炭酸塩鉱物、若しくは酢酸塩から選択される、下に定義する通りの1種又は複数種の塩基化剤の存在下で、iii)且つ/又は、過酸化物若しくは過硫酸塩などの化学酸化剤の存在下で、iv)且つ/又は、室温、すなわち25℃から溶媒の還流温度までの温度、好ましくは室温で実施し;次に、
− 第2段階で、反応媒体を5分〜48時間、より具体的には、反応を室温で実施する場合、30分〜24時間の時間にわたり攪拌下に維持し;続いて、
− 反応生成物(I)を任意選択で再結晶化、濾過又はクロマトグラフィーなどの標準的技術により精製するものであり;
− 一変形によれば、一旦精製した化合物(I)を、グラファイト上に担持された水素による接触還元などの還元剤を用いて、又はパラジウム若しくはニッケルなどの遷移金属を用いて、あるいは、水素化物若しくはホウ化水素、又はトリグリコール酸誘導体での還元により還元して、ロイコ化合物(II)を取得し;これに続き、任意選択で、前述した標準的技術による精製のステップを実施して、ロイコ化合物(II)を取得するものであり;
− 別の変形によれば、化合物(I)を精製せずに、前述した還元剤を用いて還元して、ロイコ化合物(II)を取得し、これに続き任意選択で、前述した標準的技術による精製のステップを実施する。
・RBは、C1〜C4アルキルラジカル又はβ−ヒドロキシエチル、β−ヒドロキシプロピル若しくはγ−ヒドロキシプロピルラジカルを示し;
・RA及びRCは、同じでも異なっていてもよく、β−ヒドロキシエチル、β−ヒドロキシプロピル、γ−ヒドロキシプロピル又はβ,γ−ジヒドロキシプロピルラジカルを示し、ここで、ラジカルRB、RC若しくはRAの少なくとも1つは、γ−ヒドロキシプロピルラジカルを示し、RB及びRCは、RBが、仏国特許第2 692 572号明細書に記載されているものなどのγ−ヒドロキシプロピルラジカルであるとき、同時にβ−ヒドロキシエチルラジカルを示すことはできない)。
がある。
下記の染料組成物を、下の表に表示する成分を用いて調製し、また、具体的に、上の実施例1及び2で合成した染料を示す。
96°エチルアルコール 20.8g
40質量%の水溶液としてのジエチレントリアミン五酢酸の五ナトリウム 0.48gAM*
60質量%の水溶液としての(C8〜C10アルキル)ポリグリコシド 3.6gAM*
ベンジルアルコール 2.0g
8エチレンオキシド単位を含むポリエチレングリコール 3.0g
Na2HPO4 0.28g
KH2PO4 0.46g
*AM:活性物質
下記の染料組成物を以下の調製した。
96°エチルアルコール 20.8g
40%水溶液としてのジエチレントリアミン五酢酸の五ナトリウム塩 0.48g AM*
60質量%水溶液としてのC8〜C10アルキルポリグリコシド 3.6g AM*
ベンジルアルコール 2.0g
8単位のエチレンオキシドを含むポリエチレングリコール 3.0g
NH4Cl 4.32g
20%NH3を含むアンモニア水 2.94g
*AM:活性物質
Claims (15)
- 下記式(I)のピラゾロピリジン単位を担持するアゾメチンタイプの染料及び下記式(II)のそれらのロイコ形態、さらにはそれらの光学及び幾何異性体、それらの互変異性体、それらの酸又は塩基付加塩、並びに水和物などのそれらの溶媒和物:
(式(I)及び(II)中:
・Z1は、酸素原子又は基−N(R6)−を示し;
Z1が、−N(R6)−を示すとき、R1及びR6は、それらが結合する窒素原子と一緒に、任意選択で置換された、5〜8員の、飽和、不飽和若しくは芳香族ヘテロ環を形成することができ;
・R1及びR6は、各々独立に、以下:
− 水素原子;
− 任意選択で1個又は複数個の非隣接ヘテロ原子、好ましくは酸素で分断され、且つ/又は好ましくはi)ヒドロキシル、ii)任意選択で置換された、5〜8員の、飽和、不飽和若しくは芳香族(ヘテロ)環、iii)−N(R’)R’’、iv)−N+R’R’’R’’’(R’、R’’及びR’’’は各々独立に、C1〜C6アルキル基を示す)から選択される1つ又は複数の基で、任意選択で置換されたC1〜C10アルキルラジカル;
− 任意選択で置換された、飽和、不飽和若しくは芳香族5〜8員(ヘテロ)環基
を示し;
・R2、R3、R4及びR5は、各々独立に、以下:
− 水素原子、
− 任意選択で置換されたC1〜C4アルキルラジカル、
− −NH2、−N(H)−R10、−N(R11)−R12、OH及び−OR9から選択される基(ここで、R9及びR10は、任意選択で置換された、直鎖若しくは分岐状C1〜C6アルキルを示し、R11及びR12は、同じでも異なっていてもよく、任意選択で置換された、直鎖若しくは分岐状C1〜C6アルキルを示し、ここで、R11及びR12は、それらが結合する窒素原子と一緒に、任意選択で酸素及び窒素から選択される1個又は複数個の他のヘテロ原子若しくは基を含む、飽和、不飽和若しくは芳香族5〜8員ヘテロ環を形成することが可能であり、前記ヘテロ環は、任意選択で置換されている)
を示し;
・R2、R3、R4及びR5は、隣接するラジカルとペアで、任意選択で置換された、飽和若しくは不飽和又は芳香族(ヘテロ)環を形成することができ;
・R’2及びR’3は、同じでも異なっていてもよく、以下:
− 水素原子;
− 任意選択で1つ又は複数のヒドロキシルラジカルで置換された、C1〜C6、好ましくはC1〜C4アルキルラジカル;
− C1〜C6アルキルカルボキシレートラジカル;
− カルボキシルラジカル
を示し;
・R’は、以下:
− 水素原子;
− C1〜C6アルキルラジカル
を示し;
・R’6は、以下:
− 水素原子;
− ハロゲン原子;
− 任意選択で、1個又は複数個の非隣接酸素原子及び/又は1つ又は複数の非隣接二価基−N(R’9)−で分断され、且つ任意選択で、−OH及び−N(R’7)R’8から選択される、同じでも異なっていてもよい1つ又は複数のラジカルで置換された直鎖又は分岐状C1〜C10アルキルラジカル;
− カルボキシルラジカル;
− C1〜C10アルキルカルボキシレート;
− ラジカル−CONR’ 7R’8;
− C1〜C10アルコキシラジカル又はC1〜C10(ポリ)ヒドロキシアルコキシラジカル;
− (ポリ)(C1〜C10アルコキシ)−(C1〜C10アルコキシ)ラジカル;
− ラジカル−O−Ak−N(R’9)R’10(ここで、Akは、任意選択で、1個又は複数個の酸素原子及び/又は非隣接二価基−N(R’7)−で分断された、直鎖C1〜C8又は分岐状C3〜C8二価アルキレンラジカルである)
を示し;
・R’7及びR’8は、同じでも異なっていてもよく、以下:
− 水素原子;
− 任意選択で1つ又は複数のヒドロキシルラジカルで置換された、C1〜C8アルキルラジカル;
を示し;
・R’9及びR’10は、同じでも異なっていてもよく、i)直鎖若しくは分岐状C1〜C6アルキルラジカル、ii)C2〜C6アルケニルラジカル又はiii)C2〜C6アルキニルラジカルを示し;
・R’9及びR’10は、それらを担持する窒素と一緒に、飽和若しくは不飽和5〜8員ヘテロ環を形成することができ、この鎖員の1つは、場合により、酸素原子若しくは窒素原子、又は二価ラジカル−N(R’11)−であり、ここで、R’11は、水素原子、又は任意選択で、−OH、−N(R’7)R’8及びC1〜C4アルキルから選択される1つ又は複数のラジカルで置換された、C1〜C4アルキル基を示し;
・R’’は、以下:
− 水素原子;
− 任意選択で酸素原子又は二価基−N(R)−(Rは、水素原子又はC1〜C4アルキル基を示す)で分断された、直鎖若しくは分岐状C1〜C10アルキルラジカル
を示し;
ここで、式(I)又は(II)の化合物は、陽荷電されている場合、分子の電気的中性を達成するために、カチオン電荷と同数のアニオン対イオンを含むことが理解される)。 - Z1が、酸素原子又はラジカル−N(H)−を示すことを特徴とする、請求項1に記載の化合物。
- R1が、C1〜C6アルキルラジカル、ヒドロキシル基で置換されたC1〜C6アルキルラジカル、ジメチルアミノなどの(ジ)(C1〜C4)アルキルアミノで置換されたC1〜C6アルキルラジカル、イミダゾリル、ピロリジニル、ピペリジル、モルホリニル及びピペラジニルから選択される含窒素ヘテロ環で置換されたC1〜C6アルキルラジカルを示すことを特徴とする、請求項1又は2に記載の化合物。
- R2、R3、R4及びR5が、独立に、水素原子又はC1〜C4アルキルラジカルを示すことを特徴とする、請求項1〜3のいずれか1項に記載の化合物。
- R’2及びR’3が、独立に、水素原子、又は任意選択で1つ又は複数のヒドロキシルラジカルで置換された、C1〜C4アルキルラジカルを示すことを特徴とする、請求項1〜4のいずれか1項に記載の化合物。
- R’が、水素原子又はC1〜C4アルキルラジカルを示すことを特徴とする、請求項1〜5のいずれか1項に記載の化合物。
- R’6が、以下:i)水素原子;ii)任意選択でヒドロキシルラジカルで置換された、直鎖若しくは分岐状C1〜C6アルキルラジカル;iii)C1〜C6ヒドロキシアルコキシラジカル;iv)ラジカル−O−Ak−NR’9R’10(ここで、Akは、直鎖二価C1〜C8アルキレンラジカルを示し、
・R’9及びR’10は、独立に、飽和の、直鎖若しくは分岐状C1〜C4アルキルラジカルを示すか;あるいは、
・R’9及びR’10は、それらを担持する窒素原子と一緒に、ピロリジニル、モルホリニル、イミダゾリル、ピペラジニル及びピペリジルから選択されるヘテロ環を形成し、前記ヘテロ環は、任意選択で、−OH及びC1〜C4アルキルから選択される1つ又は複数のラジカルで置換されている)
を示すことを特徴とする、請求項1〜6のいずれか1項に記載の化合物。 - R’’が、以下:水素原子又は直鎖C1〜C6アルキルラジカルを示すことを特徴とする、請求項1〜7のいずれか1項に記載の化合物。
- 式(I)及び(II)の化合物、さらにはそれらの光学異性体、幾何異性体及び互変異性体、それらの酸又は塩基付加塩、並びに水和物などの溶媒和物:
Z1=Oの場合、R1=−CH2CH2OH、−CH2CH2N(CH3)2、−CH2CH2CH2N(CH3)2であり、
Z1=−N(R6)−で、且つR6が、水素原子を示す場合、R1=−CH2CH2N(CH3)2、−CH2CH2CH2N(CH3)2であり、
R’、R2、R3、R4及びR5は、水素原子を示し、
R’2、R’3及びR’’は、同じでも異なっていてもよく、水素原子又はメチルラジカルを示し、
R’6は、水素原子若しくはメチル、エチル、−O−(CH2)2−OH、−O−(CH2)3−OH、−O−(CH2)2−Het又は−O−(CH2)3−Hetラジカルを示し、ここで、Hetは、ピロリジニル若しくはモルホリノ若しくはイミダゾリル又はN−メチルピペラジノ若しくはピペリジノ基を表す)
から選択されることを特徴とする、請求項1〜8のいずれか1項に記載の化合物。 - 染色に適した媒体中に、請求項1〜9のいずれか1項に記載の1つ又は複数の化合物を含む、ケラチン繊維を染色するための組成物。
- 請求項1〜9のいずれか1項に記載の化合物が、前記組成物の総質量に対して、0.01質量%〜15質量%、好ましくは0.05質量%〜10質量%の範囲の量で存在することを特徴とする、請求項10に記載の組成物。
- 1種又は複数種の酸化剤をさらに含むことを特徴とする、請求項10又は11に記載の組成物。
- ケラチン繊維を染色するための、請求項1〜9のいずれか1項に記載の1つ又は複数の化合物の使用。
- ケラチン繊維を染色するための方法であって、請求項10〜12のいずれか1項に記載の少なくとも1つの染料組成物をこれらの繊維に適用することを特徴とする方法。
- 下記のスキーム:
− 第1段階で、3位にアミノ基を含むピラゾロ[1,5−a]ピリジン化合物A1を、5位がフリーで、4位にアミノ基を含むインドール化合物A2と反応させるが、
好ましくは、この反応は、i)水又は水/C1〜C10アルコール(例えば、エタノール)の混合物などの極性プロトン性溶媒中、ii)且つ/又は、特に水酸化ナトリウム、水酸化カリウム、炭酸カリウムなどの炭酸塩鉱物、若しくは酢酸塩から選択される、以下に定義する通りの1種又は複数種の塩基化剤の存在下で、iii)且つ/又は、過酸化物若しくは過硫酸塩などの化学酸化剤の存在下で、iv)且つ/又は、室温、すなわち25℃から溶媒の還流温度までの温度、好ましくは室温で行い;次に、
− 第2段階で、前記反応媒体を5分〜48時間、より具体的には、前記反応を室温で行う場合、30分〜24時間の時間にわたり攪拌下に維持し;続いて、
− 前記反応生成物(I)を任意選択で再結晶化、濾過又はクロマトグラフィーなどの標準的技術により精製するものであり;
− 一変形によれば、一旦精製した化合物(I)を、グラファイト上に担持された水素による接触還元などの還元剤を用いて、又はパラジウム若しくはニッケルなどの遷移金属を用いて、あるいは、水素化物若しくはホウ化水素、又はトリグリコール酸誘導体での還元により還元して、ロイコ化合物(II)を取得し;これに続き、任意選択で、前述した標準的技術による精製のステップを行って、前記ロイコ化合物(II)を取得するものであり;
− 別の変形によれば、化合物(I)を精製せずに、前述した還元剤を用いて還元して、前記ロイコ化合物(II)を取得し、これに続き任意選択で、前述した標準的技術による精製のステップを行って、前記ロイコ化合物(II)を取得する、方法。
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FR1463004A FR3030246B1 (fr) | 2014-12-19 | 2014-12-19 | Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a motif pyrazolopyridine |
PCT/EP2015/080321 WO2016097196A1 (en) | 2014-12-19 | 2015-12-17 | Use for dyeing keratin fibres of a compound of azomethine type bearing a pyrazolopyridine unit |
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JP2010260860A (ja) * | 2009-04-30 | 2010-11-18 | L'oreal Sa | ケラチン繊維の染色のためのカチオン性ピラゾロピリジン単位を含むアゾメチンタイプの化合物 |
FR2999422A1 (fr) * | 2012-12-19 | 2014-06-20 | Oreal | Procede de coloration des fibres keratiniques comprenant l'application d'une base d'oxydation aminopyrazolopyridine en l'absence de coupleur |
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US10245223B2 (en) | 2019-04-02 |
US20170348215A1 (en) | 2017-12-07 |
EP3233854B1 (en) | 2018-11-21 |
JP6427678B2 (ja) | 2018-11-21 |
ES2704910T3 (es) | 2019-03-20 |
CN107223124A (zh) | 2017-09-29 |
FR3030246A1 (fr) | 2016-06-24 |
CN107223124B (zh) | 2019-10-25 |
FR3030246B1 (fr) | 2017-02-10 |
WO2016097196A1 (en) | 2016-06-23 |
EP3233854A1 (en) | 2017-10-25 |
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