JP5866293B2 - 新規カチオン性アミノピリジン、カチオン性アミノピリジンを含む染料組成物、そのための方法およびその使用 - Google Patents
新規カチオン性アミノピリジン、カチオン性アミノピリジンを含む染料組成物、そのための方法およびその使用 Download PDFInfo
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- JP5866293B2 JP5866293B2 JP2012542464A JP2012542464A JP5866293B2 JP 5866293 B2 JP5866293 B2 JP 5866293B2 JP 2012542464 A JP2012542464 A JP 2012542464A JP 2012542464 A JP2012542464 A JP 2012542464A JP 5866293 B2 JP5866293 B2 JP 5866293B2
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- JP
- Japan
- Prior art keywords
- amino
- diaminopyridin
- radical
- cationic
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 cationic aminopyridines Chemical class 0.000 title claims description 195
- 239000000203 mixture Substances 0.000 title claims description 77
- 238000000034 method Methods 0.000 title claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000003254 radicals Chemical group 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000003282 alkyl amino group Chemical group 0.000 claims description 30
- 125000002091 cationic group Chemical group 0.000 claims description 30
- 239000000835 fiber Substances 0.000 claims description 28
- 102000011782 Keratins Human genes 0.000 claims description 26
- 108010076876 Keratins Proteins 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 238000004043 dyeing Methods 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 20
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 230000001590 oxidative effect Effects 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 239000007800 oxidant agent Substances 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 6
- BVIXDZIQDYXWQL-UHFFFAOYSA-N azane;morpholine Chemical compound N.C1COCCN1 BVIXDZIQDYXWQL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 5
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 108090000854 Oxidoreductases Proteins 0.000 claims description 4
- 102000004316 Oxidoreductases Human genes 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims description 3
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 3
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052701 rubidium Chemical group 0.000 claims description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 3
- CKQFWQCSMNUSRI-UHFFFAOYSA-N 1,1-dimethylpiperazin-1-ium Chemical compound C[N+]1(C)CCNCC1 CKQFWQCSMNUSRI-UHFFFAOYSA-N 0.000 claims description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 claims description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- AMSDWLOANMAILF-UHFFFAOYSA-O 2-(1h-imidazol-3-ium-3-yl)ethanol Chemical compound OCC[NH+]1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-O 0.000 claims description 2
- RDZSWWBOGABEFN-UHFFFAOYSA-N 2-(4,4-dimethylpiperazin-4-ium-1-yl)pyridine-3,5-diamine Chemical compound C1C[N+](C)(C)CCN1C1=NC=C(N)C=C1N RDZSWWBOGABEFN-UHFFFAOYSA-N 0.000 claims description 2
- TYQCGGYLZFNIGH-UHFFFAOYSA-N 2-[4-(3,5-diaminopyridin-2-yl)-1-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanol Chemical compound NC1=CC(N)=CN=C1N1CC[N+](CCO)(CCO)CC1 TYQCGGYLZFNIGH-UHFFFAOYSA-N 0.000 claims description 2
- IJNRRJXMWZUENM-UHFFFAOYSA-N 2-[4-(3,5-diaminopyridin-2-yl)-1-methylpiperazin-1-ium-1-yl]ethanol Chemical compound C1C[N+](C)(CCO)CCN1C1=NC=C(N)C=C1N IJNRRJXMWZUENM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000973 cosmetic coloring agent Substances 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- ZYLZVPHMDYXABA-UHFFFAOYSA-N 2-[3-[2-[(3,5-diaminopyridin-2-yl)amino]ethyl]imidazol-1-ium-1-yl]ethanol Chemical compound NC1=CC(N)=CN=C1NCCN1C=[N+](CCO)C=C1 ZYLZVPHMDYXABA-UHFFFAOYSA-N 0.000 claims 1
- UXHWHIBYAYVCTE-UHFFFAOYSA-N 2-n-[2-(1-methylpiperidin-1-ium-1-yl)ethyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCC[N+]1(C)CCCCC1 UXHWHIBYAYVCTE-UHFFFAOYSA-N 0.000 claims 1
- ZALRAPPEXYIWRM-UHFFFAOYSA-N 2-n-[2-(3-methylimidazol-3-ium-1-yl)ethyl]pyridine-2,3,5-triamine Chemical compound C1=[N+](C)C=CN1CCNC1=NC=C(N)C=C1N ZALRAPPEXYIWRM-UHFFFAOYSA-N 0.000 claims 1
- CWXLMUPSSBPDIT-UHFFFAOYSA-N 2-n-[2-(4-methylmorpholin-4-ium-4-yl)ethyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCC[N+]1(C)CCOCC1 CWXLMUPSSBPDIT-UHFFFAOYSA-N 0.000 claims 1
- HILKPIHTRXQNDK-UHFFFAOYSA-N 2-n-[2-[2-(1-methylpiperidin-1-ium-1-yl)ethylamino]ethyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCCNCC[N+]1(C)CCCCC1 HILKPIHTRXQNDK-UHFFFAOYSA-N 0.000 claims 1
- ZRIZBWBFFQMFDY-UHFFFAOYSA-N 2-n-[2-[2-(1-methylpyrrolidin-1-ium-1-yl)ethoxy]ethyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCCOCC[N+]1(C)CCCC1 ZRIZBWBFFQMFDY-UHFFFAOYSA-N 0.000 claims 1
- ACGMJIZHXHJKHR-UHFFFAOYSA-N 2-n-[2-[2-(3-methylimidazol-3-ium-1-yl)ethylamino]ethyl]pyridine-2,3,5-triamine Chemical compound C1=[N+](C)C=CN1CCNCCNC1=NC=C(N)C=C1N ACGMJIZHXHJKHR-UHFFFAOYSA-N 0.000 claims 1
- CNHAGYLBJDANBB-UHFFFAOYSA-N 2-n-[2-[2-(4-methylmorpholin-4-ium-4-yl)ethylamino]ethyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCCNCC[N+]1(C)CCOCC1 CNHAGYLBJDANBB-UHFFFAOYSA-N 0.000 claims 1
- LMZKLOISSWUBIX-UHFFFAOYSA-N 2-n-[2-[3-(3-methylimidazol-3-ium-1-yl)propylamino]ethyl]pyridine-2,3,5-triamine Chemical compound C1=[N+](C)C=CN1CCCNCCNC1=NC=C(N)C=C1N LMZKLOISSWUBIX-UHFFFAOYSA-N 0.000 claims 1
- SNYQRTDXOVFIHT-UHFFFAOYSA-N 2-n-[3-(1-methylpiperidin-1-ium-1-yl)propyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCCC[N+]1(C)CCCCC1 SNYQRTDXOVFIHT-UHFFFAOYSA-N 0.000 claims 1
- NHCVVWDYAVMGNZ-UHFFFAOYSA-N 2-n-[3-(1-methylpyrrolidin-1-ium-1-yl)propyl]pyridine-2,3,5-triamine Chemical compound N=1C=C(N)C=C(N)C=1NCCC[N+]1(C)CCCC1 NHCVVWDYAVMGNZ-UHFFFAOYSA-N 0.000 claims 1
- FJPGIZBEXDJYSK-UHFFFAOYSA-N 2-n-[3-(3-methylimidazol-3-ium-1-yl)propyl]pyridine-2,3,5-triamine Chemical compound C1=[N+](C)C=CN1CCCNC1=NC=C(N)C=C1N FJPGIZBEXDJYSK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims 1
- ABYXFACYSGVHCW-UHFFFAOYSA-N pyridine-3,5-diamine Chemical compound NC1=CN=CC(N)=C1 ABYXFACYSGVHCW-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 238000007792 addition Methods 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000975 dye Substances 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 14
- 239000000982 direct dye Substances 0.000 description 14
- 238000004949 mass spectrometry Methods 0.000 description 14
- 239000002274 desiccant Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- 238000003760 magnetic stirring Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 0 C[N+](C)(C)C(CC1)CN1c(ncc(*)c1)c1N Chemical compound C[N+](C)(C)C(CC1)CN1c(ncc(*)c1)c1N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QLHVJBXAQWPEDI-UHFFFAOYSA-N 2-chloro-3,5-dinitropyridine Chemical compound [O-][N+](=O)C1=CN=C(Cl)C([N+]([O-])=O)=C1 QLHVJBXAQWPEDI-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002535 acidifier Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000002610 basifying agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application 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
- 239000003607 modifier Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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 2
- HWZGYBIFBNOPHH-UHFFFAOYSA-N 1-(3,5-dinitropyridin-2-yl)-4-methylpiperazine Chemical compound C1CN(C)CCN1C1=NC=C([N+]([O-])=O)C=C1[N+]([O-])=O HWZGYBIFBNOPHH-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-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
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- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- CSHLZYGRAHLJOB-UHFFFAOYSA-N n-(3-aminopyrazolo[1,5-a]pyridin-2-yl)acetamide Chemical compound C1=CC=CC2=C(N)C(NC(=O)C)=NN21 CSHLZYGRAHLJOB-UHFFFAOYSA-N 0.000 description 1
- BKEFUBHXUTWQED-UHFFFAOYSA-N n-(4-amino-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C(O)=C1 BKEFUBHXUTWQED-UHFFFAOYSA-N 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
- 210000003739 neck Anatomy 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960003371 protocatechualdehyde Drugs 0.000 description 1
- TYUPYVMUQSMZOW-UHFFFAOYSA-N pyrazolo[1,5-a]pyridin-3-amine Chemical compound C1=CC=CC2=C(N)C=NN21 TYUPYVMUQSMZOW-UHFFFAOYSA-N 0.000 description 1
- DIMNHIMUPFMCQG-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3,5-diamine Chemical compound C1=CC(N)=CC2=C(N)C=NN21 DIMNHIMUPFMCQG-UHFFFAOYSA-N 0.000 description 1
- HQRFNKWPPWDXOQ-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3,6-diamine Chemical compound C1=C(N)C=CC2=C(N)C=NN21 HQRFNKWPPWDXOQ-UHFFFAOYSA-N 0.000 description 1
- AMMRTECEGYRILQ-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3,7-diamine Chemical compound NC1=CC=CC2=C(N)C=NN21 AMMRTECEGYRILQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-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
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- 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
-
- 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
-
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
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- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
・一般式(I’)の化合物、それらの酸付加塩およびそれらの溶媒和物:
Z1は、酸素原子または基NR2であり;
R2は、水素原子または直鎖もしくは分岐のC1〜C4アルキルラジカル、ベンジルラジカルもしくはアセチルラジカルであり;
R1は、カチオン性ラジカルで置換されたまたは割り込まれた、1個以上の酸素原子でおよび/または1つ以上の基NR2で任意選択的に割り込まれた、ヒドロキシルおよびC1〜C4アルコキシもしくはヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、直鎖もしくは分岐の飽和C1〜C10アルキルラジカルであり、前記カチオン性ラジカルは、直鎖、分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;またはR1は、C1〜C4アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和、不飽和または芳香族の5〜8員環のカチオン性複素環であり;
Z1がNR2を表すとき;
・R1およびR2は、それらが結合している窒素原子と一緒に、C1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された不飽和の5〜8員環のカチオン性複素環を形成してもよく、この複素環は、NおよびOから選択される1つ以上のヘテロ原子、好ましくはNを含有する可能性があり、または
・R1およびR2は、それらが結合している窒素原子と一緒に、カチオン性ラジカルで置換された、そしてC1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された不飽和の5〜8員環の非カチオン性複素環を形成してもよく;前記カチオン性ラジカルは、直鎖、分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;
Rは、水素原子と、フッ素、塩素および臭素から選択されるハロゲンと、直鎖もしくは分岐のC1〜C4アルキル、カルボキシル(−COOH)および(C1〜C4)アルコキシカルボニルラジカルとから選択され、
An−はアニオンまたはアニオンの混合物を表す]
・以下の化合物、それらの酸付加塩およびそれらの溶媒和物:
1−(3,5−ジアミノピリジン−2−イル)−N,N,N−トリメチルピロリジン−3−アンモニウム、
4−(3,5−ジアミノピリジン−2−イル)−1−(2−ヒドロキシエチル)−1−メチルピペラジン−1−イウム、
4−(3,5−ジアミノピリジン−2−イル)−1,1−ビス(2−ヒドロキシエチル)ピペラジン−1−イウム、
4−(3,5−ジアミノピリジン−2−イル)(2−トリメチルエタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)(2−トリメチルメタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)(2−メチルジエチルエタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)(2−メチルジエチルメタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)−2−モルホリン−1,1−ジメチルピロリジニウム、
(3,5−ジアミノピリジン−2−イル)−3−トリメチルピペリジンアンモニウム、
(3,5−ジアミノピリジン−2−イル)−4−トリメチルピペリジンアンモニウム
から選択されるカチオン性アミノピリジンに関する。
の化合物に関する。
Rは、水素原子と、フッ素、塩素および臭素から選択されるハロゲンと、直鎖もしくは分岐のC1〜C4アルキル、カルボキシル(−COOH)および(C1〜C4)アルコキシカルボニルラジカルとから選択される)
の化合物から出発して、本発明によるカチオン性アミノピリジンの合成方法であって、
この順に、少なくとも次の工程:
・上に定義された基Z1R1での基Xの置換、
・ニトロ基の還元
を含む前記方法に関する。
Z1は、酸素原子または基NR2であり;
R2は、水素原子であるか、直鎖もしくは分岐のC1〜C4アルキルラジカル、ベンジルラジカルまたはアセチルラジカルであり;
R1は、カチオン性ラジカルで置換されたまたは割り込まれた、1個以上の酸素原子でおよび/または1つ以上の基NR2で任意選択的に割り込まれた、ヒドロキシルおよびC1〜C4アルコキシもしくはヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、直鎖もしくは分岐の飽和C1〜C10アルキルラジカルであり、前記カチオン性ラジカルは、直鎖もしくは分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;またはR1は、C1〜C4アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和、不飽和または芳香族の5〜8員環のカチオン性複素環であり;
Z1がNR2を表すとき;
・R1およびR2は、それらが結合している窒素原子と一緒に、その環メンバーの少なくとも1つが第四級アンモニウムであり、C1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和もしくは不飽和の5〜8員環のカチオン性複素環を形成してもよく、この複素環は、NおよびOから選択される1つ以上のヘテロ原子、好ましくはNを含有する可能性があり、または
・R1およびR2は、それらが結合している窒素原子と一緒に、カチオン性ラジカルで置換された、そしてC1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和もしくは不飽和の5〜8員環の非カチオン性複素環を形成してもよく;前記カチオン性ラジカルは、直鎖もしくは分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;
Rは、水素原子と、フッ素、塩素および臭素から選択されるハロゲンと、直鎖もしくは分岐のC1〜C4アルキル、カルボキシル(−COOH)および(C1〜C4)アルコキシカルボニルラジカルとから選択され、
An−はアニオンまたはアニオンの混合物を表す]
のケラチン繊維、とりわけ毛髪などのヒトのケラチン繊維の染色のためのカプラーとしての使用に関する。
Z1は、酸素原子または基NR2であり;
R2は、水素原子であるか、直鎖もしくは分岐のC1〜C4アルキルラジカル、ベンジルラジカルまたはアセチルラジカルであり;
R1は、カチオン性ラジカルで置換されたまたは割り込まれた、1個以上の酸素原子でおよび/または1つ以上の基NR2で任意選択的に割り込まれた、ヒドロキシルおよびC1〜C4アルコキシもしくはヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、直鎖もしくは分岐の飽和C1〜C10アルキルラジカルであるかまたはR1は、C1〜C4アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された飽和、不飽和または芳香族の5〜8員環のカチオン性複素環であり;前記カチオン性ラジカルは、直鎖もしくは分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;
Z1がNR2を表すとき;
・R1およびR2は、それらが結合している窒素原子と一緒に、その環メンバーの少なくとも1つが第四級アンモニウムであり、C1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和もしくは不飽和の5〜8員環のカチオン性複素環を形成してもよく、この複素環は、NおよびOから選択される1つ以上のヘテロ原子、好ましくはNを含有する可能性があり、または
・R1およびR2は、それらが結合している窒素原子と一緒に、カチオン性ラジカルで置換された、そしてC1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和もしくは不飽和の5〜8員環の非カチオン性複素環を形成してもよく;前記カチオン性ラジカルは、直鎖もしくは分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;
Rは、水素原子と、フッ素、塩素および臭素から選択されるハロゲンと、直鎖もしくは分岐のC1〜C4アルキル、カルボキシル(−COOH)および(C1〜C4)アルコキシカルボニルラジカルとから選択され、
An−はアニオンまたはアニオンの混合物を表す]
を含む、とりわけ毛髪などのケラチン繊維を染色するための化粧品組成物に関する。
− 1,3−ジメチル−2−[[4−(ジメチルアミノ)フェニル]アゾ]−1H−イミダゾリウムクロリド、
− 1,3−ジメチル−2−[(4−アミノフェニル)アゾ]−1H−イミダゾリウムクロリド、
− 1−メチル−4−[(メチルフェニルヒドラゾノ)メチル]ピリジニウムメチルスルフェート
について最も特に言及されてもよい。
の化合物が挙げられる。
次の染料組成物を調製する:
Claims (15)
- ・一般式(I’)の化合物、それらの酸付加塩およびそれらの溶媒和物:
Z1は、酸素原子または基NR2であり;
R2は、水素原子または直鎖もしくは分岐のC1〜C4アルキルラジカル、ベンジルラジカルもしくはアセチルラジカルであり;
R1は、カチオン性ラジカルで置換されたまたは割り込まれた、1個以上の酸素原子でおよび/または1つ以上の基NR2で任意選択的に割り込まれた、ヒドロキシルおよびC1〜C4アルコキシもしくはヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、直鎖もしくは分岐の飽和C1〜C10アルキルラジカルであり、前記カチオン性ラジカルは、直鎖、分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;またはR1は、C1〜C4アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和、不飽和または芳香族の5−〜8員環のカチオン性複素環であり;
Z1がNR2を表すとき;
・R1およびR2は、それらが結合している窒素原子と一緒に、C1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された不飽和の5−〜8員環のカチオン性複素環を形成してもよく、この複素環は、NおよびOから選択される1つ以上のヘテロ原子を含有する可能性があり、または
・R1およびR2は、それらが結合している窒素原子と一緒に、カチオン性ラジカルで置換された、そしてC1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、不飽和の5−〜8員環の非カチオン性複素環を形成してもよく;前記カチオン性ラジカルは、直鎖、分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;
Rは、水素原子と、フッ素、塩素および臭素から選択されるハロゲンと、直鎖もしくは分岐のC1〜C4アルキル、カルボキシル(−COOH)および(C1〜C4)アルコキシカルボニルラジカルとから選択され、
An−はアニオンまたはアニオンの混合物を表す]
・以下の化合物、それらの酸付加塩およびそれらの溶媒和物:
1−(3,5−ジアミノピリジン−2−イル)−N,N,N−トリメチルピロリジン−3−アンモニウム、
4−(3,5−ジアミノピリジン−2−イル)−1−(2−ヒドロキシエチル)−1−メチルピペラジン−1−イウム、
4−(3,5−ジアミノピリジン−2−イル)−1,1−ビス(2−ヒドロキシエチル)ピペラジン−1−イウム、
4−(3,5−ジアミノピリジン−2−イル)(2−トリメチルエタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)(2−トリメチルメタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)(2−メチルジエチルエタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)(2−メチルジエチルメタン)モルホリンアンモニウム、
4−(3,5−ジアミノピリジン−2−イル)モルホリン}−2−1,1−ジメチルピロリジニウム、
(3,5−ジアミノピリジン−2−イル)−3−トリメチルピペリジンアンモニウム、
(3,5−ジアミノピリジン−2−イル)−4−トリメチルピペリジンアンモニウム
から選択されるカチオン性アミノピリジン。 - 前記カチオン性ラジカルが、N,N−ジメチルピペラジニウムまたは直鎖もしくは分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み、この第四級アンモニウムがタイプ−N+RaRbRcのものであり、同一であっても異なってもよいRa、RbおよびRcが、ヒドロキシルで置換されていてもよいC1〜C6アルキルラジカルを表し、RaおよびRbが、それらが結合している窒素原子と一緒に、飽和もしくは不飽和の5−〜8員環のカチオン性複素環を形成する可能性があり、前記ラジカルRcが、それが存在するとき、ヒドロキシルで置換されていてもよいC1〜C6アルキルラジカルである、請求項1に記載のカチオン性アミノピリジン。
- 前記第四級アンモニウムが、トリメチルアンモニウム、トリエチルアンモニウム、ジメチルエチルアンモニウム、ジエチルメチルアンモニウム、ジイソプロピルメチルアンモニウム、ジエチルプロピルアンモニウム、ヒドロキシエチルジエチルアンモニウム、ジ−β−ヒドロキシエチルメチルアンモニウム、トリ−β−ヒドロキシエチルアンモニウム、N−メチルピペリジニウム、N−メチルピロリジニウム、N−メチルモルホリニウム、イミダゾリウム、ヒドロキシエチルイミダゾリウム、メチルイミダゾリウムおよびN−メチルピペラジニウムラジカルから選択される、請求項2に記載のカチオン性アミノピリジン。
- R1が、請求項1〜3のいずれか一項に定義されるカチオン性ラジカルで置換されたまたは割り込まれた、1個以上の酸素原子でおよび/または1つ以上の基NR2で任意選択的に割り込まれた、ヒドロキシルラジカルで任意選択的に置換されたC1〜C8アルキルラジカルである、請求項1〜3のいずれか一項に記載のカチオン性アミノピリジン。
- Z1が、酸素原子であるか、またはR2が水素および直鎖もしくは分岐のC1〜C4アルキルラジカルから選択される状態でNR2であり、R1が、酸素原子でまたは基NHで任意選択的に割り込まれた、ヒドロキシルラジカルで任意選択的に置換された、そしてトリメチルアンモニウムおよびイミダゾリウムラジカルから選択されるカチオン性ラジカルで置換されたまたは割り込まれた、飽和の直鎖C2〜C8アルキルラジカルを表す、請求項1〜4のいずれか一項に記載のカチオン性アミノピリジン。
- Z1が基NR2であり、R1およびR2が、それらが結合している窒素原子と一緒に、C1〜C10アルキルおよびC1〜C 4 ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、不飽和の5−〜8員環のカチオン性複素環を形成する、請求項1〜4のいずれか一項に記載のカチオン性アミノピリジン。
- Z1が基NR2であり、R1およびR2が、それらが結合している窒素原子と一緒に、請求項1〜6のいずれか一項に定義されるカチオン性ラジカルで置換された、不飽和の5−〜8員環の非カチオン性複素環を形成する、請求項1〜4のいずれか一項に記載のカチオン性アミノピリジン。
- 次の化合物:2−[(3,5−ジアミノピリジン−2−イル)アミノ]−N,N,N−トリメチルエタンアンモニウム、2−[(3,5−ジアミノピリジン−2−イル)(メチル)アミノ]−N,N,N−トリメチルエタンアンモニウム、1−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}−1−メチルピペリジニウム、1−(3,5−ジアミノピリジン−2−イル)−N,N,N−トリメチルピロリジン−3−アンモニウム、1−{3−[(3,5−ジアミノピリジン−2−イル)アミノ]プロピル}−3−(2−ヒドロキシエチル)−1H−イミダゾール−3−イウム、1−{3−[(3,5−ジアミノピリジン−2−イル)アミノ]プロピル}−1−メチルピペリジニウム、1−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}−1−メチルピロリジニウム、1−{3−[(3,5−ジアミノピリジン−2−イル)アミノ]プロピル}−1−メチルピロリジニウム、1−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}−3−メチル−1H−イミダゾール−3−イウム、4−{3−[(3,5−ジアミノピリジン−2−イル)アミノ]プロピル}−4−メチルモルホリン−4−イウム、4−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}−4−メチルモルホリン−4−イウム、1−[2−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)エチル]−1−メチルピペリジニウム、1−[2−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)エチル]−1−メチルピロリジニウム、1−[2−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)エチル]−3−メチル−1H−イミダゾール−3−イウム、4−[2−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)エチル]−4−メチルモルホリン−4−イウム、2−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)−N,N,N−トリメチルエタンアンモニウム、3−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)−N,N,N−トリメチルプロパン−1−アンモニウム、2−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エトキシ}−N,N,N−トリメチルエタンアンモニウム、3−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エトキシ}−N,N,N−トリメチルプロパン−1−アンモニウム、1−(2−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エトキシ}エチル)−1−メチルピペリジニウム、1−(2−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エトキシ}エチル)−1−メチルピロリジニウム、1−{3−[(3,5−ジアミノピリジン−2−イル)アミノ]プロピル}−3−メチル−1H−イミダゾール−3−イウム、1−[3−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)プロピル]−3−メチル−1H−イミダゾール−3−イウム、4−[3−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)プロピル]−1,1−ジメチルピペラジン−1−イウム、1−(3−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エトキシ}プロピル)−1−メチルピペリジニウム、4−[3−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)プロピル]−4−メチルモルホリン−4−イウム、1−[3({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)プロピル]−1−メチルピロリジニウム、3−({2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}アミノ)−N−エチル−N−メチル−N−プロピルプロパン−1−アンモニウム、3−[(3,5−ジアミノピリジン−2−イル)アミノ]−N,N,N−トリメチルプロパン−1−アンモニウム、3−[(3,5−ジアミノピリジン−2−イル)(メチル)アミノ]−N,N,N−トリメチルプロパン−1−アンモニウム、3−[(3,5−ジアミノピリジン−2−イル)オキシ]−N,N,N−トリメチルプロパン−1−アンモニウム、1−{2−[(3,5−ジアミノピリジン−2−イル)アミノ]エチル}−3−(2−ヒドロキシエチル)−1H−イミダゾール−3−イウム、4−(3,5−ジアミノピリジン−2−イル)−1−(2−ヒドロキシエチル)−1−メチルピペラジン−1−イウム、4−(3,5−ジアミノピリジン−2−イル)−1,1−ビス(2−ヒドロキシエチル)ピペラジン−1−イウム、4−(3,5−ジアミノピリジン−2−イル)(2−トリメチルエタン)モルホリンアンモニウム、4−(3,5−ジアミノピリジン−2−イル)(2−メチルジエチルエタン)モルホリンアンモニウム、4−(3,5−ジアミノピリジン−2−イル)−2−モルホリン−1,1−ジメチルピロリジニウム、(3,5−ジアミノピリジン−2−イル)−3−トリメチルピペリジンアンモニウム、(3,5−ジアミノピリジン−2−イル)−4−トリメチルピペリジンアンモニウム、4−(3,5−ジアミノピリジン−2−イル)(2−トリメチルメタン)モルホリンアンモニウム、4−(3,5−ジアミノピリジン−2−イル)(2−メチルジエチルメタン)モルホリンアンモニウムから選択される、請求項1〜7のいずれか一項に記載のカチオン性アミノピリジン。
- 好適な染色媒体中に、
− 少なくとも1つの酸化塩基、
− 少なくとも1つの一般式(I)のカチオン性カプラー、その酸付加塩およびその溶媒和物:
Z1は、酸素原子または基NR2であり;
R2は、水素原子であるか、または直鎖もしくは分岐のC1〜C4アルキルラジカル、ベンジルラジカルもしくはアセチルラジカルであり;
R1は、カチオン性ラジカルで置換されたまたは割り込まれた、1個以上の酸素原子でおよび/または1つ以上の基NR2で任意選択的に割り込まれた、ヒドロキシルおよびC1〜C4アルコキシもしくはヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、直鎖もしくは分岐の飽和C1〜C10アルキルラジカルであり、前記カチオン性ラジカルは、直鎖、分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;またはR1は、C1〜C4アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された飽和、不飽和または芳香族の5−〜8員環のカチオン性複素環であり;
Z1がNR2を表すとき;
・R1およびR2は、それらが結合している窒素と一緒に、その環メンバーの少なくとも1つが第四級アンモニウムであり、C1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和もしくは不飽和の5−〜8員環のカチオン性複素環を形成してもよく、この複素環は、NおよびOから選択される1つ以上のヘテロ原子を含有する可能性があり、または
・R1およびR2は、それらが結合している窒素と一緒に、カチオン性ラジカルで置換された、ならびにC1〜C10アルキル、ヒドロキシル、C1〜C4アルコキシ、アミノ、(C1〜C4)アルキルアミノ、ジ(C1〜C4)アルキルアミノ、チオ、(C1〜C4)アルキルチオ、カルボキシル、(C1〜C4)アルキルカルボニル、スルホニル、アミドおよびC1〜C4ヒドロキシアルキルラジカルから選択される1つ以上のラジカルで任意選択的に置換された、飽和もしくは不飽和の5−〜8員環の非カチオン性複素環を形成してもよく;前記カチオン性ラジカルは、直鎖、分岐もしくは環状の飽和もしくは不飽和ラジカルであって第四級アンモニウムを含み;
Rは、水素原子と、フッ素、塩素および臭素から選択されるハロゲンと、直鎖もしくは分岐のC1〜C4アルキル、カルボキシル(−COOH)および(C1〜C4)アルコキシカルボニルラジカルから選択され、
An−はアニオンまたはアニオンの混合物を表す]、
− ならびに少なくとも1つの酸化剤
を含む、すぐに使用できる化粧品染料組成物。 - 式(I)の前記カチオン性カプラーにおいて、Z1が基NR2であり、R1およびR2が、それらが結合している窒素原子と一緒に、C1〜C4ヒドロキシアルキルおよびC1〜C4アルキルラジカルから選択される1つ以上のラジカルで置換されたピペリジニウム、イミダゾリウム、ピロリジニウム、モルホリニウムまたはピペラジニウムラジカルから選択される、飽和もしくは不飽和の5−〜8員環のカチオン性複素環を形成する、請求項10に記載のすぐに使用できる化粧品染料組成物。
- 前記酸化剤が、過酸化水素、ウレアペルオキシド、アルカリ金属臭素酸塩、過酸塩、過酸およびオキシダーゼ酵素から選択される請求項10〜12のいずれか一項に記載のすぐに使用できる化粧品染料組成物。
- 好適な染色媒体中に、請求項1〜8または請求項10〜11のいずれか一項に定義される少なくとも1つのカチオン性アミノピリジンを含む化粧品染料組成物が、酸化剤の存在下に所望の着色を発現するのに十分な時間、ケラチン繊維に適用され、前記酸化剤が前記組成物の前に、それと同時にまたはそれの後に適用されることを特徴とする、前記ケラチン繊維の染色方法。
- 請求項10〜12に定義されるようにケラチン繊維を染色するための化粧品組成物を含有する第1区画、および酸化剤を含有する第2区画を有する多区画デバイス。
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Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2968970B1 (fr) * | 2010-12-17 | 2021-09-03 | Oreal | Composition tinctoriale comprenant au moins 4 precurseurs de coloration dont au moins une base d'oxydation et au moins un coupleur |
FR2968967B1 (fr) * | 2010-12-17 | 2013-10-04 | Oreal | Composition tinctoriale comprenant une base d'oxydation pyrazolopyridine secondaire et un coupleur 3,5-diamino pyridine cationique |
WO2012080286A2 (en) * | 2010-12-17 | 2012-06-21 | L'oreal | Dyeing composition comprising a heterocyclic oxidation base and a cationic 3,5-diaminopyridine coupler |
CN102344411B (zh) * | 2011-08-01 | 2013-05-15 | 宜兴市新宇化工有限公司 | 一种制备2,6-二甲氧基-3,5-二氨基吡啶盐酸盐的方法 |
FR2979343B1 (fr) * | 2011-08-25 | 2013-10-04 | Oreal | Coupleurs pyridiniques cationiques, composition tinctoriale comprenant une 6-hydroxy-pyridine cationique, procedes et utilisations |
JP6571930B2 (ja) * | 2014-12-08 | 2019-09-04 | ホーユー株式会社 | カプラー含有組成物 |
FR3030244B1 (fr) * | 2014-12-17 | 2018-07-06 | L'oreal | Composition de coloration comprenant une base d'oxydation para-phenylenediamine et un coupleur particulier |
FR3030233B1 (fr) | 2014-12-17 | 2016-12-09 | Oreal | Composition de coloration comprenant une base d'oxydation para-phenylenediamine, et un polymere amphotere ou cationique dans un milieu riche en corps gras |
FR3030243B1 (fr) | 2014-12-17 | 2018-11-09 | L'oreal | Composition de coloration comprenant une base d'oxydation para-phenylenediamine et une base d'oxydation heterocyclique |
FR3030234B1 (fr) | 2014-12-17 | 2018-05-18 | Oreal | Composition de coloration comprenant une base d'oxydation para-phenylenediamine, un tensio actif non ionique dans un milieu riche en corps gras |
FR3030255B1 (fr) | 2014-12-17 | 2016-12-23 | Oreal | Composition de coloration comprenant une base d'oxydation para-phenylenediamine, un epaississant polysaccharide dans un milieu riche en corps gras |
FR3030237B1 (fr) | 2014-12-17 | 2017-07-14 | Oreal | Composition de coloration comprenant une base d'oxydation para-phenylenediamine, un tensio actif amphotere dans un milieu riche en corps gras |
FR3071835B1 (fr) * | 2017-09-29 | 2019-09-27 | L'oreal | Bases para-phenylenediamines a heterocycles cationiques et leur utilisation pour la teinture d’oxydation des fibres keratiniques |
CN113402454A (zh) * | 2021-05-26 | 2021-09-17 | 华东理工大学 | 氨基吡啶型季铵盐阳离子表面活性剂、制备方法及应用 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE626050A (ja) | 1962-03-30 | |||
DE1492175A1 (de) | 1965-07-07 | 1970-02-12 | Schwarzkopf Gmbh Hans | Verfahren zum Faerben von lebenden Haaren |
US3306903A (en) * | 1965-10-07 | 1967-02-28 | Council Scient Ind Res | 1-aminopyridyl-4-(phenyl or pyridyl)-piperazines and intermediates |
DE2359399C3 (de) | 1973-11-29 | 1979-01-25 | Henkel Kgaa, 4000 Duesseldorf | Haarfärbemittel |
LU83900A1 (fr) * | 1982-01-26 | 1983-09-02 | Oreal | Nouveaux composes utilisables pour la teinture des cheveux,leur procede de preparation,composition de teinture les contenant et procede de teinture de cheveux correspondant |
FR2586913B1 (fr) | 1985-09-10 | 1990-08-03 | Oreal | Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede |
JPS63169571A (ja) | 1987-01-06 | 1988-07-13 | Nec Corp | ト−ン検出装置 |
DE3843892A1 (de) | 1988-12-24 | 1990-06-28 | Wella Ag | Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate |
JPH0563124A (ja) | 1991-09-03 | 1993-03-12 | Mitsubishi Electric Corp | 混成集積回路装置 |
DE4133957A1 (de) | 1991-10-14 | 1993-04-15 | Wella Ag | Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate |
JP3071931B2 (ja) * | 1992-03-05 | 2000-07-31 | 花王株式会社 | 2−(アリール置換アルコキシ)−3,5−ジアミノピリジン誘導体及びこれを使用する角質繊維染色組成物 |
DE4234887A1 (de) | 1992-10-16 | 1994-04-21 | Wella Ag | Oxidationshaarfärbemittel mit einem Gehalt an 4,5-Diaminopyrazolderivaten sowie neue 4,5-Diaminopyrazolderivate und Verfahren zu ihrer Herstellung |
DE4234885A1 (de) | 1992-10-16 | 1994-04-21 | Wella Ag | Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten, deren Verwendung zum Färben von Haaren sowie neue Pyrazol-Derivate |
TW311089B (ja) | 1993-07-05 | 1997-07-21 | Ciba Sc Holding Ag | |
TW325998B (en) | 1993-11-30 | 1998-02-01 | Ciba Sc Holding Ag | Dyeing keratin-containing fibers |
ES2215944T3 (es) | 1994-11-03 | 2004-10-16 | Ciba Specialty Chemicals Holding Inc. | Colorantes imidazolazoicos cationicos. |
DE4440957A1 (de) | 1994-11-17 | 1996-05-23 | Henkel Kgaa | Oxidationsfärbemittel |
FR2733749B1 (fr) | 1995-05-05 | 1997-06-13 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation |
DE19539264C2 (de) | 1995-10-21 | 1998-04-09 | Goldwell Gmbh | Haarfärbemittel |
DE19543988A1 (de) | 1995-11-25 | 1997-05-28 | Wella Ag | Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
FR2776288B1 (fr) * | 1998-03-20 | 2001-04-06 | Oreal | Nouveaux coupleurs cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
FR2776289B1 (fr) * | 1998-03-20 | 2001-02-02 | Oreal | Composition de teinture d'oxydation contenant un coupleur cationique, procedes de teinture, nouveaux coupleurs cationiques |
FR2801308B1 (fr) | 1999-11-19 | 2003-05-09 | Oreal | COMPOSITIONS DE TEINTURE DE FIBRES KERATINIQUES CONTENANT DE DES 3-AMINO PYRAZOLO-[1,(-a]-PYRIDINES, PROCEDE DE TEINTURE, NOUVELLES 3-AMINO PYRAZOLO-[1,5-a]-PYRIDINES |
FR2806908B1 (fr) * | 2000-03-30 | 2002-12-20 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
WO2002058659A1 (en) * | 2001-01-23 | 2002-08-01 | P&G-Clairol, Inc. | Couplers for oxidative coloration of hair |
FR2832148B1 (fr) * | 2001-11-14 | 2004-05-21 | Oreal | Nouvelles bases d'oxydation 2,5-diaminopyridine utiles pour la teinture des fibres keratiniques |
WO2003060015A1 (en) * | 2002-01-15 | 2003-07-24 | Ciba Speciality Chemicals Holding Inc. | Yellow cationic dyes for dying of organic material |
US7175670B2 (en) * | 2003-03-13 | 2007-02-13 | L'oreal S.A. | Couplers of 2,3,5-triaminopyridine and use of the same for dyeing keratin fibers |
FR2852240B1 (fr) * | 2003-03-13 | 2007-10-05 | Oreal | Nouveaux coupleurs du type 2,3,5-triaminopyridine et utilisation de ces coupleurs pour la teinture des fibres keratiniques |
US7288124B2 (en) * | 2004-09-08 | 2007-10-30 | L'oreal S.A. | Heteroaromatic binuclear black direct dyes |
FR2874821B1 (fr) * | 2004-09-08 | 2006-10-20 | Oreal | Nouveaux colorants directs noirs di-noyaux heteroaromatiques |
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2009
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JP2013512936A (ja) | 2013-04-18 |
US8491669B2 (en) | 2013-07-23 |
EP2509951B1 (en) | 2016-04-13 |
EP2509951A1 (en) | 2012-10-17 |
BR112012013759A2 (pt) | 2017-03-28 |
FR2953517A1 (fr) | 2011-06-10 |
US20130048007A1 (en) | 2013-02-28 |
BR112012013759B1 (pt) | 2017-11-21 |
ES2575105T3 (es) | 2016-06-24 |
CN102712592A (zh) | 2012-10-03 |
CN102712592B (zh) | 2015-10-14 |
WO2011069898A1 (en) | 2011-06-16 |
FR2953517B1 (fr) | 2012-04-27 |
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