JP2010540419A5 - - Google Patents
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- JP2010540419A5 JP2010540419A5 JP2010525375A JP2010525375A JP2010540419A5 JP 2010540419 A5 JP2010540419 A5 JP 2010540419A5 JP 2010525375 A JP2010525375 A JP 2010525375A JP 2010525375 A JP2010525375 A JP 2010525375A JP 2010540419 A5 JP2010540419 A5 JP 2010540419A5
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- JP
- Japan
- Prior art keywords
- group
- formula
- precursor
- alkyl
- representing
- Prior art date
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- 239000002243 precursor Substances 0.000 claims description 70
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 238000004043 dyeing Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 150000003573 thiols Chemical class 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- -1 anionic ion Chemical class 0.000 claims 7
- 239000000835 fiber Substances 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 102000011782 Keratins Human genes 0.000 claims 6
- 108010076876 Keratins Proteins 0.000 claims 6
- 125000000129 anionic group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000007447 staining method Methods 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 5
- 125000002091 cationic group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 claims 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000002537 cosmetic Substances 0.000 claims 4
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 3
- 125000006685 (C1-C6) polyhaloalkyl group Chemical group 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- IZPNVUYQWBZYEA-UHFFFAOYSA-N 1,4-dimethylpyridin-1-ium Chemical compound CC1=CC=[N+](C)C=C1 IZPNVUYQWBZYEA-UHFFFAOYSA-N 0.000 claims 2
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 claims 2
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 claims 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 claims 2
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 claims 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 claims 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims 2
- RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 claims 2
- PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 claims 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 claims 2
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 claims 2
- NVLTWXMZECWWPC-UHFFFAOYSA-N 3-hydroxy-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1OC NVLTWXMZECWWPC-UHFFFAOYSA-N 0.000 claims 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims 2
- WBIZZNFQJPOKDK-UHFFFAOYSA-N 4-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=CC(O)=CC=C1C=O WBIZZNFQJPOKDK-UHFFFAOYSA-N 0.000 claims 2
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 claims 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 150000001768 cations Chemical group 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000005496 phosphonium group Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 claims 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims 2
- 125000005649 substituted arylene group Chemical group 0.000 claims 2
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 claims 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims 2
- JYHAOJGBXVCDOC-GGWOSOGESA-N (2e,4e)-5-[4-(dimethylamino)phenyl]penta-2,4-dienal Chemical compound CN(C)C1=CC=C(\C=C\C=C\C=O)C=C1 JYHAOJGBXVCDOC-GGWOSOGESA-N 0.000 claims 1
- AKQUHUJZRFFZOO-UHFFFAOYSA-N 1,2,3,3-tetramethylindol-1-ium Chemical compound C1=CC=C2C(C)(C)C(C)=[N+](C)C2=C1 AKQUHUJZRFFZOO-UHFFFAOYSA-N 0.000 claims 1
- ZZWIVZMYSVNULV-UHFFFAOYSA-N 1,2,3-trimethylbenzimidazol-3-ium Chemical compound C1=CC=C2[N+](C)=C(C)N(C)C2=C1 ZZWIVZMYSVNULV-UHFFFAOYSA-N 0.000 claims 1
- UMZDENILBZKMFY-UHFFFAOYSA-N 1,2-dimethylpyridin-1-ium Chemical compound CC1=CC=CC=[N+]1C UMZDENILBZKMFY-UHFFFAOYSA-N 0.000 claims 1
- KEOLYURDXNRJEY-UHFFFAOYSA-N 1,2-dimethylquinolin-1-ium Chemical compound C1=CC=CC2=[N+](C)C(C)=CC=C21 KEOLYURDXNRJEY-UHFFFAOYSA-N 0.000 claims 1
- OHQGKTJQWANGLW-UHFFFAOYSA-N 1,4-dimethylquinolin-1-ium Chemical compound C1=CC=C2C(C)=CC=[N+](C)C2=C1 OHQGKTJQWANGLW-UHFFFAOYSA-N 0.000 claims 1
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 claims 1
- CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 claims 1
- QBQDROYKEQDPRX-UHFFFAOYSA-N 2,3-dimethyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](C)=C(C)SC2=C1 QBQDROYKEQDPRX-UHFFFAOYSA-N 0.000 claims 1
- SKITZVIJHXHTQV-UHFFFAOYSA-N 2,3-dimethylisoquinolin-2-ium Chemical compound C1=CC=C2C=[N+](C)C(C)=CC2=C1 SKITZVIJHXHTQV-UHFFFAOYSA-N 0.000 claims 1
- UIDDBKQHVSHHNO-UHFFFAOYSA-N 2,4,6-trimethylpyrylium Chemical compound CC1=CC(C)=[O+]C(C)=C1 UIDDBKQHVSHHNO-UHFFFAOYSA-N 0.000 claims 1
- AFUKNJHPZAVHGQ-UHFFFAOYSA-N 2,5-dimethoxy-Benzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1 AFUKNJHPZAVHGQ-UHFFFAOYSA-N 0.000 claims 1
- YIQGLTKAOHRZOL-UHFFFAOYSA-N 2-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(OC)=CC=C21 YIQGLTKAOHRZOL-UHFFFAOYSA-N 0.000 claims 1
- SPNULQAFNCKAPD-UHFFFAOYSA-N 2-methyl-3-propyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](CCC)=C(C)SC2=C1 SPNULQAFNCKAPD-UHFFFAOYSA-N 0.000 claims 1
- XSEOLEIVLCYZQR-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-3-ium-3-yl)propane-1-sulfonate Chemical compound C1=CC=C2[N+](CCCS([O-])(=O)=O)=C(C)SC2=C1 XSEOLEIVLCYZQR-UHFFFAOYSA-N 0.000 claims 1
- TXKOSPRGZFVRGP-UHFFFAOYSA-N 3-(4-methylpyridin-1-ium-1-yl)propane-1-sulfonic acid;hydroxide Chemical compound [OH-].CC1=CC=[N+](CCCS(O)(=O)=O)C=C1 TXKOSPRGZFVRGP-UHFFFAOYSA-N 0.000 claims 1
- WHTCGOGITOSXEO-UHFFFAOYSA-N 3-(4-methylquinolin-1-ium-1-yl)propane-1-sulfonic acid;hydroxide Chemical compound [OH-].C1=CC=C2C(C)=CC=[N+](CCCS(O)(=O)=O)C2=C1 WHTCGOGITOSXEO-UHFFFAOYSA-N 0.000 claims 1
- IPCKZBYIMYSTDV-UHFFFAOYSA-N 3-(5-methoxy-2-methyl-1,3-benzothiazol-3-ium-3-yl)propane-1-sulfonic acid;hydroxide Chemical compound [OH-].COC1=CC=C2SC(C)=[N+](CCCS(O)(=O)=O)C2=C1 IPCKZBYIMYSTDV-UHFFFAOYSA-N 0.000 claims 1
- JBTJVIBZVXRERL-UHFFFAOYSA-N 3-ethyl-2,4-dimethyl-1,3-thiazol-3-ium Chemical compound CC[N+]=1C(C)=CSC=1C JBTJVIBZVXRERL-UHFFFAOYSA-N 0.000 claims 1
- OGRZMXBJGTZUGN-UHFFFAOYSA-N 3-ethyl-2-methyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](CC)=C(C)SC2=C1 OGRZMXBJGTZUGN-UHFFFAOYSA-N 0.000 claims 1
- PAWXTPSQTMYBSB-UHFFFAOYSA-N 3-ethyl-2-methyl-1,3-benzoxazol-3-ium Chemical class C1=CC=C2[N+](CC)=C(C)OC2=C1 PAWXTPSQTMYBSB-UHFFFAOYSA-N 0.000 claims 1
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 claims 1
- VNWPLOWYHIDMEB-UHFFFAOYSA-N 4-(dibutylamino)benzaldehyde Chemical compound CCCCN(CCCC)C1=CC=C(C=O)C=C1 VNWPLOWYHIDMEB-UHFFFAOYSA-N 0.000 claims 1
- HGDRXADJVGVGBC-UHFFFAOYSA-N 4-(dimethylamino)-2-methoxybenzaldehyde Chemical compound COC1=CC(N(C)C)=CC=C1C=O HGDRXADJVGVGBC-UHFFFAOYSA-N 0.000 claims 1
- ZZSKDKGGUHLIFE-UHFFFAOYSA-N 4-(dimethylamino)-3-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1N(C)C ZZSKDKGGUHLIFE-UHFFFAOYSA-N 0.000 claims 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims 1
- XCQFZIFIUMBSAO-UHFFFAOYSA-N 4-(dimethylamino)naphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(N(C)C)=CC=C(C=O)C2=C1 XCQFZIFIUMBSAO-UHFFFAOYSA-N 0.000 claims 1
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 claims 1
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 claims 1
- LORPDGZOLAPNHP-UHFFFAOYSA-N 4-hydroxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(O)=CC=C(C=O)C2=C1 LORPDGZOLAPNHP-UHFFFAOYSA-N 0.000 claims 1
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 claims 1
- FSMYWBQIMDSGQP-UHFFFAOYSA-N 4-oxochromene-3-carbaldehyde Chemical compound C1=CC=C2C(=O)C(C=O)=COC2=C1 FSMYWBQIMDSGQP-UHFFFAOYSA-N 0.000 claims 1
- QQSONAPZEBELDW-UHFFFAOYSA-N 5,6-dichloro-1,3-diethyl-2-methylbenzimidazol-3-ium Chemical compound ClC1=C(Cl)C=C2N(CC)C(C)=[N+](CC)C2=C1 QQSONAPZEBELDW-UHFFFAOYSA-N 0.000 claims 1
- KMWCSNCNHSEXIF-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1N=CNC=1C=O KMWCSNCNHSEXIF-UHFFFAOYSA-N 0.000 claims 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 claims 1
- JSPGOHYLKVWWKI-UHFFFAOYSA-N 6-hydroxy-2h-chromene-3-carbaldehyde Chemical compound O1CC(C=O)=CC2=CC(O)=CC=C21 JSPGOHYLKVWWKI-UHFFFAOYSA-N 0.000 claims 1
- LZERQSJGPXFAKB-UHFFFAOYSA-N 6-methyl-1h-indole-3-carbaldehyde Chemical compound CC1=CC=C2C(C=O)=CNC2=C1 LZERQSJGPXFAKB-UHFFFAOYSA-N 0.000 claims 1
- GBWMIOYSMWCYIZ-UHFFFAOYSA-N 6-methyl-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(C)=CC=C21 GBWMIOYSMWCYIZ-UHFFFAOYSA-N 0.000 claims 1
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- PJNBUPKHRWAKAL-UHFFFAOYSA-N CC1=[N+](CCC([O-])=O)C2=CC(C)=CC=C2S1 Chemical compound CC1=[N+](CCC([O-])=O)C2=CC(C)=CC=C2S1 PJNBUPKHRWAKAL-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 101710088194 Dehydrogenase Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 238000004873 anchoring Methods 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- DKZBBWMURDFHNE-NSCUHMNNSA-N coniferyl aldehyde Chemical compound COC1=CC(\C=C\C=O)=CC=C1O DKZBBWMURDFHNE-NSCUHMNNSA-N 0.000 claims 1
- 150000002019 disulfides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 1
- 230000027756 respiratory electron transport chain Effects 0.000 claims 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 claims 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 claims 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims 1
- OTMRXENQDSQACG-UHFFFAOYSA-N thiophene-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)S1 OTMRXENQDSQACG-UHFFFAOYSA-N 0.000 claims 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims 1
- 235000012141 vanillin Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| FR0757808A FR2921258A1 (fr) | 2007-09-24 | 2007-09-24 | Composition tinctoriale comprenant au moins un precurseur incolore disulfures/thiol, proced de coloration a partir de la composition |
| US96074207P | 2007-10-11 | 2007-10-11 | |
| PCT/EP2008/062710 WO2009040354A1 (en) | 2007-09-24 | 2008-09-23 | Dye composition comprising at least one colorless disulfide/thiol precursor, and dyeing process using the composition |
Related Child Applications (1)
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| JP2015151000A Division JP6499037B2 (ja) | 2007-09-24 | 2015-07-30 | 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法 |
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| JP2010540419A JP2010540419A (ja) | 2010-12-24 |
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| JP2015151000A Expired - Fee Related JP6499037B2 (ja) | 2007-09-24 | 2015-07-30 | 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法 |
| JP2017160998A Pending JP2017203044A (ja) | 2007-09-24 | 2017-08-24 | 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法 |
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| JP2015151000A Expired - Fee Related JP6499037B2 (ja) | 2007-09-24 | 2015-07-30 | 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法 |
| JP2017160998A Pending JP2017203044A (ja) | 2007-09-24 | 2017-08-24 | 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法 |
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| EP (1) | EP2205681B1 (https=) |
| JP (3) | JP2010540419A (https=) |
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| CN (2) | CN103251513A (https=) |
| AT (1) | ATE522582T1 (https=) |
| BR (1) | BRPI0816004B1 (https=) |
| ES (1) | ES2368878T3 (https=) |
| FR (1) | FR2921258A1 (https=) |
| WO (1) | WO2009040354A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE518916T1 (de) | 2006-03-24 | 2011-08-15 | Oreal | Färbezusammensetzung mit einem thiol/disulfid- leuchtfarbstoff mit einem heterozyklus und einer internen kationischen ladung sowie verfahren zur aufhellung von keratinmaterial mit diesem farbstoff |
| EP2024444B1 (fr) | 2006-03-24 | 2011-07-06 | L'Oréal | Composition de teinture comprenant un colorant fluorescent naphtylimide thiol/disulfure, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| FR2898903B1 (fr) | 2006-03-24 | 2012-08-31 | Oreal | Composition de teinture comprenant un colorant disulfure fluorescent, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| FR2921377B1 (fr) | 2007-09-21 | 2009-10-30 | Oreal | Compose styryl a motif hydroxy(cyclo)alkylamino thiol/disulfure, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| FR2921376B1 (fr) | 2007-09-21 | 2009-10-30 | Oreal | Compose styryl tetrahydroquinolinium thiol/disulfure, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| FR2921381B1 (fr) | 2007-09-21 | 2009-10-30 | Oreal | Colorant hemicyanine styryle thiol/disulfure, composition tinctoriale comprenant ce colorant, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| FR2921373B1 (fr) | 2007-09-21 | 2009-10-30 | Oreal | Colorant derive d'indole styryle a linker alkylene, composition tinctoriale comprenant ce colorant, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| FR2968954B1 (fr) | 2010-12-15 | 2012-12-21 | Oreal | Procede de coloration de fibres keratiniques mettant en oeuvre un colorant direct a fonction disulfure/thiol/thiol protege et de la vapeur d'eau |
| WO2012112689A1 (en) * | 2011-02-15 | 2012-08-23 | The University Of North Carolina At Chapel Hill | Nanoparticle, liposomes, polymers, agents and proteins modified with reversible linkers |
| FR2971935B1 (fr) | 2011-02-25 | 2013-02-15 | Oreal | Composition pour colorer les fibres keratiniques comprenant un colorant direct a fonction disulfure/thiol, un polymere epaississant, un tensioactif non ionique, un agent alcalin, et un agent reducteur |
| FR2971938B1 (fr) | 2011-02-25 | 2013-08-02 | Oreal | Composition pour colorer les fibres keratiniques comprenant un colorant direct a fonction disulfure/thiol, un alcool gras faiblement ou non ethoxyle, un tensioactif cationique, un agent alcalin, et un agent reducteur |
| FR2971936B1 (fr) | 2011-02-25 | 2013-02-15 | Oreal | Composition pour colorer les fibres keratiniques comprenant un colorant direct a fonction disulfure/thiol, un tensioactif non ionique, un tensioactif amphotere, un alcool gras ethoxyle, un agent alcalin, et un agent reducteur |
| FR2971939B1 (fr) | 2011-02-25 | 2013-02-15 | Oreal | Composition pour colorer les fibres keratiniques comprenant un colorant direct a fonction disulfure/thiol, un corps gras, un agent alcalin, et un agent reducteur |
| MX345094B (es) | 2011-02-25 | 2017-01-17 | Oreal | Composicion para teñir fibras queratinicas que comprende un tinte directo que tiene un grupo funcional disulfuro/tiol, un polimero espesante, un alcohol graso etoxilado y/o un tensioactivo no ionico, un agente alcalino y un agente reductor. |
| FR2971937B1 (fr) | 2011-02-25 | 2013-02-15 | Oreal | Composition pour colorer les fibres keratiniques comprenant un colorant direct a fonction disulfure/thiol, un polymere epaississant non cellulosique, un agent alcalin, et un agent reducteur |
| FR2990944A1 (fr) | 2012-05-23 | 2013-11-29 | Oreal | Procede de coloration des fibres keratiniques comprenant un colorant /pigment, un compose photoactif, et une source lumineuse |
| RU2680068C2 (ru) | 2013-09-02 | 2019-02-14 | Л'Ореаль | Способ окрашивания кератиновых волокон с применением катионных стириловых дисульфидных красителей и композиция, содержащая указанные красители |
| CN105492078A (zh) * | 2013-09-03 | 2016-04-13 | 荷兰联合利华有限公司 | 评价头发颜色变化的方法 |
| FR3043551B1 (fr) | 2015-11-12 | 2017-11-24 | Oreal | Colorant direct cationique a chaine aliphatique et a fonction disulfure/thiol/thiol protege pour colorer les fibres keratiniques |
| FR3066108B1 (fr) | 2017-05-10 | 2020-10-30 | Oreal | Colorant direct fluorescent a chaine aliphatique et a fonction disulfure/thiol/thiol protege pour colorer les matieres keratiniques |
| FR3067599B1 (fr) | 2017-06-16 | 2020-09-04 | Oreal | Procede de coloration des matieres keratiniques mettant en oeuvre au moins un colorant bleu, violet ou vert et au moins un colorant fluorescent disulfure, thiol ou thiol protege |
| FR3067598B1 (fr) | 2017-06-16 | 2020-09-11 | Oreal | Procede de coloration des fibres keratiniques mettant en œuvre au moins un colorant fluorescent disulfure, thiol ou thiol protege et au moins un activateur comprenant un reducteur et moins deux agents alcalins differents |
| FR3067597B1 (fr) | 2017-06-16 | 2020-09-04 | Oreal | Procede de coloration des fibres keratiniques mettant en œuvre au moins un colorant direct et au moins un colorant fluorescent disulfure, thiol ou thiol protege |
| CN114015003A (zh) * | 2021-11-17 | 2022-02-08 | 长春工业大学 | 一种基于香草醛含亚胺结构可降解聚氨酯弹性体及其制备方法 |
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| BE544768A (https=) | 1955-01-28 | |||
| NL105936C (https=) | 1956-07-17 | |||
| DE1544506A1 (de) | 1965-01-02 | 1970-04-16 | Hoechst Ag | Verfahren zur Herstellung von basischen Azofarbstoffen |
| JPS548626A (en) | 1977-06-23 | 1979-01-23 | Hodogaya Chem Co Ltd | Basic dye pyrido(1.2-a)indolium |
| DK140584A (da) * | 1983-03-08 | 1984-09-09 | Bristol Myers Co | Fremgangsmaade til fremstilling af carbapenemderivater |
| US4880922A (en) * | 1985-11-22 | 1989-11-14 | Bristol-Myers Company | Carbapenems with quaternized heterothioalkylthio substitution at position 2 |
| US5034014A (en) * | 1990-06-18 | 1991-07-23 | Clairol, Inc. | Hair dye composition and method |
| DE19842071A1 (de) * | 1998-09-15 | 2000-03-16 | Henkel Kgaa | Verfahren zum Färben von keratinhaltigen Fasern unter Verwendung von stabilen Diazoniumsalzen |
| FR2787708B1 (fr) | 1998-12-23 | 2002-09-13 | Oreal | Procede de teinture mettant en oeuvre un compose a methylene actif et un compose choisi parmi un aldehyde, une cetone, une quinone et un derive de la di-imino-isoindoline ou de la 3-amino-isoindolone |
| BR0007437A (pt) * | 1999-01-08 | 2001-11-20 | Procter & Gamble | Composições tópicas que compreendem tióisfuncionais protegidos |
| US6114350A (en) * | 1999-04-19 | 2000-09-05 | Nen Life Science Products, Inc. | Cyanine dyes and synthesis methods thereof |
| DE19936911A1 (de) * | 1999-08-05 | 2001-02-08 | Henkel Kgaa | Mittel zum Färben von keratinhaltigen Fasern |
| DE19951134A1 (de) * | 1999-10-23 | 2001-04-26 | Henkel Kgaa | Mittel zum Färben von keratinhaltigen Fasern |
| EP1133975B1 (en) | 2000-03-17 | 2008-02-13 | Kao Corporation | Use of a compound for dyeing hair |
| DE10148844A1 (de) | 2001-10-04 | 2003-04-10 | Henkel Kgaa | Mittel zum Färben von keratinhaltigen Fasern |
| JP2003246940A (ja) * | 2002-02-27 | 2003-09-05 | Fuji Photo Film Co Ltd | シアニン色素の製造方法 |
| EP2168634B1 (en) * | 2002-09-13 | 2012-12-19 | Kao Corporation | Hair dye composition comprising methine dye |
| WO2005097051A2 (en) | 2004-04-08 | 2005-10-20 | Ciba Specialty Chemicals Holding Inc. | Disulfide dyes, composition comprising them and method of dyeing hair |
| US7488354B2 (en) * | 2004-10-14 | 2009-02-10 | L'oreal S.A. | Dyeing composition comprising at least one disulphide dye and method of dyeing human keratin fibers using this dye |
| FR2876576B1 (fr) | 2004-10-14 | 2006-12-08 | Oreal | Composition de teinture comprenant un colorant disulfure particulier et procede de coloration des fibres keratiniques humaines a partir de ce colorant |
| US7247713B2 (en) | 2004-12-15 | 2007-07-24 | L'oreal, S.A. | Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
| FR2879195B1 (fr) | 2004-12-15 | 2007-03-02 | Oreal | Composes diazoiques symetriques a groupements 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif |
| DE102005026545A1 (de) * | 2005-06-08 | 2006-12-21 | Henkel Kgaa | Mehrkomponentenmittel zum Färben keratinischer Fasern |
| ES2328068T3 (es) * | 2005-06-16 | 2009-11-06 | Basf Se | Colorantes del tipo esteril sulfuro. |
| EP2530261B1 (en) * | 2005-09-23 | 2014-04-30 | JP Scope, Inc. | Valve apparatus for an internal combustion engine |
| CN100451003C (zh) * | 2005-11-17 | 2009-01-14 | 复旦大学 | 含巯基的分子整流材料及其制备方法 |
-
2007
- 2007-09-24 FR FR0757808A patent/FR2921258A1/fr active Pending
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2008
- 2008-09-23 CN CN2013101264360A patent/CN103251513A/zh active Pending
- 2008-09-23 KR KR1020107006385A patent/KR101235549B1/ko not_active Expired - Fee Related
- 2008-09-23 WO PCT/EP2008/062710 patent/WO2009040354A1/en not_active Ceased
- 2008-09-23 EP EP08804624A patent/EP2205681B1/en not_active Not-in-force
- 2008-09-23 JP JP2010525375A patent/JP2010540419A/ja active Pending
- 2008-09-23 CN CN200880108729.3A patent/CN101802107B/zh not_active Expired - Fee Related
- 2008-09-23 AT AT08804624T patent/ATE522582T1/de not_active IP Right Cessation
- 2008-09-23 BR BRPI0816004A patent/BRPI0816004B1/pt not_active IP Right Cessation
- 2008-09-23 US US12/679,665 patent/US8034125B2/en not_active Expired - Fee Related
- 2008-09-23 ES ES08804624T patent/ES2368878T3/es active Active
-
2015
- 2015-07-30 JP JP2015151000A patent/JP6499037B2/ja not_active Expired - Fee Related
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2017
- 2017-08-24 JP JP2017160998A patent/JP2017203044A/ja active Pending
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