BRPI0816004B1 - processo para tingir as fibras queratínicas, compostos, composição cosmética e dispositivo com múltiplos compartimentos - Google Patents
processo para tingir as fibras queratínicas, compostos, composição cosmética e dispositivo com múltiplos compartimentos Download PDFInfo
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- BRPI0816004B1 BRPI0816004B1 BRPI0816004A BRPI0816004A BRPI0816004B1 BR PI0816004 B1 BRPI0816004 B1 BR PI0816004B1 BR PI0816004 A BRPI0816004 A BR PI0816004A BR PI0816004 A BRPI0816004 A BR PI0816004A BR PI0816004 B1 BRPI0816004 B1 BR PI0816004B1
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- 238000000034 method Methods 0.000 title claims abstract description 89
- 230000008569 process Effects 0.000 title claims abstract description 63
- 102000011782 Keratins Human genes 0.000 title claims abstract description 53
- 108010076876 Keratins Proteins 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 title claims description 80
- 239000000835 fiber Substances 0.000 title claims description 63
- 150000001875 compounds Chemical class 0.000 title claims description 57
- 239000002537 cosmetic Substances 0.000 title claims description 21
- 238000004043 dyeing Methods 0.000 title abstract description 21
- 239000002243 precursor Substances 0.000 claims abstract description 158
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- -1 aromatic dialdehyde disulfide compound Chemical class 0.000 claims description 141
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 150000003573 thiols Chemical class 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000004434 sulfur atom Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000002091 cationic group Chemical group 0.000 claims description 22
- 239000003638 chemical reducing agent Substances 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000129 anionic group Chemical group 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 150000001299 aldehydes Chemical class 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000004001 thioalkyl group Chemical group 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 230000000269 nucleophilic effect Effects 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002019 disulfides Chemical class 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052705 radium Inorganic materials 0.000 claims description 5
- 229910052701 rubidium Inorganic materials 0.000 claims description 5
- IZPNVUYQWBZYEA-UHFFFAOYSA-N 1,4-dimethylpyridin-1-ium Chemical compound CC1=CC=[N+](C)C=C1 IZPNVUYQWBZYEA-UHFFFAOYSA-N 0.000 claims description 4
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 claims description 4
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 claims description 4
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 4
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 claims description 4
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims description 4
- WBIZZNFQJPOKDK-UHFFFAOYSA-N 4-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=CC(O)=CC=C1C=O WBIZZNFQJPOKDK-UHFFFAOYSA-N 0.000 claims description 4
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 claims description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 4
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005496 phosphonium group Chemical group 0.000 claims description 4
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 claims description 4
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 4
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims description 4
- UMZDENILBZKMFY-UHFFFAOYSA-N 1,2-dimethylpyridin-1-ium Chemical compound CC1=CC=CC=[N+]1C UMZDENILBZKMFY-UHFFFAOYSA-N 0.000 claims description 3
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 125000005649 substituted arylene group Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- 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 description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- CDICDSOGTRCHMG-ONEGZZNKSA-N (E)-sinapaldehyde Chemical compound COC1=CC(\C=C\C=O)=CC(OC)=C1O CDICDSOGTRCHMG-ONEGZZNKSA-N 0.000 claims description 2
- 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 description 2
- JGMOEJGFQBJKAX-UHFFFAOYSA-N 1,2-dimethyl-2h-quinoline Chemical compound C1=CC=C2N(C)C(C)C=CC2=C1 JGMOEJGFQBJKAX-UHFFFAOYSA-N 0.000 claims description 2
- ZBHTYKLLIUCNEF-UHFFFAOYSA-N 1,4-dimethyl-2h-quinoline Chemical compound C1=CC=C2N(C)CC=C(C)C2=C1 ZBHTYKLLIUCNEF-UHFFFAOYSA-N 0.000 claims description 2
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 claims description 2
- SOEVTPGSXVPSHZ-UHFFFAOYSA-N 1-ethyl-2-methyl-2h-quinoline Chemical compound C1=CC=C2N(CC)C(C)C=CC2=C1 SOEVTPGSXVPSHZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- YWDPCFDDLFDDMI-UHFFFAOYSA-N 2,3-dimethyl-1h-isoquinoline Chemical compound C1=CC=C2C=C(C)N(C)CC2=C1 YWDPCFDDLFDDMI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 claims description 2
- VNWPLOWYHIDMEB-UHFFFAOYSA-N 4-(dibutylamino)benzaldehyde Chemical compound CCCCN(CCCC)C1=CC=C(C=O)C=C1 VNWPLOWYHIDMEB-UHFFFAOYSA-N 0.000 claims description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- FSMYWBQIMDSGQP-UHFFFAOYSA-N 4-oxochromene-3-carbaldehyde Chemical compound C1=CC=C2C(=O)C(C=O)=COC2=C1 FSMYWBQIMDSGQP-UHFFFAOYSA-N 0.000 claims description 2
- XQMQGXDUQPLVES-UHFFFAOYSA-N 5-chloro-3-ethyl-2-methyl-1,3-benzothiazol-3-ium Chemical compound C1=C(Cl)C=C2[N+](CC)=C(C)SC2=C1 XQMQGXDUQPLVES-UHFFFAOYSA-N 0.000 claims description 2
- KMWCSNCNHSEXIF-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1N=CNC=1C=O KMWCSNCNHSEXIF-UHFFFAOYSA-N 0.000 claims description 2
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 claims description 2
- LZERQSJGPXFAKB-UHFFFAOYSA-N 6-methyl-1h-indole-3-carbaldehyde Chemical compound CC1=CC=C2C(C=O)=CNC2=C1 LZERQSJGPXFAKB-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 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 description 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 2
- OOFWCWCUKUVTKD-UHFFFAOYSA-N Sinapaldehyde Natural products COC1=CC(C=CC(C)=O)=CC(OC)=C1O OOFWCWCUKUVTKD-UHFFFAOYSA-N 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
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims description 2
- DKZBBWMURDFHNE-NSCUHMNNSA-N coniferyl aldehyde Chemical compound COC1=CC(\C=C\C=O)=CC=C1O DKZBBWMURDFHNE-NSCUHMNNSA-N 0.000 claims description 2
- 239000000834 fixative Substances 0.000 claims description 2
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000879 imine group Chemical group 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 claims description 2
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 claims description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims description 2
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- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 2
- RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 claims 2
- YNMGRZLDRLHRTN-UHFFFAOYSA-N 1,2,3,3-tetramethyl-2h-indole Chemical compound C1=CC=C2C(C)(C)C(C)N(C)C2=C1 YNMGRZLDRLHRTN-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
- AFUKNJHPZAVHGQ-UHFFFAOYSA-N 2,5-dimethoxy-Benzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1 AFUKNJHPZAVHGQ-UHFFFAOYSA-N 0.000 claims 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-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
- 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
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical class O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims 1
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- 150000003254 radicals Chemical class 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
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- 238000011282 treatment Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 12
- 239000000982 direct dye Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 11
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- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000003774 sulfhydryl reagent Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0816004A2 BRPI0816004A2 (pt) | 2018-03-27 |
| BRPI0816004B1 true BRPI0816004B1 (pt) | 2018-08-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| BRPI0816004A BRPI0816004B1 (pt) | 2007-09-24 | 2008-09-23 | processo para tingir as fibras queratínicas, compostos, composição cosmética e dispositivo com múltiplos compartimentos |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8034125B2 (enExample) |
| EP (1) | EP2205681B1 (enExample) |
| JP (3) | JP2010540419A (enExample) |
| KR (1) | KR101235549B1 (enExample) |
| CN (2) | CN103251513A (enExample) |
| AT (1) | ATE522582T1 (enExample) |
| BR (1) | BRPI0816004B1 (enExample) |
| ES (1) | ES2368878T3 (enExample) |
| FR (1) | FR2921258A1 (enExample) |
| WO (1) | WO2009040354A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007110531A2 (fr) | 2006-03-24 | 2007-10-04 | L'oréal | Composition de teinture comprenant un colorant fluorescent naphtylimide thiol/disulfure, procede d'eclaircissement des matieres keratiniques a partir de ce colorant |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| EP2677996B1 (en) | 2011-02-25 | 2017-11-29 | L'Oréal | Composition for dyeing keratinous fibres comprising a direct dye having a disulphide/thiol functional group, a thickening polymer, an ethoxylated fatty alcohol and/or a nonionic surfactant, an alkaline agent and a reducing agent |
| 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 |
| 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 |
| KR102244166B1 (ko) | 2013-09-02 | 2021-04-26 | 로레알 | 양이온성 스티릴 디술파이드 염료를 사용하는 케라틴 섬유 염색 방법, 및 상기 염료를 포함하는 조성물 |
| JP2016529509A (ja) * | 2013-09-03 | 2016-09-23 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 毛髪の色の変化を評価する方法 |
| 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 |
| 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 |
| 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 |
| 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 |
Family Cites Families (26)
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| BE544768A (enExample) | 1955-01-28 | |||
| NL219021A (enExample) | 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 |
| AR241016A1 (es) * | 1983-03-08 | 1991-04-30 | Bristol Myeres Squibb Company | "derivados de aminotiol cuaternario, procedimiento para prepararlos y procedimiento para preparar compuestos de carbapenem a partir de dichos derivados". |
| 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 |
| WO2000040210A2 (en) * | 1999-01-08 | 2000-07-13 | The Procter & Gamble Company | Topical compositions comprising protected functional thiols |
| 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 |
| EP1407756B2 (en) * | 2002-09-13 | 2016-09-28 | Kao Corporation | Hair dye composition comprising methine dye |
| JP5274832B2 (ja) | 2004-04-08 | 2013-08-28 | チバ ホールディング インコーポレーテッド | 二硫化染料、それを含む組成物及び毛を染める方法 |
| 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 |
| 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 |
| 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 |
| 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 |
| DE102005026545A1 (de) * | 2005-06-08 | 2006-12-21 | Henkel Kgaa | Mehrkomponentenmittel zum Färben keratinischer Fasern |
| WO2006134043A2 (en) * | 2005-06-16 | 2006-12-21 | Ciba Specialty Chemicals Holding Inc. | Styryl sulfide dyes |
| JP4913147B2 (ja) * | 2005-09-23 | 2012-04-11 | ジェイピー スコープ エルエルシー | 内燃機関の弁装置 |
| 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 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 KR KR1020107006385A patent/KR101235549B1/ko not_active Expired - Fee Related
- 2008-09-23 CN CN2013101264360A patent/CN103251513A/zh active Pending
- 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 US US12/679,665 patent/US8034125B2/en not_active Expired - Fee Related
- 2008-09-23 ES ES08804624T patent/ES2368878T3/es active Active
- 2008-09-23 BR BRPI0816004A patent/BRPI0816004B1/pt not_active IP Right Cessation
-
2015
- 2015-07-30 JP JP2015151000A patent/JP6499037B2/ja not_active Expired - Fee Related
-
2017
- 2017-08-24 JP JP2017160998A patent/JP2017203044A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010540419A (ja) | 2010-12-24 |
| US8034125B2 (en) | 2011-10-11 |
| ES2368878T3 (es) | 2011-11-23 |
| ATE522582T1 (de) | 2011-09-15 |
| CN103251513A (zh) | 2013-08-21 |
| BRPI0816004A2 (pt) | 2018-03-27 |
| CN101802107B (zh) | 2014-08-27 |
| KR20100043292A (ko) | 2010-04-28 |
| JP2015193663A (ja) | 2015-11-05 |
| JP6499037B2 (ja) | 2019-04-10 |
| CN101802107A (zh) | 2010-08-11 |
| EP2205681B1 (en) | 2011-08-31 |
| WO2009040354A1 (en) | 2009-04-02 |
| FR2921258A1 (fr) | 2009-03-27 |
| KR101235549B1 (ko) | 2013-02-21 |
| JP2017203044A (ja) | 2017-11-16 |
| EP2205681A1 (en) | 2010-07-14 |
| US20110016642A1 (en) | 2011-01-27 |
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| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time |
Free format text: REFERENTE A 14A ANUIDADE. |
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| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |
Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2689 DE 19-07-2022 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |