JP7303695B2 - 香料組成物 - Google Patents
香料組成物 Download PDFInfo
- Publication number
- JP7303695B2 JP7303695B2 JP2019145298A JP2019145298A JP7303695B2 JP 7303695 B2 JP7303695 B2 JP 7303695B2 JP 2019145298 A JP2019145298 A JP 2019145298A JP 2019145298 A JP2019145298 A JP 2019145298A JP 7303695 B2 JP7303695 B2 JP 7303695B2
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- JP
- Japan
- Prior art keywords
- methyl
- perfume
- olfactory
- channel
- composition
- 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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- 239000002304 perfume Substances 0.000 title claims description 108
- 239000000203 mixture Substances 0.000 title claims description 77
- 239000003205 fragrance Substances 0.000 claims description 55
- 235000019645 odor Nutrition 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 19
- 238000011156 evaluation Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 7
- 230000005068 transpiration Effects 0.000 claims description 6
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims description 4
- 230000007423 decrease Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 description 51
- 239000000047 product Substances 0.000 description 43
- 239000002994 raw material Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- -1 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol 3,8,8,11a-tetramethyldodecahydro-1H-3,5a-epoxynaphtho[2,1-c]oxepine Chemical compound 0.000 description 25
- 238000001514 detection method Methods 0.000 description 24
- 239000000523 sample Substances 0.000 description 19
- 230000001427 coherent effect Effects 0.000 description 18
- 239000011521 glass Substances 0.000 description 17
- YPZUZOLGGMJZJO-UHFFFAOYSA-N Ambronide Chemical compound C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 10
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- GWCRPYGYVRXVLI-UHFFFAOYSA-N 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone Chemical compound CCC1OC(C)=C(O)C1=O GWCRPYGYVRXVLI-UHFFFAOYSA-N 0.000 description 8
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 8
- UUQHKWMIDYRWHH-UHFFFAOYSA-N Methyl beta-orcinolcarboxylate Chemical compound COC(=O)C1=C(C)C=C(O)C(C)=C1O UUQHKWMIDYRWHH-UHFFFAOYSA-N 0.000 description 8
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 8
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 8
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 8
- QRPLZGZHJABGRS-UHFFFAOYSA-N xi-5-Dodecanolide Chemical compound CCCCCCCC1CCCC(=O)O1 QRPLZGZHJABGRS-UHFFFAOYSA-N 0.000 description 8
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 7
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 7
- 230000008447 perception Effects 0.000 description 7
- 239000001069 triethyl citrate Substances 0.000 description 7
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 7
- 235000013769 triethyl citrate Nutrition 0.000 description 7
- NOTCZLKDULMKBR-UHFFFAOYSA-N 3-Methoxy-5-methylphenol Chemical compound COC1=CC(C)=CC(O)=C1 NOTCZLKDULMKBR-UHFFFAOYSA-N 0.000 description 6
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PZSJOBKRSVRODF-UHFFFAOYSA-N vanillin acetate Chemical compound COC1=CC(C=O)=CC=C1OC(C)=O PZSJOBKRSVRODF-UHFFFAOYSA-N 0.000 description 6
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 6
- YJVLDTISLGRQTJ-KPFXUCSBSA-N (1R,8R,10S,13R)-5,5,7,9,9,13-hexamethyl-4,6-dioxatetracyclo[6.5.1.01,10.03,7]tetradecane Chemical compound C1[C@@]23[C@H](C)CC[C@H]2C(C)(C)[C@]1([H])C1(C)OC(C)(C)OC1C3 YJVLDTISLGRQTJ-KPFXUCSBSA-N 0.000 description 5
- DRTBYQJIHFSKDT-UHFFFAOYSA-N 2-methyl-5-phenylpentan-1-ol Chemical compound OCC(C)CCCC1=CC=CC=C1 DRTBYQJIHFSKDT-UHFFFAOYSA-N 0.000 description 5
- JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 5
- WXCMHFPAUCOJIG-UHFFFAOYSA-N 4'-tert-Butyl-2',6'-dimethyl-3',5'-dinitroacetophenone Chemical compound CC(=O)C1=C(C)C([N+]([O-])=O)=C(C(C)(C)C)C([N+]([O-])=O)=C1C WXCMHFPAUCOJIG-UHFFFAOYSA-N 0.000 description 5
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 5
- SWUIQEBPZIHZQS-UHFFFAOYSA-N calone Chemical compound O1CC(=O)COC2=CC(C)=CC=C21 SWUIQEBPZIHZQS-UHFFFAOYSA-N 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 5
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 5
- HZYHMHHBBBSGHB-UHFFFAOYSA-N (2E,6E)-2,6-Nonadienal Natural products CCC=CCCC=CC=O HZYHMHHBBBSGHB-UHFFFAOYSA-N 0.000 description 4
- VKHRHKWELUTFKM-WRRARIKVSA-N (2E,6Z)-nona-2,6-dienal Chemical compound CC\C=C/CC\C=C\C=O.CC\C=C/CC\C=C\C=O VKHRHKWELUTFKM-WRRARIKVSA-N 0.000 description 4
- ZFGBKXBPHOUSJX-CLFYSBASSA-N (5z)-3-methylcyclotetradec-5-en-1-one Chemical compound CC1C\C=C/CCCCCCCCC(=O)C1 ZFGBKXBPHOUSJX-CLFYSBASSA-N 0.000 description 4
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 description 4
- GUMOJENFFHZAFP-UHFFFAOYSA-N 2-Ethoxynaphthalene Chemical compound C1=CC=CC2=CC(OCC)=CC=C21 GUMOJENFFHZAFP-UHFFFAOYSA-N 0.000 description 4
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 4
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 4
- WJWBVJLPGOYBGM-UHFFFAOYSA-N 2-cyclohexylhepta-1,6-dien-3-one Chemical compound C=CCCC(=O)C(=C)C1CCCCC1 WJWBVJLPGOYBGM-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- UKZXPOJABTXLMK-UHFFFAOYSA-N 3-[2-methyl-4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CCC=O)C(C)=C1 UKZXPOJABTXLMK-UHFFFAOYSA-N 0.000 description 4
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 4
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 4
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 4
- RVOKNSFEAOYULQ-UHFFFAOYSA-N 8-Mercapto-p-menthan-3-one Chemical compound CC1CCC(C(C)(C)S)C(=O)C1 RVOKNSFEAOYULQ-UHFFFAOYSA-N 0.000 description 4
- GITDWIBIPJFPDK-UHFFFAOYSA-N 8-ethyl-1-oxaspiro[4.5]decan-2-one Chemical compound C1CC(CC)CCC11OC(=O)CC1 GITDWIBIPJFPDK-UHFFFAOYSA-N 0.000 description 4
- COWIMPXRUUJKQF-UHFFFAOYSA-N 8-methyl-1-oxaspiro[4.5]decan-2-one Chemical compound C1CC(C)CCC11OC(=O)CC1 COWIMPXRUUJKQF-UHFFFAOYSA-N 0.000 description 4
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 description 4
- FZJUFJKVIYFBSY-UHFFFAOYSA-N bourgeonal Chemical compound CC(C)(C)C1=CC=C(CCC=O)C=C1 FZJUFJKVIYFBSY-UHFFFAOYSA-N 0.000 description 4
- IEPWIPZLLIOZLU-ARJAWSKDSA-N cis-3-Hexenyl salicylate Chemical compound CC\C=C/CCOC(=O)C1=CC=CC=C1O IEPWIPZLLIOZLU-ARJAWSKDSA-N 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000005923 long-lasting effect Effects 0.000 description 4
- FDSIFWDGJSJXMP-UHFFFAOYSA-N methyl 3-methyl-5-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazole-4-carboxylate Chemical compound CC1=NOC(C2=NOC(C)=C2)=C1C(=O)OC FDSIFWDGJSJXMP-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
- SAOSCTYRONNFTC-UHFFFAOYSA-N methyl-capric acid Natural products CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 4
- UNYNVICDCJHOPO-UHFFFAOYSA-N sotolone Chemical compound CC1OC(=O)C(O)=C1C UNYNVICDCJHOPO-UHFFFAOYSA-N 0.000 description 4
- BJIOGJUNALELMI-ONEGZZNKSA-N trans-isoeugenol Chemical compound COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 4
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 4
- ALRYNTSLFYRKGF-UHFFFAOYSA-N (4-methylphenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=CC=C(C)C=C1 ALRYNTSLFYRKGF-UHFFFAOYSA-N 0.000 description 3
- IVCJGAUQMMORNE-YRNVUSSQSA-N (E)-9-hydroxy-5,9-dimethyldec-4-enal Chemical compound CC(O)(C)CCCC(/C)=C/CCC=O IVCJGAUQMMORNE-YRNVUSSQSA-N 0.000 description 3
- KHQDWCKZXLWDNM-KPKJPENVSA-N (e)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound CC\C(CO)=C/CC1CC=C(C)C1(C)C KHQDWCKZXLWDNM-KPKJPENVSA-N 0.000 description 3
- MKEIDVFLAWJKMY-UHFFFAOYSA-N 1,7-dioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCCCCO1 MKEIDVFLAWJKMY-UHFFFAOYSA-N 0.000 description 3
- IOFYRNMXFRRJPS-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexen-1-yl)pent-4-en-1-one Chemical compound CC1(C)CCCC(C(=O)CCC=C)=C1 IOFYRNMXFRRJPS-UHFFFAOYSA-N 0.000 description 3
- WXALIABDZXPJLE-UHFFFAOYSA-N 2,4-diethoxy-5-methylpyrimidine Chemical compound CCOC1=NC=C(C)C(OCC)=N1 WXALIABDZXPJLE-UHFFFAOYSA-N 0.000 description 3
- JIJOZOBTAJWEID-UHFFFAOYSA-N 2-[2-(3,3,5-trimethylcyclohexyl)acetyl]cyclopentan-1-one Chemical compound C1C(C)(C)CC(C)CC1CC(=O)C1C(=O)CCC1 JIJOZOBTAJWEID-UHFFFAOYSA-N 0.000 description 3
- KNHGOYVXAHUDHP-UHFFFAOYSA-N 2-[2-(4-methylcyclohex-3-en-1-yl)propyl]cyclopentan-1-one Chemical compound C1CC(C)=CCC1C(C)CC1CCCC1=O KNHGOYVXAHUDHP-UHFFFAOYSA-N 0.000 description 3
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- VLFBSPUPYFTTNF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methylpropanal Chemical compound COC1=CC=C(CC(C)C=O)C=C1 VLFBSPUPYFTTNF-UHFFFAOYSA-N 0.000 description 3
- TZJLGGWGVLADDN-UHFFFAOYSA-N 4-(3,4-Methylenedioxyphenyl)-2-butanone Chemical compound CC(=O)CCC1=CC=C2OCOC2=C1 TZJLGGWGVLADDN-UHFFFAOYSA-N 0.000 description 3
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- NKCQEIXYLHACJC-UHFFFAOYSA-N 6-propan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)C)=CC=C21 NKCQEIXYLHACJC-UHFFFAOYSA-N 0.000 description 3
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- QILMAYXCYBTEDM-IWQZZHSRSA-N Isoambrettolide Chemical compound O=C1CCCCCCC\C=C/CCCCCCO1 QILMAYXCYBTEDM-IWQZZHSRSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002386 air freshener Substances 0.000 description 3
- JKRWZLOCPLZZEI-UHFFFAOYSA-N alpha-Trichloromethylbenzyl acetate Chemical compound CC(=O)OC(C(Cl)(Cl)Cl)C1=CC=CC=C1 JKRWZLOCPLZZEI-UHFFFAOYSA-N 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PHNCACYNYORRNS-UHFFFAOYSA-N dodecahydro-3,8,8,11a-tetramethyl-5h-3,5a-epoxynaphth(2,1-c)oxepin Chemical compound CC1(C)CCCC2(C)C3CCC(C)(O4)OCC34CCC21 PHNCACYNYORRNS-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IUSBVFZKQJGVEP-SNAWJCMRSA-N isoeugenol acetate Chemical compound COC1=CC(\C=C\C)=CC=C1OC(C)=O IUSBVFZKQJGVEP-SNAWJCMRSA-N 0.000 description 3
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
- B05B11/00—Single-unit hand-held apparatus in which flow of contents is produced by the muscular force of the operator at the moment of use
- B05B11/01—Single-unit hand-held apparatus in which flow of contents is produced by the muscular force of the operator at the moment of use characterised by the means producing the flow
- B05B11/06—Gas or vapour producing the flow, e.g. from a compressible bulb or air pump
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
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Description
本発明の他の側面において、香料組成物の作製方法であって、対流中に配置されるとき、その香料組成物の性質および嗅覚プロファイルを、その源からの、ある距離において、信頼可能かつ認識可能な臭気とともに検出することができるような、前記方法が提供される。
A=[log(ODTa);log(HSa)] および B=[log(ODTb);log(HSb)]
により得られる、に存在しなければならないことを見出した。
臭気計は、キャリアガス中のオドラントの線形希釈の原理に基づいて機能する。配置されるオドラントの量は、その蒸気圧およびキャリアガス流に依存する。フローレギュレータにより調節される窒素の一定の流れにより、オドラントが、サンプル容器から混合チャンバへと搬送される。そこで、キャリアガス・臭気混合物は、無臭性空気で希釈される。混合チャンバから、希釈された臭気性空気の一部が、フューズドシリカ毛細管を介してスニッフィングフンネルへと流れるのを許容する。混合チャンバからスニッフィングフンネルへの臭気性空気の用量を決定する、毛細管を介する流速は、PCにより1~256mlで二元性ステップで調節することができるバルブの開口に依存する。臭気性空気サンプルの最終希釈は、8lt/minの流速で、無臭性空気で恒久的にそれらをフラッシュすることにより、ガラスフンネル中で生じる。スイッチの1ポジションのみがオドラント送達毛細管をスニッフィングフンネル中へと浸入させ、他の2つのポジションにおいて毛細管はフンネル外に位置し、流出物は吸引放出される、特別な自動化チャネル設定デバイスにより、矯正選択トライアングルプレゼンテーションが達成される。それぞれの試行後に、チャンネル設定は自動的に、ランダムな順序で変更する。濃度は、オドラント蒸気圧からおよび、蒸気圧飽和が達成されると想定すると、臭気系に適用された希釈率から、計算される。対照として、毛細管流出物からヘッドスペースフィルタ中への公知の容量をサンプリングすることにより、または脱離液中のオドラントの後続のガスクロマトグラフィ定量化により、濃度が分析的に決定される。
a) 有向性空気流れを作り出して発するためのデバイスを提供すること、
b) デバイスに香料組成物のサンプルを、空気流れの経路に配置されるように設置すること、
c) 香料組成物を空気流れに取込み(entrain)、香料組成物が実質的に閉じ込められた香り付きプルームとして、それをデバイスから放出させること、
d) 香り付きプルームをチャネルに沿って、該チャネルの開口部へと、その開口部において香り付きプルームのにおいを嗅いで判断できる規定の距離で、向けること。
(i) 香料サンプルを一定時間T1の間、開放環境中で、20~35℃の温度で蒸散するのを許容させること、ここでT1は好ましくは30分よりも長く、より好ましくは60分よりも長く、および最も好ましくは少なくとも120分である、
(ii) 32±2℃の温度に維持されたデバイスに、該サンプルを挿入すること、
(iii) 嗅覚特徴およびにおい強度を、時間の関数として、チャネル(図2中の長方形BDFH)の出口で評価すること、および
(iv) 特定時間T2後、出口から開始して下流へと移動する、チャネル(図2のABEF)のトップにおける異なる場所において、時間間隔T3内に、においの嗅覚特徴および強度を任意に評価すること。
1) 76.4%エタノール、10%クエン酸トリエチルおよび3.6%水を含む溶媒混合物中の、0.24重量%のRADJANOL(2-エチル-4-(2,2,3-トリメチル-3-シクロペンタン-1-イル)-2-ブテン-1-オール;2-エチル-4-(2’,2’,3-トリメチルシクロペンタ-3’-エニル)ブタ-2-エノール)の10マイクロリットルの溶液を、ガラスプレート上で、標準的な室内条件(20±2℃、50±20%相対湿度)下で4時間蒸散させて、図2に記載するように、2m長さのチャネルの出口において、1~10のスケールで、4.5±0.5の平均強度で原料を評価する90%よりも多いパネリストにより検知させる。このスケールは、測定条件下で辛うじて気付くことができる臭気強さを有する原料が1の強度が与えられ、一方で測定条件下で、考えられ得る最も強いにおいを作り出す原料に10の強度が与えられるように、規定され得る。CYCLOHEAL~(4-(4-ヒドロキシ-4-メチルペンチル)シクロヘキサ-3-エン カルバルデヒド)~、これは本明細書においてベンチマークとして用いられる、のノートを評価することにより、さらに較正する;および
(Z)-オキサシクロヘプタデカ-10-エン-2-オン;4-メトキシベンズアルデヒド;3-(4-(tert-ブチル)フェニル)プロパナール;2-(2-メルカプトプロパン-2-イル)-5-メチルシクロヘキサノン;(Z)-3-メチルシクロテトラデカ-5-エノン;4-(4-ヒドロキシ-4-メチルペンチル)シクロヘキサ-3-エンカルバルデヒド;(E)-1-(2,6,6-トリメチルシクロヘキサ-1,3-ジエン-1-イル)ブタ-2-エン-1-オン;(E)-1-(2,6,6-トリメチルシクロヘキサ-1-エン-1-イル)ブタ-2-エン-1-オン;(E)-1-(2,6,6-トリメチルシクロヘキサ-3-エン-1-イル)ブタ-2-エン-1-オン;6-ペンチルテトラヒドロ-2H-ピラン-2-オン;2-(2-(3,3,5-トリメチルシクロヘキシル)アセチル)シクロペンタノン;6-ヘプチルテトラヒドロ-2H-ピラン-2-オン;8-エチル-1-オキサスピロ[4.5]デカン-2-オン;6-ペンチルテトラヒドロ-2H-ピラン-2-オン;4-アリル-2-メトキシフェノール;3-(3-イソプロピルフェニル)ブタナール;1-(3,3-ジメチルシクロヘキサ-1-エン-1-イル)ペンタ-4-エン-1-オン;;;2-イソブチルキノリン;(E)-2-メトキシ-4-(プロパ-1-エン-1-イル)フェノール;6-イソプロピルキノリン;(1-メチル-2-((1,2,2-トリメチルビシクロ[3.1.0]ヘキサン-3-イル)メチル)シクロプロピル)メタノール;3-(4-(tert-ブチル)フェニル)-2-メチルプロパナール;3-メチル-5-フェニルペンタノール;8-メチル-1-オキサスピロ[4.5]デカン-2-オン;2-アミノ安息香酸メチル;2-(2-(4-メチルシクロヘキサ-3-エン-1-イル)プロピル)シクロペンタノン;(2E,6Z)-ノナ-2,6-ジエナール;5-ヘプチルジヒドロフラン-2(3H)-オン;2-シクロヘキシルヘプタ-1,6-ジエン-3-オン;(E)-2-エチル-4-(2,2,3-トリメチルシクロペンタ-3-エン-1-イル)ブタ-2-エン-1-オール;;4-メチレン-2-フェニルテトラヒドロ-2H-ピラン;(Z)-ヘキサ-3-エン-1-イル 2-ヒドロキシベンゾエート;2,4-ジエトキシ-5-メチルピリミジン;(2E,6Z)-ノナ-2,6-ジエンニトリル;パチュリ油;(E)-9-ヒドロキシ-5,9-ジメチルデカ-4-エナール;3-(4-イソブチル-2-メチルフェニル)プロパナール;2-(2-(4-メチルシクロヘキサ-3-エン-1-イル)アリル)シクロペンタノン。
1) グループ2から選択される原料の重量パーセント(wt%)での濃度の合計が、少なくとも10wt%、より特別には10wt%~100wt%、より特別には25wt%~90wt%、およびなおより特別には40wt%~70wt%である、
および
2) グループ3、4および5の原料の濃度の合計が、それぞれの原料が合計において1度のみカウントされて、少なくとも5wt%、より特別には5~60wt%、より特別には7.5wt%~50%、およびなおより特別には10wt%~40wt%である。
および/または
3) グループ5から選択される原料の濃度の合計が、少なくとも0.1wt%、特別には0.1wt%~30wt%、より特別には0.5wt%~20wt%、およびなおより特別には1wt%~15wt%である。
所望の効果を提供するために、送達ビヒクル中に配合されてもよい。送達ビヒクルは、カプセル技術を含み得る。代わりに、送達ビヒクルは、固体支持体、例えばポリマー支持体材料の形態であり得、その上に1種以上の香料原料が化学的にまたは物理的に結合し得る。さらにまた、1種以上の香料原料を、マトリクス材料中に溶解または拡散させてもよく、これは該原料(単数)または原料(複数)が発散する速度を制御する役割をする。なおも代替の態様において、1種以上の原料は多孔質基質、例えばシクロデキストリンまたはゼオライトなど、または他の無機材料上に支持され得る。なおさらなる態様において、1種以上の原料は、香料前駆体(pro-perfume)の形態で提供されてもよく、これは好適な環境中で反応して香料原料をコントロールされた様式で放出する。
本発明を説明する役割をする一連の実施例が、ここに後続する。
0.24重量%の以下の香料原料を、76.4%エタノール、10%クエン酸トリエチルおよび3.6%水を含む99.76%の混合物に溶解する;10マイクロリットルのこの溶液を0.4×1.8cm2のエッチングした表面および0.5×2cm2の全体表面を有するエッチングしたガラスプレート上に配置し、4時間、32℃±2℃の温度で蒸発させる。そしてそれぞれのプレートを上述のデバイスに挿入し、前述のフローおよび室内対流条件に供したところ、かかる室内に対する最適な測定条件を20ml/分の空気流れに設定により得た。そして臭気強度をチャネルの出口で少なくとも5人の訓練したパネリストにより測定し、表1に報告する。すべての原料は平均で60秒以内に検知した。特定の原料に対する無臭覚であるとパネリストにより見做された得られたスコアは削除する。
一連の香料の配合物が表2において説明されるように報告されるが、限定的な例ではない。それぞれのグループにおける原料の濃度もまた、表2に報告する。距離をおいた強度を、以下の手順に従って測定した:96%エタノールおよび4%水を含む溶媒(水性アルコール溶液)中の10%香料の溶液の10マイクロリットルを0.4×1.8cm2のエッチングした表面および0.5×2cm2の全体表面を有するエッチングしたガラスプレート上に配置し、32℃±2℃の温度で4時間蒸発させる。そしてそれぞれのプレートを上述のデバイス中に挿入し、前述の流れおよび室内対流条件へ供したところ、かかる室内に関する最適な測定条件を20ml/minでの空気流れの設定により得た。そして臭気強度を、チャネルの出口で(つまり源から2m離れて)、少なくとも5人の訓練したパネリストにより測定し、表2に報告する。7より高い平均強度を有する香料にスコア「+++」を与え;4~7の範囲の平均強度を有する香料にスコア「++」を与え;1~4の範囲の平均強度有する香料にスコア「+」を、および実質的にトレイルなし(つまり、1より低い平均強度)を有する香料にスコア「-」を与えた。
Claims (12)
- 香料組成物の時空的属性を特徴付ける方法であって、以下のステップ:
・香料組成物源が配置される、有向性空気流れを作り出すこと、
・香料組成物を該空気流れに取込み、香り付きプルームを提供し、ここにおいて該組成物は実質的に閉じ込められること;および
・該香り付きプルームをチャネルに沿って該源からの規定距離において該チャネル中の開口部へと向け、その開口部において該香り付きプルームのにおいを嗅ぎ、チャネルに沿った異なる複数の場所で評価することができること、
を含む、前記方法。 - 一定時間の間、香料組成物を蒸散させた後に、評価を実行する、請求項1に記載の方法。
- 評価を0.5メートルよりも長い距離で実行する、請求項1または2に記載の方法。
- 評価手順が、
・ 一定時間T1の間、開放環境中で、20~35℃の温度で香料サンプルを蒸散させること、
・ 32±2℃の温度に維持されたデバイスに、該サンプルを挿入すること、
・ においの嗅覚特徴および強度を、時間の関数として、チャネルの出口で評価すること、および
・ 特定時間T2後、出口から開始して下流へと移動する、チャネルのトップにおける異なる場所において、時間間隔T3内に、においの嗅覚特徴および強度を任意に評価すること
のステップを含む、請求項1~3のいずれか一項に記載の方法。 - 嗅覚属性の評価が、嗅覚強さまたはインパクト、臭気記述、シャープネス、透明性、プレゼンス、および/またはボリュームを含む、請求項1~4のいずれか一項に記載の方法。
- 香料組成物を溶媒中10重量%の濃度で基質に適用する、請求項1~5のいずれか一項に記載の方法。
- 中空体(3)の幅狭部(3b)に収容される長い導管を経由してハウジングから押し出されることができる空気流れを作り出すためのファンを収容する幅広部(3a)を含む中空体(3)からなり;ここで、中空体(3)は、フレグランス組成物のサンプルを好適な支持部に受容するためのスロットまたは開口部(4)を含み;ここで、ハウジングは、導管が空間の全ての向きに向くのを許容する任意にフレキシブルな脚部(6)により、ホルダ(5)に固定され;ここで、使用のとき、ファンが有向性空気流れを作り出し、これはサンプルにわたって通過しそれによりフレグランス組成物を取込み、そして、導管を介して発現され所望でない側方室内対流を抑制するパネル(ABCD)およびパネル(EFGH)によって画定されるチャネル(2)へと発せられるフレグランスプルームを作り出し、ここでチャネルのトップ(ABEF)は解放されて、チャネルに沿った異なる距離におけるフレグランスプルームを評価者が評価することができるようになっている、有向性空気流れを作り出し、発するためのデバイス(1)。
- 空気流れ中の乱流を最小化するために、中空ボディの内径は幅広部から幅狭部にかけて徐々に低減するように、幅広部と幅狭部との間に円錐状部分を含む、請求項7に記載のデバイス(1)。
- ハウジングが、サンプルを加熱するための熱制御された要素を含む、請求項7または8に記載のデバイス(1)。
- パネル(ABCD)およびパネル(EFGH)が平行である、請求項7~9のいずれか一項に記載のデバイス(1)。
- セグメントCDおよびセグメントGHの長さが、少なくとも0.5mである、請求項7~10のいずれか一項に記載のデバイス(1)。
- セグメントCDおよびセグメントGHの長さが、少なくとも1.5mである、請求項11に記載のデバイス(1)。
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EP (2) | EP3521823B1 (ja) |
JP (3) | JP6616330B2 (ja) |
CN (2) | CN111004680A (ja) |
GB (1) | GB201409348D0 (ja) |
MA (1) | MA39814A (ja) |
MX (2) | MX2016013712A (ja) |
WO (1) | WO2015181257A2 (ja) |
Families Citing this family (23)
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GB2515128B (en) * | 2013-06-10 | 2015-05-27 | Givaudan Sa | Improvements in or relating to organic compounds |
EP3218457B1 (en) * | 2014-11-10 | 2019-01-02 | Givaudan S.A. | Improvements in or relating to organic compounds |
GB201421855D0 (en) | 2014-12-09 | 2015-01-21 | Givaudan Sa | Improvements in or relating to organic compounds |
GB201421838D0 (en) | 2014-12-09 | 2015-01-21 | Givaudan Sa | Improvements in or relating to organic compounds |
WO2017100426A1 (en) * | 2015-12-11 | 2017-06-15 | Bedoukian Research, Inc. | Fragrance and flavor compositions containing isomeric alkadienals or isomeric alkadienenitriles |
GB201604290D0 (en) * | 2016-03-14 | 2016-04-27 | Givaudan Sa | Perfume compositions |
CN109219740B (zh) | 2016-03-31 | 2022-09-02 | 西姆莱斯股份公司 | 一种用于评估香味材料香迹的设备 |
CN115058289A (zh) * | 2016-10-14 | 2022-09-16 | 国际香料和香精公司 | 高性能、高冲击强度的香味喷发谐香剂 |
EP3585185B1 (de) | 2017-02-27 | 2024-04-10 | Symrise AG | Verfahren zur herstellung von rotundon-haltigen mischungen |
CN107157292B (zh) * | 2017-05-24 | 2018-10-26 | 方军 | 一种家用盘香及制备方法 |
GB201809528D0 (en) * | 2018-06-11 | 2018-07-25 | Givaudan Sa | Method related to organic compositions |
FR3104720B1 (fr) | 2019-12-16 | 2024-03-15 | Aryballe Tech | Procédé et dispositif pour obtenir la signature olfactive temporelle d’un échantillon et utilisations dudit procédé |
EP3862027A1 (en) | 2020-02-07 | 2021-08-11 | International Flavors & Fragrances Inc. | A portable device and methods for measuring diffusion of fragrances and fragrance raw materials |
US11813926B2 (en) | 2020-08-20 | 2023-11-14 | Denso International America, Inc. | Binding agent and olfaction sensor |
US11636870B2 (en) | 2020-08-20 | 2023-04-25 | Denso International America, Inc. | Smoking cessation systems and methods |
US11760169B2 (en) | 2020-08-20 | 2023-09-19 | Denso International America, Inc. | Particulate control systems and methods for olfaction sensors |
US11932080B2 (en) | 2020-08-20 | 2024-03-19 | Denso International America, Inc. | Diagnostic and recirculation control systems and methods |
US11881093B2 (en) | 2020-08-20 | 2024-01-23 | Denso International America, Inc. | Systems and methods for identifying smoking in vehicles |
US12017506B2 (en) | 2020-08-20 | 2024-06-25 | Denso International America, Inc. | Passenger cabin air control systems and methods |
US11828210B2 (en) | 2020-08-20 | 2023-11-28 | Denso International America, Inc. | Diagnostic systems and methods of vehicles using olfaction |
US11760170B2 (en) | 2020-08-20 | 2023-09-19 | Denso International America, Inc. | Olfaction sensor preservation systems and methods |
US20230253075A1 (en) | 2020-09-30 | 2023-08-10 | Firmenich Sa | Fragrance ingredient spatial recognisability prediction methods and fragrance composition spatial recognisability prediction methods |
WO2023247599A1 (en) * | 2022-06-22 | 2023-12-28 | Firmenich Sa | Fragrance compositions having long-lasting trail performance |
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CH648015A5 (de) * | 1977-03-28 | 1985-02-28 | Givaudan & Cie Sa | Cyclohexenonderivate mit riech- und/oder geschmackstoffeigenschaften. |
DE3242042C1 (de) * | 1982-11-13 | 1983-11-17 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Gemisch von Dimethyl-tricyclo[5.2.1.0?]decan-Derivaten sowie dessen Herstellung und Verwendung als Riech- und Aromastoff |
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2014
- 2014-05-27 GB GBGB1409348.8A patent/GB201409348D0/en not_active Ceased
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2015
- 2015-05-27 MA MA039814A patent/MA39814A/fr unknown
- 2015-05-27 EP EP19165214.8A patent/EP3521823B1/en active Active
- 2015-05-27 US US15/311,366 patent/US20170073614A1/en not_active Abandoned
- 2015-05-27 MX MX2016013712A patent/MX2016013712A/es unknown
- 2015-05-27 EP EP15727605.6A patent/EP3149135A2/en not_active Withdrawn
- 2015-05-27 CN CN201911169372.6A patent/CN111004680A/zh active Pending
- 2015-05-27 CN CN201580029182.8A patent/CN106414689A/zh active Pending
- 2015-05-27 JP JP2016569880A patent/JP6616330B2/ja active Active
- 2015-05-27 WO PCT/EP2015/061756 patent/WO2015181257A2/en active Application Filing
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2016
- 2016-10-19 MX MX2021008754A patent/MX2021008754A/es unknown
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2019
- 2019-07-31 US US16/527,980 patent/US11639484B2/en active Active
- 2019-08-07 JP JP2019145298A patent/JP7303695B2/ja active Active
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2021
- 2021-12-22 JP JP2021208052A patent/JP7246464B2/ja active Active
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2023
- 2023-03-16 US US18/184,995 patent/US20230287297A1/en active Pending
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EP1098195A2 (en) | 1999-11-04 | 2001-05-09 | Givaudan SA | A device for olfactory judgement of an odorous substance, use thereof and a method of operating the device |
WO2007045862A1 (en) | 2005-10-18 | 2007-04-26 | Imperial Chemical Industries Plc | Evaluation of the fragrance characteristics of a substance |
US20120247182A1 (en) | 2011-03-29 | 2012-10-04 | Patti Lynn Nelson | Mobile scent tester |
Also Published As
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JP7246464B2 (ja) | 2023-03-27 |
JP2022071875A (ja) | 2022-05-16 |
WO2015181257A3 (en) | 2016-03-17 |
JP2017519070A (ja) | 2017-07-13 |
MX2021008754A (es) | 2021-08-24 |
EP3149135A2 (en) | 2017-04-05 |
JP2020002363A (ja) | 2020-01-09 |
US11639484B2 (en) | 2023-05-02 |
GB201409348D0 (en) | 2014-07-09 |
US20170073614A1 (en) | 2017-03-16 |
EP3521823A1 (en) | 2019-08-07 |
US20190382684A1 (en) | 2019-12-19 |
US20230287297A1 (en) | 2023-09-14 |
MA39814A (fr) | 2015-12-03 |
CN111004680A (zh) | 2020-04-14 |
MX2016013712A (es) | 2017-01-20 |
CN106414689A (zh) | 2017-02-15 |
EP3521823B1 (en) | 2021-03-03 |
WO2015181257A2 (en) | 2015-12-03 |
JP6616330B2 (ja) | 2019-12-04 |
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