PL209377B1 - Kompozycja zapachowa lub wyrób perfumowany, sposób poprawiania, zwiększania lub modyfikowania zapachu kompozycji zapachowej lub wyrobu perfumowanego, sposób perfumowania powierzchni, sposób intensyfikowania lub przedłużania efektu dyfundowania składnika zapachowego na powierzchni, oraz związek stanowiący składnik czynny - Google Patents
Kompozycja zapachowa lub wyrób perfumowany, sposób poprawiania, zwiększania lub modyfikowania zapachu kompozycji zapachowej lub wyrobu perfumowanego, sposób perfumowania powierzchni, sposób intensyfikowania lub przedłużania efektu dyfundowania składnika zapachowego na powierzchni, oraz związek stanowiący składnik czynnyInfo
- Publication number
- PL209377B1 PL209377B1 PL371541A PL37154102A PL209377B1 PL 209377 B1 PL209377 B1 PL 209377B1 PL 371541 A PL371541 A PL 371541A PL 37154102 A PL37154102 A PL 37154102A PL 209377 B1 PL209377 B1 PL 209377B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- alkyl
- formula
- radical
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 110
- 238000013270 controlled release Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 150000002576 ketones Chemical class 0.000 claims abstract description 18
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 11
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 9
- -1 alkylbenzene radical Chemical class 0.000 claims description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 49
- 239000003205 fragrance Substances 0.000 claims description 46
- 239000002304 perfume Substances 0.000 claims description 37
- 229930195733 hydrocarbon Natural products 0.000 claims description 30
- 239000004215 Carbon black (E152) Substances 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000524 functional group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 239000004615 ingredient Substances 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 229910001868 water Inorganic materials 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 20
- 239000003599 detergent Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 15
- 239000004744 fabric Substances 0.000 claims description 13
- 239000012634 fragment Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000002979 fabric softener Substances 0.000 claims description 11
- 239000000412 dendrimer Substances 0.000 claims description 10
- 229920000736 dendritic polymer Polymers 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- AZOCECCLWFDTAP-UHFFFAOYSA-N dihydrocarvone Chemical compound CC1CCC(C(C)=C)CC1=O AZOCECCLWFDTAP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000012437 perfumed product Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002781 deodorant agent Substances 0.000 claims description 4
- 238000009792 diffusion process Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- LCILCECYONZKIG-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)sulfonyl-5-prop-1-en-2-ylcyclohexan-1-one Chemical compound C1C(C(C)=C)CC(=O)C(C)C1S(=O)(=O)C1=CC=C(C)C=C1 LCILCECYONZKIG-UHFFFAOYSA-N 0.000 claims description 3
- XSZKSUQRFPKLEA-UHFFFAOYSA-N 2-methyl-3-phenylmethoxy-5-prop-1-en-2-ylcyclohexan-1-one Chemical compound C1C(C(C)=C)CC(=O)C(C)C1OCC1=CC=CC=C1 XSZKSUQRFPKLEA-UHFFFAOYSA-N 0.000 claims description 3
- QREMKDNTSICFFJ-UHFFFAOYSA-N 2-methyl-3-phenylsulfanyl-5-prop-1-en-2-ylcyclohexan-1-one Chemical compound C1C(C(C)=C)CC(=O)C(C)C1SC1=CC=CC=C1 QREMKDNTSICFFJ-UHFFFAOYSA-N 0.000 claims description 3
- LXIPHPSWQDTYFU-UHFFFAOYSA-N 3-phenylmethoxy-1-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-1-one Chemical compound C=1C=CC=CC=1COC(C)CC(=O)C1C(C)=CCCC1(C)C LXIPHPSWQDTYFU-UHFFFAOYSA-N 0.000 claims description 3
- QIBCUJOKPMCQMF-UHFFFAOYSA-N 4-(benzenesulfonyl)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one Chemical compound C=1C=CC=CC=1S(=O)(=O)C(CC(=O)C)C1=C(C)C=CCC1(C)C QIBCUJOKPMCQMF-UHFFFAOYSA-N 0.000 claims description 3
- MUEPAPFBHYNUTI-UHFFFAOYSA-N 4-phenylsulfanyl-4-(2,6,6-trimethylcyclohexen-1-yl)butan-2-one Chemical compound CC=1CCCC(C)(C)C=1C(CC(=O)C)SC1=CC=CC=C1 MUEPAPFBHYNUTI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002386 air freshener Substances 0.000 claims description 3
- 230000001166 anti-perspirative effect Effects 0.000 claims description 3
- 239000003213 antiperspirant Substances 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- AZOCECCLWFDTAP-RKDXNWHRSA-N dihydrocarvone Natural products C[C@@H]1CC[C@@H](C(C)=C)CC1=O AZOCECCLWFDTAP-RKDXNWHRSA-N 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 238000010409 ironing Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- GXECIHVDIUTCQE-UHFFFAOYSA-N methyl 3-phenylmethoxydecanoate Chemical compound CCCCCCCC(CC(=O)OC)OCC1=CC=CC=C1 GXECIHVDIUTCQE-UHFFFAOYSA-N 0.000 claims description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000344 soap Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 claims description 2
- RLUIEXWYIHRHNU-UHFFFAOYSA-N 3-(4-methylphenyl)sulfanyl-3-phenylpropanal Chemical compound C1=CC(C)=CC=C1SC(CC=O)C1=CC=CC=C1 RLUIEXWYIHRHNU-UHFFFAOYSA-N 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920006317 cationic polymer Polymers 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229940097362 cyclodextrins Drugs 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- BPBBQTYLVZYVEN-UHFFFAOYSA-N methyl 3-(benzenesulfonyl)-5,9-dimethyldec-8-enoate Chemical compound CC(C)=CCCC(C)CC(CC(=O)OC)S(=O)(=O)C1=CC=CC=C1 BPBBQTYLVZYVEN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 229910052681 coesite Inorganic materials 0.000 description 12
- 229910052906 cristobalite Inorganic materials 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 235000012239 silicon dioxide Nutrition 0.000 description 12
- 229910052682 stishovite Inorganic materials 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 229910052905 tridymite Inorganic materials 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000007832 Na2SO4 Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- UECRYUKOKFMTKM-UHFFFAOYSA-N 3-hydroxy-1-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-1-one Chemical compound CC(O)CC(=O)C1C(C)=CCCC1(C)C UECRYUKOKFMTKM-UHFFFAOYSA-N 0.000 description 5
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 5
- BUOUXMBGDVNFBU-UHFFFAOYSA-N [4-oxo-4-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl] 4-ethenylbenzoate Chemical compound C=1C=C(C=C)C=CC=1C(=O)OC(C)CC(=O)C1C(C)C=CCC1(C)C BUOUXMBGDVNFBU-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
- SSRRGIDSLCEXLZ-UHFFFAOYSA-N 3-hydroxy-1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one Chemical compound CC(O)CC(=O)C1C(C)C=CCC1(C)C SSRRGIDSLCEXLZ-UHFFFAOYSA-N 0.000 description 4
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- LLWGDNREPDWSRL-ACCUITESSA-N (2e)-cyclopentadec-2-en-1-one Chemical compound O=C/1CCCCCCCCCCCC\C=C\1 LLWGDNREPDWSRL-ACCUITESSA-N 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
- VZVOPRMLJKLOFD-UHFFFAOYSA-N 1-(2,2,3,6-tetramethylcyclohexyl)but-2-en-1-one Chemical compound CC=CC(=O)C1C(C)CCC(C)C1(C)C VZVOPRMLJKLOFD-UHFFFAOYSA-N 0.000 description 3
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 3
- LNTJADZLGCWBQH-UHFFFAOYSA-N 3-dodecylsulfanyl-1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one Chemical compound CCCCCCCCCCCCSC(C)CC(=O)C1C(C)C=CCC1(C)C LNTJADZLGCWBQH-UHFFFAOYSA-N 0.000 description 3
- BGTBFNDXYDYBEY-FNORWQNLSA-N 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one Chemical compound C\C=C\C(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-FNORWQNLSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 3
- POIARNZEYGURDG-UHFFFAOYSA-N beta-damascenone Natural products CC=CC(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- DIESVMYDBWZXGJ-UHFFFAOYSA-N (3-oxocyclopentadecyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCCCCCCCCCCC(=O)C1 DIESVMYDBWZXGJ-UHFFFAOYSA-N 0.000 description 2
- 239000001674 (E)-1-(2,6,6-trimethyl-1-cyclohexenyl)but-2-en-1-one Substances 0.000 description 2
- XEJGJTYRUWUFFD-FNORWQNLSA-N (e)-1-(2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1C(C)C=CCC1(C)C XEJGJTYRUWUFFD-FNORWQNLSA-N 0.000 description 2
- BGTBFNDXYDYBEY-UHFFFAOYSA-N 1-(2,6,6-trimethylcyclohexen-1-yl)but-2-en-1-one Chemical compound CC=CC(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-UHFFFAOYSA-N 0.000 description 2
- CAISRLWPMZHBTO-UHFFFAOYSA-N 1-(2-hydroxy-5,5-dimethylcyclohexyl)pent-4-en-1-one Chemical compound CC1(C)CCC(O)C(C(=O)CCC=C)C1 CAISRLWPMZHBTO-UHFFFAOYSA-N 0.000 description 2
- OEVIJAZJVZDBQL-UHFFFAOYSA-N 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one Chemical compound CC1(C)CCC=C(C(=O)CCC=C)C1 OEVIJAZJVZDBQL-UHFFFAOYSA-N 0.000 description 2
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- NTZXNXPNHSIYCM-UHFFFAOYSA-N propyl 4-ethenylbenzoate Chemical compound CCCOC(=O)C1=CC=C(C=C)C=C1 NTZXNXPNHSIYCM-UHFFFAOYSA-N 0.000 description 1
- WSIZDNPFIBZART-UHFFFAOYSA-N propyl undec-10-enoate Chemical compound CCCOC(=O)CCCCCCCCC=C WSIZDNPFIBZART-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
- SFEOKXHPFMOVRM-BQYQJAHWSA-N γ-ionone Chemical compound CC(=O)\C=C\C1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-BQYQJAHWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB0102520 | 2001-12-13 |
Publications (2)
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|---|---|
| PL371541A1 PL371541A1 (en) | 2005-06-27 |
| PL209377B1 true PL209377B1 (pl) | 2011-08-31 |
Family
ID=11004233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL371541A PL209377B1 (pl) | 2001-12-13 | 2002-12-11 | Kompozycja zapachowa lub wyrób perfumowany, sposób poprawiania, zwiększania lub modyfikowania zapachu kompozycji zapachowej lub wyrobu perfumowanego, sposób perfumowania powierzchni, sposób intensyfikowania lub przedłużania efektu dyfundowania składnika zapachowego na powierzchni, oraz związek stanowiący składnik czynny |
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| US (2) | US7723286B2 (enExample) |
| EP (1) | EP1460994B1 (enExample) |
| JP (2) | JP4694785B2 (enExample) |
| CN (1) | CN1290485C (enExample) |
| AT (1) | ATE409512T1 (enExample) |
| AU (1) | AU2002348801B2 (enExample) |
| BR (1) | BRPI0214515B1 (enExample) |
| CA (1) | CA2468231A1 (enExample) |
| DE (1) | DE60229165D1 (enExample) |
| ES (1) | ES2312635T3 (enExample) |
| MX (1) | MXPA04005512A (enExample) |
| PL (1) | PL209377B1 (enExample) |
| RU (1) | RU2296118C2 (enExample) |
| WO (1) | WO2003049666A2 (enExample) |
| ZA (1) | ZA200403708B (enExample) |
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| GB0227807D0 (en) * | 2002-11-29 | 2003-01-08 | Givaudan Sa | Improvements in or relating ot organic compounds |
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| WO2007007216A2 (en) * | 2005-07-14 | 2007-01-18 | Firmenich Sa | Amphiphilic co-polymer conjugates for a controlled release of active molecules |
| US20070275866A1 (en) * | 2006-05-23 | 2007-11-29 | Robert Richard Dykstra | Perfume delivery systems for consumer goods |
| MX2009003539A (es) * | 2006-10-10 | 2009-04-15 | Firmenich & Cie | Conjugados de polimero para una liberacion controlada de moleculas activas. |
| US7879747B2 (en) * | 2007-03-30 | 2011-02-01 | Kimberly-Clark Worldwide, Inc. | Elastic laminates having fragrance releasing properties and methods of making the same |
| ES2399942T3 (es) * | 2007-06-05 | 2013-04-04 | The Procter & Gamble Company | Sistemas de perfume |
| CN102149664B (zh) | 2008-09-12 | 2014-04-23 | 弗门尼舍有限公司 | 能释放活性醛和活性酮的二乙烯基醚衍生物及用于给表面加香的方法 |
| EP2349196B1 (en) | 2008-10-21 | 2018-04-25 | Firmenich S.A. | Perfuming compositions and uses thereof |
| US20100102142A1 (en) * | 2008-10-28 | 2010-04-29 | Daria Tagliareni | Scent dispenser assembly |
| CN102300550B (zh) | 2008-12-01 | 2014-04-23 | 宝洁公司 | 香料体系 |
| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| WO2010146556A2 (en) | 2009-06-19 | 2010-12-23 | Firmenich Sa | Malodor counteracting compositions and method for their use to counteract sweat malodor |
| EP2270124A1 (en) | 2009-06-30 | 2011-01-05 | The Procter & Gamble Company | Bleaching compositions comprising a perfume delivery system |
| EP4159833A3 (en) | 2009-12-09 | 2023-07-26 | The Procter & Gamble Company | Fabric and home care products |
| EP2512527A1 (en) | 2009-12-17 | 2012-10-24 | The Procter & Gamble Company | Freshening compositions comprising malodor binding polymers and malodor control components |
| JP5911480B2 (ja) | 2010-06-10 | 2016-04-27 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 香料組成物及びそれらの使用 |
| HUE032069T2 (en) | 2010-06-22 | 2017-10-30 | Procter & Gamble | Fragrance systems |
| EP2585568A1 (en) | 2010-06-22 | 2013-05-01 | The Procter and Gamble Company | Perfume systems |
| CN102971126B (zh) | 2010-07-02 | 2016-03-23 | 宝洁公司 | 由非织造纤维网制备膜的方法 |
| EP2588653B1 (en) | 2010-07-02 | 2018-06-20 | The Procter and Gamble Company | Method of treating a fabric article |
| BR112013000044B1 (pt) | 2010-07-02 | 2022-01-04 | The Procter & Gamble Company | Método para a distribuição de agentes ativos a artigos de tecido ou superfícies duras |
| CN103003476B (zh) | 2010-07-02 | 2016-02-10 | 宝洁公司 | 纤维网材料以及用于制造纤维网材料的方法 |
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| MX354501B (es) * | 2011-02-17 | 2018-03-08 | Firmenich & Cie | Ingrediente perfumante de la familia galbano. |
| WO2012113746A1 (en) | 2011-02-21 | 2012-08-30 | Firmenich Sa | Consumer products containing pro-fragrances |
| WO2012177357A1 (en) | 2011-06-23 | 2012-12-27 | The Procter & Gamble Company | Perfume systems |
| WO2013002786A1 (en) | 2011-06-29 | 2013-01-03 | Solae | Baked food compositions comprising soy whey proteins that have been isolated from processing streams |
| JP5253608B2 (ja) * | 2011-07-26 | 2013-07-31 | 花王株式会社 | 香料放出剤 |
| US9315763B2 (en) * | 2011-10-06 | 2016-04-19 | Firmenich Sa | Photolabile latex for the release of perfumes |
| WO2013060691A2 (en) | 2011-10-27 | 2013-05-02 | Firmenich Sa | Perfuming compositions and uses thereof |
| RU2605538C2 (ru) | 2011-11-04 | 2016-12-20 | Фирмениш Са | Парфюмерные композиции и их применение |
| EP2800802B1 (en) | 2012-01-04 | 2018-02-28 | The Procter and Gamble Company | Active containing fibrous structures with multiple regions having differing densities |
| RU2655288C1 (ru) | 2012-01-04 | 2018-05-24 | Дзе Проктер Энд Гэмбл Компани | Волокнистые структуры, содержащие частицы, и способы их изготовления |
| MX342355B (es) | 2012-01-04 | 2016-09-23 | Procter & Gamble | Estructuras fibrosas que contienen activos con multiples regiones. |
| US11155772B2 (en) | 2012-03-20 | 2021-10-26 | Firmenich Sa | Compounds for a controlled release of active perfuming molecules |
| US20140323383A1 (en) * | 2013-04-26 | 2014-10-30 | The Procter & Gamble Company | Pouch comprising a liquid detergent composition |
| EP3010960A1 (en) * | 2013-06-19 | 2016-04-27 | Firmenich SA | Polysiloxane conjugates as fragrance delivery systems |
| EP3024427B1 (en) | 2013-07-22 | 2019-10-09 | Takasago International Corporation | Derivatives of 2,2,6-trimethylcyclohexane-carboxylate |
| WO2015032885A1 (en) | 2013-09-09 | 2015-03-12 | Firmenich Sa | Thioether derivatives as precursors for a controlled release of active molecules |
| EP4253649B1 (en) | 2013-12-09 | 2025-04-23 | The Procter & Gamble Company | Fibrous structures including an active agent and having a graphic printed thereon |
| EP3085758B1 (en) * | 2013-12-19 | 2018-06-06 | Kao Corporation | Perfuming method |
| US20150217015A1 (en) * | 2014-02-04 | 2015-08-06 | The Procter & Gamble Company | Long lasting freshening compositions |
| BR112017011110A2 (pt) * | 2014-12-10 | 2018-01-23 | Firmenich & Cie | polissiloxanos como sistemas de distribuição de fragrância em perfumaria fina |
| WO2016131694A1 (en) * | 2015-02-17 | 2016-08-25 | Firmenich Sa | Poly(aspartic acid) derived co-polymers for a controlled release of perfuming ingredients |
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| US11155518B2 (en) * | 2015-10-19 | 2021-10-26 | Firmenich Sa | Peroxyhemiacetal profragrant and proflavor compounds |
| US9796948B2 (en) * | 2016-01-13 | 2017-10-24 | The Procter & Gamble Company | Laundry detergent compositions comprising renewable components |
| JP6643160B2 (ja) * | 2016-03-24 | 2020-02-12 | ライオン株式会社 | 液体柔軟剤組成物 |
| US10632221B2 (en) * | 2016-03-28 | 2020-04-28 | The Procter & Gamble Company | Long lasting and stable freshening compositions and methods of freshening the air |
| US12016943B2 (en) | 2016-08-25 | 2024-06-25 | Firmenich Sa | Antiperspirant or deodorant composition |
| GB2604760B (en) | 2017-01-27 | 2022-11-30 | Procter & Gamble | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
| US11697906B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles and product-shipping assemblies for containing the same |
| US11697904B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
| US11697905B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
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| ATE223475T1 (de) * | 1999-08-18 | 2002-09-15 | Givaudan Sa | Weichmittelzusammensetzung |
| JP4071421B2 (ja) * | 2000-06-07 | 2008-04-02 | 高砂香料工業株式会社 | シクロヘキセニルメチルケトンの製造法 |
| ES2298319T3 (es) * | 2001-12-05 | 2008-05-16 | Firmenich Sa | Ester insaturado como ingrediente perfumante. |
-
2002
- 2002-12-11 CA CA002468231A patent/CA2468231A1/en not_active Abandoned
- 2002-12-11 PL PL371541A patent/PL209377B1/pl unknown
- 2002-12-11 RU RU2004121218/04A patent/RU2296118C2/ru not_active IP Right Cessation
- 2002-12-11 DE DE60229165T patent/DE60229165D1/de not_active Expired - Lifetime
- 2002-12-11 AT AT02781640T patent/ATE409512T1/de not_active IP Right Cessation
- 2002-12-11 AU AU2002348801A patent/AU2002348801B2/en not_active Ceased
- 2002-12-11 EP EP02781640A patent/EP1460994B1/en not_active Expired - Lifetime
- 2002-12-11 CN CNB028248716A patent/CN1290485C/zh not_active Expired - Lifetime
- 2002-12-11 WO PCT/IB2002/005365 patent/WO2003049666A2/en not_active Ceased
- 2002-12-11 ES ES02781640T patent/ES2312635T3/es not_active Expired - Lifetime
- 2002-12-11 JP JP2003550717A patent/JP4694785B2/ja not_active Expired - Lifetime
- 2002-12-11 MX MXPA04005512A patent/MXPA04005512A/es active IP Right Grant
- 2002-12-11 BR BRPI0214515A patent/BRPI0214515B1/pt active IP Right Grant
-
2004
- 2004-05-14 ZA ZA2004/03708A patent/ZA200403708B/en unknown
- 2004-05-25 US US10/852,754 patent/US7723286B2/en active Active
-
2009
- 2009-02-25 US US12/392,909 patent/US7935669B2/en not_active Expired - Lifetime
-
2010
- 2010-03-17 JP JP2010060925A patent/JP5409457B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1290485C (zh) | 2006-12-20 |
| WO2003049666A3 (en) | 2004-07-15 |
| RU2004121218A (ru) | 2006-01-10 |
| US7935669B2 (en) | 2011-05-03 |
| JP2005511710A (ja) | 2005-04-28 |
| EP1460994B1 (en) | 2008-10-01 |
| AU2002348801B2 (en) | 2007-11-22 |
| BR0214515A (pt) | 2004-11-30 |
| JP5409457B2 (ja) | 2014-02-05 |
| ATE409512T1 (de) | 2008-10-15 |
| US20090181878A1 (en) | 2009-07-16 |
| CA2468231A1 (en) | 2003-06-19 |
| ZA200403708B (en) | 2005-06-29 |
| BRPI0214515B1 (pt) | 2016-03-22 |
| JP2010215910A (ja) | 2010-09-30 |
| US7723286B2 (en) | 2010-05-25 |
| ES2312635T3 (es) | 2009-03-01 |
| US20040220074A1 (en) | 2004-11-04 |
| EP1460994A2 (en) | 2004-09-29 |
| MXPA04005512A (es) | 2004-12-06 |
| PL371541A1 (en) | 2005-06-27 |
| JP4694785B2 (ja) | 2011-06-08 |
| WO2003049666A2 (en) | 2003-06-19 |
| DE60229165D1 (de) | 2008-11-13 |
| CN1602184A (zh) | 2005-03-30 |
| RU2296118C2 (ru) | 2007-03-27 |
| AU2002348801A1 (en) | 2003-06-23 |
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