ZA200403708B - Compounds for a controlled release of active molecules - Google Patents
Compounds for a controlled release of active molecules Download PDFInfo
- Publication number
- ZA200403708B ZA200403708B ZA2004/03708A ZA200403708A ZA200403708B ZA 200403708 B ZA200403708 B ZA 200403708B ZA 2004/03708 A ZA2004/03708 A ZA 2004/03708A ZA 200403708 A ZA200403708 A ZA 200403708A ZA 200403708 B ZA200403708 B ZA 200403708B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- formulae
- radical
- formula
- alkenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 238000013270 controlled release Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 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 10
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- -1 alkoxyl radical Chemical class 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 229930195733 hydrocarbon Natural products 0.000 claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 125000000524 functional group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 150000003254 radicals Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 125000004122 cyclic group Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000000412 dendrimer Substances 0.000 claims description 10
- 229920000736 dendritic polymer Polymers 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003599 detergent Substances 0.000 claims description 9
- 239000002304 perfume Substances 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000001408 amides Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 150000002148 esters Chemical group 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 5
- 239000003205 fragrance Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 241000195940 Bryophyta Species 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000002386 air freshener Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000002979 fabric softener Substances 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 238000010409 ironing Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000011929 mousse Nutrition 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000007844 bleaching agent Substances 0.000 claims 1
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000004615 ingredient Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000003578 releasing effect Effects 0.000 description 6
- 239000004753 textile Substances 0.000 description 5
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 238000005406 washing Methods 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
- 238000004140 cleaning Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 239000007858 starting material Substances 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 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- ZNWOKRUGFTXKDK-UHFFFAOYSA-N 4-(2,2,3,6-tetramethylcyclohexyl)but-3-en-2-one Chemical compound CC1CCC(C)C(C)(C)C1C=CC(C)=O ZNWOKRUGFTXKDK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- AZOCECCLWFDTAP-UHFFFAOYSA-N dihydrocarvone Chemical compound CC1CCC(C(C)=C)CC1=O AZOCECCLWFDTAP-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluenecarboxylic acid Natural products CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 229930007850 β-damascenone Natural products 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- 239000001674 (E)-1-(2,6,6-trimethyl-1-cyclohexenyl)but-2-en-1-one Substances 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- IXLLBXDECOMIBP-FNORWQNLSA-N (e)-1-(2,2-dimethyl-6-methylidenecyclohexyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1C(=C)CCCC1(C)C IXLLBXDECOMIBP-FNORWQNLSA-N 0.000 description 1
- 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 1
- RQOYZUVHDKODQU-UHFFFAOYSA-N 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one Chemical compound CCC(=O)CC1=C(C)C=CCC1(C)C RQOYZUVHDKODQU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- XYDMLNRJJZVUKP-UHFFFAOYSA-N 2,5-dimethyl-5-phenylhex-1-en-3-one Chemical compound CC(=C)C(=O)CC(C)(C)C1=CC=CC=C1 XYDMLNRJJZVUKP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QOVYZXTXMWXZGF-UHFFFAOYSA-N 2-methyl-3-octylsulfanyl-5-prop-1-en-2-ylcyclohexan-1-one Chemical compound CCCCCCCCSC1CC(C(C)=C)CC(=O)C1C QOVYZXTXMWXZGF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- LVBXEMGDVWVTGY-SREVYHEPSA-N 2-octenal Chemical compound CCCCC\C=C/C=O LVBXEMGDVWVTGY-SREVYHEPSA-N 0.000 description 1
- VURRTCWBSBCFQT-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfanyl-3-phenylpropanal Chemical compound C1=CC(Cl)=CC=C1SC(CC=O)C1=CC=CC=C1 VURRTCWBSBCFQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WTUPXHZXCUYTPK-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-3-phenylpropanal Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(CC=O)C1=CC=CC=C1 WTUPXHZXCUYTPK-UHFFFAOYSA-N 0.000 description 1
- WXHMGRSZPXGLAH-UHFFFAOYSA-N 3-(benzenesulfonyl)-3-phenylpropanal Chemical compound C=1C=CC=CC=1S(=O)(=O)C(CC=O)C1=CC=CC=C1 WXHMGRSZPXGLAH-UHFFFAOYSA-N 0.000 description 1
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 1
- URQMEZRQHLCJKR-UHFFFAOYSA-N 3-Methyl-5-propyl-2-cyclohexen-1-one Chemical compound CCCC1CC(C)=CC(=O)C1 URQMEZRQHLCJKR-UHFFFAOYSA-N 0.000 description 1
- OMEYLSRTDUEFJK-UHFFFAOYSA-N 3-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]-3-phenylpropanal Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CSC(CC=O)C=2C=CC=CC=2)=C1 OMEYLSRTDUEFJK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RJAOFIXAMOCEMD-UHFFFAOYSA-N 3-phenyl-3-[4-(trifluoromethyl)phenoxy]propanal Chemical compound C1=CC(C(F)(F)F)=CC=C1OC(CC=O)C1=CC=CC=C1 RJAOFIXAMOCEMD-UHFFFAOYSA-N 0.000 description 1
- HVQDFKFQBHEBIM-UHFFFAOYSA-N 3-phenyl-3-phenylmethoxypropanal Chemical compound C=1C=CC=CC=1C(CC=O)OCC1=CC=CC=C1 HVQDFKFQBHEBIM-UHFFFAOYSA-N 0.000 description 1
- OBOPLZQQDLJNFG-UHFFFAOYSA-N 3-phenyl-3-phenylsulfanylpropanal Chemical compound C=1C=CC=CC=1C(CC=O)SC1=CC=CC=C1 OBOPLZQQDLJNFG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
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- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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- 108010021119 Trichosanthin Proteins 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
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- AUIMEUZQOMQCIG-UHFFFAOYSA-N [4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C)CC(=O)C1C(C)=CCCC1(C)C AUIMEUZQOMQCIG-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- CRIGTVCBMUKRSL-UHFFFAOYSA-N alpha-Damascone Natural products CC=CC(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-UHFFFAOYSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- AZOCECCLWFDTAP-RKDXNWHRSA-N dihydrocarvone Natural products C[C@@H]1CC[C@@H](C(C)=C)CC1=O AZOCECCLWFDTAP-RKDXNWHRSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OPCRGEVPIBLWAY-QNRZBPGKSA-N ethyl (2E,4Z)-deca-2,4-dienoate Chemical compound CCCCC\C=C/C=C/C(=O)OCC OPCRGEVPIBLWAY-QNRZBPGKSA-N 0.000 description 1
- AISZSTYLOVXFII-CMDGGOBGSA-N ethyl (e)-oct-2-enoate Chemical compound CCCCC\C=C\C(=O)OCC AISZSTYLOVXFII-CMDGGOBGSA-N 0.000 description 1
- 229940057975 ethyl citrate Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229930007090 gamma-ionone Natural products 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- ZWNPUELCBZVMDA-HJWRWDBZSA-N methyl 2-nonenoate Chemical compound CCCCCC\C=C/C(=O)OC ZWNPUELCBZVMDA-HJWRWDBZSA-N 0.000 description 1
- FZHIDOQMAXDNCC-UHFFFAOYSA-N methyl 5,9-dimethyldeca-2,4,8-trienoate Chemical compound COC(=O)C=CC=C(C)CCC=C(C)C FZHIDOQMAXDNCC-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 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
- 230000001960 triggered effect Effects 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- CRIGTVCBMUKRSL-ALCCZGGFSA-N α-damascone Chemical compound C\C=C/C(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-ALCCZGGFSA-N 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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB0102520 | 2001-12-13 | ||
| PCT/IB2002/005365 WO2003049666A2 (en) | 2001-12-13 | 2002-12-11 | Compounds for a controlled release of active molecules |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403708B true ZA200403708B (en) | 2005-06-29 |
Family
ID=11004233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2004/03708A ZA200403708B (en) | 2001-12-13 | 2004-05-14 | Compounds for a controlled release of active molecules |
Country Status (15)
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|---|---|
| US (2) | US7723286B2 (OSRAM) |
| EP (1) | EP1460994B1 (OSRAM) |
| JP (2) | JP4694785B2 (OSRAM) |
| CN (1) | CN1290485C (OSRAM) |
| AT (1) | ATE409512T1 (OSRAM) |
| AU (1) | AU2002348801B2 (OSRAM) |
| BR (1) | BRPI0214515B1 (OSRAM) |
| CA (1) | CA2468231A1 (OSRAM) |
| DE (1) | DE60229165D1 (OSRAM) |
| ES (1) | ES2312635T3 (OSRAM) |
| MX (1) | MXPA04005512A (OSRAM) |
| PL (1) | PL209377B1 (OSRAM) |
| RU (1) | RU2296118C2 (OSRAM) |
| WO (1) | WO2003049666A2 (OSRAM) |
| ZA (1) | ZA200403708B (OSRAM) |
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| GB0227807D0 (en) * | 2002-11-29 | 2003-01-08 | Givaudan Sa | Improvements in or relating ot organic compounds |
| RU2007117150A (ru) * | 2004-10-08 | 2008-11-20 | Фирмениш Са (Ch) | Амфифильные звездообразные блок-сополимеры |
| JP5065266B2 (ja) * | 2005-07-14 | 2012-10-31 | フイルメニツヒ ソシエテ アノニム | 活性分子の制御された放出のための、両親媒性コポリマー複合体 |
| US20070275866A1 (en) * | 2006-05-23 | 2007-11-29 | Robert Richard Dykstra | Perfume delivery systems for consumer goods |
| ATE501179T1 (de) * | 2006-10-10 | 2011-03-15 | Firmenich & Cie | Polymerkonjugate zur kontrollierten freigabe von aktiven molekülen |
| US7879747B2 (en) * | 2007-03-30 | 2011-02-01 | Kimberly-Clark Worldwide, Inc. | Elastic laminates having fragrance releasing properties and methods of making the same |
| JP2010528161A (ja) * | 2007-06-05 | 2010-08-19 | ザ プロクター アンド ギャンブル カンパニー | 香料システム |
| EP2334626A1 (en) | 2008-09-12 | 2011-06-22 | Firmenich S.A. | Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces |
| US9000052B2 (en) | 2008-10-21 | 2015-04-07 | Firmenich Sa | Perfuming compositions and uses thereof |
| US20100102142A1 (en) * | 2008-10-28 | 2010-04-29 | Daria Tagliareni | Scent dispenser assembly |
| CA2744033A1 (en) | 2008-12-01 | 2010-06-10 | The Procter & Gamble Company | Perfume systems |
| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| BRPI1016076B1 (pt) | 2009-06-19 | 2017-05-16 | Firmenich & Cie | composições antiodor e método de uso para neutralizar o mau cheiro do suor |
| EP2270124A1 (en) | 2009-06-30 | 2011-01-05 | The Procter & Gamble Company | Bleaching compositions comprising a perfume delivery system |
| CN102652175B (zh) | 2009-12-09 | 2016-02-10 | 宝洁公司 | 织物和家居护理产品 |
| KR101463727B1 (ko) | 2009-12-17 | 2014-11-21 | 더 프록터 앤드 갬블 캄파니 | 악취 결합 중합체 및 악취 제어 성분을 포함하는 청향 조성물 |
| EP2579839B1 (en) | 2010-06-10 | 2016-01-13 | Firmenich SA | Perfuming compositions and uses thereof |
| JP5868966B2 (ja) | 2010-06-22 | 2016-02-24 | ザ プロクター アンド ギャンブルカンパニー | 香料系 |
| PL2585569T3 (pl) | 2010-06-22 | 2017-03-31 | The Procter And Gamble Company | Systemy zapachowe |
| RU2555042C2 (ru) | 2010-07-02 | 2015-07-10 | Дзе Проктер Энд Гэмбл Компани | Способ доставки активнодействующего вещества |
| 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 |
| JP5770280B2 (ja) | 2010-07-02 | 2015-08-26 | ザ プロクター アンド ギャンブルカンパニー | 非香料系活性剤を含むフィラメントの不織布ウェブ及びその作製方法 |
| PL2588288T3 (pl) | 2010-07-02 | 2016-04-29 | Procter & Gamble | Proces wytwarzania powłok z siatek włókninowych |
| WO2012003319A2 (en) | 2010-07-02 | 2012-01-05 | The Procter & Gamble Company | Filaments comprising an active agent nonwoven webs and methods for making same |
| CN103370296B (zh) * | 2011-02-17 | 2015-08-05 | 弗门尼舍有限公司 | 白松香族的加香成分 |
| CN103380206A (zh) * | 2011-02-21 | 2013-10-30 | 弗门尼舍有限公司 | 含有前香料的消费品 |
| US8912350B2 (en) | 2011-06-23 | 2014-12-16 | The Procter & Gamble Company | Perfume systems |
| EP2725912A4 (en) | 2011-06-29 | 2015-03-04 | Solae Llc | BAKERY COMPOSITIONS WITH SOYAMOL PROTEINS ISOLATED FROM PROCESSING STREAMS |
| JP5253608B2 (ja) * | 2011-07-26 | 2013-07-31 | 花王株式会社 | 香料放出剤 |
| ES2592286T3 (es) * | 2011-10-06 | 2016-11-29 | Firmenich Sa | Látex fotolábil para la liberación de perfumes |
| PL2771071T3 (pl) | 2011-10-27 | 2020-02-28 | Firmenich Sa | Kompozycje perfumeryjne i ich zastosowanie |
| MX341723B (es) | 2011-11-04 | 2016-08-31 | Firmenich & Cie | Composiciones perfumantes y usos de las mismas. |
| FR2985272B1 (fr) | 2012-01-04 | 2021-10-22 | Procter & Gamble | Structures fibreuses contenant des actifs et ayant des regions multiples aux caracteristiques distinctes |
| FR2985273B1 (fr) | 2012-01-04 | 2021-09-24 | Procter & Gamble | Structures fibreuses contenant des actifs et ayant des regions multiples |
| RU2016140896A (ru) | 2012-01-04 | 2018-12-14 | Дзе Проктер Энд Гэмбл Компани | Волокнистые структуры, содержащие частицы, и способы их изготовления |
| MX349739B (es) * | 2012-03-20 | 2017-08-10 | Firmenich & Cie | Compuestos para una liberacion controlada de moleculas perfumantes activas. |
| US20140323383A1 (en) * | 2013-04-26 | 2014-10-30 | The Procter & Gamble Company | Pouch comprising a liquid detergent composition |
| WO2014202591A1 (en) * | 2013-06-19 | 2014-12-24 | Firmenich Sa | Polysiloxane conjugates as fragrance delivery systems |
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| CN105518116B (zh) * | 2013-09-09 | 2019-12-10 | 弗门尼舍有限公司 | 用作活性分子受控释放用的前体的硫醚衍生物 |
| EP3572572B1 (en) | 2013-12-09 | 2021-01-20 | The Procter & Gamble Company | Method for printing a graphic on a fibrous structure |
| CN105829514B (zh) * | 2013-12-19 | 2020-12-22 | 花王株式会社 | 赋香方法 |
| US20150217015A1 (en) * | 2014-02-04 | 2015-08-06 | The Procter & Gamble Company | Long lasting freshening compositions |
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| US10323127B2 (en) | 2015-02-17 | 2019-06-18 | Firmenich Sa | Poly(aspartic acid) derived co-polymers for a controlled release of perfuming ingredients |
| JP6671384B2 (ja) * | 2015-02-25 | 2020-03-25 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 相乗作用を有する付香組成物 |
| JP6793737B2 (ja) * | 2015-10-19 | 2020-12-02 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | ペルオキシヘミアセタールプロフレグラントおよびプロフレーバー化合物 |
| 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 |
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| US4149020A (en) * | 1978-04-05 | 1979-04-10 | International Flavors & Fragrances Inc. | Intermediate for preparation of 2,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol |
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| JPS57197262A (en) * | 1981-05-29 | 1982-12-03 | Res Dev Corp Of Japan | Production of optically active beta-arylthio or alkylthioketone |
| DE3228289A1 (de) | 1982-07-29 | 1984-02-09 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | 1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl- cyclohexene und deren verwendung als riech- und aromastoff |
| DE3307869A1 (de) | 1983-03-05 | 1984-09-06 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Methylsubstituierte 1-((3-methylthio)-1-oxo-butyl)-cyclohex-2-ene, verfahren zu deren herstellung und deren verwendung als riech- und aromastoffe |
| JPS61225138A (ja) * | 1985-03-29 | 1986-10-06 | Daicel Chem Ind Ltd | 多重結合を含む原子団を持つアルコ−ルの光学分割方法 |
| SU1698276A1 (ru) * | 1988-07-20 | 1991-12-15 | Научно-производственное объединение по эфиромасличным культурам и маслам "Эфирмасло" | Способ получени ароматического продукта с запахом розы |
| US5143900A (en) * | 1989-05-19 | 1992-09-01 | Colgate-Palmolive Company | Perfumes containing N-lower alkyl neoalkanamide (s) |
| US5158941A (en) * | 1990-06-08 | 1992-10-27 | E. I. Du Pont De Nemours And Company | Lipid A analog as stimulant for production of interleukin-1 in human monocytes and tumor cell growth inhibitor |
| JP2981621B2 (ja) * | 1990-11-30 | 1999-11-22 | イハラケミカル工業株式会社 | ビフェニルビスホスフィン錯体 |
| US5531910A (en) * | 1995-07-07 | 1996-07-02 | The Procter & Gamble Company | Biodegradable fabric softener compositions with improved perfume longevity |
| RU2113133C1 (ru) * | 1995-12-01 | 1998-06-20 | Всероссийский научно-исследовательский институт пищевых ароматизаторов, кислот и красителей | Пищевой ароматизатор со вкусом и ароматом тропических плодов |
| WO1997024308A1 (fr) * | 1995-12-29 | 1997-07-10 | Nippon Zeon Co., Ltd. | Procede de preparation de composes carbonyle |
| US5919752A (en) * | 1997-04-24 | 1999-07-06 | Procter & Gamble | Perfumes having odor longevity benefits |
| EP0955290B1 (en) * | 1998-05-08 | 2003-03-19 | Firmenich Sa | Unsaturated ketones and their use in perfumery |
| JP4469441B2 (ja) * | 1999-02-10 | 2010-05-26 | 明治乳業株式会社 | 神経変性疾患の予防又は治療薬 |
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| ATE384043T1 (de) * | 2001-12-05 | 2008-02-15 | Firmenich & Cie | Ungesättigter ester als riechstoffkomponente |
-
2002
- 2002-12-11 BR BRPI0214515A patent/BRPI0214515B1/pt active IP Right Grant
- 2002-12-11 CA CA002468231A patent/CA2468231A1/en not_active Abandoned
- 2002-12-11 ES ES02781640T patent/ES2312635T3/es not_active Expired - Lifetime
- 2002-12-11 RU RU2004121218/04A patent/RU2296118C2/ru not_active IP Right Cessation
- 2002-12-11 AU AU2002348801A patent/AU2002348801B2/en not_active Ceased
- 2002-12-11 CN CNB028248716A patent/CN1290485C/zh not_active Expired - Lifetime
- 2002-12-11 AT AT02781640T patent/ATE409512T1/de not_active IP Right Cessation
- 2002-12-11 PL PL371541A patent/PL209377B1/pl unknown
- 2002-12-11 MX MXPA04005512A patent/MXPA04005512A/es active IP Right Grant
- 2002-12-11 WO PCT/IB2002/005365 patent/WO2003049666A2/en not_active Ceased
- 2002-12-11 JP JP2003550717A patent/JP4694785B2/ja not_active Expired - Lifetime
- 2002-12-11 EP EP02781640A patent/EP1460994B1/en not_active Expired - Lifetime
- 2002-12-11 DE DE60229165T patent/DE60229165D1/de not_active Expired - Lifetime
-
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 |
|---|---|
| PL209377B1 (pl) | 2011-08-31 |
| RU2296118C2 (ru) | 2007-03-27 |
| JP2005511710A (ja) | 2005-04-28 |
| MXPA04005512A (es) | 2004-12-06 |
| CN1602184A (zh) | 2005-03-30 |
| BRPI0214515B1 (pt) | 2016-03-22 |
| PL371541A1 (en) | 2005-06-27 |
| JP5409457B2 (ja) | 2014-02-05 |
| US7935669B2 (en) | 2011-05-03 |
| RU2004121218A (ru) | 2006-01-10 |
| ATE409512T1 (de) | 2008-10-15 |
| JP2010215910A (ja) | 2010-09-30 |
| WO2003049666A3 (en) | 2004-07-15 |
| DE60229165D1 (de) | 2008-11-13 |
| CN1290485C (zh) | 2006-12-20 |
| WO2003049666A2 (en) | 2003-06-19 |
| AU2002348801A1 (en) | 2003-06-23 |
| CA2468231A1 (en) | 2003-06-19 |
| EP1460994A2 (en) | 2004-09-29 |
| JP4694785B2 (ja) | 2011-06-08 |
| EP1460994B1 (en) | 2008-10-01 |
| ES2312635T3 (es) | 2009-03-01 |
| AU2002348801B2 (en) | 2007-11-22 |
| BR0214515A (pt) | 2004-11-30 |
| US20090181878A1 (en) | 2009-07-16 |
| US7723286B2 (en) | 2010-05-25 |
| US20040220074A1 (en) | 2004-11-04 |
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