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)
| Country | Link |
|---|---|
| US (2) | US7723286B2 (https=) |
| EP (1) | EP1460994B1 (https=) |
| JP (2) | JP4694785B2 (https=) |
| CN (1) | CN1290485C (https=) |
| AT (1) | ATE409512T1 (https=) |
| AU (1) | AU2002348801B2 (https=) |
| BR (1) | BRPI0214515B1 (https=) |
| CA (1) | CA2468231A1 (https=) |
| DE (1) | DE60229165D1 (https=) |
| ES (1) | ES2312635T3 (https=) |
| MX (1) | MXPA04005512A (https=) |
| PL (1) | PL209377B1 (https=) |
| RU (1) | RU2296118C2 (https=) |
| WO (1) | WO2003049666A2 (https=) |
| ZA (1) | ZA200403708B (https=) |
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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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| EP1904541B1 (en) * | 2005-07-14 | 2016-03-16 | 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 |
| US8022030B2 (en) | 2006-10-10 | 2011-09-20 | Firmenich Sa | Polymer conjugates for a controlled release of active molecules |
| US7879747B2 (en) * | 2007-03-30 | 2011-02-01 | Kimberly-Clark Worldwide, Inc. | Elastic laminates having fragrance releasing properties and methods of making the same |
| US20080305977A1 (en) * | 2007-06-05 | 2008-12-11 | The Procter & Gamble Company | Perfume systems |
| WO2010029462A1 (en) | 2008-09-12 | 2010-03-18 | Firmenich Sa | Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces |
| CN102170858A (zh) | 2008-10-21 | 2011-08-31 | 弗门尼舍有限公司 | 加香组合物及其应用 |
| US20100102142A1 (en) * | 2008-10-28 | 2010-04-29 | Daria Tagliareni | Scent dispenser assembly |
| BRPI0922770A2 (pt) | 2008-12-01 | 2019-09-24 | Procter & Gamble | sistemas de perfume |
| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| ES2767877T3 (es) | 2009-06-19 | 2020-06-18 | Firmenich & Cie | Composiciones para contrarrestar el mal olor y procedimiento para su uso para contrarrestar el mal olor del sudor |
| EP2270124A1 (en) | 2009-06-30 | 2011-01-05 | The Procter & Gamble Company | Bleaching compositions comprising a perfume delivery system |
| MX2012006616A (es) | 2009-12-09 | 2012-06-21 | Procter & Gamble | Productos para el cuidado de las telas y el hogar. |
| KR101463727B1 (ko) | 2009-12-17 | 2014-11-21 | 더 프록터 앤드 갬블 캄파니 | 악취 결합 중합체 및 악취 제어 성분을 포함하는 청향 조성물 |
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| EP3287511A1 (en) | 2010-06-22 | 2018-02-28 | The Procter & Gamble Company | Perfume systems |
| JP5744192B2 (ja) | 2010-06-22 | 2015-07-01 | ザ プロクター アンド ギャンブルカンパニー | 香料系 |
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| MX345025B (es) | 2010-07-02 | 2017-01-12 | Procter & Gamble | Producto detergente. |
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| US8907134B2 (en) * | 2011-02-17 | 2014-12-09 | Firmenich Sa | Perfuming ingredient of the galbanum family |
| WO2012113746A1 (en) * | 2011-02-21 | 2012-08-30 | Firmenich Sa | Consumer products containing pro-fragrances |
| BR112013033049A2 (pt) | 2011-06-23 | 2017-01-31 | Procter & Gamble | sistemas de perfume |
| 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 |
| MX352264B (es) * | 2011-10-06 | 2017-11-16 | Firmenich & Cie | Latex fotolabil para la liberacion de perfumes. |
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| EP4592449A3 (en) | 2012-01-04 | 2025-10-22 | The Procter & Gamble Company | Fibrous structures comprising particles and methods for making same |
| RU2591704C2 (ru) | 2012-01-04 | 2016-07-20 | Дзе Проктер Энд Гэмбл Компани | Содержащие активные агенты волокнистые структуры с множеством областей |
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| JP6000438B2 (ja) | 2012-03-20 | 2016-09-28 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 活性な香料分子の制御放出のための化合物 |
| US20140323383A1 (en) * | 2013-04-26 | 2014-10-30 | The Procter & Gamble Company | Pouch comprising a liquid detergent composition |
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| CN105431126A (zh) * | 2013-07-22 | 2016-03-23 | 高砂香料工业株式会社 | 2,2,6-三甲基环己烷羧酸酯的衍生物 |
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| EP4253649B1 (en) | 2013-12-09 | 2025-04-23 | The Procter & Gamble Company | Fibrous structures including an active agent and having a graphic printed thereon |
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| EP3259339B1 (en) | 2015-02-17 | 2018-10-31 | Firmenich SA | Poly(aspartic acid) derived copolymers for a controlled release of perfuming ingredients |
| WO2016135193A1 (en) | 2015-02-25 | 2016-09-01 | Firmenich Sa | A synergistic perfuming composition |
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| 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) |
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| 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 |
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| US5919752A (en) * | 1997-04-24 | 1999-07-06 | Procter & Gamble | Perfumes having odor longevity benefits |
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-
2002
- 2002-12-11 MX MXPA04005512A patent/MXPA04005512A/es active IP Right Grant
- 2002-12-11 CN CNB028248716A patent/CN1290485C/zh not_active Expired - Lifetime
- 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 EP EP02781640A patent/EP1460994B1/en not_active Expired - Lifetime
- 2002-12-11 WO PCT/IB2002/005365 patent/WO2003049666A2/en not_active Ceased
- 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 JP JP2003550717A patent/JP4694785B2/ja not_active Expired - Lifetime
- 2002-12-11 BR BRPI0214515A patent/BRPI0214515B1/pt active IP Right Grant
- 2002-12-11 RU RU2004121218/04A patent/RU2296118C2/ru not_active IP Right Cessation
- 2002-12-11 PL PL371541A patent/PL209377B1/pl unknown
- 2002-12-11 AU AU2002348801A patent/AU2002348801B2/en not_active Ceased
-
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 |
|---|---|
| JP2010215910A (ja) | 2010-09-30 |
| CN1290485C (zh) | 2006-12-20 |
| JP2005511710A (ja) | 2005-04-28 |
| BR0214515A (pt) | 2004-11-30 |
| WO2003049666A3 (en) | 2004-07-15 |
| RU2296118C2 (ru) | 2007-03-27 |
| ATE409512T1 (de) | 2008-10-15 |
| ES2312635T3 (es) | 2009-03-01 |
| RU2004121218A (ru) | 2006-01-10 |
| CN1602184A (zh) | 2005-03-30 |
| EP1460994B1 (en) | 2008-10-01 |
| DE60229165D1 (de) | 2008-11-13 |
| MXPA04005512A (es) | 2004-12-06 |
| CA2468231A1 (en) | 2003-06-19 |
| BRPI0214515B1 (pt) | 2016-03-22 |
| US20090181878A1 (en) | 2009-07-16 |
| JP4694785B2 (ja) | 2011-06-08 |
| JP5409457B2 (ja) | 2014-02-05 |
| PL371541A1 (en) | 2005-06-27 |
| US20040220074A1 (en) | 2004-11-04 |
| PL209377B1 (pl) | 2011-08-31 |
| US7723286B2 (en) | 2010-05-25 |
| EP1460994A2 (en) | 2004-09-29 |
| US7935669B2 (en) | 2011-05-03 |
| AU2002348801B2 (en) | 2007-11-22 |
| WO2003049666A2 (en) | 2003-06-19 |
| AU2002348801A1 (en) | 2003-06-23 |
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