BRPI0214515B1 - composição de perfume ou artigo perfumado, método para melhorar, intensificar ou modificar o odor de um artigo perfumado ou composição de perfume, método para perfumar uma superfície, método para intensificar ou prolongar o efeito de difusão de um ingrediente odorífero sobre uma superfície, e, composto - Google Patents
composição de perfume ou artigo perfumado, método para melhorar, intensificar ou modificar o odor de um artigo perfumado ou composição de perfume, método para perfumar uma superfície, método para intensificar ou prolongar o efeito de difusão de um ingrediente odorífero sobre uma superfície, e, composto Download PDFInfo
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- BRPI0214515B1 BRPI0214515B1 BRPI0214515A BR0214515A BRPI0214515B1 BR PI0214515 B1 BRPI0214515 B1 BR PI0214515B1 BR PI0214515 A BRPI0214515 A BR PI0214515A BR 0214515 A BR0214515 A BR 0214515A BR PI0214515 B1 BRPI0214515 B1 BR PI0214515B1
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- Prior art keywords
- formulas
- formula
- group
- radical
- perfume
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 239000002304 perfume Substances 0.000 title claims description 47
- 239000004615 ingredient Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 16
- 230000000694 effects Effects 0.000 title claims description 11
- 230000002708 enhancing effect Effects 0.000 title claims description 4
- 238000009792 diffusion process Methods 0.000 title claims description 3
- 150000002576 ketones Chemical class 0.000 claims abstract description 14
- -1 2-cyclohexen-1-yl Chemical group 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- 125000000524 functional group Chemical group 0.000 claims description 25
- 229930195733 hydrocarbon Natural products 0.000 claims description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000003205 fragrance Substances 0.000 claims description 14
- 239000003599 detergent Substances 0.000 claims description 12
- 150000001412 amines Chemical group 0.000 claims description 10
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 claims description 9
- 239000002979 fabric softener Substances 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000001033 ether group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical group 0.000 claims description 5
- 150000002148 esters Chemical group 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 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 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 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
- 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 claims description 2
- 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 2
- 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 2
- 239000002386 air freshener Substances 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 238000010409 ironing Methods 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 claims 1
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 241000195940 Bryophyta Species 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000007844 bleaching agent Substances 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 235000011929 mousse Nutrition 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 abstract description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 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 15
- 239000000047 product Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 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
- 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
- 229910004809 Na2 SO4 Inorganic materials 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 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
- 238000002474 experimental method Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000011780 sodium chloride Substances 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
- 239000000178 monomer Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- LTHDEPSKZBGNNV-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl 4-ethenylbenzoate Chemical compound COCCOCCOCCOC(=O)C1=CC=C(C=C)C=C1 LTHDEPSKZBGNNV-UHFFFAOYSA-N 0.000 description 5
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 4
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 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
- 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 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
- 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 3
- 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 235000009827 Prunus armeniaca Nutrition 0.000 description 3
- 244000018633 Prunus armeniaca Species 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 125000003118 aryl group Chemical group 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
- 239000000872 buffer Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 125000003827 glycol group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000000725 suspension Substances 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 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
- 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
- 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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 125000004429 atom Chemical group 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
- POIARNZEYGURDG-UHFFFAOYSA-N beta-damascenone Natural products CC=CC(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001816 cooling Methods 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
- 238000004821 distillation Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 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
- ZNJKZZJSZFQNRW-UHFFFAOYSA-N methyl 2-(1-ethoxyethoxy)-5,5-dimethylcyclohexane-1-carboxylate Chemical compound CCOC(C)OC1CCC(C)(C)CC1C(=O)OC ZNJKZZJSZFQNRW-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound 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
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 150000003505 terpenes Chemical class 0.000 description 1
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- 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
- UPATWGCKQJILNW-UHFFFAOYSA-N tris[4-oxo-4-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl] benzene-1,3,5-tricarboxylate Chemical compound C=1C(C(=O)OC(C)CC(=O)C2C(CC=CC2C)(C)C)=CC(C(=O)OC(C)CC(=O)C2C(CC=CC2C)(C)C)=CC=1C(=O)OC(C)CC(=O)C1C(C)C=CCC1(C)C UPATWGCKQJILNW-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000000341 volatile oil 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
- 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 (2)
| Publication Number | Publication Date |
|---|---|
| BR0214515A BR0214515A (pt) | 2004-11-30 |
| BRPI0214515B1 true BRPI0214515B1 (pt) | 2016-03-22 |
Family
ID=11004233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0214515A BRPI0214515B1 (pt) | 2001-12-13 | 2002-12-11 | composição de perfume ou artigo perfumado, método para melhorar, intensificar ou modificar o odor de um artigo perfumado ou composição de perfume, método para perfumar uma superfície, método para intensificar ou prolongar o efeito de difusão de um ingrediente odorífero sobre uma superfície, e, composto |
Country Status (15)
| Country | Link |
|---|---|
| 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) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0227807D0 (en) * | 2002-11-29 | 2003-01-08 | Givaudan Sa | Improvements in or relating ot organic compounds |
| BRPI0516259A (pt) * | 2004-10-08 | 2008-08-26 | Firmenich & Cie | composto de copolìmero em bloco, copolìmero em bloco, nano-cápsula, processo para manufaturar o copolìmero em bloco, uso do copolìmero em bloco, método para encapsular e/ou associar com pelo menos um agente funcional lipofìlico, e, produto perfumado |
| 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 |
| DE602007013074D1 (de) * | 2006-10-10 | 2011-04-21 | 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 |
| MX2009013338A (es) * | 2007-06-05 | 2010-01-18 | Procter & Gamble | Sistemas de perfume. |
| JP2012502092A (ja) | 2008-09-12 | 2012-01-26 | フイルメニツヒ ソシエテ アノニム | 活性アルデヒドおよびケトンを放出できるジビニルエーテル誘導体および芳香表面への使用方法 |
| WO2010046832A2 (en) | 2008-10-21 | 2010-04-29 | Firmenich Sa | Perfuming compositions and uses thereof |
| US20100102142A1 (en) * | 2008-10-28 | 2010-04-29 | Daria Tagliareni | Scent dispenser assembly |
| EP2362765B1 (en) | 2008-12-01 | 2020-04-08 | The Procter and Gamble Company | Perfume systems |
| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| US9101783B2 (en) | 2009-06-19 | 2015-08-11 | 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 |
| WO2011072117A1 (en) | 2009-12-09 | 2011-06-16 | The Procter & Gamble Company | Fabric and home care products |
| WO2011084463A1 (en) | 2009-12-17 | 2011-07-14 | The Procter & Gamble Company | Freshening compositions comprising malodor binding polymers and malodor control components |
| WO2011154926A1 (en) | 2010-06-10 | 2011-12-15 | Firmenich Sa | Perfuming compositions and uses thereof |
| ES2666195T3 (es) | 2010-06-22 | 2018-05-03 | The Procter & Gamble Company | Sistema de perfume |
| CN107012022A (zh) | 2010-06-22 | 2017-08-04 | 宝洁公司 | 香料体系 |
| RU2555042C2 (ru) | 2010-07-02 | 2015-07-10 | Дзе Проктер Энд Гэмбл Компани | Способ доставки активнодействующего вещества |
| EP3533908A1 (en) | 2010-07-02 | 2019-09-04 | The Procter & Gamble Company | Nonwoven web comprising one or more active agents |
| CA2803371C (en) | 2010-07-02 | 2016-04-19 | The Procter & Gamble Company | Process for making films from nonwoven webs |
| WO2012003319A2 (en) | 2010-07-02 | 2012-01-05 | The Procter & Gamble Company | Filaments comprising an active agent nonwoven webs and methods for making same |
| MX2012015169A (es) | 2010-07-02 | 2013-05-09 | Procter & Gamble | Filamentos que comprenden un agente activo sin perfume, tramas de tela no tejida y métodos para elaborarlos. |
| MX354501B (es) * | 2011-02-17 | 2018-03-08 | Firmenich & Cie | Ingrediente perfumante de la familia galbano. |
| 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 |
| 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 |
| JP6092229B2 (ja) * | 2011-10-06 | 2017-03-08 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 香料の放出のための感光性ラテックス |
| MX343010B (es) | 2011-10-27 | 2016-10-21 | Firmenich & Cie | Composiciones perfumantes y usos de las mismas. |
| WO2013064412A2 (en) | 2011-11-04 | 2013-05-10 | Firmenich Sa | Perfuming compositions and uses thereof |
| MX353496B (es) | 2012-01-04 | 2018-01-16 | Procter & Gamble | Estructuras fibrosas que contienen activos con múltiples regiones. |
| CA2860647C (en) | 2012-01-04 | 2022-06-14 | The Procter & Gamble Company | Active containing fibrous structures with multiple regions having differing densities |
| WO2013103630A1 (en) | 2012-01-04 | 2013-07-11 | The Procter & Gamble Company | Fibrous structures comprising particles and methods for making same |
| EP2828240B1 (en) | 2012-03-20 | 2018-10-31 | 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 |
| CN105324416B (zh) * | 2013-06-19 | 2018-11-16 | 弗门尼舍有限公司 | 作为香料递送系统的聚硅氧烷偶联物 |
| WO2015013184A1 (en) * | 2013-07-22 | 2015-01-29 | Takasago International Corp.(USA) | Derivatives of 2,2,6-trimethylcyclohexane-carboxylate |
| 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 |
| 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 |
| JP6713476B2 (ja) * | 2015-02-17 | 2020-06-24 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 賦香性成分の放出制御のためのポリ（アスパラギン酸）から誘導されるコポリマー |
| WO2016135193A1 (en) | 2015-02-25 | 2016-09-01 | Firmenich Sa | A synergistic perfuming composition |
| 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 |
| US10632221B2 (en) * | 2016-03-28 | 2020-04-28 | The Procter & Gamble Company | Long lasting and stable freshening compositions and methods of freshening the air |
| BR112019003725B1 (pt) | 2016-08-25 | 2022-08-23 | Firmenich S.A | Composição de antiperspirante ou desodorante |
| US11697905B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | Active agent-containing articles that exhibit consumer acceptable article in-use properties |
| JP6886045B2 (ja) | 2017-01-27 | 2021-06-16 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | 消費者に許容可能な物品使用特性を示す、活性剤含有物品 |
| US11697904B2 (en) | 2017-01-27 | 2023-07-11 | The Procter & Gamble Company | 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 |
| EP3533786A1 (en) | 2018-03-02 | 2019-09-04 | Givaudan SA | Thioether precursors for fragrant ketones and aldehydes |
| GB201803410D0 (en) * | 2018-03-02 | 2018-04-18 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN111971371A (zh) * | 2018-06-21 | 2020-11-20 | 弗门尼舍有限公司 | 提供持久草莓气味的化合物 |
| US12264295B2 (en) | 2019-03-20 | 2025-04-01 | Firmenich Sa | Encapsulated pro-perfume compounds |
| BR112021019676B1 (pt) | 2019-05-07 | 2023-12-26 | Givaudan Sa | Compostos orgânicos |
| WO2020260598A1 (en) | 2019-06-27 | 2020-12-30 | Firmenich Sa | Perfumed consumer products |
| JP6850834B2 (ja) * | 2019-07-19 | 2021-03-31 | ライオン株式会社 | 液体柔軟剤組成物 |
| CN110845629A (zh) * | 2019-12-02 | 2020-02-28 | 佛山欧神诺陶瓷有限公司 | 一种反应型香味缓释纳米微晶纤维素及其制备方法 |
| WO2021113568A1 (en) | 2019-12-05 | 2021-06-10 | The Procter & Gamble Company | Method of making a cleaning composition |
| US12122981B2 (en) | 2019-12-05 | 2024-10-22 | The Procter & Gamble Company | Cleaning composition |
| US12291689B2 (en) | 2019-12-19 | 2025-05-06 | Firmenich Sa | Compounds for providing a long-lasting floral and fruity odor |
| CN114729287A (zh) * | 2019-12-20 | 2022-07-08 | 弗门尼舍有限公司 | 皂组合物 |
| WO2021152023A1 (en) | 2020-01-28 | 2021-08-05 | Sensient Fragrances, S.A. | Selenide derivatives of fragrance compounds |
| BR112022024694A2 (pt) * | 2020-06-03 | 2023-02-28 | Int Flavors & Fragrances Inc | Composto pró-fragrância, sistema de entrega, produto de consumo e método de preparação de um composto pró-fragrância |
| EP4196564A1 (en) | 2020-09-24 | 2023-06-21 | Firmenich SA | Consumer products containing pro-fragrances |
| JP2023547303A (ja) | 2020-10-23 | 2023-11-10 | フイルメニツヒ ソシエテ アノニム | 汗臭の知覚を抑制または除去するための組成物 |
| MX2023008851A (es) | 2021-02-11 | 2023-08-15 | Firmenich & Cie | Proceso para la preparacion de un tioeter. |
| US20230220300A1 (en) * | 2022-01-13 | 2023-07-13 | The Procter & Gamble Company | Treatment compositions with modified amino acid multimers |
| WO2024261201A1 (en) | 2023-06-21 | 2024-12-26 | Givaudan Sa | New compounds |
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-
2002
- 2002-12-11 RU RU2004121218/04A patent/RU2296118C2/ru not_active IP Right Cessation
- 2002-12-11 JP JP2003550717A patent/JP4694785B2/ja not_active Expired - Lifetime
- 2002-12-11 WO PCT/IB2002/005365 patent/WO2003049666A2/en not_active Ceased
- 2002-12-11 PL PL371541A patent/PL209377B1/pl unknown
- 2002-12-11 MX MXPA04005512A patent/MXPA04005512A/es active IP Right Grant
- 2002-12-11 AT AT02781640T patent/ATE409512T1/de not_active IP Right Cessation
- 2002-12-11 DE DE60229165T patent/DE60229165D1/de not_active Expired - Lifetime
- 2002-12-11 EP EP02781640A patent/EP1460994B1/en not_active Expired - Lifetime
- 2002-12-11 CA CA002468231A patent/CA2468231A1/en not_active Abandoned
- 2002-12-11 CN CNB028248716A patent/CN1290485C/zh not_active Expired - Lifetime
- 2002-12-11 AU AU2002348801A patent/AU2002348801B2/en not_active Ceased
- 2002-12-11 BR BRPI0214515A patent/BRPI0214515B1/pt active IP Right Grant
- 2002-12-11 ES ES02781640T patent/ES2312635T3/es 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 |
|---|---|
| ZA200403708B (en) | 2005-06-29 |
| PL209377B1 (pl) | 2011-08-31 |
| RU2004121218A (ru) | 2006-01-10 |
| JP5409457B2 (ja) | 2014-02-05 |
| US7723286B2 (en) | 2010-05-25 |
| ES2312635T3 (es) | 2009-03-01 |
| US7935669B2 (en) | 2011-05-03 |
| CN1290485C (zh) | 2006-12-20 |
| JP2005511710A (ja) | 2005-04-28 |
| CN1602184A (zh) | 2005-03-30 |
| WO2003049666A3 (en) | 2004-07-15 |
| CA2468231A1 (en) | 2003-06-19 |
| WO2003049666A2 (en) | 2003-06-19 |
| PL371541A1 (en) | 2005-06-27 |
| AU2002348801B2 (en) | 2007-11-22 |
| JP4694785B2 (ja) | 2011-06-08 |
| JP2010215910A (ja) | 2010-09-30 |
| EP1460994A2 (en) | 2004-09-29 |
| RU2296118C2 (ru) | 2007-03-27 |
| MXPA04005512A (es) | 2004-12-06 |
| EP1460994B1 (en) | 2008-10-01 |
| ATE409512T1 (de) | 2008-10-15 |
| BR0214515A (pt) | 2004-11-30 |
| US20090181878A1 (en) | 2009-07-16 |
| US20040220074A1 (en) | 2004-11-04 |
| DE60229165D1 (de) | 2008-11-13 |
| AU2002348801A1 (en) | 2003-06-23 |
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Ipc: C11D 3/50 (2006.01), C11B 9/00 (2006.01) |