RU2296118C2 - Соединения для контролируемого высвобождения активных молекул - Google Patents
Соединения для контролируемого высвобождения активных молекул Download PDFInfo
- Publication number
- RU2296118C2 RU2296118C2 RU2004121218/04A RU2004121218A RU2296118C2 RU 2296118 C2 RU2296118 C2 RU 2296118C2 RU 2004121218/04 A RU2004121218/04 A RU 2004121218/04A RU 2004121218 A RU2004121218 A RU 2004121218A RU 2296118 C2 RU2296118 C2 RU 2296118C2
- Authority
- RU
- Russia
- Prior art keywords
- formula
- radical
- group
- methyl
- alkenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 109
- 230000003578 releasing effect Effects 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 10
- 230000002708 enhancing effect Effects 0.000 claims abstract description 6
- 239000002537 cosmetic Substances 0.000 claims abstract description 3
- 238000009792 diffusion process Methods 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- -1 alkenyl hydrocarbon radical Chemical class 0.000 claims description 51
- 239000000047 product Substances 0.000 claims description 44
- 230000015572 biosynthetic process Effects 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000000524 functional group Chemical group 0.000 claims description 27
- 229930195733 hydrocarbon Natural products 0.000 claims description 27
- 150000003254 radicals Chemical class 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000004615 ingredient Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000003599 detergent Substances 0.000 claims description 16
- 150000002576 ketones Chemical class 0.000 claims description 15
- 239000002304 perfume Substances 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001299 aldehydes Chemical class 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 6
- 239000002979 fabric softener Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- VDYYFXXJCMPBTI-UHFFFAOYSA-N 3-(4-bromo-3-methylphenyl)sulfanyl-3-phenylpropanal Chemical compound C1=C(Br)C(C)=CC(SC(CC=O)C=2C=CC=CC=2)=C1 VDYYFXXJCMPBTI-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
- MUEPAPFBHYNUTI-UHFFFAOYSA-N 4-phenylsulfanyl-4-(2,6,6-trimethylcyclohexen-1-yl)butan-2-one Chemical compound CC=1CCCC(C)(C)C=1C(CC(=O)C)SC1=CC=CC=C1 MUEPAPFBHYNUTI-UHFFFAOYSA-N 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 238000010409 ironing Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 claims 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 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 claims 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 claims 1
- CNDOQQKHJYMGDP-UHFFFAOYSA-N CC1C(CC(CC1=O)C(C)C)S(=O)(=O)C2=CC=C(C=C2)C Chemical compound CC1C(CC(CC1=O)C(C)C)S(=O)(=O)C2=CC=C(C=C2)C CNDOQQKHJYMGDP-UHFFFAOYSA-N 0.000 claims 1
- CLCLBNCULYGGJZ-UHFFFAOYSA-N CC1C(CC(CC1=O)C2(CC=CC=C2)C)OCC3=CC=CC=C3 Chemical compound CC1C(CC(CC1=O)C2(CC=CC=C2)C)OCC3=CC=CC=C3 CLCLBNCULYGGJZ-UHFFFAOYSA-N 0.000 claims 1
- MDPFTPYDBHLUOS-UHFFFAOYSA-N CCCCCCCCSC1CC(CC(=O)C1C)C(C)C Chemical compound CCCCCCCCSC1CC(CC(=O)C1C)C(C)C MDPFTPYDBHLUOS-UHFFFAOYSA-N 0.000 claims 1
- 239000007844 bleaching agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 239000000126 substance Substances 0.000 abstract description 9
- 239000000243 solution Substances 0.000 description 68
- 238000005160 1H NMR spectroscopy Methods 0.000 description 38
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 229910004298 SiO 2 Inorganic materials 0.000 description 16
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002585 base Substances 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
- 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 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 8
- 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
- 150000001412 amines Chemical class 0.000 description 7
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- 125000005843 halogen group Chemical group 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000011780 sodium chloride Substances 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
- UECRYUKOKFMTKM-UHFFFAOYSA-N 3-hydroxy-1-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-1-one Chemical compound CC(O)CC(=O)C1C(C)=CCCC1(C)C UECRYUKOKFMTKM-UHFFFAOYSA-N 0.000 description 5
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
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- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 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
- 239000000725 suspension Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
- VZVOPRMLJKLOFD-UHFFFAOYSA-N 1-(2,2,3,6-tetramethylcyclohexyl)but-2-en-1-one Chemical compound CC=CC(=O)C1C(C)CCC(C)C1(C)C VZVOPRMLJKLOFD-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- 229920000742 Cotton Polymers 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- LLWGDNREPDWSRL-UHFFFAOYSA-N cyclopentadec-2-en-1-one Chemical compound O=C1CCCCCCCCCCCCC=C1 LLWGDNREPDWSRL-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 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
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- 229920006301 statistical copolymer Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- OEVIJAZJVZDBQL-UHFFFAOYSA-N 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one Chemical compound CC1(C)CCC=C(C(=O)CCC=C)C1 OEVIJAZJVZDBQL-UHFFFAOYSA-N 0.000 description 2
- 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-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
- 238000005481 NMR spectroscopy Methods 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
- YHYICWSOZQMNAU-UHFFFAOYSA-N [4-oxo-4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl] 3-(dimethylamino)benzoate Chemical compound C=1C=CC(N(C)C)=CC=1C(=O)OC(C)CC(=O)C1C(C)=CCCC1(C)C YHYICWSOZQMNAU-UHFFFAOYSA-N 0.000 description 2
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- 239000008346 aqueous phase Substances 0.000 description 2
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- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 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
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WEHMFTWWOGBHCR-UHFFFAOYSA-N propyl 4-methoxybenzoate Chemical compound CCCOC(=O)C1=CC=C(OC)C=C1 WEHMFTWWOGBHCR-UHFFFAOYSA-N 0.000 description 2
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- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 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
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- 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
- 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)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB0102520 | 2001-12-13 | ||
| IBPCT/IB01/02520 | 2001-12-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004121218A RU2004121218A (ru) | 2006-01-10 |
| RU2296118C2 true RU2296118C2 (ru) | 2007-03-27 |
Family
ID=11004233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004121218/04A RU2296118C2 (ru) | 2001-12-13 | 2002-12-11 | Соединения для контролируемого высвобождения активных молекул |
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|---|---|
| US (2) | US7723286B2 (enExample) |
| EP (1) | EP1460994B1 (enExample) |
| JP (2) | JP4694785B2 (enExample) |
| CN (1) | CN1290485C (enExample) |
| AT (1) | ATE409512T1 (enExample) |
| AU (1) | AU2002348801B2 (enExample) |
| BR (1) | BRPI0214515B1 (enExample) |
| CA (1) | CA2468231A1 (enExample) |
| DE (1) | DE60229165D1 (enExample) |
| ES (1) | ES2312635T3 (enExample) |
| MX (1) | MXPA04005512A (enExample) |
| PL (1) | PL209377B1 (enExample) |
| RU (1) | RU2296118C2 (enExample) |
| WO (1) | WO2003049666A2 (enExample) |
| ZA (1) | ZA200403708B (enExample) |
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| GB0227807D0 (en) * | 2002-11-29 | 2003-01-08 | Givaudan Sa | Improvements in or relating ot organic compounds |
| CN101035823B (zh) * | 2004-10-08 | 2012-07-04 | 弗门尼舍有限公司 | 两亲星型嵌段共聚物 |
| RU2008105617A (ru) * | 2005-07-14 | 2009-08-20 | Фирмениш Са (Ch) | Конъюгаты амфифильных сополимеров для контролируемого выделения активных молекул |
| US20070275866A1 (en) * | 2006-05-23 | 2007-11-29 | Robert Richard Dykstra | Perfume delivery systems for consumer goods |
| EP2074154B1 (en) * | 2006-10-10 | 2011-03-09 | 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 |
| CA2687636A1 (en) * | 2007-06-05 | 2008-12-11 | The Procter & Gamble Company | Perfume systems |
| 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 |
| 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 |
| MX2011005801A (es) | 2008-12-01 | 2011-06-20 | Procter & Gamble | Sistemas de perfume. |
| 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 |
| CN102652175B (zh) | 2009-12-09 | 2016-02-10 | 宝洁公司 | 织物和家居护理产品 |
| JP5782046B2 (ja) | 2009-12-17 | 2015-09-24 | ザ プロクター アンド ギャンブルカンパニー | 悪臭結合ポリマー及び悪臭制御構成成分を含むフレッシュニング組成物 |
| ES2564016T3 (es) | 2010-06-10 | 2016-03-17 | Firmenich Sa | Composiciones perfumantes y usos de las mismas |
| MX2012015201A (es) | 2010-06-22 | 2013-01-24 | Procter & Gamble | Sistemas de perfumeria. |
| EP3121256B1 (en) | 2010-06-22 | 2018-12-12 | The Procter and Gamble Company | Perfume systems |
| RU2543892C2 (ru) | 2010-07-02 | 2015-03-10 | Дзе Проктер Энд Гэмбл Компани | Способ получения пленок из нетканых полотен |
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| CN105647715B (zh) | 2010-07-02 | 2019-10-25 | 宝洁公司 | 洗涤剂产品 |
| 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. |
| RU2555042C2 (ru) | 2010-07-02 | 2015-07-10 | Дзе Проктер Энд Гэмбл Компани | Способ доставки активнодействующего вещества |
| 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 |
| EP2678413A1 (en) * | 2011-02-21 | 2014-01-01 | Firmenich SA | Consumer products containing pro-fragrances |
| MX336357B (es) | 2011-06-23 | 2016-01-14 | Procter & Gamble | Sistemas de perfume. |
| 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 |
| EP2748208B1 (en) * | 2011-10-06 | 2016-06-22 | Firmenich SA | Photolabile latex for the release of perfumes |
| BR112014009848B1 (pt) | 2011-10-27 | 2019-02-26 | Firmenich Sa | Composições de perfumaria e seus usos |
| MX341723B (es) | 2011-11-04 | 2016-08-31 | Firmenich & Cie | Composiciones perfumantes y usos de las mismas. |
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| US20130171421A1 (en) | 2012-01-04 | 2013-07-04 | The Procter & Gamble Company | Active containing fibrous structures with multiple regions having differing characteristics |
| CA2860659C (en) | 2012-01-04 | 2017-08-29 | The Procter & Gamble Company | Fibrous structures comprising particles and methods for making same |
| WO2013139766A1 (en) | 2012-03-20 | 2013-09-26 | Firmenich Sa | Compounds for a controlled release of active perfuming molecules |
| US20140323383A1 (en) * | 2013-04-26 | 2014-10-30 | The Procter & Gamble Company | Pouch comprising a liquid detergent composition |
| EP3010960A1 (en) * | 2013-06-19 | 2016-04-27 | Firmenich SA | Polysiloxane conjugates as fragrance delivery systems |
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| WO2015032885A1 (en) | 2013-09-09 | 2015-03-12 | Firmenich Sa | Thioether derivatives as precursors for a controlled release of active molecules |
| EP3080344B1 (en) | 2013-12-09 | 2019-10-09 | The Procter and Gamble Company | Fibrous structures including an active agent and having a graphic printed thereon |
| US10113135B2 (en) | 2013-12-19 | 2018-10-30 | Kao Corporation | Perfuming method |
| US20150217015A1 (en) * | 2014-02-04 | 2015-08-06 | The Procter & Gamble Company | Long lasting freshening compositions |
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| CN107250339B (zh) * | 2015-02-17 | 2020-07-17 | 弗门尼舍有限公司 | 用于加香成分受控释放的由聚(天冬氨酸)衍生的共聚物 |
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| DE60000397T2 (de) * | 1999-08-18 | 2003-05-22 | Givaudan Sa, Vernier | Weichmittelzusammensetzung |
| JP4071421B2 (ja) * | 2000-06-07 | 2008-04-02 | 高砂香料工業株式会社 | シクロヘキセニルメチルケトンの製造法 |
| ES2298319T3 (es) * | 2001-12-05 | 2008-05-16 | Firmenich Sa | Ester insaturado como ingrediente perfumante. |
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2002
- 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 AT AT02781640T patent/ATE409512T1/de not_active IP Right Cessation
- 2002-12-11 CA CA002468231A patent/CA2468231A1/en not_active Abandoned
- 2002-12-11 AU AU2002348801A patent/AU2002348801B2/en not_active Ceased
- 2002-12-11 WO PCT/IB2002/005365 patent/WO2003049666A2/en not_active Ceased
- 2002-12-11 DE DE60229165T patent/DE60229165D1/de not_active Expired - Lifetime
- 2002-12-11 BR BRPI0214515A patent/BRPI0214515B1/pt active IP Right Grant
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- 2002-12-11 JP JP2003550717A patent/JP4694785B2/ja not_active Expired - Lifetime
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- 2002-12-11 ES ES02781640T patent/ES2312635T3/es not_active Expired - Lifetime
- 2002-12-11 EP EP02781640A patent/EP1460994B1/en not_active Expired - Lifetime
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- 2004-05-14 ZA ZA2004/03708A patent/ZA200403708B/en unknown
- 2004-05-25 US US10/852,754 patent/US7723286B2/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| PL209377B1 (pl) | 2011-08-31 |
| JP2005511710A (ja) | 2005-04-28 |
| US20090181878A1 (en) | 2009-07-16 |
| ZA200403708B (en) | 2005-06-29 |
| WO2003049666A2 (en) | 2003-06-19 |
| US7935669B2 (en) | 2011-05-03 |
| PL371541A1 (en) | 2005-06-27 |
| US7723286B2 (en) | 2010-05-25 |
| AU2002348801B2 (en) | 2007-11-22 |
| JP5409457B2 (ja) | 2014-02-05 |
| US20040220074A1 (en) | 2004-11-04 |
| DE60229165D1 (de) | 2008-11-13 |
| ATE409512T1 (de) | 2008-10-15 |
| EP1460994A2 (en) | 2004-09-29 |
| BR0214515A (pt) | 2004-11-30 |
| JP4694785B2 (ja) | 2011-06-08 |
| JP2010215910A (ja) | 2010-09-30 |
| RU2004121218A (ru) | 2006-01-10 |
| ES2312635T3 (es) | 2009-03-01 |
| CA2468231A1 (en) | 2003-06-19 |
| EP1460994B1 (en) | 2008-10-01 |
| WO2003049666A3 (en) | 2004-07-15 |
| CN1602184A (zh) | 2005-03-30 |
| MXPA04005512A (es) | 2004-12-06 |
| CN1290485C (zh) | 2006-12-20 |
| AU2002348801A1 (en) | 2003-06-23 |
| BRPI0214515B1 (pt) | 2016-03-22 |
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| MM4A | The patent is invalid due to non-payment of fees |
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