KR20090113260A - 활성 알데히드 및 케톤의 평형 유동 혼합물로부터의 제어 방출 - Google Patents
활성 알데히드 및 케톤의 평형 유동 혼합물로부터의 제어 방출 Download PDFInfo
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- KR20090113260A KR20090113260A KR1020097014238A KR20097014238A KR20090113260A KR 20090113260 A KR20090113260 A KR 20090113260A KR 1020097014238 A KR1020097014238 A KR 1020097014238A KR 20097014238 A KR20097014238 A KR 20097014238A KR 20090113260 A KR20090113260 A KR 20090113260A
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- South Korea
- Prior art keywords
- group
- formula
- diamine
- optionally substituted
- derivative
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 157
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 118
- 150000002576 ketones Chemical class 0.000 title claims abstract description 96
- 238000013270 controlled release Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 239000003205 fragrance Substances 0.000 claims description 90
- 239000000047 product Substances 0.000 claims description 48
- 239000002585 base Substances 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 239000002304 perfume Substances 0.000 claims description 34
- -1 iminomethylene Chemical group 0.000 claims description 32
- 239000000796 flavoring agent Substances 0.000 claims description 25
- 235000019634 flavors Nutrition 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 13
- 241000607479 Yersinia pestis Species 0.000 claims description 12
- 239000002386 air freshener Substances 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 10
- 239000005871 repellent Substances 0.000 claims description 10
- 230000002940 repellent Effects 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 239000005667 attractant Substances 0.000 claims description 9
- 239000003599 detergent Substances 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 150000007854 aminals Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 6
- 230000031902 chemoattractant activity Effects 0.000 claims description 6
- RXLUOFXICZSZIB-UHFFFAOYSA-N n,n'-dibenzylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1CNCCCNCC1=CC=CC=C1 RXLUOFXICZSZIB-UHFFFAOYSA-N 0.000 claims description 6
- 230000001166 anti-perspirative effect Effects 0.000 claims description 5
- 239000003213 antiperspirant Substances 0.000 claims description 5
- 239000002781 deodorant agent Substances 0.000 claims description 5
- SJBYIGXWWGSEES-UHFFFAOYSA-N 1-n,2-n-dibenzylcyclohexane-1,2-diamine Chemical compound C=1C=CC=CC=1CNC1CCCCC1NCC1=CC=CC=C1 SJBYIGXWWGSEES-UHFFFAOYSA-N 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- FKJLUBFUVIGVQS-UHFFFAOYSA-N n,n'-bis[(4-ethylphenyl)methyl]ethane-1,2-diamine Chemical compound C1=CC(CC)=CC=C1CNCCNCC1=CC=C(CC)C=C1 FKJLUBFUVIGVQS-UHFFFAOYSA-N 0.000 claims description 4
- AVHNOBYTCDKTEV-UHFFFAOYSA-N n,n'-bis[(4-methoxyphenyl)methyl]ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CNCCNCC1=CC=C(OC)C=C1 AVHNOBYTCDKTEV-UHFFFAOYSA-N 0.000 claims description 4
- CKCCOVSHDQOTNC-UHFFFAOYSA-N n,n'-bis[[4-(dimethylamino)phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(N(C)C)=CC=C1CNCCNCC1=CC=C(N(C)C)C=C1 CKCCOVSHDQOTNC-UHFFFAOYSA-N 0.000 claims description 4
- UCVBNHJQXVIAEU-UHFFFAOYSA-N n,n'-bis[[4-(dimethylamino)phenyl]methyl]propane-1,3-diamine Chemical compound C1=CC(N(C)C)=CC=C1CNCCCNCC1=CC=C(N(C)C)C=C1 UCVBNHJQXVIAEU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000077 insect repellent Substances 0.000 claims description 3
- 238000010409 ironing Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- QVGJBXLXNGAZPZ-UHFFFAOYSA-N n,n'-bis[(4-methoxyphenyl)methyl]propane-1,3-diamine Chemical compound C1=CC(OC)=CC=C1CNCCCNCC1=CC=C(OC)C=C1 QVGJBXLXNGAZPZ-UHFFFAOYSA-N 0.000 claims description 3
- MBHFHLMJDQZVTL-UHFFFAOYSA-N 1,2,3-tribenzylimidazolidine Chemical compound C=1C=CC=CC=1CC(N(CC1)CC=2C=CC=CC=2)N1CC1=CC=CC=C1 MBHFHLMJDQZVTL-UHFFFAOYSA-N 0.000 claims description 2
- SUZXCMFTAFNBCZ-UHFFFAOYSA-N 1,3-dibenzyl-2-(2-phenylethenyl)imidazolidine Chemical compound C=1C=CC=CC=1CN(C1C=CC=2C=CC=CC=2)CCN1CC1=CC=CC=C1 SUZXCMFTAFNBCZ-UHFFFAOYSA-N 0.000 claims description 2
- ZJVDSVMMDFKVJR-UHFFFAOYSA-N 1,3-dibenzyl-2-hexylimidazolidine Chemical compound C1CN(CC=2C=CC=CC=2)C(CCCCCC)N1CC1=CC=CC=C1 ZJVDSVMMDFKVJR-UHFFFAOYSA-N 0.000 claims description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 2
- 241000195940 Bryophyta Species 0.000 claims description 2
- BYTKQYBUDUPJFC-UHFFFAOYSA-N N,N'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1.C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 BYTKQYBUDUPJFC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 235000011929 mousse Nutrition 0.000 claims description 2
- QEUWNGJNPLRKLR-UHFFFAOYSA-N n,n'-dibenzyl-1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CNC(C=1C=CC=CC=1)C(C=1C=CC=CC=1)NCC1=CC=CC=C1 QEUWNGJNPLRKLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 1
- 150000008365 aromatic ketones Chemical class 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 abstract description 77
- 239000012530 fluid Substances 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000306 component Substances 0.000 description 42
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 230000002441 reversible effect Effects 0.000 description 13
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002979 fabric softener Substances 0.000 description 10
- 239000000499 gel Substances 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000002453 shampoo Substances 0.000 description 10
- 150000001413 amino acids Chemical class 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 8
- 239000013074 reference sample Substances 0.000 description 8
- 238000005070 sampling Methods 0.000 description 8
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 150000001491 aromatic compounds Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 6
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 description 5
- QMXBURPYNWBMJR-UHFFFAOYSA-N 6-methoxy-2,6-dimethylheptanal Chemical compound COC(C)(C)CCCC(C)C=O QMXBURPYNWBMJR-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229910052805 deuterium Inorganic materials 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000001976 improved effect Effects 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- SJBYIGXWWGSEES-WOJBJXKFSA-N (1r,2r)-1-n,2-n-dibenzylcyclohexane-1,2-diamine Chemical compound N([C@@H]1CCCC[C@H]1NCC=1C=CC=CC=1)CC1=CC=CC=C1 SJBYIGXWWGSEES-WOJBJXKFSA-N 0.000 description 4
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 4
- SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
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- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
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- VNWOJVJCRAHBJJ-UHFFFAOYSA-N 2-pentylcyclopentan-1-one Chemical compound CCCCCC1CCCC1=O VNWOJVJCRAHBJJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
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- 230000005923 long-lasting effect Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- 239000012044 organic layer Substances 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
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- 239000008399 tap water Substances 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- NEHNMFOYXAPHSD-SNVBAGLBSA-N (+)-Citronellal Chemical compound O=CC[C@H](C)CCC=C(C)C NEHNMFOYXAPHSD-SNVBAGLBSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- AYFJNMWCQAJEON-UHFFFAOYSA-N 1,3-dibenzyl-2-phenyl-1,3-diazinane Chemical compound C=1C=CC=CC=1CN(C1C=2C=CC=CC=2)CCCN1CC1=CC=CC=C1 AYFJNMWCQAJEON-UHFFFAOYSA-N 0.000 description 2
- DXIWBWIDAYBUDF-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexyl)ethanone Chemical compound CC(=O)C1CCCC(C)(C)C1 DXIWBWIDAYBUDF-UHFFFAOYSA-N 0.000 description 2
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 2
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- ALHUZKCOMYUFRB-UHFFFAOYSA-N 3-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 2
- MYHGOWDLVRDUFA-UHFFFAOYSA-N 3-phenylbutanal Chemical compound O=CCC(C)C1=CC=CC=C1 MYHGOWDLVRDUFA-UHFFFAOYSA-N 0.000 description 2
- WKQWDIFHKYWRTA-UHFFFAOYSA-N 4,7-dimethyloct-6-en-3-one Chemical compound CCC(=O)C(C)CC=C(C)C WKQWDIFHKYWRTA-UHFFFAOYSA-N 0.000 description 2
- DCSKAMGZSIRJAQ-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)cyclohexan-1-one Chemical compound CCC(C)(C)C1CCC(=O)CC1 DCSKAMGZSIRJAQ-UHFFFAOYSA-N 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- JHJCHCSUEGPIGE-UHFFFAOYSA-N 7,8-Dihydro-alpha-ionone Chemical compound CC(=O)CCC1C(C)=CCCC1(C)C JHJCHCSUEGPIGE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012062 aqueous buffer Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- FZJUFJKVIYFBSY-UHFFFAOYSA-N bourgeonal Chemical compound CC(C)(C)C1=CC=C(CCC=O)C=C1 FZJUFJKVIYFBSY-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000012482 calibration solution Substances 0.000 description 2
- SWUIQEBPZIHZQS-UHFFFAOYSA-N calone Chemical compound O1CC(=O)COC2=CC(C)=CC=C21 SWUIQEBPZIHZQS-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A61Q13/00—Formulations or additives for perfume preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- 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
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- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
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| EP07116890 | 2007-09-21 | ||
| PCT/IB2008/050289 WO2008093272A2 (en) | 2007-01-30 | 2008-01-28 | Controlled release of active aldehydes and ketones from equilibrated dynamic mixtures |
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| 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 |
| US9101783B2 (en) | 2009-06-19 | 2015-08-11 | Firmenich Sa | Malodor counteracting compositions and method for their use to counteract sweat malodor |
| WO2011154926A1 (en) | 2010-06-10 | 2011-12-15 | Firmenich Sa | Perfuming compositions and uses thereof |
| EP2697347B1 (en) | 2011-04-13 | 2016-11-16 | Firmenich SA | Equilibrated dynamic mixtures to control the release of perfuming aldehydes and ketones |
| 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 |
| RU2662196C1 (ru) * | 2014-11-10 | 2018-07-24 | Живодан Са | Усовершенствование органических соединений или усовершенствование, относящееся к органическим соединениям |
| WO2016074118A1 (en) | 2014-11-10 | 2016-05-19 | Givaudan Sa | Improvements in or relating to organic compounds |
| EP3533786A1 (en) | 2018-03-02 | 2019-09-04 | Givaudan SA | Thioether precursors for fragrant ketones and aldehydes |
| EP4034073A1 (en) * | 2019-12-20 | 2022-08-03 | Firmenich SA | Pro-perfume compositions |
| CN115926893B (zh) * | 2021-10-20 | 2024-06-25 | 中国科学院化学研究所 | 一种可循环利用的清洗剂及其制备方法与应用 |
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| JPS58141225A (ja) * | 1982-02-16 | 1983-08-22 | Takasago Corp | 芳香材用樹脂組成物 |
| EP0571677A1 (en) * | 1992-05-29 | 1993-12-01 | Unilever Plc | Aqueous parfume oil microemulsions |
| US6096704A (en) * | 1997-03-21 | 2000-08-01 | Bryant, Jr.; Lonnie Liddell | Pro-fragrance compound |
| EP0971021A1 (en) * | 1998-07-10 | 2000-01-12 | The Procter & Gamble Company | Process for producing particles of amine reaction product |
| EP0971027A1 (en) * | 1998-07-10 | 2000-01-12 | The Procter & Gamble Company | Amine reaction compounds comprising one or more active ingredient |
| US6790815B1 (en) * | 1998-07-10 | 2004-09-14 | Procter & Gamble Company | Amine reaction compounds comprising one or more active ingredient |
| EP0971025A1 (en) * | 1998-07-10 | 2000-01-12 | The Procter & Gamble Company | Amine reaction compounds comprising one or more active ingredient |
| AU6049401A (en) * | 2000-06-02 | 2001-12-17 | Quest International B.V. | Improvements in or relating to perfumes |
| BRPI0514109A (pt) * | 2004-08-05 | 2008-05-27 | Firmenich & Cie | sistema de administração na forma de uma mistura dinámica, composição para perfumar, artigo para consumidor, artigo perfumado, e, usos de um sistema de administração e de um derivado de hidrazina |
| DE102005062175A1 (de) * | 2005-12-23 | 2007-06-28 | Henkel Kgaa | Cyclische Aminale als Duftstoffe |
-
2008
- 2008-01-28 MX MX2009007714A patent/MX2009007714A/es active IP Right Grant
- 2008-01-28 DE DE602008002711T patent/DE602008002711D1/de active Active
- 2008-01-28 BR BRPI0807022A patent/BRPI0807022B1/pt not_active IP Right Cessation
- 2008-01-28 PL PL08702535T patent/PL2114899T3/pl unknown
- 2008-01-28 KR KR1020097014238A patent/KR20090113260A/ko not_active Ceased
- 2008-01-28 US US12/523,964 patent/US20100098650A1/en not_active Abandoned
- 2008-01-28 EP EP08702535A patent/EP2114899B1/en active Active
- 2008-01-28 WO PCT/IB2008/050289 patent/WO2008093272A2/en not_active Ceased
- 2008-01-28 JP JP2009547787A patent/JP5453112B2/ja not_active Expired - Fee Related
- 2008-01-28 AT AT08702535T patent/ATE482203T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2114899B1 (en) | 2010-09-22 |
| BRPI0807022B1 (pt) | 2016-06-14 |
| JP2010516804A (ja) | 2010-05-20 |
| ATE482203T1 (de) | 2010-10-15 |
| US20100098650A1 (en) | 2010-04-22 |
| EP2114899A2 (en) | 2009-11-11 |
| WO2008093272A2 (en) | 2008-08-07 |
| MX2009007714A (es) | 2009-12-14 |
| WO2008093272A3 (en) | 2008-10-09 |
| BRPI0807022A2 (pt) | 2015-06-16 |
| JP5453112B2 (ja) | 2014-03-26 |
| DE602008002711D1 (de) | 2010-11-04 |
| PL2114899T3 (pl) | 2011-02-28 |
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