DE69933608T2 - Verbindungen mit geschützten Hydroxylgruppen - Google Patents
Verbindungen mit geschützten Hydroxylgruppen Download PDFInfo
- Publication number
- DE69933608T2 DE69933608T2 DE69933608T DE69933608T DE69933608T2 DE 69933608 T2 DE69933608 T2 DE 69933608T2 DE 69933608 T DE69933608 T DE 69933608T DE 69933608 T DE69933608 T DE 69933608T DE 69933608 T2 DE69933608 T2 DE 69933608T2
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- DE
- Germany
- Prior art keywords
- acid
- ester
- dimethyl
- substituted
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 31
- 239000003599 detergent Substances 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000002596 lactones Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000002979 fabric softener Substances 0.000 claims description 8
- 230000003213 activating effect Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 2
- 150000004718 beta keto acids Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 244000005714 skin microbiome Species 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 238000004851 dishwashing Methods 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002587 enol group Chemical group 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 29
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- -1 aromatic radicals Chemical class 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000003205 fragrance Substances 0.000 description 24
- 239000002243 precursor Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000002304 perfume Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 235000019645 odor Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- SPUWOYCLMKSXKU-UHFFFAOYSA-N 4-oxo capric acid Chemical compound CCCCCCC(=O)CCC(O)=O SPUWOYCLMKSXKU-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 102000004882 Lipase Human genes 0.000 description 7
- 239000004367 Lipase Substances 0.000 description 7
- 108090001060 Lipase Proteins 0.000 description 7
- 235000019421 lipase Nutrition 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000007017 scission Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RJDHDCLWRJEPEJ-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 4-hydroxyundecanoate Chemical compound CCCCCCCC(O)CCC(=O)OCC=C(C)CCC=C(C)C RJDHDCLWRJEPEJ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 230000000873 masking effect Effects 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- PRDIIROHTWNJDB-UHFFFAOYSA-N 3-caproyl propionic acid Chemical compound CCCCCC(=O)CCC(O)=O PRDIIROHTWNJDB-UHFFFAOYSA-N 0.000 description 4
- KBWRWCSRYCKEOR-UHFFFAOYSA-N 3-capryl propionic acid Chemical compound CCCCCCCC(=O)CCC(O)=O KBWRWCSRYCKEOR-UHFFFAOYSA-N 0.000 description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000002781 deodorant agent Substances 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 230000035943 smell Effects 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 4
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 3
- BUIQYRMXTZBRTB-UHFFFAOYSA-N 2,6-dimethylheptan-2-yl 4-oxodecanoate Chemical compound CCCCCCC(=O)CCC(=O)OC(C)(C)CCCC(C)C BUIQYRMXTZBRTB-UHFFFAOYSA-N 0.000 description 3
- RRSAEHIIUDIBBP-UHFFFAOYSA-N 3,7-dimethyloct-6-enyl 4-hydroxydecanoate Chemical compound CCCCCCC(O)CCC(=O)OCCC(C)CCC=C(C)C RRSAEHIIUDIBBP-UHFFFAOYSA-N 0.000 description 3
- DYKOVUKKCCKNPX-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl 4-hydroxydecanoate Chemical compound CCCCCCC(O)CCC(=O)OC(C)(C=C)CCC=C(C)C DYKOVUKKCCKNPX-UHFFFAOYSA-N 0.000 description 3
- OHRHGRQFCQDNKD-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl 4-oxodecanoate Chemical compound CCCCCCC(=O)CCC(=O)OC(C)(C=C)CCC=C(C)C OHRHGRQFCQDNKD-UHFFFAOYSA-N 0.000 description 3
- SWXKLOXBUBQJQN-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 4-hydroxynonanoate Chemical compound CCCCCC(O)CCC(=O)OCC=C(C)CCC=C(C)C SWXKLOXBUBQJQN-UHFFFAOYSA-N 0.000 description 3
- MKZHVQSYPRGNAH-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)but-1-enyl 4-hydroxyundecanoate Chemical compound CCCCCCCC(O)CCC(=O)OC=CC(C)C1=CC=CC(C(C)C)=C1 MKZHVQSYPRGNAH-UHFFFAOYSA-N 0.000 description 3
- GMFMSOANCBJHLV-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)but-1-enyl 4-oxoundecanoate Chemical compound CCCCCCCC(=O)CCC(=O)OC=CC(C)C1=CC=CC(C(C)C)=C1 GMFMSOANCBJHLV-UHFFFAOYSA-N 0.000 description 3
- RBSXKAMXVFPTNM-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)but-1-enyl acetate Chemical compound CC(C)C1=CC=CC(C(C)C=COC(C)=O)=C1 RBSXKAMXVFPTNM-UHFFFAOYSA-N 0.000 description 3
- KRGVTRNRRGDYON-UHFFFAOYSA-N 4-oxoundecanoyl chloride Chemical compound CCCCCCCC(=O)CCC(Cl)=O KRGVTRNRRGDYON-UHFFFAOYSA-N 0.000 description 3
- JHJCHCSUEGPIGE-UHFFFAOYSA-N 7,8-Dihydro-alpha-ionone Chemical compound CC(=O)CCC1C(C)=CCCC1(C)C JHJCHCSUEGPIGE-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
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- DFLYYIGQFUGKOM-UHFFFAOYSA-N hex-3-enyl 4-[3-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-enoyloxy]nonanoate Chemical compound CCC=CCCOC(=O)CCC(CCCCC)OC(=O)C=CC1=CC=CC=C1O[Si](C)(C)C(C)(C)C DFLYYIGQFUGKOM-UHFFFAOYSA-N 0.000 description 3
- RBBLRYOHDSHTKL-UHFFFAOYSA-N hex-3-enyl 4-hydroxydecanoate Chemical compound CCCCCCC(O)CCC(=O)OCCC=CCC RBBLRYOHDSHTKL-UHFFFAOYSA-N 0.000 description 3
- JOVQDKYEUSPVHU-UHFFFAOYSA-N hex-3-enyl 4-oxodecanoate Chemical compound CCCCCCC(=O)CCC(=O)OCCC=CCC JOVQDKYEUSPVHU-UHFFFAOYSA-N 0.000 description 3
- BEJDQQMKQCEZFV-UHFFFAOYSA-N hex-3-enyl 4-oxononanoate Chemical compound CCCCCC(=O)CCC(=O)OCCC=CCC BEJDQQMKQCEZFV-UHFFFAOYSA-N 0.000 description 3
- SLGWLOYQWMFQBC-UHFFFAOYSA-N hex-3-enyl 4-oxoundecanoate Chemical compound CCCCCCCC(=O)CCC(=O)OCCC=CCC SLGWLOYQWMFQBC-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
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- 238000003860 storage Methods 0.000 description 3
- CRDAMVZIKSXKFV-YFVJMOTDSA-N (2-trans,6-trans)-farnesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO CRDAMVZIKSXKFV-YFVJMOTDSA-N 0.000 description 2
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- UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 2
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 description 2
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- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
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- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
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- VXCAAKKTVWZQDN-UHFFFAOYSA-N [3-(4-tert-butylphenyl)-2-methylprop-1-enyl] 4-hydroxyundecanoate Chemical compound CCCCCCCC(O)CCC(=O)OC=C(C)CC1=CC=C(C(C)(C)C)C=C1 VXCAAKKTVWZQDN-UHFFFAOYSA-N 0.000 description 2
- OKSBCVBYLPKIGJ-UHFFFAOYSA-N [3-(4-tert-butylphenyl)-2-methylprop-1-enyl] 4-oxoundecanoate Chemical compound CCCCCCCC(=O)CCC(=O)OC=C(C)CC1=CC=C(C(C)(C)C)C=C1 OKSBCVBYLPKIGJ-UHFFFAOYSA-N 0.000 description 2
- DFFGXGLKNGYGOY-UHFFFAOYSA-N [3-(4-tert-butylphenyl)-2-methylprop-1-enyl] acetate Chemical compound CC(=O)OC=C(C)CC1=CC=C(C(C)(C)C)C=C1 DFFGXGLKNGYGOY-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- GNAZJXNDXSFHFY-UHFFFAOYSA-N bis[1-(3,7-dimethylocta-2,6-dienoxy)-1-oxoundecan-4-yl] butanedioate Chemical compound CC(C)=CCCC(C)=CCOC(=O)CCC(CCCCCCC)OC(=O)CCC(=O)OC(CCCCCCC)CCC(=O)OCC=C(C)CCC=C(C)C GNAZJXNDXSFHFY-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
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Classifications
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- 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
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
- A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- 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
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810337 | 1998-04-20 | ||
| EP98810337 | 1998-04-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69933608D1 DE69933608D1 (de) | 2006-11-30 |
| DE69933608T2 true DE69933608T2 (de) | 2007-08-23 |
Family
ID=8236042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69933608T Expired - Fee Related DE69933608T2 (de) | 1998-04-20 | 1999-03-22 | Verbindungen mit geschützten Hydroxylgruppen |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6437150B1 (enExample) |
| EP (2) | EP0952142B1 (enExample) |
| JP (1) | JP2000053613A (enExample) |
| DE (1) | DE69933608T2 (enExample) |
| ES (1) | ES2273468T3 (enExample) |
| SG (1) | SG75160A1 (enExample) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0952142B1 (en) | 1998-04-20 | 2006-10-18 | Givaudan SA | Compounds with protected hydroxy groups |
| EP1167362B1 (en) * | 2000-06-19 | 2005-05-25 | Givaudan SA | Fragance precursors |
| US20020094938A1 (en) | 2000-11-08 | 2002-07-18 | The Procter & Gamble Company | Photo-labile pro-fragrance conjugates |
| US20030125220A1 (en) | 2001-09-11 | 2003-07-03 | The Procter & Gamble Company | Compositions comprising photo-labile perfume delivery systems |
| DE602004029453D1 (de) * | 2003-03-21 | 2010-11-18 | Pho Derma Inc | Auf licht reagierende duftstoffe |
| DE602004024876D1 (de) | 2003-04-14 | 2010-02-11 | Givaudan Sa | Organische verbindungen |
| DE10348062A1 (de) * | 2003-10-16 | 2005-05-19 | Symrise Gmbh & Co. Kg | Kurzkettige Enolester als Riechstoff-Prekursoren |
| US7910769B2 (en) | 2004-09-02 | 2011-03-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7482482B2 (en) | 2004-09-02 | 2009-01-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608732B2 (en) | 2005-03-08 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7608733B2 (en) | 2004-09-02 | 2009-10-27 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7741515B2 (en) * | 2004-09-02 | 2010-06-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7586000B2 (en) | 2004-09-02 | 2009-09-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7390921B2 (en) | 2004-09-02 | 2008-06-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7495125B2 (en) | 2004-09-02 | 2009-02-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692036B2 (en) | 2004-11-29 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7582793B2 (en) | 2004-09-02 | 2009-09-01 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7399882B2 (en) | 2004-09-02 | 2008-07-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7568361B2 (en) | 2004-09-02 | 2009-08-04 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572932B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7692037B2 (en) | 2004-09-02 | 2010-04-06 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7371894B2 (en) | 2004-09-02 | 2008-05-13 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7572936B2 (en) | 2004-09-02 | 2009-08-11 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7563926B2 (en) | 2004-09-02 | 2009-07-21 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7589231B2 (en) | 2004-09-02 | 2009-09-15 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7507857B2 (en) | 2004-09-02 | 2009-03-24 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7381836B2 (en) | 2004-09-02 | 2008-06-03 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7504535B2 (en) | 2004-09-02 | 2009-03-17 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7683210B2 (en) | 2004-09-02 | 2010-03-23 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7361784B2 (en) | 2004-09-02 | 2008-04-22 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US20060116531A1 (en) * | 2004-11-29 | 2006-06-01 | Wonders Alan G | Modeling of liquid-phase oxidation |
| US7884232B2 (en) | 2005-06-16 | 2011-02-08 | Eastman Chemical Company | Optimized liquid-phase oxidation |
| US7355068B2 (en) | 2006-01-04 | 2008-04-08 | Eastman Chemical Company | Oxidation system with internal secondary reactor |
| US7358389B2 (en) | 2006-01-04 | 2008-04-15 | Eastman Chemical Company | Oxidation system employing internal structure for enhanced hydrodynamics |
| US20070275866A1 (en) * | 2006-05-23 | 2007-11-29 | Robert Richard Dykstra | Perfume delivery systems for consumer goods |
| JP2010518271A (ja) * | 2007-02-09 | 2010-05-27 | ザ プロクター アンド ギャンブル カンパニー | 香料系 |
| US8541401B2 (en) * | 2007-07-25 | 2013-09-24 | Philip Morris Usa Inc. | Flavorant ester salts of polycarboxylic acids and methods for immobilizing and delivering flavorants containing hydroxyl groups |
| EP2362765B1 (en) | 2008-12-01 | 2020-04-08 | The Procter and Gamble Company | Perfume systems |
| US9155772B2 (en) | 2008-12-08 | 2015-10-13 | Philip Morris Usa Inc. | Soft, chewable and orally dissolvable and/or disintegrable products |
| US8754028B2 (en) * | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| US9167835B2 (en) | 2008-12-30 | 2015-10-27 | Philip Morris Usa Inc. | Dissolvable films impregnated with encapsulated tobacco, tea, coffee, botanicals, and flavors for oral products |
| US9167847B2 (en) | 2009-03-16 | 2015-10-27 | Philip Morris Usa Inc. | Production of coated tobacco particles suitable for usage in a smokeless tobacoo product |
| 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 |
| 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 |
| CA2803371C (en) | 2010-07-02 | 2016-04-19 | The Procter & Gamble Company | Process for making films from nonwoven webs |
| EP3533908A1 (en) | 2010-07-02 | 2019-09-04 | The Procter & Gamble Company | Nonwoven web comprising one or more active agents |
| 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. |
| 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 |
| JP6100779B2 (ja) * | 2011-08-24 | 2017-03-22 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | γ−ヒドロキシカルボン酸エステル及びγ−ラクトンの電気化学的生成のための方法 |
| 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 |
| MX353496B (es) | 2012-01-04 | 2018-01-16 | Procter & Gamble | Estructuras fibrosas que contienen activos con múltiples regiones. |
| EP4253649B1 (en) | 2013-12-09 | 2025-04-23 | The Procter & Gamble Company | Fibrous structures including an active agent and having a graphic printed thereon |
| WO2018053356A1 (en) | 2016-09-16 | 2018-03-22 | International Flavors & Fragrances Inc. | Microcapsule compositions stabilized with viscosity control agents |
| BR112018016806B1 (pt) | 2016-02-18 | 2021-11-16 | International Flavors & Fragrances Inc. | Composiqao de microcapsula, e, produtos de consumidor |
| 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 |
| US11697905B2 (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 |
| DE102018002041A1 (de) * | 2017-03-29 | 2018-10-04 | Klüber Lubrication München Se & Co. Kg | Neue Esterverbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| CN112752744B (zh) * | 2018-12-20 | 2025-02-18 | 弗门尼舍有限公司 | 烷基烯醇醚香料前体 |
| 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 |
| KR102726020B1 (ko) * | 2021-11-18 | 2024-11-06 | 주식회사 케이티앤지 | 신규한 향미제, 향미제 조성물 및 이를 포함하는 제품 |
| WO2023090764A1 (ko) * | 2021-11-18 | 2023-05-25 | 주식회사 케이티앤지 | 열에 의해 향미 성분이 방출되는 벽지 조성물 및 벽지 |
| TWI836728B (zh) * | 2021-11-18 | 2024-03-21 | 南韓商韓國煙草人參股份有限公司 | 通過加熱釋放香味成分的壁紙組合物以及壁紙 |
| TWI850852B (zh) * | 2021-11-18 | 2024-08-01 | 南韓商韓國煙草人參股份有限公司 | 包括新型香味劑的吸煙製品 |
| TWI844166B (zh) * | 2021-11-18 | 2024-06-01 | 南韓商韓國煙草人參股份有限公司 | 包括新型香味劑的吸煙製品 |
| CN116648151A (zh) * | 2021-11-18 | 2023-08-25 | 韩国烟草人参公社 | 包括新型香味剂的吸烟制品 |
| KR102774498B1 (ko) * | 2021-11-18 | 2025-03-06 | 주식회사 케이티앤지 | 신규한 향미제를 포함하는 흡연 물품 |
| KR102774489B1 (ko) * | 2021-11-18 | 2025-03-06 | 주식회사 케이티앤지 | 신규한 향미제를 포함하는 흡연 물품 |
| KR102714958B1 (ko) * | 2021-11-18 | 2024-10-14 | 주식회사 케이티앤지 | 신규한 향미제, 향미제 조성물 및 이를 포함하는 제품 |
| KR102766839B1 (ko) * | 2021-11-18 | 2025-02-14 | 주식회사 케이티앤지 | 열에 의해 향미 성분이 방출되는 벽지 조성물 및 벽지 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797217A (en) * | 1957-06-25 | Dihydro oxazine diones | ||
| US2855436A (en) * | 1954-07-26 | 1958-10-07 | Koninklijke Pharma Fab Nv | Production of substituted acrylic acid amides |
| US4218370A (en) | 1979-05-14 | 1980-08-19 | Pennwalt Corporation | Azo monomer useful in polymerization systems |
| DE3568771D1 (en) * | 1984-10-10 | 1989-04-20 | Givaudan & Cie Sa | Hexanoates, process for their preparation and perfumes and/or flavouring agents having a content of such compounds |
| US4830787A (en) | 1987-08-13 | 1989-05-16 | Nabisco Brands, Inc. | Low calorie fat mimetics comprising carboxy/carboxylate esters |
| EP0668904B1 (fr) | 1993-08-09 | 2001-11-07 | Firmenich Sa | Procede de parfumage de textiles |
| CA2176414A1 (en) * | 1995-05-18 | 1996-11-19 | S. David Kimball | Acyl guanidine and amidine prodrugs |
| EP1003469A2 (en) * | 1996-02-21 | 2000-05-31 | Givaudan-Roure (International) S.A. | Fragrance precursors |
| JPH09249683A (ja) | 1996-03-09 | 1997-09-22 | Noguchi Kenkyusho | Ｎ−アセチル−ｄ−ノイラミン酸エステル誘導体、及びその製造法 |
| NZ328102A (en) * | 1996-06-24 | 1998-04-27 | Givaudan Roure Int | Fragrance precursors and deodorant compositions |
| EP0952142B1 (en) | 1998-04-20 | 2006-10-18 | Givaudan SA | Compounds with protected hydroxy groups |
-
1999
- 1999-03-22 EP EP99810249A patent/EP0952142B1/en not_active Expired - Lifetime
- 1999-03-22 EP EP06021602A patent/EP1760067A3/en not_active Withdrawn
- 1999-03-22 ES ES99810249T patent/ES2273468T3/es not_active Expired - Lifetime
- 1999-03-22 DE DE69933608T patent/DE69933608T2/de not_active Expired - Fee Related
- 1999-03-24 SG SG1999001233A patent/SG75160A1/en unknown
- 1999-04-19 JP JP11111199A patent/JP2000053613A/ja active Pending
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2000
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2002
- 2002-06-12 US US10/167,535 patent/US6627763B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SG75160A1 (en) | 2000-09-19 |
| US20020193269A1 (en) | 2002-12-19 |
| EP1760067A3 (en) | 2007-05-30 |
| JP2000053613A (ja) | 2000-02-22 |
| US6627763B2 (en) | 2003-09-30 |
| ES2273468T3 (es) | 2007-05-01 |
| EP1760067A2 (en) | 2007-03-07 |
| EP0952142A1 (en) | 1999-10-27 |
| DE69933608D1 (de) | 2006-11-30 |
| EP0952142B1 (en) | 2006-10-18 |
| US6437150B1 (en) | 2002-08-20 |
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