DE2756050C2 - - Google Patents
Info
- Publication number
- DE2756050C2 DE2756050C2 DE19772756050 DE2756050A DE2756050C2 DE 2756050 C2 DE2756050 C2 DE 2756050C2 DE 19772756050 DE19772756050 DE 19772756050 DE 2756050 A DE2756050 A DE 2756050A DE 2756050 C2 DE2756050 C2 DE 2756050C2
- Authority
- DE
- Germany
- Prior art keywords
- ketone
- cyclohexyl
- smell
- methyl ketone
- unpleasant
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000003205 fragrance Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000000443 aerosol Substances 0.000 claims description 13
- 235000019645 odor Nutrition 0.000 claims description 13
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 claims description 8
- BZJHTOISNZAUIV-UHFFFAOYSA-N 1-(3-methylcyclohexyl)ethanone Chemical compound CC1CCCC(C(C)=O)C1 BZJHTOISNZAUIV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- PNEQETHAGGNHIA-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanone Chemical compound CC(C)C1CCC(C(C)=O)CC1 PNEQETHAGGNHIA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000035943 smell Effects 0.000 description 41
- 239000000243 solution Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 15
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 11
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000001030 gas--liquid chromatography Methods 0.000 description 8
- 239000002781 deodorant agent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002304 perfume Substances 0.000 description 7
- -1 thiophenols Chemical class 0.000 description 7
- 238000002955 isolation Methods 0.000 description 6
- XRLQPWQYUOVNTR-UHFFFAOYSA-N 1-cyclohexyl-2-methylpropan-1-one Chemical compound CC(C)C(=O)C1CCCCC1 XRLQPWQYUOVNTR-UHFFFAOYSA-N 0.000 description 5
- UYMHLXHLPQIDMA-UHFFFAOYSA-N 1-cyclohexylbutan-1-one Chemical compound CCCC(=O)C1CCCCC1 UYMHLXHLPQIDMA-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VZELQXKHIHNPLU-UHFFFAOYSA-N 1-(2-methylcyclohexyl)ethanone Chemical compound CC1CCCCC1C(C)=O VZELQXKHIHNPLU-UHFFFAOYSA-N 0.000 description 4
- HTAYNGUDHFAFFQ-UHFFFAOYSA-N 1-(4-methylcyclohexyl)ethanone Chemical compound CC1CCC(C(C)=O)CC1 HTAYNGUDHFAFFQ-UHFFFAOYSA-N 0.000 description 4
- JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 description 4
- AMHOPTNGSNYSBL-UHFFFAOYSA-N 1-cyclohexylpropan-1-one Chemical compound CCC(=O)C1CCCCC1 AMHOPTNGSNYSBL-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 230000008786 sensory perception of smell Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ICADMAXOJLUEEB-UHFFFAOYSA-N 1-cyclohexylpentan-1-one Chemical compound CCCCC(=O)C1CCCCC1 ICADMAXOJLUEEB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000009423 ventilation Methods 0.000 description 3
- 125000004814 1,1-dimethylethylene group Chemical group [H]C([H])([H])C([*:1])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 2
- AMOVIIVWTHHHTN-UHFFFAOYSA-N 1,3-bis(4-propan-2-ylcyclohexyl)propan-2-one Chemical compound C(C)(C)C1CCC(CC1)CC(=O)CC1CCC(CC1)C(C)C AMOVIIVWTHHHTN-UHFFFAOYSA-N 0.000 description 2
- AWPNHNUSHIWYTJ-UHFFFAOYSA-N 1-(4-ethylcyclohexyl)ethanone Chemical compound CCC1CCC(C(C)=O)CC1 AWPNHNUSHIWYTJ-UHFFFAOYSA-N 0.000 description 2
- DZNUOUOIPRQTTB-UHFFFAOYSA-N 1-cyclohexyl-2-methylpropan-1-ol Chemical compound CC(C)C(O)C1CCCCC1 DZNUOUOIPRQTTB-UHFFFAOYSA-N 0.000 description 2
- MTUCYAOJXPTLHZ-UHFFFAOYSA-N 1-cyclohexylbutan-1-ol Chemical compound CCCC(O)C1CCCCC1 MTUCYAOJXPTLHZ-UHFFFAOYSA-N 0.000 description 2
- OAFJAALOFJVHMK-UHFFFAOYSA-N 4-cyclohexyl-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)C1CCCCC1 OAFJAALOFJVHMK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000017803 cinnamon Nutrition 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- RUHOAHWSRPNSCJ-UHFFFAOYSA-N 1,3-bis(3-methylcyclohexyl)propan-2-one Chemical compound C1C(C)CCCC1CC(=O)CC1CC(C)CCC1 RUHOAHWSRPNSCJ-UHFFFAOYSA-N 0.000 description 1
- HKOKDMODHRUISP-PSGOWDBMSA-N 1-[(1r,2r)-2-methylcyclohexyl]ethanol Chemical compound CC(O)[C@@H]1CCCC[C@H]1C HKOKDMODHRUISP-PSGOWDBMSA-N 0.000 description 1
- PKXSPCMDZCKLCI-UHFFFAOYSA-N 1-cyclohexylpentan-1-ol Chemical compound CCCCC(O)C1CCCCC1 PKXSPCMDZCKLCI-UHFFFAOYSA-N 0.000 description 1
- JVTXOMXEPFDMHB-UHFFFAOYSA-N 1-cyclohexylpropan-1-ol Chemical compound CCC(O)C1CCCCC1 JVTXOMXEPFDMHB-UHFFFAOYSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 description 1
- KMXGUADJSORMAM-UHFFFAOYSA-N 3-methyl-1-(4-methylcyclohexyl)butan-1-one Chemical compound CC(C)CC(=O)C1CCC(C)CC1 KMXGUADJSORMAM-UHFFFAOYSA-N 0.000 description 1
- XMTVYEAPWJCZBS-UHFFFAOYSA-N 4,6-dicyclohexylnonan-5-one Chemical compound C1(CCCCC1)C(CCC)C(=O)C(CCC)C1CCCCC1 XMTVYEAPWJCZBS-UHFFFAOYSA-N 0.000 description 1
- MVDPTWHTUYDLTL-UHFFFAOYSA-N 4-Methylphenyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC1=CC=C(C)C=C1 MVDPTWHTUYDLTL-UHFFFAOYSA-N 0.000 description 1
- NEHPIUGJDUWSRR-JQTAXMAWSA-N C(C)(C)[C@@H]1CC[C@H](CC1)C(C)O Chemical compound C(C)(C)[C@@H]1CC[C@H](CC1)C(C)O NEHPIUGJDUWSRR-JQTAXMAWSA-N 0.000 description 1
- NNQGUORFVLRFAY-PHAYGUFNSA-N CC[C@H]1CC[C@@H](CC1)C(C)O Chemical compound CC[C@H]1CC[C@@H](CC1)C(C)O NNQGUORFVLRFAY-PHAYGUFNSA-N 0.000 description 1
- KAUADGCMTGZSPE-AGALZMSESA-N C[C@@H]1CC[C@H](CC1)C(C)O Chemical compound C[C@@H]1CC[C@H](CC1)C(C)O KAUADGCMTGZSPE-AGALZMSESA-N 0.000 description 1
- ADYKWYVGRZVJBC-SMOXQLQSSA-N C[C@@H]1C[C@H](CCC1)C(C)O Chemical compound C[C@@H]1C[C@H](CCC1)C(C)O ADYKWYVGRZVJBC-SMOXQLQSSA-N 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- AWPNHNUSHIWYTJ-MGCOHNPYSA-N O=C([C@H]1CC[C@@H](CC1)CC)C Chemical compound O=C([C@H]1CC[C@@H](CC1)CC)C AWPNHNUSHIWYTJ-MGCOHNPYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940062909 amyl salicylate Drugs 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 235000001053 badasse Nutrition 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical class OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- 230000002951 depilatory effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229940095045 isopulegol Drugs 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical group CC1=C(N(=O)=O)C(C)=C(N(=O)=O)C(C(C)(C)C)=C1N(=O)=O XMWRWTSZNLOZFN-UHFFFAOYSA-N 0.000 description 1
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75177376A | 1976-12-16 | 1976-12-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2756050A1 DE2756050A1 (de) | 1978-06-29 |
| DE2756050C2 true DE2756050C2 (enrdf_load_stackoverflow) | 1988-06-23 |
Family
ID=25023416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772756050 Granted DE2756050A1 (de) | 1976-12-16 | 1977-12-15 | Praeparate zur geruchsverbesserung |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS6044937B2 (enrdf_load_stackoverflow) |
| AU (1) | AU517438B2 (enrdf_load_stackoverflow) |
| BR (1) | BR7708361A (enrdf_load_stackoverflow) |
| CA (1) | CA1102349A (enrdf_load_stackoverflow) |
| DE (1) | DE2756050A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2374046A1 (enrdf_load_stackoverflow) |
| GB (2) | GB1590485A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3517106A1 (de) * | 1985-05-11 | 1986-11-13 | Basf Ag, 6700 Ludwigshafen | Cyclohexanderivate |
| US5256405A (en) * | 1991-12-30 | 1993-10-26 | Tom's Of Maine | Herbal deodorant |
| US5260053A (en) * | 1991-12-30 | 1993-11-09 | Tom's Of Maine | Herbal deodorant |
| US8012554B2 (en) | 2007-09-12 | 2011-09-06 | Pactiv Corporation | Bags having odor management capabilities |
| US20230151161A1 (en) * | 2020-04-09 | 2023-05-18 | Tyromer Inc. | Method and system for odour abatement in rubber processing |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1105455A (en) * | 1963-11-05 | 1968-03-06 | Int Flavors & Fragrances Inc | Aryl and cyclohexyl alkanones |
| US3847975A (en) * | 1966-08-22 | 1974-11-12 | Int Flavors & Fragrances Inc | Perfume compositions containing substituted cyclohexane compounds |
| JPS5077547A (enrdf_load_stackoverflow) * | 1973-11-05 | 1975-06-24 | ||
| CH617648A5 (en) * | 1975-02-12 | 1980-06-13 | Givaudan & Cie Sa | Process for the preparation of substituted cyclohexanes. |
-
1977
- 1977-12-15 BR BR7708361A patent/BR7708361A/pt unknown
- 1977-12-15 AU AU31604/77A patent/AU517438B2/en not_active Expired
- 1977-12-15 DE DE19772756050 patent/DE2756050A1/de active Granted
- 1977-12-15 CA CA293,182A patent/CA1102349A/en not_active Expired
- 1977-12-15 GB GB5218977A patent/GB1590485A/en not_active Expired
- 1977-12-15 JP JP52149982A patent/JPS6044937B2/ja not_active Expired
- 1977-12-15 GB GB2062279A patent/GB1590486A/en not_active Expired
- 1977-12-15 FR FR7737854A patent/FR2374046A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU517438B2 (en) | 1981-07-30 |
| BR7708361A (pt) | 1978-08-15 |
| DE2756050A1 (de) | 1978-06-29 |
| FR2374046A1 (fr) | 1978-07-13 |
| GB1590486A (en) | 1981-06-03 |
| JPS5375336A (en) | 1978-07-04 |
| JPS6044937B2 (ja) | 1985-10-07 |
| AU3160477A (en) | 1979-06-21 |
| CA1102349A (en) | 1981-06-02 |
| GB1590485A (en) | 1981-06-03 |
| FR2374046B1 (enrdf_load_stackoverflow) | 1983-03-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4187251A (en) | Malodor counteractants | |
| US4719105A (en) | Method, compositions and compounds useful in room fresheners employing cyclohexyl alcohol and ester derivatives | |
| US4622221A (en) | Method, compositions and compounds, useful in room fresheners employing cyclohexyl alcohol and ester derivatives | |
| EP0303212B1 (de) | Desodorantien, ihre Herstellung und Verwendung | |
| DE69405350T2 (de) | Aromatische verbindungen und ihre anwendung in der parfümerie | |
| DE69018685T2 (de) | Aromatische Aldehyde, ihre Derivate und ihre Verwendung als Bestandteil in Riechstoffen, Herbiziden und Fungiziden. | |
| DE2650602C2 (de) | Verwendung von Cyclohexylalkanolestern als Desodorierungsmittel | |
| DE2656405A1 (de) | Mittel und verfahren zur bekaempfung von ueblen geruechen | |
| DE1593662A1 (de) | Verfahren zur Herstellung von Citronellylsenecioat und dieses enthaltender Parfuemerie- und kosmetischer Produkte | |
| DE1593662C (enrdf_load_stackoverflow) | ||
| DE2756050C2 (enrdf_load_stackoverflow) | ||
| DE69717612T2 (de) | Parfümierte makrozyklische laktone | |
| CH626805A5 (enrdf_load_stackoverflow) | ||
| EP3362428A1 (en) | Novel octahydroindenyl propanal compounds | |
| DE2737525C3 (de) | Verwendung von Tricyclo-[6,2,1,O↑2↑]-und ec-9-en-3-on in Riechstoffen | |
| DE2826841A1 (de) | Mittel zur geruchsbekaempfung | |
| DE60200407T2 (de) | Methylendioxy- Derivate | |
| DE60209664T2 (de) | Duftstoffzusammensetzung enthaltend 3-(3-Hexenyl)-2-Cyclopentenon | |
| DE602005005275T2 (de) | Hexahydro-4H-Indeno Acetonidverbindung als Duftstoff | |
| DE69507382T2 (de) | Verwendung einer alkylsubstituierter Pyridine als Riechstoff | |
| EP0098791A1 (de) | 2-Methylpentansäureester mit verzweigtem oder carbocyclischem Alkoholrest, deren Herstellung und Verwendung als Riechstoffe | |
| EP0291849B1 (de) | 4-Methyl-4-phenyl-1-pentanale, deren Herstellung und Verwendung als Riechstoffe | |
| DE2452212A1 (de) | Praeparate zur geruchsverbesserung | |
| DE69804294T2 (de) | Cycloalkylether und sie enthaltende Riechstoffzusammensetzungen | |
| DE602005005206T2 (de) | Ungesättigte ether als parfümstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8128 | New person/name/address of the agent |
Representative=s name: BERENDT, T., DIPL.-CHEM. DR., PAT.-ANW., 8000 MUEN |
|
| 8128 | New person/name/address of the agent |
Representative=s name: SCHMIED-KOWARZIK, V., DR., 8000 MUENCHEN DANNENBER |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |