CA1109078A - Desodorisants - Google Patents

Desodorisants

Info

Publication number: CA1109078A
Authority: CA; Canada
Prior art keywords: carbon atoms; hydrogen; lower alkyl; compound; cyclohexyl
Prior art date: 1975-11-05
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

Application number

CA251,733A

Other languages

English (en)

Inventor

Alfred A. Schleppnik

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bush Boake Allen Inc

Original Assignee

Bush Boake Allen Inc

Priority date (The priority date 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 date listed.)

1975-11-05

Filing date

1976-05-04

Publication date

1981-09-15

1976-05-04 Application filed by Bush Boake Allen Inc filed Critical Bush Boake Allen Inc

1981-09-15 Application granted granted Critical

1981-09-15 Publication of CA1109078A publication Critical patent/CA1109078A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 77
125000000217 alkyl group Chemical group 0.000 claims abstract description 76
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 61
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
239000001257 hydrogen Substances 0.000 claims abstract description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
229910052799 carbon Inorganic materials 0.000 claims abstract description 12
150000002431 hydrogen Chemical class 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 3
235000019645 odor Nutrition 0.000 claims description 49
238000000034 method Methods 0.000 claims description 33
239000000443 aerosol Substances 0.000 claims description 19
MOTUWCAZIYABDQ-UHFFFAOYSA-N 2-cyclohexylpropan-2-yl butanoate Chemical compound CCCC(=O)OC(C)(C)C1CCCCC1 MOTUWCAZIYABDQ-UHFFFAOYSA-N 0.000 claims description 4
MOHLLFDHGGUTMQ-UHFFFAOYSA-N cyclohexylmethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCC1CCCCC1 MOHLLFDHGGUTMQ-UHFFFAOYSA-N 0.000 claims description 4
LLHBKSLMOGXHEF-UHFFFAOYSA-N 2-cyclohexylpropan-2-yl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C1CCCCC1 LLHBKSLMOGXHEF-UHFFFAOYSA-N 0.000 claims description 3
KHSUHPZEMHPXSV-UHFFFAOYSA-N 2-cyclohexylpropan-2-yl formate Chemical compound O=COC(C)(C)C1CCCCC1 KHSUHPZEMHPXSV-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
APEMNGQHJIUHFD-GJHXLRIWSA-N C(C)(=O)OC(C)[C@@H]1CC[C@H](CC1)CC Chemical compound C(C)(=O)OC(C)[C@@H]1CC[C@H](CC1)CC APEMNGQHJIUHFD-GJHXLRIWSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 44
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 39
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 28
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000007788 liquid Substances 0.000 description 23
239000012043 crude product Substances 0.000 description 18
-1 for example Substances 0.000 description 18
239000003205 fragrance Substances 0.000 description 18
239000012267 brine Substances 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000004821 distillation Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000000126 substance Substances 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
230000000694 effects Effects 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
229940022663 acetate Drugs 0.000 description 10
238000012360 testing method Methods 0.000 description 10
239000002808 molecular sieve Substances 0.000 description 9
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 9
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
239000002781 deodorant agent Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
235000013599 spices Nutrition 0.000 description 7
SSZWOQANOUHNLV-UHFFFAOYSA-N 2-cyclohexylpropan-2-ol Chemical compound CC(C)(O)C1CCCCC1 SSZWOQANOUHNLV-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
150000001732 carboxylic acid derivatives Chemical group 0.000 description 6
239000013058 crude material Substances 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
239000002304 perfume Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 5
VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical class OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 5
229910001629 magnesium chloride Inorganic materials 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 4
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000003380 propellant Substances 0.000 description 4
229940090181 propyl acetate Drugs 0.000 description 4
239000007787 solid Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000004338 Dichlorodifluoromethane Substances 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000011368 organic material Substances 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
239000010948 rhodium Substances 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
230000008786 sensory perception of smell Effects 0.000 description 3
239000007921 spray Substances 0.000 description 3
150000003509 tertiary alcohols Chemical class 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
229940029284 trichlorofluoromethane Drugs 0.000 description 3
KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-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
ANCMOAJSZHXJJD-UHFFFAOYSA-N 2-cyclohexylpropan-2-yl acetate Chemical compound CC(=O)OC(C)(C)C1CCCCC1 ANCMOAJSZHXJJD-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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 2
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000220317 Rosa Species 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
SMZMIKZWXNLTNA-UHFFFAOYSA-N cyclohexylmethyl butanoate Chemical compound CCCC(=O)OCC1CCCCC1 SMZMIKZWXNLTNA-UHFFFAOYSA-N 0.000 description 2
ITMPLGUNZXHMGM-UHFFFAOYSA-N cyclohexylmethyl propanoate Chemical compound CCC(=O)OCC1CCCCC1 ITMPLGUNZXHMGM-UHFFFAOYSA-N 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000000499 gel Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 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
230000002045 lasting effect Effects 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
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
238000010419 pet care 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
239000013557 residual solvent Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002453 shampoo Substances 0.000 description 2
ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
238000010998 test method Methods 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
LKMMFRCXXFSDFD-UHFFFAOYSA-N (1-cyclohexyl-2-methylpropyl) acetate Chemical compound CC(=O)OC(C(C)C)C1CCCCC1 LKMMFRCXXFSDFD-UHFFFAOYSA-N 0.000 description 1
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
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-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
HKOKDMODHRUISP-UHFFFAOYSA-N 1-(2-methylcyclohexyl)ethanol Chemical compound CC(O)C1CCCCC1C HKOKDMODHRUISP-UHFFFAOYSA-N 0.000 description 1
YQTZAQCGMZLVSI-UHFFFAOYSA-N 1-(2-methylcyclohexyl)ethyl acetate Chemical compound C(C)(=O)OC(C)C1C(CCCC1)C YQTZAQCGMZLVSI-UHFFFAOYSA-N 0.000 description 1
ADYKWYVGRZVJBC-UHFFFAOYSA-N 1-(3-methylcyclohexyl)ethanol Chemical compound CC(O)C1CCCC(C)C1 ADYKWYVGRZVJBC-UHFFFAOYSA-N 0.000 description 1
NNQGUORFVLRFAY-UHFFFAOYSA-N 1-(4-ethylcyclohexyl)ethanol Chemical compound CCC1CCC(C(C)O)CC1 NNQGUORFVLRFAY-UHFFFAOYSA-N 0.000 description 1
KAUADGCMTGZSPE-UHFFFAOYSA-N 1-(4-methylcyclohexyl)ethanol Chemical compound CC(O)C1CCC(C)CC1 KAUADGCMTGZSPE-UHFFFAOYSA-N 0.000 description 1
WWZFZRBGBOYMOZ-UHFFFAOYSA-N 1-(4-methylcyclohexyl)ethyl butanoate Chemical compound CC1CCC(CC1)C(C)OC(CCC)=O WWZFZRBGBOYMOZ-UHFFFAOYSA-N 0.000 description 1
NEHPIUGJDUWSRR-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanol Chemical compound CC(C)C1CCC(C(C)O)CC1 NEHPIUGJDUWSRR-UHFFFAOYSA-N 0.000 description 1
FTMSYMOBBRINAR-UHFFFAOYSA-N 1-cyclohexylethyl butanoate Chemical compound CCCC(=O)OC(C)C1CCCCC1 FTMSYMOBBRINAR-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
JEALEEGWLFEUOB-UHFFFAOYSA-N 2-cyclohexylpropan-2-yl propanoate Chemical compound CCC(=O)OC(C)(C)C1CCCCC1 JEALEEGWLFEUOB-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
OAFJAALOFJVHMK-UHFFFAOYSA-N 4-cyclohexyl-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)C1CCCCC1 OAFJAALOFJVHMK-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
208000035985 Body Odor Diseases 0.000 description 1
240000007436 Cananga odorata Species 0.000 description 1
241000207199 Citrus Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
208000005156 Dehydration Diseases 0.000 description 1
241000402754 Erythranthe moschata Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 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
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
206010040904 Skin odour abnormal Diseases 0.000 description 1
244000223014 Syzygium aromaticum Species 0.000 description 1
235000016639 Syzygium aromaticum Nutrition 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940062909 amyl salicylate Drugs 0.000 description 1
229940040526 anhydrous sodium acetate 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 class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
235000001053 badasse Nutrition 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000010627 cedar oil Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000019506 cigar Nutrition 0.000 description 1
239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000012459 cleaning agent Substances 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 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
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
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 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000002951 depilatory effect Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
230000032050 esterification Effects 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
239000002979 fabric softener Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
230000037308 hair color Effects 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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000976 ink Substances 0.000 description 1
230000007794 irritation Effects 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
238000004519 manufacturing process Methods 0.000 description 1
230000000873 masking effect Effects 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
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical compound 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
230000001473 noxious effect Effects 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
229920003023 plastic Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000004537 pulping Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003902 salicylic acid esters Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229960005265 selenium sulfide Drugs 0.000 description 1
239000010865 sewage Substances 0.000 description 1
229940074386 skatole Drugs 0.000 description 1
239000000344 soap Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000271 synthetic detergent Substances 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
230000032258 transport Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Emergency Medicine (AREA)
Birds (AREA)
Epidemiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Fats And Perfumes (AREA)

CA251,733A 1975-11-05 1976-05-04 Desodorisants Expired CA1109078A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62885575A	1975-11-05	1975-11-05
US628,855		1975-11-05

Publications (1)

Publication Number	Publication Date
CA1109078A true CA1109078A (fr)	1981-09-15

Family

ID=24520584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA251,733A Expired CA1109078A (fr)	1975-11-05	1976-05-04	Desodorisants

Country Status (11)

Country	Link
JP (1)	JPS6058981B2 (fr)
AU (1)	AU504266B2 (fr)
BE (1)	BE847980A (fr)
BR (1)	BR7607378A (fr)
CA (1)	CA1109078A (fr)
DE (1)	DE2650602C2 (fr)
FR (1)	FR2330666A1 (fr)
GB (1)	GB1545561A (fr)
IL (1)	IL50846A0 (fr)
IT (1)	IT1091557B (fr)
MX (1)	MX146137A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11920104B2 (en)	2018-10-16	2024-03-05	Basf Se	Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2414332A1 (fr) *	1978-01-13	1979-08-10	Unilever Nv	Articles desodorisants a jeter apres usage
FR2414331A1 (fr) *	1978-01-13	1979-08-10	Unilever Nv	Produits desodorisants pour traitement de la peau
US4851050A (en) *	1983-02-16	1989-07-25	Givaudan Corporation	α-campholenic alcohol, dihydro-α-campholenic alcohol and lower acyl esters thereof as tobacco flavorants
US4766002A (en) *	1983-02-16	1988-08-23	Givaudan Corporation	Flavoring with α-campholenic alcohol
DE3474016D1 (en) *	1983-02-16	1988-10-20	Givaudan & Cie Sa	Flavour compositions containing campholenic alcohol or derivatives thereof
CA2232633A1 (fr) *	1995-09-22	1997-03-27	Now 2,000 Limited	Dispositif et procede de neutralisation des mauvaises odeurs
GB9824450D0 (en) *	1998-11-06	1999-01-06	Bush Boake Allen Ltd	Malodour counteractant compositions
JP4520682B2 (ja) *	1999-12-13	2010-08-11	シムライズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツト・ゲゼルシヤフト	臭気中和剤
DE10214675A1 (de) *	2002-04-03	2003-10-16	Haarmann & Reimer Gmbh	Neue alicyclische Ester mit Moschusgeruch
US20040156742A1 (en) *	2003-02-11	2004-08-12	Milan Jolanda Bianca	Synergistically-effective cyclohexylethan-1-yl ester mixtures as malodour counteractants as measured physiologically and psychometrically and methods for using same
US8012554B2 (en)	2007-09-12	2011-09-06	Pactiv Corporation	Bags having odor management capabilities
EP3112448B1 (fr)	2015-06-30	2018-03-21	Symrise AG	Derives d'ethanols 1-(4-methylcyclohexyl)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3847975A (en) *	1966-08-22	1974-11-12	Int Flavors & Fragrances Inc	Perfume compositions containing substituted cyclohexane compounds
GB1254198A (en) *	1969-04-03	1971-11-17	Bush Boake Allen Ltd	ESTERS OF alpha,3,3-TRIMETHYLCYCLOHEXANE METHANOL AND THEIR USE IN PERFUMERY
FR2094264A5 (en) *	1970-06-16	1972-02-04	Lizzani Louisette	Alkyl cyclopentyl ketones and corresponding alcohols in - perfumes and cosmetics

1976
- 1976-05-04 CA CA251,733A patent/CA1109078A/fr not_active Expired
- 1976-11-04 BE BE172075A patent/BE847980A/fr not_active IP Right Cessation
- 1976-11-04 FR FR7633318A patent/FR2330666A1/fr active Granted
- 1976-11-04 BR BR7607378A patent/BR7607378A/pt unknown
- 1976-11-04 IL IL50846A patent/IL50846A0/xx unknown
- 1976-11-04 DE DE2650602A patent/DE2650602C2/de not_active Expired
- 1976-11-04 MX MX166894A patent/MX146137A/es unknown
- 1976-11-04 JP JP51131831A patent/JPS6058981B2/ja not_active Expired
- 1976-11-04 GB GB45884/76A patent/GB1545561A/en not_active Expired
- 1976-11-04 AU AU19293/76A patent/AU504266B2/en not_active Expired
- 1976-11-05 IT IT29092/76A patent/IT1091557B/it active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11920104B2 (en)	2018-10-16	2024-03-05	Basf Se	Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals

Also Published As

Publication number	Publication date
JPS6058981B2 (ja)	1985-12-23
BR7607378A (pt)	1977-09-20
JPS5257328A (en)	1977-05-11
FR2330666B1 (fr)	1983-02-25
AU504266B2 (en)	1979-10-11
FR2330666A1 (fr)	1977-06-03
IT1091557B (it)	1985-07-06
IL50846A0 (en)	1977-01-31
AU1929376A (en)	1978-05-11
DE2650602A1 (de)	1977-05-12
GB1545561A (en)	1979-05-10
DE2650602C2 (de)	1987-03-19
MX146137A (es)	1982-05-19
BE847980A (fr)	1977-05-04

Legal Events

Date	Code	Title	Description
1998-09-15	MKEX	Expiry

Publication	Publication Date	Title
US4187251A (en)	1980-02-05	Malodor counteractants
US4719105A (en)	1988-01-12	Method, compositions and compounds useful in room fresheners employing cyclohexyl alcohol and ester derivatives
US4622221A (en)	1986-11-11	Method, compositions and compounds, useful in room fresheners employing cyclohexyl alcohol and ester derivatives
US4009253A (en)	1977-02-22	4-cyclohexyl-4-methyl-2-pentanone useful as a malodor counteractant
US4310512A (en)	1982-01-12	Derivatives of acetic and propionic acids, compositions containing same and use as malodor counteractants
CA1109078A (fr)	1981-09-15	Desodorisants
CA1108648A (fr)	1981-09-08	Agent de repression de mauvaises odeurs
WO2002085294A2 (fr)	2002-10-31	Utilisation d'acetal a faible masse moleculaire, d'alcool, d'alcool d'acyle et de composes d'esters afin de bloquer ou reduire l'odeur des acides carboxyliques
US3493650A (en)	1970-02-03	Perfume and deodorizing with citronellyl senecioate
EP3362428B1 (fr)	2020-05-06	Nouveaux composés d'octahydro-indènyle propanal
BR102016006550B1 (pt)	2021-09-21	Composto, formulação de fragrância, método para melhorar, realçar ou modificar uma formulação de fragrância, e, produto de fragrância
US20100279917A1 (en)	2010-11-04	Substituted octane(ene) nitriles, methods for the synthesis thereof and uses thereof in perfumery
CA1107201A (fr)	1981-08-18	Desodorisants
US9732304B2 (en)	2017-08-15	3-(cyclohex-1-en-1-yl)propionates and their use in perfume compositions
CA1102349A (fr)	1981-06-02	Traduction non-disponible
CN108203622B (zh)	2022-09-09	感官化合物
US8357810B2 (en)	2013-01-22	3.2.1-bicyclo-octane compounds
CA1041018A (fr)	1978-10-24	Cyclohexyl-4-methyl-4-pentanone-2 emploi comme desodorisant
US11286225B2 (en)	2022-03-29	Organoleptic compounds
CN109485555B (zh)	2021-11-05	新型感官化合物
US8357358B2 (en)	2013-01-22	3.2.1-bicyclo-octane compounds
CN111018680A (zh)	2020-04-17	新型环丙基甲氧基衍生物
US8399522B2 (en)	2013-03-19	3.2.1-bicyclo-octane compounds

CA1109078A - Desodorisants - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=24520584

Family Applications (1)

Country Status (11)

Cited By (1)

Families Citing this family (12)

Family Cites Families (3)

Cited By (1)

Also Published As

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