CA1108648A - Malodor counteractants - Google Patents

Malodor counteractants

Info

Publication number: CA1108648A
Authority: CA; Canada
Prior art keywords: cis; trans; ethanol; malodor counteractant; malodor
Prior art date: 1975-12-15
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

CA252,710A

Other languages

English (en)

French (fr)

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.)

1975-12-15

Filing date

1976-05-17

Publication date

1981-09-08

1976-05-17 Application filed by Bush Boake Allen Inc filed Critical Bush Boake Allen Inc

1981-09-08 Application granted granted Critical

1981-09-08 Publication of CA1108648A publication Critical patent/CA1108648A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 57
239000000203 mixture Substances 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
150000002431 hydrogen Chemical class 0.000 claims abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
235000019645 odor Nutrition 0.000 claims description 21
239000003205 fragrance Substances 0.000 claims description 15
239000000443 aerosol Substances 0.000 claims description 14
SSZWOQANOUHNLV-UHFFFAOYSA-N 2-cyclohexylpropan-2-ol Chemical compound CC(C)(O)C1CCCCC1 SSZWOQANOUHNLV-UHFFFAOYSA-N 0.000 claims description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 19
239000000047 product Substances 0.000 description 18
-1 for example Substances 0.000 description 14
229960004592 isopropanol Drugs 0.000 description 14
230000000875 corresponding effect Effects 0.000 description 13
239000000126 substance Substances 0.000 description 12
229940076134 benzene Drugs 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
239000002781 deodorant agent Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 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
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 6
239000012141 concentrate Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229960002337 magnesium chloride Drugs 0.000 description 5
229910001629 magnesium chloride Inorganic materials 0.000 description 5
235000011147 magnesium chloride Nutrition 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
235000013599 spices Nutrition 0.000 description 5
KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
QTDXSEZXAPHVBI-UHFFFAOYSA-N 4-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)CC1 QTDXSEZXAPHVBI-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical class OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
239000010948 rhodium Substances 0.000 description 3
230000008786 sensory perception of smell Effects 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
150000003509 tertiary alcohols Chemical class 0.000 description 3
OSINZLLLLCUKJH-UHFFFAOYSA-N 4-methylcyclohexanemethanol Chemical group CC1CCC(CO)CC1 OSINZLLLLCUKJH-UHFFFAOYSA-N 0.000 description 2
YRQKWRUZZCBSIG-UHFFFAOYSA-N 4-propan-2-ylcyclohexane-1-carboxylic acid Chemical compound CC(C)C1CCC(C(O)=O)CC1 YRQKWRUZZCBSIG-UHFFFAOYSA-N 0.000 description 2
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000499 gel 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
239000010410 layer Substances 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
239000012044 organic layer Substances 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
239000003380 propellant Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002453 shampoo Substances 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-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
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
NNQGUORFVLRFAY-UHFFFAOYSA-N 1-(4-ethylcyclohexyl)ethanol Chemical class CCC1CCC(C(C)O)CC1 NNQGUORFVLRFAY-UHFFFAOYSA-N 0.000 description 1
PDLCCNYKIIUWHA-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)ethanone Chemical compound CC(C)C1=CC=C(C(C)=O)C=C1 PDLCCNYKIIUWHA-UHFFFAOYSA-N 0.000 description 1
DZNUOUOIPRQTTB-UHFFFAOYSA-N 1-cyclohexyl-2-methylpropan-1-ol Chemical compound CC(C)C(O)C1CCCCC1 DZNUOUOIPRQTTB-UHFFFAOYSA-N 0.000 description 1
PKXSPCMDZCKLCI-UHFFFAOYSA-N 1-cyclohexylpentan-1-ol Chemical compound CCCCC(O)C1CCCCC1 PKXSPCMDZCKLCI-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
MGEBVSZZNFOIRB-UHFFFAOYSA-N 2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(I)=NC=2N1C1OC(CO)C(O)C1O MGEBVSZZNFOIRB-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
208000035985 Body Odor Diseases 0.000 description 1
240000007436 Cananga odorata Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
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
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000220317 Rosa Species 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
239000002253 acid Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
150000001299 aldehydes 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
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-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
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 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
229940007550 benzyl acetate Drugs 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910052799 carbon Inorganic materials 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
235000019506 cigar Nutrition 0.000 description 1
239000001111 citrus aurantium l. leaf oil Substances 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
239000013058 crude material 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
239000000645 desinfectant Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003599 detergent 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
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
239000000975 dye Substances 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
239000000284 extract Substances 0.000 description 1
239000002979 fabric softener Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 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
238000002329 infrared spectrum Methods 0.000 description 1
239000000976 ink Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
230000000670 limiting effect Effects 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
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 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
230000007935 neutral effect Effects 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000003884 phenylalkyl group Chemical group 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
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
230000028327 secretion Effects 0.000 description 1
229960005265 selenium sulfide Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010865 sewage Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000271 synthetic detergent 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
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
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
- A61K8/34—Alcohols
- 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
- 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
- A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
- 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

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Birds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Fats And Perfumes (AREA)

CA252,710A 1975-12-15 1976-05-17 Malodor counteractants Expired CA1108648A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US64061475A	1975-12-15	1975-12-15
US640,614		1975-12-15

Publications (1)

Publication Number	Publication Date
CA1108648A true CA1108648A (en)	1981-09-08

Family

ID=24568971

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA252,710A Expired CA1108648A (en)	1975-12-15	1976-05-17	Malodor counteractants

Country Status (10)

Country	Link
JP (1)	JPS607495B2 (it)
AR (1)	AR218440A1 (it)
AU (1)	AU506507B2 (it)
BR (1)	BR7608361A (it)
CA (1)	CA1108648A (it)
DE (1)	DE2656405A1 (it)
FR (1)	FR2335244A1 (it)
GB (2)	GB1545563A (it)
IT (1)	IT1121748B (it)
MX (1)	MX146138A (it)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH617648A5 (en) *	1975-02-12	1980-06-13	Givaudan & Cie Sa	Process for the preparation of substituted cyclohexanes.
US4181631A (en)	1975-02-12	1980-01-01	Givaudan Corporation	Alpha-hydroxyalkyl-4-tertiary-alkylcyclohexane perfume compositions
CH637612A5 (en) *	1977-02-01	1983-08-15	Givaudan & Cie Sa	Substituted cyclohexanes
EP0116903B1 (en) *	1983-02-16	1988-09-14	L. GIVAUDAN & CIE Société Anonyme	Flavour compositions containing campholenic alcohol or derivatives thereof
US4766002A (en) *	1983-02-16	1988-08-23	Givaudan Corporation	Flavoring with α-campholenic alcohol
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
DE3517106A1 (de) *	1985-05-11	1986-11-13	Basf Ag, 6700 Ludwigshafen	Cyclohexanderivate
DE3537228A1 (de) *	1985-10-19	1987-04-23	Huels Chemische Werke Ag	Verfahren zur herstellung von cyclohexylverbindungen
GB9824450D0 (en) *	1998-11-06	1999-01-06	Bush Boake Allen Ltd	Malodour counteractant compositions
JP5441526B2 (ja) *	2009-07-01	2014-03-12	三菱瓦斯化学株式会社	脂環式アルコールの製造方法
WO2017146182A2 (en) *	2016-02-24	2017-08-31	Takasago International Corporation	Household product delivering warming and/or tingling sensations
DE102016225562A1 (de)	2016-12-20	2018-06-21	Henkel Ag & Co. Kgaa	"Kosmetische Mittel mit verbesserter Wirkung gegen Körpergeruch"
EP4692289A4 (en) *	2023-03-31	2026-07-15	Mitsubishi Gas Chemical Co	PERFUME COMPOSITION AND ALICYCLIC ALCOHOL COMPOSITION

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DE1106761B (de) *	1959-05-29	1961-05-18	Rhone Poulenc Sa	Verfahren zur Herstellung von Cyclohexylaethylalkohol
US3847975A (en) *	1966-08-22	1974-11-12	Int Flavors & Fragrances Inc	Perfume compositions containing substituted cyclohexane compounds
CH578312A5 (it) *	1973-06-07	1976-08-13	Firmenich & Cie
CH617648A5 (en) *	1975-02-12	1980-06-13	Givaudan & Cie Sa	Process for the preparation of substituted cyclohexanes.

1976
- 1976-05-17 CA CA252,710A patent/CA1108648A/en not_active Expired
- 1976-12-13 FR FR7637506A patent/FR2335244A1/fr active Granted
- 1976-12-13 AU AU20492/76A patent/AU506507B2/en not_active Expired
- 1976-12-13 GB GB65578A patent/GB1545563A/en not_active Expired
- 1976-12-13 BR BR7608361A patent/BR7608361A/pt unknown
- 1976-12-13 JP JP51148822A patent/JPS607495B2/ja not_active Expired
- 1976-12-13 AR AR26581676A patent/AR218440A1/es active
- 1976-12-13 IT IT3035976A patent/IT1121748B/it active
- 1976-12-13 DE DE19762656405 patent/DE2656405A1/de not_active Ceased
- 1976-12-13 MX MX16738476A patent/MX146138A/es unknown
- 1976-12-13 GB GB5186976A patent/GB1545562A/en not_active Expired

Also Published As

Publication number	Publication date
JPS5272826A (en)	1977-06-17
AR218440A1 (es)	1980-06-13
MX146138A (es)	1982-05-19
DE2656405A1 (de)	1977-06-16
GB1545562A (en)	1979-05-10
AU2049276A (en)	1978-06-22
GB1545563A (en)	1979-05-10
FR2335244A1 (fr)	1977-07-15
BR7608361A (pt)	1977-12-13
FR2335244B1 (it)	1980-06-20
AU506507B2 (en)	1980-01-10
JPS607495B2 (ja)	1985-02-25
IT1121748B (it)	1986-04-23

Legal Events

Date	Code	Title	Description
1998-09-08	MKEX	Expiry

Publication	Publication Date	Title
US4187251A (en)	1980-02-05	Malodor counteractants
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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
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CA1041018A (en)	1978-10-24	4-cyclohexyl-4-methyl-2-pentanone as deodorants
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WO2021247824A1 (en)	2021-12-09	Profragrance conjugates
US8357358B2 (en)	2013-01-22	3.2.1-bicyclo-octane compounds
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