CA1041016A - Process of suppressing odors employing deodorants containing esters of citric acid - Google Patents
Process of suppressing odors employing deodorants containing esters of citric acidInfo
- Publication number
- CA1041016A CA1041016A CA223,608A CA223608A CA1041016A CA 1041016 A CA1041016 A CA 1041016A CA 223608 A CA223608 A CA 223608A CA 1041016 A CA1041016 A CA 1041016A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- spray
- acid
- citric acid
- alcohol
- 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 239000002781 deodorant agent Substances 0.000 title claims abstract description 36
- 150000002148 esters Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 13
- 235000019645 odor Nutrition 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- VXRUADVCBZMFSV-UHFFFAOYSA-N 2-acetyloxypropane-1,2,3-tricarboxylic acid Chemical compound CC(=O)OC(CC(O)=O)(CC(O)=O)C(O)=O VXRUADVCBZMFSV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002537 cosmetic Substances 0.000 claims abstract description 14
- 208000035985 Body Odor Diseases 0.000 claims abstract description 13
- 206010040904 Skin odour abnormal Diseases 0.000 claims abstract description 13
- -1 citrate ester Chemical class 0.000 claims description 17
- 239000003380 propellant Substances 0.000 claims description 10
- 230000001877 deodorizing effect Effects 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000008406 cosmetic ingredient Substances 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 abstract description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 229960004063 propylene glycol Drugs 0.000 description 8
- 235000013772 propylene glycol Nutrition 0.000 description 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 5
- JBGDSVVIBTXYJD-UHFFFAOYSA-N 2-hydroxy-4-oxopentane-1,2,3-tricarboxylic acid Chemical class CC(=O)C(C(O)=O)C(O)(C(O)=O)CC(O)=O JBGDSVVIBTXYJD-UHFFFAOYSA-N 0.000 description 4
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 4
- 239000001069 triethyl citrate Substances 0.000 description 4
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 4
- 235000013769 triethyl citrate Nutrition 0.000 description 4
- HDDLVZWGOPWKFW-UHFFFAOYSA-N trimethyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound COC(=O)CC(O)(C(=O)OC)CC(=O)OC HDDLVZWGOPWKFW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001166 anti-perspirative effect Effects 0.000 description 3
- 239000003213 antiperspirant Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- OMPIYDSYGYKWSG-UHFFFAOYSA-N 2-(2-ethoxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 2
- WWXUGNUFCNYMFK-UHFFFAOYSA-N Acetyl citrate Chemical compound CC(=O)OC(=O)CC(O)(C(O)=O)CC(O)=O WWXUGNUFCNYMFK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 2
- ZLZAOJXNPKEAQD-UHFFFAOYSA-N tripropyl 2-hydroxy-4-oxopentane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)C(C(C)=O)C(=O)OCCC ZLZAOJXNPKEAQD-UHFFFAOYSA-N 0.000 description 2
- SKHXHUZZFVMERR-UHFFFAOYSA-N 1-Isopropyl citrate Chemical compound CC(C)OC(=O)CC(O)(C(O)=O)CC(O)=O SKHXHUZZFVMERR-UHFFFAOYSA-N 0.000 description 1
- JBPAHOHMBWCZMH-UHFFFAOYSA-N 2-(1,3-dioxo-1-pentoxybutan-2-yl)-2-hydroxybutanedioic acid Chemical compound CCCCCOC(=O)C(C(=O)C)C(CC(=O)O)(C(=O)O)O JBPAHOHMBWCZMH-UHFFFAOYSA-N 0.000 description 1
- RGCFHPQKUUASEK-UHFFFAOYSA-N 2-(1,3-dioxo-1-propoxybutan-2-yl)-2-hydroxybutanedioic acid Chemical compound CCCOC(=O)C(C(C)=O)C(O)(C(O)=O)CC(O)=O RGCFHPQKUUASEK-UHFFFAOYSA-N 0.000 description 1
- IRJWFTAFEWYAAQ-UHFFFAOYSA-N 2-(1-butoxy-1,3-dioxobutan-2-yl)-2-hydroxybutanedioic acid Chemical compound CCCCOC(=O)C(C(C)=O)C(O)(C(O)=O)CC(O)=O IRJWFTAFEWYAAQ-UHFFFAOYSA-N 0.000 description 1
- WCLCAMKFJKKBCJ-UHFFFAOYSA-N 2-(1-cyclohexyloxy-1,3-dioxobutan-2-yl)-2-hydroxybutanedioic acid Chemical compound OC(=O)CC(O)(C(O)=O)C(C(=O)C)C(=O)OC1CCCCC1 WCLCAMKFJKKBCJ-UHFFFAOYSA-N 0.000 description 1
- ZUTRZLBAFUBAFK-UHFFFAOYSA-N 2-(1-ethoxy-1,3-dioxobutan-2-yl)-2-hydroxybutanedioic acid Chemical compound CCOC(=O)C(C(C)=O)C(O)(C(O)=O)CC(O)=O ZUTRZLBAFUBAFK-UHFFFAOYSA-N 0.000 description 1
- TWUZWTIVCCRAAD-UHFFFAOYSA-N 2-(2-butoxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound CCCCOC(=O)CC(O)(C(O)=O)CC(O)=O TWUZWTIVCCRAAD-UHFFFAOYSA-N 0.000 description 1
- JHZLLXXZMYEPHT-UHFFFAOYSA-N 2-(2-cyclohexyloxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(=O)OC1CCCCC1 JHZLLXXZMYEPHT-UHFFFAOYSA-N 0.000 description 1
- WMYIFEPOLLNNBZ-UHFFFAOYSA-N 2-(2-hexoxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound CCCCCCOC(=O)CC(O)(C(O)=O)CC(O)=O WMYIFEPOLLNNBZ-UHFFFAOYSA-N 0.000 description 1
- YUTUUOJFXIMELV-UHFFFAOYSA-N 2-Hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid Chemical compound COC(=O)CC(O)(C(O)=O)CC(O)=O YUTUUOJFXIMELV-UHFFFAOYSA-N 0.000 description 1
- APRGCWHNRUOQIM-UHFFFAOYSA-N 2-hydroxy-2-(1-methoxy-1,3-dioxobutan-2-yl)butanedioic acid Chemical compound COC(=O)C(C(C)=O)C(O)(C(O)=O)CC(O)=O APRGCWHNRUOQIM-UHFFFAOYSA-N 0.000 description 1
- IPXGDGHVANPYRW-UHFFFAOYSA-N 2-hydroxy-2-(2-oxo-2-pentoxyethyl)butanedioic acid Chemical compound CCCCCOC(=O)CC(O)(C(O)=O)CC(O)=O IPXGDGHVANPYRW-UHFFFAOYSA-N 0.000 description 1
- MHUXGBAKULUKLC-UHFFFAOYSA-N 2-hydroxy-4-oxo-2-(2-oxo-2-propan-2-yloxyethyl)-4-propan-2-yloxybutanoic acid Chemical compound CC(C)OC(=O)CC(O)(C(O)=O)CC(=O)OC(C)C MHUXGBAKULUKLC-UHFFFAOYSA-N 0.000 description 1
- XSUPXKHTYKPZKM-UHFFFAOYSA-N 2-hydroxy-4-oxo-2-(2-oxo-2-propoxyethyl)-4-propoxybutanoic acid Chemical compound CCCOC(=O)CC(O)(C(O)=O)CC(=O)OCCC XSUPXKHTYKPZKM-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- OMIHCBSQSYMFDP-UHFFFAOYSA-N 3-hydroxy-5-methoxy-3-methoxycarbonyl-5-oxopentanoic acid Chemical compound COC(=O)CC(O)(CC(O)=O)C(=O)OC OMIHCBSQSYMFDP-UHFFFAOYSA-N 0.000 description 1
- XRCRWCVBMHENNE-UHFFFAOYSA-N 4-butoxy-2-(2-butoxy-2-oxoethyl)-2-hydroxy-4-oxobutanoic acid Chemical compound CCCCOC(=O)CC(O)(C(O)=O)CC(=O)OCCCC XRCRWCVBMHENNE-UHFFFAOYSA-N 0.000 description 1
- WLNOQGJLHQXWJO-UHFFFAOYSA-N 4-cyclohexyloxy-2-(2-cyclohexyloxy-2-oxoethyl)-2-hydroxy-4-oxobutanoic acid Chemical compound C1CCCCC1OC(=O)CC(O)(C(=O)O)CC(=O)OC1CCCCC1 WLNOQGJLHQXWJO-UHFFFAOYSA-N 0.000 description 1
- DXSLNXVLJIGITN-UHFFFAOYSA-N CC(C)OC(=O)CC(O)(C(O)=O)C(C(C)=O)C(=O)OC(C)C Chemical compound CC(C)OC(=O)CC(O)(C(O)=O)C(C(C)=O)C(=O)OC(C)C DXSLNXVLJIGITN-UHFFFAOYSA-N 0.000 description 1
- RQVMDYBZZZBWRX-UHFFFAOYSA-N CCCCCCOC(=O)CC(O)(C(O)=O)C(C(C)=O)C(=O)OCCCCCC Chemical compound CCCCCCOC(=O)CC(O)(C(O)=O)C(C(C)=O)C(=O)OCCCCCC RQVMDYBZZZBWRX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- PESZCXUNMKAYME-UHFFFAOYSA-N Citroflex A-4 Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)C(C(C)=O)C(=O)OCCCC PESZCXUNMKAYME-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- VQENOYXMFIFHCY-UHFFFAOYSA-N Monoglyceride citrate Chemical compound OCC(O)COC(=O)CC(O)(C(O)=O)CC(O)=O VQENOYXMFIFHCY-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241001201614 Prays Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- SVRNCUQFNOBJLH-UHFFFAOYSA-N tricyclohexyl 2-hydroxy-4-oxopentane-1,2,3-tricarboxylate Chemical compound C1CCCCC1OC(=O)CC(O)(C(=O)OC1CCCCC1)C(C(=O)C)C(=O)OC1CCCCC1 SVRNCUQFNOBJLH-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- WBBUYACCVIYKCV-UHFFFAOYSA-N triethyl 2-hydroxy-4-oxopentane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)C(C(C)=O)C(=O)OCC WBBUYACCVIYKCV-UHFFFAOYSA-N 0.000 description 1
- TUUQISRYLMFKOG-UHFFFAOYSA-N trihexyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCOC(=O)CC(C(=O)OCCCCCC)(OC(C)=O)CC(=O)OCCCCCC TUUQISRYLMFKOG-UHFFFAOYSA-N 0.000 description 1
- AMMPRZCMKXDUNE-UHFFFAOYSA-N trihexyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCOC(=O)CC(O)(C(=O)OCCCCCC)CC(=O)OCCCCCC AMMPRZCMKXDUNE-UHFFFAOYSA-N 0.000 description 1
- DXRFOGXSSDRZFP-UHFFFAOYSA-N tripentyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCOC(=O)CC(O)(C(=O)OCCCCC)CC(=O)OCCCCC DXRFOGXSSDRZFP-UHFFFAOYSA-N 0.000 description 1
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/05—Stick
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)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2418338A DE2418338B2 (de) | 1974-04-16 | 1974-04-16 | Verwendung von Estern der Citronensäure und/oder Acetylcitronensäure in wasserfreien kosmetischen Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1041016A true CA1041016A (en) | 1978-10-24 |
Family
ID=5913053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA223,608A Expired CA1041016A (en) | 1974-04-16 | 1975-04-02 | Process of suppressing odors employing deodorants containing esters of citric acid |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4010253A (en, 2012) |
| AR (1) | AR204576A1 (en, 2012) |
| AT (1) | AT332978B (en, 2012) |
| BE (1) | BE827906A (en, 2012) |
| CA (1) | CA1041016A (en, 2012) |
| CH (1) | CH595839A5 (en, 2012) |
| DE (1) | DE2418338B2 (en, 2012) |
| FR (1) | FR2267756B1 (en, 2012) |
| GB (1) | GB1453266A (en, 2012) |
| IT (1) | IT1034973B (en, 2012) |
| NL (1) | NL7503336A (en, 2012) |
| SE (1) | SE403567B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1589866A (en) * | 1976-08-20 | 1981-05-20 | Unilever Ltd | Detergent bars for personal washing |
| US4120948A (en) * | 1976-11-29 | 1978-10-17 | The Procter & Gamble Company | Two phase antiperspirant compositions |
| DE2826757A1 (de) * | 1978-06-19 | 1979-12-20 | Henkel Kgaa | Verwendung einer kombination von adstringierenden sauren aluminiumsalzen mit estern der citronensaeure, acetylcitronensaeure, ein- und zweibasischer aliphatischer hydroxycarbonsaeuren und antioxidantien als deodorantien |
| DE2826758A1 (de) * | 1978-06-19 | 1979-12-20 | Henkel Kgaa | Verwendung einer kombination von estern der citronensaeure und/oder acetylcitronensaeure mit antioxidantien als deodorantien |
| DE2834645A1 (de) * | 1978-08-08 | 1980-02-28 | Basf Ag | Verwendung von citronensaeureestern in kosmetischen zubereitungen |
| DE3030920A1 (de) * | 1980-08-16 | 1982-04-22 | Henkel KGaA, 4000 Düsseldorf | Sanitaere hygienemittel, die der aufnahme harn und blut enthaltender sekrete dienen, mit geruchsverhindernden eigenschaften |
| US5098694A (en) * | 1990-09-25 | 1992-03-24 | The Procter & Gamble Company | Natural deodorant compositions |
| CA2124787C (en) * | 1991-12-13 | 1998-10-27 | Frederick E. Hardy | Acylated citrate esters as peracid precursors |
| US5713962A (en) * | 1993-06-09 | 1998-02-03 | The Procter & Gamble Company | Process for the bleaching of fabrics |
| ATE169953T1 (de) * | 1993-06-09 | 1998-09-15 | Procter & Gamble | Verfahren zur bleichung von geweben |
| WO1998029608A1 (en) * | 1996-12-30 | 1998-07-09 | Kevin Leslie Sax | Cleaning method, material and apparatus |
| IN187860B (en, 2012) * | 1997-08-27 | 2002-07-06 | Revlon Consumer Prod Corp | |
| WO2000067688A1 (en) * | 1999-05-07 | 2000-11-16 | Capitol Specialty Plastics, Inc. | Natural odor absorbency material |
| WO2002055843A1 (en) * | 2001-01-09 | 2002-07-18 | Bj Services Company | Well treatment fluid compositions and methods for their use |
| AU2003215632A1 (en) * | 2002-03-11 | 2003-09-22 | Unilever Plc | Cosmetic compositions comprising citric acid triesters |
| US20100204323A1 (en) * | 2004-12-09 | 2010-08-12 | The Dial Corporation | Antimicrobial compositions comprising organic acid esters and methods for reducing virus and bacterial populations using such compositions |
| CA2687418A1 (en) * | 2007-05-18 | 2008-11-27 | Agion Technologies, Inc. | Bioactive acid agrichemical compositions and use thereof |
| US8741275B2 (en) | 2010-06-04 | 2014-06-03 | Robetet, Inc. | Malodor neutralizing compositions comprising undecylenic acid or citric acid |
| US8802653B2 (en) | 2010-10-01 | 2014-08-12 | C.B. Fleet Company, Inc. | Deodorant compositions |
| US8685380B2 (en) | 2010-10-25 | 2014-04-01 | C.B. Fleet Company, Inc. | Deodorant spray |
| ES2819073T3 (es) | 2011-01-27 | 2021-04-14 | Robertet Inc | Composiciones neutralizantes del mal olor que comprenden acetato de bornilo o acetato de isobornilo |
| US9114180B2 (en) | 2012-03-30 | 2015-08-25 | Robertet, Inc. | Malodor neutralizing compositions containing acids and alicyclic ketones |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124506A (en) * | 1964-03-10 | Compositions containing lactic acid | ||
| NL259508A (en, 2012) * | 1959-12-29 | |||
| GB1388836A (en) * | 1971-06-01 | 1975-03-26 | Medisan Ab | Cosmetic compositions |
| US3833720A (en) * | 1972-07-14 | 1974-09-03 | Gillette Co | Astringent compositions |
-
1974
- 1974-04-16 DE DE2418338A patent/DE2418338B2/de not_active Ceased
-
1975
- 1975-01-01 AR AR258375A patent/AR204576A1/es active
- 1975-03-20 NL NL7503336A patent/NL7503336A/xx active Search and Examination
- 1975-03-20 SE SE7503216A patent/SE403567B/xx not_active IP Right Cessation
- 1975-04-02 US US05/564,555 patent/US4010253A/en not_active Expired - Lifetime
- 1975-04-02 CA CA223,608A patent/CA1041016A/en not_active Expired
- 1975-04-09 IT IT22155/75A patent/IT1034973B/it active
- 1975-04-11 AT AT277475A patent/AT332978B/de not_active IP Right Cessation
- 1975-04-14 BE BE155382A patent/BE827906A/xx not_active IP Right Cessation
- 1975-04-15 CH CH479175A patent/CH595839A5/xx not_active IP Right Cessation
- 1975-04-15 GB GB1533875A patent/GB1453266A/en not_active Expired
- 1975-04-16 FR FR7511858A patent/FR2267756B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2267756B1 (en, 2012) | 1978-12-29 |
| CH595839A5 (en, 2012) | 1978-02-28 |
| DE2418338B2 (de) | 1978-09-28 |
| AR204576A1 (es) | 1976-02-12 |
| NL7503336A (nl) | 1975-10-20 |
| DE2418338A1 (de) | 1975-11-20 |
| IT1034973B (it) | 1979-10-10 |
| ATA277475A (de) | 1976-02-15 |
| SE7503216L (sv) | 1975-10-17 |
| BE827906A (fr) | 1975-10-14 |
| AT332978B (de) | 1976-10-25 |
| FR2267756A1 (en, 2012) | 1975-11-14 |
| US4010253A (en) | 1977-03-01 |
| GB1453266A (en) | 1976-10-20 |
| SE403567B (sv) | 1978-08-28 |
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