DE2418338B2 - Verwendung von Estern der Citronensäure und/oder Acetylcitronensäure in wasserfreien kosmetischen Zubereitungen - Google Patents
Verwendung von Estern der Citronensäure und/oder Acetylcitronensäure in wasserfreien kosmetischen ZubereitungenInfo
- Publication number
- DE2418338B2 DE2418338B2 DE2418338A DE2418338A DE2418338B2 DE 2418338 B2 DE2418338 B2 DE 2418338B2 DE 2418338 A DE2418338 A DE 2418338A DE 2418338 A DE2418338 A DE 2418338A DE 2418338 B2 DE2418338 B2 DE 2418338B2
- Authority
- DE
- Germany
- Prior art keywords
- ester
- weight
- parts
- citric acid
- acid
- 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.)
- Ceased
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title description 46
- 150000002148 esters Chemical class 0.000 title description 22
- 239000002537 cosmetic Substances 0.000 title description 9
- 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 title description 8
- 238000002360 preparation method Methods 0.000 title description 8
- 239000002781 deodorant agent Substances 0.000 description 22
- -1 alicyclic alcohols Chemical class 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 239000003380 propellant Substances 0.000 description 8
- 230000001877 deodorizing effect Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 4
- 230000001166 anti-perspirative effect Effects 0.000 description 4
- 239000004599 antimicrobial Substances 0.000 description 4
- 239000003213 antiperspirant Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 208000035985 Body Odor Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010040904 Skin odour abnormal Diseases 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 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 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 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
- 239000004615 ingredient Substances 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 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 2
- 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
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 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
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-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
- 206010006326 Breath odour Diseases 0.000 description 1
- HVJLCBXVFFIERX-UHFFFAOYSA-N C(C)O.C(C)(C)O.C(CC(O)(C(=O)OCC)CC(=O)OCC)(=O)OCC Chemical compound C(C)O.C(C)(C)O.C(CC(O)(C(=O)OCC)CC(=O)OCC)(=O)OCC HVJLCBXVFFIERX-UHFFFAOYSA-N 0.000 description 1
- JKJVUNNSDIMKSG-UHFFFAOYSA-N CCO.CC(C)O.CCCCCCCCCCCCCC(=O)OC(C)C Chemical compound CCO.CC(C)O.CCCCCCCCCCCCCC(=O)OC(C)C JKJVUNNSDIMKSG-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
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 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
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UGHLLGNRWBZGGO-UHFFFAOYSA-L magnesium zinc oxygen(2-) carbonate Chemical compound [O-2].[Zn+2].C([O-])([O-])=O.[Mg+2] UGHLLGNRWBZGGO-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 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
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 230000008313 sensitization 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
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LCZVKKUAUWQDPX-UHFFFAOYSA-N tert-butyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl]amino]acetate Chemical compound CC(=O)OC1=CC=CC=C1CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1=CC=CC=C1OC(C)=O LCZVKKUAUWQDPX-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- MRVPOBYXKKCHEX-UHFFFAOYSA-N trimethyl 2-hydroxy-4-oxopentane-1,2,3-tricarboxylate Chemical compound COC(=O)CC(O)(C(=O)OC)C(C(C)=O)C(=O)OC MRVPOBYXKKCHEX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax 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)
Priority Applications (12)
| 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 |
| AR258375A AR204576A1 (es) | 1974-04-16 | 1975-01-01 | Composicion cosmetica |
| SE7503216A SE403567B (sv) | 1974-04-16 | 1975-03-20 | Anvendning av triestrar av citronsyra och/eller acetylcitronsyra som deodoranter i vattenfria kosmetiska beredningar for undertryckande av kroppslukt |
| NL7503336A NL7503336A (nl) | 1974-04-16 | 1975-03-20 | Toepassing van esters van het citroenzuur en/of van acetylcitroenzuur als deodorantia. |
| US05/564,555 US4010253A (en) | 1974-04-16 | 1975-04-02 | Process of suppressing odors employing deodorants containing esters of citric acid |
| CA223,608A CA1041016A (en) | 1974-04-16 | 1975-04-02 | Process of suppressing odors employing deodorants containing esters of citric acid |
| IT22155/75A IT1034973B (it) | 1974-04-16 | 1975-04-09 | Deodorante a base di esteri dell acido citrico e o dell acido acetilcitrico |
| AT277475A AT332978B (de) | 1974-04-16 | 1975-04-11 | Deodorantien |
| BE155382A BE827906A (fr) | 1974-04-16 | 1975-04-14 | Utilisation d'esters de l'acide citrique et/ou acetylcitrique en tant que desodorisants |
| GB1533875A GB1453266A (en) | 1974-04-16 | 1975-04-15 | Cosmetic preparations |
| CH479175A CH595839A5 (en, 2012) | 1974-04-16 | 1975-04-15 | |
| FR7511858A FR2267756B1 (en, 2012) | 1974-04-16 | 1975-04-16 |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2418338A1 DE2418338A1 (de) | 1975-11-20 |
| DE2418338B2 true DE2418338B2 (de) | 1978-09-28 |
Family
ID=5913053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2418338A Ceased DE2418338B2 (de) | 1974-04-16 | 1974-04-16 | Verwendung von Estern der Citronensäure und/oder Acetylcitronensäure in wasserfreien kosmetischen Zubereitungen |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2736770A1 (de) * | 1976-08-20 | 1978-02-23 | Unilever Nv | Detergensstueck fuer die koerperwaesche |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2736770A1 (de) * | 1976-08-20 | 1978-02-23 | Unilever Nv | Detergensstueck fuer die koerperwaesche |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2267756B1 (en, 2012) | 1978-12-29 |
| CH595839A5 (en, 2012) | 1978-02-28 |
| 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 |
| CA1041016A (en) | 1978-10-24 |
| US4010253A (en) | 1977-03-01 |
| GB1453266A (en) | 1976-10-20 |
| SE403567B (sv) | 1978-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8235 | Patent refused |