CA2398056A1 - Enhanced efficacy aluminum-zirconium antiperspirants and methods for making - Google Patents
Enhanced efficacy aluminum-zirconium antiperspirants and methods for making Download PDFInfo
- Publication number
- CA2398056A1 CA2398056A1 CA002398056A CA2398056A CA2398056A1 CA 2398056 A1 CA2398056 A1 CA 2398056A1 CA 002398056 A CA002398056 A CA 002398056A CA 2398056 A CA2398056 A CA 2398056A CA 2398056 A1 CA2398056 A1 CA 2398056A1
- Authority
- CA
- Canada
- Prior art keywords
- aluminum
- zirconium
- band
- solution
- percent
- 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.)
- Abandoned
Links
- 239000003213 antiperspirant Substances 0.000 title claims abstract description 24
- 230000001166 anti-perspirative effect Effects 0.000 title claims abstract description 23
- ZGUQGPFMMTZGBQ-UHFFFAOYSA-N [Al].[Al].[Zr] Chemical compound [Al].[Al].[Zr] ZGUQGPFMMTZGBQ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 33
- 239000000243 solution Substances 0.000 claims abstract description 52
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 45
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001413 amino acids Chemical class 0.000 claims abstract description 10
- 150000003755 zirconium compounds Chemical class 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract 10
- 239000012265 solid product Substances 0.000 claims abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 72
- 229910052782 aluminium Inorganic materials 0.000 claims description 43
- 239000004471 Glycine Substances 0.000 claims description 36
- 229910052726 zirconium Inorganic materials 0.000 claims description 21
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 claims description 13
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 1
- 210000001099 axilla Anatomy 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000007853 buffer solution Substances 0.000 abstract description 3
- DNXNYEBMOSARMM-UHFFFAOYSA-N alumane;zirconium Chemical class [AlH3].[Zr] DNXNYEBMOSARMM-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001694 spray drying Methods 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 75
- 241000894007 species Species 0.000 description 28
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- ZBJWWKFMHOAPNS-UHFFFAOYSA-N loretin Chemical compound C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 ZBJWWKFMHOAPNS-UHFFFAOYSA-N 0.000 description 14
- 229950010248 loretin Drugs 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 9
- -1 Aluminum halide Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229910018580 Al—Zr Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 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
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 229930182821 L-proline Natural products 0.000 description 1
- 241000408529 Libra Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- WWHZEXDIQCJXSV-UHFFFAOYSA-N aluminum;trihypochlorite Chemical compound [Al+3].Cl[O-].Cl[O-].Cl[O-] WWHZEXDIQCJXSV-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PCWMQBFZWUVOJZ-UHFFFAOYSA-L magnesium;2-(hydroxyamino)acetate Chemical compound [Mg+2].ONCC([O-])=O.ONCC([O-])=O PCWMQBFZWUVOJZ-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000600 sorbitol 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/28—Zirconium; Compounds thereof
-
- 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
- A61K8/345—Alcohols containing more than one hydroxy group
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/58—Metal complex; Coordination compounds
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)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/496,168 | 2000-02-01 | ||
| US09/496,168 US6451296B1 (en) | 2000-02-01 | 2000-02-01 | Enhanced efficacy aluminum-zirconium antiperspirants and methods for making |
| PCT/US2000/033168 WO2001056539A1 (en) | 2000-02-01 | 2000-12-06 | Enhanced efficacy aluminum-zirconium antiperspirants and methods for making |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2398056A1 true CA2398056A1 (en) | 2001-08-09 |
Family
ID=23971532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002398056A Abandoned CA2398056A1 (en) | 2000-02-01 | 2000-12-06 | Enhanced efficacy aluminum-zirconium antiperspirants and methods for making |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6451296B1 (enExample) |
| EP (1) | EP1251825A4 (enExample) |
| JP (1) | JP2003523970A (enExample) |
| AU (2) | AU1952001A (enExample) |
| CA (1) | CA2398056A1 (enExample) |
| WO (1) | WO2001056539A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436381B1 (en) | 2000-10-25 | 2002-08-20 | The Gillette Company | Aluminum-zirconium antiperspirant salts with high peak 5 al content |
| US6719965B2 (en) | 2002-02-19 | 2004-04-13 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Antiperspirant or deodorant composition |
| US6726901B2 (en) | 2002-05-09 | 2004-04-27 | The Gillette Company | Stabilized antiperspirant compositions containing aluminum-zirconium salts with low M:Cl ratio |
| US6663854B1 (en) | 2002-06-19 | 2003-12-16 | Yan-Fei Shen | Aluminum-zirconium antiperspirant salts made with zirconium salts having low Zr:Cl ratio |
| US6960338B2 (en) * | 2002-06-28 | 2005-11-01 | Reheis, Inc. | Amino acid free stable aluminum/zirconium antiperspirant solution |
| US6649153B1 (en) * | 2002-09-16 | 2003-11-18 | Reheis Inc. | Skin friendly antiperspirant composition and method of making |
| US20040091436A1 (en) * | 2002-11-12 | 2004-05-13 | Zijun Li | Antiperspirant compositions of enhanced efficacy containing strontium |
| GB0304508D0 (en) * | 2003-02-27 | 2003-04-02 | Unilever Plc | Antiperspirant actives and compositions |
| US7105691B2 (en) * | 2003-06-26 | 2006-09-12 | Colgate-Palmolive Company | Aluminum / zirconium / glycine antiperspirant actives stabilized with Betaine |
| US7014843B2 (en) * | 2004-03-24 | 2006-03-21 | Reheis, Inc. | Enhanced efficacy basic aluminum halides/metal cation salt, antiperspirants actives and compositions containing such materials and methods for making |
| US6902724B1 (en) | 2004-03-24 | 2005-06-07 | Reheis, Inc. | Enhanced efficacy basic aluminum halides, antiperspirant active compositions and methods for making |
| US7153495B2 (en) * | 2004-06-10 | 2006-12-26 | Reheis, Inc. | Fragrance friendly and cost effective antiperspirant actives and method of making the same |
| US7846318B2 (en) * | 2006-01-06 | 2010-12-07 | Nextchem, Llc | Polyaluminum chloride and aluminum chlorohydrate, processes and compositions: high-basicity and ultra high-basicity products |
| US8801909B2 (en) * | 2006-01-06 | 2014-08-12 | Nextchem, Llc | Polymetal hydroxychloride processes and compositions: enhanced efficacy antiperspirant salt compositions |
| BR112013010694A2 (pt) | 2010-11-02 | 2016-07-05 | Colgate Palmolive Co | composições antitranspirantes ativas e sua produção |
| US9463985B2 (en) | 2010-11-02 | 2016-10-11 | Colgate-Palmolive Company | Aluminum salt containing high percentage of Al30 |
| MX361821B (es) | 2011-04-26 | 2018-12-18 | Colgate Palmolive Co | Composiciones que contienen cationes de polihidroxioxoaluminio y fabricación de los mismos. |
| AU2011366870B2 (en) | 2011-04-26 | 2014-10-30 | Colgate-Palmolive Company | Antiperspirant active compositions and manufacture thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507896A (en) | 1968-10-23 | 1970-04-21 | Armour Pharma | Method of making alcohol-soluble complexes of aluminum |
| US3981986A (en) | 1973-11-23 | 1976-09-21 | Armour Pharmaceutical Company | Zirconium-aluminum-polyol buffered anti-perspirant complexes |
| US4359456A (en) | 1976-01-14 | 1982-11-16 | Lever Brothers Company | Antiperspirant activity of basic aluminum compounds |
| US5356609A (en) | 1986-01-08 | 1994-10-18 | Westwood Chemical Corp. | Method for preparing basic aluminum halides by reacting aluminum halide with aluminum |
| US4871525A (en) * | 1986-10-24 | 1989-10-03 | Westwood Chemical Corporation | Antiperspirant composition and method of preparation |
| US5330751A (en) * | 1988-04-14 | 1994-07-19 | The Gilette Company | Antiperspirant and method of making same |
| EP0404533A1 (en) * | 1989-06-23 | 1990-12-27 | The Procter & Gamble Company | Liquid solubilized antiperspirant actives and processes for preparing the same |
| CA2046170A1 (en) | 1990-07-10 | 1992-01-11 | Morton Lawrence Barr | Basic aluminum antiperspirant active materials having enhanced activity, antiperspirant active compositions containing such materials, and methods for preparation of such materials and compositions |
| US5179220A (en) | 1991-07-01 | 1993-01-12 | Somerville Technology Group, Inc. | Non-aqueous solutions of aluminum and aluminum-zirconium compounds |
| WO1996014052A1 (en) * | 1994-11-02 | 1996-05-17 | The Gillette Company | Method of making polyhydric alcohol solutions of enhanced efficacy antiperspirant actives |
| US6010688A (en) | 1997-06-25 | 2000-01-04 | The Gillette Company | Polyhydric alcohol stabilized antiperspirant salt solutions |
| US5955064A (en) * | 1997-10-21 | 1999-09-21 | Westwood Chemical Corporation | Enhanced efficacy stable antiperspirant active solution and method of making same |
| US6149897A (en) * | 1999-08-24 | 2000-11-21 | The Procter & Gamble Company | Process for making anhydrous compositions containing solubilized, enhanced antiperspirant active |
| US6126928A (en) * | 1999-08-24 | 2000-10-03 | The Procter & Gamble Company | Compositions containing solubilized, acid-enhanced antiperspirant active |
-
2000
- 2000-02-01 US US09/496,168 patent/US6451296B1/en not_active Expired - Fee Related
- 2000-12-06 AU AU1952001A patent/AU1952001A/xx active Pending
- 2000-12-06 EP EP00982496A patent/EP1251825A4/en not_active Withdrawn
- 2000-12-06 JP JP2001556231A patent/JP2003523970A/ja active Pending
- 2000-12-06 AU AU2001219520A patent/AU2001219520B2/en not_active Ceased
- 2000-12-06 WO PCT/US2000/033168 patent/WO2001056539A1/en not_active Ceased
- 2000-12-06 CA CA002398056A patent/CA2398056A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001219520B2 (en) | 2005-01-27 |
| EP1251825A1 (en) | 2002-10-30 |
| US6451296B1 (en) | 2002-09-17 |
| EP1251825A4 (en) | 2008-08-20 |
| JP2003523970A (ja) | 2003-08-12 |
| AU1952001A (en) | 2001-08-14 |
| WO2001056539A1 (en) | 2001-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |