TW200301136A - Stabilization of vitamins in water-in-silicone oil (W/O) emulsions - Google Patents
Stabilization of vitamins in water-in-silicone oil (W/O) emulsions Download PDFInfo
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- TW200301136A TW200301136A TW091135838A TW91135838A TW200301136A TW 200301136 A TW200301136 A TW 200301136A TW 091135838 A TW091135838 A TW 091135838A TW 91135838 A TW91135838 A TW 91135838A TW 200301136 A TW200301136 A TW 200301136A
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- Prior art keywords
- emulsion
- silicone
- tocopherol
- vitamin
- patent application
- Prior art date
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- 239000000839 emulsion Substances 0.000 title claims abstract description 28
- 229940088594 vitamin Drugs 0.000 title claims abstract description 13
- 229930003231 vitamin Natural products 0.000 title claims abstract description 13
- 235000013343 vitamin Nutrition 0.000 title claims abstract description 13
- 239000011782 vitamin Substances 0.000 title claims abstract description 13
- 229920002545 silicone oil Polymers 0.000 title description 4
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 42
- 229920002379 silicone rubber Polymers 0.000 claims abstract description 34
- 239000012071 phase Substances 0.000 claims abstract description 26
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 23
- 229920000570 polyether Polymers 0.000 claims abstract description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000008346 aqueous phase Substances 0.000 claims abstract description 9
- 150000003722 vitamin derivatives Chemical class 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 45
- -1 Tocopheryl palmitate Chemical compound 0.000 claims description 39
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000011732 tocopherol Substances 0.000 claims description 7
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 6
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 6
- 229930003799 tocopherol Natural products 0.000 claims description 6
- 229960001295 tocopherol Drugs 0.000 claims description 6
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 6
- 229930003427 Vitamin E Natural products 0.000 claims description 5
- 235000010384 tocopherol Nutrition 0.000 claims description 5
- 239000011709 vitamin E Substances 0.000 claims description 5
- 235000019165 vitamin E Nutrition 0.000 claims description 5
- 229940046009 vitamin E Drugs 0.000 claims description 5
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 4
- PGTMTTGPWLZNQO-UHFFFAOYSA-N 2-dodecyl-1,3,5,7,9,11-hexaoxa-2,4,6,8,10,12-hexasilacyclododecane Chemical compound C(CCCCCCCCCCC)[SiH]1O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O1 PGTMTTGPWLZNQO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 3
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960002685 biotin Drugs 0.000 claims description 3
- 235000020958 biotin Nutrition 0.000 claims description 3
- 239000011616 biotin Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- YDWFEBCFKZDCTM-UHFFFAOYSA-N hexadecyl(silyloxysilyloxysilyloxysilyloxysilyloxysilyloxy)silane Chemical compound C(CCCCCCCCCCCCCCC)[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH3] YDWFEBCFKZDCTM-UHFFFAOYSA-N 0.000 claims description 3
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 3
- KKADPXVIOXHVKN-UHFFFAOYSA-N 4-hydroxyphenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=C(O)C=C1 KKADPXVIOXHVKN-UHFFFAOYSA-N 0.000 claims description 2
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 2
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 claims description 2
- IELOKBJPULMYRW-NJQVLOCASA-N D-alpha-Tocopheryl Acid Succinate Chemical compound OC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C IELOKBJPULMYRW-NJQVLOCASA-N 0.000 claims description 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 2
- MSCCTZZBYHQMQJ-AZAGJHQNSA-N Tocopheryl nicotinate Chemical compound C([C@@](OC1=C(C)C=2C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC1=C(C)C=2OC(=O)C1=CC=CN=C1 MSCCTZZBYHQMQJ-AZAGJHQNSA-N 0.000 claims description 2
- 229930003471 Vitamin B2 Natural products 0.000 claims description 2
- 125000005376 alkyl siloxane group Chemical group 0.000 claims description 2
- 229940099418 d- alpha-tocopherol succinate Drugs 0.000 claims description 2
- HNDMWPOGQFUHIL-UHFFFAOYSA-N dodecyl(silyloxysilyloxysilyloxysilyloxy)silane Chemical compound CCCCCCCCCCCC[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH3] HNDMWPOGQFUHIL-UHFFFAOYSA-N 0.000 claims description 2
- 229960000304 folic acid Drugs 0.000 claims description 2
- 235000019152 folic acid Nutrition 0.000 claims description 2
- 239000011724 folic acid Substances 0.000 claims description 2
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940055726 pantothenic acid Drugs 0.000 claims description 2
- 235000019161 pantothenic acid Nutrition 0.000 claims description 2
- 239000011713 pantothenic acid Substances 0.000 claims description 2
- 229960002477 riboflavin Drugs 0.000 claims description 2
- 229960000984 tocofersolan Drugs 0.000 claims description 2
- 229950009883 tocopheryl nicotinate Drugs 0.000 claims description 2
- 235000019164 vitamin B2 Nutrition 0.000 claims description 2
- 239000011716 vitamin B2 Substances 0.000 claims description 2
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 claims 2
- 229930003451 Vitamin B1 Natural products 0.000 claims 1
- 229940087168 alpha tocopherol Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229940066595 beta tocopherol Drugs 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 230000004151 fermentation Effects 0.000 claims 1
- 238000000855 fermentation Methods 0.000 claims 1
- 235000010382 gamma-tocopherol Nutrition 0.000 claims 1
- 229960003495 thiamine Drugs 0.000 claims 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 claims 1
- 235000010374 vitamin B1 Nutrition 0.000 claims 1
- 239000011691 vitamin B1 Substances 0.000 claims 1
- 235000004835 α-tocopherol Nutrition 0.000 claims 1
- 239000002076 α-tocopherol Substances 0.000 claims 1
- 239000011590 β-tocopherol Substances 0.000 claims 1
- 235000007680 β-tocopherol Nutrition 0.000 claims 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 claims 1
- 239000002478 γ-tocopherol Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 21
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 9
- 239000007762 w/o emulsion Substances 0.000 abstract description 2
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- 238000000034 method Methods 0.000 description 18
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- 238000009835 boiling Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000005702 oxyalkylene group Chemical group 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
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- 239000003431 cross linking reagent Substances 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 229960001484 edetic acid Drugs 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
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- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- 239000011718 vitamin C Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
-
- 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
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61K8/67—Vitamins
- A61K8/678—Tocopherol, i.e. vitamin E
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/024,983 US6861061B2 (en) | 2001-12-19 | 2001-12-19 | Stabilization of vitamins in water-in silicone oil (W/O) emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200301136A true TW200301136A (en) | 2003-07-01 |
Family
ID=21823398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091135838A TW200301136A (en) | 2001-12-19 | 2002-12-11 | Stabilization of vitamins in water-in-silicone oil (W/O) emulsions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6861061B2 (enExample) |
| EP (1) | EP1455735A1 (enExample) |
| JP (1) | JP2005514391A (enExample) |
| CN (1) | CN1620278A (enExample) |
| AU (1) | AU2002353003A1 (enExample) |
| TW (1) | TW200301136A (enExample) |
| WO (1) | WO2003053372A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1746968A2 (en) * | 2004-04-20 | 2007-01-31 | Dow Corning Corporation | Silicone vesicles containing actives |
| CN102293722B (zh) * | 2004-04-20 | 2013-08-28 | 陶氏康宁公司 | 制备小泡组合物的方法和由此生产的小泡组合物 |
| WO2005103118A1 (en) | 2004-04-20 | 2005-11-03 | Dow Corning Corporation | Aqueous dispersions of silicone polyether block copolymers |
| JP2009513661A (ja) * | 2005-11-01 | 2009-04-02 | ダウ・コーニング・コーポレイション | 活性剤を含むシリコーンベシクル |
| CN101394826A (zh) * | 2006-02-28 | 2009-03-25 | 陶氏康宁公司 | 含有活性成分的硅氧烷小泡 |
| US20070207107A1 (en) * | 2006-03-03 | 2007-09-06 | Gareth Winckle | Silicone based emulsions for topical drug delivery |
| US7790701B2 (en) * | 2006-04-19 | 2010-09-07 | Gelest Technologies, Inc. | Silicon-based tocopherol derivatives |
| US20080059313A1 (en) * | 2006-08-30 | 2008-03-06 | Oblong John E | Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair |
| US8425923B2 (en) * | 2007-02-09 | 2013-04-23 | Dow Corning Corporation and McNeil-PPC, Inc. | Lotion composition for personal use |
| CN101715339B (zh) * | 2007-02-09 | 2014-07-09 | 麦克内尔-Ppc股份有限公司 | 个人使用的洗剂组合物 |
| EP2249782B1 (en) * | 2008-02-29 | 2017-08-30 | The Procter and Gamble Company | Hair care compositions and methods for increasing hair diameter |
| CN101297680B (zh) * | 2008-04-25 | 2010-11-03 | 天津生机集团股份有限公司 | 一种复合维生素乳液及其制备方法 |
| WO2013096645A1 (en) | 2011-12-20 | 2013-06-27 | The Procter & Gamble Company | Human skin sample methods and models for validating hypotheses for mechanisms driving skin pigmentation |
| MX2015015676A (es) | 2013-05-16 | 2016-03-04 | Procter & Gamble | Composiciones de espesamiento para el cabello y metodos de uso. |
| US9437170B1 (en) * | 2013-08-12 | 2016-09-06 | Roberto Quevedo Montesdeoca | Systems and methods for augmented reality display |
| CA3011347A1 (en) | 2016-01-13 | 2017-07-20 | Schlumberger Canada Limited | Angled chisel insert |
| CN106243364B (zh) * | 2016-08-03 | 2018-05-01 | 广东工业大学 | 一种聚醚改性有机硅乳液及其制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150048A (en) * | 1978-03-28 | 1979-04-17 | Union Carbide Corporation | Nonhydrolyzable siloxane block copolymers of organosiloxanes and organic ethers |
| JPS62243621A (ja) | 1986-04-17 | 1987-10-24 | Toray Silicone Co Ltd | シリコ−ンゴム粒状物の製造方法 |
| US4853474A (en) | 1987-07-08 | 1989-08-01 | Dow Corning Corporation | Cross-linked organopolysiloxanes and emulsions based thereon |
| US5266321A (en) | 1988-03-31 | 1993-11-30 | Kobayashi Kose Co., Ltd. | Oily make-up cosmetic comprising oil base and silicone gel composition |
| JPH0753646B2 (ja) | 1989-01-31 | 1995-06-07 | 東レ・ダウコーニング・シリコーン株式会社 | 化粧料 |
| US5136068A (en) | 1989-04-26 | 1992-08-04 | Dow Corning Corporation | Cross-linked organopolysiloxanes and emulsions based thereon |
| US5599533A (en) | 1994-12-15 | 1997-02-04 | Estee Lauder, Inc. | Stable water-in-oil emulsion system |
| US5654362A (en) | 1996-03-20 | 1997-08-05 | Dow Corning Corporation | Silicone oils and solvents thickened by silicone elastomers |
| US5750123A (en) | 1996-06-28 | 1998-05-12 | Chesebrough-Pond's Co., Division Of Conopco, Inc. | Vitamin C delivery system |
| US5880210A (en) | 1997-04-01 | 1999-03-09 | Dow Corning Corporation | Silicone fluids and solvents thickened with silicone elastomers |
| US5889108A (en) * | 1997-06-02 | 1999-03-30 | Dow Corning Corporation | Thickening solvents with elastomeric silicone polyethers |
| US6207717B1 (en) | 1999-01-12 | 2001-03-27 | Dow Corning Corporation | Entrapment of vitamins with an elastomeric silicone polyether |
| US5948855A (en) | 1999-01-12 | 1999-09-07 | Dow Corning Corporation | Water-in-oil-in water emulsion |
| US6168782B1 (en) | 1999-05-24 | 2001-01-02 | Dow Corning Corporation | Elastomeric silicone containing an active ingredient |
| WO2000072817A1 (en) | 1999-05-28 | 2000-12-07 | Neutrogena Corporation | Water-in-oil emulsion comprising a silicone gel containing vitamin c |
| JP2001002555A (ja) | 1999-06-24 | 2001-01-09 | Shin Etsu Chem Co Ltd | 皮膚化粧料 |
| US6221979B1 (en) | 1999-11-08 | 2001-04-24 | Dow Corning Corporation | Mixtures of silicone elastomers |
-
2001
- 2001-12-19 US US10/024,983 patent/US6861061B2/en not_active Expired - Fee Related
-
2002
- 2002-12-03 CN CNA028232984A patent/CN1620278A/zh active Pending
- 2002-12-03 AU AU2002353003A patent/AU2002353003A1/en not_active Abandoned
- 2002-12-03 WO PCT/US2002/038430 patent/WO2003053372A1/en not_active Ceased
- 2002-12-03 JP JP2003554132A patent/JP2005514391A/ja active Pending
- 2002-12-03 EP EP02789969A patent/EP1455735A1/en not_active Withdrawn
- 2002-12-11 TW TW091135838A patent/TW200301136A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003053372A1 (en) | 2003-07-03 |
| US6861061B2 (en) | 2005-03-01 |
| CN1620278A (zh) | 2005-05-25 |
| EP1455735A1 (en) | 2004-09-15 |
| JP2005514391A (ja) | 2005-05-19 |
| US20030119779A1 (en) | 2003-06-26 |
| AU2002353003A1 (en) | 2003-07-09 |
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