CA2408137A1 - Oil-in-water emulsion formulation containing hydroquinone and retinol - Google Patents
Oil-in-water emulsion formulation containing hydroquinone and retinol Download PDFInfo
- Publication number
- CA2408137A1 CA2408137A1 CA002408137A CA2408137A CA2408137A1 CA 2408137 A1 CA2408137 A1 CA 2408137A1 CA 002408137 A CA002408137 A CA 002408137A CA 2408137 A CA2408137 A CA 2408137A CA 2408137 A1 CA2408137 A1 CA 2408137A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroquinone
- formulation
- retinol
- emulsion
- weight
- 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.)
- Granted
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims abstract 32
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 title claims abstract 18
- 238000009472 formulation Methods 0.000 title claims abstract 18
- 239000000203 mixture Substances 0.000 title claims abstract 18
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 title claims abstract 9
- 229960003471 retinol Drugs 0.000 title claims abstract 9
- 235000020944 retinol Nutrition 0.000 title claims abstract 9
- 239000011607 retinol Substances 0.000 title claims abstract 9
- 239000007764 o/w emulsion Substances 0.000 title claims abstract 8
- 239000011859 microparticle Substances 0.000 claims abstract 12
- 229920006037 cross link polymer Polymers 0.000 claims 12
- 239000000839 emulsion Substances 0.000 claims 7
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 2
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water 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
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/0275—Containing agglomerated particulates
-
- 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
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/0279—Porous; Hollow
-
- 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
- A61K8/347—Phenols
-
- 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
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
-
- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- 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
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Colloid Chemistry (AREA)
Abstract
An oil-in-water emulsion formulation containing hydroquinone and retinol, which comprises an oil-in-water emulsion containing hydroquinone entrapped in absorbent micro-agglomerates or impregnated in porous microparticles and retinol-impregnated microparticles.
Claims (22)
1. An oil-in-water emulsion formulation containing hydroquinone and retinol, comprising:
(i) an oil-in-water emulsion; and (ii) dispersed within the oil-in-water emulsion, (a) one or both of hydroquinone entrapped in micro-agglomerates and hydroquinone-impregnated porous microparticles; and (b) retinol-impregnated porous microparticles.
(i) an oil-in-water emulsion; and (ii) dispersed within the oil-in-water emulsion, (a) one or both of hydroquinone entrapped in micro-agglomerates and hydroquinone-impregnated porous microparticles; and (b) retinol-impregnated porous microparticles.
2. The formulation of Claim 1, where the hydroquinone content of the emulsion is from about 0.001 % to about 10% by weight.
3. The formulation of Claim 2, where the hydroquinone content of the emulsion is from about 0.01% to about 5% by weight.
4. The formulation of Claim 1, where at least a part of the hydroquinone is present entrapped in micro-agglomerates.
5. The formulation of any one of Claims 1 and 4, where the micro-agglomerates comprise a cross-linked polymer selected from the group consisting of a styrene/divinylbenzene crosspolymer, a vinyl stearate/divinylbenzene crosspolymer, a methyl methacrylate/ethylene glycol dimethacrylate crosspolymer, and a lauryl methacrylate/ethylene glycol dimethacrylate crosspolymer.
6. The formulation of Claim 5, where the micro-agglomerates comprise a lauryl methacrylate/ethylene glycol dimethacrylate crosspolymer.
7. The formulation of Claim 1, where at least a part of the hydroquinone is present in hydroquinone-impregnated porous microparticles.
8. The formulation of any one of Claims 1 to 7, where the retinol content of the emulsion is from about 0.0001% to about 10% by weight.
9. The formulation of Claim 8, where the retinol content is from about 0.001%
to about 5%
by weight.
to about 5%
by weight.
10. The formulation of any one of Claims 1 to 9, where the porous microparticles have a weight average diameter less than 50 µm.
11. The formulation of Claim 10, where the porous microparticles have a weight average diameter of about 20 µm.
12. The formulation of any one of Claims 1 to 11, where the porous microparticles comprise a cross-linked polymer selected from the group consisting of a styrene/divinylbenzene crosspolymer, a vinyl stearate/divinylbenzene crosspolymer, a methyl methacrylate/ethylene glycol dimethacrylate crosspolymer, and a lauryl methacrylate/ethylene glycol dimethacrylate crosspolymer.
13. The formulation of Claim 12, where the porous microparticles comprise a methyl methacrylate/ethylene glycol dimethacrylate crosspolymer.
14. The formulation of any one of Claims 1 to 13, further comprising at least one additional component selected from an antioxidant, a chelating agent, a colorant, a fragrance, and a preservative.
15. A use of the formulation of any one of Claims 1 to 14 for the simultaneous application of hydroquinone and retinol to the skin.
16. The use of Claim 15, where the hydroquinone content of the emulsion is from about 0.001 % to about 10% by weight.
17. The use of Claim 16, where the hydroquinone content of the emulsion is from about 0.01% to about 5% by weight.
18. The use of Claim 15, where the retinol content of the emulsion is from about 0.0001 % to about 10% by weight.
19. The use of Claim 18, where the retinol content of the emulsion is from about 0.001 % to about 5% by weight.
20. The use of Claim 15, where at least a part of the hydroquinone is present entrapped in micro-agglomerates.
21. The use of Claim 15, where at least a part of the hydroquinone is present in hydroquinone-impregnated porous microparticles.
22. A process fox the preparation of an oil-in-water emulsion formulation containing hydroquinone and retinol, said process comprising dispersing one or both of hydroquinone entrapped in micro-agglomerates and hydroquinone-impregnated porous microparticles and retinol-impregnated porous microparticles in an oil-in-water emulsion.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56532000A | 2000-05-05 | 2000-05-05 | |
| US09/565,320 | 2000-05-05 | ||
| PCT/US2001/014434 WO2001085102A2 (en) | 2000-05-05 | 2001-05-03 | Oil-in-water emulsion formulation containing hydroquinone and retinol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2408137A1 true CA2408137A1 (en) | 2001-11-15 |
| CA2408137C CA2408137C (en) | 2011-04-19 |
Family
ID=24258089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2408137A Expired - Lifetime CA2408137C (en) | 2000-05-05 | 2001-05-03 | Oil-in-water emulsion formulation containing hydroquinone and retinol |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1278504A2 (en) |
| AR (1) | AR028085A1 (en) |
| AU (1) | AU2001257534A1 (en) |
| CA (1) | CA2408137C (en) |
| WO (1) | WO2001085102A2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022219018A1 (en) * | 2021-04-16 | 2022-10-20 | Dsm Ip Assets B.V. | Retinol formulation (iii) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6673847B2 (en) * | 2002-04-01 | 2004-01-06 | Rohm And Haas Company | Water immiscible porogen removal process |
| IL152486A0 (en) | 2002-10-25 | 2003-05-29 | Meir Eini | Alcohol-free cosmetic and pharmaceutical foam carrier |
| US9265725B2 (en) | 2002-10-25 | 2016-02-23 | Foamix Pharmaceuticals Ltd. | Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof |
| US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
| US7820145B2 (en) | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| US9668972B2 (en) | 2002-10-25 | 2017-06-06 | Foamix Pharmaceuticals Ltd. | Nonsteroidal immunomodulating kit and composition and uses thereof |
| US7700076B2 (en) | 2002-10-25 | 2010-04-20 | Foamix, Ltd. | Penetrating pharmaceutical foam |
| US7704518B2 (en) | 2003-08-04 | 2010-04-27 | Foamix, Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
| JP2006505583A (en) | 2002-10-25 | 2006-02-16 | フォーミックス エルティーディー． | Cosmetic and pharmaceutical foam |
| US8900554B2 (en) | 2002-10-25 | 2014-12-02 | Foamix Pharmaceuticals Ltd. | Foamable composition and uses thereof |
| US20080138296A1 (en) | 2002-10-25 | 2008-06-12 | Foamix Ltd. | Foam prepared from nanoemulsions and uses |
| US10117812B2 (en) | 2002-10-25 | 2018-11-06 | Foamix Pharmaceuticals Ltd. | Foamable composition combining a polar solvent and a hydrophobic carrier |
| US8795693B2 (en) | 2003-08-04 | 2014-08-05 | Foamix Ltd. | Compositions with modulating agents |
| US20140161751A1 (en) * | 2004-12-02 | 2014-06-12 | Omp, Inc. | Stable skin care compositions and methods for manufacturing them |
| US10252088B2 (en) | 2004-12-02 | 2019-04-09 | Obagi Cosmeceuticals Llc | Topical compositions and methods of manufacturing them in specifically treated steel vessels |
| US8999356B1 (en) | 2004-12-03 | 2015-04-07 | Omp, Inc. | Drug delivery system |
| US7976854B2 (en) | 2005-12-30 | 2011-07-12 | Omp, Inc. | Method of treating skin requiring skin cancer treatment |
| US20080260655A1 (en) | 2006-11-14 | 2008-10-23 | Dov Tamarkin | Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses |
| US8636982B2 (en) | 2007-08-07 | 2014-01-28 | Foamix Ltd. | Wax foamable vehicle and pharmaceutical compositions thereof |
| WO2009069006A2 (en) | 2007-11-30 | 2009-06-04 | Foamix Ltd. | Foam containing benzoyl peroxide |
| WO2009090495A2 (en) | 2007-12-07 | 2009-07-23 | Foamix Ltd. | Oil and liquid silicone foamable carriers and formulations |
| US8273791B2 (en) | 2008-01-04 | 2012-09-25 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
| KR20100125278A (en) * | 2008-02-01 | 2010-11-30 | 암콜 인터내셔널 코포레이션 | Improved skin brightening compositions |
| US20120087872A1 (en) | 2009-04-28 | 2012-04-12 | Foamix Ltd. | Foamable Vehicles and Pharmaceutical Compositions Comprising Aprotic Polar Solvents and Uses Thereof |
| CA2769625C (en) | 2009-07-29 | 2017-04-11 | Foamix Ltd. | Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses |
| WO2011013008A2 (en) | 2009-07-29 | 2011-02-03 | Foamix Ltd. | Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses |
| WO2011039638A2 (en) | 2009-10-02 | 2011-04-07 | Foamix Ltd. | Topical tetracycline compositions |
| US9849142B2 (en) | 2009-10-02 | 2017-12-26 | Foamix Pharmaceuticals Ltd. | Methods for accelerated return of skin integrity and for the treatment of impetigo |
| WO2012007843A2 (en) | 2010-07-12 | 2012-01-19 | Foamix Ltd. | Apparatus and method for releasing a unit dose of content from a container |
| MX2020012139A (en) | 2016-09-08 | 2021-01-29 | Vyne Pharmaceuticals Inc | Compositions and methods for treating rosacea and acne. |
| EP4322914A1 (en) * | 2021-04-16 | 2024-02-21 | DSM IP Assets B.V. | Retinol formulation (ii) |
| CN116251035A (en) * | 2023-03-17 | 2023-06-13 | 深圳市护家科技有限公司 | An oily composition containing retinol and/or retinol derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966773A (en) * | 1986-11-25 | 1990-10-30 | Alcon Laboratories, Inc. | Topical ophthalmic compositions containing microfine retinoid particles |
| JP3014780B2 (en) * | 1990-01-29 | 2000-02-28 | ジヨンソン・アンド・ジヨンソン・コンシユーマー・プロダクツ・インコーポレーテツド | Skin care composition |
| US6107429A (en) * | 1994-10-24 | 2000-08-22 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5851538A (en) * | 1995-12-29 | 1998-12-22 | Advanced Polymer Systems, Inc. | Retinoid formulations in porous microspheres for reduced irritation and enhanced stability |
| CN1136431A (en) * | 1996-04-26 | 1996-11-27 | 朱宝义 | Acne cream |
| US6068847A (en) * | 1996-10-03 | 2000-05-30 | Johnson & Johnson Consumer Products, Inc. | Cosmetic compositions |
| US6228894B1 (en) * | 1998-04-17 | 2001-05-08 | Enhanced Derm Technologies, Inc. | Softgel-compatible composition containing retinol |
| US5891470A (en) * | 1998-04-17 | 1999-04-06 | Advanced Polymer Systems, Inc. | Softgel formulation containing retinol |
-
2001
- 2001-05-03 EP EP01931059A patent/EP1278504A2/en not_active Ceased
- 2001-05-03 AU AU2001257534A patent/AU2001257534A1/en not_active Abandoned
- 2001-05-03 CA CA2408137A patent/CA2408137C/en not_active Expired - Lifetime
- 2001-05-03 WO PCT/US2001/014434 patent/WO2001085102A2/en not_active Ceased
- 2001-05-04 AR ARP010102120A patent/AR028085A1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022219018A1 (en) * | 2021-04-16 | 2022-10-20 | Dsm Ip Assets B.V. | Retinol formulation (iii) |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001085102A8 (en) | 2003-11-20 |
| CA2408137C (en) | 2011-04-19 |
| AU2001257534A1 (en) | 2001-11-20 |
| WO2001085102A3 (en) | 2002-08-29 |
| EP1278504A2 (en) | 2003-01-29 |
| AR028085A1 (en) | 2003-04-23 |
| WO2001085102A2 (en) | 2001-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20210503 |