CA2270073A1 - Stable anhydrous formulation - Google Patents
Stable anhydrous formulation Download PDFInfo
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- CA2270073A1 CA2270073A1 CA002270073A CA2270073A CA2270073A1 CA 2270073 A1 CA2270073 A1 CA 2270073A1 CA 002270073 A CA002270073 A CA 002270073A CA 2270073 A CA2270073 A CA 2270073A CA 2270073 A1 CA2270073 A1 CA 2270073A1
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- composition
- skin
- silicone oil
- retinoid
- silicone
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- 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
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
-
- 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
-
- 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
-
- 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
-
- 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
- A61Q19/004—Aftersun preparations
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- 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
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
- A61K2800/31—Anhydrous
-
- 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
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Abstract
The present invention is a cosmetic or pharmaceutical composition for topical application comprising a silicone gel and an effective amount of a biological active, especially a retinoid. The compositions permit stabilization of the biologically active agents.
Description
STABLE ANHYDROUS FORMULATION
Field of the Invention The present invention relates to cosmetic or pharmaceutical compositions comprising stable active agents.
In particular, the invention relates to compositions in which active agents are stabilized by incorporation into a silicone gel.
1o Backcrround of the Invention In recent times, cosmetics have become developed beyond the concept of mere ornamentation for the face. Consumers now demand more from their makeup than simple color, coverage or moisturizing: it is now preferred that cosmetics provide some benefit to the skin, rather than just decorating it or making it feel softer. This consumer preference has resulted in the frequent use of biologically active ingredients, in many cosmetic products. In view of the now well-recognized damaging effects of sun exposure on 2o the skin, particularly favored active components are those which can counteract or prevent those effects. These components include, for example, sunscreens, antioxidants, and anti-wrinkle agents.
One of the primary difficulties in employing actives in a formulation is the potential instability of the active once incorporated. The very reason for their use in the formulation, i.e., their biological activity, means that they are not inert, and are therefore potentially subject to reduction or loss of potency if not combined with the proper 3o vehicle. A number of routinely encountered factors can readily inactivate a biologically active compound in a formulation before it even reaches the consumer. Such factors include, for example, oxygen, extreme temperatures, WO 99/13859 PCTlUS98/18804 UV light, water, and lipid peroxidases. It is particularly difficult to avoid the effects of oxygen and UV light, which are of course virtually ubiquitous in nature. Although water can technically be avoided by anhydrous formulation, many of the very desirable actives are water soluble, making their incorporation into an anhydrous formulation problematic. Thus, there continues to be a need for development of a cosmetically acceptable vehicle which will be capable of readily incorporating water soluble actives, l0 yet will protect the actives from environmental factors which rob them of their biological activity. The present invention provides a solution to this continuing problem.
Summary of the Invention The present invention provides an anhydrous cosmetic or pharmaceutical formulation for topical application to the skin, the formulation comprising a silicone gel, in combination with a safe and effective amount of one or more biologically active components. The invention also comprises a method of stabilizing a biologically active component, the method comprising combining the active component with a stabilizing amount of a silicone gel. A
preferred active component is a retinoid.
In a preferred embodiment, the formulation also comprises an effective amount of an oil soluble antioxidant.
Detailed Description of the Invention It has now been unexpectedly discovered that it is possible to stabilize biologically active materials by their combination with a silicone gel. The gels employed in the present invention comprise a vehicle in which an organopolysiloxane elastomer is dispersed. The vehicle can comprise any cosmetically acceptable silicone oil, or a combination of silicone oils. The silicone oil may be any volatile or non-volatile silicone oil, for example, any methylated linear or cyclic non-elastomeric organopolysiloxane, or combinations thereof. Preferably, however, the vehicle is a lower molecular weight dimethicone, trimethicone, cyclomethicone, or a mixture of such oils. Preferred silicone oils useful as the gel vehicle in the present invention include, but are not limited to, phenyl trimethicone, or methylated cyclic organopolysiloxanes having ring sizes from 4 to 12, such as to octamethylcyclotetrasiloxane or decamethylpentasiloxane.
The gel is prepared by dispersing in the vehicle an organopolysiloxane elastomer. An elastomer is generally a chain polymer having a degree of cross-linking sufficient to provide a rubber-like material. In the present gel, the elastomer is an at least partially crosslinked or at least partially cured hetero-chain elastomer. Particularly preferred are those which are at least partially cured addition reaction products, i.e., hydrosilation products, or addition polymerization products, of an organopolysiloxane having unsaturated groups, such as vinyl or allyl, preferably bonded to at least one terminal silicon atom, and another silicone compound capable of participation in the addition reaction, such as an organohydrogenpolysiloxane.
Suitable organopolysiloxane elastomers, having a three-dimensional cross-linked structure, are described, for example, in US Patent No. 5,266,321, the contents of which are incorporated herein by reference. However, other suitable elastomer materials are disclosed in, for example, US Patent Nos. 4,980,167 and 4,742,142.
3o A preferred organopolysiloxane is one which is at least partially crosslinked, or is an at least partially cured hetero-chain elastomer. In one preferred embodiment, the organopolysiloxane elastomer is one which is one which is an at least partially cured addition reaction products, i.e., hydrosilation products, or addition polymerization products, of an organopolysiloxane having unsaturated groups, such as vinyl or allyl, preferably bonded to at least one terminal Si atom, and another silicon compound capable of participation in the addition reaction, such as an organohydrogen polysiloxane.
The chosen elastomer is dispersed in the vehicle by known homogenization techniques. The elastomer dispersed in to the vehicle provides a soft, stable viscous gel, or gel-like material. Alternatively, the gel can be purchased premade, with the elastomer already dispersed in the vehicle. Such products are available under the name Gransil, for example Gransil GCM or Gransil PM, from Grant Industries, Inc., Elmwood Park, New Jersey. The amounts of elastomer and vehicle may vary, depending on the desired viscosity, but generally should be in the range of 5-40% elastomer and 60-95o vehicle.
The gel so prepared can be directly combined with the 2o desired active agent. In a preferred embodiment, the active agent is a retinoid, e.g., Vitamin A(retinol), Vitamin A
aldehyde(retinal), Vitamin A acid(retinoic acid) and derivatives of these compounds, for example, retinyl palmitate, retinyl acetate and the like. Retinoids are readily miscible with the silicone gel, and can be mixed directly into the gel, or as dissolved in an oil-miscible solvent. The retinoid is added to the gel in an amount sufficient to produce about 0.001-5s, more preferably about 0.0l-20, concentration by weight of the total composition to 3o be applied. Although retinoids, especially retinol, are particularly preferred active agents to be stabilized by this method, it will be readily recognized by the skilled artisan that other active agents, such as Vitamin E and derivatives, long-chain alpha hydroxy acids, ceramides, or skin lipids to enhance barrier function can also benefit from combination with a silicone gel.
In addition to the oil-soluble or lipophilic active agents, however, it has surprisingly been discovered that the silicone gel system can also serve to stabilize water-soluble actives. Although not soluble in the silicone gel, it is possible to simply disperse the water-soluble active in the gel, and thereby provide the stabilizing effect which also protects the oil-soluble active. In a preferred 1o embodiment, the water-soluble active is Vitamin C, or a water-soluble derivative thereof, which has useful cosmetic/dermatological properties, such as stimulating collagen synthesis, but which is generally very unstable in formulation. Other useful water-soluble actives which can also be employed are, for example, water soluble preservatives and antioxidants; skin conditioning agents, for example, humectants, such as hyaluronic acid salts, hydrogels, or glycerol or elastin; collagen; alpha-and beta-hydroxy acids; or milk protein. In a preferred embodiment of this invention, the composition comprises at least one oil soluble active and at least one water soluble active.
In a particularly preferred embodiment, the composition comprises the combination of retinol with Vitamin C, which has many benefits to the skin, including collagen stimulation, the Vitamin C being present in an amount of from about 0.1-20% by weight of the total composition.
Although the gel itself is sufficient to stabilize a susceptible active agent against oxygen degradation, it may be desirable to supplement this property with one or more 3o additional antioxidants, preferably lipophilic antioxidants.
Examples of useful antioxidants include Vitamin E and its derivatives, BHT, BHA, NDGA, propyl gallate, and the like.
Tn a preferred embodiment, the antioxidant employed is an oil extract of green tea, this type of extract being more stable than aqueous green tea extracts. The oil soluble green tea extract is employed in an amount of from about 0.0l-15% by weight of the total composition.
Additional components may also be added to the composition, depending upon the intended use of the final product. Examples of such additional components may include, but are not limited to, sunscreens, fragrance, preservatives, emollients, viscosity modifying agents, 1o pigments, and dispersants. The active-containing silicone gel composition can be used as is, or can be further diluted by combination with an appropriate solvent or vehicle, to achieve the desired consistency for application. The vehicle or solvent may be any anhydrous base in which the silicone gel composition is compatible and miscible.
Examples of appropriate bases are volatile or non volatile oils. Suitable volatile oils include cyclic and linear silicones, such as cyclomethicone, octamethylcyclotetrasiloxane, and 2o decamethylcyclopentasiloxane; or straight or branched chain hydrocarbons having from 8-20 carbon atoms, such as decane, dodecane, tridecane, tetradecane, and C8-20 isoparaffins.
Suitable non-volatile oils include vegetable oils, carboxylic acid esters, animal oils, glyceryl esters, non-volatile silicones, and nonvolatile hydrocarbons.
Particularly preferred are the volatile cyclic silicones.
It is desirable in many cases, however, to retain much of the gel-like consistency of the original composition;
therefore, in such a composition, the added base is preferably used in an amount of no more than about 10-150 of the total weight of the composition.
The preferred composition of the present invention is one in which the active component is a retinoid, and most preferably, one in which the retinoid is retinol. These compounds have a number of useful skin-enhancing activities, such as treatment of the symptoms of intrinsic aging, e.g., lines and wrinkles, improvement of skin texture and appearance, prevention or treatment of the symptoms of photoaging, and acne treatment. However, they are extremely susceptible to degradation by a number of external sources, thereby creating significant difficulties in formulating them in such a way as to retain their activity, and to permit the formulations to retain activity over a prolonged 1o storage period. The present retinoid compositions, however, eliminate the need for special formulating conditions, such as dark rooms, nitrogen purging, or separate packaging of the active agent and the vehicle. In preparing the present compositions, the components are simply mixed together under standard conditions. The compositions so prepared show a remarkable stability over time, with the retention of at least about 850, and preferably at least about 900 of the original activity, after a storage period of 8 weeks at room temperature, and as much as 800 or more retained activity 2o even when stored at elevated temperatures(40~C) for 8 weeks.
The present invention will be further illustrated by the following non-limiting examples.
Example I
A composition of the invention is prepared as follows:
Materials Weight o Phase I
Gransil PM-gel(Grant Industries) 85.00*
Phase II
green tea oil extract(LipoChemical) 9.90 retinol 50P base(BASF) 0.l0**
Field of the Invention The present invention relates to cosmetic or pharmaceutical compositions comprising stable active agents.
In particular, the invention relates to compositions in which active agents are stabilized by incorporation into a silicone gel.
1o Backcrround of the Invention In recent times, cosmetics have become developed beyond the concept of mere ornamentation for the face. Consumers now demand more from their makeup than simple color, coverage or moisturizing: it is now preferred that cosmetics provide some benefit to the skin, rather than just decorating it or making it feel softer. This consumer preference has resulted in the frequent use of biologically active ingredients, in many cosmetic products. In view of the now well-recognized damaging effects of sun exposure on 2o the skin, particularly favored active components are those which can counteract or prevent those effects. These components include, for example, sunscreens, antioxidants, and anti-wrinkle agents.
One of the primary difficulties in employing actives in a formulation is the potential instability of the active once incorporated. The very reason for their use in the formulation, i.e., their biological activity, means that they are not inert, and are therefore potentially subject to reduction or loss of potency if not combined with the proper 3o vehicle. A number of routinely encountered factors can readily inactivate a biologically active compound in a formulation before it even reaches the consumer. Such factors include, for example, oxygen, extreme temperatures, WO 99/13859 PCTlUS98/18804 UV light, water, and lipid peroxidases. It is particularly difficult to avoid the effects of oxygen and UV light, which are of course virtually ubiquitous in nature. Although water can technically be avoided by anhydrous formulation, many of the very desirable actives are water soluble, making their incorporation into an anhydrous formulation problematic. Thus, there continues to be a need for development of a cosmetically acceptable vehicle which will be capable of readily incorporating water soluble actives, l0 yet will protect the actives from environmental factors which rob them of their biological activity. The present invention provides a solution to this continuing problem.
Summary of the Invention The present invention provides an anhydrous cosmetic or pharmaceutical formulation for topical application to the skin, the formulation comprising a silicone gel, in combination with a safe and effective amount of one or more biologically active components. The invention also comprises a method of stabilizing a biologically active component, the method comprising combining the active component with a stabilizing amount of a silicone gel. A
preferred active component is a retinoid.
In a preferred embodiment, the formulation also comprises an effective amount of an oil soluble antioxidant.
Detailed Description of the Invention It has now been unexpectedly discovered that it is possible to stabilize biologically active materials by their combination with a silicone gel. The gels employed in the present invention comprise a vehicle in which an organopolysiloxane elastomer is dispersed. The vehicle can comprise any cosmetically acceptable silicone oil, or a combination of silicone oils. The silicone oil may be any volatile or non-volatile silicone oil, for example, any methylated linear or cyclic non-elastomeric organopolysiloxane, or combinations thereof. Preferably, however, the vehicle is a lower molecular weight dimethicone, trimethicone, cyclomethicone, or a mixture of such oils. Preferred silicone oils useful as the gel vehicle in the present invention include, but are not limited to, phenyl trimethicone, or methylated cyclic organopolysiloxanes having ring sizes from 4 to 12, such as to octamethylcyclotetrasiloxane or decamethylpentasiloxane.
The gel is prepared by dispersing in the vehicle an organopolysiloxane elastomer. An elastomer is generally a chain polymer having a degree of cross-linking sufficient to provide a rubber-like material. In the present gel, the elastomer is an at least partially crosslinked or at least partially cured hetero-chain elastomer. Particularly preferred are those which are at least partially cured addition reaction products, i.e., hydrosilation products, or addition polymerization products, of an organopolysiloxane having unsaturated groups, such as vinyl or allyl, preferably bonded to at least one terminal silicon atom, and another silicone compound capable of participation in the addition reaction, such as an organohydrogenpolysiloxane.
Suitable organopolysiloxane elastomers, having a three-dimensional cross-linked structure, are described, for example, in US Patent No. 5,266,321, the contents of which are incorporated herein by reference. However, other suitable elastomer materials are disclosed in, for example, US Patent Nos. 4,980,167 and 4,742,142.
3o A preferred organopolysiloxane is one which is at least partially crosslinked, or is an at least partially cured hetero-chain elastomer. In one preferred embodiment, the organopolysiloxane elastomer is one which is one which is an at least partially cured addition reaction products, i.e., hydrosilation products, or addition polymerization products, of an organopolysiloxane having unsaturated groups, such as vinyl or allyl, preferably bonded to at least one terminal Si atom, and another silicon compound capable of participation in the addition reaction, such as an organohydrogen polysiloxane.
The chosen elastomer is dispersed in the vehicle by known homogenization techniques. The elastomer dispersed in to the vehicle provides a soft, stable viscous gel, or gel-like material. Alternatively, the gel can be purchased premade, with the elastomer already dispersed in the vehicle. Such products are available under the name Gransil, for example Gransil GCM or Gransil PM, from Grant Industries, Inc., Elmwood Park, New Jersey. The amounts of elastomer and vehicle may vary, depending on the desired viscosity, but generally should be in the range of 5-40% elastomer and 60-95o vehicle.
The gel so prepared can be directly combined with the 2o desired active agent. In a preferred embodiment, the active agent is a retinoid, e.g., Vitamin A(retinol), Vitamin A
aldehyde(retinal), Vitamin A acid(retinoic acid) and derivatives of these compounds, for example, retinyl palmitate, retinyl acetate and the like. Retinoids are readily miscible with the silicone gel, and can be mixed directly into the gel, or as dissolved in an oil-miscible solvent. The retinoid is added to the gel in an amount sufficient to produce about 0.001-5s, more preferably about 0.0l-20, concentration by weight of the total composition to 3o be applied. Although retinoids, especially retinol, are particularly preferred active agents to be stabilized by this method, it will be readily recognized by the skilled artisan that other active agents, such as Vitamin E and derivatives, long-chain alpha hydroxy acids, ceramides, or skin lipids to enhance barrier function can also benefit from combination with a silicone gel.
In addition to the oil-soluble or lipophilic active agents, however, it has surprisingly been discovered that the silicone gel system can also serve to stabilize water-soluble actives. Although not soluble in the silicone gel, it is possible to simply disperse the water-soluble active in the gel, and thereby provide the stabilizing effect which also protects the oil-soluble active. In a preferred 1o embodiment, the water-soluble active is Vitamin C, or a water-soluble derivative thereof, which has useful cosmetic/dermatological properties, such as stimulating collagen synthesis, but which is generally very unstable in formulation. Other useful water-soluble actives which can also be employed are, for example, water soluble preservatives and antioxidants; skin conditioning agents, for example, humectants, such as hyaluronic acid salts, hydrogels, or glycerol or elastin; collagen; alpha-and beta-hydroxy acids; or milk protein. In a preferred embodiment of this invention, the composition comprises at least one oil soluble active and at least one water soluble active.
In a particularly preferred embodiment, the composition comprises the combination of retinol with Vitamin C, which has many benefits to the skin, including collagen stimulation, the Vitamin C being present in an amount of from about 0.1-20% by weight of the total composition.
Although the gel itself is sufficient to stabilize a susceptible active agent against oxygen degradation, it may be desirable to supplement this property with one or more 3o additional antioxidants, preferably lipophilic antioxidants.
Examples of useful antioxidants include Vitamin E and its derivatives, BHT, BHA, NDGA, propyl gallate, and the like.
Tn a preferred embodiment, the antioxidant employed is an oil extract of green tea, this type of extract being more stable than aqueous green tea extracts. The oil soluble green tea extract is employed in an amount of from about 0.0l-15% by weight of the total composition.
Additional components may also be added to the composition, depending upon the intended use of the final product. Examples of such additional components may include, but are not limited to, sunscreens, fragrance, preservatives, emollients, viscosity modifying agents, 1o pigments, and dispersants. The active-containing silicone gel composition can be used as is, or can be further diluted by combination with an appropriate solvent or vehicle, to achieve the desired consistency for application. The vehicle or solvent may be any anhydrous base in which the silicone gel composition is compatible and miscible.
Examples of appropriate bases are volatile or non volatile oils. Suitable volatile oils include cyclic and linear silicones, such as cyclomethicone, octamethylcyclotetrasiloxane, and 2o decamethylcyclopentasiloxane; or straight or branched chain hydrocarbons having from 8-20 carbon atoms, such as decane, dodecane, tridecane, tetradecane, and C8-20 isoparaffins.
Suitable non-volatile oils include vegetable oils, carboxylic acid esters, animal oils, glyceryl esters, non-volatile silicones, and nonvolatile hydrocarbons.
Particularly preferred are the volatile cyclic silicones.
It is desirable in many cases, however, to retain much of the gel-like consistency of the original composition;
therefore, in such a composition, the added base is preferably used in an amount of no more than about 10-150 of the total weight of the composition.
The preferred composition of the present invention is one in which the active component is a retinoid, and most preferably, one in which the retinoid is retinol. These compounds have a number of useful skin-enhancing activities, such as treatment of the symptoms of intrinsic aging, e.g., lines and wrinkles, improvement of skin texture and appearance, prevention or treatment of the symptoms of photoaging, and acne treatment. However, they are extremely susceptible to degradation by a number of external sources, thereby creating significant difficulties in formulating them in such a way as to retain their activity, and to permit the formulations to retain activity over a prolonged 1o storage period. The present retinoid compositions, however, eliminate the need for special formulating conditions, such as dark rooms, nitrogen purging, or separate packaging of the active agent and the vehicle. In preparing the present compositions, the components are simply mixed together under standard conditions. The compositions so prepared show a remarkable stability over time, with the retention of at least about 850, and preferably at least about 900 of the original activity, after a storage period of 8 weeks at room temperature, and as much as 800 or more retained activity 2o even when stored at elevated temperatures(40~C) for 8 weeks.
The present invention will be further illustrated by the following non-limiting examples.
Example I
A composition of the invention is prepared as follows:
Materials Weight o Phase I
Gransil PM-gel(Grant Industries) 85.00*
Phase II
green tea oil extract(LipoChemical) 9.90 retinol 50P base(BASF) 0.l0**
Phase III
Ascorbic acid USC-FCC 5.00 *comprising phenyltrimethicone(70%) and organopolysiloxane(30%) **50% solution in Tween 20 Preparation:
1o Phase I is weighed into a primary mixing kettle. In an auxiliary kettle, the Phase II components are mixed under propeller mixer agitation until the solids are completely dissolved; the mixture at this point is slightly cloudy.
The phase III component is then sprinkled over the Phase II
materials, while mixing under propeller mixer agitation.
The uniform dispersion of the combined Phases II and III is confirmed by placing a small sample between glass slides and checking for undispersed ascorbic acid. When the combined Phases II and III are well-dispersed, they are added to 2o Phase I in the primary mixing kettle under mixer agitation, until the combined phases are uniform. The mixture is removed from the kettle through a nylon mesh filter bag, and stored in polyethylene-lined storage containers.
Example II
Compositions prepared according to Example I are then evaluated for their ability to retain activity over a variety of time and temperature storage conditions. In the first instance, the amount of retinol in the compositions is determined, by HPLC, shortly after preparation, and at intervals for up to 8 weeks thereafter, at temperatures of 9~C, 25C, and 40C. The results, showing amount of retinol activity remaining, are shown in Table I.
Ascorbic acid USC-FCC 5.00 *comprising phenyltrimethicone(70%) and organopolysiloxane(30%) **50% solution in Tween 20 Preparation:
1o Phase I is weighed into a primary mixing kettle. In an auxiliary kettle, the Phase II components are mixed under propeller mixer agitation until the solids are completely dissolved; the mixture at this point is slightly cloudy.
The phase III component is then sprinkled over the Phase II
materials, while mixing under propeller mixer agitation.
The uniform dispersion of the combined Phases II and III is confirmed by placing a small sample between glass slides and checking for undispersed ascorbic acid. When the combined Phases II and III are well-dispersed, they are added to 2o Phase I in the primary mixing kettle under mixer agitation, until the combined phases are uniform. The mixture is removed from the kettle through a nylon mesh filter bag, and stored in polyethylene-lined storage containers.
Example II
Compositions prepared according to Example I are then evaluated for their ability to retain activity over a variety of time and temperature storage conditions. In the first instance, the amount of retinol in the compositions is determined, by HPLC, shortly after preparation, and at intervals for up to 8 weeks thereafter, at temperatures of 9~C, 25C, and 40C. The results, showing amount of retinol activity remaining, are shown in Table I.
Table I
Temperature of Storage Time Point 4~C 25C 40C
Initial 0.0420 0.0420 0.0420 1 week 0.038 0.037% 0.0360 2 weeks 0.0390 0.039% 0.0380 4 weeks 0.0390 0.038% 0.034%
8 weeks 0.04l% 0.0400 0.034a to These results show that at low and room temperature conditions, the compositions can retain up to about 90% or more activity after 8 weeks of storage, and even under extreme heat conditions, retains up to about 800 of its initial activity, thereby demonstrating the stabilizing effect of the silicone gel on retinol activity.
The stability of the ascorbic acid in the composition is also evaluated at 4~C, 25C, and 40C. At the end of eight weeks of storage, the compositions show 990, 96o and 950 retention of ascorbic acid activity, indicating a high level of stabilization of this water-soluble active, even in a non-aqueous formulation.
Temperature of Storage Time Point 4~C 25C 40C
Initial 0.0420 0.0420 0.0420 1 week 0.038 0.037% 0.0360 2 weeks 0.0390 0.039% 0.0380 4 weeks 0.0390 0.038% 0.034%
8 weeks 0.04l% 0.0400 0.034a to These results show that at low and room temperature conditions, the compositions can retain up to about 90% or more activity after 8 weeks of storage, and even under extreme heat conditions, retains up to about 800 of its initial activity, thereby demonstrating the stabilizing effect of the silicone gel on retinol activity.
The stability of the ascorbic acid in the composition is also evaluated at 4~C, 25C, and 40C. At the end of eight weeks of storage, the compositions show 990, 96o and 950 retention of ascorbic acid activity, indicating a high level of stabilization of this water-soluble active, even in a non-aqueous formulation.
Claims (15)
1. A cosmetic or pharmaceutical composition for topical application comprising a silicone gel and an effective amount of a retinoid.
2. The composition of claim 1 wherein the gel comprises an organopolysiloxane elastomer and a silicone oil vehicle.
3. The composition of claim 2 in which the elastomer is a reaction product of an organopolysiloxane having an unsaturated group bound to a terminal Si-atom and an organohydrogensiloxane, which reaction product is at least partially cured.
4. The composition of claim 2 in which the silicone oil is a low molecular weight dimethicone, trimethicone, or cyclomethicone.
5. The composition of claim 4 in which the silicone oil is phenyltrimethicone, or octamethylcyclotetrasiloxane.
6. The composition of claim 1 wherein the retinoid is retinol.
7. The composition of claim 1 which also comprises at least one antioxidant.
8. The composition of claim 7 wherein the antioxidant is an oil extract of green tea.
9. The composition of claim 1 which also comprises an effective amount of Vitamin C or a derivative thereof.
10. A cosmetic or pharmaceutical composition for topical application comprising a silicone gel, the gel comprising a (a) an organopolysiloxane elastomer which is a reaction product of an organopolysiloxane having an unsaturated group bound to a terminal Si-atom and an organohydrogensiloxane which reaction product is at least partially cured and (b)a silicone oil selected from the group consisting of a low molecular weight dimethicone, a trimethicone, or a cyclomethicone, combined with (c) an effective amount of a retinoid.
11. The composition of claim 10 wherein the retinoid is retinol.
12. The composition of claim 11 which also comprises an antioxidant.
13. The composition of claim 12 in which the antioxidant is an oil extract of green tea.
14. The composition of claim 10 which also comprises Vitamin C or a derivative thereof.
15. The composition of claim 10 which comprises retinol, an antioxidant, and Vitamin C or a derivative thereof.
16. The composition of claim 15 wherein the silicone oil is phenytrimethicone.
17. The composition of claim 15 wherein the silicone oil is octamethylcyclotetrasiloxane.
18. A method of stabilizing a retinoid which comprises mixing the retinoid with a silicone gel comprising an organopolysiloxane elastomer and a silicone oil vehicle.
19. The method of claim 18 wherein the elastomer is a reaction product of an organopolysiloxane having an unsaturated group bound to a terminal Si-atom and an organohydrogensiloxane which reaction product is at least partially cured.
20. The method of claim 18 wherein the silicone oil is a low molecular weight dimethicone, trimethicone, or cyclomethicone.
21. The method of claim 4 wherein the silicone oil is phenyltrimethicone, or octamethylcyclotetrasiloxane.
22. The method of claim 18 wherein the retinoid is retinol.
23. The method of claim 18 wherein the retinoid and silicone gel are also mixed with an antioxidant.
24. The method of claim 23 wherein the antioxidant is an oil extract of green tea.
25. A method of stabilizing a biologically active agent in a cosmetic or pharmaceutical composition which comprises mixing the agent with a silicone gel comprising an organopolysiloxane elastomer and a silicone oil vehicle.
26. The method of claim 25 wherein the silicone oil is a low molecular weight dimethicone, trimethicone or cyclomethicone.
27. The method of claim 26 wherein the silicone oil is phenyltrimethicone.
28. The method of claim 26 wherein the silicone oil is octamethylcyclotetrasiloxane.
29. The method of claim 25 wherein the composition also comprises an oil extract of green tea.
30. The method of claim 25 wherein the active agent is Vitamin C, or a derivative thereof.
31. A cosmetic or pharmaceutical composition comprising a water soluble biological active, wherein the active is stabilized in the composition by combination with a silicone gel comprising an organopolysiloxane elastomer and a silicone oil vehicle.
32. The composition of claim 15 which is anhydrous.
33. The composition of claim 15 wherein the active is Vitamin C.
34. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 1.
35. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 9.
36. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 10, 37. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 15.
38. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of claim 1.
39. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of claim 9.
40. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of claim 10.
41. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of
15. The composition of claim 10 which comprises retinol, an antioxidant, and Vitamin C or a derivative thereof.
16. The composition of claim 15 wherein the silicone oil is phenytrimethicone.
17. The composition of claim 15 wherein the silicone oil is octamethylcyclotetrasiloxane.
18. A method of stabilizing a retinoid which comprises mixing the retinoid with a silicone gel comprising an organopolysiloxane elastomer and a silicone oil vehicle.
19. The method of claim 18 wherein the elastomer is a reaction product of an organopolysiloxane having an unsaturated group bound to a terminal Si-atom and an organohydrogensiloxane which reaction product is at least partially cured.
20. The method of claim 18 wherein the silicone oil is a low molecular weight dimethicone, trimethicone, or cyclomethicone.
21. The method of claim 4 wherein the silicone oil is phenyltrimethicone, or octamethylcyclotetrasiloxane.
22. The method of claim 18 wherein the retinoid is retinol.
23. The method of claim 18 wherein the retinoid and silicone gel are also mixed with an antioxidant.
24. The method of claim 23 wherein the antioxidant is an oil extract of green tea.
25. A method of stabilizing a biologically active agent in a cosmetic or pharmaceutical composition which comprises mixing the agent with a silicone gel comprising an organopolysiloxane elastomer and a silicone oil vehicle.
26. The method of claim 25 wherein the silicone oil is a low molecular weight dimethicone, trimethicone or cyclomethicone.
27. The method of claim 26 wherein the silicone oil is phenyltrimethicone.
28. The method of claim 26 wherein the silicone oil is octamethylcyclotetrasiloxane.
29. The method of claim 25 wherein the composition also comprises an oil extract of green tea.
30. The method of claim 25 wherein the active agent is Vitamin C, or a derivative thereof.
31. A cosmetic or pharmaceutical composition comprising a water soluble biological active, wherein the active is stabilized in the composition by combination with a silicone gel comprising an organopolysiloxane elastomer and a silicone oil vehicle.
32. The composition of claim 15 which is anhydrous.
33. The composition of claim 15 wherein the active is Vitamin C.
34. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 1.
35. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 9.
36. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 10, 37. A method of preventing or treating the symptoms of intrinsic aging or photoaging on the skin which comprises applying to the skin a composition of claim 15.
38. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of claim 1.
39. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of claim 9.
40. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of claim 10.
41. A method of improving the texture or appearance of the skin which comprises applying to the skin a composition of
claim 15.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US93157297A | 1997-09-16 | 1997-09-16 | |
US08/931,572 | 1997-09-16 | ||
PCT/US1998/018804 WO1999013859A1 (en) | 1997-09-16 | 1998-09-10 | Stable anhydrous formulation |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2270073A1 true CA2270073A1 (en) | 1999-03-25 |
Family
ID=25460997
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002270073A Abandoned CA2270073A1 (en) | 1997-09-16 | 1998-09-10 | Stable anhydrous formulation |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0952818A1 (en) |
JP (1) | JP2001505227A (en) |
KR (1) | KR20000068995A (en) |
AU (1) | AU9311398A (en) |
CA (1) | CA2270073A1 (en) |
WO (1) | WO1999013859A1 (en) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6228894B1 (en) | 1998-04-17 | 2001-05-08 | Enhanced Derm Technologies, Inc. | Softgel-compatible composition containing retinol |
US6146664A (en) * | 1998-07-10 | 2000-11-14 | Shaklee Corporation | Stable topical ascorbic acid compositions |
US6039935A (en) * | 1998-12-30 | 2000-03-21 | Elizabeth Arden Company, Division Of Conopco, Inc. | Sunscreen compositions |
DE19962369A1 (en) * | 1999-12-23 | 2001-06-28 | Beiersdorf Ag | Composition of ascorbyl compound and catechin, or extract containing it, useful for improving barrier properties of skin |
EP1299069B1 (en) | 2000-07-10 | 2005-12-07 | The Procter & Gamble Company | Cosmetic compositions |
KR100479665B1 (en) * | 2002-04-03 | 2005-03-30 | 주식회사 나우코스 | Cosmetic compositions containing fermented extracts of green tea, dehulled rice and taraxacum herb |
US20050239749A1 (en) | 2002-07-25 | 2005-10-27 | Lion Corporation | External preparation |
KR100879133B1 (en) * | 2002-12-23 | 2009-01-19 | 주식회사 엘지생활건강 | Non water-soluble whitening makeup composition and method for preparing therof |
KR20040067710A (en) * | 2003-01-24 | 2004-07-30 | 주식회사 엘지생활건강 | Water-free typed anti-wrinkle cosmetic composition |
WO2007109240A2 (en) | 2006-03-21 | 2007-09-27 | Dow Corning Corporation | Silicone polyether elastomer gels |
WO2007109282A2 (en) | 2006-03-21 | 2007-09-27 | Dow Corning Corporation | Silicone-organic elastomer gels |
EP2194955B1 (en) | 2007-09-26 | 2014-07-16 | Dow Corning Corporation | Silicone organic elastomer gels from organopolysiloxane resins |
US20110306721A1 (en) * | 2010-06-10 | 2011-12-15 | Veerag Mehta | Flame retardant material having enhanced pull through lubricity |
RU2533318C2 (en) | 2010-08-04 | 2014-11-20 | Шлюмбергер Текнолоджи Б.В. | Flow meter system, and measuring method of amount of liquid in multiphase flow with large content of gaseous phase |
US20140219934A1 (en) * | 2013-02-01 | 2014-08-07 | Sandra Senzon | Botanical tooth whitener composition and method for treating discolored or stained teeth |
US9132080B2 (en) * | 2013-03-21 | 2015-09-15 | Julius Zecchino | Delivery system having stabilized ascorbic acid and other actives |
US20140348873A1 (en) * | 2013-05-22 | 2014-11-27 | Professional Compounding Centers Of America | Urea-Silicone Gel for Hyperkeratosis Treatment |
US20140350106A1 (en) * | 2013-05-22 | 2014-11-27 | Professional Compounding Centers Of America | Urea Silicone Gel for Scars and Hydration Treatment and Method of Using Same |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2729850A1 (en) * | 1995-01-30 | 1996-08-02 | Oreal | COSMETIC COMPOSITION COMPRISING A SILICONE COMPOUND AND A FATTY ACID ESTER |
FR2732595A1 (en) * | 1995-04-07 | 1996-10-11 | Oreal | Use of at least one filmogenic polymer in cosmetic or dermatological compsn. for sensitive skin |
US5599548A (en) * | 1995-05-08 | 1997-02-04 | Elizabeth Arden Co., Division Of Conopco, Inc. | Skin care compositions containing fatty acid amides and retinol or retinyl ester |
FR2744911B1 (en) * | 1996-02-19 | 1998-03-20 | Oreal | USE OF AN ELASTOMERIC SOLID ORGANOPOLYSILOXANE COMBINED WITH A FAT PHASE FOR THE PREPARATION OF A COMPOSITION OR IN A CARE OR MAKE-UP COMPOSITION FOR MATIFYING THE SKIN |
US5833973A (en) * | 1996-06-28 | 1998-11-10 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Crosslinked elastomeric silicones in aqueous emulsion cosmetic compositions |
ZA971943B (en) * | 1996-06-28 | 1998-09-07 | Unilever Plc | Vitamin C delivery system |
FR2757380B1 (en) * | 1996-12-24 | 1999-01-29 | Oreal | NON-TRANSFER MAKE-UP OR CARE COMPOSITION CONTAINING ORGANOPOLYSILOXANE AND FAT PHASE |
-
1998
- 1998-09-10 AU AU93113/98A patent/AU9311398A/en not_active Abandoned
- 1998-09-10 EP EP98945997A patent/EP0952818A1/en not_active Withdrawn
- 1998-09-10 CA CA002270073A patent/CA2270073A1/en not_active Abandoned
- 1998-09-10 WO PCT/US1998/018804 patent/WO1999013859A1/en not_active Application Discontinuation
- 1998-09-10 KR KR1019997004324A patent/KR20000068995A/en not_active Application Discontinuation
- 1998-09-10 JP JP51797799A patent/JP2001505227A/en active Pending
Also Published As
Publication number | Publication date |
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WO1999013859A1 (en) | 1999-03-25 |
EP0952818A1 (en) | 1999-11-03 |
AU9311398A (en) | 1999-04-05 |
JP2001505227A (en) | 2001-04-17 |
KR20000068995A (en) | 2000-11-25 |
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