WO2004050045A1 - Compositions de vesicules et de microemulsion d'huiles polaires organiques a base de tensioactifs silicone - Google Patents

Compositions de vesicules et de microemulsion d'huiles polaires organiques a base de tensioactifs silicone Download PDF

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Publication number
WO2004050045A1
WO2004050045A1 PCT/US2003/038455 US0338455W WO2004050045A1 WO 2004050045 A1 WO2004050045 A1 WO 2004050045A1 US 0338455 W US0338455 W US 0338455W WO 2004050045 A1 WO2004050045 A1 WO 2004050045A1
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WIPO (PCT)
Prior art keywords
surfactant
composition
oil
silicone
organic
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PCT/US2003/038455
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English (en)
Inventor
Randal Hill
Zuchen Lin
Original Assignee
Dow Corning Corporation
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Publication date
Application filed by Dow Corning Corporation filed Critical Dow Corning Corporation
Priority to JP2004557552A priority Critical patent/JP2006513280A/ja
Priority to AU2003293350A priority patent/AU2003293350A1/en
Priority to EP03790299A priority patent/EP1567116A1/fr
Publication of WO2004050045A1 publication Critical patent/WO2004050045A1/fr

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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
    • 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
    • A61K8/068—Microemulsions
    • 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
    • A61K8/14—Liposomes; Vesicles
    • 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
    • A61K8/67—Vitamins
    • A61K8/678—Tocopherol, i.e. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/54—Silicon compounds

Definitions

  • the present invention relates to vesicle and microemulsion compositions comprising a silicone surfactant, a co-surfactant, a polar organic oil, and water.
  • the present invention further relates to a method for forming vesicles from a microemulsion comprising a silicone surfactant, a co-surfactant, a polar organic oil, and water.
  • Vesicles based on silicone surfactants were first disclosed in U.S. Patents 5,364,633 and 5,411,744 by Hill and Snow. The '633 and '744 teaches the preparation of vesicles in water formed solely from certain siloxane surfactants.
  • U.S. 5,958,433 discloses dispersions of a water-immiscible phase, in an external aqueous phase by means of lipid vesicles comprising at least one silicone surfactant.
  • the '433 patent further discloses the use of an ionic amphiphilic lipid for addition to the silicone surfactant to inhibit flocculation of the dispersion.
  • U.S 5,919,487 teaches nanoparticles, and in particular nanocapsules, with a lamellar coating obtained from a silicone surfactant.
  • the nanoparticles of the '487 patent range in size from 10 to 1000 nm and are composed of a polymer encapsulating an oily phase and coated with a lamellar coating comprising at least one silicone surfactant.
  • Silicone surfactants have also been used to prepare microemulsions of silicones, and in particular volatile silicones.
  • U.S. Patents 5,705,562 and 5707,613 to Hill teaches clear silicone microemulsions of volatile silicones that form spontaneously, i.e., without the need for high shearing techniques, based on certain silicone surfactants.
  • U.S 5,623,017 to Hill further teaches clear silicone gels of volatile siloxanes based on silicone surfactants.
  • U.S. 6,120,778 teaches transparent nanoemulsions of various oils based on silicone surfactants.
  • the '778 patent further teaches the addition of amphiphic lipids to its compositions.
  • Commonly assigned co-pending U.S application 09/ 917,322 discloses microemulsions of volatile silicones stabilized by silicone surfactants, and optionally comprising certain co-surfactants.
  • vesicles formed from silicone surfactants can be limited in the amount of substance that can be entrapped in the lamellar phase of the vesicle.
  • active materials such as moisturizers, vitamins are well established.
  • the present inventors have discovered the addition of certain co-surfactants enhances the ability of vesicles based on silicone surfactants to entrap higher loadings of polar organic oils.
  • the present inventors have further discovered the combination of certain co-surfactants and silicone surfactants further provides microemulsion compositions of polar organic oils, based on the selected concentration of the silicone surfactant/co-surfactant, polar organic oil and water.
  • the inventive microemulsion compositions upon dilution with water, produce vesicle-based compositions wherein the polar oil is entrapped with the lamellar phase of the vesicle.
  • compositions comprising a silicone surfactant, a co- surfactant, a polar organic oil, and water.
  • certain concentration ranges of the silicone surfactant, co-surfactant, polar organic oil, and water provide lamellar phase liquid crystalline structured compositions.
  • certain concentration ranges of the silicone surfactant, co-surfactant, polar organic oil, and water provide microemulsion compositions.
  • the present invention further provides a method for forming vesicles containing a silicone surfactant, co-surfactant, polar organic oil, and water comprising first forming a microemulsion of the silicone surfactant, co-surfactant, polar oil, and water, and then diluting the microemulsion with additional water to form vesicles.
  • the present invention relates to compositions comprising;
  • certain concentration ranges, (discussed supra) of the silicone surfactant, co-surfactant, polar organic oil, and water provide lamellar phase liquid crystalline structured compositions. In another embodiment, certain concentration ranges (discussed supra) of the silicone surfactant, co-surfactant, polar organic oil, and water provide microemulsion compositions.
  • Component (A) is a long chain or high molecular weight silicone polyether and can have a structure represented by:
  • a cyclic polyether of the type shown below can also be used.
  • Rl represents an alkyl group containing 1-6 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, and hexyl
  • R2 represents the group - (CH 2 ) a O(C2H4O)b(C3H 6 O) c R3
  • x has a value of 1-1,000, alternatively 1 - 500, or alternatively 10 - 250
  • y has a value of 1-500, alternatively 1- 100, or alternatively 2 - 50
  • z has a value of 1-500, or alternatively 1 - 100
  • m has a value of 3-5
  • n is one
  • a has a value of 3-6
  • b has a value of 4-20
  • c has a value of 0-5
  • R3 is hydrogen, a methyl group, or an acyl group such as acetyl.
  • Rl is methyl; b is 6-12; c is zero; and R3 is hydrogen.
  • the silicone surfactants can be prepared by any of the techniques known in the art, and many are commercially available. Representative commercial silicone surfactants suitable in the present invention include DC 5329 and DC 5211 (Dow Corning Corporation, Midland, MI)
  • Component (B) is a co-surfactant selected from the group of a monohydroxy alcohol, an organic diol, an organic triol, an organic tetraol, a silicone diol, a silicone triol, a silicone tetraol, and a nonionic organic surfactant.
  • cosurfactant component (B) examples include monohydroxy alcohols such as methanol, ethanol, and 2- propanol; organic diols such as ethylene glycol, propylene glycol, and 1, 2 hexanediol; organic triols such as glycerol; organic tetraols such as pentaerythritol and 1,2,3,6-hexane tetraol; and a silicone tetraol such as shown below.
  • monohydroxy alcohols such as methanol, ethanol, and 2- propanol
  • organic diols such as ethylene glycol, propylene glycol, and 1, 2 hexanediol
  • organic triols such as glycerol
  • organic tetraols such as pentaerythritol and 1,2,3,6-hexane tetraol
  • silicone tetraol such as shown below.
  • the nonionic surfactant should be a non-silicon atom containing nonionic emulsifier.
  • the nonionic surfactant are alcohol ethoxylates R4-(OCH2CH2)dOH, and in particular are fatty alcohol ethoxylates.
  • Fatty alcohol ethoxylates typically contain the characteristic group -(OCH2CH2)dOH which is attached to fatty hydrocarbon residue R4 which contains eight to twenty carbon atoms, such as lauryl (C12), cetyl (C ) and stearyl
  • Nonionic surfactants are polyoxyethylene (4) lauryl ether, polyoxyethylene (5) lauryl ether, polyoxyethylene (23) lauryl ether, polyoxyethylene (2) cetyl ether, polyoxyethylene (10) cetyl ether, polyoxyethylene (20) cetyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (10) stearyl ether, polyoxyethylene (20) stearyl ether, polyoxyethylene (21) stearyl ether, polyoxyethylene (100) stearyl ether, polyoxyethylene (2) oleyl ether, and polyoxyethylene (10) oleyl ether.
  • fatty alcohol ethoxylates are commercially available under names such as ALFONIC®, ARLACEL, BRIJ, GENAPOL®, LUTENSOL, NEODOL®, RENEX, SOFTANOL, SURFONIC®, TERGITOL®, TRYCOL, and VOLPO.
  • the co-surfactant can also be selected from cationic organic surfactants.
  • Representative cationic surfactants suitable for use as a co-surfactant in the present invention are described in U.S. 6,071,975, which is hereby incorporated by reference.
  • Preferable cationic surfactants are selected from quaternary ammonium salts containing at least one organic group having at least 6 carbons, or alternatively containing a organic group derived from a fatty alcohol, such as dodecyltrimethylammonium bromide
  • the co-surfactant can also be selected from anionic organic surfactants.
  • anionic organic surfactants suitable for use as a co-surfactant in the present invention are described in U.S. 6,071,975, which is hereby incorporated by reference.
  • the co-surfactant is an organic diol having the general formula R4-CH (OH)CH 2 OH, where R4 is an alkyl hydrocarbon group containing 2 - 20 carbons, alternatively 2 - 12 carbons, or alternatively 2 - 6 carbons.
  • R4 is an alkyl hydrocarbon group containing 2 - 20 carbons, alternatively 2 - 12 carbons, or alternatively 2 - 6 carbons.
  • a preferred organic diol is 1-2 hexanediol.
  • the present invention does not encompass amphiphilic surfactants, as disclosed in U.S. Patents 5,958,433 and 6,120,778 as a possible selection of co-surfactant (B).
  • Component (C) is a polar organic oil.
  • a polar organic oil is any oil, or combination of oils.
  • the polar organic oil is derived from an animal, a vegetable, or a mineral source.
  • Modern cosmetic oils are most representative of the polar organic oil, and among the more common organic oils known to be safe for cosmetic purposes are almond oil, apricot kernel oil, avocado oil, cacao butter (theobroma oil), carrot seed oil, castor oil, citrus seed oil, coconut oil, corn oil, cottonseed oil, cucumber oil, egg oil, jojoba oil, lanolin oil, linseed oil, mineral oil, mink oil, olive oil, palm kernel oil, peach kernel oil, peanut oil, rapeseed oil, safflower oil, sesame oil, shark liver oil, soybean oil, sunflower seed oil, sweet almond oil, tallow (beef) oil, tallow (mutton) oil, turtle oil, vegetable oil, whale oil, and wheat germ oil.
  • Polar organic oils does not encompass silicone oils, that is oils based on polyorganosiloxanes.
  • RETINOL includes trans- RETINOL, 13-cis-RETINOL, 11-cis-RETINOL, 9-cis-RETINOL, and 3,4-didehydro- RETINOL.
  • Other vitamins which are appropriate include RETINYL ACETATE, RETINYL PALMITATE, RETINYL PROPIONATE, -TOCOPHEROL, TOCOPHERSOLAN, TOCOPHERYL ACETATE, TOCOPHERYL LINOLEATE, TOCOPHERYL NICOTINATE, and TOCOPHERYL SUCCINATE.
  • the polar oil is vitamin E or an ester of vitamin E.
  • Components (A), (B), (C) and (D) can be combined at various weight percentages to produce compositions that are either i) vesicles having a lamellar phase structure or, ii) clear microemulsions.
  • lamellar phase describes the nature of the vesicle composition and is the accepted meaning in the art.
  • clear microemulsion describes a emulsion composition containing particles that are smaller than the wavelength of light.
  • the microemulsion compositions of the present invention are be further defined by the definitions and requirements set forth in U.S. 5,705,562, which is hereby incorporated by reference.
  • compositions that are either i) vesicles having a lamellar phase structure or, ii) clear microemulsions can be done using a ternary phase diagram.
  • compositions are prepared by simply combining components (A), (B), (C) and (D) at various weight percentages. Excessive use of shearing techniques, or complicated mixing techniques are not necessary.
  • the various components described infra are combined in a single container, shaken, or alternatively mixed with common lab mixers.
  • the resulting composition is then characterized as being either a single-phase system, i.e. a clear microemulsion, or a two- phase system, i.e.
  • vesicles dispersed in water in which the vesicles have a lamellar phase structure.
  • the formation of vesicles can be confirmed by techniques common in the state of the art. Typically, vesicles having a lamellar phase structure exhibit birefringence when examined with a cross polarizing microscope.
  • a data point is recorded on the ternary phase diagram designating that composition as being either as single- phase system or two-phase system.
  • a representative example of a ternary phase diagram is shown in figure 1. In figure 1, compositions producing one- phase systems, i.e.
  • microemulsions were designated by a spherical dot mark, whereas the compositions producing a two-phase system were designated by a triangular mark. Typically, a boundary line is found that separates the one phase and two-phase systems. Thus, it is typical to investigate many compositions that lie on or near the boundary of the phases to establish each region in the ternary phase diagram for any given combination of components.
  • the first embodiment of the present invention provides vesicle compositions comprising;
  • Rl represents an alkyl group containing 1-6 carbon atoms
  • R2 represents the group -(CH2) a O(C 2 H4 ⁇ )b(C3H6 ⁇ ) c R3;
  • a co-surfactant selected from the group of a monohydroxy alcohol, an organic diol, an organic triol, an organic tetraol, a silicone diol, a silicone triol, a silicone tetraol, an cationic organic surfactant, an anionic organic surfactant, and an nonionic organic surfactant;
  • the vesicle composition has a lamellar phase liquid crystalline structure.
  • the polar oil is entrapped in the lamellar phase liquid crystalline structure of the vesicle.
  • the vesicle composition can contain as much as 20 weight %, alternatively 40 weight %, or alternatively 50 weight % of the polar organic oil wherein the polar organic oil is entrapped in the lamellar phase structure of the vesicle.
  • the second embodiment of the present invention provides microemulsion compositions comprising;
  • Rl represents an alkyl group containing 1-6 carbon atoms
  • R2 represents the group -(CH2) a O(C2H4O) (C 3 H 6 O) c R3;
  • a co-surfactant selected from the group of a monohydroxy alcohol, an organic diol, an organic triol, an organic tetraol, a silicone diol, a silicone triol, a silicone tetraol, an cationic organic surfactant, an anionic organic surfactant, and an nonionic organic surfactant;
  • composition is a clear microemulsion composition.
  • the weight ratio of components (A) to (B) can vary from 30:70 to 70:30, alternatively from 40:60 to 60:40, or alternatively from 45:55 to 55:45.
  • Figure 1 shows a ternary phase diagram for compositions formed from the combinations of a 50/50 weight/weight mixture of a silicone surfactant (DC 5329, Dow
  • compositions of the present invention that can be formed from components (A) - (D) as defined infra.
  • the region labeled as a one-phase system define the concentrations of components (A) - (D) that produced microemulsion compositions, whereas the region labeled as a two phase system define the concentrations of components (A) - (D) that produced vesicles having the vitamin E entrapped with the lamellar phase structure of the vesicle.
  • organic polar oils can be selected for component (C), for example substituted or used in place of vitamin E from the example described in figure 1.
  • component (C) for example substituted or used in place of vitamin E from the example described in figure 1.
  • Each organic polar oil selected will produce a unique ternary phase diagram, given any combination of components (A), (B) and (D).
  • figure 2 shows the ternary phase diagram for the combinations of a 50/50 weight/weight mixture of a silicone surfactant (DC 5329, Dow Corning Corporation, Midland, MI) and a co-surfactant, (C 6 H ⁇ 3 (CH 2 CH 2 O) 2 , designated as C6E2 in figure 2 , a polar organic oil (vitamin E), and water.
  • a silicone surfactant DC 5329, Dow Corning Corporation, Midland, MI
  • C 6 H ⁇ 3 (CH 2 CH 2 O) 2 designated as C6E2 in figure 2
  • vitamin E a polar organic oil
  • concentrations of components (A), (B) and (D) for any given polar organic oil (C), given the teaching of the present invention.
  • the present invention further provides a method for forming vesicles containing a silicone surfactant, co-surfactant, polar organic oil, and water comprising first forming a microemulsion of (A) a silicone surfactant, (B) a co-surfactant, (C) an organic polar oil, and (D) water, and then diluting the microemulsion with additional water to form vesicles.
  • Components (A) - (D) are the same as defined infra.
  • the microemulsion formed from components (A) — (D) is the same as defined above, and designated as a one-phase system in the ternary phase diagram.
  • the formed microemulsion is then diluted with additional water to form vesicles (as defined infra) wherein the polar organic oil is entrapped in the lamellar phase of the vesicles.
  • the microemulsions and vesicles prepared according to the invention can be used in various over-the-counter (OTC) personal care products.
  • OTC over-the-counter
  • they can be used in antiperspirants, deodorants, skin creams, skin care lotions, moisturizers, facial treatments such as acne or wrinkle removers, personal and facial cleansers, bath oils, perfumes, colognes, sachets, sunscreens, pre-shave and after-shave lotions, liquid soaps, shaving soaps, shaving lathers, hair shampoos, hair conditioners, hair sprays, mousses, permanents, depilatories, cuticle coats, make-ups, color cosmetics, foundations, blushes, lipsticks, lip balms, eyeliners, mascaras, oil removers, color cosmetic removers, and powders.
  • the microemulsion compositions are also useful as carriers for pharmaceuticals, biocides, herbicides, pesticides, and to incorporate water and water-soluble substances into hydrophobic
  • vesicle and microemulsion compositions of the present invention can be combined with various other components to prepare the personal care products described infra.
  • these components include additional surfactants, moisturizers, pigments, sunscreens, fragrances, emollients, commonly used to formulate such personal care products.
  • Example I A silicone polyether (DC 5329, Dow Corning Corporation, Midland, MI) 1 part, and
  • Example IV 1 part vitamin E acetate and 4 parts DC 5329 were added to a vial, and this was rotated overnight. Using the 6% 1,2-hexanediol aqueous dispersion prepared in Example III, 1 part of the 20% vitamin E acetate in DC 5329 solution was combined with 99 parts 6% 1,2- hexanediol in water in a vial. This sample was rotated overnight, and particle size data revealed peaks at 2.761 ⁇ m and 0.381 ⁇ m. This resulted in smaller particle size distribution (compare to Example V).
  • Example V comparativative
  • a 50/50 mixture of DC 5329 and 1,2-hexanediol was made by heating the DC 5329 for 45 seconds in a microwave oven and then adding the 1,2-hexanediol. The mixture was shaken and spun on a rotary wheel (Roto-Torque, Model # 7637-01) for thirty minutes. The 50/50 mixture was used at room temperature.
  • a triangular graph was used to determine the desired percentages of each of the three components to be used.
  • samples of total mass three grams were prepared. For example, 1.86 g of surfactant was first weighed into a Pyrex tube vial (13x100 mm), then 0.09 g of deionized water was added and finally 1.05 g of Vitamin E (Fluka Chemical, # 355472/1 11098). Other samples made include 1.23 g of surfactant, 0.75 g of deionized water and
  • the sample tube vials were labeled and spun on the rotary wheel for ten minutes, and all formed clear microemulsions. Microemulsions were also formed when Vitamin E was replaced with other polar oils.
  • the successful compositions included 2.25 g of surfactant, 0.3 g deionized water and 0.45 g of Isopropylpalmitate (Lot # 97D31) and 1.5 g of surfactant, 0.9 g deionized water and 0.6 g of 1-octanol (Analysis # 366507/1 51697).
  • FIG. 3 is the transmission electron micrograph (TEM) image of the formed vesicles.
  • a microemulsion composed of 35% 2-5329/1 ,2-Hexanediol (50/50), 40% H2O, and 10% Vitamin was prepared by the method above. It was further diluted (1 :7 dilution) in H2O. TEM image showed vesicle formation, as shown in figure 4.

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Abstract

L'invention concerne des compositions de vésicules et de microémulsion contenant un agent tensioactif siliconé, un co-agent tensioactif, une huile organique polaire, et de l'eau. Elle concerne aussi un procédé de formation de vésicules à partir d'une d'un microémulsion comportant un agent tensioactif siliconé, un co-agent tensioactif, une huile organique polaire, et de l'eau. Les compositions de vésicules et de microémulsion sont utiles dans une variété d'applications personnelles de soin.
PCT/US2003/038455 2002-12-04 2003-12-03 Compositions de vesicules et de microemulsion d'huiles polaires organiques a base de tensioactifs silicone WO2004050045A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2004557552A JP2006513280A (ja) 2002-12-04 2003-12-03 シリコーン界面活性剤に基づく極性有機油のベシクル及びミクロエマルション組成物
AU2003293350A AU2003293350A1 (en) 2002-12-04 2003-12-03 Vesicle and microemulsion compositions of polar organic oils based on silicone surfactants
EP03790299A EP1567116A1 (fr) 2002-12-04 2003-12-03 Compositions de vesicules et de microemulsion d'huiles polaires organiques a base de tensioactifs silicone

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US43114102P 2002-12-04 2002-12-04
US60/431,141 2002-12-04

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WO2004050045A1 true WO2004050045A1 (fr) 2004-06-17

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JP (1) JP2006513280A (fr)
KR (1) KR20050085379A (fr)
CN (1) CN1720021A (fr)
AU (1) AU2003293350A1 (fr)
WO (1) WO2004050045A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005102248A2 (fr) * 2004-04-20 2005-11-03 Dow Corning Corporation Liposomes de silicone contenant des principes actifs
WO2005102006A1 (fr) * 2004-04-20 2005-11-03 Dow Corning Corporation Liposomes de silicone-polyethers a masse moleculaire elevee
WO2005123028A1 (fr) * 2004-06-08 2005-12-29 Dow Global Technologies Inc. Composition de parfum aqueuse exempte d'ethanol
EP1779835A1 (fr) * 2005-10-25 2007-05-02 Beiersdorf AG Émulsion comprenant 1, 2-alkanediols et des huiles polaires
WO2007048757A1 (fr) * 2005-10-25 2007-05-03 Beiersdorf Ag Preparation cosmetique se presentant sous la forme d'une emulsion huile dans eau contenant de l'alcanediol 1,2
EP1792603A1 (fr) * 2005-10-25 2007-06-06 Beiersdorf AG Une émulsion cosmétique huile/eau comprenant 1,2-hexanediol
WO2007053424A3 (fr) * 2005-11-01 2007-06-28 Dow Corning Liposomes de silicone contenant des principes actifs
WO2007100416A1 (fr) * 2006-02-28 2007-09-07 Dow Corning Corporation Vesicules de silicone contenant des agents actifs
US7816479B2 (en) 2005-02-22 2010-10-19 Dow Corning Corporation Polyoxyalkylene-alkyl functional siloxane resins and aqueous compositions thereof
US7887834B2 (en) 2004-04-20 2011-02-15 Dow Corning Corporation Aqueous dispersions of silicone polyether block copolymers
US8012387B2 (en) 2004-04-20 2011-09-06 Dow Corning Corporation Silicone vesicles
EP2561862A1 (fr) * 2010-03-31 2013-02-27 Shiseido Company, Ltd. Composition contenant des vésicules
US8734840B2 (en) 2006-12-28 2014-05-27 Dow Corning Corporation Polynuclear microcapsules
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent
US9687425B2 (en) 2014-06-30 2017-06-27 The Procter & Gamble Company Personal care compositions and methods
US9717930B2 (en) 2013-03-12 2017-08-01 The Procter & Gamble Company Antiperspirant compositions
US9877909B2 (en) 2014-06-30 2018-01-30 The Procter & Gamble Company Personal care compositions and methods
US10016343B2 (en) 2013-03-12 2018-07-10 The Procter & Gamble Company Solid stick antiperspirant compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5121179B2 (ja) * 2006-07-25 2013-01-16 株式会社 資生堂 ベシクル含有組成物及びその製造方法
ES2612005T3 (es) * 2007-05-15 2017-05-11 Shiseido Company, Ltd. Composición conteniendo vesículas, y procedimiento para la fabricación de la misma
JP2015534944A (ja) * 2012-10-11 2015-12-07 ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ 水性シリコーンポリエーテルマイクロエマルジョン

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299112A (en) * 1964-06-19 1967-01-17 Union Carbide Corp Siloxane wetting agents
EP0313304A2 (fr) * 1987-10-22 1989-04-26 The Procter & Gamble Company Compositions photoprotectrices contenant du sorbate de tocophérol
WO1991007943A1 (fr) * 1989-12-01 1991-06-13 The Gillette Company Gels de rasage a pouvoir moussant apres application
US5411744A (en) * 1994-03-14 1995-05-02 Dow Corning Corporation Silicone vesicles and entrapment
WO1997030690A1 (fr) * 1996-02-23 1997-08-28 Unilever Plc Traitement de la peau avec des esters de l'acide salicylique
US5919487A (en) * 1995-12-21 1999-07-06 L'oreal Nanoparticles coated with a lamellar phase based on silicone surfactant and compositions containing them
US6120778A (en) * 1995-12-21 2000-09-19 L'oreal Transparent nanoemulsion based on silicone surfactants and use in cosmetics or in dermopharmaceuticals

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299112A (en) * 1964-06-19 1967-01-17 Union Carbide Corp Siloxane wetting agents
EP0313304A2 (fr) * 1987-10-22 1989-04-26 The Procter & Gamble Company Compositions photoprotectrices contenant du sorbate de tocophérol
WO1991007943A1 (fr) * 1989-12-01 1991-06-13 The Gillette Company Gels de rasage a pouvoir moussant apres application
US5411744A (en) * 1994-03-14 1995-05-02 Dow Corning Corporation Silicone vesicles and entrapment
US5919487A (en) * 1995-12-21 1999-07-06 L'oreal Nanoparticles coated with a lamellar phase based on silicone surfactant and compositions containing them
US6120778A (en) * 1995-12-21 2000-09-19 L'oreal Transparent nanoemulsion based on silicone surfactants and use in cosmetics or in dermopharmaceuticals
WO1997030690A1 (fr) * 1996-02-23 1997-08-28 Unilever Plc Traitement de la peau avec des esters de l'acide salicylique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
R.G. ALANY ET AL.: "Effects of alcohols and diols on the phase behaviour of quaternary systems", INTERNATIONAL JOURNAL OF PHARMACEUTICS, no. 196, 2000, pages 141 - 145, XP002276790 *

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7678301B2 (en) 2004-04-20 2010-03-16 Dow Corning Corporation Vesicles of high molecular weight silicone polyethers
WO2005102006A1 (fr) * 2004-04-20 2005-11-03 Dow Corning Corporation Liposomes de silicone-polyethers a masse moleculaire elevee
WO2005102248A3 (fr) * 2004-04-20 2006-01-05 Dow Corning Liposomes de silicone contenant des principes actifs
US8012387B2 (en) 2004-04-20 2011-09-06 Dow Corning Corporation Silicone vesicles
US7887834B2 (en) 2004-04-20 2011-02-15 Dow Corning Corporation Aqueous dispersions of silicone polyether block copolymers
WO2005102248A2 (fr) * 2004-04-20 2005-11-03 Dow Corning Corporation Liposomes de silicone contenant des principes actifs
WO2005123028A1 (fr) * 2004-06-08 2005-12-29 Dow Global Technologies Inc. Composition de parfum aqueuse exempte d'ethanol
US8343521B2 (en) 2004-06-08 2013-01-01 Dow Global Technologies, Llc Ethanol-free aqueous perfume composition
US7816479B2 (en) 2005-02-22 2010-10-19 Dow Corning Corporation Polyoxyalkylene-alkyl functional siloxane resins and aqueous compositions thereof
EP1779835A1 (fr) * 2005-10-25 2007-05-02 Beiersdorf AG Émulsion comprenant 1, 2-alkanediols et des huiles polaires
US7875653B2 (en) 2005-10-25 2011-01-25 Beiersdorf Ag Emulsion comprising 1,2-alkanediols and polar oil components
EP1792603A1 (fr) * 2005-10-25 2007-06-06 Beiersdorf AG Une émulsion cosmétique huile/eau comprenant 1,2-hexanediol
WO2007048757A1 (fr) * 2005-10-25 2007-05-03 Beiersdorf Ag Preparation cosmetique se presentant sous la forme d'une emulsion huile dans eau contenant de l'alcanediol 1,2
US8084507B2 (en) 2005-10-25 2011-12-27 Beiersdorf Ag Cosmetic O/W emulsion comprising 1,2-hexanediol
DE102005051862B4 (de) 2005-10-25 2018-08-30 Beiersdorf Ag Emulsion enthaltend 1,2-Alkandiole, Emulgatoren und polare Ölkomponenten sowie deren Verwendung
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
WO2007053424A3 (fr) * 2005-11-01 2007-06-28 Dow Corning Liposomes de silicone contenant des principes actifs
WO2007100416A1 (fr) * 2006-02-28 2007-09-07 Dow Corning Corporation Vesicules de silicone contenant des agents actifs
US8734840B2 (en) 2006-12-28 2014-05-27 Dow Corning Corporation Polynuclear microcapsules
EP2561862A4 (fr) * 2010-03-31 2013-10-30 Shiseido Co Ltd Composition contenant des vésicules
EP2561862A1 (fr) * 2010-03-31 2013-02-27 Shiseido Company, Ltd. Composition contenant des vésicules
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent
US10016343B2 (en) 2013-03-12 2018-07-10 The Procter & Gamble Company Solid stick antiperspirant compositions
US9717930B2 (en) 2013-03-12 2017-08-01 The Procter & Gamble Company Antiperspirant compositions
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JP2006513280A (ja) 2006-04-20

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