US20070217990A1 - Silicone Vesicles - Google Patents

Silicone Vesicles Download PDF

Info

Publication number
US20070217990A1
US20070217990A1 US10/592,399 US59239905A US2007217990A1 US 20070217990 A1 US20070217990 A1 US 20070217990A1 US 59239905 A US59239905 A US 59239905A US 2007217990 A1 US2007217990 A1 US 2007217990A1
Authority
US
United States
Prior art keywords
water
dispersion
spe
vesicles
organopolysiloxane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/592,399
Other languages
English (en)
Inventor
Shaow Lin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Priority to US10/592,399 priority Critical patent/US20070217990A1/en
Assigned to DOW CORNING CORPORATION reassignment DOW CORNING CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LIN, SHAOW BURN
Publication of US20070217990A1 publication Critical patent/US20070217990A1/en
Priority to US12/339,154 priority patent/US8012387B2/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—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
    • A61K8/02—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
    • A61K8/67—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
    • A61K8/84—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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08J2383/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention provides a process for preparing silicone vesicles by combining and mixing an organopolysiloxane having at least one hydrophilic substituent group, a water miscible volatile solvent, and water.
  • the invention also relates to the vesicle compositions produced by the method and their use in various personal, household, and health care applications.
  • Silicone surfactants have been designed for various applications by combining a hydrophobic organopolysiloxane with various hydrophilic moieties.
  • silicone surfactants known as silicone polyethers are based on copolymer structures of polydimethylsiloxane having pendant polyoxyalkylene groups. Such materials find wide utility in many personal, household, and health care compositions as emulsifiers, wetting agents, and general-purpose aqueous surfactants.
  • silicone vesicles having improved stability.
  • the silicone vesicles formed from the self-assembly procedures can lack durability. This lack of durability can limit the processing conditions they can be subject to in the formation of various finished products.
  • self-assembled silicone vesicles can lack the ability to provide sustained release of loaded actives over an extended period of time.
  • the present inventors have discovered a process to prepare silicone vesicles having improved durability and the ability to release loaded actives over an extended period of time.
  • the present invention provides a process for preparing a vesicle composition comprising;
  • the present invention also relates to the vesicle compositions obtained from the inventive process, and the vesicle compositions further comprising a personal, household, health care ingredient.
  • the present invention further relates to personal, household, health care product compositions containing the vesicle compositions.
  • the first step in the process of the present invention involves combining
  • Component A) is an organopolysiloxane having at least one hydrophilic substituent group.
  • Organopolysiloxanes are well known in the art and are often designated as comprising any number of “M” siloxy units (R 3 SiO 0.5 ), “D” siloxy units (R 2 SiO), “T” siloxy units (RSiO 1.5 ), or “Q” siloxy units (SiO 2 ) where R is independently any hydrocarbon group.
  • the organopolysiloxane has at least hydrophilic substituent. That is, at least one of the R hydrocarbon groups present in the organopolysiloxane is a hydrophilic group.
  • hydrophilic group is the accepted meaning in the art, i.e, designating water loving chemical moieties.
  • the hydrophilic group can be selected from various cationic, anionic, zwitterionic, polyoxyalkylene, oxoazoline chemical moieties that are commonly used in combination with various hydrophobic chemical moieties to create surfactant structures or molecules having surface-active behavior.
  • the amount of the hydrophilic substituent on the organopolysiloxane can vary, depending on the specific chemical component, providing there is at least one hydrophilic group present on the organopolysiloxane.
  • the amount of the hydrophilic groups present in the organopolysiloxane can be described by its weight percent, or in particular, the weight percent of the organopolysiloxane and weight percent of the total hydrophilic groups present in the molecule.
  • the weight percent of the siloxane units in the organopolysiloxane can vary from 20 to 85, alternatively from 30 to 85, or alternatively from 35 to 80 weight percent, while the remaining weight portion of the organopolysiloxane is the hydrophilic group.
  • the organopolysiloxane having at least one hydrophilic substituent group is selected from silicone polyethers.
  • Silicone polyethers generally refer to silicones containing polyether or polyoxyalkylene groups, which encompasses many different structural forms. Two common forms are the rake-type or ABA type.
  • component (A) is a silicone polyether and can have a structure represented by: A cyclic polyether of the type shown below can also be used.
  • R1 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(C 2 H 4 O) b (C 3 H 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.
  • R1 is methyl
  • b 6-12
  • c is zero
  • R3 is hydrogen.
  • the silicone surfactants can be prepared by any of the techniques known in the art, and many are commercially available.
  • rake type SPEs are derived most commonly from hydrosilylating SiH sites of MD x D′ y M with allyloxy-functional polyethers in the presence of Pt catalyst.
  • the process of the present invention is particularly useful to prepare silicone vesicle compositions containing a silicone polyether having silicone/polyether molar ratios such that the silicone polyether aqueous solublility varies from those having only slightly water solublility or dispersiblility to insoluble ones.
  • This silicone/polyether ratio can be represented as value of x/y or x/z in the silicone polyether structures shown above and typically ranges from 5/1 to 50/1, alternatively from 10/1 to 50/1, or alternatively from 20/1 to 50/1.
  • Such silicone polyethers are prepared from a SiH functional organopolysiloxane having a D/D′ ratio ranging from 5/1 to 50/1, alternatively from 10/1 to 50/1 or alternatively from 20/1 to 50/1, where D′ represents a SiH disiloxy unit (for example MeHSiO).
  • Component B) is a water-miscible volatile solvent.
  • water-miscible means the solvent forms a dispersion with water at room temperature for at least several hours.
  • Volatile means the solvent has a higher vapor pressure than water at various temperatures.
  • Suitable water-miscible volatile solvents for vesicle dispersion preparation include organic solvents such as alcohols, ethers, glycols, esters, acids, halogenated hydrocarbons, diols.
  • organic solvents should be miscible with water at the proportion and lower in order to effectively disperse silicones and maintain stable and uniform dispersion overtime.
  • water-miscible alcohols include method, ethanol, propanol, isopropanol, butanol, and higher hydrocarbon alcohols; ethers include gylcol ethers, methyl-ethyl ether, methyl isobutyl ether (MIBK), etc; glycols include propylene glycols, esters include esters of triglycerol, the esterification products of acid and alcohol; halogenated hydrocarbons include chloroform.
  • water-miscible organic solvents are solvents with relatively low boiling points ( ⁇ 100° C.) or high evaporation rate, so they may be removed under vacuum with ease.
  • the most preferred water-miscible organic solvents for this invention are volatile alcohols including methanol, ethanol, isopropanol, and propanol. These alcohols can be removed from aqueous mixtures containing silicone vesicle dispersions via vacuum stripping at ambient temperature.
  • the order of mixing components A), B), and C) is not critical, but typically A) and B) are first mixed and then water added to the mixture. There are no special requirements or conditions needed for effecting the mixing of components A), B), and C).
  • the mixing can be conducted in a batch, semi-continuous, or continuous process.
  • the amount of components A), B), and C) can vary in the process, but typically range as follows;
  • the amount of B) water-miscible volatile solvent used to disperse the organopolysiloxane depends on the type of organopolysiloxane and how much hydrophilic groups are present.
  • the aqueous mixture to effective disperse silicones comprises of 5 to 80 parts of solvent and 20 to 95 parts of water; alternatively 5 to 50 parts of water, or alternatively 10 to 40 parts water.
  • Step II in the process of the present invention is mixing the aqueous dispersion formed in Step I to form vesicles.
  • Mixing techniques can be simple stirring, homogenizing, sonalating, and other mixing techniques known in the art to effect the formation of vesicles in aqueous dispersions.
  • the mixing can be conducted in a batch, semi-continuous, or continuous process.
  • vesicles can be confirmed by techniques common in the state of the art. Typically, vesicles have a lamellar phase structure which exhibit birefringence when examined with a cross polarizing microscope. Alternatively, the formation of vesicles can be demonstrated by Cyro-Transmission Electron Microscopy (Cryo-TEM) techniques. Particle size measurements can also be used to indicate that the organopolysiloxanes are sufficiently dispersed in aqueous medium typical of vesicle sizes. For example, average particle sizes of less than 0.500 ⁇ m (micrometers), are typical for dispersed vesicles. Vesicles having an average particle size of less than 0.200 ⁇ m, or 0.100 ⁇ m are possible with the teachings of the present invention.
  • Step III in the process of the present invention is optional, and involves removing the water miscible volatile solvent, component B).
  • the water miscible volatile solvent is removed by known techniques in the art, such as subjecting the vesicle composition to reduced pressures, while optionally heating the composition.
  • Devices illustrative of such techniques include rotary evaporators and thin film strippers.
  • the present invention also relates to the vesicle compositions produced by the methods, as described supra.
  • the formation of vesicles can be confirmed by techniques common in the state of the art. Typically, vesicles having a lamellar phase structure which exhibit birefringence when examined with a cross polarizing microscope. Alternatively, the formation of vesicles can be demonstrated by Cyro-Transmission Electron Microscopy (Cryo-TEM) techniques. Particle size measurements can also be used to indicate that the organopolysiloxanes are sufficiently dispersed in aqueous medium typical of vesicle sizes For example, average particle sizes of less than 0.500 ⁇ m (micrometers), are typical for dispersed vesicles. Vesicles having a average particle size of less than 0.200 ⁇ m, or 0.100 ⁇ m are possible with the method of the present invention.
  • the present invention further relates to vesicle compositions further comprising a personal, household, or health care ingredient.
  • the vesicle compositions can be used to entrap, and subsequently deliver after application, a personal, household care, or health care ingredient.
  • a listing of possible personal, household, or health care ingredients is taught in WO 03/101412, which is incorporated herein by reference.
  • the personal or health care ingredient can also be selected from a personal or health care “active”, that is, any compound known to have either cosmetic and/or pharmaceutical activity.
  • a representative listing of such personal or health care actives are disclosed in U.S. Pat. No. 6,168,782, which is hereby incorporated by reference.
  • compositions prepared according to the invention can be used in various over-the-counter (OTC) personal care compositions, health care compositions, and household care compositions, but especially in the personal care arena.
  • 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, hair cuticle coats, make-ups, color cosmetics, foundations, blushes, lipsticks, lip balms, eyeliners, mascaras, oil removers, color cosmetic removers, nail polishes, and powders.
  • the vesicle compositions were analyzed via Cyro-TEM techniques according to the following procedure.
  • aqueous sample solution was loaded using a micropipette on a lacey carbon film coated Cu TEM grid that was cleaned and rinsed with acetone and chloroform.
  • the samples were diluted to about 5% solution with de-ionized water.
  • the excess fluid on the grid surface was removed by blotting the surface with a filter paper for 1.5 second to make an aqueous thin film for TEM.
  • the grid was then plunged into a liquid ethane contained in a small vessel located in a larger liquid nitrogen vessel under ⁇ 175° C. atmosphere in the cryo-plunge system to vitrify the water film on the grid and to avoid water crystallization.
  • the quenched sample grid was transferred in to the cryo-grid box in the cryo-plunge system.
  • the grid box containing the sample was transferred into a Gatan cryo-transfer system filled with liquid nitrogen and loaded in a cryo-TEM stage, which has been positioned in the cryo-transfer system and cooled down to below ⁇ 160° C.
  • the sample was loaded in TEM (JEOL 2000FX) and the images were observed at below ⁇ 160° C.
  • the digital images, as shown herein, were taken using a Gatan CCD camera attached at the bottom of the TEM column and Digital Micrograph software.
  • silicone polyethers were prepared, as illustrated in Table 1 below. This series were “rake type” silicone polyethers since they were derived from various dimethyl-methylhydrogen-polysiloxanes of the general formula, MD x D′ y M and allyloxy polyethers.
  • the MD x D′ y M siloxanes were prepared according to known techniques.
  • the silicone polyethers were prepared using well know platinum catalyzed hydrosilylation techniques, such as those disclosed in U.S. Pat. No. 2,823,218.
  • the D/D′ ratio corresponds to x/y ratio in the formula MD x D′ y M and total DP is the sum of x and y.
  • EO7 is allyoxyl poly(ethylene oxide) having about seven EO repeat units
  • EO12 is allyoxyl poly(ethylene oxide) having about 12 EO repeat units; both were obtained from Dow Chemical Company (Midland, Mich.).
  • D/D′ ratio represents the relative ratio of the number of siloxane repeat units to the number of polyether substituted units on the siloxane polyethers, and a direct measure of hydrophobic to hydrophilic ratio of the SPEs. The lower the D/D′ ratio, the more hydrophilic the SPEs, and more readily dispersible the SPE is in water.
  • SPEs were generally found to spontaneously disperse in water, forming vesicles, when the D/D′ was 12 or lower, as summarized in Table 2 below.
  • the D/D′ ratio of the SPE was 15 or higher, the SPEs were less dispersible in water, and the rate of SPE dispersion in water could be very slow to incomplete.
  • This example demonstrates the time needed to disperse SPE 6 (from Example 1) in water and how much faster it disperses when a small amount of isopropanol was present.
  • the SPEs did not spontaneously disperse in water.
  • the SPEs derived from MD 70 D′ 3 M (such as SPE 8) were not dispersible at all in water, even over more than a period of 2 months.
  • Examples 2A and 2B show how SPE 6, a silicone polyether of MD 28.8 D′ 1.22 M siloxane structure dispersed in water alone and in the presence of 5 % isopropanol, respectively. It took about 3 weeks of continuous mixing to form a homogeneous dispersion in water as opposed to less than 1 day when 5 % by weight of isopropanol present in water.
  • FIGS. 1-3 Cryo-TEM images of the vesicles formed in Examples 2A, 2B, and 2D are shown in FIGS. 1-3 respectively. These images show the presence of single lamellar vesicles in Example 2A, and presence of multi-lamellar vesicles in Examples 2B and 2D.
  • a dispersion of SPE 8 in water was attempted by incorporating 10.0 g of SPE 8 into 90.0 g of de-ionized water in a glass jar. The jar was subjected to mixing on a rotowheel mixer. Even after 4 weeks of mixing the SPE remained as separated in water, no dispersion was formed.
  • Example A4 Vesicle Dispersion of 14.4% SPE 8 Dispersion in 28.7% Isopropanol and 56.9% Water
  • a dispersion was prepared by first adding SPE 8 into isopropanol with continuous mixing. Then, water was gradually added with continuous stirring. The resulting final mixture was clear, and a homogenous dispersion. SPE vesicles of 31 nm average sizes were observed and the dispersion has a clear water-like appearance due to the size of the vesicles.
  • Example 4B Vesicle Dispersion of20% SPE 8 in 80.0% Water
  • a homogeneous dispersion of SPE 8 in isopropanol and water was prepared, following a similar procedure for Example 4A. This dispersion was further stripped under vacuum at ambient temperature to remove volatile isopropanol using a Rotovapor. The theoretical amount of 74.93 g of IPA was completely removed and yielded a theoretically alcohol-free aqueous dispersion of SPE 8 vesicles. The resultant product was a milky-white, homogeneous dispersion with an average particle size of 212 nm, as measured by Nanotrac particle analyzer.
  • Example 4C Vesicle Dispersion of 21.2% SPE 8 in 28.8% Isopropanol and 50% Water
  • a homogeneous vesicular dispersion of 21 nm average particle size in isopropanol and water was prepared, following a procedure similar to that of Example 4A.
  • Example 4D Vesicle Dispersion of 29.5% SPE 8 in 1.0% Isopropanol and 69.5% Water
  • Dispersions of SPE 8 in water containing 5% to 20 wt. % isopropanol were prepared according to the procedure described previously, according to the formulations summarized in Table 5.
  • Example 5C was prepared by subjecting the Example 5B dispersion to further vaccum stripping to remove most of the IPA.
  • a homogeneous vesicle dispersion of SPE 7 was made in 20 % IPA and 70 % water having an average dispersion size of only 77 nm, according to the previously described procedure, as summarized as Example 5D.
  • the isopropanol was the removed by vacuum stripping, resulting in a dispersion (Example 5E) having an average dispersion size of only 49 nm in water, as summarized in Table 5.
  • the method of this invention can also be used to entrap and retain oil-soluble substances into vesicles in aqueous dispersions. This is very desirable and beneficial utility of vesicles and vesicular aggregates prepared from silicone polyethers. As many personal care actives & ingredients are not water-soluble or not water-compatible. This makes it not practical to incorporate such ingredients as vitamins, fragrances, sunscreens, and oils directly into water-based or water-continuous end-product formulations, such as creams, lotions, gels, etc.
  • Vitamin A palmitate VAP was first dispersed in isopropanol at 50/50 ratio by weight to keep VAP in a liquid form for ease of mixing.
  • the VAP/IPA was then mixed in with SPE 8, followed by incorporation of isopropanol to form a homogeneous mixture. While under continuous mixing, water was gradually and continuously incorporated into the mixture containing the SPE, VAP and IPA. Then, the mixture was homogenized, using an APV benchtop homogenizer, to further narrow and reduce the dispersion size. The homogenized dispersion was subsequently stripped to remove isopropanol under vaccum at ambient temperature, using a Rotovapor.
  • the 6A example was a partially stripped dispersion having about 10% IPA remaining and an average dispersion size of 0.229 um.
  • the 6B example was a fully stripped dispersion containing 20.8% SPE, 4.5% VAP, 2.2% IPA and 72.5% water.
  • Example 6B was a homogeneous, beige milky dispersion having an average vesicle size of 0.974 um.
  • This dispersion was prepared by first dispersing vitamin A palmitate into SPE 8 in the presence of a small quantity of ethanol. The prescribed amount of ethanol was mixed in with SPE/VAP to form a homogeneous mixture. While under continuous mixing, water was gradually and continuously incorporated into the mixture. A homogeneous mixture was obtained. The mixture was then subjected to vaccum stripping to remove the volatile alcohol. The final dispersion had a composition of 4.5% VAP, 20.7% SPE, 2.9% EtOH and 72.0% water. The dispersion had an average dispersion size of 0.763 um.
  • Ethanol was used as dispersing aid to prepare these VAP loaded SPE vesicles in water dispersions.
  • the procedures followed the ones that used to make Example 6A and 6B, except EtOH used in palce of IPA.
  • the final dispersion compositions are shown in Table 6.
  • the two dispersions had an average dispersion size of 0.284 um and 0.331 um, respectively.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Biophysics (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Medicinal Preparation (AREA)
  • Detergent Compositions (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Silicon Polymers (AREA)
  • Internal Circuitry In Semiconductor Integrated Circuit Devices (AREA)
  • Liquid Crystal (AREA)
US10/592,399 2004-04-20 2005-04-19 Silicone Vesicles Abandoned US20070217990A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/592,399 US20070217990A1 (en) 2004-04-20 2005-04-19 Silicone Vesicles
US12/339,154 US8012387B2 (en) 2004-04-20 2008-12-19 Silicone vesicles

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US56366304P 2004-04-20 2004-04-20
PCT/US2005/013289 WO2005103157A1 (en) 2004-04-20 2005-04-19 Silicone vesicles
US10/592,399 US20070217990A1 (en) 2004-04-20 2005-04-19 Silicone Vesicles

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/013289 A-371-Of-International WO2005103157A1 (en) 2004-04-20 2005-04-19 Silicone vesicles

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/339,154 Continuation-In-Part US8012387B2 (en) 2004-04-20 2008-12-19 Silicone vesicles

Publications (1)

Publication Number Publication Date
US20070217990A1 true US20070217990A1 (en) 2007-09-20

Family

ID=34966168

Family Applications (1)

Application Number Title Priority Date Filing Date
US10/592,399 Abandoned US20070217990A1 (en) 2004-04-20 2005-04-19 Silicone Vesicles

Country Status (8)

Country Link
US (1) US20070217990A1 (zh)
EP (1) EP1756226B1 (zh)
JP (1) JP2007533452A (zh)
KR (1) KR101159053B1 (zh)
CN (5) CN1946374A (zh)
AT (1) ATE442418T1 (zh)
DE (1) DE602005016548D1 (zh)
WO (1) WO2005103157A1 (zh)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070166263A1 (en) * 2004-04-20 2007-07-19 Shaow Lin Vesicles of high molecular weight silicone polyethers
US20070243241A1 (en) * 2004-04-20 2007-10-18 Shaow Lin Silicone Vesicles Containing Actives
US20080226708A1 (en) * 2005-11-01 2008-09-18 Shaow Burn Lin Silicone Vesicles Containing Actives
US20090053301A1 (en) * 2006-02-28 2009-02-26 Shaow Lin Silicone vesicles containing actives
US20100080832A1 (en) * 2007-05-15 2010-04-01 Shiseido Company Ltd. Vesicle-Containing Composition And Production Method Thereof
US7887834B2 (en) 2004-04-20 2011-02-15 Dow Corning Corporation Aqueous dispersions of silicone polyether block copolymers

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1858957B1 (en) * 2005-02-22 2012-02-22 Dow Corning Corporation Polyoxyalkylene-alkyl functional siloxane resins and aqueous compositions thereof
DE602006004757D1 (de) 2005-08-17 2009-02-26 Dow Corning Lyotrope flüssigkristalle und vesikel
JP5186672B2 (ja) * 2006-12-26 2013-04-17 ライオン株式会社 水中油型シリコーンエマルションの製造方法
EP2100582B1 (en) * 2008-03-10 2012-11-28 The Procter & Gamble Company Cosmetic composition
CN101381462B (zh) * 2008-09-10 2011-01-19 中国科学技术大学 一种聚醚嵌段的聚硅氧烷二元醇及其制备方法
JP5960396B2 (ja) * 2011-06-30 2016-08-02 国立大学法人信州大学 ナノカプセルの製造方法
MX2017017029A (es) * 2015-06-30 2018-05-17 Gillette Co Llc Miembro lubricante para cartuchos de rasuradora.
CN115368574B (zh) * 2022-09-21 2023-12-22 江苏美思德化学股份有限公司 改性硅油、制备方法及其应用

Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2823218A (en) * 1955-12-05 1958-02-11 Dow Corning Process for the production of organo-silicon compounds
US4886068A (en) * 1985-07-29 1989-12-12 Kabushiki Kaisha Toshiba Ultrasonic coupling agent
US5364633A (en) * 1994-03-14 1994-11-15 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
US5948855A (en) * 1999-01-12 1999-09-07 Dow Corning Corporation Water-in-oil-in water emulsion
US5958433A (en) * 1995-12-21 1999-09-28 L'oreal Stable dispersion of a water-immiscible phase, in an aqueous phase by means of vesicles based on silicone surfactant
US5958448A (en) * 1995-01-13 1999-09-28 Dow Corning Corporation Siloxane MQ resin vesicles and entrapment
US6120778A (en) * 1995-12-21 2000-09-19 L'oreal Transparent nanoemulsion based on silicone surfactants and use in cosmetics or in dermopharmaceuticals
US6168782B1 (en) * 1999-05-24 2001-01-02 Dow Corning Corporation Elastomeric silicone containing an active ingredient
US20030040571A1 (en) * 2001-07-30 2003-02-27 Feng Qian Jane Clear silicone microemulsions formed spontaneously
US6632420B1 (en) * 2000-09-28 2003-10-14 The Gillette Company Personal care product
US20030220425A1 (en) * 2000-12-18 2003-11-27 Ferritto Michael Salvatore Silicone liquid crystals, vesicles, and gels
US20040076652A1 (en) * 2000-12-15 2004-04-22 Valentina Paspaleeva-Kuhn Vesicle forming skin oils comprising w/o-emusifiers with an hydrophilic-lipophilic balance of 2-6, method for the production and the use thereof
US20040228821A1 (en) * 2003-05-16 2004-11-18 The Procter & Gamble Company Personal care products comprising active agents in a gel network
US6831128B2 (en) * 2001-07-13 2004-12-14 Dow Corning Corporation High solids emulsions of silylated elastomeric polymers
US6902722B2 (en) * 2003-04-14 2005-06-07 L'oreal Aqueous antisun/sunscreen compositions comprising amphiphilic 2-acrylamidomethylpropanesulfonic acid polymers and water-soluble silicones
US6916774B2 (en) * 1998-10-23 2005-07-12 The Procter & Gamble Company Fabric color care method

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR77320B (zh) * 1980-12-22 1984-09-11 Procter & Gamble
DD297249A5 (de) * 1990-08-07 1992-01-02 Veb Mineralwollewerk Flechtingen Bereich F/E Mineralwolle,De Verfahren zur automatischen ueberwachung des aushaertegrades an materialbahnen
JP4700150B2 (ja) * 1999-04-28 2011-06-15 株式会社資生堂 可溶化組成物

Patent Citations (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2823218A (en) * 1955-12-05 1958-02-11 Dow Corning Process for the production of organo-silicon compounds
US4886068A (en) * 1985-07-29 1989-12-12 Kabushiki Kaisha Toshiba Ultrasonic coupling agent
US5364633A (en) * 1994-03-14 1994-11-15 Dow Corning Corporation Silicone vesicles and entrapment
US5411744A (en) * 1994-03-14 1995-05-02 Dow Corning Corporation Silicone vesicles and entrapment
US5958448A (en) * 1995-01-13 1999-09-28 Dow Corning Corporation Siloxane MQ resin vesicles and entrapment
US6120778A (en) * 1995-12-21 2000-09-19 L'oreal Transparent nanoemulsion based on silicone surfactants and use in cosmetics or in dermopharmaceuticals
US5919487A (en) * 1995-12-21 1999-07-06 L'oreal Nanoparticles coated with a lamellar phase based on silicone surfactant and compositions containing them
US5958433A (en) * 1995-12-21 1999-09-28 L'oreal Stable dispersion of a water-immiscible phase, in an aqueous phase by means of vesicles based on silicone surfactant
US6916774B2 (en) * 1998-10-23 2005-07-12 The Procter & Gamble Company Fabric color care method
US7041630B1 (en) * 1998-10-23 2006-05-09 The Procter & Gamble Company Fabric color care method for rejuvenating and/or restoring color to a faded fabric
US5948855A (en) * 1999-01-12 1999-09-07 Dow Corning Corporation Water-in-oil-in water emulsion
US6168782B1 (en) * 1999-05-24 2001-01-02 Dow Corning Corporation Elastomeric silicone containing an active ingredient
US6632420B1 (en) * 2000-09-28 2003-10-14 The Gillette Company Personal care product
US20040076652A1 (en) * 2000-12-15 2004-04-22 Valentina Paspaleeva-Kuhn Vesicle forming skin oils comprising w/o-emusifiers with an hydrophilic-lipophilic balance of 2-6, method for the production and the use thereof
US20030220425A1 (en) * 2000-12-18 2003-11-27 Ferritto Michael Salvatore Silicone liquid crystals, vesicles, and gels
US6831128B2 (en) * 2001-07-13 2004-12-14 Dow Corning Corporation High solids emulsions of silylated elastomeric polymers
US20030040571A1 (en) * 2001-07-30 2003-02-27 Feng Qian Jane Clear silicone microemulsions formed spontaneously
US6902722B2 (en) * 2003-04-14 2005-06-07 L'oreal Aqueous antisun/sunscreen compositions comprising amphiphilic 2-acrylamidomethylpropanesulfonic acid polymers and water-soluble silicones
US20040228821A1 (en) * 2003-05-16 2004-11-18 The Procter & Gamble Company Personal care products comprising active agents in a gel network

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070166263A1 (en) * 2004-04-20 2007-07-19 Shaow Lin Vesicles of high molecular weight silicone polyethers
US20070243241A1 (en) * 2004-04-20 2007-10-18 Shaow Lin Silicone Vesicles Containing Actives
US7678301B2 (en) 2004-04-20 2010-03-16 Dow Corning Corporation Vesicles of high molecular weight silicone polyethers
US20100189667A1 (en) * 2004-04-20 2010-07-29 Shaow Lin Vesicles of high molecular weight silicone polyethers
US7887834B2 (en) 2004-04-20 2011-02-15 Dow Corning Corporation Aqueous dispersions of silicone polyether block copolymers
US20080226708A1 (en) * 2005-11-01 2008-09-18 Shaow Burn Lin Silicone Vesicles Containing Actives
US20090053301A1 (en) * 2006-02-28 2009-02-26 Shaow Lin Silicone vesicles containing actives
US20100080832A1 (en) * 2007-05-15 2010-04-01 Shiseido Company Ltd. Vesicle-Containing Composition And Production Method Thereof

Also Published As

Publication number Publication date
KR101159053B1 (ko) 2012-06-22
CN101671484B (zh) 2012-08-01
ATE442418T1 (de) 2009-09-15
CN101671484A (zh) 2010-03-17
JP2007533452A (ja) 2007-11-22
CN1946770A (zh) 2007-04-11
CN1953731A (zh) 2007-04-25
EP1756226B1 (en) 2009-09-09
WO2005103157A1 (en) 2005-11-03
EP1756226A1 (en) 2007-02-28
CN1946803A (zh) 2007-04-11
DE602005016548D1 (de) 2009-10-22
KR20070004868A (ko) 2007-01-09
CN1946374A (zh) 2007-04-11

Similar Documents

Publication Publication Date Title
EP1756226B1 (en) Silicone vesicles
US20070243241A1 (en) Silicone Vesicles Containing Actives
US7678301B2 (en) Vesicles of high molecular weight silicone polyethers
EP1745087B1 (en) Aqueous dispersions of silicone polyether block copolymers
EP1740148B1 (en) Low molecular weight silicone oil-in-water emulsion
KR20060136466A (ko) 실리콘 폴리에테르 블록 공중합체의 수 분산액
KR20050085379A (ko) 실리콘 계면활성제를 기본으로 하는 극성 유기 오일의 소낭및 마이크로에멀젼 조성물
EP1858957B1 (en) Polyoxyalkylene-alkyl functional siloxane resins and aqueous compositions thereof
US8012387B2 (en) Silicone vesicles
JP4599039B2 (ja) 抗真菌外用組成物
US20180036560A1 (en) Siloxane polymer and actives

Legal Events

Date Code Title Description
AS Assignment

Owner name: DOW CORNING CORPORATION, MICHIGAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:LIN, SHAOW BURN;REEL/FRAME:016612/0186

Effective date: 20050216

STCB Information on status: application discontinuation

Free format text: EXPRESSLY ABANDONED -- DURING EXAMINATION