WO2014184660A2 - Stabilisation d'émulsion - Google Patents

Stabilisation d'émulsion Download PDF

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Publication number
WO2014184660A2
WO2014184660A2 PCT/IB2014/001487 IB2014001487W WO2014184660A2 WO 2014184660 A2 WO2014184660 A2 WO 2014184660A2 IB 2014001487 W IB2014001487 W IB 2014001487W WO 2014184660 A2 WO2014184660 A2 WO 2014184660A2
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WIPO (PCT)
Prior art keywords
chosen
solution
active agent
surface active
particles
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PCT/IB2014/001487
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English (en)
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WO2014184660A3 (fr
Inventor
Vance Bergeron
Jean-Thierry Simonnet
Florence Levy
Aurelie Lafuma
Stephane SANTUCCI
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L'oreal
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Priority claimed from US13/896,663 external-priority patent/US20140341954A1/en
Priority claimed from US13/896,646 external-priority patent/US10028895B2/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2014184660A2 publication Critical patent/WO2014184660A2/fr
Publication of WO2014184660A3 publication Critical patent/WO2014184660A3/fr

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • 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
    • C09K23/002—Inorganic 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

Definitions

  • the disclosure relates to oil-in-water (“O/W”) emulsions useful in a variety of applications, and methods for preparing O/W emulsions.
  • O/W emulsions according to the disclosure may exhibit improved stability over an extended period of time, such as for several months, even when stored at room temperature.
  • One such method utilizes amphiphilic polymers, but this technique is limited in that it is only useful in certain emulsions where the amphiphilic polymer is compatible with the oil phase of the emulsion, or where polymer interactions do not disrupt the rheological behavior of the emulsion.
  • a second method utilizes particles, typically inorganic, to form a Pickering emulsion as known in the state of the art. This technique likewise has drawbacks in that the particles must be carefully chosen such that they are compatible with the oil phase of the emulsion and that the properties of the particles do not adversely affect the emulsion.
  • U.S. Patent Nos. 6,159,453 and 6,238,650 describe sol-gel microcapsules comprising sunscreen active ingredients
  • U.S. Patent Publication No. 2008/199526 describes compositions comprising two sunscreen agents encapsulated within microcapsules having a specific diameter
  • U.S. Patent No. 8,1 10,284 describes microcapsules having a core material encapsulated within a microcapsular shell, wherein the core material comprises an active ingredient.
  • 201 1/293677, and 201 1/31 1723 all describe silica shell techniques. These techniques have a drawback, however, in that the shell is made by a process that releases harmful by-products, which for both human and environmental safety reasons, is desired to be avoided.
  • EP1627668 for the formation and stabilization of emulsions using particles and low amounts of non-ionic surfactant.
  • non-ionic surfactant does not allow for electrostatic interaction.
  • US 2009/0325780 discloses stabilization of foams and emulsions using partially lyophobic and lyophilized particles. However, it is required to combine the particles in solution with amphiphilic molecules in order to make them hydrophobic before preparing the foam or emulsion. The resulting interfacial adhesion of particles to the surface of the oil droplet, however, is discrete, and somewhat discontinuous, as seen in FIG. 1.
  • O/W emulsions may allow for the formation of a rigid interface between the oil and water phases.
  • the preparation methods according to various embodiments can result in a tightly packed, continuous layer of particles encapsulating the oil droplets and/or the oil droplets can be individually encapsulated, which may prevent coalescence or so-called Oswald-ripening, resulting in increased stability.
  • emulsions can be prepared by mixing a solution and an O/W dispersion, where the dispersed phase comprises oil droplets and the continuous phase comprises a surface- active material at the oil-water interface, by any method known.
  • the surface-active material can be chosen to impart a charge at the O/W interface. Subsequently, a solution comprising particles having a charge opposite to that of the surface-active material can be added. According to further embodiments, a solution of silicate salts may be separately prepared and the pH adjusted so that silicic acid is produced, creating anionic complexes that are attracted to the cationic surface of the oil droplets. These processes may lead to encapsulation of the oil droplets, and O/W emulsions having improved stability over extended periods of time.
  • FIG. 1 is a schematic of a prior art encapsulation process
  • FIG. 2 is a schematic of an exemplary encapsulation process, according to an embodiment of the disclosure.
  • FIG. 3 is a micrograph showing encapsulated oil droplets prepared according to an exemplary embodiment of the disclosure.
  • FIG. 4 is a schematic of a process for encapsulating oil droplets, according to an exemplary embodiment of the disclosure.
  • the disclosure relates to O/W emulsions prepared via silicic acid complexation and/or particle adsorption by electrostatic interaction, and methods of preparing such emulsions comprising mixing an O/W dispersion and a solution.
  • the processes for preparing the O/W emulsions may, in various embodiments, comprise steps of preparing an O/W dispersion, where the dispersed phase (oil phase) comprises oil droplets, and the continuous phase comprises a surface-active material at the oil-water interface.
  • This may be done by any method known, such as, for example, by high speed blender (e.g. ultra turrax), rotor-stator, high pressure homogenizer, static mixer, in-line mixer, etc.
  • the O/W dispersion comprises, for example, about 5% to about 50%, such as about 5% to about 40%, about 10% to about 50%, about 10% to about 40%, about 15% to about 50%, about 15% to about 40%, about 5% to about 35%, about 10% to about 35%, about 15% to about 35%, such as about 20% to about 30%, of the dispersed (oil) phase, in the form of droplets.
  • the oil droplets of the dispersed phase may, according to various embodiments, be in the range of micron-sized.
  • the droplets may range up to about 1000 ⁇ , such as up to about 750 ⁇ , such as up to about 500 ⁇ , up to about 250 ⁇ , or up to about 100 ⁇ .
  • the droplets may range from about 0.05 ⁇ to about 500 ⁇ , such as about 0.1 ⁇ to about 500 ⁇ , about 0.5 ⁇ to about 500 ⁇ , about 1 ⁇ to about 500 ⁇ , about 5 ⁇ to about 500 ⁇ , about 0.1 ⁇ to about 250 ⁇ , about 0.5 ⁇ to about 250 ⁇ , about 1 ⁇ to about 250 ⁇ , about 5 ⁇ to about 250 ⁇ , about 0.1 ⁇ to about 100 ⁇ , about 0.5 ⁇ to about 100 ⁇ , about 1 ⁇ to about 100 ⁇ , or about 5 ⁇ to about 100 ⁇ .
  • the droplets may range up to about 50 ⁇ , such as from about 1 ⁇ to about 50 ⁇ , such as about 1 ⁇ to about 10 ⁇ , about 5 ⁇ to about 50 ⁇ , about 5 ⁇ to about 20 ⁇ , or about 5 ⁇ to about 10 ⁇ .
  • the dispersed phase may comprise any type of natural or synthetic oil that may be useful according to the industry or application of interest.
  • the oils may be chosen from triglycerides, esters, ethers, silicones, volatile oils, or combinations thereof.
  • oily compounds such as, for example, sunscreen filters, vitamins, and lipophilic or other molecules that may be dissolved in oil may be used.
  • milk and milk derivatives may be used, for example in food applications.
  • the continuous phase may be aqueous, and may comprise at least one surface active agent, which may, in at least certain embodiments, cover the oil droplets at the O/W interface.
  • the at least one surface active agent may be chosen from cationic surface active agents, as well as from amphoteric surface active agents, amphiphilic polymers, anionic surfactants, molecules that may be pH-adjusted such that they become cationic, and any mixture thereof.
  • the surface-active agent When the surface-active agent covers the oil droplet, it imparts a charge to the coated oil droplet.
  • the coated oil droplet may have a charge greater than about 40 mV, such as greater than about 50 mV, greater than about 60 mV, greater than about 70 mV, greater than about 80 mV, greater than about 90 mV, or greater than about 100 mV.
  • the at least one surface active agent may be present in an amount ranging from about 0.5 to about 50 times the Critical Micellar Concentration ("CMC") of the emulsion, such as, for example, about 0.5 to about 40 times the CMC, about 1 to about 40 times the CMC, about 1 to about 25 times the CMC, or about 1 to about 15 times the CMC.
  • CMC Critical Micellar Concentration
  • Exemplary, non-limiting cationic surface active agents include optionally polyoxyalkylenated primary, secondary and tertiary fatty amines, quaternary ammonium salts, and mixtures thereof. Additionally, any amphoteric molecule that can be pH adjusted to become cationic may also be chosen.
  • Exemplary quaternary ammonium salts may be chosen from: -those of the general formula (I) below:
  • R1 , R2, R3, and R4, which may be identical or different, are chosen from linear and branched aliphatic radicals comprising from 1 to 30 carbon atoms, and aromatic radicals; and X- is chosen from halides, phosphates, acetates, lactates, (C2-C6) alkyl sulfates, and alkyl- or alkylaryl-sulfonates;
  • R9 is chosen from aliphatic radicals comprising from 16 to 30 carbon atoms
  • R10, R1 1 , R12, R13, and R14, which may be identical or different, are chosen from hydrogen and alkyl radicals comprising from 1 to 4 carbon atoms
  • X- is chosen from halides, acetates, phosphates, nitrates, ethyl sulfates, and methyl sulfates;
  • Exemplary and non-limiting quaternary ammonium salts of imidazoline may be chosen from those of formula (III) below: wherein R5 is chosen from alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms; R6 is chosen from hydrogen, C1 -C4 alkyl radicals, and alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms; R7 is chosen from C1 - C4 alkyl radicals; R8 is chosen from hydrogen and C1 -C4 alkyl radicals; and X- is chosen from halides, phosphates, acetates, lactates, alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates.
  • R5 is chosen from alkenyl and alkyl radicals comprising from 8 to 30 carbon atoms
  • R6 is chosen from hydrogen, C1 -C4 alkyl radicals, and alkenyl and alkyl radicals comprising
  • the at least one cationic surfactant may be chosen from behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, quaternium-83, quaternium-87, quaternium-22, behenylamidopropyl-2,3-di- hydroxypropyldimethylammonium chloride, palmitylamidopropyltrimethylammonium chloride, stearamidopropyldimethylamine, and chloride and methyl sulfates of diacyloxyethyldimethylammonium, of diacyloxyethylhydroxyethylmethylammonium, of monoacyloxyethyldihydroxyethylmethylammonium, of triacyloxyethylmethylammonium, of monoacyloxyethylhydroxyethyldimethylammonium, and mixtures thereof.
  • the at least one cationic surfactant may be chosen from caprylyl trimethyl ammonium chloride (Aliquat 2); oleyl trimethyl ammonium chloride (Aliquat 1 1 ); oleyl-linoleyl trimethyl ammonium chloride (Aliquat 15); dilauryl dimethyl ammonium chloride (Aliquat 204); lauryl heterocyclic tertiary amine (Amine C); cetyl dimethyl ethyl ammonium bromide (Ammonyx DME); cetyl dimethyl benzyl ammonium chloride (Ammonyx T); lauryl trimethyl ammonium chloride (Arquad 12-50); cetyl trimethyl ammonium chloride (Arquad 16-50); stearyl trimethyl ammonium chloride (Arquad 18-50); quaternized 2-amino pentadecane (Arquad L-15); dicoco dimethyl ammonium chloride
  • tetradecyl pyridinium bromide (Fixanol VR); heptadecenyl imidazolinium bromide (Intexan HB-50); quaternary substituted imidazoline of oleic acid (Monaquat OIBC); substituted imidazoline of myristic acid (Monazoline M); coco fatty dialkyi benzyl ammonium chloride (Quatrene CB); fatty glyoxalidinium chloride (Quatrene 0-56); soya fatty dialkyi benzyl ammonium chloride (Quatrene SFB); 1 -hydroxyethyl 2-heptadecenyl imidazoline hydrochloride (Romine BTQ); and lauryl dimethyl benzyl ammonium chloride (Vantoc CL).
  • Exemplary, non-limiting amphoteric surface active agents include derivatives of betaine, derivatives of alkylamphoacetates, derivatives of
  • Non-limiting examples of betaine derivatives which may be used include cocobetaine, such as, for example, DEHYTON AB-30® from Cognis, laurylbetaine, such as GENAGEN KB® from Clariant, oxyethylenated laurylbetaine (10 OE), such as LAURYLETHER(10 OE)BETAINE® from Shin Nihon Spain, oxyethylenated stearylbetaine (10 OE), such as STEARYLETHER(10 OE)BETAINE® from Shin Nihon Portugal, cocamidopropyl betaine, such as VELVETEX BK 35® from Cognis, and undecylenamidopropyl betaine, such as AMPHORAM U® from Ceca.
  • cocobetaine such as, for example, DEHYTON AB-30® from Cognis
  • laurylbetaine such as GENAGEN KB® from Clariant
  • oxyethylenated laurylbetaine (10 OE) such as LA
  • alkylamphoacetate derivatives include N-cocoyl-N-carboxymethoxyethyl-N-carboxymethyl-ethylenediamine N-di-sodium (INCI name: disodium cocamphodiacetate), such as MIRANOL C2M CONCENTRE NP® from Rhodia Chimie, and N-cocoyl-N-hydroxyethyl-N-carboxymethyl-ethylenediamine N- sodium (INCI name: sodium cocamphoacetate).
  • hydroxylsultaines that may be used include Cocamidopropyl hydroxysultaine, such as that sold as REWOTERIC AM® by Golschmidt-Degussa.
  • Exemplary, non-limiting anionic surface active agents include mixed esters of fatty acid or of fatty alcohol, of carboxylic acid and of glycerol; alkyl ether citrates; alkenyl succinates chosen from alkoxylated alkenyl succinates, alkoxylated glucose alkenyl succinates, and alkoxylated methylglucose alkenyl succinates; and phosphoric acid fatty esters.
  • the mixed esters of fatty acid or of fatty alcohol, of carboxylic acid and of glycerol which can be used as anionic surface-active agents may be chosen from, by way of non-limiting example, mixed esters of fatty acid or of fatty alcohol having an alkyl chain including from 8 to 22 carbon atoms and of a-hydroxy acid and/or of succinic acid with glycerol.
  • the a-hydroxy acid can be, for example, citric acid, lactic acid, glycolic acid, malic acid and their mixtures.
  • the alkyl chain of the fatty acids or alcohols from which the mixed esters which can be used can be chosen from those that are saturated or unsaturated and linear or branched. They may, by way of non-limiting example, be chosen from stearate, isostearate, linoleate, oleate, behenate, arachidonate, palmitate, myristate, laurate, caprate, isostearyl, stearyl, linoleyl, oleyl, behenyl, myristyl, lauryl and capryl chains.
  • the alkyl ether citrates which can be used as anionic surface-active agents can be chosen from, for example, the monoesters, diesters or triesters formed by citric acid and at least one oxyethylenated fatty alcohol, including a saturated or unsaturated and linear or branched alkyl chain having from 8 to 22 carbon atoms and including from 3 to 9 ethoxylated groups.
  • Nonlimiting examples of citrates may be chosen from the mono-, di- and triesters of citric acid and of ethoxylated lauryl alcohol, including from 3 to 9 ethoxylated groups, sold by Witco under the name Witconol EC, in particular Witconol EC 2129, which is predominantly a dilaureth-9 citrate, and Witconol EC 3129, which is predominantly a trilaureth-9 citrate.
  • the alkyl ether citrates that may be useful as anionic surface-active agents may, in various exemplary embodiments, be in the form neutralized to a pH of approximately 7, where the neutralizing agent may be chosen from, for example, inorganic bases, such as sodium hydroxide, potassium hydroxide, or ammonia, and organic bases such as mono-, di-, and triethanolamine, aminomethylpropane-1 ,3-diol, N-methyglucamine or basic amino acids, such as arginine and lysine, and their mixtures.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, or ammonia
  • organic bases such as mono-, di-, and triethanolamine, aminomethylpropane-1 ,3-diol, N-methyglucamine or basic amino acids, such as arginine and lysine, and their mixtures.
  • alkenyl succinates which can be used as anionic surface-active agents are chosen from, for example, ethoxylated and/or propoxylated derivatives, including those of the compounds of formulae (XIV) or (XV):
  • R and R' radicals are chosen from linear or branched alkyl radicals including from 6 to 22 carbon atoms (including, for example, 10, 12, 14, 16, 18, and 20)
  • - E is chosen from oxyethylene chains of formula (C2H4O)n, in which n ranges from 2 to 100 (for example 10, 20, 40, 60, 80 and 90), oxypropylene chains of formula (C3H6O)n ⁇ in which n' ranges from 2 to 100 (for example 5, 10, 20, 30, 40, 50, 60, 70, 80 and 90), random or blocked copolymers including 5
  • oxyethylene chains of formula (C2H40)n and oxypropylene chains of formula (C3H6O)n' such that the sum of n and n' ranges from 2 to 100 (for example 5, 10, 20, 30, 40, 50, 60, 70, 80 and 90), oxyethylenated and/or oxypropylenated glucose groups including, on average, from 4 to 100 oxyethylene and/or oxypropylene units distributed over all the hydroxyl functional groups, or oxyethylenated and/or oxypropylenated methylglucose groups including, on average, from 4 to 100 oxyethylene and/or oxypropylene units distributed over all the hydroxyl functional groups (for example 5, 10, 20, 30, 40, 50, 60, 70, 80 and 90).
  • n and n' are mean values and are therefore not necessarily integers.
  • n may range from 5 to 60, such as from 10 to 30.
  • the R and/or R' radical may be chosen from linear alkyl radicals including from 8 to 22, such as from 14 to 22, carbon atoms (for example 10, 12, 14, 16, 18 and 20 carbons). It may be, for example, the hexadecenyl radical, including 16 carbon atoms, or the octadecenyl radical, including 18 carbon atoms.
  • the acid functional group— COOH of the anionic surface-active agents of formulae (XIV) and (XV) may be neutralized by a neutralizing agent, the neutralizing agent being chosen from, for example, inorganic bases, such as sodium hydroxide, potassium hydroxide, or ammonia, and organic bases such as mono-, di-, and triethanolamine, aminomethylpropane-1 ,3-diol, N-methyglucamine or basic amino acids, such as arginine and lysine, and their mixtures.
  • a neutralizing agent being chosen from, for example, inorganic bases, such as sodium hydroxide, potassium hydroxide, or ammonia
  • organic bases such as mono-, di-, and triethanolamine, aminomethylpropane-1 ,3-diol, N-methyglucamine or basic amino acids, such as arginine and lysine, and their mixtures.
  • E oxyethylenated glucose including 10 oxyethylene groups
  • the phosphoric acid fatty esters and their oxyethylenated derivatives which can be used as anionic surface-active agents can further be chosen from esters formed of phosphoric acid and of at least one alcohol including a saturated or unsaturated and linear or branched alkyl chain having from 8 to 22 carbon atoms (for example 10, 12, 14, 16, 18 and 20) and esters formed of phosphoric acid and of at least one ethoxylated alcohol including a saturated or unsaturated and linear or branched alkyl chain having from 8 to 22 carbon atoms (for example 10, 12, 14, 16, 18 and 20) and including from 2 to 40 oxyethylene groups (for example 4, 6, 8, 10, 12, 14, 16, 18, 20 and 30), their salts and their mixtures.
  • esters may, for example, be chosen from esters of phosphoric acid and of C9-C15 alcohols or their salts, such as the potassium salt of C9- 15 alkyl phosphate sold under the name Arlatone MAP by ICI; esters of phosphoric acid and of stearyl and/or isostearyl alcohols, such as the phosphate of stearyl/isostearyl alcohols (INCI name: Octyldecyl phosphate) sold under the name Hostaphat CG120 by Hoechst Celanese; esters of phosphoric acid and of cetyl alcohol, and their salts, such as the potassium salt of C9- 15 alkyl phosphate sold under the name Arlatone MAP by ICI; esters of phosphoric acid and of stearyl and/or isostearyl alcohols, such as the phosphate of stearyl/isostearyl alcohols (INCI name: Octyldecyl phosphate) sold under the name Hostaphat
  • oxyethylenated derivatives such as the product sold under the name Crodafos CES (mixture of cetearyl alcohol, of dicetyl phosphate and of ceteth-10 phosphate) by Croda; or esters of phosphoric acid and of tridecyl alcohol, and their oxyethylenated
  • Trideceth-10 phosphate by Croda.
  • the oxyethylenated derivatives of phosphoric acid and of fatty alcohol can be prepared in accordance with the description given in WO-A- 96/14145, for example.
  • Additional non-limiting examples of anionic surface-active agents include alkaline salts of dicetyl and dimyristyl phosphate, alkaline salts of cholesterol sulfate, alkaline salts of cholesterol phosphate, lipoamino acids and their salts, such as mono- and disodium acylglutamates, for instance the disodium salt of N- stearoyl-L-glutamic acid sold under the name Acylglutamate HS21 by Ajinomoto, sodium salts of phosphatidic acid, phospholipids, alkylsulfonic derivatives, such as those of formula (XVI):
  • - R represents C16-C22 alkyl radicals, for example the C16H33 and C18H37 radicals taken as a mixture or separately, and
  • - M is an alkali metal or an alkaline earth metal, such as sodium.
  • mixtures of cationic surface-active agents may be used in certain exemplary embodiments.
  • mixtures of anionic surface-active agents may be used.
  • the continuous phase may optionally further comprise any additional component that may be desired in the final emulsion, depending on the ultimate intended application.
  • the continuous phase may optionally further comprise at least one humectant, sugar, polymer, peptide, UV absorber, sunscreen, dye, etc.
  • the continuous phase may optionally comprise at least one lipophilic active agent or compounds.
  • Non- limiting examples include retinol (vitamin A) and derivatives thereof, tocopherol (vitamin E) and derivatives thereof, essential oils or unsaponifiable materials (e.g., bergamot, tocotrienol, sesamine, gamma-oryzanol, phytosterols, squalenes, waxes and terpenes), ascorbyl palmitate, vitamin F glycerides, D vitamins, vitamin D2, vitamin D3, retinol, retinol esters, retinyl palmitate, retinyl propionate, carotenes including beta -carotene, D-panthenol, farnesol, farnesyl acetate, salicylic acid and compounds thereof, for instance 5-n-octanoylsalicylic acid, alkyl esters of alpha -hydroxy
  • a solution of particles can be separately prepared by any method known.
  • the solution may optionally be an aqueous solution, and may comprise particles that have a charge opposite to that of the charge on the coated oil droplet, or may comprise any silicate salt soluble in the solvent.
  • the solution comprises particles having a charge opposite to the charge of the coated oil droplet
  • the particles may have a contact angle of less than about 90°, such as less than about 75°, less than about 50°, or less than about 25°.
  • the particles may be present in the solution in a concentration ranging up to about 35 wt%, such as up to about 25 wt%, up to about 20 wt%, up to about 15 wt%, up to about 10 wt%, or up to about 5 wt%.
  • the particles may be present in a concentration ranging from about 0.10 wt% to about 30 wt%, about 0.25 wt% to about 25 wt%, about 0.50 wt% to about 20 wt%, or about 1 wt% to about 10 wt%.
  • the charge on the particle may be, for example, greater than about 15 mV, such as greater than about 20 mV, greater than about 25 mV, greater than about 30 mV, greater than about 35 mV, greater than about 40 mV, greater than about 45 mV, or greater than about 50 mV.
  • the particles may be chosen from particles of any shape, including, but not limited to, those that are substantially spherical, platelet-shaped, elongated, feather-shaped, and fiber-shaped, including mixtures thereof.
  • the average diameter of spherical particles may range, for example, up to about 20 ⁇ , such as up to about 10 ⁇ , up to about 5 ⁇ , up to about 2 ⁇ , or up to about 1 ⁇ .
  • the diameter of spherical particles may range from about 10 nm to about 10 ⁇ , such as about 25 nm to about 10 ⁇ , about 50 nm to about 10 ⁇ , about 100 nm to about 10 ⁇ , about 500 nm to about 10 ⁇ , about 1 ⁇ to about 10 ⁇ , about 10 nm to about 5 ⁇ , about 25 nm to about 5 ⁇ , about 50 nm to about 5 ⁇ , about 100 nm to about 5 ⁇ , about 500 nm to about 5 ⁇ , about 1 ⁇ to about 5 ⁇ , about 10 nm to about 20 ⁇ , about 25 nm to about 2 ⁇ , about 50 nm to about 2 ⁇ , about 100 nm to about 2 ⁇ , about 500 nm to about 10 ⁇
  • the particles that are platelet-shaped may have a width and/or length ranging, independently, up to about 1000 ⁇ , such as up to about 750 ⁇ , up to about 500 ⁇ , up to about 250 ⁇ , up to about 100 ⁇ , or up to about 50 ⁇ .
  • the width and/or diameter may range from about 1 ⁇ to about 750 ⁇ , such as about 1 ⁇ to about 500 ⁇ , or about 1 ⁇ to about 250 ⁇ .
  • the thickness of the platelet-shaped particles may range up to about 5 ⁇ , such as up to about 2 ⁇ , or up to about 1 ⁇ .
  • the thickness may range from about 100 nm to about 5 ⁇ , such as about 100 nm to about 2 ⁇ , or about 100 nm to about 1 ⁇ .
  • the particles that are fiber-shaped may have a length ranging up to about 100 ⁇ , such as up to about 50 ⁇ , up to about 25 ⁇ , or up to about 15 ⁇ .
  • the length may range from about 0.5 ⁇ to about 100 ⁇ , such as 0.5 ⁇ to about 50 ⁇ .
  • the diameter of the fiber-shaped particles may range up to about 750 nm, such as up to about 500 nm, up to about 250 nm, or up to about 100 nm.
  • the diameter may range from about 1 nm to about 750 nm, such as about 5 nm to about 500 nm, about 10 nm to about 250 nm, or about 25 nm to about 100 nm.
  • Particles useful according to various embodiments of the disclosure may be chosen from organic or inorganic particles, optionally surface-modified to provide electrostatic interaction with the surface-active agent.
  • particles may be chosen from nylon particles, PPMA particles, styrene particles, and silica particles.
  • oil droplet and particle sizes such that the oil droplet to average particle size ratio ranges from about 1 to about 25, such as about 5 to about 20, about 7.5 to about 15, or about 10.
  • the solution may be mixed with the O/W dispersion in a desired ratio.
  • solution:O/W dispersion may range from about 20:80 to about 80:20, such as about 40:60 to about 60:40, or about 50:50.
  • the silicate salt may be chosen from, for example, disodium silicate (Na 2 SO 3 ), calcium silicate, magnesium silicate, sodium silicate, aluminum silicate, potassium silicate, zirconium silicate, tetramethylammonium silicate, sodium alumino silicate, potassium methyl siliconate, sodium methyl siliconate, and mixtures thereof.
  • the silicate salt solution may comprise an amount of at least one silicate salt in an amount sufficient to prepare a solution having a concentration ranging from about 0.05 to about 0.3 M, such as about 0.08 to about 0.3 M, about 0.05 to about 0.2 M, or about 0.08 to about 0.2 M.
  • the pH may be adjusted so that silicic acid is produced.
  • the pH may be adjusted by any method known in order to achieve a final pH in the range of about 6.0 to about 10.0, such as about 6.5 to about 9.0, about 6.5 to about 8.5, or about 7.0 to about 8.0.
  • the solution may be mixed with the O/W dispersion in a desired ratio.
  • the ratio of silicate solution:O/W dispersion may range from about 20:80 to about 80:20, such as about 40:60 to about 60:40, or about 50:50.
  • FIG. 2 is a schematic of an exemplary method of encapsulating oil droplets according to an embodiment of the disclosure
  • 1(a) an oil dispersion in the form of micron-sized oil droplets is combined with an aqueous solution comprising at least one cationic surface active agent.
  • the at least one cationic surface active agent is adsorbed onto the oil droplet, rendering it positively charged.
  • a silicate salt solution comprising sodium meta-silicate is prepared, and in 11(b), the silicate salt solution is pH adjusted, after which, the oil-in- water dispersion and silicate salt solution are combined, resulting in an encapsulated oil droplet.
  • Methods for preparing encapsulated oil droplets, and emulsions comprising encapsulated oil droplets, according to embodiments of the disclosure may be useful for preparing O/W emulsions for use in a variety of industries, such as, by way of non-limiting example, food, personal care (e.g. cosmetic, dermatological, perfume, etc.), pharmaceutical, and consumer chemical (e.g. household products). It may also be possible to incorporate O/W emulsions prepared according to embodiments of the disclosure into compositions or emulsions (e.g. O/W, W/O, W/O/W, etc.) for use in a variety of industries, such as, by way of non-limiting example, food, personal care (e.g.
  • compositions, emulsions, and products comprising O/W emulsions according to embodiments of the disclosure, or comprising oil droplets encapsulated according to embodiments of the disclosure, are further intended to be within the scope of the disclosure.
  • compositions, emulsions, and products comprising oil droplets encapsulated according to various embodiments of the disclosure may be stable for a period of several months, such as up to about 24 months, up to about 18 months, up to about 12 months, or up to about 6 months, at room temperature. It should be noted, however, that stability may vary according to various embodiments of the disclosure, and/or compositions, emulsions, and/or products made according to embodiments described herein may not offer improved stability over an extended period of time, yet such embodiments are intended to be within the scope of the disclosure.
  • Example 1 Emulsion stabilization via silicilic acid complexation
  • An aqueous solution of cetyl trimethyl ammonium chloride surfactant was prepared having 4 times the CMC (4.0mM).
  • An oil phase (20% of the total composition) composed of 5% of isononyl isononanoate, 10% of sarcosine lauroyi isopropyl, and 5% isocetyl stearate was prepared and mixed with the aqueous solution to generate an O/W dispersion.
  • Example 2 Emulsion stabilization via particle absorption by electrostatic interaction
  • An aqueous solution of hydroxy trimethyl ammonium chloride surfactant was prepared having 3 times the CMC, at neutral pH. Next, a 5 wt% particle solution was prepared using silica particles. The pH of the solution was adjusted to greater than 7, using HCI 23 wt% and NaOH 1 M solutions.
  • the oil phase and particle solution were mixed 50:50 by volume to prepare an emulsion having tightly encapsulated oil droplets.
  • An exemplary schematic is seen in FIG. 4.

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Abstract

L'invention concerne des procédés de préparation d'émulsions huile dans l'eau stables par complexation d'acide silicique de gouttelettes d'huile de l'ordre du micron et/ou par adsorption de particules par interaction électrostatique, ainsi que des émulsions stables préparées selon lesdits procédés. L'invention concerne également des compositions et des produits comprenant lesdites dispersions.
PCT/IB2014/001487 2013-05-17 2014-05-16 Stabilisation d'émulsion WO2014184660A2 (fr)

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US13/896,663 US20140341954A1 (en) 2013-05-17 2013-05-17 Stable emulsions via particle absorption by electrostatic interaction
US13/896,646 2013-05-17
US13/896,663 2013-05-17
US13/896,646 US10028895B2 (en) 2013-05-17 2013-05-17 Emulsion stabilization via silicilic acid complexation

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9433578B2 (en) 2013-05-17 2016-09-06 L'oreal Stable bubbles via particle absorption by electrostatic interaction
US9452406B2 (en) 2013-05-17 2016-09-27 L'oreal Bubble encapsulation via silicilic acid complexation
US10028895B2 (en) 2013-05-17 2018-07-24 L'oreal Emulsion stabilization via silicilic acid complexation

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GB2131820A (en) 1982-12-13 1984-06-27 Chevron Res Nonionic emulsifier and hydrocarbyl substituted succinic anhydride compositions emulsified therewith
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US9433578B2 (en) 2013-05-17 2016-09-06 L'oreal Stable bubbles via particle absorption by electrostatic interaction
US9452406B2 (en) 2013-05-17 2016-09-27 L'oreal Bubble encapsulation via silicilic acid complexation
US10028895B2 (en) 2013-05-17 2018-07-24 L'oreal Emulsion stabilization via silicilic acid complexation

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