# US 9,872,832 B2 · Nanoemulsions having reversible continuous and dispersed phases

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- Number: US 9,872,832 B2
- Document ID: US9872832B2
- Status: Granted
- Kind: B2
- Application number: 14/921,572
- Filed: 2015-10-23
- Published: 2017-04-27
- Granted: 2018-01-23
- Earliest claimed: 2015-10-23
- Assignees: LG Bionano, LLC
- Applicants: LG Bionano, LLC
- Inventors: Chien-Chin Wu
- Web page: https://patentgrep.com/patent/US9872832B2

## CPC

- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A23D 7/0053: {Compositions other than spreads}
- A23L 27/80: {Emulsions}
- A61K 8/00: Cosmetics or similar toiletry preparations
- A61K 8/062: {Oil-in-water emulsions}
- A61K 8/064: {Water-in-oil emulsions, e.g. Water-in-silicone emulsions}
- A61K 8/068: {Microemulsions}
- A61K 8/345: {containing more than one hydroxy group}
- A61K 8/361: {Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof}
- A61K 8/375: {the alcohol moiety containing more than one hydroxy group}
- A61K 8/40: containing nitrogen (quinones containing nitrogen A61K8/355)
- A61K 8/46: containing sulfur (A61K8/44 takes precedence)
- A61K 8/60: Sugars; Derivatives thereof
- A61K 8/602: {Glycosides, e.g. rutin}
- A61K 8/891: saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K 8/922: {of vegetable origin}
- A61K 8/925: {of animal origin}
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/16: containing nitrogen, {e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates}
- A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K 47/20: containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- A61Q 19/00: Preparations for care of the skin
- C09D 11/02: Printing inks (C09D11/30 takes precedence)
- C09K 23/017: {Mixtures of compounds}
- C09K 23/54: Silicon compounds
- A61K 2800/21: Emulsions characterized by droplet sizes below 1 micron
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A23D: EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS (preservation thereof A23B20/00; production, refinement or preservation of animal or vegetable fats or oils C11B, C11C)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A nanoemulsion having reversible continuous and dispersed phases. The nanoemulsion includes an aqueous phase and an oil phase, a weight ratio of the aqueous phase to the oil phase being 1:40-100:1. In the nanoemulsion, the aqueous phase is dispersed as nanosized droplets in the oil phase or the oil phase is dispersed as nanosized droplets in the aqueous phase. The aqueous phase contains water or a water solution and a water-soluble organic nanostructure stabilizer. The oil phase contains an oil or an oil solution, an organic gel thickener, and a hydrophilic surfactant having a hydrophilic-lipophilic balance value greater than 8.0. Also disclosed is a method for preparing the above-described nanoemulsion.

## Claims

### Claim 1

A nanoemulsion comprising:
(A) an aqueous phase including:
(1) water or a water solution, and
(2) one or more water-soluble organic nanostructure stabilizers, in which the water or water solution has a content less than 75% by weight of the aqueous phase, each of the water-soluble organic nanostructure stabilizers has a content less than 99% by weight of the aqueous phase, and at least one of the water-soluble organic nanostructure stabilizers is urea, xylitol, or glucosamine, and
(B) an oil phase including:
(1) an oil or an oil solution,
(2) an organic gel thickener, and
(3) a hydrophilic surfactant having a hydrophilic-lipophilic balance value greater than 8.0,
in which the oil or oil solution has a content less than 80% by weight of the oil phase, the organic gel thickener has a content less than 60% by weight of the oil phase, and the hydrophilic surfactant has a content less than 60% by weight of the oil phase, wherein the water or water solution constitutes 2.5% by weight or more of the nanoemulsion, a weight ratio of the aqueous phase to the oil phase is 1:40-100:1, the aqueous phase is dispersed as nanosized droplets in the oil phase or the oil phase is dispersed as nanosized droplets in the aqueous phase, and the nanoemulsion is self-preserving, in the absence of an anti-microbial preservative, and has reversible continuous and dispersed phases.

### Claim 2 (depends on 1)

The nanoemulsion of claim 1, wherein the oil phase is dispersed as the nanosized droplets in the aqueous phase.

### Claim 3 (depends on 1)

The nanoemulsion of claim 1, wherein the aqueous phase is dispersed as the nanosized droplets in the oil phase.

### Claim 4 (depends on 2)

The nanoemulsion of claim 2, wherein the hydrophilic-lipophilic balance value is greater than 10.

### Claim 5 (depends on 4)

The nanoemulsion of claim 4, wherein the hydrophilic-lipophilic balance value is greater than 13.

### Claim 6 (depends on 3)

The nanoemulsion of claim 3, wherein the hydrophilic-lipophilic balance value is greater than 10.

### Claim 7 (depends on 6)

The nanoemulsion of claim 6, wherein the hydrophilic-lipophilic balance value is greater than 13.

### Claim 8 (depends on 4)

The nanoemulsion of claim 4, wherein the water-soluble organic nanostructure stabilizer is a water-soluble vitamin, a water-soluble peptide, a water-soluble oligopepetide, a polyol, a water-soluble saccharide, a water-soluble oligosaccharide, a disaccharide, a mono-saccharides, a hydrogenated carbohydrate, an amino acid, amino sugar, or a combination thereof; the oil is a vegetable oil, a silicone oil, a synthetic oil, a mineral oil, an animal oil, an essential oil, or a combination thereof; and the organic gel thickener is saturated fatty acid, fatty acid alcohol, a fatty acid derivative having a melting point above 45° C., or a combination thereof.

### Claim 9 (depends on 4)

The nanoemulsion of claim 4, wherein, also among the water-soluble organic nanostructure stabilizers, if any, is methylsulfonylmethane, hydroxyethyl urea, mannitol, sorbitol, lactose, fructose, dextrose, ribose, trehalose, raffinose, maltitol, isomalt, lactitol, erythritol, inositol, taurine, glycerin, propylene glycol, dipropylene glycol, butylene glycol, hexylene glycol, polyethylene glycol, ethoxydiglycol, carnitine, arginine, sodium pyrrolidone carboxylic acid, and hydrolyzed collagen, or a combination thereof; the oil is coconut oil, palm oil, grape seed oil, grape fruit seed oil, olive oil, avocado oil, evening primrose oil, tea tree oil, eucalyptus oil, lavender oil, rosemary oil, horse fat, fish oil, squalene, lanolin oil, squalene, cyclomethicone, cyclopentasiloxane, phenyl trimethicone, caprylic or capric triglyceride, isopropyl myristate, isostearyl isostearate, decyl oleate, ethylhexyl isononanoate, isohexadecane, octyldodecanol, paraffin oil, polyisobutene, polydecene, menthol, or a combination thereof; the organic gel thickener is stearic acid, lauric acid, glycerol monostearate, PEG 6000 Distearate, monoglyceride, diglyceride, saccharide fatty acid ester, propylene glycol fatty acid ester, glycol fatty acid ester, hexyl decyl fatty acid ester, fatty acid alcohol, cetyl stearate, ascorbyl fatty ester, glyceryl fatty ester, hexyldecyl fatty ester, or a combination thereof; and the hydrophilic surfactant is polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alcohol ester, nonyl phenol alkoxylate, alkyl alkoxylate, poly(ethylene glycol)-poly(propylene glycol)-poly(ethylene glycol) copolymer, PEG dimethicone, polyoxyethylene (40) fatty acid ester, polyoxyethylene (20) saccharide fatty acid ester, PEG-15 glyceryl fatty acid ester, PEG-35 hydrogenated castor oil, PEG-40 hydrogenated castor oil, polyglycerol fatty acid ester, fatty amine derivative, or a combination thereof.

### Claim 10 (depends on 9)

The nanoemulsion of claim 9, wherein the hydrophilic-lipophilic balance value is greater than 13; the water or water solution has a content less than 60% by weight of the aqueous phase and the water-soluble organic nanostructure stabilizer has a content less than 50% by weight of the aqueous phase; the oil or oil solution has a content less than 45-65% by weight of the oil phase, the organic gel thickener has a content less than 25% by weight of the oil phase, and the hydrophilic surfactant has a content less than 35% by weight of the oil phase; the water or water solution constitutes 30% by weight or less of the nanoemulsion and a weight ratio of the aqueous phase to the oil phase is 1:2-3:1; and the nanoemulsion has a pH of 3-11 and is transparent or translucent.

### Claim 11 (depends on 6)

The nanoemulsion of claim 6, wherein the water-soluble organic nanostructure stabilizer is a water-soluble vitamin, a water-soluble peptide, a water-soluble oligopepetide, a polyol, a water-soluble saccharide, a water-soluble oligosaccharide, a disaccharide, a mono-saccharides, a hydrogenated carbohydrate, an amino acid, amino sugar, or a combination thereof; the oil is a vegetable oil, a silicone oil, a synthetic oil, a mineral oil, an animal oil, an essential oil, or a combination thereof; and the organic gel thickener is saturated fatty acid, fatty acid alcohol, a fatty acid derivative having a melting point above 45° C., or a combination thereof.

### Claim 12 (depends on 6)

The nanoemulsion of claim 6, wherein, also among the water-soluble organic nanostructure stabilizers, if any, is methylsulfonylmethane, hydroxyethyl urea, mannitol, sorbitol, lactose, fructose, dextrose, ribose, trehalose, raffinose, maltitol, isomalt, lactitol, erythritol, inositol, taurine, glycerin, propylene glycol, dipropylene glycol, butylene glycol, hexylene glycol, polyethylene glycol, ethoxydiglycol, carnitine, arginine, sodium pyrrolidone carboxylic acid, and hydrolyzed collagen, or a combination thereof; the oil is coconut oil, palm oil, grape seed oil, grape fruit seed oil, olive oil, avocado oil, evening primrose oil, tea tree oil, eucalyptus oil, lavender oil, rosemary oil, horse fat, fish oil, squalene, lanolin oil, squalene, cyclomethicone, cyclopentasiloxane, phenyl trimethicone, caprylic or capric triglyceride, isopropyl myristate, isostearyl isostearate, decyl oleate, ethylhexyl isononanoate, isohexadecane, octyldodecanol, paraffin oil, polyisobutene, polydecene, menthol, or a combination thereof; the organic gel thickener is stearic acid, lauric acid, glycerol monostearate, PEG 6000 Distearate, monoglyceride, diglyceride, saccharide fatty acid ester, propylene glycol fatty acid ester, glycol fatty acid ester, hexyl decyl fatty acid ester, fatty acid alcohol, cetyl stearate, ascorbyl fatty ester, glyceryl fatty ester, hexyldecyl fatty ester, or a combination thereof; and the hydrophilic surfactant is polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alcohol ester, nonyl phenol alkoxylate, alkyl alkoxylate, poly(ethylene glycol)-poly(propylene glycol)-poly(ethylene glycol) copolymer, PEG dimethicone, polyoxyethylene (40) fatty acid ester, polyoxyethylene (20) saccharide fatty acid ester, PEG-15 glyceryl fatty acid ester, PEG-35 hydrogenated castor oil, PEG-40 hydrogenated castor oil, polyglycerol fatty acid ester, fatty amine derivative, or a combination thereof.

### Claim 13 (depends on 12)

The nanoemulsion of claim 12, wherein the hydrophilic-lipophilic balance value is greater than 13; the water or water solution has a content less than 60% by weight of the aqueous phase and the water-soluble organic nanostructure stabilizer has a content less than 50% by weight of the aqueous phase; the oil or oil solution has a content less than 45-65% by weight of the oil phase, the organic gel thickener has a content less than 25% by weight of the oil phase, and the hydrophilic surfactant has a content less than 35% by weight of the oil phase; the water or water solution constitutes 30% by weight or less of the nanoemulsion and a weight ratio of the aqueous phase to the oil phase is 1:2-3:1; and the nanoemulsion has a pH of 3-11 and is transparent or translucent.

### Claim 14 (depends on 8)

The nanoemulsion of claim 8, wherein the water or water solution has a content less than 60% by weight of the aqueous phase and the water-soluble organic nanostructure stabilizer has a content less than 70% by weight of the aqueous phase; the oil or oil solution has a content 30-70% by weight of the oil phase, the organic gel thickener has a content less than 45% by weight of the oil phase, and the hydrophilic surfactant has a content less than 45% by weight of the oil phase; and the water or water solution constitutes 38% by weight or less of the nanoemulsion and a weight ratio of the aqueous phase to the oil phase is 1:3-4:1.

### Claim 15 (depends on 14)

The nanoemulsion of claim 14, wherein the water or water solution has a content less than 45% by weight of the aqueous phase and the water-soluble organic nanostructure stabilizer has a content less than 50% by weight of the aqueous phase; the oil or oil solution has a content less than 45-65% by weight of the oil phase, the organic gel thickener has a content less than 25% by weight of the oil phase, and the hydrophilic surfactant has a content less than 35% by weight of the oil phase; and the water or water solution constitutes 30% by weight or less of the nanoemulsion and a weight ratio of the aqueous phase to the oil phase is 1:2-3:1.

### Claim 16 (depends on 11)

The nanoemulsion of claim 11, wherein the water or water solution has a content less than 60% by weight of the aqueous phase and the water-soluble organic nanostructure stabilizer has a content less than 70% by weight of the aqueous phase; the oil or oil solution has a content 30-70% by weight of the oil phase, the organic gel thickener has a content less than 45% by weight of the oil phase, and the hydrophilic surfactant has a content less than 45% by weight of the oil phase; and the water or water solution constitutes 38% by weight or less of the nanoemulsion and a weight ratio of the aqueous phase to the oil phase is 1:3-4:1.

### Claim 17 (depends on 16)

The nanoemulsion of claim 16, wherein the water or water solution has a content less than 45% by weight of the aqueous phase and the water-soluble organic nanostructure stabilizer has a content less than 50% by weight of the aqueous phase; the oil or oil solution has a content less than 45-65% by weight of the oil phase, the organic gel thickener has a content less than 25% by weight of the oil phase, and the hydrophilic surfactant has a content less than 35% by weight of the oil phase; and the water or water solution constitutes 30% by weight or less of the nanoemulsion and a weight ratio of the aqueous phase to the oil phase is 1:2-3:1.

### Claim 18 (depends on 15)

The nanoemulsion of claim 15, wherein the nanoemulsion has a pH of 3-11 and is transparent or translucent.

### Claim 19 (depends on 17)

The nanoemulsion of claim 17, wherein the nanoemulsion has a pH of 3-11 and is transparent or translucent.

### Claim 20 (depends on 1)

The nanoemulsion of claim 1, wherein the nanoemulsion has a pH of 3-11 and is transparent or translucent.

### Claim 21 (depends on 1)

The nanoemulsion of claim 1, wherein the nanoemulsion is a cosmetic product, a pharmaceutical product, a food product, a household chemical product, an agricultural product, a printing product, a dying product, a veterinary product, or a diagnostic product.

### Claim 22 (depends on 1)

A method for preparing the nanoemulsion of claim 1, the method comprising:
(1) mixing water or a water solution and one or more water-soluble organic nanostructure stabilizers to form an aqueous phase, in which the water or water solution has a content less than 75% by weight of the aqueous phase and each of the water-soluble organic nanostructure stabilizers has a content less than 99% by weight of the aqueous phase, and at least one of the water-soluble organic nanostructure stabilizers is urea, xylitol, or glucosamine;
(2) mixing an oil or an oil solution, an organic thickener, and a hydrophilic surfactants having a hydrophilic-lipophilic balance value greater than 8.0 to form an oil phase, in which the oil or oil solution has a content less than 80% by weight of the oil phase, the organic gel thickener has a content less than 60% by weight of the oil phase, and the hydrophilic surfactant has a content less than 60% by weight of the oil phase; and
(3) mixing the aqueous phase and the oil phase, a weight ratio of the aqueous phase to the oil phase being 1:40-100:1, to form a nanoemulsion, in which the water or water solution constitutes 74% by weight or less of the nanoemulsion;
whereby the aqueous phase is dispersed as nanosized droplets in the oil phase or the oil phase is dispersed as nanosized droplets in the aqueous phase.