# US 10,117,832 B2 · Emulsified fatty acids

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- Number: US 10,117,832 B2
- Document ID: US10117832B2
- Status: Granted
- Kind: B2
- Application number: 15/847,736
- Filed: 2017-12-19
- Published: 2018-06-21
- Granted: 2018-11-06
- Earliest claimed: 2016-12-20
- Assignees: Barlean's Organic Oils, LLC
- Applicants: Barlean's Organic Oils, LLC
- Inventors: Peter Nguyen
- Web page: https://patentgrep.com/patent/US10117832B2

## CPC

- A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A23L 33/00: Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L 33/12: Fatty acids or derivatives thereof
- A23L 33/15: Vitamins
- A23L 35/10: {Emulsified foodstuffs}
- A61K 8/062: {Oil-in-water emulsions}
- A61K 8/36: Carboxylic acids; Salts or anhydrides thereof
- A61K 8/678: {Tocopherol, i.e. vitamin E}
- A61K 8/86: Polyethers
- A61K 9/0095: {Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches (A61K9/0007 takes precedence; eatable gels or foams A61K9/0056; oral mucosa adhesive forms A61K9/006)}
- A61K 31/201: having one or two double bonds, e.g. oleic, linoleic acids
- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- 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 47/46: Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 39/06: Free radical scavengers or antioxidants
- A61Q 19/00: Preparations for care of the skin
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

Provided herein are methods and processes for emulsifying non-polar compounds, such as omega fatty acids. Also provided are compositions that can be prepared according to the methods and processes described herein. The compositions, for example, have a high amount of the non-polar compound, such as a large amount of omega fatty acids. The non-polar compounds are also present in very small droplets within composition. For example, the mean or median particle size of the droplets is less than about 5 μm. Further, the composition includes a low amount of surfactant, such as less than about 10-15% of the surfactant.

## Claims

### Claim 1

A process for forming an oil-in-water emulsion, comprising combining under high-shear mixing:
a) an oil phase comprising:
i) d-α-tocopheryl polyethylene glycol succinate (“TPGS”) or one or more derivatives thereof, and
ii) one or more non-polar compounds; and
b) an aqueous phase comprising:
i) less than about 15% by weight of one or more emulsifiers, and
ii) the balance water and optionally one or more carriers;
wherein the emulsion comprises less than 2% by weight TPGS or derivatives thereof and about 20% to about 35% by weight of the one or more non-polar compounds and wherein the oil phase droplets have a median particle size greater than 1 μm but less than or equal to 3 μm.

### Claim 2 (depends on 1)

The process of claim 1, wherein the emulsion comprises less than 1% by weight TPGS or derivatives thereof.

### Claim 3 (depends on 1)

The process of claim 1, wherein the aqueous phase comprises less than about 5% by weight of the emulsifier.

### Claim 4 (depends on 1)

The process of claim 1, wherein the non-polar compound comprises an omega-3 fatty acid, omega-5 fatty acid, omega-6 fatty acid, omega-7 fatty acid, or mixture thereof.

### Claim 5 (depends on 1)

The process of claim 1, wherein the aqueous phase further comprises gum arabic, xanthan gum, guar gum, or a combination thereof.

### Claim 6 (depends on 1)

The process of claim 1, wherein the aqueous phase further comprises an organic acid.

### Claim 7 (depends on 6)

The process of claim 6, wherein the organic acid is citric acid, ascorbic acid, malic acid, or a combination thereof.

### Claim 8 (depends on 1)

The process of claim 1, wherein the aqueous phase further comprises from about 1% to about 20% by weight glycerin.

### Claim 9 (depends on 1)

The process of claim 1, wherein the aqueous phase further comprises xylitol, erythritol, or a combination thereof.

### Claim 10 (depends on 1)

The process of claim 1, wherein the oil phase further comprises from about 1% to about 5% by weight tocopherol, rosemary extract, or a combination thereof.

### Claim 11 (depends on 1)

The process claim 1, wherein the oil phase and the aqueous phase further comprise a preservative.

### Claim 12 (depends on 11)

The process of claim 11, wherein the oil phase preservative is sorbic acid.

### Claim 13 (depends on 11)

The process of claim 11, wherein the aqueous phase preservative is potassium sorbate, sodium benzoate, or combination thereof.

### Claim 14

A method for providing an emulsion, comprising:
providing a first mixture comprising d-α-tocopheryl polyethylene glycol succinate (“TPGS”) or derivative thereof and a non-polar compound or mixture of non-polar compounds, wherein the TPGS or derivative thereof is present in an amount less than 10% by weight of the first mixture and the non-polar compound or mixture of non-polar compounds are present in amount at least 90% by weight of the first mixture;
providing a second mixture, wherein the second mixture comprises water and one or more emulsifiers and wherein the one or more emulsifiers comprise less than about 15% of the second mixture;
combining the first mixture with the second mixture under high-shear to form an emulsion of the non-polar compound or mixture of non-polar compounds,
wherein the non-polar compounds or mixture thereof are present in the emulsion in droplets having a median particle size greater than 1 μm but less than or equal to about 3 μm, wherein the non-polar compounds or mixture thereof comprise about 20% to about 35% by weight of the emulsion, and wherein the TPGS or derivative thereof does not exceed 2% by weight of the emulsion.

### Claim 15 (depends on 14)

The method of claim 14, wherein the TPGS or derivative thereof does not exceed 1% by weight of the emulsion.

### Claim 16 (depends on 14)

The method of claim 14 wherein the non-polar compound or mixture thereof comprises an omega-3 fatty acid, an omega-5 fatty acid, an omega-6 fatty acid, an omega-7 fatty acid, or mixture thereof.

### Claim 17 (depends on 14)

The method of claim 14, wherein the emulsifier comprises gum arabic, xanthan gum, guar gum, or a combination thereof.

### Claim 18 (depends on 14)

The method of claim 14, wherein the emulsion comprises less than 5% of the emulsifier.

### Claim 19 (depends on 14)

The method of claim 14, wherein the non-polar compounds or mixture thereof are present in the emulsion in droplets having a median particle size of about 2 μm.

### Claim 20

An oil-in-water emulsion, comprising water and:
a) an emulsifier;
b) d-α-tocopheryl polyethylene glycol succinate (“TPGS”) or a derivative thereof; and
c) about 20% to about 35% by weight of one or more lipids;
wherein the emulsifier is present in an amount less than 10% by weight of the emulsion, wherein the TPGS is present in an amount less than 2% by weight of the emulsion, and wherein the lipids are present in the emulsion as droplets having a median particle size of greater than 1 μm but less than or equal to about 3 μm.

### Claim 21 (depends on 20)

The emulsion of claim 20, wherein the droplets have a median particle size of about 2 μm.

### Claim 22 (depends on 20)

The emulsion of claim 20, wherein the one or more lipids is an omega-3 fatty acid, omega-5 fatty acid, omega-6 fatty acid, omega-7 fatty acid, or mixture thereof.

### Claim 23 (depends on 20)

The emulsion of claim 20, wherein the emulsion comprises about 23% by weight of the one or more lipids.

### Claim 24 (depends on 20)

The emulsion of claim 20, wherein the TPGS comprises less than 1% of the emulsion.

### Claim 25 (depends on 20)

The emulsion of claim 20, wherein the TPGS comprises less than 0.5% of the emulsion.