# US 11,896,711 B2 · Process of making nanoemulsion

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- Number: US 11,896,711 B2
- Document ID: US11896711B2
- Status: Granted
- Kind: B2
- Application number: 17/187,973
- Filed: 2021-03-01
- Published: 2021-06-17
- Granted: 2024-02-13
- Earliest claimed: 2019-12-09
- Assignees: Nicoventures Trading Limited
- Applicants: Nicoventures Trading Limited
- Inventors: Anthony Richard Gerardi; Thomas H. Poole; Steven Lee Alderman
- Web page: https://patentgrep.com/patent/US11896711B2

## CPC

- A61K 9/0056: {Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals}
- A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol}
- A24B 13/00: Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff (reconstituted tobacco products A24B3/14)
- A24B 15/16: of tobacco substitutes
- A24B 15/303: {Plant extracts other than tobacco}
- A61K 9/006: {Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays}
- A61K 9/009: {Sachets, pouches characterised by the material or function of the envelope (with gastric retention A61K9/0065; sachets which are not administered but function merely as a container are classified according to the content, e.g. sachets comprising powder for reconstitution of a drink A61K9/0095)}
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 9/1617: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/1652: {Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin (homeopathic globules A61K9/1623)}
- A61K 9/1694: {resulting in granules or microspheres of the matrix type containing more than 5% of excipient}
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 47/02: Inorganic compounds
- 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 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/24: containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
- A61K 47/38: Cellulose; Derivatives thereof
- 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)
- 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)
- A24B: MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF

## Abstract

The disclosure provides a nanoemulsion including an oil phase containing at least one cannabinoid and a water phase; wherein at least one of the oil phase and the water phase includes one or more emulsifying agents; and wherein the zeta potential of the nanoemulsion is less than about −10 mV. Further provided are processes for preparing such nanoemulsions.

## Claims

### Claim 1

A process for preparing a nanoemulsion comprising at least one cannabinoid, the process comprising:
(a) providing an oil phase containing at least one cannabinoid;
(b) providing a water phase and combining the water phase with a polyoxyethylene stearic acid ester, lecithin, and glycerin, wherein the polyoxyethylene stearic acid ester and lecithin are present in an amount from about 10% to about 25% by weight, based on the total weight of the nanoemulsion;
(c) combining the oil phase and water phase to form a macroemulsion; and
(d) treating the macroemulsion to form the nanoemulsion.

### Claim 2 (depends on 1)

The process of claim 1, wherein (d) comprises sonicating the macroemulsion to form the nanoemulsion.

### Claim 3 (depends on 1)

The process of claim 1, wherein (d) comprises treating the macroemulsion in a homogenizer to form the nanoemulsion.

### Claim 4 (depends on 3)

The process of claim 3, wherein the homogenizer is a high pressure valve homogenizer, an ultrasonic jet homogenizer or an ultrasonic probe homogenizer.

### Claim 5 (depends on 3)

The process of claim 3, wherein the macroemulsion is passed through the homogenizer at a flow rate from about 100 mL/min to about 9 L/min.

### Claim 6 (depends on 3)

The process of claim 3, wherein the macroemulsion is passed through the homogenizer at a temperature from about 20° C. to about 40° C.

### Claim 7 (depends on 1)

The process of claim 1, wherein (d) comprises treating the macroemulsion in a microfluidizer to form the nanoemulsion.

### Claim 8 (depends on 1)

The process of claim 1, wherein the process further comprises (a)(1) heating the oil phase to a temperature of at least about 50° C. and dissolving the at least one cannabinoid therein.

### Claim 9 (depends on 8)

The process of claim 8, wherein (a)(1) comprises heating the oil phase to a temperature from about 60° C. to about 85° C.

### Claim 10 (depends on 1)

The process of claim 1, wherein a weight ratio of the oil to the at least one cannabinoid is from about 1:1 to about 10:1.

### Claim 11 (depends on 1)

The process of claim 1, wherein combining the water phase with the polyoxyethylene stearic acid ester, lecithin, and glycerin is performed via high shear mixing.

### Claim 12 (depends on 1)

The process of claim 1, wherein (c) comprises combining the oil phase and the water phase via high shear mixing to form the macroemulsion.

### Claim 13 (depends on 1)

The process of claim 1, wherein (c) comprises combining the oil phase and the water phase in a weight ratio from about 2:1 to about 1:10.

### Claim 14 (depends on 1)

The process of claim 1, wherein the at least one cannabinoid is selected from the group consisting of cannabigerol (CBG), cannabichromene (CBC), cannabidiol (CBD), tetrahydrocannabinol (THC), cannabinol (CBN) and cannabinodiol (CBDL), cannabicyclol (CBL), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), cannabinerolic acid, cannabidiolic acid (CBDA), Cannabinol propyl variant (CBNV), cannabitriol (CBO), tetrahydrocannabmolic acid (THCA), tetrahydrocannabivarinic acid (THCV A), and mixtures thereof.

### Claim 15 (depends on 1)

The process of claim 1, wherein the at least one cannabinoid comprises cannabidiol.

### Claim 16 (depends on 1)

The process of claim 1, wherein the oil phase comprises castor oil.

### Claim 17 (depends on 1)

The process of claim 1, wherein a zeta potential of the nanoemulsion is less than about −10 mV.

### Claim 18 (depends on 1)

The process of claim 1, wherein the nanoemulsion comprises droplets of the oil phase dispersed in the water phase, the droplets having an average diameter from about 1 nm to about 200 nm.