# US 10,369,094 B2 · Hydrogel capsules and process for preparing the same

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- Number: US 10,369,094 B2
- Document ID: US10369094B2
- Status: Granted
- Kind: B2
- Application number: 15/722,022
- Filed: 2017-10-02
- Published: 2018-01-25
- Granted: 2019-08-06
- Earliest claimed: 2015-01-12
- Assignees: International Flavors & Fragrances Inc.
- Applicants: International Flavors & Fragrances Inc.
- Inventors: Yabin Lei; Li Xu
- Web page: https://patentgrep.com/patent/US10369094B2

## CPC

- A61K 8/8152: {Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers}
- A61K 8/068: {Microemulsions}
- A61K 8/11: Encapsulated compositions
- A61K 8/8147: {Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers}
- A61K 9/5026: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- A61Q 17/005: {Antimicrobial preparations}
- A61Q 19/10: Washing or bathing preparations
- C11D 3/50: Perfumes
- C11D 3/505: {encapsulated or adsorbed on a carrier, e.g. zeolite or clay}
- A61K 2800/412: Microsized, i.e. having sizes between 0.1 and 100 microns
- A61K 2800/5424: anionic
- A61K 2800/5426: cationic
- A61K 2800/56: Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
- A61K 2800/624: by macromolecular compounds
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

This invention is a hydrogel capsule with a fragrance encapsulated therein during the polymerization process. The hydrogel capsule is of use in fabric care or personal care formulations.

## Claims

### Claim 1

A hydrogel capsule comprising a fragrance encapsulated in at least one polymerized acrylic or methacrylic acid, or ester thereof, wherein
the hydrogel capsule has a mean diameter in the range of 1 to 100 μm;
the fragrance is encapsulated in the hydrogel capsule during polymerization of at least one acrylic or methacrylic acid, or ester thereof contained in an oil phase;
the oil phase contains: (i) the fragrance, (ii) the at least one acrylic or methacrylic acid, or ester thereof, and (iii) a water-insoluble oil solvent selected from the group consisting of an isoparaffinic fluid, a caprylic triglyceride, a capric triglyceride, a light mineral oil, a light mineral wax, a vegetable oil, a light vegetable wax, diethylphthalate, butylbenzoate, benzylbenzoate, an ester solvent, triacetin, a glycol-based water-insoluble solvent, and a combination thereof;
the at least one acrylic or methacrylic acid, or ester thereof is a multifunctional acrylate or methacrylate;
the multifunctional acrylate or methacrylate is further copolymerized with a monofunctional acrylate or methacrylate to form the shell of the hydrogel capsule; and
the ratio between the monofunctional acrylate or methacrylate and the multifunctional acrylate or methacrylate is up to 8:92 wherein the hydrogel capsule has a fragrance intensity greater than a hydrogel capsule prepared from a ratio greater than 8:92.

### Claim 2 (depends on 1)

The hydrogel capsule of claim 1, wherein the hydrogel capsule is coated with a deposition aid selected from the group consisting of: polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-24, polyquaternium-28, polyquaternium-37, polyquaternium-39, polyquaternium-44, polyquaternium-46, polyquaternium-47, polyquaternium-53, polyquaternium-55, polyquaternium-67, polyquaternium-68, polyquaternium-69, polyquaternium-73, polyquaternium-74, polyquaternium-77, polyquaternium-78, polyquaternium-79, polyquaternium-80, polyquaternium-81, polyquaternium-82, polyquaternium-86, polyquaternium-88, polyquaternium-101, polyvinylamine, polyethyleneimine, polyvinylamine and vinylformamide copolymer, an acrylamidopropyltrimonium chloride/acrylamide copolymer, a methacrylamidopropyltrimonium chloride/acrylamide copolymer, sodium alginate, chitosan, tannic acid, and combinations thereof.

### Claim 3 (depends on 1)

The hydrogel capsule of claim 1, wherein the hydrogel capsule has a mean diameter in the range of 1 to 20 μm; and the oil phase contains: (i) 50 to 90% of the fragrance, and (ii) 10 to 25% of the at least one acrylic or methacrylic acid, or ester thereof.

### Claim 4 (depends on 2)

The hydrogel capsule of claim 2, wherein the deposition aid is present at a level of 0.5% to 10% by weight of the hydrogel capsule.

### Claim 5 (depends on 1)

The hydrogel capsule of claim 1, wherein the multifunctional acrylate or methacrylate is ethylene glycol diacrylate, ethylene glycol dimethacrylate, poly(ethylene glycol) dimethacrylate, 1,6-hexandiol dimethacrylate, or a combination thereof.

### Claim 6 (depends on 5)

The hydrogel capsule of claim 5, wherein the multifunctional acrylate or methacrylate is ethylene glycol dimethacrylate.

### Claim 7 (depends on 1)

The hydrogel capsule of claim 1, wherein the monofunctional acrylate or methacrylate is methyl methacrylate.

### Claim 8 (depends on 1)

The hydrogel capsule of claim 1, wherein the hydrogel capsule further encapsulates an active material selected from the group consisting of a pro-fragrance, flavor, malodor counteractive agent, vitamin or derivative thereof, anti-inflammatory agent, fungicide, anesthetic, analgesic, antimicrobial active, anti-viral agent, anti-infectious agent, anti-acne agent, skin lightening agent, insect repellant, animal repellent, vermin repellent, emollient, skin moisturizing agent, wrinkle control agent, UV protection agent, fabric softener active, hard surface cleaning active, skin or hair conditioning agent, flame retardant, antistatic agent, nanometer to micron size inorganic solid, polymeric or elastomeric particle, taste modulator, cell, probiotic, or combination thereof.

### Claim 9 (depends on 1)

A hydrogel capsule of claim 1, further comprising a dispersant selected from the group consisting of a polyvinyl alcohol, polystyrene sulfonate, carboxymethyl cellulose, sodium polystyrene sulfonate, alkylnaphthalenesulfonate formaldehyde condensate, polyvinylpyrrolidone, copolymer of vinyl pyrrolidone and quaternized dimethylaminoethyl methacrylate, oleth-10-phosphate, cetyltrimethylammonium chloride, ammonium lauryl ether sulfate, cocoamidopropylamine oxide, nonylphenol ethoxylate, quillaja saponin, N-lauroyl-L-arginine ethyl ester, sorbitan esters, lecithins, lyso-lecithins, polyethoxylated sorbitan esters, polyglyceryl esters, fatty acid esters, gum arabic, pectin, carrageenan, chitosan, chondroitin sulfate, cellulose gum, modified starch, whey protein, pea protein, egg white protein, silk protein, gelatin of fish, proteins of porcine or bovine origin, ester gum, fatty acids, and combinations thereof.

### Claim 10 (depends on 1)

A delivery system comprising a hydrogel capsule of claim 1 in a slurry or solid form.

### Claim 11 (depends on 10)

The delivery system of claim 10, further comprising a rheology modifier selected from the group consisting of alkali-swellable anionic acrylic polymer emulsion, anionic hydrophobically modified alkali-soluble acrylic polymer emulsion, anionic acrylic copolymer emulsion, hydrophobically-modified ethoxylated urethane, xanthan gum, carrageenan, gellan, pectin, hydroxyethyl cellulose, sodium carboxymethyl cellulose, guar, sodium alginate, fully exfoliated smectite clays, and combinations thereof.

### Claim 12 (depends on 10)

The delivery system of claim 10, further comprising a second, third, fourth, fifth, or sixth capsule, wherein each of these capsules has a microcapsule core encapsulated by a microcapsule wall, and the microcapsule wall is independently formed of an encapsulating polymer selected from the group consisting of a sol-gel polymer, polyacrylate, polyacrylamide, poly(acrylate-co-acrylamide), polyurea, polyurethane, starch, gelatin and gum Arabic, poly(melamine-formaldehyde), poly(urea-formaldehyde), and combinations thereof.

### Claim 13 (depends on 1)

A consumer product comprising the hydrogel capsule of claim 1.

### Claim 14 (depends on 13)

The consumer product of claim 13, wherein said consumer product is a laundry care, personal care, therapeutic, cosmetic or cosmeceutic product.

### Claim 15 (depends on 14)

The consumer product of claim 14, wherein the personal care product is a hair shampoo, hair conditioner, leave-on hair products, hair rinse, antiperspirant deodorant, hand sanitizer, bar soap or body wash.

### Claim 16 (depends on 15)

The consumer product of claim 15, wherein antiperspirant deodorant product is formatted as a stick, roll-on or aerosol spray.

### Claim 17 (depends on 14)

The consumer product of claim 14, wherein the laundry care product is a rinse conditioner, liquid detergent, powder detergent or fabric refresher.

### Claim 18 (depends on 10)

A consumer product comprising the delivery system of claim 10.

### Claim 19 (depends on 18)

The consumer product of claim 18, wherein said consumer product is a laundry care, personal care, therapeutic, cosmetic or cosmeceutic product.