# US 8,540,908 B2 · Method of preparing nano-dispersed high-all-trans-carotenoid microcapsules

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- Number: US 8,540,908 B2
- Document ID: US8540908B2
- Status: Granted
- Kind: B2
- Application number: 13/259,291
- Filed: 2010-03-18
- Published: 2012-01-26
- Granted: 2013-09-24
- Earliest claimed: 2009-03-30
- Assignees: Zhejiang Nhu Company Ltd.; Zhejiang University; Beijing University of Chemical Technology
- Applicants: Zhirong Chen; Jianfeng Chen; Hong Yin; Hong Zhao; Dan Qiu; Lifang Shi; Jiandong Li; Guangwen Chu; Lei Shao
- Inventors: Zhirong Chen; Jianfeng Chen; Hong Yin; Hong Zhao; Dan Qiu; Lifang Shi; Jiandong Li; Guangwen Chu; Lei Shao
- Web page: https://patentgrep.com/patent/US8540908B2

## CPC

- B01J 13/043: {Drying and spraying}
- A23K 20/179: Colouring agents, e.g. pigmenting or dyeing agents
- A23L 5/44: using carotenoids or xanthophylls
- A23L 33/10: using additives (addition of substantially indigestible substances A23L33/21)
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A23P 10/30: Encapsulation of particles, e.g. foodstuff additives
- A61K 8/0241: {Containing particulates characterized by their shape and/or structure (see also A61K8/04, A61K8/11, and A61K8/14, further aspects are classified in A61K2800/40 and subcodes)}
- A61K 8/11: Encapsulated compositions
- A61K 8/31: Hydrocarbons
- A61K 8/35: Ketones, e.g. benzophenone
- A61K 31/01: Hydrocarbons
- A61K 31/122: having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
- A61Q 19/00: Preparations for care of the skin
- C09B 61/00: Dyes of natural origin prepared from natural sources {, e.g. vegetable sources}
- C09B 67/0097: {Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A61K 2800/412: Microsized, i.e. having sizes between 0.1 and 100 microns
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- A23K: FODDER
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23P: SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- 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
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

A method of preparing nano-dispersed high-all-trans-carotenoid microcapsules is provided, comprising: preparing 10-20% carotenoid suspension by milling the high-all trans-carotenoid crystals with dichloromethane until the particle size thereof is in the range of 2-5 μm, then supplying the suspension together with preheated dichloromethane of another pass into a dissolving tank to obtain a solution of 0.5-2%; delivering the solution together with ethanol or isopropanol into a crystallization device having high gravity rotating packed bed simultaneously and continuously, and then into a wiped-film evaporator for desolvation until the solid content is 10-20%, then a transparent alcohol dispersion of carotenoid is obtained; mashing the alcohol dispersion together with an aqueous solution containing an antioxidant and protective colloid and spray drying to obtain nano-dispersed high-all-trans-carotenoid microcapsules. As the crystals are nano-dispersed and the content of trans-isomer is more than 90%, the carotenoid microcapsules of present inventions exhibit high bioavailability.

## Claims

### Claim 1

A method of preparing nano-dispersed high-all-trans-carotenoid microcapsules, which comprises of the steps of:
1) milling crystallized carotenoid with more than 98% of all-trans and dichloromethane until particle size thereof is in the range of 2-5 μm, resulting in 10-20% carotenoid suspension;
2) continuously supplying the carotenoid suspension to a dissolving tank, while supplying dichloromethane after being preheated to 45-50° C. by a heat exchanger to the dissolving tank, maintaining the pressure at 0.2-0.3 MPa and the temperature at 35-40° C. in the dissolving tank, and with materials retention time of 4-12 minutes, to dissolve the crystallized carotenoid completely, resulting in dichloromethane solution with 0.5-2.0% of carotenoids;
3) continuously supplying dichloromethane solution with 0.5-2.0% of carotenoids to a crystallization device having a high gravity rotating packed bed and a liquid distributor; and also adding ethanol or isopropanol, with the weight of 5-10 times of dichloromethane solution, into the crystallization device; then precipitating carotenoid to be nano-crystal and obtaining a clear carotenoid dispersion;
4) continuously desolventizing the clear carotenoid dispersion under a reduced pressure in a wiped-film evaporator and obtaining alcohol dispersion with 10-20% of nano-dispersed carotenoid;
5) mixing the alcohol dispersion with nano-dispersed carotenoid and aqueous solution of antioxidant and protective colloid, and beating in another high gravity rotating packed bed; then spray drying the mixture to obtain nano-dispersed high-all-trans-carotenoid microcapsules.

### Claim 2 (depends on 1)

The method of claim 1, wherein the carotenoids refer to astaxanthin, canthaxanthin, β-carotene or lycopene.

### Claim 3 (depends on 1)

The method of claim 1, wherein the dissolving tank is a multi-layer agitator with the ratio of height to diameter of 3-4, and it is divided into 3-4 segments in each of which there is a stirrer; the materials are fed from a bottom of the tank and poured from a top of the tank.

### Claim 4 (depends on 1)

The method of claim 1, wherein the high gravity rotating packed bed has wire mesh packing and liquid distributor, and rotate speed is 1000-3000 rev/min.

### Claim 5 (depends on 1)

The method of claim 1, wherein the antioxidant is vitamin C, sodium L-ascorbate, isoascorbic acid or sodium D-isoascorbate.

### Claim 6 (depends on 1)

The method of claim 1, wherein the protective colloid is gelatin, fish gelatin or modified starch.