WO2007014566A2 - Microcapsules and their use - Google Patents

Microcapsules and their use Download PDF

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Publication number
WO2007014566A2
WO2007014566A2 PCT/DK2006/000430 DK2006000430W WO2007014566A2 WO 2007014566 A2 WO2007014566 A2 WO 2007014566A2 DK 2006000430 W DK2006000430 W DK 2006000430W WO 2007014566 A2 WO2007014566 A2 WO 2007014566A2
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WO
WIPO (PCT)
Prior art keywords
particles
suspension
particle size
microcapsules
average particle
Prior art date
Application number
PCT/DK2006/000430
Other languages
French (fr)
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WO2007014566A3 (en
Inventor
Carsten Lynggaard Hansen
Original Assignee
Basf Aktiengesellschaft
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Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2007014566A2 publication Critical patent/WO2007014566A2/en
Publication of WO2007014566A3 publication Critical patent/WO2007014566A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules

Definitions

  • the present invention relates to a suspension or microcapsules comprising substantially crystalline particles of Coenzyme Q10 embedded in a matrix material, a process of preparing such a suspension or such microcapsules and products comprising the microcapsules or the suspension.
  • Coenzyme Q10 (or ubiquinone) is a well-known co-enzyme present in the cell mitochondria and important for metabolism. Q10 is widely present in food, such as meat, fish, legumes and cereals, but is often necessary as a dietary supplement.
  • raw Q10 is primarily crystalline at room temperature, the crystals are inhomogeneous in size and rather big (typically the crystal size is about 10- 50 ⁇ m when prepared synthetically or by microbiological procedures), and they are poorly soluble in water. Accordingly, only a small fraction of the raw Q10 will be taken up by the blood when administered to an elaborate.
  • JP S57-4916 relates to an oil-in-water emulsion of Q10 in a conventional macromolecular substance, wherein the Q10 is dissolved in oil before emulsifying.
  • the emulsion is spray dried to provide a powder having a relatively small particle size.
  • SE patent application No. 93/316 relates to a base formulation of Q10 comprising an amount of Q10 and further comprising a protective colloid forming material, such as starch, and being in the powder form with the coenzyme adsorbed by dry particle of the protective colloid forming material.
  • the base formulation is prepared by vacuum drying of a mixture of the colloid, Q10 and water, thus providing a powder.
  • WO 03/068008 relates to a powder composition which comprises droplets of Coenzyme Q10 dispersed in a matrix of a modified polysaccharide or a gelatine.
  • the droplets are prepared by melting and may have an average droplet diameter of 500 nm or less, and the powder composition is prepared by drying an emulsion containing the Q10 droplets in the matrix.
  • EP 498 824 relates to a process for preparing a hydrophobic/aerophilic solid, such as a carotenoid or a natural colorant, which solid is dispersable in water in the form of microparticles, the process comprising wetting of the solid in an aqueous medium by means of a hydrocolloid, milling the wetted solid to obtain a suspension containing suspended particles of an average particle size not exceeding 10 ⁇ m and finely dividing and drying the suspension to obtain a powder.
  • a hydrophobic/aerophilic solid such as a carotenoid or a natural colorant
  • the main object of the present invention is to provide compositions of Q10 in the form of a suspension or microcapsules, wherein the Q10 is dispersed or embedded as micro particles in a matrix material as well as a process of preparing them.
  • the microcapsules are suitable for dietary and food supplements, food, beverages, pharmaceutical and veterinary products, feed and feed supplements, personal care products and the like, due to a combination of improved bioavailability in comparison with compositions of Q10 in the raw form having rather coarse crystals, and improved stability in comparison with compositions, wherein Q10 is present as oil-in-water emulsions, in molten, super cooled or dissolved form.
  • the present invention relates accordingly to a novel suspension comprising substantially crystalline particles of Coenzyme Q10 dispersed in an aqueous solution of a matrix material, wherein said Q10 micro particles have an average particle size not exceeding 2 ⁇ m.
  • the invention further relates to a process of preparing a suspension comprising substantially crystalline particles of Coenzyme Q10 having an average particle size not exceeding 2 ⁇ m dispersed in an aqueous solution of a matrix material, which process comprises the steps of a) providing an aqueous solution of said matrix material, b) adding Q10 to said solution, c) treating the mixture thus obtained to prepare a suspension of Q10 in said aqueous solution comprising said matrix material, and d) finely dividing the suspension so as to obtain Q10 particles with an average particle size not exceeding 2 ⁇ m.
  • suspension as used herein means solid particles dispersed in an aqueous medium.
  • the invention also relates to a process for preparing microcapsules comprising substantially crystalline particles of Coenzyme Q10 having an average particle size not exceeding 2 ⁇ m embedded in a matrix material, which process comprises the steps of a) providing an aqueous solution of said matrix material, b) adding Q1 O to said solution, c) treating the mixture thus obtained to prepare a suspension of Q10 in said aqueous solution comprising said matrix material, d) finely dividing the suspension so as to obtain Q10 particles with an average particle size not exceeding 2 ⁇ m, and e) finely dividing and drying the suspension thus formed to obtain a mass of particles each containing a plurality of solid micro particles of Q10 embedded in said matrix material.
  • microcapsules as used herein means particles each comprising a matrix material having embedded therein a plurality of solid micro particles.
  • the invention relates in yet another aspect to the resulting microcapsules comprising substantially crystalline particles of Coenzyme Q10 embedded in a matrix material, wherein said Q10 particles have an average particle size not exceeding 2 ⁇ m.
  • the suspension and the microcapsules of the invention is advantageous due to an improved bioavailability of Q10 in comparison with raw Q10 material being relatively coarse.
  • the improved dividing of the particle to a micro size leads to a better absorption in the body.
  • the suspension and the microcapsules of the invention provide the possibility of preparing tablets having improved storage stability due to slower disintegration of the active substance, Q10, and the suspension and microcapsules of the invention exhibit an improved performance during preparation of tablets and improved stability.
  • Q10 in raw and pure crystalline form
  • Q10 having a heterogeneous particle size ranging up to typically 50 ⁇ m or more.
  • the improved dividing of the Q10 crystalline particles in the suspension of the invention will appear from the drawings in which
  • Figure 1 shows a SEM (Scanning Electron Microscopy) photo of Q10 in raw and pure crystalline form having a heterogeneous particle size and rather coarse particles.
  • Figure 2 shows a SEM (Scanning Electron Microscopy) photo of a Q10 suspension according to the invention comprising substantially crystalline Q10 particles.
  • the average particle size of the Q10 particle does not exceed 1 ⁇ m, e.g. the average size does not exceed 0.5 ⁇ m. In another embodiment the average particle size is substantially homogeneous and lies from 0.2-0.4 ⁇ m.
  • Matrix materials find wide spread use as materials for the microencapsulation of sensitive active substances in food, food supplements, pharmaceuticals and agricultural products.
  • the matrix material of the invention may be any conventional matrix material, such as naturally occurring and modified polysaccharides and naturally occurring hydrocolloids, e.g. alginate, carrageenan, gelatine, pectins and acacia gum.
  • Starch derived from a natural source, such as potato, wheat, maize, tapioca and rice, and modified starch are other examples of suitable matrix materials.
  • Modified starch prepared from the unmodified starch by (partial) degradation, depolymerisation, hydrolysis, etc is e.g. a matrix material.
  • a very appropriate modified starch to be used according to the invention is n-OSA modified starch, e.g. sodium octenyl succinate modified starch, i.e. a starch wherein a part of the hydroxyl groups are esterified by octenyl succinyl acid, providing a surface active property of the starch.
  • Another hydrocolloid is gelatine.
  • Step d) of the processes of the invention i.e. the fine dividing of the suspension so as to obtain the intended particle size, is e.g. carried out by milling and suitable in a bead mill or a similar mill having cooling equipment for maintaining the temperature sufficiently low in order not to melt or decompose the Q10 starting material and wherein the atmosphere can be controlled.
  • Step e) of the process of the invention may be carried out with conventional methods, such as spray cooling, spray drying, modified spray drying or sheet drying and crushing, see for example WO 91/06292.
  • the suspension and the microcapsules of the invention may include a small or a larger amount of Q10, e.g. from 5 to 95 %, on one embodiment a rather large amount.
  • the aqueous solution of the matrix material can optionally further contain excipients, such as dissolved carbohydrates, e.g. sorbitol and sucrose, and/or an antioxidant or an oil being or containing an antioxidant.
  • excipients such as dissolved carbohydrates, e.g. sorbitol and sucrose, and/or an antioxidant or an oil being or containing an antioxidant.
  • the products of the invention are suitable for a wide variety of applications, such as food, food supplements, beverages, pharmaceutical and veterinary products, feed, feed supplements, personal care products and households products. Accordingly the invention relates in yet another aspect to products comprising a suspension or microcapsules of the invention.
  • the process of the invention may be carried out in the accordance with the following general procedure: At all times during the preparation of the suspension, the vessel is covered with an inert gas, e.g. nitrogen, and the temperature kept well below the melting point of Q10, i.e. 5O 0 C.
  • an inert gas e.g. nitrogen
  • the suspension is sprayed as indicated above by spray cooling, spray drying or the like to provide microcapsules.
  • the particle size of the crystalline Q10 raw material was reduced to d(v,0.5) about 0.4 ⁇ m measured by light diffraction on a Malvern Mastersizer, while maintaining the temperature of the suspension below 10-12 0 C.
  • the resulting suspension has a substantially crystalline structure as shown in the SEM photo in Figure 2.
  • the resulting powder had a Q10 content of 6.3%.
  • the bioavailability of Q10 in the resulting microcapsules lay on the same level as the bioavailability of Q10 in compositions which comprise Q10 present as oil-in-water emulsions or in microcapsules made thereof.
  • microcapsules made from oil-in-water emulsions The chemical stability of the resulting microcapsules is improved in comparison with microcapsules made from oil-in-water emulsions.

Abstract

The invention relates to a suspension comprising substantially crystalline particles of Coenzyme Q10 dispersed in an aqueous solution of a matrix material, wherein said Q10 particles have an average particle size not exceeding 2 μm, microcapsules made thereof and a process of re arin said sus ension.

Description

Microcapsules and their use
FIELD OF THE INVENTION
The present invention relates to a suspension or microcapsules comprising substantially crystalline particles of Coenzyme Q10 embedded in a matrix material, a process of preparing such a suspension or such microcapsules and products comprising the microcapsules or the suspension.
BACKGROUND OF THE INVENTION
Coenzyme Q10 (or ubiquinone) is a well-known co-enzyme present in the cell mitochondria and important for metabolism. Q10 is widely present in food, such as meat, fish, legumes and cereals, but is often necessary as a dietary supplement.
It is also well known that the bioavailability of biologically active substances increases with decreasing particle size of the active substance. However, raw Q10 is primarily crystalline at room temperature, the crystals are inhomogeneous in size and rather big (typically the crystal size is about 10- 50 μm when prepared synthetically or by microbiological procedures), and they are poorly soluble in water. Accordingly, only a small fraction of the raw Q10 will be taken up by the blood when administered to an individuel.
It has been attempted to improve the bioavailability by using Q10 in compositions, wherein Q10 is present as oil-in-water emulsions, in molten, super cooled or dissolved form or in rather large crystals. In procedures for preparing such compositions, a relatively small particle size can be obtained, but the stability of the resulting compositions, compared to compositions comprising raw Q10, is reduced.
JP S57-4916 relates to an oil-in-water emulsion of Q10 in a conventional macromolecular substance, wherein the Q10 is dissolved in oil before emulsifying. The emulsion is spray dried to provide a powder having a relatively small particle size.
SE patent application No. 93/316 relates to a base formulation of Q10 comprising an amount of Q10 and further comprising a protective colloid forming material, such as starch, and being in the powder form with the coenzyme adsorbed by dry particle of the protective colloid forming material. The base formulation is prepared by vacuum drying of a mixture of the colloid, Q10 and water, thus providing a powder.
WO 03/068008 relates to a powder composition which comprises droplets of Coenzyme Q10 dispersed in a matrix of a modified polysaccharide or a gelatine. The droplets are prepared by melting and may have an average droplet diameter of 500 nm or less, and the powder composition is prepared by drying an emulsion containing the Q10 droplets in the matrix.
EP 498 824 relates to a process for preparing a hydrophobic/aerophilic solid, such as a carotenoid or a natural colorant, which solid is dispersable in water in the form of microparticles, the process comprising wetting of the solid in an aqueous medium by means of a hydrocolloid, milling the wetted solid to obtain a suspension containing suspended particles of an average particle size not exceeding 10 μm and finely dividing and drying the suspension to obtain a powder.
The main object of the present invention is to provide compositions of Q10 in the form of a suspension or microcapsules, wherein the Q10 is dispersed or embedded as micro particles in a matrix material as well as a process of preparing them. The microcapsules are suitable for dietary and food supplements, food, beverages, pharmaceutical and veterinary products, feed and feed supplements, personal care products and the like, due to a combination of improved bioavailability in comparison with compositions of Q10 in the raw form having rather coarse crystals, and improved stability in comparison with compositions, wherein Q10 is present as oil-in-water emulsions, in molten, super cooled or dissolved form.
SUMMARY OF THE INVENTION
The present invention relates accordingly to a novel suspension comprising substantially crystalline particles of Coenzyme Q10 dispersed in an aqueous solution of a matrix material, wherein said Q10 micro particles have an average particle size not exceeding 2 μm.
The invention further relates to a process of preparing a suspension comprising substantially crystalline particles of Coenzyme Q10 having an average particle size not exceeding 2 μm dispersed in an aqueous solution of a matrix material, which process comprises the steps of a) providing an aqueous solution of said matrix material, b) adding Q10 to said solution, c) treating the mixture thus obtained to prepare a suspension of Q10 in said aqueous solution comprising said matrix material, and d) finely dividing the suspension so as to obtain Q10 particles with an average particle size not exceeding 2 μm.
The term "suspension" as used herein means solid particles dispersed in an aqueous medium.
The invention also relates to a process for preparing microcapsules comprising substantially crystalline particles of Coenzyme Q10 having an average particle size not exceeding 2 μm embedded in a matrix material, which process comprises the steps of a) providing an aqueous solution of said matrix material, b) adding Q1 O to said solution, c) treating the mixture thus obtained to prepare a suspension of Q10 in said aqueous solution comprising said matrix material, d) finely dividing the suspension so as to obtain Q10 particles with an average particle size not exceeding 2 μm, and e) finely dividing and drying the suspension thus formed to obtain a mass of particles each containing a plurality of solid micro particles of Q10 embedded in said matrix material.
The term "microcapsules" as used herein means particles each comprising a matrix material having embedded therein a plurality of solid micro particles.
The invention relates in yet another aspect to the resulting microcapsules comprising substantially crystalline particles of Coenzyme Q10 embedded in a matrix material, wherein said Q10 particles have an average particle size not exceeding 2 μm.
The suspension and the microcapsules of the invention is advantageous due to an improved bioavailability of Q10 in comparison with raw Q10 material being relatively coarse. The improved dividing of the particle to a micro size leads to a better absorption in the body. Furthermore, the suspension and the microcapsules of the invention provide the possibility of preparing tablets having improved storage stability due to slower disintegration of the active substance, Q10, and the suspension and microcapsules of the invention exhibit an improved performance during preparation of tablets and improved stability.
As starting material for the preparation of the microcapsules of the invention is used Q10 in raw and pure crystalline form, which in the context is Q10 having a heterogeneous particle size ranging up to typically 50 μm or more. The improved dividing of the Q10 crystalline particles in the suspension of the invention will appear from the drawings in which
Figure 1 shows a SEM (Scanning Electron Microscopy) photo of Q10 in raw and pure crystalline form having a heterogeneous particle size and rather coarse particles.
Figure 2 shows a SEM (Scanning Electron Microscopy) photo of a Q10 suspension according to the invention comprising substantially crystalline Q10 particles.
DETAILED DESCRIPTION OF THE INVENTION
In one embodiment of the suspension and the microcapsules of the invention the average particle size of the Q10 particle does not exceed 1 μm, e.g. the average size does not exceed 0.5 μm. In another embodiment the average particle size is substantially homogeneous and lies from 0.2-0.4 μm.
Matrix materials find wide spread use as materials for the microencapsulation of sensitive active substances in food, food supplements, pharmaceuticals and agricultural products. The matrix material of the invention may be any conventional matrix material, such as naturally occurring and modified polysaccharides and naturally occurring hydrocolloids, e.g. alginate, carrageenan, gelatine, pectins and acacia gum. Starch derived from a natural source, such as potato, wheat, maize, tapioca and rice, and modified starch are other examples of suitable matrix materials.
Modified starch prepared from the unmodified starch by (partial) degradation, depolymerisation, hydrolysis, etc is e.g. a matrix material. A very appropriate modified starch to be used according to the invention is n-OSA modified starch, e.g. sodium octenyl succinate modified starch, i.e. a starch wherein a part of the hydroxyl groups are esterified by octenyl succinyl acid, providing a surface active property of the starch. Another hydrocolloid is gelatine.
Step d) of the processes of the invention, i.e. the fine dividing of the suspension so as to obtain the intended particle size, is e.g. carried out by milling and suitable in a bead mill or a similar mill having cooling equipment for maintaining the temperature sufficiently low in order not to melt or decompose the Q10 starting material and wherein the atmosphere can be controlled.
Step e) of the process of the invention may be carried out with conventional methods, such as spray cooling, spray drying, modified spray drying or sheet drying and crushing, see for example WO 91/06292.
The suspension and the microcapsules of the invention may include a small or a larger amount of Q10, e.g. from 5 to 95 %, on one embodiment a rather large amount.
The aqueous solution of the matrix material can optionally further contain excipients, such as dissolved carbohydrates, e.g. sorbitol and sucrose, and/or an antioxidant or an oil being or containing an antioxidant.
The products of the invention are suitable for a wide variety of applications, such as food, food supplements, beverages, pharmaceutical and veterinary products, feed, feed supplements, personal care products and households products. Accordingly the invention relates in yet another aspect to products comprising a suspension or microcapsules of the invention.
The process of the invention may be carried out in the accordance with the following general procedure: At all times during the preparation of the suspension, the vessel is covered with an inert gas, e.g. nitrogen, and the temperature kept well below the melting point of Q10, i.e. 5O0C.
Part of or all the water soluble ingredients are dissolved in cold water under agitation. When completely dissolved crystalline Q10 is added, also under agitation. This suspension is then milled in a ball mill in either one or several passages.
When the particle size of the crystalline Q10 is sufficiently low, the milling process is stopped and the optional remaining water soluble ingredients as well as the oil soluble ingredients are added, before the suspension is diluted to a spray-able viscosity.
The suspension is sprayed as indicated above by spray cooling, spray drying or the like to provide microcapsules.
The invention will now be described in further detail with reference to the following example.
EXAMPLE
Preparation of a microencapsulated Q10 powder.
Under inert gas, 100 g OSA-starch (Capsul® from National Starch), 4.7 g ascorbic acid and 5.3 g sodium ascorbate were dissolved in 490 g cold water. While agitating gently 100 g of crystalline Q10 raw material was added.
By passing the suspension through a ball mill the particle size of the crystalline Q10 raw material was reduced to d(v,0.5) about 0.4 μm measured by light diffraction on a Malvern Mastersizer, while maintaining the temperature of the suspension below 10-120C. The resulting suspension has a substantially crystalline structure as shown in the SEM photo in Figure 2.
After milling, additionally 345 g sucrose, 3.3 g dl-α-tocopherol and 83g water was added. The suspension was spray dried by modified spray drying into a cloud of suspended starch, forming a dry microencapsulated powder with a thin layer of starch coating.
During the whole process the temperature of the Q10 containing product was maintained well below the melting point of Q10 at 50 0C.
The resulting powder had a Q10 content of 6.3%.
The bioavailability of Q10 in the resulting microcapsules lay on the same level as the bioavailability of Q10 in compositions which comprise Q10 present as oil-in-water emulsions or in microcapsules made thereof.
The chemical stability of the resulting microcapsules is improved in comparison with microcapsules made from oil-in-water emulsions.

Claims

PATENT CLAIMS
1. A suspension comprising substantially crystalline particles of Coenzyme Q1O dispersed in an aqueous solution of a matrix material, wherein said Q10 particles have an average particle size not exceeding 2 μm.
2. A suspension according to claim 1 , wherein said Q10 particles have an average particle size not exceeding 1 μm.
3. A suspension according to any of the claims 1 or 2, wherein said Q10 particles have an average particle size not exceeding 0.5 μm.
4. A suspension according to any of the claims 1 to 3, wherein said Q10 particles have an average particle size of 0.2-0.4 μm.
5. A suspension according to any of the claims 1 to 4, wherein said Q10 particles size have been obtained by milling.
6. A suspension according to any of the claims 1 to 5, wherein said matrix material is selected from naturally occurring and modified polysaccharides and naturally occurring hydrocolloids, e.g. alginate, carrageenan, gelatine, pectins and acacia gum, starch derived from a natural source, such as potato, wheat, maize, tapioca and rice, and modified starch, such as sodium octenyl succinate modified starch.
7. A suspension according to any of the claims 1 to 6 further comprising an antioxidant.
8. A process of preparing a suspension comprising substantially crystalline particles of Coenzyme Q10 having an average particle size not exceeding 2 μm dispersed in an aqueous solution of a matrix material, which process comprises the steps of a) providing an aqueous solution of said matrix material, b) adding Q10 to said solution, c) treating the mixture thus obtained to prepare a suspension of Q 10 in said aqueous solution comprising said matrix material, and d) finely dividing the suspension so as to obtain Q 10 particles with an average particle size not exceeding 2 μm.
9. A process according to claim 8 for preparing microcapsules comprising substantially crystalline particles of Coenzyme Q10 having an average particle size not exceeding 2 μm embedded in a matrix material, which process further comprises the step of e) finely dividing and drying the suspension thus formed to obtain a mass of particles each containing a plurality of solid micro particles of Q10 embedded in said matrix material.
10. Process according to any of the claims 8 and 9, wherein step d) is carried out by milling.
11. Process according to claim 10, wherein the milling is carried out in a bead mill or a similar mill having cooling equipment and wherein the suspension can be kept under a controlled atmosphere.
12. Use of a suspension according to any of the claims 1 to 8 for preparing microcapsules.
13. Microcapsules comprising substantially crystalline particles of Coenzyme Q10 embedded in a matrix material, wherein said Q10 particles have an average particle size not exceeding 2 μm.
14. Microcapsules according to claim 13, wherein said Q10 particles have an average particle size not exceeding 1 μm.
15. Microcapsules according to any of the claims 12 to 14, wherein said Q10 particles have an average particle size not exceeding 0.5 μm.
16. Microcapsules according to any of the claims 12 to 15, wherein said Q10 particles have an average particle size of 0.2-0.4 μm.
17. Microcapsules according to any of the claims 12 to 16, wherein said Q10 particles size have been obtained by milling.
18. Microcapsules according to any of the claims 12 to 17, wherein said matrix material is selected from naturally occurring and modified polysaccharides and naturally occurring hydrocolloids, e.g. alginate, carrageenan, gelatine, pectins and acacia gum, starch derived from a natural source, such as potato, wheat, maize, tapioca and rice, and modified starch, such as sodium octenyl succinate modified starch.
19. Microcapsules according to any of the claims 12 to 18 further comprising an antioxidant.
20. A product comprising microcapsules according to any of the claims 13 to 19.
21. A product comprising a suspension according to any of the claims 1 to 7.
22. A product comprising a suspension obtainable according to claim 8 or microcapsules obtainable according to claim 9.
23. A product according to any of the claims 20 to 22 characterised in that it is a food, a food supplement, a beverage, a pharmaceutical or veterinary product, a feed or feed supplement, a personal care product or a household product.
PCT/DK2006/000430 2005-08-04 2006-08-04 Microcapsules and their use WO2007014566A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US70518405P 2005-08-04 2005-08-04
US60/705,184 2005-08-04
DKPA200501113 2005-08-04
DKPA200501113 2005-08-04

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008110626A1 (en) * 2007-03-15 2008-09-18 Dsm Ip Assets B.V. Stabilized micronised particles
EP2173321A2 (en) * 2007-07-19 2010-04-14 DSM IP Assets B.V. Tablettable formulations of lipophilic health ingredients
CN101658510B (en) * 2008-08-25 2011-08-10 沈阳皓天万嘉医药科技有限公司 Coenzyme Q10 self-emulsifying microcapsules and preparation method thereof
CN111632562A (en) * 2020-06-15 2020-09-08 上海应用技术大学 Starch-based supramolecular vesicle and preparation method thereof

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Publication number Priority date Publication date Assignee Title
WO1991006292A1 (en) * 1989-11-02 1991-05-16 Danochemo A/S Process of preparing a water dispersible hydrophobic or aerophilic solid
US20030105168A1 (en) * 2001-08-10 2003-06-05 Tsuyoshi Minemura Composition comprising ubiquinone
GB2402334A (en) * 2003-06-06 2004-12-08 Nbty Inc Coenzyme-Q10 containing pharmaceutical composition with improved bioavailability
US20050142123A1 (en) * 2002-02-14 2005-06-30 Chyi-Cheng Chen Water-dispersible coenzyme q10 dry powders

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991006292A1 (en) * 1989-11-02 1991-05-16 Danochemo A/S Process of preparing a water dispersible hydrophobic or aerophilic solid
US20030105168A1 (en) * 2001-08-10 2003-06-05 Tsuyoshi Minemura Composition comprising ubiquinone
US20050142123A1 (en) * 2002-02-14 2005-06-30 Chyi-Cheng Chen Water-dispersible coenzyme q10 dry powders
GB2402334A (en) * 2003-06-06 2004-12-08 Nbty Inc Coenzyme-Q10 containing pharmaceutical composition with improved bioavailability

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008110626A1 (en) * 2007-03-15 2008-09-18 Dsm Ip Assets B.V. Stabilized micronised particles
EA015698B1 (en) * 2007-03-15 2011-10-31 ДСМ АйПи АССЕТС Б.В. Stabilized micronised particles
EA022628B1 (en) * 2007-03-15 2016-02-29 ДСМ АйПи АССЕТС Б.В. Method for preparing suspension of natamycin particles
EP2173321A2 (en) * 2007-07-19 2010-04-14 DSM IP Assets B.V. Tablettable formulations of lipophilic health ingredients
CN101658510B (en) * 2008-08-25 2011-08-10 沈阳皓天万嘉医药科技有限公司 Coenzyme Q10 self-emulsifying microcapsules and preparation method thereof
CN111632562A (en) * 2020-06-15 2020-09-08 上海应用技术大学 Starch-based supramolecular vesicle and preparation method thereof

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