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Nanoemulsion Including Sucrose Fatty Acid Ester Nanoemulsionen Enthaltend Saccharosefettsäureester Nanoemulsions Comprenant Des Ester D’Acide Gras De Sucrose

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Nanoemulsion Including Sucrose Fatty Acid Ester Nanoemulsionen Enthaltend Saccharosefettsäureester Nanoemulsions Comprenant Des Ester D’Acide Gras De Sucrose (19) TZZ ¥__T (11) EP 2 563 164 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A23L 29/10 (2016.01) A23L 33/10 (2016.01) 29.06.2016 Bulletin 2016/26 A23L 33/15 (2016.01) A61K 9/107 (2006.01) (21) Application number: 11713391.8 (86) International application number: PCT/US2011/000538 (22) Date of filing: 22.03.2011 (87) International publication number: WO 2011/119228 (29.09.2011 Gazette 2011/39) (54) NANOEMULSION INCLUDING SUCROSE FATTY ACID ESTER NANOEMULSIONEN ENTHALTEND SACCHAROSEFETTSÄUREESTER NANOEMULSIONS COMPRENANT DES ESTER D’ACIDE GRAS DE SUCROSE (84) Designated Contracting States: (72) Inventor: BROMLEY, Philip, J. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Fullerton, CA 92832 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (74) Representative: Boult Wade Tennant Designated Extension States: Verulam Gardens BA ME 70 Gray’s Inn Road London WC1X 8BT (GB) (30) Priority: 23.03.2010 US 340944 P (56) References cited: (43) Date of publication of application: WO-A1-2008/039564 WO-A1-2009/029046 06.03.2013 Bulletin 2013/10 WO-A1-2010/008762 DE-A1-102008 015 366 US-A1- 2009 297 665 (73) Proprietor: VIRUN, INC. Walnut, CA 91789 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 563 164 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 563 164 B1 Description RELATED APPLICATIONS 5 [0001] Benefit of priority is claimed to U.S. Provisional Application Serial No. 61/340,944, filed March 23, 2010, entitled ""COMPOSITIONS CONTAINING NON-POLAR COMPOUNDS," to Philip Bromley. [0002] This application is related to U.S. Application No. 13/065,510, filed March 23, 2011, entitled "COMPOSITIONS CONTAINING NON-POLAR COMPOUNDS," which also claims priority to U.S. Provisional Application Serial No. 61/340,944. 10 [0003] This application is related to U.S. Application Serial No. 12/383,244, filed March 20, 2009, published as US- 2009-0297665-A1, and entitled "COMPOSITIONS CONTAINING NON-POLAR COMPOUNDS," and International Ap- plication No. PCT/US2009/001775, filed March 20,2009, published as International PCT Application No. WO 2009/117152 and entitled "EMULSIONS INCLUDING A PEG-DERIVATIVE OF TOCOPHEROL," all of which claim priority to U.S. Provisional Application Serial No. 61/070,381, filed March 20, 2008, entitled "COMPOSITIONS CON- 15 TAINING NON-POLAR COMPOUNDS" and U.S. Provisional Application Serial No. 61/132,424, filed June 16, 2008, entitled "COMPOSITIONS CONTAINING NON-POLAR COMPOUNDS," each to Philip Bromley. [0004] This application also is related to U.S. Patent Application No. 12/383,241, filed March 20, 2009, published as US-2009-0297491-A1 entitled "COMPOSITIONS CONTAINING NON-POLAR COMPOUNDS" and International Appli- cation No. PCT/US2009/001774, filed March 20, 2009, published as International PCT Application No. WO 2009/117151 20 and entitled "VITAMIN E DERIVATIVES AND THEIR USES," all of which claim priority to U.S. Provisional Application Serial No. 61/070,392, filed March 20,2008, entitled "COMPOSITIONS CONTAINING NON-POLAR COMPOUNDS" and U.S. Provisional Application Serial No. 61/132,409, filed June 16, 2008, entitled "COMPOSITIONS CONTAINING NON-POPLAR COMPOUNDS" each to Philip Bromley. 25 FIELD OF THE INVENTION [0005] Provided are compositions and methods for preparing foods and beverages that contain additives, such as nutraceuticals, pharmaceuticals and supplements. 30 BACKGROUND [0006] Non-polar compounds are not easily dissolved in aqueous solutions, such as water or other polar solvents. A number of non-polar compounds are used in compositions for human ingestion, for example, pharmaceuticals, nutraceu- ticals and/or dietary supplements. Exemplary non-polar compounds used in such compositions are vitamins and minerals, 35 fatty acids, and other non-polar compounds, non-polar active agents, and non-polar active ingredients. [0007] Because of poor water solubility, inclusion of non-polar compounds in products for human consumption, for example, supplements, foods and beverages, often is challenging. Available compositions containing non-polar com- pounds, particularly aqueous compositions containing non-polar compounds, and methods for formulating such com- positions, are limited. Thus, there remains a need to develop compositions containing non-polar compounds and methods 40 for making the compositions. Accordingly, it is among the objects herein to provide compositions, including aqueous compositions, containing non-polar compounds, and methods for making the compositions. [0008] DE 10 2008 015366 concerns a lyophilized nanoemulsion comprising a lipophilic phase and one or more sucrose fatty acid esters; to the nanoemulsion which can be prepared from the lyophilized nanoemulsion by redispersion, and to a process for the preparation of the lyophilized nanoemulsion. 45 [0009] WO 2008/039564 concerns a process allowing the solubilisation of flavor oil in water to produce clear beverages. [0010] WO 2010/008762 concerns compositions allowing the solubilisation of hydrophobic nutraceuticals in water to produce clear and stable solutions. SUMMARY 50 [0011] Provided are first compositions (concentrates) that contain non-polar compounds, including liquid nanoemulsion concentrates. Also provided are methods that use such first compositions to prepare other compositions, such as bev- erages and other aqueous liquids, into which the first compositions are diluted to form liquid dilution compositions. Also provided are liquid dilution compositions containing the beverage or other aqueous liquid and the diluted concentrate. 55 The concentrates contain dispersions, and/or can be used to prepare dispersions, of effective amounts of additives, such as non-polar compounds, including non-polar active ingredients, such as nutraceuticals, pharmaceuticals, and supplements, such as essential fatty acids, including polyunsaturated fatty acids, such as omega-3 fatty acids, omega- 6 fatty acids, conjugated fatty acids, and other fatty acids; phytochemicals, including phytosterols; other oils; coenzymes, 2 EP 2 563 164 B1 including Coenzyme Q10; vitamins, including vitamin D3; and other oil-based additives. The amounts in the resulting diluted compositions are effective to supplement the diet. The compositions provided herein are stable dispersions without phase separation or other changes. [0012] For example, the provided compositions include concentrates containing non-polar active ingredients, sur- 5 factants, and polar solvents, at amounts whereby dilution of the concentrate in an aqueous medium, such as a beverage, at a particular amount (e.g., any of the specified amounts, concentrations, and dilutions of the concentrates and any of the amounts of the non-polar active ingredients described herein below), yields a liquid dilution composition containing effective amounts of the non-polar active ingredient and having one or more desired properties. The provided compo- sitions further include liquid dilution compositions, including the liquid dilution compositions made from the concentrates, 10 containing aqueous media, non-polar active ingredients at effective amounts and polar solvents that have the desired properties. The amount of the concentrate and/or amount of the non-polar active ingredient can be specified. The desired properties include clarity of the liquid dilution compositions, such as compositions that are clear or about as clear as the aqueous medium in the absence of the concentrate and/or in the absence of the non-polar active ingredient; particle size, such as particle size of less than 200 nm or less than about 200 nm, less than 100 nm or less than about 100 nm, 15 less than 50 nm or less than about 50 nm, or less than 25 nm or less than about 25 nm, at most or on average; turbidity, such as a Nephelometric Turbidity Units (NTU) value of less than 200 or about 200, less than 100 or about 100, less than 50 or about 50, less than 30 or about 30, less than 25 or about 25, or less than 10 or about 10; and the lack of visible particles, visible crystals, phase separation, and/or ringing. [0013] The provided concentrates typically are liquid nanoemulsion concentrates, which contain surfactants (typically 20 a surfactant that is a sugar fatty acid ester or mixture of sugar fatty acids esters, such as, for example a sucrose fatty acid ester or a mixture of sucrose fatty acids esters or a mixture of the sucrose fatty acid esters and a PEG-derivative of Vitamin E), non-polar compound(s) (which typically is/are a non-polar active ingredient which differs from the surfactant) and a polar solvent (e.g., water or other edible aqueous liquid, such as a polar protic solvent such as a dihydric or trihydric alcohol, e.g., propylene glycol and glycerin (glycerol)). 25 [0014] The amount of non-polar compound in the concentrate typically is between 5 % or about 5 % and 10 % or about 10 %, by weight (w/w), of the concentrate, e.g., at or about 5, 5.2, 5.25, 6, 7, 8, 9, or 10 %, by weight, of the concentrate. [0015] The surfactants in the provided concentrates typically have a Hydrophilic Lipophilic Balance (HLB) value of between 14 or about 14 and 20 or about 20, such as between 15 or about 15 and 18 or about 18, e.g., at or about 15, 16, 17, or 18. Exemplary surfactants for use in the compositions provided include non-ionic surfactants, such as sugar 30 ester surfactants, such as sugar fatty acid ester surfactants, typically, sucrose fatty acid ester surfactants, which typically contain sucrose fatty acid monoesters (e.g., sucrose fatty acid ester surfactants).
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