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(12) United States Patent (10) Patent No.: US 9,585,837 B2 Mai Et Al

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(12) United States Patent (10) Patent No.: US 9,585,837 B2 Mai Et Al USOO9585837B2 (12) United States Patent (10) Patent No.: US 9,585,837 B2 Mai et al. (45) Date of Patent: Mar. 7, 2017 (54) THERMALLY STABLE OIL-IN-WATER (52) U.S. Cl. EMULSIONS CONTAINING AN OIL THAT CPC ............ A61K 9/107 (2013.01); A61K 9/0095 CONTAINS POLYUNSATURATED FATTY (2013.01); A61K 9/19 (2013.01); A61K 3L/20 ACDS (2013.01) (58) Field of Classification Search (75) Inventors: Jimbin Mai, Columbia, MD (US); CPC ................................ A61K 9/107; A61K 31/20 Micah Hazzy Needham, Winchester, See application file for complete search history. KY (US); Gang Su, Ellicott City, MD (56) References Cited (US); Wei Wang-Nolan, Ellicott City, MD (US); Chia-Ping Charles Hsu, U.S. PATENT DOCUMENTS Ellicott City, MD (US) 4,199,604. A 4, 1980 Kahn et al. 5,156,652 A 10/1992 Gregoli et al. (73) Assignee: DSM IPASSETS B.V., Heerlen (NL) 6,426,078 B1* 7/2002 Bauer et al. .................. 424/401 6,596,336 B1* 7/2003 Gimelli et al. ............... 426,589 (*) Notice: Subject to any disclaimer, the term of this 2006, OO52446 A1 3/2006 Chilton et al. patent is extended or adjusted under 35 2008/0058418 A1* 3/2008 D’Angelo et al. ............ 514,560 U.S.C. 154(b) by 481 days. 2008/0254193 A1* 10, 2008 Edelman et al. ............. 426,602 (21) Appl. No.: 13/640,106 FOREIGN PATENT DOCUMENTS WO WOO224152 A2 * 3, 2002 (22) PCT Filed: Apr. 6, 2011 (86). PCT No.: PCT/US2O11AO31410 OTHER PUBLICATIONS S 371 (c)(1), Binks et al. Effects of pH and Salt Concentration on Oil-in-Water (2), (4) Date: Dec. 22, 2012 Emulsions Stabilized Solely by Nanocomposite Microgel Particles. Langmuir (2006), vol. 22, pp. 2050-2057.* (87) PCT Pub. No.: WO2011/127163 International Search Report for PCT/US2011/031410, mailed Jun. 16, 2011. PCT Pub. Date: Oct. 13, 2011 * cited by examiner (65) Prior Publication Data Primary Examiner — Wu-Cheng Winston Shen US 2013/0210916 A1 Aug. 15, 2013 Assistant Examiner — Taina D Matos Negron (74) Attorney, Agent, or Firm — Nixon & Vanderhye P.C. Related U.S. Application Data (57) ABSTRACT The present invention relates to thermally, stable oil-in (60) Provisional application No. 61/322,747, filed on Apr. water emulsions comprising an oil comprising a polyunsatu 9, 2010, provisional application No. 61/350,410, filed rated fatty acid, water, an emulsifier, and a water-soluble on Jun. 1, 2010. stabilizer, and processes for preparing the thermally stable (51) Int. Cl. oil-in-water emulsions. The thermally stable oil-in-water A 6LX 9/07 (2006.01) emulsions remain flowable at a temperature of -40°C., and A6 IK 3L/20 (2006.01) are free from a variation in particle size after 9 months in A6 IK 9/00 (2006.01) storage at a temperature of -40°C. to -15° C. A 6LX 9/19 (2006.01) 19 Claims, 2 Drawing Sheets U.S. Patent Mar. 7, 2017 Sheet 1 of 2 US 9,585,837 B2 begin?, .. 8. 8xxx k. ; : i ww2 yee x· S : Cic . ... 0.2.0.4.o.o.o. 0.6-or-0.3- or rel Particle size um) Figure 1 U.S. Patent Mar. 7, 2017 Sheet 2 of 2 US 9,585,837 B2 Processing Flow Diagram of Freezable Emulsion ranaanam-m-m-m-m-m-m-m-raaaaaaaaaaaaaaaaaaaaaaaaaarurukurukunusuaua urrrrrrrrrrrrrrr---------- Add water soluble dry -- ingredicints (trisodiull citratic ... !. anhydrous, sodiull Motified feed sii -- . -- hexanctaphosphatic, potassiul Il IIlodified EL: I. Eicacia (83.ë. & ur ---------------- f sorbatc. 703. citric acid) Si3 wiy ink it w8ter Sol.ital ingredisfits 3r. staf chi3A &otif. is fixing artill fixtuira is fires of fully hydratex : Siarcist Sikydiastics: is water Fregar: water seiabic ciry ingredicats (3.3% citric acid full arthydrolas, sediuri was clubs is Sexiesis 3:2yriate &-oil prastic fyiix it. ixepterisis. Nattikril 3&ix --- is&xse essassic-Eg'egia Eatics & rese; rary extract ixite EtiA kiki glyce; i.e. R. S. s: Ensig1 anxiiigi sh:3: l'Eixing ------------s-s-s-s-s-ma-a-a- costingCasing Stirlsistateemisents routedrealiticist engaue Ritiis. ric o - - - co-tour is cagigg Psi age ci:isioi i Esiliili hittie. Figure 2 US 9,585,837 B2 1. 2 THERMALLY STABLE OL-IN-WATER glycol and a monosaccharide, and glycerol. When the water EMULSIONS CONTAINING AN OL THAT soluble stabilizer is selected from a mixture of sodium CONTAINS POLYUNSATURATED FATTY chloride and a monosaccharide, or a mixture of propylene ACDS glycol and a monosaccharide, then the stabilizer can be present in a concentration of about 20% to about 50% by This application is the U.S. national phase of International weight of the emulsion. When the water soluble stabilizer is Application No. PCT/US2011/031410 filed 6 Apr. 2011 glycerol, then the water-soluble stabilizer can be present in which designated the U.S. and claims priority to U.S. a concentration of about 20% to about 55% by weight of the Provisional Application No. 61/322,747 filed 9 Apr. 2010 emulsion. In some embodiments, the thermally stable oil and 61/350,410 filed 1 Jun. 2010, the entire contents of each 10 in-water emulsion remains at least partially liquefied at a of which are hereby incorporated by reference. temperature of about -80° C., and, in some embodiments, -40°C., and preferably is free from a variation in particle BACKGROUND OF THE INVENTION size and organoleptic properties after 9 months in storage at a temperature of about -40°C. to about -15° C., or, at a Field of the Invention 15 temperature of about -40° C. to about 0° C., or, at a The present invention is directed to freezable oil-in-water temperature of about -80° C. to about 0° C., or at a emulsions comprising an oil comprising one or more poly temperature of about -80° C. to about -40°C. unsaturated fatty acids, and processes for preparing the In some embodiments, the emulsion has a minimum 12 freezable oil-in-water emulsions. month shelf life at freezing temperatures, i.e., temperatures Background at or below 0°C., preferably between -80° C. to 0°C., and Polyunsaturated fatty acids (“PUFAs, including long even more preferably between about -40°C. to about -15° chain PUFAs “LC-PUFAs) have been shown to enhance C., or, -40°C. to 0°C., or at a temperature of about -80° cognitive function and maintain cardiovascular health, C. to about -40° C. among other benefits. In particular, omega-3 PUFAs are In some embodiments, the thermally stable oil-in-water important dietary components for preventing arteriosclerosis 25 emulsion is free from a variation in particle size and orga and coronary heart disease, for alleviating inflammatory noleptic properties after 10 freeze-thaw cycles. conditions, and for retarding the growth of tumor cells, and In some embodiments, the emulsion has a minimum 9 or omega-6 PUFAs are important as both structural lipids, and 12 month shelf life at freezing temperatures, i.e., tempera as precursors for, e.g., prostaglandins and leukotrienes. tures at or below 0° C. and also is free from a variation in PUFAs are an important element of a healthy diet, but 30 particle size and organoleptic properties after 10 freeze-thaw because PUFAs are not synthesized by humans in vivo, these cycles. For example, in Some embodiments, the emulsions compounds must be ingested. For example, the oils of many of the invention are free from a variation in particle size and plants and animals (e.g., fish, walnuts, lingonberries, hemp, undesired organoleptic properties when stored at tempera algae and the seeds and/or leaves of several plants such as tures between -40°C. to 0°C., or, at a temperature of about flax, chia, perilla and purslane) are rich in PUFAs. Many 35 -40°C. to about -15°C., or, and preferably when stored at people also choose to ingest PUFAs through dietary Supple temperatures between -80° C. to 0°C., or at a temperature ments and/or PUFA-enhanced food products. As a result, of about -80° C. to about -40° C. consumer demand for products that containing PUFAS has In some embodiments, Sodium chloride is present in a recently increased, and a wide range of products now concentration of about 10% to about 25% by weight of the contain PUFAs. 40 emulsion and a monosaccharide is present in a concentration Oil-in-water emulsions have been used as a vehicle for of about 3% to about 15% by weight of an emulsion. In some PUFAs, both as a precursor for preparing comestibles, and embodiments, propylene glycol is present in a concentration in particular, as a component in formulated beverages, of about 10% to about 30% by weight of the emulsion, and foods, nutraceuticals, and pharmaceuticals. However, a monosaccharide is present in a concentration of about 10% PUFAs present in an emulsion can become unstable and 45 to about 30% by weight of the emulsion. In some embodi degrade (e.g., via Oxidation and/or photolytic degradation), ments, glycerol is present in a concentration of about 25% and therefore, maintaining the physical and chemical stabil to about 55% by weight of the emulsion, for example, about ity of PUFAs in an emulsion is critical. Freezing a PUFA 46%, about 47%, about 48%, about 49%, about 50%, about containing oil-in-water emulsion is an attractive means for 51%, etc. reducing the oxidative potential of PUFAs during shipment 50 In some embodiments, a PUFA is selected from: O-lino and/or storage. Unfortunately, freezing can lead to de lenic acid, Y-linolenic acid, linoleic acid, conjugated linoleic emulsification, and require extended periods of time for acid, arachidonic acid, c)-3 docosapentaenoic acid, (D-6 thawing prior to use.
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