Fragrance nanoemulsions and methods of making same

Abstract

Provided herein is a perfume nanoemulsion. The nanoemulsion contains a plurality of oil droplets, an aqueous phase, and a surfactant system comprising a polyethoxylated sorbitan fatty acid ester and lecithin. Also disclosed are liquid beverages or liquid beverage concentrates containing the nanoemulsions and methods of making the same.

Description

[0001] This application is a divisional application of the Chinese invention application with an international application date of October 20, 2015, an international application number of PCT / US2015 / 056470, an application number of 201580056758.X entering the Chinese national phase, and an invention name of “Fragrance nanoemulsion and method for preparing the same”.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims the benefit of priority from two U.S. applications: (i) Serial No. 62 / 065,865, filed October 20, 2014, and Serial No. 62 / 197,919, filed July 28, 2015. The contents of both applications are incorporated by reference in their entirety. Technical Field

[0004] The present invention relates to a fragrance nanoemulsion and a method for preparing the same. Background Art

[0005] Flavor nanoemulsions have been used to produce optically clear beverages containing hydrophobic flavor oils. Surfactants are added to facilitate the formation of nanoemulsions and also to stabilize these nanoemulsions.

[0006] U.S. Patent Application Publication No. 2009 / 0285952 discloses a nanoemulsion composition containing enzymatically degradable lecithin for use in alcoholic or carbonated beverages. Japanese Application No. 2003 / 284510 describes an alcohol-resistant composition in which polyglycerol fatty acid esters and sucrose fatty acid esters are used as surfactants. However, due to the surfactants contained therein, it is believed that this composition is not satisfactory in terms of flavor. See US2009 / 0285952. Japanese Patent No. 05588048 discloses a flavor emulsion composition that can be used in alcoholic beverages and contains hydrophilic polyglycerol fatty acid esters, lipophilic polyglycerol fatty esters, and lysolecithin. A high concentration of polyglycerol esters is used in the composition. US2009 / 0196972 describes a flavor composition having a high level (e.g., at least 20%) of polysorbate as a surfactant. US2013 / 0064954 discloses a flavor nanoemulsion composition for food applications (e.g., sauces) having a high level of polysorbate. However, these known emulsion compositions are not ideal for preparing optically clear, stable alcoholic beverages.

[0007] There is a need to develop a flavor nanoemulsion with high stability for preparing optically clear, stable alcoholic beverages with enhanced flavor. Summary of the Invention

[0008] The present invention is based on the discovery that flavor nanoemulsions prepared from polyethoxylated sorbitan fatty acid esters and lecithin are stable and optically clear in liquid beverages, including alcoholic beverages.

[0009] Thus, one aspect of the present invention relates to a fragrance nanoemulsion comprising a plurality of oil droplets, an aqueous phase, and a surfactant system.

[0010] In some embodiments, the nanoemulsion has a water activity of 0.7 or less (e.g., 0.65 or less and 0.6 or less) and has a water content of 25% or less (e.g., 20% or less and 15% or less) based on the weight of the nanoemulsion.

[0011] Each of the oil droplets having a droplet size of 0.1 to 500 nm contains a flavoring and is dispersed in the aqueous phase. In addition, the oil droplets may each contain an oil-soluble vitamin, an oil-soluble colorant, an antioxidant, a flavor modifier, a mouthfeel modifier, or a combination thereof. Exemplary flavor modifiers are acid masking agents, cooling agents, hot tasting substances, sweeteners, salting agents, substances that induce salivation, substances that cause a warming or tingling sensation, and combinations thereof.

[0012] The aqueous phase contains water and a cosolvent. Typical cosolvents are polyols, including propylene glycol, 1,3-propylene glycol, glycerol, butylene glycol, erythritol, xylitol, mannitol, sorbitol, isomalt, and combinations thereof. In some embodiments, the cosolvent is a mixture of propylene glycol, glycerol, and sorbitol. In a specific embodiment, propylene glycol is present at a level of 5 to 25%, glycerol is present at a level of 0.1 to 35%, and sorbitol is present at a level of 25 to 65%, all based on the weight of the flavor nanoemulsion. The weight ratio between water and cosolvent is 1:95 to 1:3, preferably 1:40 to 1:4, and more preferably 1:20 to 1:5.

[0013] The surfactant system comprises polyethoxylated sorbitan fatty acid esters and lecithin. It may be present at a level of 0.1 to 20% and the fragrance may be present at a level of 1 to 20%, both based on the weight of the fragrance nanoemulsion.

[0014] The polyethoxylated sorbitan fatty acid ester has an HLB of 9 to 20. Examples include polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, and combinations thereof.

[0015] Lecithins having an HLB of 4 to 16 may be natural, de-oiled, fractionated, or enzymatically modified.

[0016] The weight ratio between polyethoxylated sorbitan fatty acid ester and lecithin is 30: 1 to 1: 5. Polyethoxylated sorbitan fatty acid ester is typically present at a level of 0.05 to 15%, and lecithin is typically present at a level of 0.05 to 5%, both based on the weight of the fragrance nanoemulsion.

[0017] Any of the above-mentioned fragrance nanoemulsions may further contain an antifoaming agent selected from the group consisting of silicone emulsion antifoaming agents, polydimethylsiloxane antifoaming agents, 2-octanol, wax paste, hop lipids, alginates, mineral oils, sorbitan monostearate, and combinations thereof.

[0018] Another aspect of the present invention relates to a liquid beverage or liquid beverage concentrate containing any one of the above-mentioned flavor nanoemulsions. In some embodiments, the liquid beverage or liquid beverage concentrate having a turbidity of 10 NTU or less (e.g., 5 NTU or less, 3 NTU or less, and 2 NTU or less) contains 1 to 60% (e.g., 2-30%) alcohol.

[0019] Also within the scope of the present invention is a method for preparing one of the above-described fragrance nanoemulsions. The method comprises the steps of: (a) providing an aqueous phase comprising a polyethoxylated sorbitan fatty acid ester, water, and a cosolvent, (b) providing an oil phase comprising a fragrance and lecithin, and (c) emulsifying the oil phase into the aqueous phase to provide the nanoemulsion. The polyethoxylated sorbitan fatty acid ester has an HLB of 9 to 20, and the lecithin has an HLB of 4 to 16. The polyethoxylated sorbitan fatty acid ester, cosolvent, and lecithin are as defined above.

[0020] The term "free fatty acid" refers to a fatty acid containing a free carboxyl group (-COOH). Free fatty acids include their salts and solvates.

[0021] The details of one or more embodiments of the invention are set forth in the description below. Other features, objects, and advantages of the invention will be apparent from the description and from the claims. DETAILED DESCRIPTION

[0022] Many flavoring compounds used in beverage preparation are essential oils such as orange, lemon, and grapefruit, which have limited water solubility. In the beverage industry, flavor emulsions that produce optically clear beverages are of increasing interest. Ideal flavor emulsions (average particle size below 200 nanometers) are visually translucent and thermodynamically stable.

[0023] It has been unexpectedly discovered that certain flavor nanoemulsions are optically clear and maintain high stability in alcoholic beverages.These flavor nanoemulsions can be conveniently prepared from a surfactant system comprising at least polyethoxylated sorbitan fatty acid esters and lecithin.

[0024] Thus, the fragrance nanoemulsions of the present invention are generally oil-in-water systems each having a plurality of oil droplets, a continuous aqueous phase, a surfactant system, and optionally a defoaming agent.

[0025] Oil droplets are usually hydrophobic and immiscible with water. They contain one or more active materials selected from spices, oil-soluble vitamins, oil-soluble colorants, antioxidants, flavor modifiers, mouthfeel modifiers, oil-soluble defoamers, and any combination thereof. Available flavor modifiers include acid masking agents, polyaldo matric, hops, coolants, spicy flavor substances, sweeteners, salting agents, substances that cause salivation, substances that cause warm or tingling sensations, and any combination thereof. Exemplary mouthfeel modifiers are coconut oil, coconut pulp with or without sugar, vanillin, steviol glycosides such as rebaudioside A, C, D, E and F, medium-chain triglycerides, steviol, glycosylated steviol glycosides, and combinations thereof.

[0026] Other suitable active materials include fragrances, pro-fragrances, malodor counteractants, anti-inflammatories, fungicides, anesthetics, analgesics, antimicrobial actives, antivirals, anti-infectives, anti-acne agents, skin lighteners, insect repellents, emollients, skin moisturizers, wrinkle control agents, UV protectants, fabric softeners, fabric softener actives, hard surface cleaning actives, skin or hair conditioners, insect repellents, animal repellents, vermin repellents, flame retardants, antistatic agents, nano-sized inorganic solids, polymeric or elastomeric particles, and any combination thereof.

[0027] In addition to the active material, the oil droplets may also contain auxiliary materials such as viscosity modifiers and pH modifiers. The active material and auxiliary materials are described in more detail below.

[0028] When the oil droplets contain fragrance, the fragrance is present at a level of 0.1 to 20% (e.g., 0.2 to 15% and 0.5 to 10%) based on the weight of the fragrance nanoemulsion.

[0029] The oil droplets each have a droplet size of 500 nm or less, eg, 200 nm or less, 100 nm or less, 0.1 to 500 nm, 0.1 to 200 nm, and 1 to 100 nm.

[0030] The oil droplets are dispersed in an aqueous phase containing water and a cosolvent. The cosolvent is added to improve the solubility of the surfactant system in water and the stability of the nanoemulsion. Exemplary cosolvents are polyols selected from the group consisting of propylene glycol, 1,3-propanediol, glycerol, butylene glycol, erythritol, xylitol, mannitol, sorbitol, isomalt, or a combination thereof.

[0031] In some embodiments, the fragrance nanoemulsion contains an aqueous phase having a cosolvent that is a mixture of propylene glycol, glycerol, and sorbitol. In these embodiments, propylene glycol can be present at a level of 5 to 25% (e.g., 5 to 20%), glycerol is present at a level of 0.1 to 35% (e.g., 5 to 30%), and sorbitol is present at a level of 25 to 65% (e.g., 30 to 50%), all based on the weight of the fragrance nanoemulsion.

[0032] In other embodiments, the weight ratio between water and polyol is 1:95 to 1:2 (e.g., 1:95 to 1:3, 1:95 to 1:4, 1:50 to 1:3, and 1:20 to 1:5).

[0033] A surfactant system is included in the oil phase, the aqueous phase, or both. It is present at a level of 0.1 to 20% (e.g., 0.2 to 20%, 0.3 to 15%, and 0.5 to 12%) based on the weight of the nanoemulsion.

[0034] Suitable surfactant systems have at least two surfactants: polyethoxylated sorbitan fatty acid esters and lecithin. The weight ratio between polyethoxylated sorbitan fatty acid esters and lecithin is 30:1 to 1:5 (e.g., 25:1 to 1:2 and 20:1 to 1:1).

[0035] Useful polyethoxylated sorbitan fatty acid esters have an HLB of 9 to 20, preferably 13 to 20, and more preferably 14 to 18. As used herein, the term "HLB" refers to the "hydrophile-lipophile balance" of a molecule. The HLB number represents the polarity of a molecule in the range of 1-40, and most commonly used emulsifiers have values ​​between 1 and 20. With increasing hydrophilicity, the HLB number increases. As described by Griffin, "Classification of Surface-Active Agents by 'HLB'", Journal of the Society of Cosmetic Chemists 1 (1949), 311-26; and Griffin, "Calculation of HLB Values ​​for Nonionic Surfactants", Journal of the Society of Cosmetic Chemists 5 (1954), 249-56, the HLB of a surfactant can be determined by calculating values ​​for different regions of the molecule.

[0036] Suitable polyethoxylated sorbitan fatty acid esters include polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, and polyoxyethylene sorbitan monooleate. The number of repeated oxyethylene -(CH2CH2-O)- can range from 2 to 1000 (e.g., 5 to 100, 10 to 50, 10 to 30, and 20). Commercially available polyethoxylated sorbitan fatty acid esters are those available under the name Tween™ from ICI Americas, Inc. (Wilmington, Delaware), such as Tween™ 60 (HLB of 14.9), Tween™ 80 (HLB of 15), and Tween™ 20 (HLB of 16.7). They have 20 repeated oxyethylene units.

[0037] The polyethoxylated sorbitan fatty acid ester is present at a level of 0.05 to 15% (e.g., 0.1 to 12%, 0.15 to 10%, and 0.2 to 8%) based on the weight of the fragrance nanoemulsion. The weight ratio of the polyethoxylated sorbitan fatty acid ester to the fragrance can be in the range of 1:15 to 3:1 (e.g., 1:10 to 2.5:1 and 1:10 to 2:1).

[0038] Available lecithins have an HLB in the range of 4 to 16 (e.g., 6-16 and 8-16). These lecithins can be natural, de-oiled, fractionated, or enzyme-modified. Natural and standard liquid lecithins have an HLB of 4 to 8, and enzyme-modified lecithins ("lysolecithins") have an HLB of 8 to 16.

[0039] Phosphatidylcholine is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of lipid acid that is a kind of of lipid acid that is a kind of lipid acid that is a kind of of lipid acid that is a kind of lipid acid that is a kind of of lipid acid that is a kind of

[0040] Lecithin is prepared by extracting and purifying the phosphatide that derives from naturally occurring product (including but not limited to soybean, eggs, sunflower seeds or rapeseed (rapeseed), milk, ocean origin and cottonseed).Food grade lecithin obtains and comprises from commercial source with liquid, particle and powder, for example, the ALCOLEC lecithin sold by U.S. lecithin company (American Lecithin Company (Oxford, CT)) and TOPCITHIN, LECIPRIME, LECISOY, EMULFLUID, METARIN, EMULPUR, LECIGRAN, EPIKURON, LECIMULTHIN, EMULTOP and the OVOTHIN lecithin sold by CARGILL (Mechelen, Belgium), and the SOLEC lecithin sold by DuPont Nutrition and health (DuPont Nutrition&Health (St.Louis, MO)).

[0041] Lecithin can be de-oiled (that is, with 3% or less residual oil) or fractionated (that is, soluble components and insoluble components in a solvent are separated, and the solvent can be an alcohol such as ethanol or an ethanol-water mixture). During the fractionation process, lecithin mixes with an alcohol (such as ethanol or ethanol-water). Phosphatidylcholine has good solubility in ethanol, but most of other phosphatides are not fully dissolved. The ethanol phase is separated from the lecithin sludge. The removal of ethanol obtains the lecithin that is rich in phosphatidylcholine.

[0042] Preferably, phosphatidylcholine and lysophosphatidylcholine are present at a level of more than 20% based on the weight of lecithin. In addition, free fatty acids are also present in lecithin. It is desirable that their level be less than 15% (e.g., less than 10% and less than 5%) based on the weight of lecithin.

[0043] As used herein, the term "lecithin" refers to a single type of lecithin (eg, natural, de-oiled, fractionated, or enzymatically modified), as well as mixtures of lecithins.

[0044] Lecithin may be present at a level of 0.05 to 15% (e.g., 0.1 to 10% and 0.2 to 5%) based on the weight of the fragrance nanoemulsion.

[0045] In addition to polyethoxylated sorbitan fatty acid esters and lecithin, other food-safe surfactants can also be added to the flavor nanoemulsions of the present invention. Examples include ammonium phosphatide, mono- or diglycerides of fatty acids including distilled monoglycerides, acetic acid esters (Acetem) of mono- and diglycerides of fatty acids, lactic acid esters (Lactem) of mono- and diglycerides of fatty acids, citrates (Citrem) of mono- and diglycerides of fatty acids, mono- and diacetyl tartaric acid esters (Datem) of mono- and diglycerides of fatty acids, succinates (SMG) of monoglycerides of fatty acids, ethoxylated monoglycerides, sucrose esters of fatty acids, sucrose glycerides, polyglycerol esters of fatty acids, polyglycerol polyricinoleate, propane-1-of fatty acids. , 2-diol esters, thermally oxidized soybean oil interacting with mono- or di-glycerides of fatty acids, sodium stearoyl lactylate (SSL), calcium stearoyl lactylate (CSL), stearyl tartrate, sorbitan esters of fatty acids, polyglycerol esters of interesterified ricinoleic acid (E476), sodium stearoyl lactylate, sodium lauryl sulfate, polyoxyethylated hydrogenated castor oil (e.g., sold under the trade name CREMO-PHOR), block copolymers of ethylene oxide and propylene oxide (e.g., sold under the trade name PLURONIC or the trade name POLOXAMER), polyoxyethylene fatty alcohol ethers, and polyoxyethylene stearates. Examples of sorbitan esters of fatty acids are sorbitan monostearate, sorbitan tristearate, sorbitan monolaurate, sorbitan monooleate, sorbitan monopalmitate, and sucrose esters of fatty acids.

[0046] Optionally, the fragrance nanoemulsion contains an antifoaming agent, which can be a water-dispersible antifoaming agent or an oil-soluble antifoaming agent. Examples include silicone emulsion antifoaming agents, polydimethylsiloxane antifoaming agents, 2-octanol, wax paste, hop lipids (hoplipid), alginates, mineral oil, sorbitan monostearate, and combinations thereof.

[0047] The flavor nanoemulsions are translucent or optically clear. They can be added to alcoholic or non-alcoholic, carbonated or non-carbonated beverage base solutions to enhance the flavor, taste, or mouthfeel of the beverage. When a clear beverage base solution is used, the final beverage remains optically clear while gaining the benefits of flavor enhancement through the introduction of the nanoemulsions of the present invention.

[0048] The term "translucent" refers to a nanoemulsion that is visible through, although light may be diffused by the material itself. In this regard, the nanoemulsions of the present invention provide a clear soft drink. The term "clear" or "optically clear" (transparent) refers to a nanoemulsion or beverage that has a turbidity of less than 10 Nephelometric Turbidity Units (NTUs); for example, less than 5 NTUs and less than 3 NTUs. Turbidity can be measured according to procedures known in the art, for example, Fernandez et al., Food Chemistry (2000), 71, 563-66; and Christensen et al., Journal - American Water Works Association (2003), 95, 179-189.

[0049] The fragrance nanoemulsions of the present invention have low water levels. Some fragrance nanoemulsions contain less than 25% (e.g., less than 20%, less than 15%, 1 to 20%, 5-20%) water. Each fragrance nanoemulsion has a water activity of less than 0.7 (e.g., less than 0.65, less than 0.6, and less than 0.55).

[0050] Water activity is the ratio between the vapor pressure of the fragrance nanoemulsion when in completely undisturbed equilibrium with the surrounding air medium and the vapor pressure of distilled water under the same conditions. A water activity of 0.7 means a vapor pressure that is 70% of that of pure water. Using this specific definition, pure distilled water has a water activity of exactly one. Water activity generally increases with increasing temperature.

[0051] A higher water activity is necessary to support microbial growth. Bacteria generally require a water activity of at least 0.91, and fungi at least 0.7.

[0052] With a water activity below 0.7, the fragrance nanoemulsion of the present invention will not support the growth of microorganisms.Therefore, the fragrance nanoemulsion is generally free of preservatives.

[0053] In certain embodiments, the fragrance nanoemulsion further contains 0.01% to 20% carrier material in aqueous phase, which includes monosaccharides and disaccharides, such as glucose, lactose, levulose, trehalose, fructose, maltose, ribose, sucrose or a combination thereof. In other embodiments, the aqueous phase further contains protein, glue and / or hydrocolloid. Suitable protein includes soy protein isolate, soy protein concentrate, whey protein isolate, whey protein concentrate, gelatin, pea protein and protein hydrolysate. The example of glue and hydrocolloid includes xanthan gum, guar gum, gum arabic (gum acaia), chemically modified gum arabic, pectin and alginate.

[0054] The fragrance nanoemulsion of the present invention is prepared by emulsifying fragrance oil into an aqueous phase using conventional techniques in the presence of polyethoxylated sorbitan fatty acid esters and lecithin. In short, nanoemulsions are typically prepared by mixing the aqueous phase and the oil phase and homogenizing the mixture several times (or, in the terminology of this field, performing more than one "pass"). According to the present invention, the pre-emulsion step (i.e., the high shear mixing step) is important for setting the initial particle size before high-pressure homogenization. The speed of high shear mixing can be in the range of 3,000 rpm to 20,000 rpm and the mixing time can be in the range of 5 to 30 minutes. Subsequently, a high-pressure homogenizer (e.g., the commercially available Niro Panda 2000) or other types of homogenizers (e.g., the MICROFLUIDIZER commercially available from Microfluidics or the EMULSIFLEX commercially available from Avestin) is used to prepare the nanoemulsion. Homogenization may be performed using a two-stage homogenizer at 3,000 / 300 psi to 10,000 / 1,000 psi for two, three, or more passes; or at 6,500 / 500 psi to 20,000 / 2,000 psi for one, two, or more passes.

[0055] Instant fragrance nanoemulsions can be used in a variety of consumer products, foods, or pharmaceuticals. In particular, fragrance nanoemulsions have found applications in chewing gum, pastries, oral care products, beverages, snacks, dairy products, soups, sauces, condiments, detergents, fabric softeners and other fabric care products, antiperspirants, deodorants, talc, cat litter, hair care and styling products, personal care products, air fresheners, cereals, baked goods, and cleaners.

[0056] In a specific embodiment, the instant flavor nanoemulsion is used in beverages and beverage liquid concentrates.Thus, in addition to the flavor nanoemulsion, the present invention also provides an optically clear finished beverage product or liquid beverage concentrate containing the flavor nanoemulsion of the present invention.

[0057] In some embodiments, the instant flavor nanoemulsion is dosed at a level between 1 ppm and 60% (e.g., 1 ppm to 20% and 5 ppm to 5%) based on the weight of the final beverage product, such that the product contains 0.01 ppm to 10% (0.1 ppm to 5%, 0.5 ppm to 1%, and 1 ppm to 100 ppm) flavor oil. When the flavor emulsion of the present invention is used, the final beverage product prepared therefrom is clear, having a turbidity of 10 NTU (e.g., 5 NTU and 3 NTU) or less.

[0058] As used herein, the term "liquid beverage concentrate" means a liquid composition that can be diluted with another liquid (such as an aqueous drinkable liquid) to provide a finished beverage or added to a food product before consumption. The phrase "liquid" refers to a non-gassy, ​​flowable, liquid composition at room temperature (i.e., 70°F). As used herein, the term "finished beverage" means a beverage that has been prepared through standard soft drink (i.e., ready-to-drink) preparation procedures or by diluting a concentrate to provide a drinkable, consumable beverage. In some aspects, a concentrate is non-drinkable due to its acidulant content and / or flavor intensity. By way of example, by way of illustration of the term "concentration," a 75-fold (i.e., "75X") concentration would be equivalent to 74 parts water (or other drinkable liquid) for 1 part concentrate to provide the finished beverage. In other words, the flavor profile of the finished beverage is taken into consideration when determining the appropriate dilution level, and therefore the concentration, of a liquid beverage concentrate. The dilution factor of a concentrate can also be expressed as the amount required to provide one portion of concentrate.

[0059] The viscosity, pH, and formulation of the concentrate will depend, at least in part, on the intended dilution factor. In one approach, a moderately concentrated product can be formulated to be diluted by a factor of at least 5 to provide a final beverage, which can be, for example, an 8 oz beverage. In one aspect, the concentrate is formulated to be diluted by a factor of 5 to 15 to provide a final beverage. In this form, the liquid concentrate has a pH of 1.8 to 4, or more specifically 1.8 to 2.9, 2 to 3.1, or 2 to 2.5; and a viscosity of 7.5 to 100 cP, 10 to 100 cP, 15 to 100 cP, 10 to 50 cP, or 10 to 20 cP as measured using a Brookfield DVII + Pro viscometer at 50 rpm and 20° C. using a spindle S00. In some embodiments, the concentrate comprises at least 0.1 to 15 percent of an acidulant, based on the weight of the concentrate. If desired, any edible, food grade organic or inorganic acid can be used, such as, but not limited to, citric acid, malic acid, succinic acid, acetic acid, hydrochloric acid, adipic acid, tartaric acid, fumaric acid, phosphoric acid, lactic acid, sodium acid pyrophosphate, their salts and their combinations. The selection of acidulant can depend at least in part on the desired pH of the concentrate and / or the taste that the acidulant imparts to the final beverage of the dilution. In another aspect, the amount of the acidulant included in the concentrate can depend on the intensity of the acid. For example, compared with stronger acids such as phosphoric acid, a larger amount of lactic acid will be needed in the concentrate to reduce the pH in the final beverage. In some embodiments, a buffer can be added to the concentrate to provide an increased acid content at the desired pH. Suitable buffers include, for example, the conjugate base of the acid, gluconate, acetate, phosphate or any salt of the acid (for example, sodium citrate and potassium citrate). In other examples, the undissociated salt of the acid can buffer the concentrate.

[0060] Beverages or concentrates of the present invention can include one or more fruit juices or fruit juice concentrates (e.g., at least 4X concentrated products) from fruits or vegetables added for bulk solids. In one aspect, the fruit juices or fruit juice concentrates can include, for example, coconut water (also commonly referred to as coconut water), apples, pears, grapes, oranges, potatoes, mandarins, lemons, limes, tomatoes, carrots, beets, asparagus, celery, kale, spinach, pumpkins, strawberries, raspberries, bananas, blueberries, mangoes, passion fruit, peaches, plums, papayas, and combinations. If desired, the fruit juices or fruit juice concentrates can also be added as purees.

[0061] As pointed out, can be added in drinking liquid to form flavored beverage.In some respects, concentrate can be non-drinking (as due to high acid content and flavor intensity).For example, beverage concentrate can be used to think that water, cola, carbonated water, tea, coffee, Seltzer mineral water (seltzer), soda water (club soda) etc. provide fragrance, and can also be used to enhance the fragrance of fruit juice.In one embodiment, beverage concentrate can be used to think that alcoholic beverage provides fragrance, and described alcoholic beverage includes but is not limited to flavoring champagne, sparkling wine (sparkling wine), grape sparkling wine (winespritzer), cocktail, martini (martini) etc.In a specific embodiment, concentrate is used in optically clear beverage.

[0062] Beverage concentrates can also be combined with various food products to add flavor to the food products. For example, the concentrates can be used to provide flavor to various solid, semi-solid, and liquid food products, including but not limited to oatmeal, cereals, yogurt, dehydrated yogurt, cottage cheese, cream cheese, frosted sugar, salad dressings, sauces, and desserts such as ice cream, sherbet, sorbet, and Italian ice. The appropriate ratio of beverage concentrate to food or beverage can be readily determined by one of ordinary skill in the art.

[0063] For the purposes of this invention, stability is defined as maintaining acceptable flavor quality and intensity for use in the end use.Preferably, a stable emulsion has a shelf life of at least one year to three years depending on storage conditions.

[0064] Nanoemulsions are lipid droplets with a diameter of less than 200 nanometers (e.g., 50 to 150 nanometers). See Mason et al., 2006, J. Physics: Condensed Matter 18, 635-66. Nanoemulsions are prepared by mixing a water-immiscible oil phase into an aqueous phase using a high-stress mechanical process.

[0065] The fragrance oil suitable for preparing the nanoemulsion of the present invention contains one or more volatile and non-volatile compounds. Various spices can be used according to the present invention. Spices can be selected from synthetic spices, flavoring oils and oil extracts derived from plants, leaves, flowers, fruits, and combinations thereof. Representative fragrance oils include, but are not limited to, spearmint oil, cinnamon oil, peppermint oil, clove oil, bay oil, thyme oil, cedar leaf oil, nutmeg oil, sage oil, and bitter almond oil. Also available are artificial, natural or synthetic fruit flavors such as vanilla, chocolate, coffee, cocoa and citrus oils (including lemon, orange, grape, lime and grapefruit) and fruit essences (including apple, pear, peach, strawberry, watermelon, raspberry, cherry, plum, pineapple, apricot, etc.). These spices can be used alone or in combination.

[0066] Volatile compounds in flavor oils may include, but are not limited to, acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate. Flavors containing volatile aldehydes or esters include, for example, cinnamyl acetate, cinnamaldehyde, citral, diethyl acetal, dihydrocarvyl acetate, eugenyl formate, and p-methylanisole. Additional examples of volatile compounds that may be present in flavor oils include acetaldehyde (apple); benzaldehyde (cherry, almond); cinnamaldehyde (cinnamon); citral, i.e., α-citral (lemon, lime); neral, i.e., β-citral (lemon, lime); decanal (orange, lemon); ethyl vanillin (vanilla, cream); piperonal, i.e., piperonal (vanilla, cream); vanillin (vanilla, cream); α-amylcinnamaldehyde (spicy fruit flavor); butyraldehyde (butter, cheese); valeraldehyde (butter, cheese); vanilla Calendula (modifier, various types); decanal (citrus fruits); aldehyde C-8 (citrus fruits); aldehyde C-9 (citrus fruits); aldehyde C-12 (citrus fruits); 2-ethylbutyraldehyde (berries); hexanal, i.e., trans-2 (berries); toluylaldehyde (cherries, almonds); veratraldehyde (vanilla); 2,6-dimethyl-5-heptanal, i.e., melonal (melon); 2-6-dimethyloctanal (green fruits); and 2-dodecanal (citrus, oranges); cherries; or grapes, and mixtures thereof. The composition may also contain flavor modifiers and artificial sweeteners.

[0067] The physical, chemical, and odor properties of selected volatile compounds are given in Table 1.

[0068] Table 1

[0069]

[0070] *Good Scents Company and Merck Index 12th Edition

[0071] The fragrance nanoemulsion may also contain the following active materials:

[0072] (i) Taste masking agents, substances used to mask one or more unpleasant taste sensations, especially bitter, astringent and / or metallic taste sensations or aftertastes. Examples include lactisol [2-O-(4-methoxyphenyl) lactic acid] (see U.S. Pat. No. 5,045,336), potassium salt of 2,4-dihydroxybenzoic acid (see U.S. Pat. No. 5,643,941), ginger extract (see GB 2,380,936), neohesperidin dihydrochalcone (see Manufacturing Chemist 2000, July issue, pages 16-17), certain flavonoids (2-phenylchrome-2-en-4-one) (see U.S. Pat. No. 5,580,545), certain nucleotides, such as cytidine-5'-monophosphate (CMP) (see US 2002 / 0177576), certain sodium salts, such as sodium chloride, sodium citrate, sodium acetate and sodium lactate (see Nature, 1997, Vol. 387, page 563), lipoproteins of β-lactoglobulin and phosphatidic acid (see EPA 635). 218), neodiosmine [5,7-dihydroxy-2-(4-methoxy-3-hydroxyphenyl)-7-O-neohesperidosyl-chrome-2-en-4-one] (cf. U.S. Pat. No. 4,154,862), preferably a hydroxyflavanone according to EP 1 258 200, and in this respect further preferably according to WO 2-(4-Hydroxyphenyl)-5,7-dihydroxychroman-4-one (naringenin), 2-(3,4-dihydroxyphenyl)-5,7-dihydrochroman-4-one (eriodictyol), 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychroman-4-one (eriodictyol-7-methyl ether), 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychroman-4-one (eriodictyol-5-methyl ether) and 2-(4-hydroxy-3-methoxyphenyl)-5,7-dihydrochroman-4-one (homoeriodictyol) of 2005 / 09684, their (2S)- or (2R)-enantiomers or mixtures thereof and their reaction products with Na as countercation + , K + NH4 + , Ca 2+ Mg 2+ or Al 3+ monovalent or polyvalent phenolates or gamma-aminobutyric acid (4-aminobutyric acid, either in neutral form ("internal salt") or in carboxylate or ammonium form);

[0073] (ii) Taste sensates, including spicy taste, salivation-inducing substances, substances causing a warming or tingling sensation, and cooling active ingredients. Examples of substances that have a spicy taste and / or salivation-inducing substances and / or that cause a warming and / or tingling sensation on the skin or on the mucous membranes and that can be ingredients of the product according to the invention are: capsaicin, dihydrocapsaicin, gingerol, paradol, shogaol, piperine, carboxylic acid-N-vanillylamide, in particular nonanoic acid-N-vanillylamide, pellitorin or spilanthol, 2-nonanoic acid amides, in particular 2-nonanoic acid-N-isobutylamide, 2-nonanoic acid-N-4-hydroxy-3-methoxybenzylamide, alkyl ethers of 4-hydroxy-3-methoxybenzyl alcohol, in particular 4-hydroxy-3-methoxybenzyl-n-butyl ether, 4-acyloxy- Alkyl ethers of 3-methoxybenzyl alcohol, in particular 4-acetoxy-3-methoxybenzyl-n-butyl ether and 4-acetoxy-3-methoxybenzyl-n-hexyl ether, alkyl ethers of 3-hydroxy-4-methoxybenzyl alcohol, alkyl ethers of 3,4-dimethoxybenzyl alcohol, alkyl ethers of 3-ethoxy-4-hydroxybenzyl alcohol, alkyl ethers of 3,4-methylenedioxybenzyl alcohol, (4-hydroxy-3-methoxyphenyl)acetic acid amide, in particular (4-hydroxy-3-methoxyphenyl)acetic acid-N-n-octylamide, vanillylmandelic acid alkylamide, ferulic acid-phenylacetamide, nicotinaldehyde, methyl nicotinate, propyl nicotinate, 2-butoxyethyl nicotinate, benzyl nicotinate, 1-acetoxybenzene, polygodial and isodrimeninol, more preferably according to WO cis- and / or trans-serratocarps according to WO 2004 / 000787 or WO 2004 / 043906, olefincarboxylic acid N-alkylamides according to WO 2005 / 044778, mandelic acid alkylamides according to WO 03 / 106404 or alkoxyalkanoic acid amides according to WO 2006 / 003210. Examples of preferred natural extracts with a pungent taste and / or natural extracts that cause a warming and / or tingling sensation on the skin or on the mucous membranes and that can be ingredients of the products according to the invention are: extracts of paprika, extracts of pepper (e.g. capsicum extract), extracts of chili pepper, extracts of ginger root, extracts of Aframomum melgueta, extracts of Spilanthes acmella, extracts of Kaempferia galangal or extracts of Alpinia galanga.Suitable cooling active ingredients include the following: l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat.RTM.MGA), menthyl lactate (trade name: Frescolat.RTM.ML, menthyl lactate is preferably l-menthyl lactate, especially l-menthyl lactate), substituted menthyl-3-carboxylic acid amides (for example menthyl-3-carboxylic acid-N-acetamide), 2-isopropyl-N-2,3-trimethyl-butyramide, substituted cyclohexanecarboxylic acid amides, 3-aminobenzoic acid benzoate, benzophenone ... -menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, N-acetylglycine menthyl, isopulegol, menthyl hydroxycarboxylates (e.g., menthyl 3-hydroxybutyrate), monomenthyl succinate, 2-mercaptocyclodecanone, menthyl 2-pyrrolidino-5-onecarboxylate, 2,3-dihydroxy-p-menthane, 3,3,5-trimethylcyclohexanone glycerol ketal, 3-menthyl 3,6-dioxaalkanoate and 3-menthyl 3,6-trioxaalkanoate, 3-menthyl methoxyacetate and icilin. Particularly preferred cooling active ingredients are as follows: l-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat.RTM.MGA), menthyl lactate (preferably l-menthyl lactate, especially l-menthyl lactate, trade name: Frescolat.RTM.ML), 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate;.

[0074] (iii) Vitamins, including any vitamin, its derivatives, and salts thereof. Examples include vitamin A and its analogs and derivatives (e.g., retinol, retinal, retinyl palmitate, retinoic acid, tretinoin, and isotretinoin, collectively referred to as retinoids), vitamin E (tocopherol and its derivatives), vitamin C (L-ascorbic acid and its esters and other derivatives), vitamin B3 (niacinamide and its derivatives), alpha hydroxy acids (e.g., glycolic acid, lactic acid, tartaric acid, malic acid, citric acid, etc.), and beta hydroxy acids (e.g., salicylic acid, etc.);

[0075] (iv) antibacterial agents, including bisguanidine (e.g., chlorhexidine digluconate), diphenyl compounds, benzyl alcohol, trihalodiphenyl ureas, quaternary ammonium compounds, ethoxylated phenols, and phenolic compounds, such as halogen-substituted phenolic compounds, such as PCMX (i.e., p-chloro-m-xylenol), triclosan (i.e., 2,4,4'-trichloro-2'hydroxy-diphenyl ether), thymol, and triclocarban;

[0076] (v) antioxidants, such as β-carotene, vitamin C (ascorbic acid) or its esters, vitamin A or its esters, vitamin E or its esters, lutein or its esters, lignans, lycopene, selenium, flavonoids, vitamin-like antioxidants such as coenzyme Q10 (CoQ10) and glutathione, and antioxidant enzymes such as superoxide dismutase (SOD), catalase, and glutathione peroxidase;

[0077] (vi) Anti-inflammatory agents, including, for example, methyl salicylate, aspirin, ibuprofen, and naproxen. Additional anti-inflammatory agents that may be used for topical application include corticosteroids such as, but not limited to, flurandrenolide, clobetasol propionate, halobetasol propionate, fluticasone propionate, betamethasone dipropionate, betamethasone benzoate, betamethasone valerate, desoximethasone, dexamethasone, diflorasone diacetate, mometasone furoate, amcinodine, halcinonide, fluocinonide, fluocinolone acetonide, and halcinonide. acetonide, desonide, triamcinoloneacetonide, hydrocortisone, hydrocortisone acetate, fluoromethalone, methylprednisolone, and predinicarbate;

[0078] (vii) anesthetics that can be delivered topically, including benzocaine, butamben, butamben picrate, procaine, tetracaine, lidocaine, and pramoxine hydrochloride;

[0079] (viii) analgesics, such as ibuprofen, diclofenac, capsaicin, and lidocaine;

[0080] (ix) Antifungal agents. Non-limiting examples are miconazole, clotrimazole, butoconazole, fenticonazole, tioconazole, terconazole, sulconazole, fluconazole, haloprogin, ketonazole, ketoconazole, oxinazole, econazole, itraconazole, torbinafine, nystatin, and griseofulvin;

[0081] (x) Antibiotics, such as erythromycin, clindamycin, synthomycin, tetracycline, metronidazole, etc.;

[0082] (xi) antiviral agents, including famcyclovir, valacyclovir, and acyclovir;

[0083] (xii) antiparasitic agents, such as scabies, for example, permethrin, crotamiton, lindane and ivermectin;

[0084] (xiii) anti-infective / anti-acne agents, including benzoyl peroxide, sulfur, resorcinol, and salicylic acid;

[0085] (xiv) enzymes and coenzymes, including coenzyme Q10, papain, lipase, protease, superoxide dismutase, deoxyribonuclease, trypsin, collagenase, and sutilain;

[0086] (xv) antihistamines, including chlorpheniramine, brompheniramine, dexchlorpheniramine, tripolidine, clemastine, diphenhydramine, promethazine, piperazine, piperidine, astemizole, loratadine, and terfonadine;

[0087] (xvi) chemotherapeutic agents such as 5-fluorouracil, masoprocol, mechlorethamine, cyclophosphamide, vincristine, chlorambucil, streptozocin, methotrexate, bleomycin, dactinomycin, daunorubicin, coxorubicin, and tamoxifen; and

[0088] In addition to the active ingredients listed above, the products of the present invention may also contain, for example, the following dyes, colorants or pigments: lactoflavin (riboflavin), β-carotene, riboflavin-5'-phosphate, α-carotene, γ-carotene, canthaxanthin, erythrosine, curcumin, quinoline yellow, yellow orange S, tartrate, annatto, norannatto (annatto, orlean), capsanthin, capsorubin, lycopene, β-apo-8'-carotenal, β-apo-8'-carotenic acid ethyl ester, xanthophylls (ranunculus xanthophylls, lutein, cryptoxanthin, rubixanthin, violaxanthin, purpurogenol), fast carmine (carminic acid, carmine), azorubin, carmine A (ponceau 4 R), beetroot red, beet red, anthocyanins, amaranth, patent blue V, indigo I (indigo-carmine), chlorophyll, copper compounds of chlorophyll, acid brilliant green BS (lissamine green), brilliant black BN, vegetable carbon, titanium dioxide, iron oxides and hydroxides, calcium carbonate, aluminum, silver, gold, pigment ruby ​​​​BK (lithol ruby ​​​​BK), methyl violet B, Victoria Blue R, Victoria Blue B, acilan Brilliant Blue FFR (Brilliant Wool Blue FFR), naphthol Green B, acilan Fast Green 10 G (Alkali Fast Green 10 G), ceres Yellow GRN, Sudan Blue II, ultramarine, phthalocyanine blue, phthalocyanine green, acid fast violet R. Additional naturally obtained extracts (such as red pepper extract, black carrot extract, red cabbage extract) can be used for coloring purposes. Good results have also been achieved with the colors named after the so-called aluminum lakes: FD&C Yellow 5 Lake, FD&C Blue 2 Lake, FD&C Blue 1 Lake, Tartar Yellow Lake, Quinoline Yellow Lake, FD&C Yellow 6 Lake, FD&C Red 40 Lake, Sunset Yellow Lake, Carmoisine Lake, Amaranth Lake, Ponceau 4R Lake, Erythromycin Lake, Red 2G Lake, Allura Red Lake, Patent Blue V Lake, Indigo Carmine Lake, Brilliant Blue Lake, Brown HT Lake, Black PN Lake, Green S Lake, and mixtures thereof.

[0089] Supplementary Materials

[0090] In addition to the active material, the present invention also contemplates combining one or more auxiliary materials, including solvents, emollients, solubility modifiers, density modifiers, stabilizers, viscosity modifiers, pH modifiers, or any combination thereof. These modifiers can be present in the aqueous phase or the oil phase.

[0091] One or more adjunct materials may be added in an amount of 0.01% to 25% (e.g., 0.5% to 10%) based on the weight of the fragrance nanoemulsion.

[0092] (i) Solvents. Preferred solvent materials are hydrophobic and miscible with the active material. Solvents increase the compatibility of various active materials, increase the overall hydrophobicity of the mixture containing the active material, affect the vapor pressure, or are used to construct the mixture. It should be noted that selecting a solvent and active material that have a high affinity for each other will result in improved stability. Exemplary solvents are triglyceride oils, mono- and di-glycerides, mineral oil, silicone oil, diethyl phthalate, poly-alpha-olefins, castor oil, isopropyl myristate, mono-, di- and triesters and mixtures thereof, fatty acids, and glycerol. The fatty acid chain can be between C4 and C5. 26 range and can have any level of unsaturation. For example, one of the following solvents can be used: capric / caprylic triglyceride known as NEOBEE M5 (Stepan Corporation); the CAPMUL series (e.g., CAPMUL MCM) from Abitec Corporation; isopropyl myristate; fatty acid esters of polyglycerol oligomers, such as R 2 CO-[OCH2-CH(OCOR 1 )-CH 2 O-] n , where R 1 and R 2 Can be H or C4-C 26aliphatic chains, or mixtures thereof, with n ranging from 2 to 50, preferably from 2 to 30; nonionic fatty alcohol alkoxylates, such as BASF's NEODOL surfactants; Shell Corporation's dobanol surfactants or Stepan's BIO-SOFT surfactants, wherein the alkoxy groups are ethoxy, propoxy, butoxy, or mixtures thereof and the surfactants may be terminated with methyl groups to increase their hydrophobicity; di- and tri-fatty acid chain-containing nonionic, anionic, and cationic surfactants, and mixtures thereof; fatty acid esters of polyethylene glycol, polypropylene glycol, and polybutylene glycol, or mixtures thereof; polyalphaolefins such as EXXONMOBIL PURESYM PAO line; esters such as EXXONMOBIL PURESYN esters; mineral oils; silicone oils such as polydimethylsiloxane and polydimethylcyclosiloxane; diethyl phthalate; dioctyl adipate and diisodecyl adipate. In certain embodiments, the ester oil has at least one ester group in the molecule. One type of commonly used ester oil that can be used in the present invention is fatty acid monoesters or polyesters, such as cetyl octanoate, octyl isononanoate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glyceryl monostearate, glyceryl distearate, glyceryl tristearate, alkyl lactates, alkyl citrates, and alkyl tartarates; sucrose esters and polyesters, sorbitol esters, etc. The second type of ester oil that can be used is mainly composed of triglycerides and modified triglycerides. These include vegetable oils such as jojoba, soybean, rapeseed, sunflower, safflower, rice bran, avocado, almond, olive, sesame, peach kernel, castor, coconut, and mink oil. Synthetic triglycerides can also be used, provided that they are liquid at room temperature. Modified triglycerides include materials such as ethoxylated and maleated triglyceride derivatives, provided they are liquid. Proprietary ester blends, such as those sold by FINEX as FINSOLV, are also suitable, such as ethylhexanoin. A third class of ester oils are liquid polyesters formed by the reaction of dicarboxylic acids and glycols. An example of a polyester suitable for use in the present invention is the polyester sold by EXXONMOBIL under the trade name PURESYN ESTER.

[0093] (ii) Triglycerides and modified triglycerides as emollients. These include vegetable oils such as jojoba, soy, rapeseed, sunflower, safflower, rice bran, avocado, almond, olive, sesame, peach, castor, coconut, and mink oils.

[0094] (iii) Ester oils have at least one ester group in the molecule. One type of common ester oil useful in the present invention is fatty acid monoesters or polyesters, such as cetyl octanoate, octyl isononanoate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glyceryl monostearate, glyceryl distearate, glyceryl tristearate, alkyl lactates, alkyl citrates, and alkyl tartarates.

[0095] (iv) Ester oils which are liquid polyesters formed by the reaction of a dicarboxylic acid and a diol. An example of a polyester suitable for the present invention is the polyester sold under the trade name PURESYN ESTER.RTM by ExxonMobil, a hydrophobic plant extract.

[0096] (v) Silicones include, for example, linear and cyclic polydimethylsiloxanes, amino-modified, alkyl, aryl, and alkaryl silicone oils.

[0097] (vi) Low / non-volatile hydrocarbons

[0098] (vii) Solubility modifiers. Non-limiting examples of solubility modifiers include surfactants (e.g., SLS and Tween 80), acidic compounds (e.g., inorganic acids such as sulfuric acid, hydrochloric acid, nitric acid, and phosphoric acid, and carboxylic acids such as acetic acid, citric acid, gluconic acid, glucoheptonic acid, and lactic acid), basic compounds (e.g., ammonia, alkali metal and alkaline earth metal hydroxides, primary, secondary, or tertiary amines, and primary, secondary, or tertiary alkanolamines), ethanol, glycerol, glucose, galactose, inositol, mannitol, glactitol, ribitol, arabitol, and amino acids.

[0099] (viii) Density modifiers. The density of the perfume oil droplets and perfume nanoemulsions can be adjusted to provide a substantially uniform distribution of the nanoemulsion using known density modifiers or techniques, such as those described in patent application publications WO 2000 / 059616, EP 1 502 646, and EP 2 204 155. Suitable density modifiers include hydrophobic materials and materials having a desired molecular weight (e.g., greater than about 12,000), such as silicone oils, wax pastes, vegetable oils (particularly sunflower oil and rapeseed oil), and hydrophobic solvents having a desired density (e.g., less than about 1,000 Kg / m at 25° C.), such as limonene and octane.

[0100] (ix) Stabilizers. In some embodiments, stabilizers (e.g., colloidal stabilizers) are added to stabilize the emulsion. Examples of colloidal stabilizers are polyvinyl alcohol, cellulose derivatives such as hydroxyethyl cellulose, polyethylene oxide, copolymers of polyethylene oxide and polyethylene or polypropylene oxide, or copolymers of acrylamide and acrylic acid.

[0101] (x) Viscosity control agents. Viscosity control agents (e.g., suspending agents) can be included in the fragrance nanoemulsion, which can be polymers or colloids (e.g., modified cellulose polymers such as methylcellulose, hydroxyethylcellulose, hydrophobically modified hydroxyethylcellulose, and cross-linked acrylate polymers such as carbomers, hydrophobically modified polyethers). Optionally, silica, whether hydrophobic or hydrophilic, can be included at a concentration of 0.01 to 20%, more preferably 0.5 to 5%, based on the weight of the fragrance nanoemulsion. Examples of hydrophobic silicas include silanols, alkoxysilanes, silazanes, and siloxanes whose surfaces are treated with halogen silanes, such as SIPERNAT D17, AEROSIL R972, and R974 available from Degussa. Exemplary hydrophilic silicas are AEROSIL 200, SIPERNAT 22S, SIPERNAT 50S (available from Degussa), and SYLOID 244 (available from Grace Davison).

[0102] (xi) pH adjusters. In some embodiments, one or more pH adjusters are included in the nanoemulsion to adjust the pH. Exemplary pH adjusters include metal hydroxides (e.g., LiOH, NaOH, KOH, and Mg(OH)), metal carbonates and bicarbonates (CsCO3, Li2CO3, K2CO3, NaHCO3, and CaCO3), metal phosphates / hydrogenphosphates / dihydrogenphosphates, metal sulfates, ammonia, inorganic acids (HCl, H2SO4, H3PO4, and HNO3), carboxylic acids (e.g., acetic acid, citric acid, lactic acid, benzoic acid, and sulfonic acid), and amino acids.

[0103] Levels of adjunct materials may be present at levels of 0.01 to 25% (e.g., 0.5% to 10%) or greater than 10% (e.g., greater than 30% and greater than 70%).

[0104] Other modifications of the present invention will be apparent to those skilled in the art. It should be understood that such modifications are within the scope of the present invention. Additionally, unless otherwise specified, all parts, percentages, proportions, and ratios herein and in the claims are generally referred to as being based on weight.

[0105] Unless otherwise indicated, all parts, percentages and ratios herein and in the claims are by weight.

[0106] The values ​​and dimensions disclosed herein should not be understood as being strictly limited to the exact numerical values ​​recited. Instead, unless otherwise specified, each such value is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a value disclosed as "50%" is intended to mean "about 50%."

[0107] All publications cited herein are incorporated by reference in their entirety.

[0108] The present invention is described in more detail by the following non-limiting examples.

[0109] Example 1

[0110] The fragrance nanoemulsion of the present invention, namely Emulsion I, was prepared according to the following procedure.

[0111] The aqueous phase was prepared by dissolving 420 grams of sorbitol, 170 grams of glycerol, and 172 grams of propylene glycol in 180 grams of water, followed by the addition of 25 grams of Tween® while high shear mixing using a Silverson high shear mixer (SILVERSON) model L4RT at 6,500 rpm for 3 minutes. TM 60 (polyethoxylated sorbitan fatty acid esters, commercially available from Croda, Edison, NJ). In a separate flask, an oil phase was prepared by mixing 3 grams of standard liquid lecithin (HLB of approximately 4) and 30 grams of lemon flavor (International Flavors and Frances, Union Beach, NJ). Subsequently, a pre-emulsion was formed by mixing the oil phase and the aqueous phase under high shear mixing at 6,500 rpm for 3 minutes. The pre-emulsion was further processed three times at 5,000 psi in a high-pressure microfluidizer (Model M-110P, Microfluidics, Westwood, MA) to obtain 1,000 grams of Emulsion 1.

[0112] Water activity was measured using an AquaLab dew point water activity meter (Model 4TEV, Decagon Devices, Inc., Pullman, Washington, USA). Emulsion 1 had a water activity of 0.53.

[0113] Example 2

[0114] Another nanoemulsion of the present invention, Emulsion II, was prepared by following the same procedure as Emulsion I, except that 3 g of enzyme-modified lecithin SOLEC K-EML (commercially available from DuPont Nutrition & Health, St. Louis, MO, USA, HLB of approximately 8) was used instead of standard liquid lecithin.

[0115] Comparing Lotions

[0116] Comparative Emulsion I' was prepared following the same procedure as Emulsion I, except that standard liquid lecithin was not used and an additional 3 grams of glycerol was added so that the total weight of the emulsion was still 1000 grams.

[0117] Comparative emulsion II' was prepared by the same procedure as emulsion I, except that (i) 24 g of enzyme-modified lecithin ALCOLEC C LPC20 (America Lecithin Company, Oxford, CT, USA) was used instead of Tween TM 60, (ii) reducing the amount of standard liquid lecithin to 2.4 g, and (iii) increasing the amount of glycerol to 171.6 g.

[0118] Comparative emulsion III' was prepared by the same procedure as emulsion I, except that (i) 35 g of fractionated lecithin ALCOLEC PC75 (America Lecithin Company, Oxford, CT, USA) was used instead of Tween TM 60, (ii) reducing the amount of standard liquid lecithin to 2.4 g, and (iii) reducing the amount of glycerol to 160.6 g.

[0119] Examples 3 and 4: Alcoholic Beverages

[0120] The beverage of the present invention, Beverage A, was prepared according to the following procedure. More specifically, 0.1% (weight / volume) of Emulsion I was added to an alcoholic beverage solution (8% alcohol) prepared by diluting an alcoholic syrup with water at a ratio of 1:3 (syrup:water). The alcoholic syrup formulation is given in Table 2 below.

[0121] Table 2

[0122]

[0123] The turbidity of the beverage was measured at time zero and after one day using a turbidimeter (HACH Model 2100Q0) in nephelometric turbidity units (NTUs) as specified by the U.S. Environmental Protection Agency. The measurements were performed according to the procedure described in the "Turbidity Measurement" section of the turbidimeter's owner's instruction manual. The results are shown in Table 3 below.

[0124] Beverage B was prepared following the same procedure as Beverage A, except that Emulsion II was used instead of Emulsion I.

[0125] Comparative beverages A', B', and B" were prepared using comparative emulsions I', II', and III', respectively.

[0126] The turbidity of Beverage B and Comparative Beverage A' was measured. The results are shown in Table 3 below.

[0127] Table 3

[0128]

[0129] As shown in Table 3 above, each of the inventive beverages A and B surprisingly had much lower turbidity than the comparative example, both at time zero and after one day.

[0130] Examples 5 and 6: Non-alcoholic beverages

[0131] The beverage of the present invention, Beverage C, was prepared according to the procedure described below. More specifically, 0.1% (weight / volume) of Emulsion I was mixed with a non-alcoholic beverage solution, which was prepared using the formulation shown in Table 4 below.

[0132] The turbidity of Beverage H was measured at time zero and after 1 day.

[0133] Table 4

[0134]

[0135] Beverage D of the present invention was prepared according to the same procedure as for Beverage C, except that Emulsion II was used instead of Emulsion I.

[0136] Comparative Beverage C' was prepared following the same procedure as Beverage C, except that Comparative Emulsion I' was used instead of Emulsion III.

[0137] The turbidity of Beverage D and Comparative Beverage C' was measured and is shown in Table 5 below.

[0138] Table 5

[0139]

[0140] Examples 7-10: Emulsions with Different Levels of Tween™ 60

[0141] Emulsion III of the present invention was prepared by the same procedure as Emulsion II, except that 3 g (instead of 25 g) of Tween TM 60. The ratio between polyethoxylated sorbitan fatty acid ester Tween™ 60 and lecithin was 1:1, and the ratio between polyethoxylated sorbitan fatty acid ester and fragrance oil was 1:10. The amount of glycerin was increased accordingly to maintain a final product weight of 1000 grams.

[0142] Emulsion IV of the present invention was prepared by the same procedure as Emulsion II, except that 6 g (instead of 25 g) of Tween TM The ratio between polyethoxylated sorbitan fatty acid ester Tween™ 60 and lecithin was 2:1, and the ratio between polyethoxylated sorbitan fatty acid ester and fragrance oil was 1:5. The amount of glycerol was increased accordingly to maintain a final product weight of 1000 grams.

[0143] Emulsion V of the present invention was prepared by the same procedure as Emulsion II, except that 30 g (instead of 25 g) of Tween TM 60. The ratio between polyethoxylated sorbitan fatty acid ester Tween™ 60 and lecithin was 10:1, and the ratio between polyethoxylated sorbitan fatty acid ester and fragrance oil was 1:1. The amount of glycerin was reduced accordingly to maintain a final product weight of 1000 grams.

[0144] Emulsion VI of the present invention was prepared by the same procedure as Emulsion II, except that 60 g (instead of 25 g) of Tween TM The ratio between polyethoxylated sorbitan fatty acid ester Tween™ 60 and lecithin was 20:1, and the ratio between polyethoxylated sorbitan fatty acid ester and fragrance oil was 2:1. The amount of glycerin was reduced accordingly to maintain a final product weight of 1000 grams.

[0145] Examples 11-14: Alcoholic Beverages

[0146] Beverages E, F, G, and H of the present invention were prepared using emulsions III, IV, V, and VI, respectively, following the procedure described above in Example 3, except that different emulsions were used.

[0147] The turbidity of these four beverages was measured. The results are summarized in Table 6 below along with Beverage B described in Example 4 above.

[0148] Table 6

[0149]

[0150] As shown in Table 6, beverages B and EH unexpectedly had turbidity of less than 2 NTU after one day of storage. Note that in these five beverages, the ratio between polyethoxylated sorbitan fatty acid ester and lecithin ranged from 1:1 to 20:1.

[0151] Examples 15-17: Emulsions containing two polyethoxylated sorbitan fatty acid esters

[0152] Emulsion VII of the present invention was prepared by the same procedure as Emulsion II, except that (i) 12.5 g of Tween TM 60 and 12.5 grams of Tween TM 80 instead of 25 grams of Tween TM 60.

[0153] Emulsion VIII of the present invention was prepared by the same procedure as Emulsion II, except that (i) 12.5 g of Tween TM 60 and 12.5 grams of Tween TM 20 instead of 25 grams of Tween TM 60.

[0154] Emulsion IX of the present invention was prepared by the same procedure as Emulsion II, except that (i) 12.5 g of Tween TM 20 and 12.5 grams of Tween TM 80 instead of 25 grams of Tween TM 60 and (ii) the amount of glycerol.

[0155] Examples 18-20: Alcoholic Beverages Prepared from Emulsions VII to IX

[0156] Beverages J, K, and L of the present invention were prepared using emulsions VII, VIII, and IX, respectively, according to the procedure described in Example 4 above. The turbidity of these three beverages was measured. The results are shown in Table 7 below, along with Beverage B.

[0157] Table 7

[0158]

[0159] As shown in Table 7 above, at time 0 and after 1 day, each of the four beverages had a turbidity of less than 2 NTU.

[0160] Examples 21-22: Emulsions with antifoaming agents

[0161] Emulsion X of the present invention was prepared by following the same procedure as Emulsion II, except that 30 grams of a water-dispersible antifoaming agent, HI MAR S-010 FG K (10% silicone emulsion, Hi-Mar Specialty Chemicals, LLC, Milwaukee, Wis., USA), was added to the aqueous phase after high shear mixing but before high pressure homogenization. The amount of glycerin was reduced by 30 grams.

[0162] Emulsion XI of the present invention was prepared by the same procedure as for Emulsion II, except that 5 grams of an oil-soluble antifoaming agent, XIAMETER ACP-1500 (Dow Corning Corporation, Auburn, MI, USA), was added to the fragrance oil phase prior to high shear mixing. The amount of glycerin was reduced by 5 grams. The pre-emulsion was further processed three times in a high pressure homogenizer at 7,000 psi.

[0163] Examples 23-24: Non-alcoholic beverages prepared from emulsions X and XI

[0164] Beverages M and N of the present invention were prepared using emulsions X and XI, respectively, following the same procedure as for Beverage C, except that different emulsions were used. The turbidity of Beverage S and Beverage T was measured and is shown in Table 8 below.

[0165] Table 8

[0166]

[0167] Examples 25 and 26: Stability Examples

[0168] Emulsion XII of the present invention was prepared following the same procedure as Emulsion I, except that (i) 17 g of Tween™ 80 was used instead of 25 g of Tween™ 60, (ii) the amount of glycerol was increased to 250 g, and (iii) the amount of propylene glycol was reduced to 100 g.

[0169] Emulsion XII had a water activity of 0.53 as measured using an AquaLab dew point water activity meter.

[0170] Beverage O of the present invention was prepared according to the same procedure as for Beverage C, except that Emulsion XII was used instead of Emulsion I.

[0171] Comparative emulsion XII was prepared following the same procedure as emulsion I, except that 15 g of sucrose monopalmitate P90 (commercially available from Compass Foods, Singapore) was used instead of Tween™ 60, (ii) the amount of glycerol was increased to 252 g, and (iii) the amount of propylene glycol was reduced to 100 g.

[0172] Comparative Beverage O' was prepared following the same procedure as Beverage C, except that Comparative Emulsion XII was used instead of Emulsion I.

[0173] Beverage O and comparative beverage O' were tasted for stability. The results showed that when stored at 37°C, Beverage O was surprisingly stable for 16 weeks, which is equivalent to 16 months of storage at room temperature. In contrast, comparative beverage O' became unstable after 6 weeks when stored at 37°C.

[0174] Other implementation plans

[0175] All features disclosed in this specification may be combined in any combination. Each feature disclosed in this specification may be replaced by an alternative feature that provides the same, equivalent, or similar purpose. Therefore, unless otherwise expressly stated, each feature disclosed is merely an example of a series of equivalent or similar features.

[0176] In fact, in order to prepare the spice nanoemulsion, those skilled in the art can select the content and ratio, cosolvent of different spices, solvents, polyethoxylated sorbitan fatty acid esters and lecithin and the loading of spices in the beverage. In addition, the technician can also select other auxiliary materials and applicable stabilizing agents.

[0177] From the above description, the technical staff can easily determine the basic characteristics of the present invention, and without departing from its spirit and scope, can make various changes and modifications of the present invention to adapt it to various uses and situations. Therefore, other embodiments are also within the scope of the claims.

Claims

1. A fragrance nanoemulsion comprising a plurality of oil droplets, an aqueous phase, and a surfactant system, wherein the nanoemulsion has a water activity of 0.7 or less and a water content of 25% by weight or less. in, Each of the oil droplets having a droplet size of 0.1 to 500 nm contains fragrance and is dispersed in the aqueous phase, The aqueous phase contains water and a cosolvent, The surfactant system comprises polyethoxylated sorbitan fatty acid ester and lecithin, The polyethoxylated sorbitan fatty acid ester has an HLB of 9 to 20, The lecithin has an HLB of 4 to 16, and The weight ratio of polyethoxylated sorbitan fatty acid ester to fragrance is in the range of 1:15 to 3:1, The cosolvent is a mixture of propylene glycol, glycerol and sorbitol.

2. The fragrance nanoemulsion of claim 1 , wherein the surfactant system is present at a level of 0.1 to 20% and the fragrance is present at a level of 1 to 20%.

3. The fragrance nanoemulsion of claim 1 or 2, wherein the polyethoxylated sorbitan fatty acid ester is polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, or a combination thereof.

4. The fragrance nanoemulsion of any one of claims 1 to 3, wherein the lecithin is natural, de-oiled, fractionated, or enzyme-modified.

5. The fragrance nanoemulsion of any one of claims 1-4, wherein the weight ratio between the polyethoxylated sorbitan fatty acid ester and the lecithin is 30:1 to 1:5, the polyethoxylated sorbitan fatty acid ester is present at a level of 0.05 to 15%, and the lecithin is present at a level of 0.05 to 5%.

6. The fragrance nanoemulsion of any one of claims 1 to 5, wherein the weight ratio between water and the cosolvent is 1:95 to 1:3, or preferably 1:20 to 1:

5.

7. The fragrance nanoemulsion of claim 1 , wherein the propylene glycol is present at a level of 5 to 25%, the glycerin is present at a level of 0.1 to 35%, and the sorbitol is present at a level of 25 to 65%.

8. The fragrance nanoemulsion according to any one of claims 1 to 7, further comprising a defoaming agent.

9. The flavor nanoemulsion of claim 8, wherein the defoaming agent is a silicone emulsion antifoaming agent, a polydimethylsiloxane antifoaming agent, 2-octanol, wax paste, hop lipids, alginate, mineral oil, sorbitan monostearate, or a combination thereof.

10. The fragrance nanoemulsion according to any one of claims 1 to 9, wherein the nanoemulsion contains 20% or less water, and preferably 15% or less water, and has a water activity of 0.65 or less, or preferably 0.6 or less.

11. The flavor nanoemulsion of any one of claims 1-10, wherein each of the oil droplets further comprises an oil-soluble vitamin, an oil-soluble colorant, an antioxidant, a flavor modifier, a mouthfeel modifier, or a combination thereof.

12. The flavor nanoemulsion of claim 11, wherein the taste modifier is an acid masking agent, a cooling agent, a spicy taste, a sweetener, a salty agent, a salivating agent, a substance that causes warming or tingling sensations, or a combination thereof.

13. A liquid beverage or liquid beverage concentrate comprising the flavor nanoemulsion of claim 1, wherein the liquid beverage or liquid beverage concentrate has a turbidity of 10 NTU or less.

14. The liquid beverage or liquid beverage concentrate of claim 13, further comprising alcohol.

15. A method for preparing the nanoemulsion according to claim 1, comprising the steps of: (a) providing an aqueous phase comprising polyethoxylated sorbitan fatty acid ester, water and a cosolvent, (b) providing an oil phase comprising flavoring and lecithin, and (c) emulsifying the oil phase into the aqueous phase to obtain the nanoemulsion, wherein the polyethoxylated sorbitan fatty acid ester has an HLB of 9 to 20, the lecithin has an HLB of 4 to 16, and the weight ratio of the polyethoxylated sorbitan fatty acid ester to the flavor is in the range of 1:15 to 3:1.

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