The technology disclosed in this specification pertains to a method of adsorbing an active ingredient onto free-flowing porous starch granules, to provide free-flowing porous starch granules with the active ingredient adsorbed or plated onto them. The method relates to introducing the active ingredient in an oil-and-liquid emulsion to facilitate its adsorption to the porous starch granules. The adsorbed free- flowing porous starch granules are useful for storing and delivering oil-based ingredients for use in a variety of edible, industrial, and pharmaceutical compositions.

Many compositions have a dry. solid form and are made of dry ingredients, where the addition of a liquid ingredient will destroy the dry, solid form of the composition. One strategy for introducing liquid components to such a dry, solid mixture is to plate the liquid onto free-flowing porous starch granules - the granules adsorb the liquid, but retain a dry, solid, and free-flowing form - thus allowing the incorporation of the liquid without losing the dry, solid form of the composition.

However, there are limitations to this strategy. Not all liquids can be plated successfully. And some liquids may be plated successfully but suffer a decrease in shelf life or some loss or impairment of physical, biological, or chemical activity or property. And even where plating is a suitable method, currently there is typically a limit to the amount of liquid that can be plated onto the porous starch granules; if too much liquid is added, the granules agglomerate into clumps or even into a solid mass. This provides physical constraints on the amount of liquid material that can be thus loaded.

There is a strong demand in the food, beverage, beauty and home care, pharmaceutical, animal feed, and other industries to provide an active ingredient, such as a flavorant, nutrient, or fragrance, in an emulsifying compound and deliver the active ingredient in the form of a free-flowing powder, typically for incorporation into another product for commercial use. Thus, the active ingredient is stored or delivered as a free-flowing powder, which provides reductions in manufacturing, storing, and delivery costs, and protects or extends the performance and shelf-life stability of the active ingredient. However, there is a demand for the delivery of larger amounts of active ingredients in a shelf-stable form.

This specification describes a method of transferring active ingredients onto porous starch granules, by including the active ingredient as part of an oil-and-liquid emulsion for delivery to the porous starch granules, and for protecting the activity of the active ingredients over time. Some methods are performed in the absence of heat, to prevent exposure to an environmental condition that damages or impairs the stability and activity of some active ingredients. This specification also describes free- flowing porous starch granules loaded with active ingredients whose functionality is protected over time, and to uses of the adsorbed porous starch granules in a variety of compositions. This specification also discloses compositions comprising the adsorbed porous starch granules.

Such adsorbed porous starch granules can be used to convert liquid emulsions into easy-to-handle, free flowable powders without the need of spraydrying or freeze-drying steps or equipment, or application of other drying technology, which can reduce the capital expense, maintenance, and energy costs associated with equipment. Such granules also convert liquid compositions into a dry powder form that is easily stored and transported. By plating active ingredients in the presence of an emulsifying agent, amount of active ingredient delivered in increased and the shelf life, stability, and chemical or biological activities of the active ingredients are protected or extended.

BRIEF DESCRIPTION OF THE FIGURES

Figure 1 reports measurements of the mean particle sizes of emulsion compositions made according to the specification.

Figure 2 shows images of starch granules plated with the oil-and-water emulsion composition of Figure 1.

Figure 3 reports measurements of the mean particle sizes of porous starch granules, and of porous starch granules plated with an oil-and-water emulsion, made according to the specification.

Figure 4 reports measurements of the mean particle sizes of an emulsion composition made with a starch blend according to the specification.

Figure 5 shows images of starch particles coated with an emulsion composition.

Figure 6 reports measurements of the mean particle sizes of an emulsion composition made with a starch blend according to the specification. Figure 7 shows images of starch granules coated with an emulsion composition.

Figure 8 reports measurements of the mean particle sizes of porous starch granules, and of porous starch granules plated with an oil-and-water emulsion, made according to the specification.

Figure 9 reports measurements of the amount of oil recovered from different starch granules upon which oil compositions had been loaded, using a variety of methods. The experiments were performed using oil compositions that were prepared fresh or aged prior to use.

Figure 10 reports measurements of sensory evaluations of the oil-loaded starch granule compositions of Figure 9. A sensory panel assessed each sample for the intensity of its overall citrus aroma and the intensity of its oxidized aroma.

Definitions

The subject matter described in this specification can be better understood with reference to the following definitions and other guidance for construing the terms in this specification.

The term "polysaccharide" as used herein refers to starches, gums, dextrins, celluloses, and heteropolysaccharides, and derivatives thereof, hydrolysates thereof, crosslinked products thereof and combinations thereof. Where one polysaccharide is used as a material, another polysaccharide may substitute for it in other embodiments.

Reference to the term “porous starch granule”, used interchangeably with “porous starch particle”, refers to a starch product that has multiple pores or concave portions or depressions on its exterior surface, that increase the surface area when compared to a smooth starch granule of similar size and overall dimension, as show n by scanning electron microscopic techniques. Some indentations are present as dimples or dents on the surface of the granule, which form concave portions at a single location on the granule. Some indentations are present as passageways that traverse the interior of the granule, and connect openings at least two locations on the granule. The pores and passageways are present in a range of sizes and dimensions, to provide a starch granule with an uneven exterior surface.

A porous starch granule is a particulate substance with porous adsorption properties. Porous starch granules absorb wet/liquid substances maintaining their dry substance. Native starch is made of amylopectin and amylose, which together form a densely packed crystalline structure known as a granule. Porous starch particles or granules differ from native starch granules in that chemical or physical treatments of the native starch causes the formation of an increased volume of pores on its surface, giving it a sponge-like structure that creates adsorbancy where typical native nongelatinized starches have little to none. This feature also increases the surface area of a porous starch particle, compared to a native starch particle of the same size, (e.g., powder) while adsorbing the substances. Porous starch granules are generated, for example, when granular starch is modified by enzymatic degradation and/or crosslinking processes. Porous starch granules are also generated by other processes, such processes providing a large specific surface area to the modified starch granules.

A starch product may contain porous starch granules, non-porous starch granules, or a mixture thereof.

Reference in this specification to “free-flowing” starch or other materials refers to dry or solid materials that are amenable to pouring. Free-flowing starches may exhibit an ease of flow that is comparable to a liquid, to move with a liquid-like motion, not to gather in clumped masses.

Reference in this specification to “aqueous component” refers to a component comprising water regardless of its phase (solid, liquid, gaseous, etc.). Aqueous components may comprise other ingredients which are suspended, dispersed, dissolved, or otherwise mixed in the aqueous component. Aqueous components have various pHs.

Reference in this specification to “emulsion composition” refers to a mixture containing at least oil, another liquid, and an emulsifying agent. An “emulsifying agent” is a substance that facilitates the mixture of two or more liquids that are normally immiscible with each other (e.g., oil and water). In some applications, one or more components of the emulsion composition comprise an active ingredient; in some applications, an emulsion composition contains an additional ingredient that contains an active ingredient.

Reference in this specification to “active ingredient” refers to a composition that possesses a physical, chemical, or biological activity. An active ingredient is a composition whose delivery is desired for its ability to cause or enhance any desired effect upon or after delivery as part of another product.

Reference in this specification to “adsorbed starch granule” refers to a porous starch granule to which an emulsion compound has been adsorbed. In some circumstances, the emulsion composition adheres to an outer surface of the starch granule. In some circumstances, the emulsion composition occupies dimples or concave areas on the surface of the starch granules. In some circumstances, the emulsion composition occupies passageways that traverse the interior portion of the granule. An adsorbed starch granule is generated when an emulsion compound is adsorbed onto a porous starch granule. The porous starch granules comprise a plurality of free-flowing particles or granules. After an emulsion compound is adsorbed, the adsorbed starch granules retain their free-flowing particle or granule form.

Reference in this specification to “particle size” refers to the size distribution of particles or granules in a composition. Particle size is measured using laser scattering and may be done using any suitable apparatus. Where an emulsion composition is adsorbed onto porous starch granules, the particle size indicates the amount of oil, water, or other component of the emulsion composition loaded onto the adsorbed starch granules. Particle size also provides a guide as to saturation of the starch granules dunng the plating process, as such particles aggregate and form larger particles. Within this specification particle size is measured using of a Beckman Coulter particle size analyzer, which measures particle size using laser diffraction (ranges from 0.2 pm - 1600 pm). Particle sizes reported in this specification are in microns and refer to the diameter of the referred-to particle or granule in the distribution. Mean particle sizes reported are volume weighted mean particle size sometimes called a volume mean particle sizes or a D4,3 means.

Reference in this specification to “soluble” content means a sample of solids that is dissolvable in solution. Within this specification it measured by reference to the percent of a portion of a sample that has dissolved solution. Most commonly in this specification, soluble refers to the percent of starch that has dissolved in aqueous solution. The soluble content is not intended to be an absolute but is taken relative to other conditions.

Use of “about” to modify a number is meant to include the number recited plus or minus 10%. Where legally permissible recitation of a value in a claim means about the value. Use of about in a claim or in the specification is not intended to limit the full scope of covered equivalents.

Recitation of the indefinite article “a” or the definite article “the” is meant to mean one or more unless the context clearly dictates otherwise. While certain embodiments have been illustrated and described a person with ordinary skill in the art, after reading the foregoing specification, can effect changes, substitutions of equivalents and other types of alterations to the methods, and of the present technology'. Each aspect and embodiment described above can also have included or incorporated therewith such variations or aspects as disclosed regarding any or all the other aspects and embodiments.

The present technology is also not to be limited in terms of the aspects described herein, which are intended as single illustrations of individual aspects of the present technology. Many modifications and variations of this present technology can be made without departing from its spirit and scope, as will be apparent to those skilled in the art. Functionally equivalent methods within the scope of the present technology, in addition to those enumerated herein, will be apparent to those skilled in the art from the foregoing descriptions. Such modifications and variations are intended to fall within the scope of the appended claims. It is to be understood that this present technology is not limited to methods, conjugates, reagents, compounds, compositions, labeled compounds or biological systems, which can, of course, vary. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. It is also to be understood that the terminology used herein is for the purpose of describing aspects only and is not intended to be limiting. Thus, it is intended that the specification be considered as exemplary only with the breadth, scope and spirit of the present technology indicated only by the appended claims, definitions therein and any equivalents thereof. No language in the specification should be construed as indicating any non-claimed element as essential.

The embodiments illustratively described herein may suitably be practiced in the absence of any element or elements, limitation or limitations, not specifically disclosed herein. Thus, for example, the terms “comprising,” “including,” “containing,” etc. shall be read expansively and without limitation. Additionally, the terms and expressions employed herein have been used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the claimed technology. Additionally, the phrase “consisting essentially of’ will be understood to include those elements specifically recited and those additional elements that do not materially affect the basic and novel characteristics of the claimed technology. The phrase “consisting of’ excludes any element not specified.

In addition, where features or aspects of the disclosure are described in terms of Markush groups, those skilled in the art will recognize that the disclosure is also thereby described in terms of any individual member or subgroup of members of the Markush group. Each of the narrower species and subgeneric groupings falling within the generic disclosure also form part of the technology. This includes the generic description of the technology with a proviso or negative limitation removing any subject matter from the genus, regardless of whether the excised material is specifically recited herein.

As will be understood by one skilled in the art, for any and all purposes, particularly in terms of providing a written description, all ranges disclosed herein also encompass any and all possible subranges and combinations of subranges thereof. Any listed range can be easily recognized as sufficiently describing and enabling the same range being broken down into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each range discussed herein can be readily broken down into a lower third, middle third and upper third, etc. As will also be understood by one skilled in the art all language such as “up to,” “at least,” “greater than,” “less than,” and the like, include the number recited and refer to ranges which can be subsequently broken down into subranges as discussed above. Finally, as will be understood by one skilled in the art, a range includes each individual member, and each separate value is incorporated into the specification as if it were individually recited herein.

The technology' disclosed in this specification can be better understood with reference to the following aspects, which are not intended to limit the full scope of the described technology .

Tn one aspect, the technology disclosed in this specification pertains to a free-flowing, starch granule product made of a plurality of free-flowing porous starch granules having adsorbed to them an emulsion compound containing an active ingredient. In addition to the active ingredient, the emulsion compound comprises an oil-based component, an aqueous component, and an emulsifying agent which is believed to facilitate the delivery' of the active ingredient to the porous starch granules such that the adsorbed granules retain their free-flowing, powder-like form (compared to agglomerating into a solid or cohesive mass). Thus, the resulting adsorbed porous starch granules retain their state as free-flowing solid particles, but with a desired active ingredient adsorbed to individual particles.

In another aspect, this specification describes methods that employ to deliver active ingredients onto porous starch granules, through the use of an emulsion compound, to obtain the plurality of free-flowing porous starch granules having adsorbed to them an emulsion compound containing an active ingredient.

In some embodiments, the active ingredient is a lipid-based, or fat-based, or oil-based component. In other embodiments, the active ingredient is an aqueous component. In some embodiments, the active ingredient is a solids-based component. Any such ingredient may be delivered in an active state or may require certain treatment (e.g., by heat, enzymatic, or chemical treatment) before being converted to an active form. Typically, the emulsion compound comprises an oil-based component, an aqueous component, and an emulsifying agent. In any embodiment, at least one of these components is or comprises an active ingredient. In any embodiment, none of these components is or comprises an active ingredient, and the active ingredient is present as an additional ingredient or ingredients. In some embodiments, the oil-based component is the active ingredient. In some embodiments, the oil-based component further contains the active ingredient.

Within this specification, active ingredient is used broadly and includes pharmaceutically active ingredients, or nutritional ingredients, or non-nutritive functional ingredients such as scents or flavors, and mixtures thereof. Active ingredient also encompasses substances that possess any desired physical, chemical, or biological activity. Active ingredient also encompasses compositions whose delivery is desired for its ability to cause or enhance any desired effect when delivered as part of another product. In any embodiment, an active ingredient is present as a single ingredient or as combination of ingredients.

In any embodiment, desired activities conferred by an active ingredient includes various activities that prolong or extend the shelf-life, the time frame over which a product can be relied upon to retain its quality characteristics, of various products. Desired activities conferred by an active ingredient includes various activities that prolong or extend the shelf-life of various products by controlling or influencing the effects of extrinsic factors such as, but not limited to, temperature, time, relative humidity, presence of gases, physical stress, and other environmental parameters. Desired activities conferred by an active ingredient includes various activities that prolong or extend the shelf-life of various products by controlling or influencing the effects of intrinsic factors such as, but not limited to, pH, moisture content, water activity, nutrient content, antimicrobial agents, biological structures and oxidation/reduction potential. Desired activities conferred by an active ingredient includes activities that halt or minimize physical, chemical, biological, and microbial deterioration of various products. As an example, an active ingredient with plasticizing properties may be delivered via an embodiment of this invention.

In any embodiment, the active ingredient is delivered to porous starch granules in the presence of an emulsion compound. Typically, the emulsion compound comprises an oil-based component, an aqueous component, and an emulsifying agent. Emulsifying agents are known to stabilize a liquid-oil interface, by a variety of mechanism, such as by maintaining small oil droplet size within the aqueous portion, or by the emulsifying agent providing a coating around oil droplets to provide encapsulated active ingredients.

Within this specification, the emulsion compound comprises an emulsifying agent that comprises a starch product. Such starch products encompass native starches and modified starches. It is well-known that starches can be modified by a variety of processes, including but not limited to physical, mechanical, pressure, temperature, chemical, and enzymatic processes, and combinations thereof. In any embodiment, the starch product is physically modified by physical factors including, but not limited to, physical factors such as milling, grinding, micronization, shearing, moisture, temperature, thermal heating, non-thermal heating, moisture treatment, pressure, pH, radiation, pulse-electric field, and ultrasonic waves. The starch product may also be subjected to partial or complete gelatinization prior to use, or to processes such as agglomeration or treatments with salts.

In any embodiment, such starch product is modified by chemical processes including, but not limited to, oxidation, hydrolysis, dextrinization, etherification, hydroxylpropylation, esterification, acetylation, cationization, cross-linking, and octenylsuccinic anhydride modification. In any embodiment, the modified starch product is generated by treating starches by more than one modification process. This specification discloses an emulsifying agent that is a modified starch. In any embodiment, this specification discloses an encapsulating composition wherein the emulsifier is a succinate modified starch, for example an octenylsuccinate modified starch. In some preferred embodiments, the starch product is an octenylsuccinic anhydride (“OSA”) modified starch. Examples of such OSA starches include, but are not limited to, PURITY GUM® Ultra and PURITY GUM® 2000 are OSA starch emulsifiers (Ingredion Inc.).

In some embodiments, the starch product is a starch that is soluble in water or other liquid. In some preferred embodiments, the starch product is a modified starch that is soluble in water or other liquid or solvent. In any embodiment, the starch product is chosen from being: soluble, partially soluble, or insoluble in water or liquid or solvent. In any embodiment, the emulsifying agent comprises a second starch product. The second starch product can be a native or modified starch. In any embodiment, the second starch product is a soluble starch.

Within the specification, the plurality of free-flowing emulsion-adsorbed starch granules possess an extended or improved shelf-life, when compared to substantially similar emulsion-free adsorbed starch granules made in substantially the same way, except for the absence of an emulsion compound during the adsorption of the active ingredient. A desired active ingredient could be loaded onto both sets of adsorbed starch granules, but the presence of the emulsion compound during the adsorption process is believed to extend or lengthen the half-life of the emulsion- adsorbed starch granules compared to the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is about 10%, about 25%, about 50%, about 100%, about 200%, or about 400% longer than that of the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is at least about 10%, about 25%, about 50%, about 100%, about 200%, about 400% greater than that of the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is at least about 25% or about 50% greater than that of the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion- adsorbed starch granules possess a shelf life that is at least about 100% or about 200% greater than that of the substantially similar emulsion-free adsorbed starch granules. Within the specification, the plurality of free-flowing emulsion-adsorbed starch granules possess an extended or improved active ingredient activity, when compared to substantially similar emulsion-free adsorbed starch granules made in substantially the same way, except for the absence of an emulsion compound during the adsorption of the active ingredient. A desired active ingredient could be loaded onto both sets of adsorbed starch granules, but the presence of the emulsion compound during the adsorption process is believed to extend or lengthen the activity of the active ingredient adsorbed onto of the emulsion-adsorbed starch granules compared to the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the active ingredient on the emulsion-adsorbed starch granules possesses a shelf life that is about 10%, about 25%, about 50%, about 100%, about 200%, or about 400% longer than that of the active ingredient adsorbed on the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion- adsorbed starch granules possess an active ingredient activity that is at least about 10%, about 25%, about 50%, about 100%, about 200%, about 400% greater than that in the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess an active ingredient activity that is at least about 25% or about 50% greater than that on the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion- adsorbed starch granules possess an active ingredient activity that is at least about 100% or about 200% greater than that on the substantially similar emulsion-free adsorbed starch granules.

Within this specification, the emulsion compound comprises an emulsifying agent that is not a starch product. Emulsifying agents commonly used in foods include, but are not limited to, gum acacia/gum arabic, agar, albumin, alginates, casein, egg yolk, glycerol monostearate, gums, Irish moss, lecithin, mono- and diglycerides, polysorbates, carrageenan, guar gum and canola oil. Emulsifying agents commonly used in pharmaceutical products include, but are not limited to, ethylene glycol stearates, lecithins, polysorbates, wax, lonalin alcohols, mono- and diglycerides, sodium lauryl sulfate, and stearic acid. Other commonly used emulsifying agents include, but are not limited to, polymers (Spans and Tweens), sodium lauryl sulfate, sodium dioctyl sulfosuccinate, and tragacanthins. Emulsifying agents also include gums, including gums and gum like materials and include gelling starches, gum acacia/gum Arabic, xanthan gum, tara gum, konjac, carrageenan, locust bean gum, gellan gum, guar gum, and mixtures thereof. Additional examples of emulsifying agents include but not limited to quillaja extracts.

Within this specification, the emulsion compound comprises an oil-based component, an aqueous component, and an emulsifying agent. Non-limiting examples of aqueous components are water (whether in liquid form, as steam, or as ice), milk, juice, puree, syrup, acidic liquids like vinegar, alkaline liquids, and similar ingredients. A preferred group of aqueous components encompass food-grade, cosmetic-grade, industrial — grade, or pharmaceutical grade liquids. A preferred aqueous component is water. In any embodiment, an aqueous component is present as a single aqueous component or as combination of aqueous components.

Non-limiting examples of oil-based component include soybean oil, sunflower oil, com oil, cottonseed oil, peanut oil, olive oil, palm oil, orange oil, lemon oil, coconut oil, almond oil, walnut oil, jojoba oil, avocado oil, lavender oil, apricot oil, cocoa oil, bitter gourd oil, flaxseed oil, acai oil, and other plant-based oils. Other examples of oil include mineral oil. Other examples of oil include extracts of interest such as cannabis extracts (cannabinoids (CBD) and tetrahydrocannabmoid (THC)). Any embodiment includes marine or fish-based oils, such as but not limited to omega- 3 fatty acids. Any embodiment includes fatty acids, preferably polyunsaturated fatty acids. In any embodiment, an oil-based component is present as a single oil or as combination of oils. In some embodiments, food grade or pharmaceutical grade oils are preferred. In some embodiments, the oil-based component is chosen from orange oil and medium chain triglycerides (MCT). In some embodiments, the oil-based component is orange oil.

In any embodiment described in this specification, an emulsion compound comprises an oil-based ingredient. In any embodiment described in this specification, the emulsion compound further comprises the oil-based ingredient in an amount of greater than about 1% by weight of the composition, greater than about 5% by weight of the composition, or greater than about 10% by weight of the composition. In any embodiment described in this specification, the emulsion compound further comprises an oil-based ingredient in an amount by weight of the emulsion compound, chosen from: about 1% to about 60%, about 1% to about 50%, about 1% to about 40%, and about 1% to about 30%. In any embodiment described in this specification, the emulsion compound further comprises an oil-based ingredient in an amount by weight of the emulsion compound, chosen from: about 10% to about 60%, about 10% to about 50%, about 10% to about 40%, and about 10% to about 30%. In any embodiment described in this specification, the emulsion compound further comprises an oil-based ingredient in an amount by weight of the emulsion compound, chosen from: about 1% to about 60%, and about 10% to about 60%.

In any embodiment, in the emulsion compound, the ratio of emulsify ing agent to oil phase is chosen from the following: about 1:6, about 1:5, about 1:4, about 1 :3, about 1 :2, about 1 :1, and about 1:0.5. In any embodiment, the emulsion compound has an oihliquid between 1 :5 and 1:0.5. In any embodiment, the emulsion compound has an oihliquid between 1:3 and 1: 1. In any embodiment, the emulsion compound has an oilliquid ratio is about 1: 1.

In any embodiment, in the emulsion compound, the ratio of oil phase to emulsifying agent is chosen from the following: about 1:6, about 1 :5, about 1 :4, about 1 :3, about 1 :2, about 1 :1, and about 1:0.5. In any embodiment, the emulsion compound has a liquid: oil between 1:5 and 1:0.5. In any embodiment, the emulsion compound has a liquid: oil between 1:3 and 1 : 1. In any embodiment, the emulsion compound has a liquid: oil ratio is about 1 :1.

In any embodiment described in this specification, the emulsifying agent is present as a certain amount relative to the aqueous component. In any embodiment described in this specification, the emulsifying agent further comprises the aqueous component in an amount by weight of the emulsifying agent, chosen from: about 1% to about 50%, about 1% to about 40%, and about 1% to about 30%. In any embodiment described in this specification, the emulsifying agent further comprises the aqueous component in an amount by weight of the emulsifying agent, chosen from: about 10% to about 50%, about 10% to about 40%, and about 10% to about 30%. In any embodiment described in this specification, the emulsifying agent further comprises the aqueous component in an amount by weight of the emulsion compound, chosen from: about 1% to about 50%, and about 10% to about 50%. In any embodiment described in this specification, the emulsifying agent is present as a certain amount relative to the oil-based component. In any embodiment described in this specification, the emulsifying agent further comprises the oil-based component in an amount by weight of the emulsifying agent, chosen from: about 1 % to about 50%, about 1% to about 40%, and about 1% to about 30%. In any embodiment described in this specification, the emulsifying agent further comprises the oil-based component in an amount by weight of the emulsifying agent, chosen from: about 10% to about 50%, about 10% to about 40%, and about 10% to about 30%. In any embodiment described in this specification, the emulsifying agent further comprises the oil-based component in an amount by weight of the emulsion compound, chosen from: about 1% to about 50%, and about 10% to about 50%.

Emulsion compounds may be prepared using any method of emulsification known in the art. The mixed ingredients are then homogenized using means known in the art to achieve the desired small mean particle size and/or distribution. Emulsion compounds described in this specification also include ingredients added to change texture, viscosity , or other organoleptic property of the emulsion compound. Such ingredients include hydrocolloids (gums and gum-like substances) modified fibers such as carboxymethyl cellulose or hydroxypropyl methyl cellulose; unmodified starches; and physically and chemically modified starches (including but not limited to thermally inhibited starches and chemically crosslinked starches).

In any embodiment, the emulsion compound contains other optional ingredients or components such as, for example, salts, buffering agents, humectants, surfactants, colorants, flavorants, sweeteners, and the like. In one aspect, the continuous phase contains a preservative and in another the preservative is sodium benzoate.

In any embodiment, buffering agents include, but are not limited to sodium benzoate, sodium citrate, potassium citrate, sodium phosphate dibasic, sodium acetate, and citric acid. In any embodiment, the buffering agents include, but are not limited to sodium benzoate and citric acid. These optional components are typically added in minor amounts, particularly less than about 10 dry weight % of the emulsion compound. More preferably, less than about 5 dry weight % of the composition of the optional components are used in the emulsion compound. In any embodiment, maltodextrins provide low molecular weight components with emulsifying properties. Maltodextrin can also provide desirable viscosity and texture, as well as act as a preservative that extends the shelf like of certain packaged foods. Maltodextrins can minimize oil loss from emulsifying compounds, and provide oxidation resistance to the products containing emulsion compounds. In some applications, however, maltodextrins are undesirable.

In any embodiment, a buffering step includes a suitable food grade buffer. In any embodiment described in this specification, a food grade buffering agent useful for making a thermally inhibited starch is a conjugate acid, or salt of an organic acid. In at least some embodiments the buffer is a sodium buffer, a carbonate buffer or a citrate buffer. In some embodiments a food grade buffer is sodium benzoate and/or citric acid. In any embodiment, the emulsion compound contains food grade components such as, for example, sugar alcohols or other sugar substitutes, pH agents, salinity agents, colorants and thickeners.

Aspects of the invention include a free-flowing, starch granule product made of a plurality of free-flowing porous starch granules having adsorbed to an active ingredient, as well as a method of making such product through the use of an emulsion compound.

In any embodiment, the porous starch particles are starch particles modified by any number of processes which increase the particles’ surface area, porosity, and ability to absorb wet/liquid or dry/solid substances, maintaining its dry' substance form. Porous starch particles or granules are modified to make it porous, having surface area that is larger than a modified version. Porous starch possesses the ability to adsorb solid or liquid materials; in some cases, adsorbing a liquid composition to provide a dry or solid carrier vehicle for transport and delivery of the liquid composition. More generally, in the present invention, the porous starch may also be used as a carrier, microencapsulation-aid, or drying-aid such as freeze-drying aid or spray-drying aid, in the preparation of a flavor powder. The starches used as sources for providing porous starches are cheap, plentiful, and can be derived from a variety of local plant sources. Such starches are natural, biodegradable, safe to handle, and nontoxic. Such porous starch granules are also suitable candidates for clean-label applications, where products are made in the absence of certain chemicals or pH- altering agents. A variety of processes are used for making starch granules porous. These processes can be easily modified to produce porous starch granules of desired size and porosity. For example, manufacturing processes can be altered to regulate the diameter, pore depth, and specific surface area of the porous starch granules, and the manufacturing processes can be manipulated to determine the number and size of pores, pore depth, and surface area, to modify the porous starch particles to accommodate adsorption of different substances. Porous starch is used as an adsorbent in many applications for industries such as food and beverage, health, wellbeing, cosmetics, agriculture, animal feed, industrial applications, and the like.

In any embodiment, a porous starch particle is used to adsorb oil-containing (or active-ingredient-containing) compounds. In any embodiment, a non-porous starch particle is used to adsorb oil-containing (or active-ingredient-containing) compounds. In any embodiment, a mixture or blend of porous and non-porous starch particles is used to adsorb oil-containing (or active-ingredient-containing) compounds.

In any embodiment the plurality of porous starch granules is chosen from porous starch granules, agglomerated starch granules, and fractured starch granules. In any embodiment the plurality of porous starch granules is made via enzymatic treatment of porous starch granules.

In any embodiment, the starch product is obtained from cereal, tubers, roots, legumes and fruits. In any embodiment, native starch is obtained from wheat, waxy wheat, maize, waxy maize, rice, waxy rice, tapioca, waxy tapioca, potato, waxy potato, sweet potato, waxy sweet potato, pea, mung bean, millet, sago, sorghum, quinoa, arrowroot, amaranth, lotus root and buckwheat by a variety of processes. The source can be any variety, including without limitation, high amylose sources, low amylose (waxy) sources, and mixtures thereof.

In any embodiment, the starch product is obtained from is or contains wheat starch, waxy wheat starch, maize starch, waxy maize starch, rice starch, waxy rice starch, tapioca starch, waxy tapioca starch, potato starch, waxy potato starch, sweet potato starch, waxy sweet potato starch, pea starch, mung bean starch, millet starch, sago starch, sorghum starch, quinoa starch, arrowroot starch, amaranth starch, lotus root starch, buckwheat starch, and mixtures thereof. The starch product is obtained from waxy starch sources, non-waxy starch sources, and mixtures thereof. In any embodiment, the starch product is sourced from, but not limited to, plants, including wild-type plants and genetically altered plants, and plants altered by other plant-breeding techniques. In any embodiment, microbially-generated, microbially-engineered, or microbially-sourced starch is contemplated as a source of starch products.

In any embodiment, the starch product is selected from wheat starch, waxy wheat starch, maize starch, waxy maize starch, rice starch, waxy rice starch, tapioca starch, waxy tapioca starch, potato starch, waxy potato starch, sweet potato starch, waxy sweet potato starch, pea starch, mung bean starch, millet starch, sago starch, sorghum starch, quinoa starch, arrowroot starch, amaranth starch, lotus root starch, buckwheat starch, and mixtures thereof. The starch product is selected from waxy starch sources, non-waxy starch sources, and mixtures thereof.

In a preferred embodiment of the present invention, the starch product is selected from the group consisting of waxy wheat starch, waxy maize starch, rice starch, waxy rice starch, waxy potato starch, waxy tapioca starch and mixtures thereof, preferably waxy potato starch and waxy rice starch.

In any embodiment, the porous starch granules are produced through an enzyme hydrolysis of native starch granules with one or more amylolytic enzymes, such as alpha-amylase, beta-amylase, and amyloglucosidase, preferably at temperatures below that required for the gelatinization temperature of the starch. In any embodiment, the porous starch granules are produced by spray-drying modified starch particles into agglomerated starch granules. One such example of a porous starch is N-ZORBIT® 2144 plating agent (Ingredion Inc.).

In any embodiment of a starch granule described in this specification, the porous starch granules are provided as having diameters that fall into mean particle ranges that is generally defined as “fine” (mean particle diameter between about 0.5-5 microns); “medium” (mean particle diameter between about 50-100 microns); or “coarse” (mean particle diameter between about 150-800 microns). In any embodiment, the porous starch granules are provided in as having a mean particle range that is described as “nano” sized (mean particle diameter between about 1-1000 nanometers). In any embodiment of a pre-emulsion composition described in this specification, the pre-emulsion composition is provided as particles having diameters that fall into mean particle ranges that is defined as “fine” (mean particle diameter between about 0.5-5 microns); “medium” (mean particle diameter between about 50- 100 microns); or “coarse” (mean particle diameter between about 150-800 microns). In any embodiment, the porous starch granules are provided in as having a mean particle range that is described as “nano” sized (mean particle diameter between about 1-1000 nanometers).

In any embodiment of an adsorbed starch granule described in this specification, the adsorbed starch granules are provided as having diameters that fall into mean particle ranges that is defined as “fine” (mean particle diameter between about 0.5-5 microns); “medium” (mean particle diameter between about 50-100 microns); or “coarse” (mean particle diameter between about 150-800 microns). In any embodiment, the adsorbed starch granules are provided in as having a mean particle range that is described as “nano” sized (mean particle diameter between about 1-1000 nanometers). Similarly, untreated porous starch granules have mean particles sizes in the same or similar ranges.

In any embodiment, the starch particles are provided as having a mean particle size chosen from: between about 0.1 microns and 200 microns, preferably between about 0.5 microns and 100 microns, and more preferably between about 1 micron and 20 microns. In any embodiment, the starch particles are provided as having a mean particle size chosen from: between about 50 microns and 200 microns; and between about 50 microns and 100 microns.

In any embodiment, the particle diameter is measured by laser diffraction particle sizer (Beckman Coulter LS 13320).

In any embodiment, clean label versions of the starch are provided. Such versions are generated in the absence of nonneutral pHs (e g., alkaline pH) or alcohols, using nonneutral solutions only as needed to accommodate the pHs needed for enzyme hydrolysis or to deactivate enzymes.

In any embodiment, the porous starch particles have a porous structure on their exterior surfaces, which in some cases extend inside the granules in a variety of conformations. The porous starch particles have a large number of pores of vary ing sizes, some of which may or may not be connected to the body of an individual porous starch particle though internal passageways or channels. In any embodiment, the porous starch particles possess a surface topography that includes indentations, dimples, or dents on the surface of the granule, which form concave portions at a single location on the granule. In any embodiment, the porous starch particles possess a surface topography that includes passageways that traverse the interior of the granule, and connect openings at least two locations on the granule. In any embodiment, the porous starch particles possess dimples and passageways. In any embodiment the plurality of porous starch granules is made via enzymatic treatment of porous starch granules.

Within this specification, methods are provided for adsorbing an emulsion compound onto free-flowing starch granules, the emulsion compound containing an active ingredient, in order to provide a plurality of adsorbed starch granules containing the active ingredient that retains a flowable form. In any embodiment, the starch granules are porous starch granules.

In any method, a porous starch particle is used to adsorb oil-containing (or active-ingredient-containing) compounds. In any embodiment, a non-porous starch particle is used to adsorb oil-containing (or active-ingredient-containing) compounds. In any embodiment, a mixture or blend of porous and non-porous starch particles is used to adsorb oil-containing (or active-ingredient-containing) compounds.

In any embodiment, a certain amount of emulsion compound is applied to a certain amount of free-flowing starch granules. In any further embodiment, the ratio of emulsion compound: plurality of adsorbed starch granules is chosen from: about 1 :6, about 1:5, about 1:4, about 1 :3, about 1:2, about 1: 1, and about 0.5: 1. In any embodiment, the ratio of emulsion compound: plurality of adsorbed starch granules is chosen from: about 1:6, about 1:5, about 1:4, and about 1 :3. In any embodiment, the ratio of emulsion compound: plurality of adsorbed starch granules is between about 1 : 1 and 1:5.

In any embodiment of an emulsion compound described in this specification, the emulsion compound is provided as particles having diameters that fall into mean particle ranges that is chosen from: between about 1-1000 microns; between about 100-1000 microns; between about 150-800 microns; between about 15-100 microns; between about 0.5-5 microns; and between about 1-1000 nanometers. In any embodiment, the emulsion compound has a mean particle size chosen from: between about 1-1000 microns; between about 100-1000 microns; between about 150-800 microns; between about 15-100 microns; between about 0.5-5 microns. In any embodiment, the emulsion compound has a mean particle size chosen from: between about 1-1000 microns; between about 100-1000 microns; and between about 150-800 microns. In any embodiment, the emulsion compound has a mean particle size between about 1-1000 microns. In any embodiment, the emulsion compound has a mean particle size between about 150-800 microns. In any embodiment, the emulsion compound has a mean particle size chosen from: between about 0.1-5 microns; between about 0.1-1 microns; and between about 0.5-1 microns. In any embodiment, the emulsion compound has a mean particle size chosen between about between about 0.5-5 microns.

In any embodiment of an adsorbed starch granule described in this specification, the adsorbed starch granule is provided as particles having diameters that fall into mean particle ranges that is chosen from: between about 1-1000 microns; between about 100-1000 microns; between about 150-800 microns; between about 15-100 microns; between about 0.5-5 microns; and between about 1-1000 nanometers. In any embodiment, the adsorbed starch granules have a mean particle size chosen from: between about 1-1000 microns; between about 100-1000 microns; between about 150-800 microns; between about 15-100 microns; between about 0.5-5 microns. In any embodiment, the adsorbed starch granules have a mean particle size chosen from: between about 1-1000 microns; between about 100-1000 microns; and between about 150-800 microns. In any embodiment, the adsorbed starch granules have a mean particle size between about 1-1000 microns. In any embodiment, the adsorbed starch granules have a mean particle size between about 150-800 microns.

In any embodiment, the starch granule is a micronized starch with an average particle size of less than 5 pm. In any embodiment, the starch granule possesses a nominal diameter of from nanometers to micrometers on to which is adsorbed at least active agent, preferably where the active agent contains an oil compound.

Within this specification, methods are provided for adsorbing an emulsion compound onto free-flowing starch granules. In any embodiment, the oil-based component is homogenized before it is added to the emulsion compound. In any embodiment, homogenization is achieved by any suitable means. As a non-limiting example, the homogenization force is applied with a high-pressure-homogenizer, where at least one stage of force is applied to the oil-based component. In preferred embodiments, at least two stages of force are applied to the oil-based component; in such embodiments, the initial homogenization is done at between about 1000-7000 psi, and the subsequent homogenization is done at between about 100-1000 psi. In any further embodiment, the initial homogenization is done at between about 4000- 5000 psi, and the subsequent homogenization is done at between about 100-1000 psi. In any further embodiment, the initial homogenization is done at between about 4500 psi, and the subsequent homogenization is done at between about 500 psi. In any embodiment, a high-shear mixer or other similar equipment is used to prepare the oilbased component before its addition to the emulsion compound.

In any embodiment, the methods are performed in the absence of heat- or cold-based temperatures (as excessive temperatures provide an environment that damages or impairs the stability and activity of some active ingredients). In any embodiment, the methods are performed in the presence of heat, as some active ingredients as heat or high temperatures affects some active ingredients to a small degree or not at all. In any embodiment, methods are performed in the presence of heat, such as spray-drying processes. In some embodiments, a spray-drying step is included; in other embodiments, a spray -drying step is excluded.

Aspects of the invention include a free-flowing, starch granule product made of a plurality of free-flowing starch granules having adsorbed to an active ingredient, made by any of the method of making such product disclosed herein. Aspects of the invention include a free-flowing, starch granule product made of a plurality of free- flowing porous starch granules having adsorbed to an active ingredient, made by any of the method of making such product disclosed herein.

Other aspects of the invention include the use of the free-flowing, starch granule product to deliver an active ingredient to an oil-and-liquid emulsion to a composition. In any embodiment, the oil-and-liquid emulsion comprises a second active ingredient. Within the specification, the plurality of free-flowing adsorbed starch granules has the emulsion compound adsorbed to them. In any embodiment described in this specification, the emulsion compound is present as a certain amount relative to the plurality of free-flowing adsorbed starch granules. In any embodiment described in this specification, the emulsion compound further comprises a portion of the plurality of free-flowing adsorbed starch granules, chosen from: about 1% to about 50%, about 1% to about 40%, and about 1% to about 30%. In any embodiment described in this specification, the emulsion compound further comprises the plurality of free-flowing adsorbed starch granules in an amount by weight of the emulsion compound chosen from: about 1% to about 50%, about 1% to about 40%, and about 1% to about 30%. In any embodiment described in this specification, the emulsion compound further comprises the plurality of free-flowing adsorbed starch granules in an amount by weight of the emulsion compound chosen from: about 10% to about 50%, about 10% to about 40%, and about 10% to about 30%. In any embodiment described in this specification, the emulsion compound further comprises the plurality of free-flowing adsorbed starch granules in an amount by weight of the emulsion compound chosen from: about 1% to about 45%, and about 1% to about 45%.

Within the specification, the plurality of free-flowing adsorbed starch granules has the emulsion compound adsorbed to them. In any embodiment described in this specification, the emulsion compound present contains oil and liquid, present in a certain ratio.

In any embodiment, in the emulsion compound, the ratio of emulsifying agent to oil phase is chosen from the following: about 1:6, about 1:5, about 1:4, about 1 :3, about 1 :2, about 1 :1, and about 1:0.5. In any embodiment, the emulsion compound has an ©illiquid between 1 :5 and 1:0.5. In any embodiment, the emulsion compound has an oihliquid between 1:3 and 1: 1. In any embodiment, the emulsion compound has an oilliquid ratio is about 1 : 1. In any embodiment, the emulsion compound has an oil: liquid ratio between about 1:1 and 1:5.

In any embodiment, in the emulsion compound, the ratio of oil phase to emulsifying agent is chosen from the following: about 1:6, about 1 :5, about 1 :4, about 1 :3, about 1 :2, about 1 :1, and about 1:0.5. In any embodiment, the emulsion compound has a liquid: oil between 1:5 and 1:0.5. In any embodiment, the emulsion compound has a liquid: oil between 1 :3 and 1 : 1. In any embodiment, the emulsion compound has a liquid: oil ratio is about 1: 1. In any embodiment, the emulsion compound has a liquid: oil ratio between about 1: 1 and 1:5.

Within the specification, the plurality of free-flowing adsorbed starch granules includes an emulsifying agent that comprises a starch product. In any embodiment, such starch product is modified by chemical processes including, but not limited to, oxidation, hydrolysis, dextrinization, etherification, hydroxylpropylation, esterification, acetylation, cationization, cross-linking, and octenylsuccinic anhydride modification. In any embodiment, the modified starch product is generated by treating starches by more than one modification process. This specification discloses an emulsifying agent that is a modified starch. In any embodiment, this specification discloses an encapsulating composition wherein the emulsifier is a succinate modified starch, for example an octenylsuccinate modified starch. In some preferred embodiments, the starch product is an octenylsuccinic anhydnde (“OSA”) modified starch. Examples of such OSA starches include, but are not limited to, PURITY GUM® Ultra high-performance emulsifier (Ingredion Inc.).

In some embodiments, the starch product is a starch that is soluble in water or other liquid. In some preferred embodiments, the starch product is a modified starch that is soluble in water or other liquid.

In any embodiment, the emulsifying agent comprises a second starch product. The second starch product can be a native or modified starch. In any embodiment, the second starch product is a soluble starch. In any embodiment, the emulsifying agent comprises a starch or starch blend suitable for delivering or making emulsions. In any embodiment, the emulsifying agent comprises a second starch product. The second starch product can be a native or modified starch. In any embodiment, the second starch product is a soluble starch.

In any embodiment, the emulsifying agent is chosen from being: soluble, partially soluble, or insoluble in water or liquid or solvent.

Within the specification, the plurality of free-flowing emulsion-adsorbed starch granules possess an extended or improved shelf-life, when compared to substantially similar emulsion-free adsorbed starch granules made in substantially the same way, except for the absence of an emulsion compound during the adsorption of the active ingredient. A desired active ingredient could be loaded onto both sets of adsorbed starch granules, but the presence of the emulsion compound during the adsorption process is believed to extend or lengthen the half-life of the emulsion- adsorbed starch granules compared to the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is about 10% longer, about 25% longer, about 50% longer, about 100% longer, about 200% longer, or about 400% longer than that of the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is at least about 10% greater, about 25% greater, about 50% greater, about 100% greater, about 200% greater, about 400% greater than that of the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is at least about 25% greater or about 50% greater than that of the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess a shelf life that is at least about 100% or about 200% greater than that of the substantially similar emulsion-free adsorbed starch granules.

Within the specification, the plurality of free-flowing emulsion-adsorbed starch granules possess an extended or improved active ingredient activity, when compared to substantially similar emulsion-free adsorbed starch granules made in substantially the same way, except for the absence of an emulsion compound during the adsorption of the active ingredient. A desired active ingredient could be loaded onto both sets of adsorbed starch granules, but the presence of the emulsion compound during the adsorption process is believed to extend or lengthen the activity of the active ingredient adsorbed onto of the emulsion-adsorbed starch granules compared to the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the active ingredient on the emulsion-adsorbed starch granules possesses a shelf life that is about 10%, about 25%, about 50%, about 100%, about 200%, or about 400% longer than that of the active ingredient adsorbed on the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion- adsorbed starch granules possess an active ingredient activity that is at least about 10%, about 25%, about 50%, about 100%, about 200%, about 400% greater than that in the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion-adsorbed starch granules possess an active ingredient activity that is at least about 25% or about 50% greater than that on the substantially similar emulsion-free adsorbed starch granules. In any embodiment, the emulsion- adsorbed starch granules possess an active ingredient activity that is at least about 100% or about 200% greater than that on the substantially similar emulsion-free adsorbed starch granules.

Tn any embodiment, the plurality of free-flowing emulsion-adsorbed starch granules are generated using clean label methods. In any embodiment, the plurality of free-flowing emulsion-adsorbed starch granules are generated without applying heat. In any embodiment, the plurality of free-flowing emulsion-adsorbed starch granules are generated without using spray-drying processes.

In any embodiment, the emulsion compound has a mean particle size chosen from: between about 0.1 and about 50 microns; between about 0.1 and about 10 microns; and between about 0.1 and about 5 microns. In any embodiment, the emulsion compound has a mean particle size chosen from: between about 0.5 and about 50 microns; between about 0.5 and about 10 microns; and between about 0.5 and about 5 microns. In any embodiment, the emulsion compound has a mean particle size between about 0.5 and about 50 microns. Aspects of the invention include a composition comprising a free-flowing, starch granule products made of a plurality of free-flowing porous starch granules having adsorbed to an active ingredient, as is described herein. Aspects of the invention include a composition comprising a free-flowing, starch granule products made of a plurality of free-flowing porous starch granules having adsorbed to an active ingredient, as is described herein.

Within the specification, composition containing the plurality of free- flowing emulsion-adsorbed starch granules possess an extended or improved shelflife, when compared to substantially similar composition containing emulsion-free adsorbed starch granules made in substantially the same way, except for the absence of an emulsion compound during the adsorption of the active ingredient. In any embodiment, the composition possesses a shelf life that is about 10%, about 25%, about 50%, about 100%, about 200%, or about 400% longer than that of a composition having substantially similar emulsion-free adsorbed starch granules. In any embodiment, the composition possesses a shelf life that is at least about 10%, about 25%, about 50%, about 100%, about 200%, about 400% greater than that of the substantially similar composition having substantially similar emulsion-free adsorbed starch granules. In any embodiment, the composition possesses a shelf life that is at least about 25% or about 50% greater than that of the composition having substantially similar emulsion-free adsorbed starch granules. In any embodiment, the composition possesses a shelf life that is at least about 100% or about 200% greater than that of the composition having substantially similar emulsion-free adsorbed starch granules.

Within the specification, the plurality of free-flowing emulsion-adsorbed starch granules possess an extended or improved active ingredient activity, when compared to substantially similar emulsion-free adsorbed starch granules made in substantially the same way, except for the absence of an emulsion compound during the adsorption of the active ingredient. In any embodiment, the active ingredient in the composition possesses a shelf life that is about 10%, about 25%, about 50%, about 100%, about 200%, or about 400% longer than that of the composition having substantially similar emulsion-free adsorbed starch granules. In any embodiment, the composition possesses an active ingredient activity that is at least about 10%, about 25%, about 50%, about 100%, about 200%, about 400% greater than that in a composition having substantially similar emulsion-free adsorbed starch granules. In any embodiment, the composition possesses an active ingredient activity that is at least about 25% or about 50% greater than that on the composition having substantially similar emulsion-free adsorbed starch granules. In any embodiment, the composition possesses an active ingredient activity that is at least about 100% or about 200% greater than that on the composition having substantially similar emulsion-free adsorbed starch granules.

In any embodiment, the composition is a product chosen from food, beverage, alternative-food, cannabinoid, industrial, pharmaceutical, cosmetic, cleaning, home care, flavor release, and fragrance products. In any embodiment, the composition is a product chosen from instant beverages, alternative meats, alternative foods, cannabinoid products, and other edible products. In any embodiment, the composition is a product chosen from beauty and health care products, such as but not limited to cosmetics, skin/hair care, home care, detergents, fragrance oils, kitty litter fragrance releasing agents, and the like. In any embodiment, the composition is a product chosen from pharmaceutical, nutritional, nutraceutical, and dietary products. In any embodiment, the composition is a product chosen from alternative-food, cannabinoid, industrial, pharmaceutical, nutraceutical, cosmetic, cleaning, flavor release, and fragrance products. In any embodiment, the composition is a product generated by clean label processes.

ASPECTS

Subject matter disclosed in this specification is set out in the following numbered embodiments:

Claim 1. A method for making an oil-loaded, free-flowing porous starch composition, the method comprising: a) obtaining a porous starch composition and an emulsion compound, the emulsion compound comprising an oil component, an aqueous phase, and an emulsifying agent; b) admixing the porous starch composition and the emulsion compound, to adsorb the oil component to the porous starch composition, thus providing the oil-loaded free-flowing porous starch composition; optionally, wherein the oil-loaded free-flowing porous starch composition comprises a starch particle; and optionally, wherein the oil-loaded free-flowing porous starch composition comprises a plurality of starch particles.

Claim 2. The method of claim 1 , wherein the porous starch composition comprises a porous starch particle; optionally, wherein the porous starch particle is made by enzymatic treatment of a starch particle.

Claim 3. The method of any of claims 1-2, wherein the porous starch composition is a native starch or a modified starch; wherein the modified starch is modified by a process chosen from: physical, mechanical, pressure, temperature, chemical, and enzyme processes, and combinations thereof.

Claim 4. The method of any of claims 1-3, wherein the emulsifying agent comprises a starch product; optionally, wherein the starch product is a water-soluble starch; optionally, wherein the starch product is a modified water-soluble starch; optionally, wherein the starch product is an OSA-modified water-soluble starch.

Claim 5. The method of any of claims 1-4, wherein the oil component is chosen from: plant-based oils; cannabis oil extracts; mineral oil; fatty acids; medium chain triglycerides; and mixtures thereof; optionally, wherein, the oil component comprises a plant-based oil; optionally, wherein the oil component comprises the plant-based oil and medium chain triglycerides.

Claim 6. The method of any of claims 1-5, wherein the emulsion compound contains a first amount of the oil component, and the oil-loaded free-flowing porous starch composition contains a second amount of the oil component; and wherein the second amount of the oil component is between about 10- 100% of the first amount of the oil component; between about 20-100%; between about 30-100%; between about 40-100%; between about 50-100%; between about 60-100%; between about 70-100%; between about 80-100%; or between about 90-100% of the first amount of the oil component; optionally, wherein the second amount of the oil component is between about 50-100%; between about 60-100%; between about 70-100%; between about 80-100%; or between about 90-100% of the first amount of the oil component; and optionally, wherein the second amount of the oil component is between about 70-100% of the first amount of the oil component.

Claim 7. The method of any of claims 1-6, wherein when the oil component is a 80:20 blend of orange oil: medium chain triglycerides, the oil-loaded free-flowing porous starch composition has an overall citrus aroma that has an aroma intensity measurable on a 15-point Universal Intensity scale; and wherein the aroma intensity of the overall citrus aroma is greater than about 40% of maximum value achievable on the 15-point Universal Intensity scale; optionally, wherein the aroma intensity of the overall citrus aroma is greater than about 50% of maximum value achievable on the 15-point Universal Intensity scale.

Claim 8. The method of any of claims 1-7, wherein when the oil component is a 80:20 blend of orange oil: medium chain triglycerides, the oil-loaded free-flowing porous starch composition has an oxidized aroma that has an aroma intensity measurable on a 15-point Universal Intensity scale; optionally, wherein the aroma intensity of the oxidized aroma is less than about 50% of the maximum value of a 15-point Universal Intensity scale; optionally, wherein the aroma intensity' of the oxidized aroma is less than about 30% of the maximum value of a 15-point Universal Intensity scale.

Claim 9. The method of any of claims 1-8, wherein a ratio of emulsion compound: oil-loaded free-flowing porous starch composition is chosen from: about 1:6, about 1 :5, about 1:4, about 1:3, about 1 :2, about 1: 1, and about 0.5: 1; optionally, wherein the ratio is between about 1 :1 and about 1:5.

Claim 10. The method of any of claims 1-9, wherein: i) at least one of the oil component, the aqueous phase, and the emulsifying agent comprises a first active ingredient, or the emulsifying compound comprises a second active ingredient; or ii) at least one of the oil component, the aqueous phase, and the emulsifying agent comprises the first active ingredient, and the emulsifying compound comprises the second active ingredient. Claim 11. The method of any of claims 1-10, wherein the emulsion compound is a particle having a diameter between about 1 and about 1000 microns, about 100 and about 1000 microns, about 150 and about 800 microns, about 15 and about 100 microns, about 0.5 and about 5 microns, and about 1 and about 1000 nanometers; optionally, wherein the emulsion compound has the diameter between about 1-1000 nanometers.

Claim 12. An oil-loaded, free-flowing porous starch composition made by the process of any one of claims 1-11.

Claim 13. An oil-loaded, free-flowing porous starch composition, comprising: a starch composition and an emulsion compound, the emulsion compound comprising an oil component, an aqueous component, and an emulsifying agent; optionally, wherein the oil-loaded free-flowing porous starch composition is a starch particle or a plurality of starch particles; optionally, wherein each emulsion compound has a diameter between about 1 and about 1000 microns, about 100 and about 1000 microns, about 150 and about 800 microns, about 15 and about 100 microns, about 0.5 and about 5 microns, and about 1 and about 1000 nanometers.

Claim 14. The oil-loaded, free-flowing porous starch composition of claim 13, wherein i) at least one of the oil component, the aqueous phase, and the emulsifying agent comprises a first active ingredient, or the emulsifying compound comprises a second active ingredient; or ii) at least one of the oil component, the aqueous phase, and the emulsify ing agent comprises the first active ingredient, and the emulsifying compound comprises the second active ingredient.

Claim 15. The oil-loaded, free-flowing porous starch composition of any of claims 13-14, wherein the oil component is chosen from: plant-based oils; fatty acids; cannabis oil extracts; mineral oil; medium chain triglycerides; and mixtures thereof.

Claim 16. The oil-loaded, free-flowing porous starch composition of any one of claims 13-15, wherein the emulsifying agent comprises a starch product; optionally, wherein the starch product is a water-soluble starch; optionally, wherein the starch product is a modified water-soluble starch; optionally, wherein the starch product is an OSA-modified water-soluble starch.

Claim 17. The oil-loaded, free-flowing porous starch composition of any one of claims 13-16, wherein the emulsion compound contains a first amount of oil and the oil- loaded, free-flowing porous starch composition contains a second amount of oil; and wherein the second amount of oil is between about 10-100% of the first amount of oil; between about 20-100%; between about 30-100%; between about 40-100%; between about 50-100%; between about 60-100%; between about 70- 100%; between about 80-100%; or between about 90-100% of the first amount of oil; optionally, wherein the second amount of oil is between about 50-100%; between about 60-100%; between about 70-100%; between about 80-100%; or between about 90-100% of the first amount of oil; and optionally, wherein the second amount of oil is between about 70-100%.

Claim 18. The oil-loaded, free-flowing porous starch composition of any one of claims 13-17, wherein when the oil component is a 80:20 blend of orange oil: medium chain triglycerides, the oil-loaded, free-flowing porous starch composition has an overall citrus aroma that is detectable to a human nose and the overall citrus aroma has an aroma intensity measurable on a 15-point Universal Intensity scale; and wherein the aroma intensity of the overall citrus aroma is greater than about 40% of maximum value achievable on the 15-point Universal Intensity scale; optionally, wherein the aroma intensity of the overall citrus aroma is greater than about 40% of maximum value achievable on the 15-point Universal Intensity scale.

Claim 19. The oil-loaded, free-flowing porous starch composition of any one of claims 13-18, wherein when the oil component is a 80:20 blend of orange oil: medium chain triglycerides, the oil-loaded, free-flowing porous starch composition has an oxidized aroma that is detectable to a human nose and the oxidized aroma has an aroma intensity measurable on a 15-point Universal Intensity scale; optionally, wherein the aroma intensity of the oxidized aroma is less than about 50% of the maximum value of a 15-point Universal Intensity scale; optionally, wherein the aroma intensity of the oxidized aroma is less than about 30% of the maximum value of a 15-point Universal Intensity scale.

Claim 20. The oil-loaded, free-flowing porous starch composition of any one of claims 13-19, wherein a ratio of emulsion compound: oil-loaded, free-flowing porous starch composition is chosen from: about 1 :6, about 1 :5, about 1:4, about 1:3, about 1:2, about 1:1, and about 0.5: 1; optionally, wherein the ratio is between 1 : 1 and 1 :5.

Claim 21. An edible composition comprising the oil-loaded, free-flowing porous starch composition made by the method of any one of claims 1-11; optionally, wherein the edible composition is chosen from food, beverage, animal feed, alternative-food, cannabinoid, industrial, pharmaceutical, nutraceutical, cosmetic, home care, flavor release, and fragrance compositions.

Claim 22. An edible composition comprising the oil-loaded, free-flowing porous starch composition of any one of claims 13-20; optionally, wherein the edible composition is chosen from food, beverage, animal feed, alternative-food, cannabinoid, industrial, pharmaceutical, nutraceutical, cosmetic, home care, flavor release, and fragrance compositions. Claim 23. Use of the edible composition of any one of claims 21 and 22 to deliver an active ingredient.

The technology' disclosed in this specification can be better understood with reference to the following Examples, which are provided for illustrative purposes and are not intended to be limiting in any way.

Preparation of Emulsion Compositions;

Generally, an emulsion composition comprises an oil, water or other liquid, and emulsifier (or emulsifying agent). The emulsifier is dispersed in a water phase, which can contain one or more buffering agents (e.g., sodium benzoate, citric acid). Then, a pre-emulsion composition is prepared by slowly adding the oil or oil blend to the water phase dispersion in an LCI high shear mixer (e.g., Model HSM-100 LCI from Charles Ross & Son Company), with stirring (e.g., at 5000 rpm for 2 minutes). An exemplary pre-emulsion formulation is provided in Table 1. The pre-emulsion composition is subsequently homogenized by at least two passes through an APV pressure homogenizer (e.g., Model 15 MR Laboratory Homogenizer from APV Gaulin); this is done to obtain a desired particle size based on application (e.g., coarser (1-5 micron) or finer (0.3-1.0 micron)). Examples of pressure settings used include: i) the second stage set at 500 psi and the first stage set at 3000 psi; and ii) the second stage set at 500 psi and the first stage set at 4500 psi. The pressure can be varied based on active ingredients used and application requirements.

In some embodiments, one or more components of the emulsion composition comprise an active ingredient. Any of the oil, liquid, or emulsifying agent can be an active ingredient. In any embodiment, the emulsifying composition comprises an additional ingredient that acts as an active ingredient.

The oil may be present in the emulsion composition in any desirable amount possible and for any desired oil load, the oil load being the amount of oil present in the liquid phase of the emulsion composition. The type and amount of oil present will depend upon many parameters, but specifically can be altered to provide amounts of emulsifier product recommended in the desired applications. The emulsifier: oil ratio of the emulsion may also be any desired ratio and will also depend upon many parameters. In one example, the emulsifieroil ratio is 0.5 : 1 or 1: 1, orl:3 or 1:4 or 1 :6. Preferably, the emulsifier: oil ratio is any ratio suitable for food and beverage applications.

Table 1. Formulation for Exemplary Emulsion Composition

Example 1 (emulsion preparation)

An emulsion composition, made according using the pre-emulsion formulation of Table 1, was prepared by dissolving 0.15% sodium benzoate in water, then by adding 0.3% citric acid in water, and then adding 35% Q-NATURALE® saponin extract (as an emulsifying agent) in a 0.15% sodium benzoate solution at room temperature with moderate stirring. An emulsion composition was thus provided. A pre-emulsion composition was prepared using a high shear mixer (LCI high shear mixer), by slowly adding 50% (5 -fold) orange oil into the emulsion mixture. The pre- emulsion composition was homogenized using a high-pressure homogenizer (APV), with 2 passes on the APV. Here, the following APV settings used were: 1st stage = 4500 psi, and 2nd stage = 500 psi. The particle size of the resulting prepared emulsion composition was measured by Beckman Coulter particle size analyzer. For this example, as shown in Figure 1, the mean particle size obtained for the pre-emulsion composition was about 1 micron, while the mean particle size obtained for the emulsion composition was about 0.1-0.15 microns when freshly made and after storage at 57°C for 24 hours.

Example 2 (plating preparations)

The emulsion composition described in Example 1 was plated onto porous starch particles. The emulsion composition was made using the ingredients listed in Table 1. To do this, 25 gm of N-ZORBIT® 2144 starch particles was weighed, and then slowly added to the emulsion composition made with Q-NATURALE® emulsifier, with constant mixing using a mixer (e.g., Hobart mixer). The resulting slurry mixture was observed periodically until a paste form was reached, to determine the maximum plating capacity of the system. The mean particle size of the samples was also periodically measured, using the Beckman Coulter particle size analyzer.

Additional pre-emulsion compositions were prepared, each made with different amounts of oil to provide a 50% oil load with the orange oil. Emulsion compositions were made by applying the pre-emulsion compositions to N-ZORBIT 2144® plating agent, to load different amounts of oil onto the porous starch particles, as shown in Table 2.

Table 2. Formulations of Emulsion Compositions

As shown in Figure 2, emulsion compositions possessing oil loads between about 14-23% were plated or adsorbed onto the porous starch particles, providing plated or adsorbed starch particles that retained their flowable, solid state. As shown in Figure 3, the mean particle size measured for untreated porous starch granules was about 65- 75 microns, while the mean particle size obtained after emulsion compositions were adsorbed onto the porous starch granules was between about 200-800 microns.

Example 3 (emulsion preparation and plating preparation)

An emulsion composition was prepared according to the formulation provided in Table 3, using a high shear mixer (LCI high shear mixer), by slowly adding a medium chain triglycerides oil into a mixture of the aqueous phase ingredients. The pre-emulsion solution was homogenized using a high-pressure-homogenizer (APV), with 2 passes on the APV. For this example, a 41.2% oil load was provided and the APV settings used were: 1st stage = 4500 psi, and 2nd stage = 500 psi. The particle size of the resulting prepared emulsion composition was measured by Beckman Coulter particle size analyzer, shown in Figure 4. For this example, the mean particle size was less than about 0.8 micron when fresh and about 1 micron after aging at 50°C for 24 hours. Different amounts of the emulsion composition were plated onto N-ZORBIT® 2144 plating agent starch particles to provide plated starch particles that retained their flowable, solid state (Figure 5, showing a negative control (N-ZORBIT® 2144 only) and N-ZORBIT® 2144 plated with about 25% or about 50% oil load).

Table 3. Formulation for Emulsion Composition

Example 4 (emulsion preparation and plating preparation)

An emulsion composition was prepared by according to the formulation provided in Table 4, using a high shear mixer (LCI high shear mixer), by adding a PURITY GUM® Ultra OSA starch, and then maltodextrin into the emulsion mixture, providing 41.2% of the final emulsion composition. The medium chain trigly cerides was slowly added using a high shear mixer.

For this example, a 70% oil load was provided by the medium chain triglycerides and the APV settings used were: 1st stage = 4500 psi, and 2nd stage = 500 psi.

The particle size of the resulting prepared emulsion composition was measured by Beckman Coulter particle size analyzer, shown in Figure 6. For this example, the mean particle size was less than about 2.9 microns when fresh and about 3.7 microns after aging at 50°C for 24 hours. Different amounts of the emulsion composition were plated onto N-ZORBIT® 2144 starch particles to provide plated starch particles that retained their flowable, solid state (Figure 7, showing a negative control (N-ZORBIT 2144® only) and N-ZORBIT® 2144 plated with about 10-20% oil load). Different amounts of the emulsion composition were plated onto porous starch particles. To do this, 25 gm of N-ZORBIT® 2144 plating agent was weighed, and then slowly added to the emulsion composition made with medium chain triglycerides, OSA starch, and maltodextrin, with consistent mixing using a mixer (e.g., Hobart mixer). The resulting slurry was observed periodically until the paste form was reached, to assess the maximum plating capacity of the system. The mean particle sizes of the sample were also periodically measured, using the Beckman Coulter particle size analyzer, as shown in Figure 8, were the plated porous starch particles achieved mean particle sizes between about 480-870 microns.

Table 4. Formulation for Emulsion Composition

As shown in Figures 2, 5, and 7, emulsion compositions were plated or adsorbed onto the porous starch particles, providing plated starch particles that retained their flowable, solid state. The porous starch granules were plated with amounts of emulsifying compositions that provided oil loads of about 8-22% on the plated or adsorbed porous starch granules, while the plated or adsorbed porous starch granules retained their flowable state. Further, the porous starch granules accepted loads of emulsion compositions that provided between about 16-49% of the weight of the free-flowing adsorbed starch particle composition.

As shown in Figures 3 and 8, the free-flowing adsorbed starch particle composition possessed increasingly larger particle sizes, when adsorbed to correspondingly greater amounts of emulsion compositions. Here, mean particle sizes between about 190-870 microns were measured. Example 5: Emulsion for plated application Experiment 1

An emulsion composition, made using the pre-emulsion formulation according to Table 5, was prepared by dissolving 0.15% sodium benzoate in water, then by adding 0.3% citric acid in water, and then adding 12% Purity Gum 2000® starch (as an emulsifying agent). A pre-emulsion composition was prepared using a high shear mixer (LCI high shear mixer), by slowly adding 16% of a blended oil mixture (1 -fold orange oil and MCT in an 80:20 ratio) into the mixed emulsion ingredients. The pre- emulsion composition was homogenized using a high-pressure homogenizer (APV) device, with 2 passes on the APV. Here, the following APV settings used were: 1st stage = 4500 psi, and 2nd stage = 500 psi.

Table 5, Formulation for Emulsion Composition

The emulsion composition described in Experiment 1 was plated onto porous starch particles of N-ZORBIT® 2144 as follows: 50 gm of N-ZORBIT® 2144 starch particles was weighed, and then 27.0 gm of the emulsion composition (made with Purity Gum® 2000 emulsifier) was slowly added to the starch particles, with constant mixing using a proper mixer, using the ingredients and proportions recited in Table 6. The resulting slurry mixture was visually observed periodically to determine the maximum emulsion plating capacity of the oil-loaded starch particles.

Table 6

Example 6: Emulsion for spray dry application Experiment 2 An emulsion composition of 4.5% flavored oil was made according to the formulation of Table 7 by adding 29.0% Purity Gum 2000® (as an emulsifying agent) into water. A pre-emulsion composition was prepared using a high shear mixer (LCI high shear mixer), by slowly adding 1.76% of oil blend (1-fold orange oil and MCT in an 80:20 ratio) into the emulsion mixture. The pre-emulsion composition was homogenized using a high-pressure homogenizer (APV), with 2 passes on the APV. Here, the following APV settings used were: 1st stage = 4500 psi, and 2nd stage = 500 psi.

Table 7

The homogenized emulsion composition was spray-dried using an inlet temperature of 160-180°C and outlet temperature of 85-95°C. The resulting oil- loaded, spray-dried composition was a powder composed of the ingredients and proportions recited in Table 8.

Table 8; Spray Dried powder composition

Example 7: Plated oil as is (80% 1-fold orange oil +20% MCT) Experiment 3

As shown in Table 9, a formulation was made as follows: 50 gm of N- ZORBIT® 2144 starch particles was weighed, and then 3.0 gm of oil blend (a mixture of 2.4 gm 1-fold orange oil and 0.6 gm of MCT) was slowly added with constant mixing using a proper mixer. The resulting slurry mixture was visually observed periodically to determine the oil plating capacity of the oil-loaded starch particles (when oil was loaded directly, in the absence of an emulsifying agent). Table 9

The resulting powdered solids obtained from Examples 5-7 were analyzed for oil protection, stability, and for quality of sensory attributes. These experiments were performed with oil solutions that were prepared fresh and frozen until testing, or age- accelerated at 50°C for 15 days (to provide samples representative of samples exposed to a 6-month shelf-life cycle).

Example 8: Gas Chromatography analysis (Absolute Oil Retention)

The resulting solid powders obtained from Examples 5-7 were analyzed for oil protection. That is, known amounts of oil were loaded onto starch particles using a variety of methods and materials. After the loading processes were complete, the samples were evaluated by gas chromatography to determine the amount of oil that was loaded onto the samples, expressed as a percentage of the total amount of oil loaded.

Oil compositions or oil emulsion compositions were loaded onto starch particles via plating or by spray-drying. The experiments were performed using oil- loaded starch compositions that were prepared fresh or were aged at 50°C for 15 days. The same oil blends were plated onto porous starch granules (N-ZORBIT 2144) directly (Plated oil as is), or were suspended in an emulsion, which was then plated onto porous starch granules (Plated emulsion). Oil compositions were emulsified with hydrophobic starch product (Purity Gum 2000) and subjected to spray drying (Spray dried). After the oil compositions or oil emulsion compositions were plated or loaded onto starch granules, the amount of oil retained by the treated starch granules was measured by gas chromatographic analysis and reported as a percentage of the oil applied to the starch particles, as shown in Figure 9 and in Table 10.

The total amount of oil present in the samples was determined on a full evaporation technique headspace gas chromatography/flame ionizing detector (Agilent GC (7890B)), using a Stabilwax-DA column (30 m x 0.53 mm x 1.5 pm) and helium at 5.0 rnL/min at 5.0 ml/min flow rate. 50 pl of ethyl benzoate was added to 25 ml dimethyl sulfoxide. 500 mg of sample was added, to provide 20-30% by weight of oil. Aliquots of sample preparation were analyzed on the gas chromatograph. The inlet settings for the gas chromatograph were: Detection temperature: 240 °C; Injection Mode: Split Pressure: 3.791 psi; Split Ratio: 20: 1 Split Flow: 100 ml/min; Total Flow: 108 ml/min Septum Purge Flow: 3 ml/min. The flame ionizing detector settings were: Detector Temperature: 240°C Hydrogen Flow: 30 mL/min Air Flow: 400 mL/min; Helium Make-Up Flow: 25 mL/min Samples were analyzed in triplicate (n = 3), with mean values reported in Figure 9 and Table 10.

When fresh, the oil-loaded porous starch granules (Plated oil as is) retained about 70% of the oil in the composition. When aged, the oil-loaded porous starch granules retained less than 20% of the oil in the oil solution, suggesting that the oilloading performance of porous starch granules is decreased with aging.

When oil compositions were made into an oil emulsion composition prior to plating onto the porous starch granules, then the porous starch particles (Plated emulsion) retained over 80% or 90% of the oil in the oil solutions, showing a significant improvement in the amount of oil retained by the particles. While the porous starch particles still retained greater amounts of fresh oil compared to aged oil, the particles still retained a greater amount of oil that was applied as an oil emulsion composition compared to the plated oil emulsion (plated oil as is).

When the oil emulsion compositions were spray dried (Spray dried), the oilcontaining starch materials retained about 80% of the oil, and retained fresh oil and aged oil in similar amounts.

Two of the experimental methods employed provided similar initial delivery of oil onto starch granules: spray dry ing of oil emulsion compositions and plating of oil emulsion compositions onto porous starch granules. These methods also showed retention of similar amounts of oil when aged.

Table 10

Example 9: Sensory evaluations of oil-loaded starch compounds Each of the oil-loaded starch particle compositions made in Figure 9 and Table 10 was subjected to sensory evaluations provided by a panel of trained sensory analysts.

A panel of 8 highly trained human panelists evaluated each set of samples, each following the same sensory protocol. The samples were evaluated at room temperature conditions (70°F/20°C), with each panelist using their nose to smell each sample. The samples were assessed for intensity of aroma on a 15 point Universal Intensity Scale, for the intensity of overall citrus aroma and oxidized aroma, where the intensity of each aroma was assessed on a scale between 1 (least intensity) to 15 (greatest intensity). The averages or means of the scores are reported in Figure 10 and Table 11.

The same samples, which were loaded with orange oil, were assessed for the intensity of two scents delivered by the samples: the overall citrus aroma, which is the desired “orangey” scent associated with citrus fruits, and the oxidized aroma, which is an unwanted off-note associated with degraded oil compounds.

Table 11

Regarding the assessment of overall citrus aroma, when fresh orange oil compositions were loaded onto starch particles, all of the methods provided measurable intensity of overall citrus aroma for the experimental samples, though the oil emulsion plated onto porous starch granules delivered the overall citrus aroma of greatest intensity to the panel of sensory analysts. The only method that provided samples yielding low or no intensity scores for overall citrus aroma was for aged matrixes of oil compositions plated onto porous starch granules (Plated oil as is (Aged)).

When oil was loaded onto starch particles, using the methods described above, and then aged, smaller intensities of overall citrus aroma was reported by the sensory panelists. However, the methods with aged oil emulsion compositions and starch particles mixtures (plated emulsion (Aged) and Spray dried (Aged)), generated samples that delivered significantly greater intensities of overall citrus aroma. In comparison, the aged oil composition (plated oil as is (Aged)), delivered as an oil and not as part of an oil emulsion, generated samples that had little or no intensity of overall citrus aroma.

Regarding the assessment of oxidized aroma, the results reported by the sensory panel are generally reversed, compared to the assessment of overall citrus aroma. Most of the methods provided compositions delivering oxidized aromas of equal or lesser intensity than that of the corresponding overall citrus aroma, except Plated oil as is (Aged). The loading solutions that contained fresh oil generated lower intensity scores for oxidized aroma, when compared to counterparts that were aged.

The oil emulsion plated onto porous starch granules method delivered the combination of highest intensity levels of overall citrus aroma and lowest intensity levels of oxidized citrus aroma. This phenomenon was observed when the blended compositions were tested as fresh or aged, although the fresh oil delivered greater contrasts between the different aromas.

Taken together, the oil emulsion plated onto porous starch granules method provides for loading and retaining greater amounts of oil onto starch carriers (using spray-drying or plating-porous methods), and the resulting starch particle carriers (whether fresh or aged) contemporaneously delivering a superior sensory experience (greater intensity of desired overall citrus aroma coupled with lesser intensity of unwanted oxidized aroma) when compared to directly loading oil (in the absence of an emulsifying agent) onto porous starch granules, and versus spray-drying. That is, current methods used to load oil onto starch particle products were improved when instead of loading oil directly to starch particles, the oil was loaded as part of an oil- and-liquid emulsion. But the other new methods provided even better results.

Further, the methods used to load the oil emulsion onto starch particles also made a difference in the particles’ ability to retain oil and to deliver aromas. Both spray-drying and plating onto porous starch granules were methods that provided products that absorbed significant percentages of the oil applied. However, there was a measurable loss in the amount of oil retained by the spray-dried starch powder (though the amounts of oil retained remained over 70% of the oil applied). In comparison, the porous-plated emulsions achieved total or near total retention of fresh oil applied to it, as well as delivering a superior sensory experience (a greater intensity of desired overall citrus aroma coupled with lesser intensity of oxidized aroma), when compared to the spray-dried starch products. And surprisingly, the improved delivery of oil was demonstrated when the final product composition contained water.

Example 10: Stability of oil-loaded starch compounds

Orange oil blend was loaded onto different types of starch products using different methods: i) applying oil compounds onto non-porous starch particles: ii) incorporating oil compounds into oil-and-liquid emulsions and loading them onto non-porous starch products; and iii) incorporating oil compounds into oil-and-liquid emulsions and loading them onto porous starch particles. Each of the oil-loaded starch compositions made in Figure 9 and Table 10 was assessed for its ability to retain the oil compounds loaded onto them, and for the intensity of preferred aromas and unwanted off-notes delivered by the oil compounds. Figure 10 and Table 11 assessed the same compositions for their capacity to deliver desired aromas and undesired off- note aromas.

The samples were tested for amount of oil present, intensity of overall citrus aroma, and intensity of oxidized aroma. They samples were tested when freshly prepared and after being subjected to conditions that simulated shelf-life aging, to determine whether these properties persisted with time and continued to protect the active ingredients over the shelf-life of the experimental products.

All samples took on measurable amounts of oil initially, and all samples possessed smaller amounts of oil after aging, though the plated emulsion group contained the largest amounts of oil initially. The other experimental groups exhibited the greatest losses of oil over time.

In addition to measuring the amount of oil physically delivered to the starch products, functional aspects of the oil compound were also tested. The same samples, which had been loaded with orange oil, were assessed for intensity of two citrus scents delivered by the samples: the overall citrus aroma, which is the “orangey” scent associated with citrus fruits and the oxidized aroma, which is an off-note associated with degraded oil compounds. Just as all samples took on measurable amounts of oil, all samples also delivered measurable amounts of aroma intensities. Most of the samples delivered greater intensities of overall citrus aroma than oxidized aroma.

With aging, all samples generally exhibited a decrease in overall citrus aroma intensity and an increase in oxidized aroma. The most marked change was observed where the oil was delivered without being part of an emulsion. Those samples exhibited an oxidized aroma intensity that far exceeded the overall citrus aroma intensity. In contrast, the other experimental groups retained a significant overall citrus aroma intensity. Of these groups, one (oil emulsion plated onto nonporous particles) retained a greater overall citrus aroma intensity and smaller oxidized aroma intensity. In other words, with aging, the plated emulsion group retained the most “good” smell and the least “bad” smell of the samples.

In addition to the gas chromatography results, the sensory data confirms that the methods described herein provide an increase in the protection of the active ingredients present in oil compounds, when oil compounds are stored on starch particles. And surprisingly, the improved stability was demonstrated when the final product composition contained water. We report improvements in known methods, and report novel methods (loading oil-and-liquid emulsions onto porous starch particles) that provide superior protection of the active ingredients present in oil compounds, improving the amount and functionality of oil compounds thus delivered, especially when the delivery occurs at a later time, which ultimately improves the shelf-life of these products.