CA2614348A1 - Food articles with delivery devices and methods for the preparation thereof - Google Patents

Abstract

Disclosed are food articles comprising microcapsules as delivery devices.
Methods of preparing such food articles are also disclosed.

Description

FOOD ARTICLES WITH DELIVERY DEVICES AND METHODS
FOR THE PREPARATION THEREOF

CROSS REFERENCE TO RELATED APPLICATIONS
This application claims the benefit of priority to U.S. Provisional Patent Application 60/697,092, filed July 7, 2005., U.S. Provisional Patent Application 60/811,830, filed June 8, 2006, U.S. Provisional Patent Application 60/811,503, filed June 7, 2006, and U.S. Utility Application 11/435,605, filed May 17, 2006, which are all incorporated by reference herein in their entireties.
FIELD
The disclosure generally relates to food articles comprising delivery devices.
Methods of preparing such food articles are also disclosed.
BACKGROUND
Polyunsaturated fatty acids, for example, omega-3 fatty acids, are vital to everyday life and function. Such compounds play critical roles in the structure of cell membranes and they form the foundation for the synthesis of many cell mediators (e.g., prostaglandins and leukotrienies). These cell mediators are an important part of human physiology and can affect, for example, cell proliferation, cell signaling, gene expression, coagulation, and inflammation.

As an example, omega-3 fatty acids and their derivates are known to be primary components of brain and nerve tissue. Also, omega-3 fatty acids can reduce thrombogenisis and inflammation by altering, certain pathways leading to the production of inflammatory mediators (e.g., prostaglandins, leukotrienes aild thromboxanes). See e.g., Sugano, Michihiro. "Balanced intake of polyunsaturated fatty acids for health benefits." Journal of Oleo Science (2001), 50(5):305-311. Further, omega-3 fatty acids are known to positively affect heart function, hemodynamics, and arterial endothelial function. The American Heart Association has reported that omega-3 fatty acids can reduce cardiovascular and heart disease risk.

The primary source of such polyunsaturated fatty acids is through diet. Diets rich in polyunsaturated fatty acids like omega-3 fatty acids are known to have beneficial effects for heart disease, cancer, arthritis, allergies, and other chronic diseases. (See e.g., The American Heart Association, Scientific Statement, "Fish Consumption, Fish Oil, Omega-3 Fatty Acids and Cardiovascular Disease," November 2002; Radack et al., "The effects of low doses of omega-3 fatty acid stipplementation on blood pressure in hypertensive subjects: a randomized controlled trial." Arch. Intern. Med.
(1991) 151:1173-1180; Appel et al., "Does supplementation of diet with 'fish oil' reduce blood pressure? A meta-analysis of controlled clinical trials. Arch. Interta. Med.
(1993) 153(12):1429-1438; GISSI-Prevenzione Investigators. "Dietary supplementation with omega-3 polyunsaturated fatty acids and vitamin E after myocardial infarction:
results of the GISSI-Prevenzione trial." Lancet (1999) 354:447-455.) The Ariierican Heart Association has recommended that people may need 2 to 4 grams of omega-3 fatty acids per day. Unfortunately, most western diets are deficient in these beneficial fatty acids. Even a 1 gram/day dose may be more than can readily be achieved through diet alone. Thus, people who desire to increa.s.e their intake of such polyunsaturated fatty acids typically turn to dietary supplements. Such supplernents, however, are usually sensitive to oxidation and can be foul smelling and tasting. Further, compliance with dietary supplement regimens requires discipline, which is often wanting.
In light of the health benefits of polyunsaturated fatty acids and the problems associated with adequate intalce of such compounds, what is needed in the art are food articles containing. beneficial compounds such as, for example, polyunsaturated fatty acids and which are more palatable and pleasing to the consumer. The subject matter disclosed herein meets these and other needs.
SUMMARY
In accordance with the purposes of the disclosed materials, compounds, compositions, articles, and methods, as embodied and broadly described herein, the disclosed subject matter, in one aspect, relates to compounds and compositions and methods for preparing and using such compounds and compositions. In a further aspect, the disclosed subject matter relates to articles of food comprising delivery devices. In a still further aspect, the disclosed subject matter relates to methods of preparing such food articles. In yet a further aspect, the disclosed subject matter relates to homogenized formulations that comprise microcapsules, and to food articles prepared with or comprising homogenized formulations. In a still further aspect, the disclosed subject matter relates to methods of making and using the disclosed homogenized formulations and food articles prepared from and comprising them.
Additional advantages will be set forth in part in the description that follows, and in part will be obvious from the description, or may be learned by practice of the aspects described below. The advantages described below will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to

2 be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive.

BRIEF DESCRIPTION OF THE DRAWINGS
The accompanying figures, which are incorporated in and constitute a part of this specification, illustrate several aspects described below.

Figure 1 is a schematic of a process for applying the disclosed microencapsulated nutrients on to chips.

DETAILED DESCRIPTION
The materials, compounds, compositions, articles, and methods described herein can be understood more readily by reference to the following detailed description of specific aspects of the disclosed subject matter and the Examples included therein and to the Figure.

Before the present materials, compounds, compositions, articles, and methods are disclosed and described, it is to be understood that the aspects described below are not limited to specific synthetic methods or specific reagents, as such may, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting.

Also, throughout this specification, various publications are referenced. The disclosures of these publications in their entireties are hereby incorporated by reference into this application in order to more fully describe the state of the art to which the disclosed matter pertains. The references disclosed are also individually and specifically incorporated by reference herein for the material contained in them that is discussed in the sentence in which the reference is relied upon.

In this specification and in the claims that follow, reference will be made ta a number of terms, which shall be defined to have the following meanings:
Throughout the description and claims of this specification the word "comprise"
and other forms of the word, such as "comprising" and "comprises," means including but not limited to, and is not intended to exclude, for example, other additives, components, integers, or steps.

As used in the description and the appended claims, the singular forms "a,"
"an,"
and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a compound" includes mixtures of two or more such compounds, reference to "an omega-3 fatty acid" includes mixtures of two or more such omega-3 fatty

3

4 PCT/US2006/024735 acids, reference to "the microcapsule" includes mixtures of two or more such microcapsules, and the like.
"Optional" or "optionally" means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where the event or circumstance occurs and instances where it does not.
Ranges can be expressed herein as from "about" one particular value, and/or to "about" another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value.
Similarly, when values are expressed as approximations, by use of the antecedent "about,"
it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as "about"
that particular value in addition to the value itself. For example, if the value "10" is disclosed, then "about 10" is also disclosed. It is also understood that when a value is disclosed that "less than or equal to" the value, "greater than or equal to the value" and possible ranges between values are also disclosed, as appropriately understood by the skilled artisan. For example, if the value "10" is disclosed, then "less than or equal to 10"
as well as "greater than or equal to 14" is also disclosed. It is also understood that throughout the application data are provided in a number of different formats and that these data represent endpoints and starting points and ranges for any combination of the data points. For example, if a particular data point "10" and a particular data point "15"
are disclosed, it is understood that greater than, greater than or equal to, less than, less than or equal to, and equal to 10 and 15 are considered disclosed as well as between 10 and 15. It is also understood that each unit between two particular units are also disclosed. For example, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are also disclosed.

References in the specification and concluding claims to parts by weight of a particular element or component in a composition denotes the weight relationship between the element or component and any other elements or components in the composition or article for which a part by weight is expressed. Thus, in a compound containing 2 parts by weight of component X and 5 parts by weight component Y, X and Y are present at a weight ratio of 2:5, and are present in such ratio regardless of whether additional components are contained in the compound.

A weight percent of a component, unless specifically stated to the contrary, is based on the total weight of the formulation or composition in which the component is included.
As used herein, by a "subject" is meant an individual. Thus, the "subject" can include domesticated animals (e.g., cats, dogs, etc.), livestock (e.g., cattle, horses, pigs, sheep, goats, etc.), laboratory animals (e.g., mouse, rabbit, rat, guinea pig, etc.), and birds.
"Subject" can also include a mammal, such as a primate or a human.
Reference will now be made in detail to specific aspects of the disclosed materials, compounds, compositions, articles, and methods, examples of which are illustrated in the accompanying Examples and Figure.
Certain materials, compounds, compositions, and components disclosed herein can be obtained commercially or readily synthesized using techniques generally known to those of skill in the art. For example, the starting materials and reagents used in preparing the disclosed compounds and compositions are either available from commercial suppliers such as. Ocean Nutrition Canada (Dartmouth, Nova Scotia), Aldrich Chemical Co., (Milwaukee, Wis.), Acros Organics (Morris Plains, N.J.), Fisher Scientific (Pittsburgh, Pa.), or Sigma (St. Louis, Mo.) or are prepared by methods known to those skilled in the art following procedures set forth in references such as Fieser and Fieser's Reagents for Organic Synthesis, Volumes 1-17 (John Wiley and Sons, 1991);
Rodd's Chemistry of Carbon Compounds, Volumes 1-5 and Supplementals (Elsevier Science Publishers, 1989); Organic Reactions, Volumes 1-40 (John Wiley and Sons, 1991);
March's Advanced Organic Chemistry, (John Wiley and Sons, 4th Edition); and Larock's Comprehensive Organic Transfomzations (VCH Publishers Inc., 1989).
Also, disclosed herein are materials, compounds, compositions, and components that can be used for, can be used in conjunction with, can be used in preparation for, or are products of the disclosed methods and compositions. These and other materials are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these materials are disclosed that while specific reference of each various individual and collective combinations and permutation of these compounds may not be explicitly disclosed, each is specifically contemplated and described herein.
For example, if a compound is disclosed and a number of modifications that can be made to a number of components of the compound are discussed, each and every, combination and permutation that are possible are specifically contemplated unless specifically indicated to the contrary. Thus, if a class of components A, B, and C are disclosed as well as a class of components D, E, and F and an example of a combination compound A-D is disclosed, then even if each is not individually recited, each is individually and collectively~
contemplated. Thus, in this example, each of the combinations A-E, A-F, B-D, B-E, B-F, C-D, C-E, and C-F are specifically contemplated and should be considered disclosed from disclosure of A, B, and C; D, E, and F; and the example combination A-D.
Likewise, any subset or combination of these is also specifically contemplated and disclosed. Thus, for example, the sub-group of A-E, B-F, and C-E are specifically contemplated and should be considered disclosed from disclosure of A, B, and C; D, E, and F; and the example combination A-D. This concept applies to all aspects of this disclosure including, but not limited to, steps in methods of making and using the disclosed compositions.
Thus, if there are a variety of additional steps that can be performed it is understood that each of these additional steps can be performed with any specific aspect or combination of aspects of the disclosed methods, and that each such combination is specifically contemplated and should be considered disclosed.
Food Articles Disclosed herein are food articles that comprise one or more delivery devices.
A
delivery device, as is more fully described herein, can contain a loading substance that is to be delivered to a subject upon eating/drinking the food article. The disclosed food articles can be any article that can be consumed (e.g., eaten, drank, or ingested) by a subject. For example, the food article can be a composition for human and animal consumption, including foods/beverages for consumption by agricultural animals, pets and zoo animals. It can be desired that the food article be a palatable and popular food article. By using food articles that are widely accepted, compliance with dietary or dosage regimens for the loading substance can be increased.
Those of ordinary skill in the art of preparing and selling food articles (i.e., edible foods or beverages, or precursors thereof) are well aware of a large variety of classes, subclasses, and species of food articles, and utilize well-known and recognized terms of art to refer to those articles while endeavoring to prepare and sell variations of those articles. Such a list of terms of art is enumerated below, and it is specifically contemplated hereby that the various delivery devices disclosed herein can be used to deliver a loading substance to a subject by incorporating the delivery device(s) into or on a food article as listed herein, either singly or in all reasonable combinations or mixtures thereof:

One or more confectioneries, chocolate confectionery, tablets, countlines, bagged selflines/softlines, boxed assortments, standard boxed assortments, twist wrapped miniatures, seasonal chocolate, chocolate with toys, alfajores, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastilles, gums, jellies and chews, toffees, caramels and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, gum, chewing gum, sugarized gum, sugar-free gum, functional gum, bubble gum, bread, packaged/industrial bread, unpackaged/artisanal bread, pastries, cakes, packaged/industrial cakes, unpackaged/artisanal cakes, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savory biscuits and crackers, bread substitutes, breakfast cereals, RTE (ready-to-eat) cereals, family breakfast cereals, flakes, muesli, other RTE cereals, children's breakfast cereals, hot cereals, sweet and savory snacks, fruit snacks, chips/crisps, extruded snacks, tortilla/corn chips, popcorn, pretzels, nuts, other sweet and savory snacks, snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacement products, slimming products, convalescence drinks, ready meals, canned ready meals, frozen ready meals, dried ready meals, chilled ready meals, dinner mixes, dessert mixes, frozen pizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup, chilled soup, frozen soup, pasta, canned pasta, dried pasta, chilled/fresh pasta, noodles, plain noodles, instant noodles, frozen noodles, cups/bowl instant noodles, pouch instant noodles, chilled noodles, snack noodles, canned food, canned meat and meat products, canned fish/seafood, canned vegetables, canned tomatoes, canned beans, canned fruit, canned ready meals, canned pasta, other canned foods, frozen food, frozen processed red meat, frozen processed poultry, frozen processed fish/seafood, frozen processed vegetables, frozen meat substitutes, frozen potatoes, oven baked potato chips, other oven baked potato products, non-oven frozen potatoes, frozen bakery products, frozen desserts, other frozen food, dried food, chilled processed meats, chilled fisli/seafood products, chilled processed fish, chilled coated fish, chilled smoked fish, chilled lunch kit, chilled/fresh pasta, chilled noodles, oils and fats, olive oil, vegetable and seed oil, cooking fats, butter, margarine, spreadable oils and fats, functional spreadable oils and fats, sauces, dressings, and condiments, tomato pastes and purees, bouillon/stock cubes, stock cubes, gravy granules, liquid stocks and fonds, herbs and spices, fermented sauces, soy based sauces, pasta sauces, wet sauces, dry sauces/powder mixes, ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings, regular salad dressings, low fat salad dressings, vinaigrettes, dips, pickled products, other sauces, dressings and condiments, spreads, jams and preserves, honey, chocolate spreads, nut-based spreads, and yeast-based spreads.
Some other specific examples of suitable food articles include, but are not limited to, fruit, vegetable, meat, a grain food, a starch food, a confectionery such as sweets (hard and soft candy, jelly, jam, candy bar, etc.), gum, a baked confectionery or molded confectionery (cookie, biscuit, etc.), a steamed confectionery, a cacao or cacao product (chocolate and cocoa), a frozen confectionery (ice cream, ices, etc.), a beverage (fruit juice, soft drink, carbonated beverage, health drink), a health or nutritional bar, baked good, pasta, a milk product, a cheese product, an egg product, a condiment, a soup mix, a snack food, a nut product, a plant protein product, a poultry product, a granulated sugar (e.g., white or brown), a sauce, a gravy, a syrup, a dry beverage powder, a fish product, or pet companion food. In other examples, a suitable food article can include, but is not limited to, bread, tortillas, cereal, sausage, chicken, ice cream, yogurt, milk, salad dressing, rice bran, fruit juice, a dry beverage powder, rolls, cookies, crackers, fruit pies, or cakes. In some particular examples, the food article can be a chip (potato chip, corn chip, tortilla chip, etc.), pretzel, cracker, and the like. In still other examples, the food article can include, but is not limited to, frozen foods (e.g., frozen vegetables). In a further example, the food article is a salty, savory snack food such as, for example, a rice cake or popcorn.
Further examples of food articles that can contain delivery devices, as disclosed herein, can be the in the Wet Soup Category, the Dehydrated and Culinary Food Category, the Beverage Category, the Frozen Food Category, the Snack Food Category, and seasonings or seasoning blends.
"Wet Soup Category" means wet/liquid soups regardless of concentration or container, including frozen soups. For the purpose of this definition soup(s) means a food prepared from meat, poultry, fish, vegetables, grains, fruit and other ingredients, cooked in a liquid, which may include visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed or chunky, ready-to-serve, semi-condensed or condensed and can be served hot or cold, as a first course or as the main course of a meal or as a between meal snack (sipped like a beverage).
Soup can be used as an ingredient for preparing other meal components and can range from broths (consomme) to sauces (cream or cheese-based soups).
"Dehydrated and Culinary Food Category" means: (i) Cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology); (ii) Meal solutions products such as: dehydrated and freeze dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or ambient preparations of ready-made dishes, meals and single serve entrees including pasta, potato and rice dishes; and (iii) Meal embellishment products such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including recipe mixes for salad, sold as a finished product or as an ingredient within a product, whether dehydrated, liquid or frozen.
"Beverage Category" means beverages, beverage mixes, and concentrates including, but not limited to, alcoholic and non-alcoholic beverages, ready to drink and dry powdered beverages, carbonated and non-carbonated beverages, e.g., sodas, fruit or vegetable juices.
Homogenized Formulations Also disclosed herein are methods for preparing a homogenized formulation that comprises providing a pre-homogenized composition comprising one or more delivery devices (e.g., microcapsules) and homogenizing the composition. In these methods, the delivery devices are present in the pre-homogenized composition prior to homogenization. Thus, when the pre-homogenized composition undergoes homogenization, as disclosed herein, the delivery devices are present during and subjected to the homogenization process. Further, in many examples disclosed herein the homogenized formulations are further processed (e.g., pasteurized/sterilized).
Thus, the disclosed homogenized formulations can also be pasteurized or sterilized formulations.
In many examples, the disclosed homogenized formulations can be incorporated into (e.g., used to prepare) many of the food articles disclosed herein. For example, disclosed herein are combinations of food articles and homogenized formulations.
In the disclosed homogenized formulations, the amount of delivery devices in a homogenized formulation can be at least 50% of the amount of delivery devices in a pre-homogenized composition. In other examples, the amount of delivery devices in a homogenized formulation can be at least about 55, 60, 65, 70, 75, 80, 85, 90, 95, 97, 98, or 99% of the amount of delivery devices in a pre-homogenized composition, where any of the stated values can form an upper or lower endpoint of a range. The amount of delivery devices in the disclosed homogenized formulations and pre-homogenized compositions can be determined by methods known in the art (for example, see the Examples disclosed herein).
The disclosed homogenized formulations and methods have certain advantages over many existing compositions. For example, by having delivery devices present in the "crude" starting material (i.e., prior to homogenization and, in some cases, prior to other processing techniques such as pasteurization or sterilization), a plant's existing processing streams can be used, thus avoiding costly. modifications to most existing designs where pasteurization is performed directly before or after homogenization. Another advantage is that the delivery devices are subjected to the homogenization process (and, in other examples, pasteurization and sterilization processes as well). This can avoid regulatory issues that surround methods where delivery devices (or other additives) are added after pasteurization/sterilization, which usually require that the product be re-pasteurized or re-sterilized.
Further advantages of certain homogenized formulations (e.g., dairy formulations) and methods disclosed herein can include a narrower particle size distribution of the delivery devices in the homogenized formulations as compared to formulations where the delivery devices were added after homogenization and thus not homogenized.
Also, when the homogenized formulations are pasteurized, as is typically done for dairy products, milk proteins can assemble around the outer shell of the delivery devices during, pasteurization. The degree and amount of assembly is believed to be dependent on the time and temperature of pasteurization. The assembly of the milk proteins (e.g., whey proteins and caesins) can improve the flavor of the formulation, since such proteins are known to be good adsorbers of certain flavors and odors. Also, the associated milk proteins can provide further stability to the delivery devices and their contents.
In the disclosed methods, the pre-homogenized composition can be any fluid that is to be homogenized. Thus, the disclosed methods are not intended to be limited in any way by the particular pre-homogenized compositions. For example, the pre-homogenized composition can be any comestible, cosmetic, pharmaceutical, nutritional, or health care product that is to be homogenized. In certain specific examples, the pre-homogenized composition can be a dairy product (e.g., milk).
It is understood that suitable pre-homogenized compositions can have already been homogenized one or more times before. As long as these compositions are to be homogenized at least once again, they are acceptable pre-homogenized compositions for the disclosed methods.
The pre-homogenized can also be either pasteurized or un-pasteurized. For example, a dairy composition that is pasteurized, but has yet to be homogenized, is a suitable pre-homogenized composition. Also, a dairy composition that has yet to be either homogenized or pasteurized (in any order) is a suitable pre-homogenized composition.
The disclosed pre-homogenized compositions, as well as the resulting homogenized formulations and food articles provided therefrom, can comprise one or more delivery devices, as described herein. In some examples the disclosed pre-homogenized compositions and resulting homogenized formulations can comprise the same type of delivery devices and, in other examples, different types of delivery devices (e.g., microcapsules containing different loading substances).
Some specific examples of homogenized formulations discldsed herein comprise microcapsules having about 130 mg of DHA per gram of microcapsule (e.g., a microcapsule wherein the loading substance comprises a 5:25 oil derived from tuna and/or bonito) and the outer shell of the microcapsules comprises pork or fish gelatin. In another specific example, the homogenized formulations disclosed herein comprise a microcapsule having about 150 mg of DHA and EPA per gram of microcapsule (e.g., a microcapsule wherein the loading substance comprises a 18:12 oil derived from sardine andlor anchovy) and the outer shell of the microcapsules comprises pork or fish gelatin.
Any of these formulations can be infant formula, milk, or yogurt formulations for example.
Any of the disclosed delivery devices can be added to any of the disclosed pre-homogenized compositions. The particular method of addition will depend on the particular pre-homogenized composition, the particular delivery devices, the homogenized composition, including its end use and methods and apparatus of preparation, as well as preference. The disclosed methods are not intended to be limited by, any particular method of adding microcapsules to the pre-homogenized composition.
In some example, the delivery devices are manually added or poured into the pre-homogenized composition (or added to a homogenized composition that is to be homogenized again). In other example, the delivery devices or solutions thereof can be pumped into the pre-homogenized compositions or added via a hopper. Other suitable methods of adding the delivery devices into the pre-homogenized composition are known in the art. Further, mixing can be also be desired in order to fully incorporate the delivery devices into the pre-homogenized compositions. Such mixing can also be accomplished by methods known in the art such as, but not limited to, mechanical stirrers, magnetic stirrers, shakers, bubbling gas, sonication, vortexing, and the like.
The particular amount of delivery devices that can be present in the pre-homogenized compositions will depend on the preference and the particular end use of the homogenized formulations. For example, if one desires or requires a particular amount delivery devices in the homogenized formulations disclosed herein, then about the same amount can be present in or added to the pre-homogenized compositions.
Specific examples of amounts of delivery devices in homogenized dairy formulations, for example, can be from about 0.005% to about 25%, from about 0.01% to about 20%, from about 0.05% to about 18%, from about 0.1% to about 16%, from about 1% to about 10%, by weight of the total composition. Other examples can include formulations containing from about 0.005 to about 5%, from about 0.01 to about 5%, or from about 0.1 to about

5% delivery devices by weight of the total composition. In still other examples, the disclosed homogenized formulations can contain about 0.005, 0.01, 0.05, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21,. 22, 23, 24, or 25% delivery devices by weight of the total composition, where any of the stated values can form an upper or lower endpoint when appropriate.
In the disclosed methods, the pre-homogenized compositions are homogenized.
Any homogenization technique and apparatus known in the art can be used in the disclosed methods. Such homogenization techniques and apparatuses are commonly used in, for example, the food, dairy, phanmaceutical, cosmetic, and fragrance industries.
Many suitable homogenizers are commercially available. Homogenization can involve the use of sonication, pressure, and/or mechanical devices to homogenize the fluid. For example, the homogenization can be a single stage homogenization, a multi-step or multi-stage homogenization (e.g., a two-stage homogenization), a high pressure homogenization (e.g., single or multi-stage high pressure homogenizations), a very-high pressure homogenization, a rotator-stator homogenization, a blade homogenization, and the like.
In some examples, the liomogenization step can be a pressure-based homogenization technique operating at pressures of from about 200 to about 15,000 psi, from about 500 to about 12,000 psi, from about 1,000 to about 9,000 psi, or from about 3,000 to about 6,000 psi. In still other examples, the homogenization step can be performed at about 200, 500, 1000, 1500, 2000, 2500, 3000, 3500, 4000, 4500, 5000, 5500, 6000, 6500, 7000, 7500,. 8000, 8500, 9000, 9500, 10000, 10500, 11000, 11500, or 12000, 12500, 13000, 13500, 14000, 14500, 15000, where any of the stated values can forin an upper or lower endpoint. It is further contemplated that multiple passes of homogenization at any of these pressures can be used, including combinations thereof.
After homogenization, the disclosed homogenized formulations can undergo further processing. For example, the homogenized formulations can be sterilized or pasteurized. Examples of typically pasteurization conditions are high temperature short time pasteurization (HTST), ultra pasteurization (UP), and ultra high temperature (UHT) pasteurization. The homogenized formulations can also be fiuther processed after homogenization by, e.g., the addition of additives, further formulation into the final product, packaged, spray dried, etc. In some examples, the homogenized formulations can be steam injected. Steam injection is a known technique that is sometimes used in the dairy industry. Generally, steam is injected into the milk to remove odors produced when the moisture is flashed off during pasteurization. This process is typically used on milks that are UHT pasteurized.
It is also contemplated that the pre-homogenized compositions comprising one or more microcapsules can be processed prior to homogenization. For example, such pre-homogenized compositions comprising one or more microcapsules can first be sterilized or pasteurized and then homogenized. Likewise, the pre-homogenized compositions comprising one or more microcapsules can be subject to other processing steps prior to homogenization (e.g., the addition of additives, etc.).
The disclosed homogenized formulations have many and varied uses. Any current use of a homogenized fluid can also be suitable for the disclosed homogenized formulations. For comestible formulations, the homogenized formulations disclosed herein can generally be taken orally and can be in any form suitable for oral administration. For example, the homogenized formulation can be spray dried and then fonned into a tablet or provided in a sachet. Alternatively, the homogenized formulations can be incorporated into gel-caps, capsules, liquids, syrups, ointments, lotions, creams, gels, or drops.
The homogenized fonnulations can also be designed for humans or animals, based on the recommended dietary intake for a given individual. Such considerations are generally based on various factors such as species, age, and sex as described above, which are known or can be determined by one of skill in the art. In one example, the disclosed formulations can be used as a component of feed for animals such as, but not limited to, livestock (e.g., pigs, chickens, cows, goats, horses, and the like), and domestic pets (e.g., cats, dogs, birds, and the like).
The disclosed homogenized formulations can also include additional carriers, as well as flavorings, thickeners, diluents, buffers, preservatives, surface active agents, emulsifiers, dispersing aids, or binders and the like in addition to the microcapsules disclosed herein.
Other examples of homogenized formulations or products derived therefrom than can be prepared by the methods disclosed herein include fresb/pasteurized milk, full fat fresh/pasteurized milk, semi skimmed fresh/pasteurized milk, long-life/UHT
milk, full fat long life/LJHT milk, semi skimmed long life/UHT milk, fat-free long life/UHT
milk, goat milk, condensed/evaporated milk, plain condensed/evaporated milk, flavored, functional and other condensed milk, flavored milk drinks, dairy only, flavored milk drinks, flavored milk drinks with fruit juice, soy milk, sour milk drinks, fermented dairy drinks, coffee whiteners, powder milk, flavored powder milk drinks, cream, cheese, processed cheese, spreadable processed cheese, unspreadable processed cheese, unprocessed cheese, spreadable unprocessed cheese, hard cheese, packaged hard cheese, unpackaged hard cheese, yogurt, plain/natural yogurt, flavored yogurt, fruited yogurt, probiotic yogurt, drinking yogurt, regular drinking yogurt, probiotic drinking yogurt, chilled snacks, fromage frais and quark, plain fromage frais and quark, flavored fromage frais and quark, and kifer.
Alternatively, the disclosed homogenized formulations can be prepared in a powdered form (e.g., via spray drying or dehydration) and contained in articles such as sachets or shakers, which can be used to pour or sprinkle the disclosed compositions onto and into food and beverages. Still other examples include baked goods (e.g., breads, rolls, cookies, crackers, fruit pies, or cakes), pastas, condiments, salad dressings, soup mixes, snack foods, processed fruit juices, sauces, gravies, syrups, beverages, dry beverage powders, jams or jellies, or pet companion food that have been prepared with a homogenized formulation as disclosed herein.
Deliver_yDevices Examples of delivery devices that can be used in the disclosed food articles and methods include, but are not limited to, microcapsules, microspheres, nanospheres or nanoparticles, liposomes, noisome, emulsions, or powders.
Loading substances, as are described more fully herein, can be incorporated into Liposomes. As is known in the art, liposomes are generally derived from phospholipids or other lipid substances. Liposomes are formed by mono- or multi-lamellar hydrated liquid crystals that are dispersed in an aqueous medium. Any non-toxic, physiologically acceptable and metabolizable lipid capable of forming liposomes can be used.
The liposome can also contain stabilizers, preservatives, excipients, and the like. Examples of suitable lipids are the phospholipids and the phosphatidyl cholines (lecithins),, both natural and synthetic. Methods of forming liposomes are known in the art. See e.g., Prescott, Ed., Methods in Cell Biology, Volume XIV, Academic Press, New York, p. 33 et seq., 1976, which is hereby incorporated by reference herein for its teachings of liposomes and their preparation. In other examples, the liposomes can be cationic liposomes (e.g., DOTMA, DOPE, DC cholesterol) or anionic liposomes.
As described herein, niosomes are delivery devices that can be used to deliver a loading substance as disclosed herein. Noisomes are multilamellar or unilamellar vesicles involving non-ionic surfactants.
Solid-lipid nanoparticles, as described herein, are other delivery devices that can be used to deliver a loading substance as disclosed herein. Solid-lipid nanoparticles are nanoparticles, which are dispersed in an aqueous surfactant solution. They are comprised of a solid hydrophobic core having a monolayer of a phospholipid coating and are usually prepared by high-pressure homogenization techniques.

Microcapsules Microcapsules, as described herein, are yet further examples of delivery devices that can be used in the disclosed food articles and methods as disclosed herein. In contrast to liposomal delivery systems, microcapsules (including microspheres) typically do not have an aqueous core but a solid polymer matrix or membrane. These delivery devices are obtained by controlled precipitation of polymers, chemical cross-linking of soluble polymers, and interfacial polymerization of two monomers or high-pressure homogenization techniques. The encapsulated compound (i.e., loading substance) is gradually released from the depot by erosion or diffusion from the particles.
Successful formulations of short acting peptides, such as LHRH agonists like leuprorelin and triptoreline, have been developed. Poly(lactide co-glycolide) (PLGA) microspheres are currently used as monthly and three monthly dosage forms in the treatment of advanced prostrate cancer, endometriosis, and other hormone responsive conditions.
Leuprolide, an LHRH superagonist, was incorporated into a variety of PLGA matrices using a solvent extraction/evaporation method. As noted, all of these delivery devices can be used in the food articles and methods disclosed herein.

The use of microcapsules can protect certain compositions from oxidation and degradation, keeping the loading substance fresh. Also, because microcapsules can hide the unpleasant odor or taste of certain compositions, the food articles and methods disclosed herein can be particularly useful for delivering and supplementing unpleasant compositions. Still further, the use of microcapsules can allow various loading substances to be added to food articles which are otherwise not amenable to supplementation. For example, omega-3 fatty acids can degrade or oxidize in air and can be sensitive to food preparation techniques (e.g., baking). By the use microencapsulated omega-3 fatty acids, these compositions can be added to food without significant degradation during food preparation.
Microcapsules that are suitable for use in the disclosed food articles are defined as small particles of solids, or droplets of liquids, inside a thin coating of a shell material such as beeswax, starch, gelatine, or polyacrylic acid. They are used, for example, to prepare liquids as free-flowing powders or compressed solids, to separate reactive materials, to reduce toxicity, to protect against oxidation and/or to control the rate of release of a substance such as an enzyme, a flavor, a nutrient, a drug, etc.
Over the past fifty years, much focus has been on so-called "single-core"
microcapsules. However, one of the problems with single-core microcapsules is their susceptibility to rupture. To increase the strength of microcapsules, the thickness of the microcapsule wall can be increased. However, this can lead to a reduction in the loading capacity of the microcapsule. Another approach has been to create so-called "multi-core"
microcapsules. For example, U.S. Pat. No. 5,780,056 discloses a "multi-core"
microcapsule having gelatine as a shell material. These microcapsules are formed by spray cooling an aqueous emulsion of oil or carotenoid particles such that the gelatine hardens around "cores" of the oil or carotenoid particles. Yoshida et al.
(Chemical Abstract 1990:140735 or Japanese Patent Publication JP 01-148338) discloses a complex coacervation process for the manufacture of microcapsules in which an emulsion of gelatine and paraffin wax is added to an arabic rubber solution and then mixed witll a surfactant to form "multi-core" microcapsules. Ijichi et al. (J. Ghein. Eng.
Jpn. (1997) 30(5):793-798) micoroencapsulated large droplets of biphenyl using a complex coacervation process to form multi-layered microcapsules. U.S. Pat. Nos.
4,219,439 and 4,222,891 disclose "multi-nucleus," oil-containing microcapsules having an average diameter of about 3 to about 20 m with an oil droplet size of about 1 to about 10 m for use in pressure-sensitive copying papers and heat sensitive recording papers.
Particularly suitable microcapsules include those that are resistant to rupture during the preparation of the food article (including packaging, transportation, and storage of the food article). In some examples, the microcapsules can be of a size and consistency that does not detract from the texture and constitution of the food article.
Microcapsules suitable for use in the disclosed articles and methods can be any microcapsule as disclosed herein. In specific examples, the microcapsules can comprise an agglomeration of primary microcapsules and a loading substance. Each individual primary microcapsule has a primary shell. The loading substance is encapsulated by the primary shell and the agglomeration is encapsulated by an, outer shell. These microcapsules are referred to herein as "multicore microcapsules." In another example, described herein are microcapsules that comprise a loading substance, a primary shell, and a secondary shell, wherein the primary shell encapsulates the loading substance and the secondary shell encapsulates the composition and primary shell. These microcapsules are referred to herein as "single-core microcapsules." Unless stated otherwise, the term "microcapsule" is used herein to refer to multicore, single-core, or a mixture of multicore and single-core microcapsules. Particularly suitable microcapsules are disclosed in US
Patent Nos. 6,974,592 and 6,969,530 and US Publication No. 2005-0019416-Al, which are all incorporated by reference herein in their entireties for at least their disclosures of microcapsules, their methods of preparation, and their methods of use.
The microcapsules disclosed herein generally have a combination of high payload and structural strength. For example, the disclosed microcapsules are strong enough to survive the homogenization process. Further, the payloads of loading substances in the disclosed microcapsules can be from about 20% to about 90%, about 50% to about 70%
by weight, or about 60% by weight of the microcapsule. In other examples, the disclosed microcapsules can contain about 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90% by weight of the microcapsule, where any of the stated values can form an upper or lower endpoint when appropriate.
It is also contemplated that one or more additional shell layers can be placed on the outer shell of the microcapsules. The techniques described in International Publication No. WO 2004/041251 Al, which is incorporated by reference in its entirety, can be used to add additional shell layers to the microcapsules.

A number of different polyniers can be used to produce the shell layers of the single-core and multicore microcapsules. For example, the primary shell and/or outer shell material of the disclosed microcapsules can comprise a surfactant, gelatin, protein, polyphosphate, polysaccharide, or mixtures thereof. Further examples of suitable materials for the primary shell and/or outer shell include, but are not limited to, gelatin type A, gelatin type B, polyphosphate, gum arabic, alginate, chitosan, carrageenan, pectin, starch, modified starch, alfa-lactalbumin, beta-lactoglobumin, ovalbumin, polysorbiton, maltodextrin, cyclodextrin, cellulose, methyl cellulose, ethyl cellulose, hydropropy.lmethylcellulose, carboxymethylcellulose, milk protein, whey protein, soy protein, canola protein, albumin, chitin, polylactides, poly-lactide-co-glycolides, derivatized chitin, poly-lysine, kosher gelatin, non-kosher gelatin, Halal gelatin, and non-Halal gelatin, including combinations and mixtures thereof. It is also contemplated that derivatives of these polymers can be used as well. One specific type of primary shell and/or outer shell material that can be used in the disclosed microcapsules is. fish gelatin or pork gelatin.
In many examples of suitable microcapsules, the primary shell and/or outer shell material can have a Bloom number of from about 0 to about 350. The Bloom number describes the gel strength formed at 10 C with a 6.67% solution gelled for 18-hours.
Determining the Bloom number of a substance can be accomplished by methods known in the art. It is contemplated that the primary, shell and/or outer shell material can have a Bloom number of about 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 491 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 70, 71, 72, 73, 74, 75, 76, 7'7, 78, 79, 80, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 140, 141, 142, 143, 144, 145, 146, 147; 148, 149, 150, 150, 151, 152, 153, 154, 155, 156, 157,158,159,160,160,161,162,163,164,165,166,167,168,169,170,170,171,172, 173, 174, 175, 176, 177, 178, 179, 180, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 220, 22 1, 222, 223, 224, 225, 226, 227, 228, 229, 230, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 250, 251, 252, 253, 254, 255, 256, 2'57, 258, 259, 260, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 320, 321, 322, 323, 324, 325, 326, 327, 328, 329, 330, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, or 350, where any of the stated values can form an upper or lower end point where appropriate.
In some specific examples the primary and/or outer shell material can have a Bloom number of from about 0 to about 50, and in other examples the primary and/or outer shell material can have a Bloom number of from about 51 to about 350. Still other specific examples include microcapsules comprising a primary shell and/or outer shell material having a Bloom number of about 0, about 210, about 220, or about 240. In one example, the microcapsule does not contain "low Bloom" gelatine, which is gelatin having a Bloom number less than 50.
The shell material can be a two-component system made from a mixture of different types of polymer components. In other examples, the shell material can be a complex coacervate between two or more polymer components (e.g., gelatine A
and polyphosphate). Component A can be gelatine type A, although other polymers like those mentioned above for the shell materials are also contemplated as component A.
Component B can be gelatine type B, polyphosphate, gum arabic, alginate, chitosan, carrageenan, pectin, carboxymethyl-cellulose or a mixture thereof. Again other polymers like those disclosed above for the shell materials are also contemplated as component B.
The molar ratio of component A: component B that is used depends on the type of components but is typically from about 1:5 to about 15:1. For example, when gelatine type A and polyphosphate are used as components A and B respectively, the molar ratio of component A:component B can be about 8:1 to about 12:1; when gelatine type A and gelatine type B are used as components A and B respectively, the molar ratio of component A:component B can be about 2:1 to about 1:2; and when gelatine type A and alginate are used as components A and B respectively, the molar ratio of component A:component B can be about 3:1 to about 5:1. In many of the disclosed microcapsules the primary shell and/or outer shell can comprise a complex coacervate. For example, the primary shell and/or outer shell can comprise a complex coacervate of gelatin and polyphosphate.

In the disclosed microcapsules the outer shell can have an average diameter of from about 1 m to about 2,000 m, from about 20 m to about 1,000 gm, or from about 30 m to about 80 m. In further examples, the average diameter of the outer shell can be about 1, 10, 20, 30, 40, 50, 60, 70, 80, 90, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, or 2000 m, where any of the stated values can form an upper or lower endpoint when appropriate.
The primary shells of the disclosed microcapsules can have an average diameter of from about 40 nm to about 10 m or from about 0.1 m to about 5 m. In fixrther examples, the average diameter of the primary shell can be about 40 nm, 50 nm, 60 nni, 70 nm, 80 nm, 90 nm, 100 nm, 200 nm, 300 nm, 400 nm, 500 nm, 600 nm, 700 nm, nm, 900 nm, 1000 nm, 2 m, 3 gm, 4 m, 5 m, 6 m, 7 m, 8 m, 9 .m, 10 m, where any of the stated values can form an upper or lower endpoint when appropriate.
Particle size can be measured using any typical equipment known in the art, for example, a Coulter LS230 Particle Size Analyzer, Miami, Florida, USA.

Loading Substances In the disclosed delivery devices, the loading substance can be any substance that one desires to be delivered to a subject. In many examples, a suitable loading substance is not entirely soluble in an aqueous mixture. The loading substance can be a solid, a hydrophobic liquid, or a mixture of a solid and a hydrophobic liquid. In many of the examples herein, the loading substance can comprise a long chain polyunsaturated fatty acid, specific examples of which are included below. Further, the loading substance can comprise a biologically active substance, a nutrient such as a nutritional supplement, a flavoring substance, a polyunsaturated fatty acid like an omega-3 fatty acid, a vitamin, a mineral, a carbohydrate, a steroid, a trace element, andfor a protein, and the like including mixtures and combinations thereof. In other examples, the loading substance can comprise microbial oil, algal oil (e.g., oil from a dinoflagellate such as Crypthecodinium cohnii), fungal oil (e.g., oil from Tlaraustochytrium, Schizoclaytrium, or a mixture thereof), and/or plant oil (e.g., flax, vegetables), including mixtures and combinations thereof. In other examples, the loading substance can be a phannaceutical composition (e.g., a drug and/or an enzyme) or a flavor. The loading substance can also be a hydrophobic liquid, such as grease, oil or a mixture thereof. Typical oils can be fish oils, vegetable oils (e.g., canola, olive, corn, rapeseed), mineral oils, derivatives thereof or mixtures thereof. The loading substance can comprise a purified or partially purified oily substance such as a fatty acid, a triglyceride, or a mixture thereof.

In still other examples, a suitable loading substance can comprise marine oil, such as natural and refined and concentrated fish oil. Examples of suitable fish oils include, but are not limited to, Atlantic fish oil, Pacific fish oil, Mediterranean fish oil, light ?ressed fish oil, alkaline treated fish oil, heat treated fish oil, light and heavy brown fish ail, bonito oil, pilchard oil, tuna oil, sea bass oil, halibut oil, spearfish oil, barracuda oil, 3od oil, menhaden oil, sardine oil, anchovy oil, capelin oil, Atlantic cod oil, Atlantic herring oil, Atlantic mackerel oil, Atlantic menhaden oil, salmonid oil, and shark oil, including mixtures and combinations thereof. Non-alkaline treated fish oil is also a, suitable loading substance. Other marine oils suitable for use herein include, but are not limited to, squid oil, cuttle fish oil, octopus oil, krill oil, seal oil, whale oil, and the like, including mixtures and combinations thereof. Any marine oil and combination of marine oil can be used in the disclosed delivery devices and in the disclosed food articles and methods.
Many of the microbial, algal, fi.ingal, plant, and marine oils disclosed herein contain omega-3 fatty acids. As such, certain delivery devices disclosed herein can contain a loading substance that comprises an omega-3 fatty acid, an alkyl ester of an omega-3 fatty acid, a triglyceride ester of an omega-3 fatty acid, a phy_tosterol ester of an omega-3 fatty acid, and/or mixtures and combinations thereof. An omega-3 fatty acid is an unsaturated fatty acid that contains as its terminus CH3-CH2-CH=CH-.
Generally, an omega-3 fatty acid has the following formula:

(I
CH3 CH2-CH=CH-R~-C OR2 wherein R' is a C3-C40 alkyl or alkenyl group comprising at least one double bond and R2 is H or alkyl group. The term "alkane" or "alkyl" as used herein is a saturated hydrocarbon group (e.g., methyl, ethyl, n-propyl, isopropyl, ra-butyl, isobutyl, s-butyl, t-butyl, yi-pentyl, isopentyl, s-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like). The term "alkene"
or "alkenyl" as used herein is a hydrocarbon group containing at least one carbon-carbon double bond.
Asymmetric structures such as (AB)C=C(CD) are intended to include both the E
and Z
isomers (cis and traris). In a fiuther example, Rl can be a C5-C38, C6-C36, C8-C342 Cio-C32~, C12-C30, C14-C28, C16-C26a or C18-C24 alkenyl group. In yet another example, the allcenyl group of R' can have from 2 to 6, from 3 to 6, from 4 to 6, or from 5 to 6 double bonds.

Still further, the alkenyl group of Rl can have from 1, 2, 3, 4, 5, or 6 double bonds, where any of the stated values can form an upper or lower endpoint as appropriate.
Specific examples of omega-3 fatty acids that are suitable loading substances that can be used in the disclosed delivery devices include, but are not limited to, a-linolenic acid (18:3cv3), octadecatetraenoic acid (18:40), eicosapentaenoic acid (20:5w3) (EPA), eicosatetraenoic acid (20:4w3), henicosapentaenoic acid (21:5w3), docosahexaenoic acid (22:6w3) (DHA), docosapentaenoic acid (22:5w3) (DPA), including derivatives and mixtures thereof. Many types of fatty acid derivatives are well known to one skilled in the art. Examples of suitable derivatives are esters, such as phytosterol esters, furanoid esters, branched or unbranched Cl-C30 alkyl esters, branched or unbranched C2-alkenyl esters or branched or unbranched C3-C30 cycloalkyl esters, in particular phytosterol esters and CI-C6 alkyl esters. In a further example, the loading substance can be a phytosterol ester of docosahexaenoic acid and/or eicosapentaenoic acid, a alkyl ester of docosahexaenoic acid and/or eicosapentaenoic acid, a triglyceride ester of docosahexaenoic acid and/or eicosapentaenoic acid, and/or a mixture thereof.
Other examples of suitable loading substances that can be present in the disclosed delivery devices comprise at least 4, at least 6, at least 8, at least 10, at least 12, at least 14, at least 16, at least 18, or at least 20 carbon atoms. In some other examples, the loading substance can contain about 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, or 45 carbon atoms, where any of the stated values can form an upper or lower endpoint when appropriate. In still other examples, the loading substance can comprise a mixture of fatty acids (including derivatives thereof}. having a range of carbon atoms. For example, the loading substance can comprise from about 8 to about 40, from about 10 to about 38, from about 12 to about 36, from about 14 to about 34, from about 16 to about 32, from about 18 to about 30, or from about 20 to about 28 carbon atoms.
Some further examples of loading substances are those that contain at least one unsaturated bond (i.e., a carbon-carbon double or triple bond). For example, the loading substance can contain at least 2, at least 3, at least 4, at least 5, at least

6, at least 7, or at least 8 carbon-carbon double bonds, triple bonds, or any combination thereof.
In another example, the loading substance can comprise 1, 2, 3, 4, 5, 6, 7, or 8 unsaturated bonds, where any of the stated values can form an upper or lower endpoint as appropriate.

Some specific examples of loading substances, which are unsaturated fatty acids, are shown in the following tables. Derivatives of these fatty acids are also suitable and are thus contemplated herein.

Table 1: Examples of Monoene Acids Total number of Carbon number where double bond begins.
carbon atoms in the ("c" denotes a cis double bond; "t" denotes a trans double fatty acid chain bond) 4c 12 4c 14 4cand9c 16 3t, 4c, 5t, 6c, 6t, 9c (palmitooleic), and l lc 18 3t, 5c, 5t, 6c (petroselinic), 6t, 9c (oleic), lOc, l lc (cis-vaccenic), l lt (vaccenic), and 13c 5c, 9c (gadolenic), l lc, 13c, and 15c 22 5c, 11c (cetoleic), 13c (erucic), and 15c 24 15c (selacholeic, nervonic) 26 9c, and 17c (ximenic) 28 9c, 19c (lumequic) 21c Unsaturated fatty acids that contain at least one pair of methylene interrupted unsaturated bonds are also suitable loading substances. By "methylene interrupted unsaturated bond" is meant that one carbon-carbon double or triple bond is separated from another carbon-carbon double or triple bond by at least one methylene group (i.e., CHa). Specific examples of such loading substances include, but are not limited to, the n-1 family derived from 9, 12, 15-16:3; n-2 family derived from 9, 12, 15-17:3, 15:3, 17:3, 17:4, 20:4; n-3 family derived from 9, 12, 15-18:3, 15:2, 15:3, 15:4, 16:3, 16:4, 18:3 (a-linolenic), 18:4, 18:5, 20:2, 20:3, 20:4; 20:5 (EPA), 21:5, 22:3, 22:5 (DPA), 22:6 (DHA), 24:3, 24:4, 24:5, 24:6, 26:5, 26:6, 28:7, 30:5; n-4 family derived from 9,12-16:2, 16:2, 16:3, 18:2, 18:3; n-5 family derived from 9, 12-17:2, 15:2, 17:2, 17:3,19:2, 19:4, 20:3, 20:4 21:4, 21:5; n-6 family derived from 9, 12-18:2, 15:2,16:2,18:2 (linoleic acid), 18:3 (y-linolenic acid); 20:2, 20:3, 20:4 (arachidonic acid), 22:2, 22:3, 22:4 (adrenic acid), 22:5, 24:2, 24:4, 25:2, 26:2, 30:4; n-7 family derived from 9-16:1, 15:2, 16:2, 17:2, 18:2, 19:2; n-8 family derived from 9-17:1, 15:2, 16:2, 17:2, 18:2, 19:2; n-9 family derived from 9-18:1, 17:2,18:2, 20:2, 20:3, 22:3, 22:4; n-11 family 19:2, and the n-12 family 20:2. In one particular specific example, the loading substance can comprise arachidonic acid.
In the above paragraph (and throughout) the compounds are identified by referring first to the "n-x family," where x is the position in the fatty acid where the first double bond begins. The numbering scheme begins at the terminal end of the fatty acid, where, for example, the terminal CH3 group is designated position 1. In this sense, the n-3 family would be an omega-3 fatty acid, as described above. The next number identifies the total number of carbon atoms in the fatty acid. The third number, which is after the colon, designates the total number of double bonds in the fatty acid. So, for example, in the n-1 family, 16:3, refers to a 16 carbon long fatty acid with 3 double bonds, each separated by a methylene, wherein the first double bond begins at position 1, i.e., the terminal end of the fatty acid. In another example, in the n-6 family, 18:3, refers to an 18 carbon long fatty acid with 3 methylene separated double bonds beginning at position 6, i.e., the sixth carbon from the terminal end of the fatty acid, and so forth.
Further examples of loading substances that contain at least one pair of methylene interrupted unsaturated bonds are shown in Table 2.

Table 2: Examples of Polyene Acids Total number of Carbon number where double bond begins.
carbon atoms in the ("c" denotes a cis double bond; "t" denotes a trans fatty acid chain double bond) 5, 9 5, 11 2t, 9, 12 3t, 9, 12 18 5t,9,12 5, 9, 12 5, 11, 14 3t, 9, 12, 15 5,9,12,15 5, 11 5, 13

7, 11 20 7,13 5, 11, 14 7, 11, 14 5,11,14,17 5,11 5,13 7,13 22 7,15 7, 17 9, 13 9, 15 Specific examples of suitable loading substances that contain conjugated unsaturated bonds include, but are not limited to, those in Table 3. By "conjugated unsaturated bond" is meant that at least one pair of carbon-carbon double and/or triple bonds are bonded together, without a methylene (CH2) group between them (e.g., CH=CH-CH=CH ).

Table 3: Examples of Conjugated Polyene Acids Total number of Carbon number where double bond begins.
carbon atoms in the ("c" denotes a cis double bond; "t" denotes a trans double fatty acid chain. bond) 2t, 4t, 6c 2c, 4t, 6t 3t, 5t, 7c 3c, 5t, 7t 12 3,5,7,9,11 14 3, 5, 7, 9, 11 lOt, 12t 8c, lOt, 12c (jacaric) 8t, lOt, 12c (calendic) 8t, lOt, 12t 9t, l lt, 13c (catalpic) 9c, l lt, 13t (a-eleostearic) 9c, l lt, 13c (punicic) 9t, 11t, 13t ((3-eleostearic) 9c, 11t, 13t, 15c (a-parinaric) 91, 11t, 13t, 15t ((3-parinaric) In the above examples of suitable loading substances, derivatives of the disclosed loading substances can also be used. By "derivatives" is meant the ester of a fatty acid (e.g., methyl and ethyl esters), salts of the fatty acids (e.g., sodium and potassium salts}, and triglycerides, diglycerides, and monoglycerides, sterol esters, antioxidant-oil conjugates (e.g., ascorbyl palmitate), and naturally derivatives such as furanoid fatty acid derivatives.
The loading substances disclosed herein can also be crude oils, semi-refined (also called alkaline refined), or refined oils from such sources disclosed herein.
Still further, the disclosed compositions and methods can use oils comprising re-esterified triglycerides.
It is contemplated herein that one or more of the disclosed loading substances can be used. For example the disclosed delivery devices can contain two or more different loading substances. Further, the loading substance can be present in an amount of from about 1% to about 50% by weight of a microcapsule. In specific examples, the loading substance can be present in an amount of from about 1% to about 40%, from about 1% to about 30%, from about 1% to about 20%, from about 1% to about 15%, or from about 1%
to about 10% by weight of a microcapsule.
In one example, the loading substance is not a fatty acid conjugate. A fatty acid conjugate is a fatty acid that has been coupled to (e.g., bonded to) another chemical moiety, such as a metal (e.g., chromium) or cofactor (CoQ1o).
In one example, the loading substances can contain an antioxidant. Suitable examples of antioxidants include, but are not limited to, a phenolic compound, a plant extract, or a sulfur-containing compound. In certain examples disclosed herein the antioxidant can be ascorbic acid or a salt thereof, e.g., sodium ascorbate. In other examples, the antioxidant can be citric acid or a salt thereof. In still other examples, the antioxidant can be vitamin E, CoQlo, tocopherols, lipid soluble derivatives of more polar antioxidants such as ascobyl fatty acid esters (e.g., ascobyl palmitate), plant extracts (e.g., rosemary, sage and oregano oils), algal extracts, and synthetic antioxidants (e.g., BHT, TBHQ, ethoxyquin, alkyl gallates, hydroquinones, tocotrienols).
The disclosed loading substance can also contain other nutrient(s)- such as vitamins other trace elements, minerals, and the like. Further, the loading substances can comprise other components such as preservatives, antimicrobials, anti-oxidants, chelating agents, thickeners, flavorings, diluents, emulsifiers, dispersing aids, or binders, including any mixture thereof.
Specific Examples Specific examples of suitable delivery devices include microcapsules that contain any of the shell materials and any of the loading substances disclosed herein.
Some 3pecific examples include, but are not limited to, microcapsules where the shell materials are coniplex coacervates, e.g., coacervates of gelatin and polyphosphate. The shell material can, in certain examples, comprise gelatin with a Bloom number of from about 0 'o about 50. Loading substances that can be used can, in many instances, include marine :)ils (e.g., fish oils and algal oils). Loading substances that comprise omega-3 fatty acids such as EPA and DHA can also be desirable. Further, derivatives of omega-3 fatty acids, such as mono-, di-, and triglycerides, alkyl esters, sterol esters, antioxidant esters (e.g., ascorbyl and citryl esters), and fiuanoid esters, can also be suitable loading substances.
Some particularly suitable microcapsules include microcapsules containing fish oils. Examples of such fish oils include, but are not limited to, sardine, anchovy, bonito, and/or tuna oil. Fish oils can also be referred to herein by the approximate ratio of EPA
and DHA, or derivatives thereof, found in the oil. For example, 18:12 oils generally comprise a ratio of EPA to DHA (or their triglyceride esters for example) of about 1 S:12.
Likewise, 5:25 oils generally comprise a ratio of EPA to DHA of about 5:25.
Any of these oils can be encapsulated in a complex coacervate comprising and fish or pork gelatin. Such microcapsules can be Generally Regarded as Safe (GRAS), kosher, and/or Halal. Also, such microcapsules can have at least about 130 mg of DHA or at least about 150 mg of EPA and DHA per gram of powder. Further, antioxidants such as ascorbic acid, citric acid, and/or phosphoric acid (or salts thereof) can be present in such microcapsules.
Some specific examples of food articles disclosed herein comprise microcapsules having about 130 mg of DHA per gram of microcapsule (e.g., a microcapsule wherein the loading substance comprises a 5:25 oil derived from tuna and/or bonito) and the outer shell of the microcapsules comprises pork or fish gelatin. In another specific example, a food article disclosed herein can comprise a microcapsule having about 150 mg of DHA
and EPA per gram of microcapsule (e.g., a microcapsule wherein the loading substance comprises a 18:12 oil derived from sardine and/or anchovy) and the outer shell of the microcapsules comprises pork or fish gelatin.
In one instance, the loading substance is not a conjugated fatty acid. In another instance, the microcapsule does not comprise a low Bloom gelatin.
Method of Making Microcapsules Microcapsules prepared by the processes disclosed herein typically have a combination of payload and structural strength that are suitable for the disclosed food articles and methods. In one example, the methods disclosed in U.S. Patent Nos.
6,974,592 and 6,969,530, which are incorporated by reference in their entirety, can be used to prepare microcapsules that can be incorporated into the food articles disclosed herein. It is also contemplated that one or more additional shell layers can be placed on the outer shell of the single-core or multicore microcapsules. In one example, the techniques described in International Publication No. WO 2004/041251 Al, which is incorporated by reference in its entirety, can be used to add additional shell layers to the single-core and multicore microcapsules.
In general, suitable microcapsules can be prepared by a process that comprises providing an emulsion comprising a first polymer component and a loading substance;
adding a second polymer component to the emulsion; adjusting pH, temperature, concentration, mixing speed, or a combination thereof to form an aqueous mixture comprising a primary shell material, wherein the primary shell material comprises the first and second polymer components and surrounds the loading substance;
cooling the aqueous mixture to a temperature above the gel point of the primary shell material until the primary shell material forms agglomerations; and f-urther cooling the aqueous mixture to form an outer shell around the agglomeration.
In these methods, the first polymer component and second polymer component can be the same as any of the primary and outer shell materials described herein. That is, the first and second polymer components can become the primary and/or outer shell materials in the disclosed methods for preparing microcapsules. Furtllermore, any of the loading substances described herein can be used in these methods for preparing microcapsules.

In the disclosed methods, an aqueous mixture of a loading substance, a first polymer component of the shell material, and a second polymer component of the shell material is formed. The aqueous mixture can be a mechanical mixture, a suspension, or an emulsion. When a liquid loading substance is used, particularly a hydrophobic liquid, the aqueous mixture can be an emulsion of the loading substance and the polymer components. In another example, a first polymer component is provided in aqueous solution, together with processing aids, such as antioxidants. A loading substance can then be dispersed into the aqueous mixture, for example, by using a homogenizer. If the loading substance is a hydrophobic liquid, an emulsion is formed in which a fraction of the first polymer component begins to deposit around individual droplets of loading substance to begin the formation of primary shells. If the loading substance is a solid particle, a suspension is formed in which a fraction of the first polynier component begins to deposit around individual particles to begin the formation of primary shells. At this aoint, another aqueous solution of a second polymer component can be added to the iqueou$ mixture.
In the processes for preparing microcapsules disclosed herein, providing an -mulsion of the first polymer component and the loading substance can be accomplished by methods and apparatus known in the art, e.g., homogenization and high pressure/high shear pumps. For example, emulsification can take place by emulsifying at from about 1,000 to about 15,000 rpm. The emulsification step can be monitored by removing a sample of the mixture and analyzing it under such methods as microscopy, light scattering, turbidity, etc. Generally, emulsification can be performed until an average droplet size of less than about 1,000, 750, 500, 100, or 10 nm is obtained.
Not wishing to be bound by theory but it is believed that by varying the emulsification speed it is possible to produce single or multicore microcapsules. For ex.ample, when lower emulsification speeds are used (e.g., 1,000 to 2,000 rpm), the droplets of the loading substance are large enough to form a single particle, which upon encapsulation, produces a single core microcapsule. Conversely, if high emulsification speeds are used (e.g., 5,000 to 15,000 rpm), the resultant droplets of loading substance are usually small (e.g., from 1 to 10 m). These tiny droplets can have higher surface energy and can readily form agglomerations when pH and/or temperature is adjusted accordingly, which results in the formation of multicore microcapsules upon encapsulation. Particle size can be measured using any, typical equipment known in the art, for example, a COULTERTM
LS230 Particle Size Analyzer, Miami, Fla. USA.
The emulsification step can be performed at greater than room temperature, greater than 30, 40, 50, 60, 70, or 80 C, where any of the stated values can form an upper or lower endpoint when appropriate. Specific examples include emulsifying the mixture at from about 30 C to about 60 C or from about 40 C to about 50 C.
It is further contemplated that antioxidants and/or surfactants, which are also described herein, can be added to the aqueous mixture. Such antioxidants and/or surfactants can be added before, during, and/or after the emulsion is provided.
The amount of the polymer components of the shell material provided in the aqueous mixture is typically sufficient to form both the primary shells and the outer shells of the loading agglomeration of microcapsules. The loading substance can be provided in an amount of from about 1% to about 15% by weight of the aqueous mixture, from about 3% to about 8% by weight, or about 6% by weight.
The pH, temperature, concentration, mixing speed, or a combination thereof can be adjusted to form an aqueous mixture comprising a primary shell material, wherein the primary shell material comprises the first and second polymer components and surrounds the loading substance. If there is more than one type of polymer component, complex coacervation will occur between the components to form a coacervate, which further deposits around the loading substance to form primary shells of shell material. The pH
adjustment depends on the type of shell material to be formed. For example, the pH may be adjusted to a value from 3.5 to 5.0, or from 4.0 to 5Ø If the pH of the mixture starts in the desired range, then little or no pH adjustment is required.
The initial temperature of the aqueous mixture can be from about 20 C to about 60 C, or about 30 C to about 50 C.
Mixing can be adjusted so that there is good mixing without breaking the microcapsules as they form. Particular mixing parameters depend on the type of equipment being used. Any of a variety of types of mixing equipment known in the art may be used. In one example, an axial flow impeller, such as LIGHTNIN A310 or A510, can be used.
In many examples disclosed herein, the primary shell and the outer shell of the disclosed microcapsules can comprise a complex coacervate. The complex coacervate can be formed from the first and second polymer components. For example, the primary shell and the outer shell can comprise a complex coacervate between gelatin and polyphosphate. All combinations of first and second polymer components are contemplated herein for the complex coacervate and the primary and outer shell.
The aqueous mixture can then be cooled under controlled cooling rate and mixing parameters to permit agglomeration of the primary shells to form encapsulated agglomerations of primary shells. Not wishing to be bound by theory, the encapsulated agglomerations are discrete particles themselves. It is advantageous to control the formation of the encapsulated agglomerations at a temperature above the gel point of the shell material, and to let excess shell material form a thicker outer shell.
It is also possible at this stage to add more polymer, where the polynier is the same or different as the shell material being used, in order to thicken the outer shell and/or produce microcapsules having primary and outer shells of different composition. The outer shell encapsulates the agglomeration of primary shells to form a rigid encapsulated agglomeration of microcapsules.
Cooling the aqueous mixture can be accomplished by methods known in the art (e.g., the use of a chiller). The rate of cooling can be about 1 C per about 1 to about 100 minutes. For example, the rate of cooling can be about 1 C per about 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 100 minutes, where any of the stated values can form an upper or lower endpoint when appropriate. In specific examples the rate of cooling can be about 1 C/5 minutes. Cooling can take place until the mixture reaches a temperature of from about 5 C to about 10 C, e.g., about 5 C.
Processing. aids can be included in the shell material (e.g., primary and/or outer shells). Processing aids can be used for a variety of reasons. For example, they may be used to promote agglomeration of the primary microcapsules, stabilize the emulsion system, improve the properties of the outer shells, control microcapsule size, and/or to act as an antioxidant. In one aspect, the processing aid can be an emulsifier, a fatty, acid, a lipid, a wax, a microbial cell (e.g., yeast cell lines}, a clay, or an inorganic compound (e.g., calcium carbonate). Not wishing to be bound by theory, these processing aids can improve the barrier properties of the microcapsules. In one aspect, one or more antioxidants can be added to the shell material. Antioxidant properties are usefiil both during the process (e.g., during coacervation and/or spray drying) and in the microcapsules after they are formed (i.e., to extend shelf-life, etc).
Preferably a small number of processing aids that perform a large number of functions can be used. In one aspect, the antioxidant can be a phenolic compound, a plant extract, or a sulphur-containing amino acid. In one aspect, ascorbic acid or citric acid (or a salt thereof such as sodium or potassium ascorbate or sodium or potassium citrate) can be used to promote agglomeration of the primary microcapsules, to control microcapsule size and to act as an antioxidant. The antioxidant can be used in an amount of about 100 ppm to about 12,000 ppm, or from about 1,000 ppm to about 5,000 ppm. Other processing aids such as, for example, metal chelators, can be used as well. For example, ethylene diamine tetraacetic acid can be used to bind metal ions, which can reduce the catalytic oxidation of the loading substance.
In the disclosed microcapsules, the shell material can also be cross-linked.
Thus, the disclosed methods can further involve the addition of a cross-linker. The cross-linker can be added to further increase the rigidity of the microcapsules by cross-linking the shell material in both the outer and primary shells and to make the shells insoluble in both aqueous and oily media. In one example, the cross-linker is added after the outer shell of the microcapsule is produced. Any suitable cross-linker can be used and the choice of cross-linker can vary depending upon the selection of the first and second polymer component. In another example, the cross-linkers can be enzymatic cross-linkers (e.g.
transglutaminase), aldehydes (e.g. formaldehyde or gluteraldehyde), tannic acid, alum or a mixture thereof. In another aspect, the cross-linker can be a plant extract or a phenolic.
It is also contemplated that one or more loading substances (e.g., antioxidants) can be used with the cross-linker. Wlien the microcapsules are to be used in a formulation that is to be delivered to an organism, the cross-linkers are preferably non-toxic or of sufficiently low toxicity. The amount of cross-linker used depends on the components selected and can be adjusted to provide more or less structural rigidity as desired. In one aspect, the amount of cross-linker that can be used is in the amount of about 0.1% to about 5.0%, about 0.5% to about 5.0%, about 1.0% to about 5.0%, about 2.0% to about 4.0%, or about 2.5%, by weight of the first polymer component. In general, one skilled in the art can routinely determine the desired amount in any given case by simple experimentation. The cross-linker can be added at any stage of the process, however it, can typically be added after the cooling step.

Further, the disclosed microcapsules can be washed with water and/or dried to provide a free-flowing powder. Thus, the disclosed methods of preparing microcapsules can comprise a drying step for the microcapsules. Drying can be accomplished by a number of methods known in the art such as, for example, freeze drying, drying with ethanol, or spray drying. In one aspect, spray drying can be used for drying the microcapsules. Spray drying techniques are disclosed in "Spray Drying Handbook", K.
Masters, 5th edition, Longman Scientific Technical UK, 1991, the disclosure of which is hereby incorporated by reference at least for its teaching of spray drying methods.
Methods ofPreparing the ,Food Articles The food articles disclosed herein contain delivery devices, such as those disclosed herein, and can be used to deliver loading substances encapsulated within the delivery device (e.g., omega-3 fatty acids) to a subject for nutritional or medical purposes.
In one example, the delivery device is a microcapsule. The microcapsules disclosed herein have good rupture strength to help reduce or prevent breaking of the microcapsules during incorporation into food or other formulations. Furthermore, the microcapsule's shells are insoluble in both aqueous and oily media, and help reduce or prevent oxidation and/or deterioration of the loading substance during preparation of the microcapsules, during long-term storage, and/or during incorporation of the microcapsules into a formulation vehicle, for example, into food articles.
The particular method of preparing the disclosed food articles will depend on such factors as the particular food article, the delivery device, and the loading substance. In some examples, the delivery device (e.g., microcapsules) can be mixed with the ingredients of the food article before the food article is prepared. Examples of this can include adding delivery devices to batter or breading for various food articles (e.g., fish, shrimp, poultry, vegetables) and then cooking the food. In other examples, the delivery devices can be added to (e.g., contacted to or poured or sprinkled on) the food article after it is prepared, but before packaging. Typical examples of this method involve contacting the food article with the delivery device. Such contacting steps can be combined with other seasoning steps. In still another example, the delivery device can be packaged separately from the food article (e.g., microcapsules can be packaged alone as a condiment pack or mixed into other seasonings) and then added to the food article prior to consumption (e.g., by the consumer or food preparation personnel).
In one example, delivery devices, along witli other optional seasonings, can be pulse sprayed or mist sprayed onto the surface of the food article.
Alternatively., a drum can contain the delivery devices and the food article can be introduced into the drum and agitated (e.g., rolled around inside the drum). Figure 1 depicts one example of this technique, where, for example, a seasoning and delivery device comprising omega-3 fatty acids are mixed in a horizontal mixer 1. The mixture is then placed in a sprayer 2, which then applies the mixture to the food article 4 present in drum 3. Drum 3 can be rotated while the mixture is sprayed onto the food article in order to ensure even distribution of the mixture to the food article. Suitable apparatus for introducing delivery devices can be obtained commercially from suppliers such as FMC Technologies (Chalfont, PA).
The amount of delivery devices (and thus loading substance) that can be used with the disclosed food articles will depend on such factors as the type of food article, the type of loading substance, the presence of additional seasonings, the desired dietary intake, preference, and the like. Guidance can be found in the literature for appropriate amounts for given classes of loading substances and determining a particular amount is within the skill in art. Generally, an amount of delivery devices that will provide the desired ainount of loading substance to a subject, but not detract from the taste and texture of the food article can be used.
In one example, the disclosed food article comprises a snack food (e.g., a chip) and a microcapsules. In a further example, the food article is a chip and the loading substance comprises an omega-3 fatty acid. Typical amounts of microcapsules that can be used for chips are about 0.5%, 1.0%, 1.5%, 2.0%, 2.5%, 2.9%, 3.0%, 3.5%, 4.0%, ~.5%, 5.0%, 5.5%, or 6.0% by weight, based on the total weight of the chip, where any of :he stated values can form an upper or lower end point when appropriate. In other xamples, less than or equal to about 6.0%, less than or equal to about 5.0%, less than or -qual to about 4.0%, less than or equal to about 3.0%, less than or equal to about 2.0%, or less than or equal to about 1.0% by weight, based on the total weight of the chip can be used. In other examples, a chip can have about 0.5, 1.0, 1.5, 2.0, 2.5, 2.9, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, or 6.0 parts by weight microcapsules, where any of the stated values can form an upper or lower end point when appropriate. In other examples, a chip can have less than or equal to about 6.0, less than or equal to about 5.0, less than or equal to about 4.0, less than or equal to about 3.0, less than or equal to about 2.0, or less than or equal to about 1.0 parts by weight microcapsule. In another example, a chip can have microcapsules at from about 1 to about 6, from about 2 to about 4, or about 3 % by weight based on the total weight of the chip. Still further, a chip can have from about 1 to about 6, from about 2 to about 4, and about 3 parts by weight microcapsules.
In another example, the disclosed food article can comprise seasonings in addition to the delivery devices. The seasonings can be blended with the microcapsules and then added to the food article (e.g., chip). As such, disclosed herein is a seasoning for a food article that comprises a microcapsule. In one example, the delivery device comprises a microcapsule. Exemplary amounts of microcapsules that can be blended with a seasoning are about 5%, 6%, 7%, 8%, 9%, 10%, 11 %, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20 l0, 21 %, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31 %, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, or 40% by weight, based on the total weight of the blend, where any of the stated values can form an upper or lower end point when appropriate. In other examples, from about 20 to about 25%, from about 15 to about 30%, from about 10 to about 35%, from about 5 to about 40%, from about 5 to about 20%, from about 20 to about 40-% by weight, based on the total weight of the blend can be used. Also, microcapsules can be blended with a seasoning at about 5, 6, 7,

8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 parts by weight, where any of the stated values can form an upper or lower end point when appropriate. In other examples, a seasoning blend can contain from about 20 to about 25, from about 15 to about 30, from about 10 to about 35, from about 5 to about 40, from about 5 to about 20, from about 20 to about 40 parts by weight microcapsules.
When the seasoning is a chip seasoning, it can be present in an amount of about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11 %, 12%, 13%, 14%, 15 %, 16%, 17%, 18%, 19%, or 20% by weight based on the total amount of the chip, where any of the 3tated values can form an upper or lower endpoint when appropriate. In other examples, a chip can contain about l, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 parts by weight seasoning, where any of the stated values can form an upper or lower endpoint when appropriate.
When preparing chips, the chip can also contain oil in an amount of about 1, 2, 3, 4, 5, 6, 7, or 8% by weight, where any of the stated values can form an upper or lower endpoint when appropriate.
Other methods disclosed herein involve mixing the delivery device (e.g., microcapsule) with one or more ingredients used to prepare the food article prior to preparing the food article. Alternative or additional methods involve contacting an already prepared food article with the delivery device. For example, the delivery device can be blended with a seasoning for the food article. The delivery device can also be sprayed onto the food article. Further, the delivery device can be mixed with the food article.
The amount of delivery device used to prepare a food article can vary depending on the type of food article, the type of delivery device, the amount of loading substance, the desired dosage, preference, and the like. In general, the amount of loading substance desired to be delivered will be a main consideration. As an example, a microcapsule containing EPA and DHA can be added in such an amount that the food article containing the microcapsule can have from about 10 to about 250 mg of EPA+DHA. per serving. For example the food article can have about 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, or 250 mg of the loading substance per serving, where any of the stated values can form an upper or lower endpoint when appropriate. When a delivery. device contains large amounts of loading substance, then less of the deliver device needs to be used in the food article to obtain a desired level of a loading substance. When a deliver device contains small amounts of loading substance, then more of the deliver device will need to be used in the food article to obtain a desired level of a loading substance. Also, when more loading substance is desired, then more delivery device can be added, and when less loading substance is desired, then less delivery device can be added.
In other examples, the food articles can contain other additives and components.
For example, the food articles disclosed herein can also comprise a probiotic.
Probiotics are live microorganisms that can be administered to a subject and which can confer a beneficial health effect on the subject. Examples of suitable probiotics include, but are not limited to, Lactobacillus species, Lactococcus species, and Pediococcus species. In one example the probiotic can be one or more bacteria chosen from Lactobacillus acidophilus, Lactobacillus sakei, Lactococcus lactis, and Pediococcus acidilactici. These bacteria can be particularly useful in the methods and compositions disclosed herein because they are food safe (i.e., safe to use in, on, or near foods).

Methods of Use In one aspect, disclosed herein are methods of delivering a loading substance to a subject by administering to the subject a food article as disclosed herein. In a particular example, the disclosed food articles can be used as a source of fatty acids (e.g., omega-3 fatty acids), lowering triglycerides and influencing diabetes related biochemistry. In another particular example, disclosed herein are methods of supplementing omega-3 fatty acids in a subject by administering an effective amount of a food article disclosed herein, wherein the loading substance comprises an omega-3 fatty acid. In another example, disclosed herein are methods of lowering cholesterol levels, triglyceride levels, or a combination thereof in a subject by administering an effective amount of a food article disclosed herein.
Omega-3 fatty acids are vital to everyday life and function. For example, the beneficial effects of omega-3 fatty acids like cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) on lowering serum triglycerides are well established. These compounds are also known for other cardioprotective benefits such as preventing cardiac arrhythmias, stabilizing atherosclerotic plaques, reducing platelet aggregation, and reducing blood pressure. See e.g., Dyrberg et al., In: Omega-3 Fatty Acids: Prevention and Treatment of Vascular Disease. Kristensen et al., eds., Bi & Gi Publ., Verona-Springer-Verlag, London, pp. 217-26, 1995; O'Keefe and Harris, Am. J. Cardiology 2000, 85:1239-41; Radack et al., "The effects of low doses of omega-3 fatty acid supplementation on blood pressure in hypertensive subjects: a randomized controlled trial." Arch. Intern.llled.
1991, 151:1173-80; Harris, "Extending the cardiovascular benefits of omega-3 fatty acids."
Curr Atheroscler Rep 2005, 7:375-80; Holub, "Clinical nutrition: 4 omega-3 fatty acids in cardiovascular care." CMAJ2002, 166(5):608-15. Indeed, the American Heart Association has also reported that omega-3 fatty acids can reduce cardiovascular and heart disease risk. Other benefits of omega-3 fatty acids are those related to the prevention and/or treatment of inflammation and neurodegenerative diseases, and to improved cognitive development. See e.g., Sugano and Michihiro, "Balanced intake of polyunsaturated fatty acids for health benefits." J. Oleo Sci. 2001, 50(5):305-11.

The fatty acids EPA and DHA can be synthesized in the human body from a-linolenic acid (18:3); however, the conversion rate from this precursor molecule is limited (Muskiet et al., "Is docosahexaenoic acid (DHA) essential? Lessons from DHA
status regulation, our ancient diet, epidemiology and randomized controlled trials."
J. Nutr.
2004, 134(l):183-6). Accordingly, EPA and DHA in the body are primarily derived from dietary sources (e.g., oily fish). Diets rich in fish oils are known to have many beneficial effects for heart disease, cancer, arthritis, allergies, and other chronic diseases.
Epidemiological clinical trials have shown that increasing the dietary intake of omega-3 fatty acids, in the form of fish or of fish oil supplements, may reduce various risk factors associated with cardiovascular disease. See e.g., The American Heart Association, Scientific Statement, "Fish Consumption, Fish Oil, Omega-3 Fatty Acids and Cardiovascular Disease," November 2002; Appel et al., "Does supplementation of diet with 'fish oil' reduce blood pressure? A meta-analysis of.controlled clinical trials." Arch.
Intern. Med. 1993, 153(12):1429-1438; GISSI-Prevenzione Investigators.
"Dietary supplementation with omega-3 polyunsaturated fatty acids and vitamin E after myocardial infarction: results of the GISSI-Prevenzione trial." Lancet 1999, 354:447-55.
Despite the strong evidence for the benefit of omega-3 fatty acids like EPA
and DHA in prevention of cardiovascular disease, the average daily consumption of these fatty acids by North Americans is estimated to be between 0.1 to 0.2 grams, compared to a suggested daily intake of 0.65 grams to confer benefit (Webb, "Alternative sources of omega-3 fatty acids." Natural Foods Merchandiser 2005, XXVI(8):40-4). Since altering dietary patterns of populations is difficult and many people do not like to eat fish, dietary supplementation with EPA and DHA is an important approach to addressing this problem. Unfortunately, many suppleinents of omega-3 fatty acids are sensitive to oxidation and can be foul smelling and tasting. Further, compliance with dietary supplement regimens requires discipline, which is often wanting. In light of the health benefits of omega-3 fatty acids, the disclosed formulations comprising microcapsules can be used to deliver omega-3 fatty acids to a subject. In the disclosed methods of use, the food articles that are administered can be any of the formulations disclosed herein.
When used in the above described methods or other treatments, an "effective amount" of one of the disclosed food articles (or one of the loading substances therein) can be employed in pure form or, where such forms exist, in pharmaceutically acceptable salt form, foodstuff, or other form.

The specific effective dose level for any particular subject will depend upon a variety of factors including the disorder being treated and the severity of the disorder; the identity and activity of the specific composition employed; the age, body weight, general health, sex and diet of the patient; the time of administration; the route of administration;
the rate of excretion of the specific composition employed; the duration of the treatment;
drugs used in combination or coincidental with the specific composition employed and like factors well known in the medical arts. For example, it is well within the skill of the art to start doses of a composition at levels lower than those required to achieve the desired therapeutic effect and to gradually increase the dosage until the desired effect is achieved. If desired, the effective daily dose can be divided into multiple doses for purposes of administration. Consequently, single dose compositions can contain such amounts or submultiples thereof to make up the daily dose.
The dosage can be adjusted by the individual physician or the subject in the event of any counterindications. Dosage can vary, and can be administered in one or more dose administrations daily, for one or several days. Guidance can be found in the literature for appropriate dosages for given classes of pharmaceutical products.
Further, disclosed are methods for delivering a disclosed composition to a subject by administering to the subject any of the food articles disclosed herein.
EXAMPLES
The following examples are set forth below to illustrate the methods and results according to the disclosed subject matter. These examples are not intended to be inclusive of all aspects of the subject matter disclosed herein, but rather to illustrate representative methods and results. These examples are not intended to exclude equivalents and variations of the present invention which are apparent to one skilled in the art.
Efforts have been made to ensure accuracy with respect to numbers (e.g., amounts, temperature, etc.) but some errors and deviations should be accounted for.
Unless indicated otherwise, parts are parts by weight, temperature is in C or is at ambient temperature, and pressure is at or near atmospheric. There are numerous variations and combinations of reaction conditions, e.g., component concentrations, desired solvents, solvent mixtures, temperatures, pressures and other reaction ranges and conditions that can be used to optimize the product purity and yield obtained from the described process.
Only reasonable and routine experimentation will be required to optimize such process conditions.

Example 1: Microcapsule Preparation 54.5 grams gelatine 275 Bloom type A (isoelectric point of about 9) was mixed with 600 grams of deionized water containing 0.5% sodium ascorbate under agitation at 50 C until completely dissolved. 5.45 grams of sodium polyphosphate was dissolved in 104 grams of deionized water containing 0.5% sodium ascorbate. 90 grams of a fish oil concentrate containing 30% eicosapentaenoic acid ethyl ester (EPA) and 20%
docosahexaenoic acid ethyl ester (DHA) (available from Ocean Nutrition Canada, Dartmouth, Nova Scotia) was dispersed with 1.0% of an antioxidant (blend of natural flavour, tocopherols and citric acid available as DURALOXTm from KALSECTM) into the gelatine solution with a high speed POLYTRONTM homogenizer. An oil-in-water emulsion was formed. The oil droplet size had a narrow distribution with an average size of about 1 m measured by COULTERTM LS230 Particle Size Analyzer. The emulsion was diluted with 700 grams of deionized water containing 0.5% sodium ascorbate at 50 C. The sodium polyphosphate solution was then added into the emulsion and mixed with a Lightning agitator at 600 rpm. The pH was then adjusted to 4.5 with a 10 lo aqueous acetic acid solution. During pH adjustment and the cooling step that followed pH adjustment, a coacervate formed from the gelatine and polyphosphate coated onto the oil droplets to form primary microcapsules. Cooling was carried out to above the gel point of the gelatine and polyphosphate and the primary microcapsules started to agglomerate to form lumps under agitation. Upon further cooling of the mixture, polymer remaining in the aqueous phase further coated the lumps of primary microcapsules to form an encapsulated agglomeration of microcapsules having an outer shell and having an average size of 50 m. Once the temperature had been cooled to 5 C, 2.7 grams of 50%
gluteraldehyde was added into the mixture to furtlier strengthen the shell.
The mixture was then warmed to room temperature and kept stirring for 12 hours. Finally, the microcapsule suspension washed with water. The washed suspension was then spray dried to obtain a free-flowing powder. A payload of 60% was obtained.
Example 2: Microcapsule Preparation Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that 0.25% sodium ascorbate was used. A payload of 50% was obtained.

Example 3: Microcapsule Preparation Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that no ascorbate was used. A payload of 60%
was obtained.
Example 4: Microcapsule Preparation Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that 105 grams of fish oil concentrate was used and a payload of 70% was obtained.
Example 5: Microcapsule Preparation Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that it was applied to triglyceride (TG) fish oil (available from Ocean Nutrition Canada Ltd.) rather than ethyl ester fish oil.
Example 6: Microcapsule Preparation Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that gelatine (type A) and gum arabic were used as polymer components of the shell material.
Example 7.= Microcapsule Preparation Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that 150 Bloom gelatine (type A) and polyphosphate were used as polymer components of the shell material and 105 grams of fish oil concentrate was used to obtain a payload of 70%.
Example S. Microcapsule Preparatio,u Encapsulated agglomerations of microcapsules were formed in accordance with the method of Example 1 except that transglutaminase was used to cross-link the shell material.
Example 9: Potato Chips Microencapsulated omega-3 oil (MEG-3TM powder) was provided by Ocean Nutrition Canada (Dartmouth, Canada). Unseasoned potato chips and dry seasoning were provided by Kettle Chip Company (Salem, OR).
The dry seasoning (at ambient temperature) and microcapsules (at minus 18 C) were placed in a plastic laboratory tub. The tub was covered and the contents were 3haken vigorously by hand for about one minute until the mixture was homogeneous. A
rommercial blender at low speed for a short period of time can also be used.
Since a dry blend can heat during the blending process, it can be desired to keep the mixture cool.
See Table 4.
In a stainless steel bowl, the unseasoned chips were sprayed with oil (e.g., PAM;
ConAgra Foods, Omaha, NE), while tossing the chips with a spatula until about 4 % by weight of the oil was sprayed on the chips. It is also possible to use freshly fried chips, since the residual oil can serve as an adhesive for the dry, seasonings.
The dry seasoning was added to the PAM-sprayed chips while tossing was continued until at least 95% of the dry seasoning had adhered to the chips. In multiple trials, the amount of seasoning pick up was from about 95% to about 99%. A
standard tumbling drum, where the chips are tossed with dry seasoning added at a pre-determined rate, can also be used. See Table 4.
It can also be desired to minimize the time between dry seasoning blending and application to the chips.
The chips were then placed in a gas-barrier pouch, which was flushed with ambient nitrogen gas and sealed.
Table 4:
Seasoning Blend Component 100 grams Weight (g) Percent Classic Barbeque 77.52 10.00 77.52%
Seasoning Microencapsulated 22.48 2.90 22.48%
Omega-3 Fatty Acid 100.00 12.90 100.00%
Chip Component 100 grams Weight (g) Percent Unsalted Chip 283.70 83.10 83.10%
Seasoning Blend 44.04 12.90 12.90%
Oil 13.66 4.00 4.00%
341.40 100.00 100.00%

Example 10: Apple Sauce Baby Food Applesauce containing microcapsules was prepared according to the formulation shown in Table 5. Specifically, applesauce was placed into a water-jacketed kettle preheated to 99.5 C. Microencapsulated omega-3 oil (MC601 S 12TG or MC60DHA
from Ocean Nutrition Canada; Dartmouth, Canada) was added to the applesauce. A high shear mixer with a rod attachment was positioned in mixture and the mix speed was set at 800 rpm for the batch. The mixture was covered to minimize evaporation and maintained at 90.5 C for approximately 10 minutes. The hot mixture was then filled into glass containers (125 g serving size). Foil seals were ironed onto the containers and the containers were inverted for 2 minutes or more. The containers were then cooled in an ice water bath and stored refrigerated.

Table 5:

Ingredients Weight (g) Real %
Applesauce with Vitamin 1000.00 99.68 C, 100% DV, aseptic Omega-3 microcapsules 3.210 0.32 Total 1003.210 100.00 No off-flavors were detected in the applesauce stored under accelerated or ambient conditions. The samples had about 60 mg EPA+DHA per 125 g serving.
Example 11: Apple Banana Baby Food Apples and banana baby food containing microcapsules was prepared by first Dlending bananas with citric acid to a target pH of about 4.20-4.30. Then, in a water-iacketed kettle, the bananas were combined with apples and the mixture was pureed to a lesired consistency. Microencapsulated omega-3 oil (MEG-3TM powder from Ocean STutrition Canada; Dartmouth, Canada; 30-50 mg of EPA+DHA per serving) was blended nto the mixture with a hand mixer. The mixture was covered to minimize evaporation md maintained at 91 C. The hot mixture was then filled into glass containers (125 g ;erving size). Foil seals were ironed onto the containers and the containers were inverted :or 2 minutes or more. The containers were then cooled in an ice water bath and stored 'efrigerated. Taste test revealed that lower levels of EPA+DHA were preferred over iigher levels.

Example 12: Breaded Shrimp Shrimp containing microcapsules were prepared according to the formulation shown in Table 6. Specifically, frozen shrimp were dipped into a predust containing microencapsulated omega-3 oil (MEG-3Tm powder from Ocean Nutrition Canada;
Dartmouth Canada). The shrimp were shaken gently, to remove the extra predust adhering to the shrimp. The shrimp were then dipped into the batter and coated with breadcrumbs. Each shrimp took up to about 0.3 g of predust, 0.4 g batter and 1 g breading. The shrimp were then fried in 177 C oil for approximately 4 minutes.
The shrimp were kept frozen in plastic bags until ready to test.

Table 6:

Ingredients Weight (g) Real %
Shrimp, frozen 81.00 72.58 Predust* 5.40 4.83 Batter Mix* 7.20 6.45 Bread Crumbs 18.00 16.12 Total: 111.60 100.00 *see formula below Predust Ingredient Weight (g) Real %
Batter Mix 56.67 56.67 Omega 3 powder 43.33 43.33 Total: 100.00 100.00 Batter Mix Ingredient Weight (g) Real %
Batter Mix 80.00 34.78 Water, filtered 150.00 65.22 Total: 230.00 100.00 The shrimp had 175 mg EPA+DHA (350 mg before frying) per serving (about 18 shrimp). In taste test, the flavor was acceptable. Since the microcapsules may interfere with adherence of crust to the shrimp, care should be taken during battering and breading processes.
E'xample 13: Pasteurized Process Cheese Food Pasteurized process cheese containing microcapsules was prepared according to the formulation shown in Table 7. All dry ingredients were first blended. Then all wet ingredients were gradually blended into the dry ingredients with a whisk. The mixture was heated in a double boiler to about 60 C. Cheese was added to the mixture and melted by heating to about 79-82 C with mixing. The mixture was vacuum packaged in plastic film pouches to form slices. The pouches were chilled to form and stored refrigerated.
Table 7:

Ingredients Weight (g) Weight %
Cheese 257.50 52.34 Water 118.41 24.07 Corn oil 50.00 10.16 Starch, Mira Clear 340 (Staley) 26.25 5.34 Starch, Tenderfil 8 (Staley) 21.25 4.32 Sodium citrate 10.00 2.03 Disodium Phosphate 5.00 1.02 Annatto color 0.04 0.008 Omega-3 3.56 0.72 Total 492.01 100.00 Microencapsulated omega-3 oil (MEG-3TM powder from Ocean Nutrition Canada;
Dartmouth Canada) was added with the dry ingredients or the wet ingredients.
Both methods produced similar results; although, adding them with the dry ingredients was easier. The products had 32 mg of EPA + DHA oil per serving (30 g slice). At these loading levels of EPA+DHA, the products tasted acceptable. Products containing higher levels (50 mg EPA+DHAlserving and higher) had detectable fish flavors, but the fish flavor dissipated somewhat as the product aged.

Example 14: Chewy Granola Bar A chewy granola bar containing microcapsules was prepared according to the formulation shown in Table 8. Specifically, microencapsulated omega-3 oil (MEG-powder from Ocean Nutrition Canada; Dartmouth, Canada) was pre-blended with honey.
To account for loss during transfer, a larger amount than needed was prepared based on the following calculation (16.54 % microcapsules and honey mixture). The mixture was stirred well and allowed to sit and hydrate. In a large mixing bowl, oats and crisp rice were combined and gently mixed. Oil was drizzled into the mixture while mixing continued. The microcapsules and honey mixture mixed into the mixture and gently stirred for 1 minute. The mixture was spread onto baking sheets coated with non-stick spray and baked at 121 C in a convection oven for 20- minutes, tossing after 10 minutes.
After cooling, the product was stored in an airtight foil package until ready to use.

Table 8:

Ingredients Weight (g) Real %
Rolled Oats 186.76 46.69 Honey, Clover (60 C) 92.95 23.24 Crisp Rice 84.89 21.22 Omega 3 18.42 4.61 Canola Oil 16.98 4.24 Total 400.00 100.00 The product contained 130 mg EPA + DHA per serving (40g). Fishy flavors were at were least noticeable when the microencapsulated oil was baked with cereals. It appears that cinnamon may have accentuated the fishy flavors. However, the microcapsules baked and blended with honey (or syrup) produced an acceptable flavor.
Example 15. ChickeuDinnerBabyFood A chicken dinner baby food containing microcapsules was prepared according to the formulation shown in Table 9. Specifically, the dry ingredients were blended and set aside. Chicken was boiled, cooled, chopped into small pieces, and then finely ground in a food processor. Egg noodles were cooked, cooled, and set aside. Peas were cooked, cooled, pressed through a sieve, and set aside. Carrots, split peas, chicken fat, oil, and the noodles were blended in a food processor. While blending, the dry ingredients and water were slowly added. The ground chicken was then added arnd the mixture was blended until the mixture was completely combined and smooth. The product was then filled into to 8 oz glass jars and retorted at 15 psi for 40 minutes. The product was stored at ambient temperature.

Table 9:

Ingredients Weight (g) Weight %
Water 250.00 48.13 Carrots, IQF diced 205.00 39.45 Chicken breast 26.00 5.01 Peas, IQF 11.00 2.12 Egg noodles, cooked 10.00 1.93 Rice flour 9.00 1.73 Chicken fat 3.50 0.67 Onion powder 2.00 0.39 Soybean oil 1.50 0.29 Celery powder 0.05. 0.01 Omega-3 1.40 0.27 Total 519.45 100.00 No off-flavors or odors were detected in the product. The product contained about 60 mg EPA + DHA per serving (125 g). To avoid shearing and damage of microcapsules, it was found that the baby food base needed to be prepared prior to the addition of microcapsules.
Example 16.= Potato Chip Seasoning A potato chip seasoning containing microcapsules was prepared according to the formulation shown in Table 10. Specifically, the ingredients were blended together. The flavors tested included BBQ, sour cream and green onion, and salt and pepper.
Then the mixture was applied to potato chips at a level of 12.9 %. If there was insufficient residual Dil on the chips to allow for the seasoning to properly adhere, oil was sprayed (about 4 10 by weight) onto the chips to act as an adhesive. The chips were packaged in a nitrogen flushed, metallized film and stored at ambient temperature. The chips contained 130 g of EPA + DHA per serving (30 g of seasoned chips).

Table 10:

Ingredient Weight (g} Weight %
Dry Seasoning 75.00 77.52 Omega-3 Powder 21.75 22.48 Total 96.75 100.00 Under accelerated conditions (37.8 C) some off-flavors were detected after 4 weeks. Under ambient conditions (21.1 C), the flavors of the products were slightly muted but similar to the controls at 6 weeks of storage Example 17. = Extruded Cereal Bar An extruded cereal bar containing microcapsules was prepared according to the formulation shown in Table 11. Specifically, fat was creamed with sugar and liquids ingredients were added. Then the microcapsules were blended with the dry ingredients.
All ingredients were combined and mixed to form dough. The dough was extruded with a fruit filling center. The product was baked at 163 C for approximately. 6-7 minutes.
Table 11:
Fruit Filling Ingredients Weight (g) Real %
Granulated sugar 35.45 17.72 Strawberry puree, seedless 20.86 10.43 Water 18.25 9.12 Strawberry juice concentrate 17.73 8.86 Starch (Rezista) 6.26 3.13 lemon juice 1.04 0.52 Salt 0.42 0.21 Dough Ingredients Weight (g) Real %
Pastry flour 43.86 21.93 Fructose 11.10 5.55 Unsalted butter 10.63 5.31 Molasses 5.13 2.56 Non fat milk 11.73 5.86 Egg white powder 4.35 2.17 Canola oil 3.54 1.77 Sugar 3.54 1.77 Salt 0.59 0.29 Lecithin 0.59 0.29 Baking powder 0.52 0.26 Baking soda 0.47 0.23 Emulsifier 0.24 0.12 Xanthan gum 0.18 0.09 Strawberry flavor 0.12 0.06 Vanilla flavor 0.08 0.04 Omega-3 Powder 3.33 1.66 Total 200.01 100.00 The product contained 50 mg of EPA + DHA per serving (40 g). The product had acceptable flavor at time of manufacture. Further the product flavor was acceptable after 4 months.
Example 18: Chicken Nuggets Chicken nuggets containing microcapsules were prepared according to the formulation shown in Table 12. Four batches were prepared: a control, a batch containing 150 mg EPA+DHA per 100 g serving, a batch containing 175 mg EPA + DHA per 100 g serving , and a batch containing 300 mg EPA+DHA per 100 g serving.
Microencapsulated omega-3 oil (MEG-3TM powder from Ocean Nutrition Canada;
Dartmouth Canada) was added to soy protein, which was then added to ground chicken meat. The mixture was stirred, formed into nugget shapes, coated with a pre-dust, and then a batter and breading was applied. The product was par-fried for 30 seconds at approximately 196 C to set the coating and the color. The product was then transferred to Ehe oven where it was fully cooked at 177 C for approximately 3 minutes. For the ,hicken nuggets containing the microcapsules the cider trim was reduced to compensate For the added microcapsules. The final weight of each batch was 400 kg. The final product was packaged in clear plastic bags and stored frozen until consumption. The preparation instructions for the product include reheating in the oven at 220 C for 10-15 minutes, microwaved, or deep-fried.

Table 12:

Ingredients Quantity (kg) Cider trim 253.94 Skin and fat 14.50 Say protein FX 213 20.25 Water 107.78 Salt 3.57 Total 400.00 The samples were evaluated monthly for sensory attributes, color, and pH
during a 12-month shelf life. The samples were evaluated initially for difference from control and at the end of shelf life for acceptability. The samples were also tested at the beginning and end of shelf life for EPA+DHA and moisture content.
The EPA+DHA and moisture contents of the nuggets remained constant throughout the shelf life. No significant difference was found between the nuggets containing 300 mg of EPA+DHA per serving and the control, at the beginning of the shelf life. At the end of the 12-month shelf life, panelists indicated that they "liked very much"
the nuggets containing 300 mg EPA+DH:A. per serving. The sample nuggets had similar stability to the control nuggets. High levels of EPA+DHA can be added per serving without affecting the sensory and physical attributes of the nuggets or the overall stability.
Example 19: Soymilk Soymilk containing microcapsules was prepared using an automatic soymilk maker. Two batches of soymilk were produced, one control and one containing 250 mg EPA+DHA per 250mL serving. Specifically, 85 g of dry soybeans were soaked in tap water overnight. The soaked beans were drained and rinsed. 1.5 L of water was poured into the soymilk maker and the beans were placed in the filter cup. The soymilk maker was then started. The soymilk was collected and the spent beans discarded. The soymilk was cooled. Microencapsulated omega-3 oil (MEG-3TM powder from Ocean Nutrition Canada; Dartmouth Canada) was added and the soy milk was pasteurized at 85 C
for 5 sec. Pasteurization and addition of MEG-3Tm powder to plain soymilk helped to reduce beany off-notes.
Three more batches of soymilk were produced as just described: pasteurized soymilk, pasteurized soymilk with 1 cm3 salt and 30 cm3 sugar, pasteurized soy milk with microencapsulated omega-3 oil, 1 cm3 salt and 30 cm3 sugar (the salt and sugar were added to the soymilk after pasteurization). Pasteurized soy milk containing salt and sugar tasted similar to commercial soymilks. The pasteurized soy milk containing microcapsules, salt and sugar was slightly less sweet but tasted better than the pasteurized soymilk containing no salt and sugar.
Soymilk was an acceptable beverage for the addition of microcapsules. No off-flavors or odors attributable to the powder were observed, even at 250 mg EPA+DHA per serving. Some of the typical soy beany flavor was masked by the microcapsules.
Example 20: Frozen Waffles Frozen waffles containing microcapsules were prepared according to the formulation shown in Table 13. Specifically, the dry ingredients were blended together.
Water, melted butter, and vanilla were then added to the dry, mix. After mixing the ingredients together, the batter was placed onto oil brushed waffle maker and baked for 70 seconds. The waffles were removed from the waffle maker and placed into plastic pouches, separated by wax paper, and frozen.

Table 13:

Ingredients Weight (g) Real %
Water 187.40 34.1965 All Purpose Flour 163.90 29.9082 Blueberry, low moisture 60.00 10.9487 Sugar 50.00 9.1239 Eggs, Fresh Liquid 47.00 8.5765 Butter, Unsalted 25.00 4.5620 Omega 3 4.36 0.7956 Vanilla Extract 3.35 0.6113 Blueberry Flavor, Natural 2.00 0.3650 Salt 2.00 0.3650 Baking Soda 2.00 0.3650 Sodium Aluminum 1.00 0.1825 Phosphate Total 1000.00 100.0000 The waffles had about 130 mg of EPA + DHA per 85 g serving. Flavor in both levels were acceptable in first round tastings. Plain and blueberry waffles were also prepared. An apple cinnamon flavor was included in early development, but cinnamon seems to enhance off flavors. Cinnamon should not be used as a flavor for this type of product.
Example 21: Granola Cereal Granola cereal containing microcapsules were prepared according to the formulation shown in Table 14. Microencapsulated omega-3 oil (MEG-3TM powder from Ocean Nutrition Canada; Dartmouth, Canada) was blended with honey. The mixture was stirred well and the mixture was allowed to hydrate. Vanilla was then added to the mixture and mixed well. Brown sugar, flour, cinnamon, and nonfat dry, milk were slowly stirred for 1 minute. Oats, sunflower seeds, almonds, and sesame seeds were then added.
Raisins were added at the end of baking to cooled granola. Oil was heated to 43 C and drizzled into a bowl while continuing to stir for 1 minute. The microcapsules, vanilla, and honey mixture were heated to 60 C and drizzled into the mixture. After mixing for 2 minutes, the mixture was spread onto uncoated baking sheets. The mixture was baked 121 C in a convection oven on low fan for 30 minutes. The mixture was then tossed after 15 minutes. After cooling, the granola was stored in an airtight container until ready to use.

Table 14:

Ingredients Weight (g) Real %
Rolled Oats 240.97 48.19 Honey, Clover (60 C) 75.00 15.00 Canola Oil (43 C) 40.00 8.00 Brown Sugar, granulated 30.00 6.00 Sunflower seeds 25.00 5.00 Whole Wheat flour 21.25 4.25 Almonds, raw, sliced 20.00 4.00 Non fat dry milk 15.00 3.00 Sesame Seeds 12.50 2.50 Raisins, midgets 10.00 2.00 Vanilla Extract, 2X 3.75 0.75 Cinnamon, ground 3.75 0.75 Omega 3 2.78 0.56 Total 500.00 100.00 The granola cereal contained about 50 mg EPA + DHA per serving (55 g). While fishy flavors were noticeable when the cereal was fresh, this dissipated over 10-12 days.
The cinnamon may have accentuated the fishy flavors. Samples tasted in milk did not have any off flavors.
Example 22: Gummy Candies Gummy Candies containing microcapsules were prepared according to the formulation shown in Table 15. Specifically, sugar, corn syrup, microencapsulated omega-3 oil (MEG-3TM powder from Ocean Nutrition Canada; Dartmouth Canada) and water were mixed together in a cooking, vessel. The mixture was brought to a boil at 118 C. The mixture was removed from heat and cooled to 96 C. Gum mucilage was vigorously stirred into the syrup to create a homogenous blend. Gum mucilage was prepared by adding gelatin to water and holding in a water bath at 60 C for one hour or until the solution was clear. The solution was kept warm (above 54 C) until ready for use in gturmzy candies. Flavor, color and acid solution was added and the mixture was blended well. The mixture was then placed in starch molds and allowed to set for 48 bours at room temperature. The resulting gummy were removed from the molds and lightly oiled with a 1:3 blend of mineral/coconut oil. The product was allowed to age for 2 days before packaging in a nitrogen purged, metallized film.

Table 15:

Ingredient Quantity (g) Weight %
Corn syrup 390.00 40.50 Sugar 300.00 31.15 Water 80.00 8.31 *Gum mucilage Gelatin, 225 Bloom 55.00 5.71 Water 100.00 10.38 Apple flavor 5.00 0.52 Malic acid, 50% solution 25.00 2.60 Green food color 0.43 0.04 Omega-3 Powder 7.50 0.78 Total 962.93 99.99 *prepare separately Gummy candies containing about 50, 100, and 130 mg EPA + DHA. per serving (40 g) were tried. Lower levels gave favorable results. Also, different methods of addition of the microcapsules were tried, such as soaking with gelatin in mucilage, boiling with syrup, and boiling in water for 5 minutes prior to addition of syrup. Addition of the microcapsules to the mucilage produced a grainy texture and soft gel.
Boilingof the microcapsules in water prior to addition of syrup actually provided the best results.
Example 23: Pasta Sauce Pasta sauce containing microcapsules were prepared according to the formulation shown in Table 16. Specifically, the wet ingredients were mixed together and the dry ingredients were mixed together. The dry band wet mixtures were then combined.
The mixture was heated to 88 C and held at that temperature for 1 minute. The mixture was then poured into glass jars.

Table 16:

Ingredients Weight (g) Weight %
Tomatoes, 3/8" diced 196.28 28.28 Water 230.00 33.13 Tomato puree 160.00 23.05 Sugar 39.00 5.62 Extra virgin olive oil 17.00 2.45 Onions, diced 14.00 2.02 Beef base 8.00 1.15 Modified food starch 6.85 0.99 Basil, IQF 4.30 0.62 Salt 6.50 0.94 Onion powder 3.00 0.43 Garlic puree 4.00 0.58 Citric acid, anhydrous 1.00 0.14 Black pepper 0.40 0.06 Omega-3 3.72 0.54 Total 694.05 100.00 Samples containing about 100 mg, 120 mg, and 130 mg EPA + DHA per serving (125 g) were prepared. No fishy flavors were detected at any levels initially or after 3 months of storage.
Example 24: Strawberry Yogurt Smoothie A Strawberry Yogurt Smoothie (serving size of 8 fl oz; about 226 g) incorporating microencapsulated omega-3 fatty acids (1812TG Omega-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 17.
The product had a 130 mg dosage of EPA + DHA per serving.

Table 17:

Ingredients Weight (g) Weight %
Plain Yogurt 438.24 43.82 Strawberry Puree, Seedless 110.62 11.06 Water 299.78 29.98 Liquid Fructose 143.81 14.38 Strawberry Flavor 0.93 0.093 Red Color 0.02 0.002 Dipotassium Phosphate 1.33 0.133 Omega-3 3.83 0.383 Pectin 1.44 0.144 Total 1000.00 100.00 Specifically, strawberry puree, water, liquid fructose, strawberry flavor, and red color were mixed together in a pot. Dipotassium phosphate, pectin, and the microcapsules were then added to the wet ingredients. The mixture was heated to 88 C
and then cooled to room temperature. Yogurt was added next and the mixture was again heated to 88 C. The mixture was then homogenized at a total pressure of 2,500 psi (first stage at 2,000 psi and second stage at 500 psi). The formulation was then placed into bottles and stored refrigerated until use.
A second smoothie was prepared according to the formulation in Table 6.
Specifically, 1% milk, starch, gelatin, and whey protein were mixed together.
The microcapsules were then sprinkled over the surface and allowed to hydrate for 5 minutes.
The mixture was then heated to 55 C and homogenized at a total pressure of 2,300 psi (first stage at 1,800 psi and second stage at 500 psi). The homogenized formulation was then pasteurized at 86 C for 30 minutes and cooled to 38 C. Yogurt culture mixed with 2% milk was added to the homogenizedlpasteurized formulation and incubated at for approximately 10 hours, or until the mixture reached a pH of 4.5. The resulting mixture was then mixed with a fruit preparation and heated to 88 C. Then, the mixture was again homogenized at a total pressure of 2,500 psi (first stage at 2,000 psi and second stage at 500 psi). The mixture was chilled and stored refrigerated until ready to use.
Table 18:

Ingredients Weight (g) Weight %
Milk, 1% milk fat 428.87 42.89 Starch 5.71 0.57 Whey Protein Isolate 1.99 0.20 Milk, 2% milk fat 1.64 0.16 Gelatin 1.19 0.12 Yo-Fast 17, yogurt culture 0.13 0.01 Strawberry fruit prep 556.64 55.66 Omega-3 3.83 0.383 Total 1000.00 100.00 Both processes produced smoothies with acceptable flavor, odor, and texture.
Example 25: Orange Juice A batch of orange juice (18 servings; each serving size being 250 g) incorporating nicroencapsulated oinega-3 fatty acids (1812TG Omega-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 19.
Specifically, the microcapsules were sprinkled on the surface of orange juice in a blend tank equipped with an agitator providing a minimum of 30 rpm. The juice was blended for 5 minute. Afterwards, the juice was pasteurized at 91 C for 17 seconds with a flow rate of 212 L/minute. The pasteurized juice was filled into gable top containers and stored refrigerated.

Table 19:

Ingredients Weight (g) Weight %
Orange Juice 4500.00 99.74 Omega-3 Powder 11.88 0.26 Total 4511.88 100.00 The orange juice contained 100 mg of EPA + DHA (120 mg of total omega-3 fatty acids) per serving. In taste tests there was no perceptible difference in taste, texture, or quality between the omega-3 orange juice and the control.
Example 26.= Chocolate Frozen Dairy Dessert A chocolate frozen dairy dessert (serving size of %a cup; about 118 mL) incorporating microencapsulated omega-3 fatty acids (MEG-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 20. The product had a 100 mg dosage of EPA + DI-lA per serving.

Table 20:

Ingredients Weight (g). Percent Chocolate Ice Cream Non Fat Milk 750.00 59.88%
Sugar 200.00 15.97%
Heavy Cream 150.00 11.98%
MPC 80 70.000 5.59%
Corn Syrup, Regular 42 DE 40.000 3.19%
Cocoa Powder 24.000 1.92%
Omega-3 Powder 7.00 0.56%
Chocolate Flavor 3.410 0.27%

Stabilizer 3.00 0.24%
Tricalcium Phosphate 2.000 0.16%
Probiotic Blend, 150 B/gm (from 3.000 0.24%
DSM; L10/L26 (50(50 Ratio)) Total 1252.41 100.00%
Specifically, all dry ingredients were blended except the calcium phosphate and probiotic blend. The mixture of dry ingredients was then combined with milk, cream, and corn syrup. The mixture was stirred until smooth. Next, the mixture was heated to 72 C
for 30 seconds. After cooling to about 4 C, the mixture was aged for 24 hours under refrigeration. Chocolate flavor and the remaining ingredients were then added and the resulting mixture was placed in an ice cream freezer to the desired overrun (target 70%).
The ice cream was ejected from the freezer and packed into individual containers, which were hard frozen overnight.
The ice cream had a start weight per 4 fl. oz of 150, end weight per 4 fl. oz of 90, and overrun of 67.00%. The ice cream had 100 mg of EPA + DHA per 118mL
serving.
Further, each serving of the ice cream contained 200,000,000 colony forming units (CFU) of probiotic per serving.
The nutritional facts of the ice cream are as follows: 150 calories (45 from fat); 5 g of total fats (3 g from saturated fat; 0 g from trans fat); 20 mg of cholesterol; 40 mg of sodium; 19 g of total carbohydrates (less than 1 g of dietary fiber; 18 g from sugar); and 7 g of protein. The ice cream also contained 6% vitamin A, 15% vitamin C, 15%
calcium, and 4% iron, which are percent daily values based on a 2000 calorie diet.
Exampie 27.= Strawberry Frozen Dairy Dessert A strawberry frozen dairy dessert (serving size of %2 cup; about 118 mL) incorporating microencapsulated omega-3 fatty acids (MEG-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 21. The product had a 100 mg dosage of EPA + DHA per serving.

Table 21:

Ingredient Weight (g) Percent Non Fat Milk 750.00 54.21%
Sugar 200.00 14.46%

Strawberry, Sliced, Sweetened 155.000 11.20%
Heavy Cream 150.00 10.84%
MPC 80 70.000 5.06%
Strawberry. Syrup 42.000 3.04%
Omega-3 Powder 8.00 0.58%
Stabilizer 3.00 0.22%
Tricalcium Phosphate 2.000 0.14%
Probiotic Blend, 150 B/gm (from 3.500 0.25%
DSM; L10/L26 (50/50 Ratio) Total 1383.50 100.00%
Specifically, all dry ingredients were blended except the calcium phosphate and probiotic blend. The mixture of dry ingredients was then combined with milk and cream.
The mixture was stirred until smooth. Next, the mixture was heated to 72 C for seconds. After cooling to about 4 C, the mixture was aged for 24 hours under refrigeration. Strawberry syrup and the remaining ingredients were then added and the resulting mixture was placed in an ice cream freezer to the desired overrun (target 70%).
The ice cream was ejected from the freezer and packed into individual containers, which were hard frozen overnight.
The ice cream had a start weight per 4 fl. oz of 150, end weight per 4 fl. oz of 95, and overrun of 65.00%. The ice cream had 100 mg of EPA + DHA per 118 mL
serving.
Further, each serving of the ice cream contained 200,000,000 colony forming units (CFU) of probiotic per serving.
The nutritional facts of the ice cream are as follows: 150 calories (40 from fat);
4.5 g of total fats (2.5 g from saturated fat; 0 g from trans fat); 20 mg of cholesterol; 35 mg of sodium; 21 g of total carbohydrates (0 g of dietary fiber; 18 g from sugar); and 6 g of protein. The ice cream also contained 6% vitamin A, 20% vitamin C, 15%
calcium, and 0% iron, which are percent daily values based on a 2000 calorie diet.

Example 28: Microwave Popcorn Microwave popcorn (serving size of 30 g) incorporating microencapsulated omega-3 fatty acids (MEG-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 22. The product had a 32 mg dosage of EPA + DHA per serving.

Table 22:

Ingredient Weight (g)- Percent Popcorn 70.11 70.11%
Hydrogenated Soybean Oil 25.50 25.50%
Salt 3.00 3.00%
Omeg,a 3 Powder 0.75 0.75%
Butter Flavor 0.60 0.60%
Annatto 0.04 0.04%
Total 100.00 100.00%

Specifically, fat was melted at about 49 C. While stirring and maintaining heat, annatto color was then added to the melted fat. In a separate container, all dry ingredients were blended together. The dry, ingredients were then added to the melted fat.
Popcorn was then placed into a microwave popcorn bag. The fat-dry ingredient slurry, which contained the microencapsulated omega-3 oil, was deposited into the bag (30 g per bag).
The bag was sealed and folded into thirds. The fat was allowed to harden.
Example 29: Country Style Baked Beans Country style baked beans (serving size of %z cup, about 130 g) incorporating microencapsulated omega-3 fatty acids (18 12TG powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Tables 23 and 24.
The product had a 32 mg dosage of EPA + DHA (0.2133 g powder) per serving.
Basically, beans were rinsed well and soaked at ambient temperature overnight in water (3 x volume of beans). Next, a large pot of water was brought to a boil.
The beans were drained and then added to the boiling water. The beans were boiled for 5 minutes.
The boiling water was drained and the beans were rinsed with cold water. The beans were then drained in a colander for 15 minutes before transferring to the cans.
The country style sauce was prepared according to the formulation in Table 23.
Table 23:

Ingredient Weight (g) Percent Water 721.00 75.700%
Sugar 162.00 17.009%
Modified Food Starch 20.00 2.100%

Salt 15.00 1.575%
Molasses 16.00 1.680%
Pork Base 8.00 0.840%
Onion Powder 4.00 0.420%
Omega 3 Powder 2.90 0.304 10 Caramel Color 1.50 0.157%
Yellow Mustard Flour 1.00 0.105%
Garlic Powder 1.00 0.105%
Cloves, ground 0.04 0.004%
Yield: 100% 952.44 99.999%

The dry ingredients were weighed and then pre-blended in a saucepan. Water was added to the dry ingredients in the saucepan and the mixture was blended well.
Molasses and pork base was added next and the mixture was blended. The sauce was brought to a simmer (> 91 C) for 5 minutes to thicken the starch. The saucepan was cooled in an ice water bath and brought to a 100 % yield. The sauce had a pH of 5.6 and brix of 22.5.
The beans were then prepared according to the formulation in Table 24.
Table 24:

Ingredient Weight (g) Percent County, Style Sauce (described in Table 23) 121.80 53.70%
Navy Beans, soaked, 6 min blanch 92.00 40.56%
Salt Pork, 1/2" x 1" chunk 13.00 5.73%
Total 226.80 99.99%
Specifically, the beans were weighed into a can. The sauce was also weighed into the can. The mixture was topped with a piece of salt pork and the can was sealed. Water was added to a retort and the cans were layered into the retort. The water was brought to a boil and the retort lid was sealed. The retort vented with steam escaping through a vent for 15 minutes and then a temperature gauge was placed on top. Once the temperature reached 121 C (15 psi), the beans were retorted for 60 minutes. Heat was then removed and the gauge was vented until ambient pressure was reached. The lid was removed and the cans were transferred to an ice water bath. After samples were cold, they were dried and stored under refrigeration.
Example 30: Gummy Sears Gummy bears (serving size of 2 g per gummy bear) incorporating microencapsulated omega-3 fatty acids (MEG-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 25. The product had a 15 mg dosage of EPA + DHA per 2 g serving.

Table 25:

Ingredient Weight (g) At Deposit Percent At Deposit Corn Syrup 30.000 24.300 31.14% 27.97%
Sugar 26.000 26.000 26.98% 29.93%
Water 10.000 6.217 10.38% 7.16%
Gelatin - Gum Mucilage 4.500 4.500 4.67% 5.18%
(250 Bloom) Sorbitol 1.000 1.000 1.04% 1.15%
Water - Gum Mucilage 16.000 16.000 16.61% 18.42%
Omega 3 Fish Oil 4.650 4.650 4.83% 5.35%
Blood Orange Flavor 0.800 0.800 0.83% 0.92%
Blood Orange Oil Flavor 0.200 0.200 0.21% 0.23%
Citric Acid, 50% Solution 1.800 1.800 1.87% 2.07%
Lactic Acid, 88% 1.200 1.200 1.25% 1.38%
Orange Color 0.150 0.150 0.16% 0.17%
Red Color 0.050 0.050 0.05% 0.06%
Total 96.35 86.87 100.00% 100.00%

Specifically, the omega-3 powder was dispersed in water and stirred until completely dissolved. Gelatin was added and melted in a water bath at 77 C.
Next, sugar, corn syrup, and water were weighed together in a cooking vessel. The mixture was brought to a boil and the sides of the pot were washed of any crystals.
Boiling was continued unti190% solids (118 C). The pot was removed from the heat and cooled to 96 C. Gum mucilage was added to and blended with the cooked syrup. Flavor, color, and acid solution were added next and blended well. The resulting mixture was deposited into dry starch molds and allowed to set for 48 hours at room temperature. The gummies were removed from the molds and excess starch was brushed off. The gummies were brushed lightly with capol and allowed to age for 2 days before packaging. The cooked yield was 90.16%.
Example 31: Natural Lemon Chew A natural lemon chew (serving size of 5.6 g) incorporating microencapsulated omega-3 fatty acids (MEG-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 26. The product had a 100 mg dosage of EPA + DHA per 5.6 g serving.

Table 26:

Ingredients Start Wt (g) End Wt (g) Starting % Finished %
Dried Whipping Egg Whites 33.00 33.00 1.54% 1.61%
Water 55.50 55.50 2.59% 2.71%
Invert Sugar 150.00 150:00 7.01% 7.33%
Corn Syrup, 42 DE 75.00 75.00 3.51% 3.67%
Sugar 690.00 690.00 32.25% 33.74%
Corn Syrup, 42 DE 500.00 410.00 23.37% 20.05%
Water 100.00 95.65 4.67% 4.68%
Palm Oil, 102 mp 225.00 225.00 10.52% 11.00%
Omega 3 Oil 250.00 250.00 11.69% 12.22%
Malic Acid, Fine Powder 24.00 24.00 1.12% 1.17%
Citric Acid, Fine Powder 6.00 6.00 0.28% 0.29%
Nat Lemon/Lime Flavor 18.00 18.00 0.84% 0.88%
Lemon Oil 9.00 9.00 0.42% 0.44%
Tumeric Powder 3.90 3.90 0.18% 0.19%
Total 2139.40 2045.05 100.00% 100.00%

Specifically, in a mixer bowl with a whip attachment, egg protein was solubilized in the first measure of water. In a separate container, sugar and the first measure of corn syrup was brought to a boil. The boiled syrup was slowly added to the mixer bowl while mixing on low speed. After all syrup had been added, the speed was increased to maximum speed and the mixture was whipped until the volume was at maximum.

In another container, palm oil was melted to clarity and combined with 80% of the omega-3 powder, until thickening began. The resulting paste was stirred until all dry ingredients were evenly coated with fat.
Sugar, the second measure of corn syrup, and water were brought to a boil (126 C). Syrup was slowly poured into the mixer bowl while mixing slowly. The omega-3 paste was added and mixed until even. Acid, the remaining dry omega-3 powder, and flavors were added next and mixed until even. The resulting mixture was poured and formed as a slab on a cool surface. The product was cut and wrapped. The product had a cooked yield of 95.59%.
Example 32: Orange Ch e w An orange chew (serving size of 5.6 g) incorporating microencapsulated omega-3 fatty acids (MEG-3 powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 27. The product had a 100 mg dosage of EPA + DHA per 5.6 g serving.

Table 27:

Ingredient Start Wt (g) End Wt (g) Starting % Finished %
Dried Whipping, Egg Whites 33.00 33.00 1.53% 1.60%
Water 55.50 55.50 2.57% 2.69%
Invert Sugar 150.00 150.00 6.96% 7.27%
Corn Syrup, 42 DE 75.00 75.00 3.48% 3.64%
Sugar 690.00 690.00 32.00% 33.46%
Corn Syrup, 42 DE 500.00 410.00 23.19% 19.88%
Water 100.00 95.65 4.64% 4.64%
Hydrogenated Palm Kernel 225.00 225.00 10.43% 10.91%
Oil, 100 mp Omega 3 powder 250.00 250.00 11.59% 12.12%
Malic Acid, Fine Powder 24.00 24.00 1.11% 1.16%
Citric Acid, Fine Powder 6.00 6.00 0.28% 0.29%
Orange Flavor 27.00 27.00 1.25% 1.31%
Oil of Orange Water Soluble 9.00 9.00 0.42% 0.44%
Orange Color, Liquid 12.00 12.00 0.56% 0.58%
Total 2156.50 2062.15 100.00% 100.00%

Specifically, in a mixer bowl with a whip attachment, egg protein was solubilized in the first measure oÃwater. In a separate container, sugar and the first measure of corn syrup was brought to a boil. The boiled syrup was slowly added to the mixer bowl while mixing on low speed. After all syrup had been added, the speed was increased to maximum speed and the mixture was whipped until the volume was at maximum.
In another container, palm oil was melted to clarity and combined with 80% of the omega-3 powder, until thickening began. The resulting paste was stirred until all dry ingredients were evenly coated with fat.
Sugar, the second measure of corn syrup, and water were brought to a boil (126 C). Syrup was slowly poured into the mixer bowl while mixing slowly. The omega-3 paste was added and mixed until even. Acid, the remaining dry omega-3 powder, and flavors were added next and mixed until even. The resulting mixture was poured and formed as a slab on a cool surface. The product was cut and wrapped. The product had a cooked yield of 95.62%.
Example 33: Pasta Pasta (serving size of 150 g) incorporating microencapsulated omega-3 fatty acids (1812 TG powder from Ocean Nutrition Canada, Ltd., Dartmouth, Canada) was prepared according to the formulation in Table 28. The product had a 32 mg dosage of EPA +
DHA per 140 g serving.

Table 28:

Ingredient Weight (g) Percent Durham Wheat Flour 453.60 69.70%
Whole Eggs 120.00 18.44%
Water 75.00 11.52%
Omega 3 2.20 0.34%
Total 650.80 100.00%
Flour and omega-3 powder were mixed together in one container. Eggs and water were combined in a separate container. The wet ingredients were slowly poured into the dry ingredients as they were mixed in a mixer equipped with a dough hook. The resulting dough was kneaded for about 30 seconds. The dough was then covered with plastic wrap and allowed to stand for 45 minutes. The dough was then sheeted into fettuccini sized noodles and dried for from 20 minutes to 1 hour. To cook the noodles, water was brought to a rolling boil and the noodles were added. After 3.5 minutes, the water was drained and the cooked noodles were rinsed under cold water.
Other advantages which are obvious and which are inherent to the invention will be evident to one skilled in the art. It will be understood that certain features and sub-combinations are of utility and may be employed without reference to other features and sub-combinations. This is contemplated by and is within the scope of the claims. Since many possible embodiments may be made of the invention without departing from the scope thereof, it is to be understood that all matter herein set forth or shown in the accompanying drawings is to be interpreted as illustrative and not in a limiting sense.

Claims (66)

What is claimed is:

1. A food article comprising a microcapsule, wherein the microcapsule comprises an agglomeration of primary microcapsules and a loading substance, each individual primary microcapsule having a primary shell, wherein the loading substance is encapsulated by the primary shell, and wherein the agglomeration is encapsulated by an outer shell.

2. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise a surfactant, gelatin, polyphosphate, polysaccharide, or a mixture thereof.

3. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise gelatin type A, gelatin type B, polyphosphate, gum arabic, alginate, chitosan, carrageenan, pectin, starch, modified starch, alfa-lactalbumin, beta-lactoglobumin, ovalbumin, polysorbiton, maltodextrin, cyclodextrin, cellulose, methyl cellulose, ethyl cellulose, hydropropylmethylcellulose, carboxymethylcellulose, milk protein, whey protein, soy protein, canola protein, albumin, kosher gelatin, non-kosher gelatin, Halal gelatin, non-Halal gelatin, or a mixture thereof.

4. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise fish gelatin.

5. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise pork gelatin.

6. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise a gelatin with a Bloom number of from about to about 50.

7. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise a gelatin with a Bloom number of from about 51 to about 300.

8. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise a gelatin with a Bloom number of about 0, about 210, about 220, or about 240.

9. The food article of claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprise a complex coacervate.

10. The food article of claim 9, wherein the complex coacervate is a complex coacervate of gelatin and polyphosphate.

11. The food article of claim 1, wherein the outer shell has an average diameter of from about 1 µm to about 2,000 µm.

12. The food article of claim 1, wherein the primary shell has an average diameter of from about 40 nm to about 10 µm.

13. The food article claim 1, wherein the primary shell, the outer shell, or both the primary and outer shells comprises an antioxidant.

14. The food article of claim 1, wherein the loading substance comprises a biologically active substance, a nutritional supplement, a flavoring substance, a vitamin, a mineral, a carbohydrate, a steroid, a trace element, a protein, or any mixture thereof.

15. The food article of claim 1, wherein the loading substance comprises one or more oils chosen from a microbial oil, algal oil, fungal oil, and plant oil.

16. The food article of claim 1, wherein the loading substance comprises fish oil.

17. The food article of claim 16, wherein the fish oil comprises an Atlantic fish oil, Pacific fish oil, Mediterranean fish oil, light pressed fish oil, alkaline treated fish oil, heat treated fish oil, light and heavy brown fish oil, bonito oil, pilchard oil, tuna oil, sea bass oil, halibut oil, spearfish oil, barracuda oil, cod oil, menhaden oil, sardine oil, anchovy oil, capelin oil, Atlantic cod oil, Atlantic herring oil, Atlantic mackerel oil, Atlantic menhaden oil, salmonid oil, or shark oil.

18. The food article of claim 1, wherein the loading substance comprises an omega-3 fatty acid, and ester of an omega-3 fatty acid, and/or a mixture thereof.

19. The food article of claim 18, wherein the ester of an omega-3 fatty acid comprises an alkyl ester of an omega-3 fatty acid, a monoglyceride of an omega-3 fatty acid, a diglyceride of an omega-3 fatty acid, a triglyceride ester of an omega-3 fatty acid, a phytosterol ester of an omega-3 fatty acid, an ester of an omega-3 fatty acid and an antioxidant, a furanoid ester of an omega-3 fatty acid, and/or a mixture thereof.

20. The food article of claim 1, wherein the loading substance comprises docosahexaenoic acid and/or eicosapentaenoic acid, a C1-C6 alkyl ester thereof, a triglyceride ester thereof, a phytosterol ester thereof, and/or a mixture thereof.

21. The food article of claim 1, wherein the loading substance further comprises a preservative, antimicrobial, chelating agent, thickener, flavoring, diluent, emulsifier, dispersing aid, binder or any mixture thereof.

22. The food article of claim 1, wherein the loading substance is from about 20% to about 90% by weight of the microcapsule.

23. The food article of claim 1, wherein the microcapsule is prepared by a process comprising:
a. providing an emulsion comprising the first polymer component and the loading substance;
b. adding, the second polymer component to the emulsion;
c. adjusting pH, temperature, concentration, mixing speed, or a combination thereof to form an aqueous mixture comprising a primary shell material, wherein the primary shell material comprises the first and second polymer components and surrounds the loading substance;
d. cooling the aqueous mixture to a temperature above the gel point of the primary shell material until the primary shell material forms agglomerations; and e. further cooling the aqueous mixture to form an outer shell around the agglomeration.

24. The food article of claim 23, wherein an antioxidant is added to the emulsion and/or the aqueous mixture.

25. The food article of claim 23, wherein the antioxidant comprises ascorbic acid, citric acid, or a salt thereof.

26. The food article of claim 23, wherein cooling is at a rate of about 1°C per about 1 to about 100 minutes.

27. The food article of claim 23, wherein cooling is at a rate of about 1°C/5 minute.

28. The food article of claim 23, wherein the mixture is cooled until it reaches a temperature of from about 5°C to about 10°C.

29. The food article of claim 23, further comprising step (e) adding a cross-linker to cross-link the shell material.

30. The food article of claim 29, wherein the cross-linker is an enzymatic cross-linker, an aldehyde, tannic acid, alum, or a mixture thereof.

31. The food article of claim 29, wherein the cross-linker is gluteraldehyde.

32. The food article of claim 29, wherein the cross-linker is transglutaminase.

33. The food article of claim 23, further comprising step (f) drying the microcapsules.

34. The food article of claim 33, wherein the microcapsules are spray dried.

35. The food article of claim 1, wherein the food article is a wet soup.

36. The food article of claim 1, wherein the food article is a dehydrated and culinary food.

37. The food article of claim 1, wherein the food article is a beverage.

38. The food article of claim 1, wherein the food article is a frozen food.

39. The food article of claim 1, wherein the food article is a seasoning.

40. The food article of claim 1, wherein the food article is apple sauce.

41. The food article of claim 1, wherein the food article is baby food.

42. The food article of claim 1, wherein the food article is a breaded meat.

43. The food article of claim 1, wherein the food article is a pasteurized process cheese food.

44. The food article of claim 1, wherein the food article is a granola bar or cereal bar.

45. The food article of claim 1, wherein the food article is a bread, cereal, or waffle.

46. The food article of claim 1, wherein the food article is soymilk.

47. The food article of claim 1, wherein the food article is a gummy candy.

48. The food article of claim 1, wherein the food article is a pasta or pasta sauce.

49. The food article of claim 1, wherein the food article is a tomato sauce.

50. The food article of claim 1, wherein the food article is orange juice.

51. The food article of claim 1, wherein the food article is a snack food.

52. The food article of claim 51, wherein the snack food is a potato chip, corn chip, or tortilla chip.

53. The food article of claim 1, wherein the food article is a chip and the loading substance comprises an omega-3 fatty acid.

54. The food article of claim 53, wherein the microcapsule is present at less than or equal to about 6% by weight, based on the total weight of the chip.

55. The food article of claim 53, wherein the microcapsule is present at less than or equal to about 5% by weight, based on the total weight of the chip.

56. The food article of claim 53, wherein the microcapsule is present at from about 1% to about 4% by weight, based on the total weight of the chip.

57. The food article of claim 1, further comprising a probiotic.

58. A method of delivering a loading substance to a subject, comprising administering to the subject the food article of any of claims 1-56.

59. A process for preparing the food article or claims 1-30, comprising mixing the microcapsule with one or more ingredients used to prepare the food article prior to preparing the food article.

60. A process for preparing the food article of claims 1-56, comprising contacting the food article with the microcapsule.

61. The process of claim 60, wherein the microcapsule is blended with a seasoning for the food article.

62. The process of claim 60, wherein contacting the food article with the microcapsule is accomplished by spraying the microcapsule onto the food article.

63. The process of claim 60, wherein contacting the food article with the microcapsule is accomplished by mixing the food article with the microcapsule.

64. A food article comprising a microcapsule, wherein the microcapsule comprises a loading substance, a primary shell, and a secondary shell, wherein the primary shell encapsulates the loading substance, and the secondary shell encapsulates the loading substance and the primary shell.

65. A food article comprising a microcapsule, wherein the microcapsule comprises a omega-3 oil.

66. The food article of claim 65, wherein the omega-3 oil is a docosahexaenoic acid and/or eicosapentaenoic acid, a C1-C6 alkyl ester thereof, a triglyceride ester thereof, a phytosterol ester thereof, and/for a mixture thereof.