PH27116A - Food flavoring high-note enhancement by microbead delivery - Google Patents

Food flavoring high-note enhancement by microbead delivery Download PDF

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Publication number
PH27116A
PH27116A PH39967A PH39967A PH27116A PH 27116 A PH27116 A PH 27116A PH 39967 A PH39967 A PH 39967A PH 39967 A PH39967 A PH 39967A PH 27116 A PH27116 A PH 27116A
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Philippines
Prior art keywords
food product
beads
flavoring
food
microbeads
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PH39967A
Inventor
Steven E Zibell
Lindel C Richey
Michael J Greenberg
David Witkewitz
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Wrigley W M Jun Co
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Publication of PH27116A publication Critical patent/PH27116A/en

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00Chewing gum
    • A23G4/06Chewing gum characterised by the composition containing organic or inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00Chewing gum
    • A23G4/18Chewing gum characterised by shape, structure or physical form, e.g. aerated products
    • A23G4/20Composite products, e.g. centre-filled, multi-layer, laminated
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L13/00Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/428Addition of flavours, spices, colours, amino acids or their salts, peptides, vitamins, yeast extract or autolysate, nucleic acid or derivatives, organic acidifying agents or their salts or acidogens, sweeteners, e.g. sugars or sugar alcohols; Addition of alcohol-containing products
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52Adding ingredients
    • A23L2/56Flavouring or bittering agents
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/74Fixation, conservation, or encapsulation of flavouring agents with a synthetic polymer matrix or excipient, e.g. vinylic, acrylic polymers
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L9/00Puddings; Cream substitutes; Preparation or treatment thereof
    • A23L9/10Puddings; Dry powder puddings

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Confectionery (AREA)

Description

_R7116 -1-
FOOD FLAVORING HIGH-NOTE ENHANCEMENT
BY MICROBEAD DELIVERY
BACKGROUND OF THE INVENTION :
This invention relates in general to food flavoring, and in particular to foods prepared such that "high-note" flavors are enhanced. © Food flavorings are very complex chemically. Many food flavorings are oily substances that include complex mixtures of compounds that have varying degrees of volatility. Each mixture essentially has its own i signature identified by the types, relative amounts, and volatility of its component compounds.
Unfortunately, food processing, transportation, and storage involves subjecting foods to sufficient - 15 heat that can drive off the most volatile fractions of flavoring. The most volatile fractions of a flavoring : are typically the "high-notes" or "low boiler" fractions. Once the high notes are reduced or eliminated in a food flavoring, the flavoring or food containing the flavoring typically tastes noticeably different. In some cases, the flavoring is unrecognizable.
An example will illustrate the point. Many flavorings are spray-dried, that -is, they are dissolved in a gelatinous matrix (e.g. in gum arabic and starch) and the mixture is sprayed thorough an orifice to dry - of f the water. A dry particulate material containing the flavoring is the result. An unintended result is : that at least some of the high notes in the flavoring are volatilized during spray-drying.
Still another problem with some food flavorings is shelf-life. Some flavorings oxidize over time so they no longer impart the desired flavor to the food even
ST
27116 7" . - 2 - ; though the food is otherwise acceptable. Other flavorings can react with other food ingredients over time with the same loss of food flavor.
Efforts have been made to extract high notes from foods or flavorings prior to food processing and add the high notes back to the food after processing.
However, such procedures do not solve problems of volatilization of high notes or oxidation or reactions of food flavorings during storage.
SUMMARY OF THE INVENTION
According to the current invention, a food product has dispersed in it water-insoluble, porous polymeric beads that have microporous passages in them impregnated with one or more food flavorings containing volatile substances. In narrower aspects of this . invention, the beads are coated with water-soluble - coatings to entrap the flavorings in the beads until ‘ i the beads are exposed to water. Alternatively, the beads can be coated with a coating that melts when heated so that the flavoring will not be released until the food is heated. Because the beads of this - invention are polymeric, they exhibit an affinity toward food flavoring oils that retards the volatilization of the high notes. In addition, the entrapment of the food flavoring in the microporous passages reduces the exposure of the flavoring to
Co oxidants and to other substances in the food that may react with the flavoring during storage.
DESCRIPTION OF THE PRESENTLY PREFERRED EMBODIMENTS OF THE INVENTION
In the present invention, a food product (or matrix) contains porous polymeric beads that have os ot oo «(116 A" -3- ~=2, . microporous passages impregnated with flavoring agents. The flavoring agents may comprise essential oils, synthetic flavors, or mixtures thereof, including but not limited to, oils dried from plants and fruits such as citrus oils, fruit essences, peppermint oil, spearmint oil, clove 0il, oil of wintergreen, anise, and the like. Artificial flavoring components are often included. Those skilled in the art will recognize that natural and artificial flavoring agents may be combined in any sensorially acceptable blend.
All such flavors and flavor blends are contemplated by the present invention.
By "food product" or "food matrix" is meant an edible substance that delivers nutrition or taste pleasure to humans or other animals. Food matrices include any foods that have typically had their taste . enhanced by the addition of flavoring agents. Food matrices include but are not limited to meats, baked } goods (i.e. breads, cakes, cookies, and pies and the like), puddings, syrups, gums, and the like. Food matrices also include dry or condensed mixes that upon addition of water or other ingredients form an edible substance that can be eaten immediately or eaten after cooking or further processing. Mixes include baked good mixes, soup mixes, pudding mixes, and the like.
Food matrices also include liquid beverages and concentrates for liquid beverages. With liquid
Lo beverages or concentrates, the porous polymeric beads containing flavorings can be added to the liquid im- mediately before the product is packaged so the "high notes" will not be lost. The flavoring is released to the drink from the beads during storage and shipment of the product. This release can be delayed by using a water-soluble coating that dissolves over time.
: : | Hl & a 27116
Food matrices also include powdered or oF granular mixes for liquid beverages that are mixed with water to produce liquid beverages. A powdered or granular beverage mix usually includes a beverage base : 5 that ordinarily has flavoring (e.g. coffee or citrus flavor) and often a sweetener and the like. Beverage bases are known in the art and include instant coffee, milk shakes, fruit drinks, and the like. The flavor- impregnated microbeads of this invention can be coated with a water-soluble coating that dissolves to release flavoring upon addition of water to the mix (.e.g. a cocoa, chocolate or fruit flavor delivered to the water by beads). Alternatively, the beads can be coated with a coating (e.g. fat) that melts when hot water is added, a feature desirable in hot drink mixes such as cocoa or coffee. .
In making syrups, the process involves - boiling a juice (e.g. a fruit juice or a maple tree gap) to drive off water. In the process "high notes" are lost. These "high notes" can be distilled from the vapors generated during boiling, absorbed into microbeads that are then coated, and the microbeads can be added back to the syrup.
The present invention contemplates the addi- tion to a food matrix described above of water-insoluble porous polymeric beads preferably of size not discernible to the consumer where the beads have microporous passages impregnated with one or more flavorings described - above. The preferred size range is between 10 and 100 microns, and the most preferred is between 20 and 50 microns. Preferably, the porous polymeric beads are coated with a coating that influences the release of the flavoring oils within the microporous passages in the porous polymeric beads. Such coatings include zein, wax, gum arabic, fatty acids, fats, a food-grade shellac, carbohydrates, silica, water-insoluble polymers (e.9., polyvinyl acetate), proteins such as casein, starches, dextrins, or modified
} . 9 71 6 fle or unmodified cellulosics such as ethyl, methyl, hydroxy- propyl or hydroxyethyl cellulose. The use of such coated beads controls the release of the flavoring oil high notes in the porous polymeric beads, typically such that the ingredients within the beads are released at a time when the food product is used by the consumer.
The present invention also contemplates the addition of other food additives together with flavorings to microbeads. For example, anti-oxidant compounds such as BHT and BHA can be mixed with a flavoring oil, and- the mixture impregnated into microbeads. The anti-oxidant and the location of the flavoring oil in the microbeads will retard oxidation of the flavoring oil. Oxidation is a particular problem with some flavoring oils such as peppermint oil because oxidation can cause the flavor to change. The ~ location of the flavoring oil in the microporous ) passages reduces exposure to oxygen. The addition of an anti-oxidant enhances the preservation of the flavoring. One advantage is that anti-oxidant can be targeted to the flavoring oil, and need not be in high concentration throughout the food.
The polymeric beads of this invention are polymerized in such a fashion that the microporous passages are formed during polymerization. Such a procedure is described below. Residual monomer is then extracted as described below so that the particles can _ be impregnated with flavoring oils or components thereof. The beads are then optionally coated with one or more coatings and added to the food matrix. The details of microparticle polymerization, monomer extraction and microparticle impregnation and coating are described below, followed by Examples I through XIV that illustrate various specific foods and polymeric beads of the current invention.
< : / 1 2906 16 at 1. POLYMERIC BEAD POLYMERIZATION
In one embodiment of the present invention, the polymeric beads can be polymerized as taught in
U.S. Patent 4,690,825 to Won dated September 1, 1987, the entire disclosure of which is incorporated herein by reference. Specifically, the beads used in the food matrix of the present invention can be prepared by polymerizing one or more polymers by a free radical suspension polymerization process. A monomer or pair of comonomers is dissolved in an inert porogen to form a solution that is suspended in a phase or solvent incompatible with that solution. Such a phase or solvent can be water with stabilizing additives. After the solution is suspended in the phase, the solution and phase are agitated to form droplets of solution suspended in the phase. After the formation of the droplets, the monomer or monomers in the droplets are activated to initiate a polymerization reaction in which the monomer is cross-linked or where two or more monomers are polymerized to form porous beads having a network of pores with the porogen within the network of pores. The activation may be triggered by an initiator that is insoluble with the monomer solution. Alterna- tively, activation may be triggered by an energy source such as radiation. The inert porogen serves as an internal diluent during polymerization and introduces the desired sponge-like microporous structure or network of pores into the finished bead. The inert ” porogen does not react with the monomer present during polymerization or inhibit the polymerization. The bead may or may not swell in the inert porogen. After formulation of the porous beads, the beads are separated from the phase and subjected to one or more extraction steps such as washing to remove any unreacted monomer or impurity from the beads. After
Co 27116 99liG - 7 - = } extraction, described below, the beads may be dried to obtain a powder-like substance that includes the beads put without either porogen or solvent.
An example of a polymer that can be used to form porous polymeric beads for the food product of this invention is a copolymer of divinylbenzene and styrene. Such beads can be polymerized in water as taught in the aforesaid Won patent or as described in
Example I below. If such a copolymer is used, monomers (nonfood approved additions) are typically not com- pletely reacted, and excess monomer concentration should be reduced to levels less than 30ppm [as illustrated by the styrene monomer standards for food-grade styrene-butadiene rubber (Food Chemical Codex, 3rd Edition, pg. 42.)] if the beads are to be used in a food product. Typically, the amount of free cross . linking agent (divinylbenzene) in the beads after poly- . merization is quite low compared with styrene because divinylbenzene has two reaction sites, and thus is more reactive than styrene. Thus, the extraction is primarily to extract styrene monomer, the divinylbenzene monomer present in the polymer already being close to or lower than the 30ppm value. An extraction procedure is ex- plained in Section 11 below and in Example I.
To avoid or reduce the effort required in monomer extraction, one can copolymerize divinylbenzene with a food-grade monomer that can polymerize with
Bn divinylbenzene. By a food-grade monomer is meant any monomer that is a food additive permitted for direct addition to food for human consumption under 21 CER, part 172 or substances generally recognized as safe under 21 CFR, part 182. Examples of such monomers are one or more of the following: estragole, limonene, carvone, eugenol and ocimene. Limonene is illustrative inasmuch as it is a naturally-occurring compound in oo | 27116 =m - 8 - Co many citrus fruits. Still other examples are provided in Example V, infra.
The food-grade monomer need not be extracted unless one wants to extract it for flavor reasons. But in many instances, the food-grade monomer may enhance ‘the flavor of the food. Thus, any extraction of ‘monomer after polymerization may only have to focus on divinylbenzene reduction, a comparatively simple proposition because it is already in comparatively low concentration.
I1. MONOMER EXTRACTION
If monomer extraction is desired or required, it can be accomplished by washing the beads first with water followed by several (preferably three) washings of isopropanol, four to five washings with acetone and . four to five washings with hexane. The excess solvent is removed by evaporation under a nitrogen blanket to leave dry beads having a powder-1like consistency.
III. POLYMERIC BEAD IMPREGNATION WITH
FOOD FLAVORING COMPONENTS
The impregnation of the pores in the polymeric beads with food flavoring components can be accomplished by soaking the beads in an equal or greater weight of the flavoring component so that the beads are completely immersed. The impregnation proceeds over a period of at least six and preferably - 48 hours. The impregnation may be carried out at reduced temperature if stability or volatility of the flavoring is a particular concern. Of the total dry weight of the loaded peads after impregnation, 607 or even more may be active ingredient. Such loadings are possible using this procedure, although some bead/active agent combinations will yield lower loadings.
Lo 296 ,.. R116
In some cases, pretreatment of the flavoring may be desirable. For example, if the flavoring is a solid, it must first pe dissolved, suspended or slurried in a liquid carrier before impregnation. If a liquid flavoring is viscous, dilution may be desirable before impregnation.
Some flavors may have sufficiently low viscosities for easy impregnation, but the low viscosity may lead to loss of the flavoring from the porous microbead during subseguent handling and/or storage of the food product. In such cases it may be desirable to increase viscosity before or after impregnation. This may be accomplished by gellation, coagulation, precipitation, or through use of thickeners.
Yet another embodiment is the use of meltable active agents or carriers. In such cases, impregnation is carried out at a temperature above the melting point of the active agent or carrier/active agent blend.
After impregnation, excess meltable ingredient is removed and the beads are cooled to incorporate the active agent into the beads. 1V. POLYMERIC BEAD COATING
As indicated above, the porous polymeric beads are preferably coated with a coating that retards the release of the flavoring from the pores of the beads or prevents premature release during storage. ) Illustrative coatings include water-soluble or permeable compositions such as hydroxypropyl methyl- cellulose, sugars, and the like. Depending on the thickness and porosity of the water-soluble or permeable coatings, such coatings retard the release of the flavoring in the pores of the polymeric beads by
} 271 <e 16 —- 10 ~- first requiring the coating to dissolve before the flavoring is released.
Water—insoluble coatings may also be employed.
Such coatings include food-grade shellac as disclosed in
U.S. 4,673.577 to Patel dated June 16, 1987 that is incorporated herein hy reference. Water—insoluble wax coatings also include waxes such ag those disclosed in
United States Patent Number 4,885,175 - Zikell issued
December 5, 1989 which is incorporated herein by reference, and Zein.
Fatty acids can also be employed as coatings for fhe beads. Fatty acids, depending upon chain length. have varying walter colubilities. A mixture of fatty } acids can be prepared that has the desired degree of water solubility that controls the dissolution of the coating until the desired time. Combinations or mixtures of various water-soluble and water—insoluble coating agents may be employed as coatings for the porous heads to control the release of the flavoring fron the beads.
In some applications, it is advantageous to have coatings that melt when heated. For example in hot drink mixes such as coffee or cocoa mixes, beads containing chocolate flavoring. for example, can be
Bn 25 coated with a fat that melts when hot water is added.
In baking mixes. the flavoring is release from the beads when a coating is melted. Such coatings are those that melt at temperatures above 300C, preferably above 1009C. The preferred coatings are fats. 1 is also possible to have different popula- tions of beads within the food, each population ccated wilh a different coating having a different water solu- hility or melting point than the other populations. or oo 27116 DHL - 11 - one or more populations being left uncoated while one or more populations are coated with various coatings having different solubilities or melting points. One after another, the various populations will release their active ingredients to extend the overall time of . release greatly. The prolonged release of flavoring is useful, for example, in baked goods that release volatile flavor/aroma compounds during baking. A variety of methods to coat the beads can be used.
Several are described generally below, and in detail in the Examples, infra.
A. Spray Drying
An emulsion/solution of flavoring-impregnated peads and encapsulant is atomized into an air stream that evaporates the solvent to leave coated beads. A Niro spray dryer may be used. This technique should be used only where it does not allow substantial amounts of the high notes in the flavoring to volatilize. It is believed to be a workable technique in some cases because certain flavors are entrapped in the passages in the beads. In addition, exposure of the microparticles to air is very brief, and not much flavor is lost.
B. Spray Chilling
A suspension of beads in molten encapsulant is bo atomized and chilled to produce beads coated with encapsulant.
C. Fluid Bed Coating
Beads are suspended in an air stream (fluidized bed). The beads are sprayed with a solution of the encapsulant in a volatile solvent. The solvent is evaporated or dried by the air stream to produce beads coated by the encapsulant.
Lo 27114 26 - 12 - : D. Granulation/Agglomeration
A damp mix of beads and granulant is prepared, then dried and ground to desired particle size.
E. Gel Encapsulation
Beads are suspended in a gelatin solution that is cooled to gel, then ground to desired particle size.
F. Melt Blending ~ Beads are mixed into a molten agglomerant which is cooled to harden and ground to the desired particle size.
The following examples of the invention are provided by way of explanation and illustration. They are not intended to limit the invention.
Example 1
Peppermint Non-Tack Gum - A) Preparation of Microbeads
Gelatin (250 mg) is added to a three-necked flask purged with nitrogen. Water (150 ml) is heated to 50°C and added to the flask to dissolve the gelatin.
While the contents of the flask are stirred, a freshly prepared solution of benzoyl peroxide (1.25 grams; 1.03 mmole) and styrene (22.9 grams; 0.22 mole) monomer is added, followed by divinylbenzene (12.0 grams; 42 mmoles). The mixture is heated to 90°C while maintaining a constant stirring rate, and passing : - nitrogen through the flask. = The mixture is stirred for two hours, and cooled to room temperature, and the supernatant liquid is decanted. The polymer beads are washed with hexane several times, and stirred in hexane (200 ml) for two hours to remove any excess divinylbenzene or styrene, and dried overnight at 50°C in a vacuum to yield dry microbeads.
Lo 2 7 » Hits 0 - 13 =~
B) Impregnation of Microbeads with Peppermint Oil
A solution of 50% peppermint oil and 50% of a 2% aqueous solution of egg albumin is mixed vigorously to disperse the peppermint oil in the water. Micro- beads from part A are mixed with an equal weight of this solution for six hours. Excess solution is removed by filtration or centrifugation. The mixture is warmed to about 50-75°C to coagulate the solution.
The resulting beads will contain approximately 25% peppermint oil by weight.
C) Preparation of Gum Base
A gum base set forth in Table 1 below is prepared as described in U.S. Patent No. 3,984,574.
Table I _ Parts
Ingredient by Weight
Polyvinyl Acetate 27.36
Hydrogenated Soybean Oil 17.76
Partially Hydrogenated Vegetable 0il 10.56
Calcium Carbonate 14.40
Polyisobutylene (Molecular
Weight 6-12 M) 20.28
Isobutylene-isoprene Copolymer 10.80
Mono and Diglycerides of Fatty Acids 2.04
Hydrogenated Cotton Seed Oil 16.80
Specifically, the polyvinyl acetate, polyiso- butylene, and the isobutylene-isoprene copolymer are melted, and added to a mixer. Then the fatty acids, . oils, and remaining ingredients are added and mixed until the mixture is well mixed.
C) Preparation of Feppermint Gum
To the base of part B, sugar, 45° Be' corn syrup, glycerin, peppermint oil, and microbeads from
9 ole 4 1 1 - - 14 - * 0 part B are added in the proportion by weight set forth in Table II.
Table 11
Percent
Ingredient by Weight
Base 20.0
Sugar 58.9 45° Be' Corn Syrup 17.4
Glycerin 0.7
Peppermint Oil 0.6
Microbeads 2.4
Example II
Spearmint Sugarless Gum
A) Preparation of Microbeads
Gelatin (250 mg) is added to a three-necked flask purged with nitrogen. Water (150 ml) is heated ' to 50°C and added to the flask to dissolve the gelatin.
While the contents of the flask are stirred, a freshly prepared solution of benzoyl peroxide (1.25 grams; 1.03 mmole) and ocimene (29.92 grams; 0.22 mole) monomer is : added, followed by divinylbenzene (12.0 grams; 42 mmoles). The mixture is heated to 90°C while main- taining a constant stirring rate, and passing nitrogen : through the flask.
The mixture is stirred for two hours, and cooled to room temperature, and the supernatant liquid is decanted. The polymer beads are washed with hexane to several times, and stirred in hexane (200 ml) for two hours to remove any excess divinylbenzene, and dried overnight at 50°C in a vacuum to yield dry microbeads.
B) Impregnation of Mi crobeads with Spearmint Oil
Spearmint oil and a 2% aqueous solution of guar gum are mixed vigorously at a 50:50 ratio by volume so that the oil is dispersed throughout the guar gum solution. The microbeads from part A are mixed in the spearmint oil/guar gum mixture for 24 hours. The mixture is cooled so that it gels.
Cc) Preparation of Spearmint Gum
LADCO Astro Base (A) 2031, a commercially available gum base from the L.A. Dreyfus Company of
Edison, New Jersey, is mixed with an aqueous solution of 70% sorbitol, crystalline sorbitol, glycerin, spearmint oil, and microbeads from part B of this example according to the proportions in Table 111 to produce a spearmint gum that is rolled into sheets and cut into pieces.
Table III
Percent
Ingredient by Weight - LADCO Astro Base (A) 2031 25.0 70% Sorbitol Solution 15.0
Sorbitol 51.3
Glycerin 5.0
Spearmint Oil 1.3
Microbeads 2.4
Example II11
Sugared Cherry Gum
A) Preparation of Microbeads
Gelatin (250 mg) is added to a three-necked flask purged with nitrogen. Water (150 ml) is heated to 50°C and added to the flask to dissolve the gelatin. - While the contents of the flask are stirred, a freshly prepared solution of benzoyl peroxide (1.25 grams; 1.03 mmole) and limonene (30 grams; 0.22 mole) monomer is added, followed by divinylbenzene (12.0 grams; 42 mmoles). The mixture is heated to 90°C while maintaining a constant stirring rate, and passing nitrogen through the flask.
: : 2 4 1 Hie ’r - 1 = - 16 - L
The mixture is stirred for two hours, and cooled to room temperature, and the supernatant liquid is decanted. The polymer beads are washed with hexane several times, and stirred in hexane (200 ml) for two hours to remove any excess divinylbenzene and dried overnight at 50°C in a vacuum to yield dry microbeads.
B) Impregnation of Microbeads With Cherry Flavoring : A wax (melting point 115°F) is melted and mixed with a cherry flavoring in a ratio of 25% wax and 75% flavoring by weight. Microbeads from part A are added in equal weight to the molten wax, allowed to set for six hours, and excess wax is removed. The mixture is cooled to leave finely divided microbeads impregnated with cherry flavor and coated with wax.
Cc) Preparation of Cherry Gum
LADCO Bubble Base T 2198, a commercially available gum base available from L.A. Dreyfus Company, is mixed with 43° Be' corn syrup, sugar, glycerin, cherry flavor, and microbeads from part B above according to the proportions in Table 1V to produce a cherry-flavored gum that is rolled into sheets and cut into pieces. : ’
Table IV
Co Percent
Ingredient by Weight
LADCO Bubble Base T 2198 20.0 43° Be' Corn Syrup 25.0
Sugar 52.7
Glycerin 0.5
Cherry Flavor 0.6
Microbeads 1.2 co 2 2ille no =7116
Example IV
Peppermint Sugar Stick Gum
A) Preparation of Microbeads
Gelatin (250 mg) is added to a three-necked flask purged with nitrogen. Water (150 ml) is heated to 50°C and added to the flask to dissolve the gelatin. :
While the contents of the flask are stirred, a freshly . prepared solution of benzoyl peroxide (1.25 grams; 1.03 mmole) and eugenol (36.1 grams; 0.22 mole) monomer is added, followed by divinylbenzene (12.0 grams; 42 mmoles). The mixture is heated to 90°C while maintaining a constant stirring rate, and passing nitrogen through the flask.
The mixture is stirred for two hours, and cooled to room temperature, and the supernatant liquid is decanted. The polymer beads are washed with hexane several times, and stirred in hexane (200 ml) for two hours to remove any excess divinylbenzene, and dried overnight at 50°C in a vacuum to yield dry microbeads.
B) Impregnation of Microbeads with Peppermint Flavor
The procedure of Example I, part B is repeated using the microbeads of part Ih of this example to obtain microbeads impregnated with peppermint flavor. .
Cc) Preparation of Peppermint Sugar Stick Gum - LADCO Paloja® Base, a commercially available gum base from The L.A. Dreyfus Co., is mixed with 45° ’
Be' corn syrup, sugar, glycerin, peppermint oil and microbeads from part B in the proportions set forth in
Table V below, to produce a peppermint sugar stick gum.
- | S21 G
R114 1a 0
Table V
Percent
Ingredient by Weight
LADCO Paloja® Base 19.4 45° Be' Corn Syrup 19.8
Sugar 58.2
Glycerin 0.5
Peppermint Oil 0.7
Microbeads 1.4
Example V
Alternative Microbead Formulations
Various microbead polymers are possible con- sistent with the teachings of this invention. A number : of types of microbeads can be prepared following the procedure set forth in Example 11I part A, altering the amount of monomer to be polymerized wilh divinylbenzene, or changing the monomer to be -- polymerized with divinylbenzene. Alternatively, the amount of divinylbenzene can be varied. A summary of such microbead formulations is set forth in Table VI below.
Table VI
Divinylbenzene
Monomer Monomer Amount Amount a) Estragole 32.6 g; 0.22 mole 33 9 b) Estragole 32.6 g; 0.22 mole 98 g
Cc) Allyl cyclo- hexyl pro- — pionate 43.12 g; 0.22 mole 12 g d) Allyl cyclo- hexyl pro- pionate 43.12 g; 0.22 mole 33 9 e) Allyl cyclo- hexyl pro- pionate 43.12 g; 0.22 mole 97 g £) Ocimene 29.92 g; 0.22 mole 12 9 oo 27] je
So 16 ’ . —_— !
LOTS, : Table VI Cont'd
Divinylbenzene
Monomer Monomer Amount Amount g) Ocimene 29.92 g; 0.22 mole 33 g h) Ocimene 29.92 g; 0.22 mole 97 g i) Divinyl- : sulfide 18.96 g; 0.22 mole 12-97 ¢ 3) Vinyl . methylketone 15.42 g; 0.22 mole 12-97 g¢ k) 4-methyl-5-vinyl thiazole 27.5 g; 0.22 mole 12-97 ¢ 1) 2-methyl-5-vinyl pyrazine 26.1 g; 0.22 mole 12-97 g m) Vinyl pyrazine 23.32 g; 0.22 mole 12-97 g¢ n) 1-penten-3-o0l 18.92 g; 0.22 mole 12-97 9 0) 1-octen-3-o0l 28.16 g; 0.22 mole 12-97 g
Pp) carvone 33.00 g; 0.22 mole 12-97 g q) limonene 29.92 g; 0.22 mole 12-97 g r) diallyl- disulfide 32.18 g; 0.22 mole 12-97 4g s) allylsulfide 25.13 g; 0.22 mole 12-97 g t) allyl al- . pha ionone 51.12 g; 0.22 mole 12-97 g
The monomers identified above to be polymer- -~ ized with divinylbenzene can also be combined with styrene to yield the desired beads. In addition, divinylbenzene can be replaced with allylacrylate as the crosslinker or with other suitable divinyl com- pounds.
Microbeads produced from the polymers de- scribed above are made from food-grade monomers that can polymerize with divinylbenzene. The residual
‘ ’ 2 7 2H - 20 - 1 1 6 food-grade monomer in the microbeads can contribute flavor to the food. Accordingly, to achieve a proper blend of food-grade monomer with the flavoring of the food to achieve good taste, certain combinations of food-grade monomer and food flavorings are preferred, as indicated in Table VII below.
Table VII
Gum Flavoring Monomer(s})
Mint Estragole, ocimene, vinyl- methyl ketone, 1~octen-3-01, l-penten-3-0l1, carvone, limonene, allyl alpha ionone
Onion Divinylsulfide, diallyldisulfide, allylsulfide
Citrus Ocimene, carvone, limonene
Peanut 4-methyl-5-vinylthiazole, 2-methyl-5-vinylpyrazine, vinylpyrazine
Meat 4-methyl-5-vinylthiazole, 2-methyl-5-vinylpyrazine, vinylpyrazine, diallyldisulfide, allylsulfide
Fruit Eugenol, allylcyclohexyl propinate, limonene
Cinnamon Estragole, eugenol, limonene
So The polymerized food-grade monomer also forms
Co a polymer with regions that have an affinity toward certain flavorings that can be absorbed into the microbeads. This can improve the impregnation of the microbeads into the pores of the polymeric beads.
These regions are essentially polymeric chains of food-grade monomer. 1f the flavoring agent can dissolve into or has an affinity toward the food-grade monomer, the flavoring agent will likely have an affinity toward the polymeric chains in these regions.
‘ Cl 27 SFG cm 116
Example VI
Menthol Chewing Gum Containing Microbeads
Made from Block Copolymers of Styrene and Butadiene
A) Preparation of Microbeads
The flexibility or sponginess of the microbeads can be controlled by forming the microbeads from block copolymers of styrene and butadiene.
Copolymers of styrene and butadiene can be polymerized as di-block copolymers, tri-block copolymers, and tetra-block copolymers by varying the proportions of styrene and butadiene in the reaction mixture, as is known in the block copolymer art. The advantage of block copolymers of styrene and butadiene is that gum active ingredients in the microbeads will diffuse into the rubbery domains. in the microbeads, resulting in slower release of gum active ingredients. The beads he can also be made more crack resistant than styrene- divinylbenzene beads.
Beads of styrene and butadiene block copolymers are made by dissolving such a block copolymer (5 g Kraton D1101 from Shell Chemical
Company) in toluene (150 g). In a separate beaker, polyvinylalcohol (1.5 g) is dissolved in water (450 9g) at about 40°C. The block copolymer solution is mixed with styrene monomer (90 g), and divinylbenzene monomer (45 g) and benzoyl peroxide (1.5 g) arc added to the mixture, and the mixture is agitated at room tem- perature. The mixture with block copolymer is added to the polyvinylalcohol solution, and the combined mixture is agitated with a motor-driven propeller.
The mixture is heated to 80-90°C for at least four hours during which time it is agitated. The mixture is cooled, and filtered to remove the beads.
- 22 - 1 1 6 Zhe
B) Impregnation of Beads with Menthol
Menthol is dissolved in molten wax (melting point 95°F) in a 75% menthol - 25% wax ratio. The molten mixture is mixed well, and an equal weight of microbeads from part A are added. The excess WaX is removed, and the beads are cooled. c) Preparation of Menthol Gum
A menthol gum is prepared using the gum base of Example 1V, part C, the microbeads of part B are used instead of the microbeads of Example iv, part B.
Example VII
Red Cherry/Grape Chewing Gum
A) Preparation of Microbeads
Microbeads are prepared as taught in ] Example I, part A.
B) Impregnation of Microbeads
Half of the beads in part A is impregnated with grape flavor using the method of Example III, part
B using grape flavoring instead of the cherry flavor of
Example 11I, part B. The latter half of the microbeads is added to an equal weight of a solution containing 5% : 25 blue dye FD & Cc #1 in water, and allowed to remain in the solution for six hours. Excess sclution is removed by filtration, and the beads are dried.
C) Coating of Microbeads :
All the beads are then fluidized-bed coated with shellac/ethanol solution (70% beads/30% shellac dry basis).
D) Gum Preparation
Bubble gum is prepared as in Example III, part C except microbeads of part C are used at 2.0% and
2 71 1 6 JfHL - 21 - sugar at 51.9%, and 100ppm FD & C red #40 lake is added. The gum includes cherry flavor as in
Example III, part C. The gum will initially be cherry flavored and change to purple grape upon chewing when the cherry flavor is extracted from the gum base and the microbeads yield the grape flavor and blue color.
Example VIII
Peppermint Non-Tack Gum with Coated Microbeads
The procedure of Example 1 is repeated, except that the microbeads of part B are coated with a gelatin coat as follows. A mixture (by weight) of 10% of the microbeads, 30% 300 Bloom gelatin, and 60% water . is prepared where the water is heated to 63°C prior to the addition of the gelatin and microbeads. The mixture is then cooled so that it gels, and the gel is
Co ground to produce coated microbeads. The coated . microbeads are then formulated into a gum as described in Example I, part C.
Example IX
Tabletted Peppermint Mints
Microbeads prepared as described in
Example 1, parts A and B impregnated with peppermint oil are formulated into a mixture in the proportions set forth in Table VIII.
Table VIII
Tablet Formula
Percent by Weight Grams
Sorbitol 1C1 834 97.5 62.9
Microbeads 0.8 0.5
Magnesium Stearate 0.9 0.6
Talc 0.8 0.5
The sorbitol (ICI 834 available from ICI Incorporated of Delaware) and microbeads are mixed for 15 minutes.
—_—————eeeeeeeeeeeee ee —mmmm y 6 2 q{ 1 1 | 9 4 1 JIG or 1 4
The magnesium stearate and talc are added, and the composition is mixed for five more minutes. The mix can then be tabletted into a mint in a conventional fashion.
The tabletted mint can also be prepared as taught above by replacing the sorbitol with sugar.
Example X
Acidified Smoked Meats
A) Preparation of Microbeads Impregnated With citrus Flavor
Microbeads are prepared as described in
Example 1, part A. The beads are impregnated with an equal weight of an acidic solution of citric acid and ascorbic acid as taught in Section 111 above. The microbeads are spray-chilled coated with a fat having a solid fat index such that the fat will melt over a range of temperatures normally encountered during smoking of meats.
B) Preparation of Meat Emulsion
The microbeads of part A are dispersed in the fat phase of a meat emulsion of frankfurter, salami, bologna, liver sausage, head cheese or the like. The emulsion is stuffed and linked into a natural or cellulosic casing. The links are cooked by either immersion in boiling water or cooking in a smoke house.
The microbeads allow the gradual release of the acids : for controlled acidification of the meant, avoiding premature coagulation of the meat proteins.
Example XI
Butter Flavored Refrigerator Bread Dough
A) Preparation of Butter-Impregnated Microbeads
Microbeads prepared as described in Example 33 I part A are impregnated with concentrated butter extract (having 0.1% ginger oil added to it) by immersing the beads in the extract for six hours. The oo | 27116 one - 25 - : .. ‘ microbeads are filtered from the excess extract, and coated with a high melting point (50 ¢) fat by spray chilling.
B) preparation of Refrigerator Bread Dough
The ingredients in Table IX below are combined in a conventional manner and allowed to rise. when the loaf doubles, one part of the microbeads from part A is blended into the mixture to form @& refrig- erator bread dough that can be frozen until baking.
The microbeads prevent volatilization and oxidation of the butter flavor during storage.
Table IX
Ingredient amount (Parts)
Bread Flour 54
Shortening 5 ) Sugar 6
Salt 1 whole Milk Powder 2
Eggs 4
Water 32
Yeast 3
Cc) Baking of Refrigerator Bread Dough
The dough is thawed and allowed to rise to double its previous size. The bread is baked at 180°C. - The flavor is released upon baking when the fat coating on the microbeads melts.
Example XII
Chocolate Pudding Mix
A) Preparation of Chocolate-
Impregnated Microbeads
Microbeads prepared as described in Example 3° I part A are immersed in chocolate flavor and allowed to absorb the flavoring for 24 hours. The microbeads are coated as described in Example VIII with gelatin.
- ’ KE
B) Preparation of Pudding Mix
A pudding mix is prepared by adding the microbeads of part A to the ingredients in Table X below.
Table X
Ingredient % by Weight
Sugar 65.2%
Creaming agent CW-2 10.0% (Beatrice Co., Chicago, 1L)
Modified Tapioca Starch (T8-1801) 5.5% from National Starch Co, (New Jersey)
Pectin 6.0%
Cocoa Powder 8.0% - Microbeads 1.0% i. Salt 0.3%
Caramel Color 4.0%
The pudding mix can be made into a pudding by adding hot water (100°C) to the mix, stirring the mix for three minutes, and allow to cool, preferably in a refrigerator for at least a half hour. 25 .
Example XIII
Citrus Beverage Mix
A beverage base is prepared according to the proportions listed in Table XI by mixing the dry ingredients together.
Table XI
Ingredient Percent by Weight
Sugar 67.5
Dextrose 23.6
Citric Acid 7.5
27116 21s
Co - 27 -
Table XI Cont'd
Ingredient percent by Weight
Sodium Citrate 1.0
Ascorbic Acid 0.2
Microbeads 0.2
The microbeads are prepared as described in
Example I, part A, and impregnated with lemon and lime oils according to the procedure in Example I, part B, substituting a mixture of lemon and lime oils for peppermint oil. The microbeads are then coated with gelatin as described in Example VIII, and blended into the beverage base above. The beverage mix is reconstituted by mixing the mix (100 ¢) with water (24 oz.).
Example XIV:
Microwaveable Rum Cake
A) Preparation of Rum Extract Impregnated Microbeads
Microbeads prepared as described in Example
I, part A are mixed with an equal weight of rum extract
The excess extract is removed by filtration. The microbeads are coated with a fat that melts above 50 C.
B) preparation of Microwaveable Rum Cake Syrup
The microwaveable rum cake syrup is prepared by adding the microbeads of part A to the ingredients listed in Table XII below.
Table XII
Ingredient Percent By Weight
Microbeads 0.07
Sugar 59.93
Water 30.00
Glucose 10.00
_ 28 - 2 7 1 1 oO Syl
C) Baking of Cake
A rum cake is prepared in a conventional manner. The syrup of part A is poured over the cake.
The cake is placed in a microwave dish, and exposed to microwave radiation for three minutes. During exposure, the water in the rum extract in the microbeads will heat, and force rum flavor from the pores of the microbeads, and through the fat coating if the fat is not already melted.
Example XV
Dry Dog Food
A) Preparation of Meat Flavor
A roasted meat flavor is prepared by dissolving 2-methyl-3-furanthiol (200 mg.) and 2,5- dimethyl-3-furanthiol (200 mg) into ethanol. To this solution is added 2-methyl-3-ethyl pyrazine (50 mg) and 4,5-dimethyl thiazole. oo B) Preparation of Microbeads Impregnated With Meat
Flavor
Microbeads prepared as described in Example
I, part A are immersed in an equal weight of the flavoring solution of part A for 24 hours. The excess solution is removed by filtration. The microbeads are then coated by dry blending with an equal quantity of
HPMC and adding water to produce damp mix. The water is dried off and the mixture is ground.
C) Preparation of Dry Dog Food
The microbeads of part B are coated onto a dry dog food prepared in a conventional manner such as taught in U.S. Patent 3,380,832. The coating is done by dusting the microbeads onto the dry doy food immediately after the microbeads are suspended in warm fat, and the warm fat is sprayed onto the dry dog food.
- 2WIIS ~ : dol YO me 2711 0 JHC ~- 29 -
Example XVI
Peppermint Mints
Microbeads prepared as described in Example
I, parts A and B impregnated with peppermint oil are added to a sugar syrup (70% sucrose, 30% water by weight). The mixture is freeze dried and then ground.
Magnesium stearate (0.9% by weight) and talc (0.8% by weight) are added to the ground material, and the mixture is tabletted in a conventional manner to produce a tabletted mint candy. : Example XVII
Polymeric Beads Including Styrene-Butadiene Rubber
Styrene-butadiene rubber (10.0 g) is dissolved in toluene (90.0 g). In a separate beaker, polyvinylalcohol . (1.5 g) is dissolved in water (450.0 g) at about 40°C.
The copolymer solution is mixed with styrene monomer (150.0 g) and divinylbenzenc monomer (30.0 g). Benzoyl peroxide (1.5 g) is added to the mixture, and the mixture is agitated at room temperature. The mixture : with copolymer is added to the polyvinyl alcohol solution, and the combined mixture is agitated with a motor-driven propeller.
The mixture is heated to 80 - 90°C for at least four hours during which time it is agitated. The : mixture is cooled, and filtered to remove the beads.
CL The beads can be used in any of the foods in the previous examples. while several embodiments of the invention have been described, other embodiments will be apparent to those of ordinary skill in the art. Such embodi- ments are included within the scope of the present invention unless the following claims expressly state otherwise.

Claims (8)

  1. 2 7 1 1 6 Lille ) - - 30 - I CLAIM: . 1. A food product, comprising: a food product containing water—insoluble porous polymeric beads 10-100 microns in diameter, having microporous passages, wherein said beads are impregnated with a food flavoring containing volatile substances.
  2. © 2. The food product of claim 1 wherein said porous polymeric beads are coated with a water-soluble coating.
  3. 3. The food product of claim 1 wherein said porocug polymeric beads are coated with a coating that melts when heated.
  4. 4. The food product of ciaim 3 wherein said coating melts at a temperature greater than 30°C.
    20 . . . .
  5. 5. The food product of claim 4 wherein said coating melts at a temperature greater than 100°C.
  6. 6. The food product of claim 3 wherein said food matrix comprises a pudding mix.
    25 .
  7. 7. The food product of claim 3 wherein said food matrix comprises a baked good.
    3
  8. 8. The food product of claim 5 wherein said 0 food matrix comprises plural populations of said porous polymeric beads, each population adapted to release its flavoring at a different time.
    9. The food product of claim 1 wherein said porous polymeric beads are impregnated with an anti-oxidant. _ 30 —
    Co 27116 ne . . - 31 - +
    10. The food product of claim 3 wherein said coating comprises a fat.
    11. The food product of claim 1 wherein said - 5 food flavering is an oil that has been emulsified in water.
    12. A food product, comprising: : a liquid that has been concentrated by evaporative means; and a plurality of water—inscluble porous polymeric beads, 10-100 microns in diameter, having microporous passages said beads containing a food flavoring having volatile flavoring components, acid beads being dispersed throughout said liquid.
    15 .
    13. The food product of claim 12 wherein said liquid comprises a Syrup. :
    14. The food product of claim 13 wherein said syrup is maple syrup and said flavoring is a maple syrup flavoring component.
    15. The fool product of claim 14 wherein said syrup is a fruit syrup and said flavoring is a fruit flavoring component. .
    16. The food product of claim 12 wherein said liquid is a citrus juice, and said flavoring is a citrus flavoring.
    17. The food product of claim 12 wherein said liguid is a fruit juice, and said flavoring is a fruit flavoring.
    18. The food product of claim 12 wherein said beads are coated with a water-soluble ceating. — 31—-
    Cr 116 me
    19. A granular food product that dissolves in water to form a beverage, comprising: a substantially scluble beverage base and a plurality of water-inscluble porous polymeric beads, 10-100 microns in diameter, having microporous passages. wherein said beads are impregnated with a beverage flavoring having volatile substances.
    20. The granular food product of claim 19 wherein said beverage base comprises a sweetener and a fruit flavoring, and said beads contain a fruit flavoring.
    21. The granular food product of claim 19 wherein said heverage base comprises a coffee bean extract.
    22. The granular food product of claim 19 . wherein said beads contain a coffee flavor.
    23. The granular food product of claim 21 wherein said beads contain a cocoa flavor.
    24. The granular food product of claim 21 wherein said beads contain a chocolate flavor.
    25. The granular food product of claim 19 wherein said beverage base comprises a milk shake base.
    26. The granular food product of claim 25 wherein said beads contain a chocolate flavoring.
    27. The granular food product of claim 26 wherein said beads contain a fruit flavoring.
    28. The granular foor product of claim 19 wherein said beads are coated with a water-soluble coating component. 40 Steven E. Zibell Lindell C. Richey Michael J. Greenberg David Witkewitz Inventors
PH39967A 1989-02-06 1990-01-30 Food flavoring high-note enhancement by microbead delivery PH27116A (en)

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AU639645B2 (en) * 1989-10-10 1993-07-29 Wm. Wrigley Jr. Company Gradual release structures made from fiber spinning techniques
US5128155A (en) * 1990-12-20 1992-07-07 Wm. Wrigley Jr. Company Flavor releasing structures for chewing gum
DE4343670C2 (en) * 1993-12-21 2003-05-28 Becker & Co Naturinwerk Edible serving for food
US5413799A (en) * 1994-04-12 1995-05-09 Wm. Wrigley Jr. Company Method of making fruit-flavored chewing with prolonged flavor intensity
PH31445A (en) * 1994-04-12 1998-11-03 Wrigley W M Jun Co Fruit flavored chewing gum with prolonged flavor intensity.
US5429827A (en) * 1994-04-12 1995-07-04 Wm. Wrigley Jr. Company Method of making improved gum base for fruit-flavored chewing gum
BR9713619A (en) 1996-12-23 2000-04-11 Quest Int Particles containing organic polymer, process for producing them, and product and sunscreen product containing them
DE10336146B4 (en) * 2003-08-07 2007-06-28 Degussa Ag Process for the stable aromatization of beverages
US20060286200A1 (en) * 2005-04-18 2006-12-21 Castro Armando J Confections containing flavor delivery systems
SE0600887L (en) * 2006-04-24 2007-10-25 Lyckeby Culinar Ab Flavor release material and its use in various food products
US8353811B2 (en) * 2007-05-30 2013-01-15 Phillip Morris Usa Inc. Smoking articles enhanced to deliver additives incorporated within electroprocessed microcapsules and nanocapsules, and related methods
EP2659789B1 (en) * 2012-05-04 2019-05-01 Symrise AG Compound mixtures

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US3985298A (en) * 1973-05-23 1976-10-12 Moleculon Research Corporation Controlled release materials and method of use
US4576826A (en) * 1980-11-03 1986-03-18 Nestec S. A. Process for the preparation of flavorant capsules
US4384004A (en) * 1981-06-02 1983-05-17 Warner-Lambert Company Encapsulated APM and method of preparation
US4386106A (en) * 1981-12-01 1983-05-31 Borden, Inc. Process for preparing a time delayed release flavorant and an improved flavored chewing gum composition
US4497832A (en) * 1983-04-18 1985-02-05 Warner-Lambert Company Chewing gum composition having enhanced flavor-sweetness
US4804548A (en) * 1984-10-05 1989-02-14 Warner-Lambert Company Novel sweetener delivery systems
US4705691A (en) * 1985-11-18 1987-11-10 The Procter & Gamble Co. Beverage opacifier

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