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WO1985003414A1 - Encapsulation matrix composition and encapsulate containing same - Google Patents

Encapsulation matrix composition and encapsulate containing same Download PDF

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Publication number
WO1985003414A1
WO1985003414A1 PCT/US1985/000143 US8500143W WO8503414A1 WO 1985003414 A1 WO1985003414 A1 WO 1985003414A1 US 8500143 W US8500143 W US 8500143W WO 8503414 A1 WO8503414 A1 WO 8503414A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
matrix composition
composition
parts
encapsulating matrix
Prior art date
Application number
PCT/US1985/000143
Other languages
French (fr)
Inventor
Jannette M. Barnes
James A. Steinke
Original Assignee
Scm Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Scm Corporation filed Critical Scm Corporation
Publication of WO1985003414A1 publication Critical patent/WO1985003414A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C08L3/04—Starch derivatives, e.g. crosslinked derivatives
    • C08L3/06—Esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C08L3/02—Starch; Degradation products thereof, e.g. dextrin

Definitions

  • This invention relates to encapsulation, and more particularly a matrix composition for encapsulating an active ingredient at high loading levels.
  • the active ingredient may be an organoleptic material, an agricultural chemical, or a physiologically active material, e.g., a drug or insect control agent.
  • a principal object of the present invention is to provide an improved matrix composition adapted for extrusion and further having an improved capacity to contain in a stable manner a normally liquid dispersed phase, such as an organoleptic material, e.g., lemon oil, orange oil, or the like.
  • modified starches are used in the production of spray dried flavors, but they are not used commercially as an ingredient in extrusion encapsulation process formulations.
  • These encapsulation processes are basically different.
  • flavorant and emulsifier are added directly to the encapsulation matrix consisting of water, maltodextrin, gum arabic, etc. Water is then removed by spray drying.
  • the product is porous and not as stable as that produced by extrusion technology. In the latter case, water is removed before flavor is added and locked in as in U.S. Patent No. 3,704,137, supra. Extrusion products have superior shelf stability.
  • the maltodextrins useful herein have a low DE (dextrose equivalent), i.e., in the range of 3 to 40. Generally, they are made by first liquefying native starch with an acid or an enzyme to a DE less than about 15, followed by enzymatic conversion, e.g., with bacterial alpha-amylase (See U.S. Patent No. 3,849,194 and Reissue 30,880). As pointed out in U.S. Patent 3,974,033, maltodextrins are first prepared in syrup form and then spray dried to a moisture content of 3-5% by weight. These prior art maltodextrin materials and those prepared from oxidized starch as described in U.S. Patent No. 3,974,033 are useful herein.
  • the second principal ingredient of the improved matrix compositions hereof is a derivative of waxy maize identified as hydrogen octenylbutanedioate a ylodextrin. It has a Chemical Abstracts Registry Number 61932-62-5. This material is commercially available from National Starch and Chemical Corp. as "Capsul". "Capsul” has been used as an encapsulating agent in spray drying techniques. (See β€œModified Starch Encapsulating Agents Offer Superior Emulsification, Film Forming, and Low Surface Oil” by King et al. Food Product Development, Volume 10, No. 10, pages 54, 56, 57, December, 1976; and Sair et al U.S. Patent No.
  • emulsifier Another ingredient which is desirably, although not essentially present is an emulsifier.
  • This material is desirably edible, although where insecticides or maturation inhibitors are involved the emulsifying agent may be inedible by humans.
  • the emulsifiers are present in amounts from 0.25 to 5% by weight, and usually from 1% to 3%. Higher levels of emulsifier may be used, but appear not to be beneficial, and at the same time are not harmful.
  • emulsifying ' agents useful herein include diacetyl tartaric acid ester of a mono-diglyceride of C 8 -C, 8 fatty acids, e.g., palmitic stearic or olei ⁇ acids, ethoxylated mono-diglycerides, mono-diglyceride sodium sulfoacetate, monostearin sodium sulfoacetate, polymeric alkylaryl polyether alcohol, polyethylene glycol oleates or stearates, sodium lauryl sulfate, vegetable oils, glyceryl onooleate, glyceryl monostearate, sorbitan monostearate, acetylated monoglycerides, sodium stearoyl-2-lactylate, citrus stereoptene, lecithin, gum arabic, gum acacia, locust bean gum, guar gum, tragacanth gum, pectin, pectin albedo, a
  • sulfonate salts e.g., sodium lauryl sulfonate, sodium petroleum sulfonate, sodium napthalene sulfonate, etc.
  • the present invention is in an encapsulating matrix composition extrudable at a pressure in the range of from about 1 to about 10 atmospheres and having an improved loading capacity up to about 40% comprising a) from about 5 to about 95 parts by weight of maltodextrin and b) from about 95 to about 5 parts by weight of hydrogen octenylbutanedioate amylodextrin. Components a) and b) total 100 parts by weight.
  • the invention also contemplates a particulate composition comprising the foregoing matrix composition and from about 5% to about 40 weight percent of a normally liquid or volatile active ingredient, such as an organo ⁇ leptic material. Other ingredients may be present in the basic matrix composition.
  • modified starch primarily, utilization of its lipophilic characteristics to absorb the oil of the active ingredient into the matrix and hold it there.
  • the role of the maltodextrin is to provide matrix bulk, and at the same time an emulsion, prior to extrusion, of reasonable viscosity.
  • the relative pro ⁇ portions of these two components can vary within the above ranges, depending upon the loadings and extrusion pressures desired. Preferred proportions are about 80-60 parts maltodextrin and about 20-40 parts modified starch.
  • Weight percents as given herein are basis total composition unless otherwise specified.
  • the principal ingredients of the matrix compositions hereof are individually well known and commercially available as dry powders.
  • Another commercially available modified starch having a low DE is produced by American Maize Products Co. under the name "Amaizo ARD 2326".
  • This material is substantially equivalent to "Capsul" in the environment of this invention. It is described as an octenyl succinic anhydride derivative. Either of these components may be replaced in part with natural gums, e.g., gum acacia, gum arabic, gum tragacanth, etc., corn syrup solids having a DE below about 40, or sucrose. Up to 25% by weight of the component may be so replaced.
  • sucrose can be omitted or included as desired, and it is thus possible to produce "sugar-free” or sweetened compositions.
  • sucrose equivalent amounts of saccharin, cyclamate, aspartame, fructose, glucose, cellulose compounds, or polyhydric alcohols (e.g., sorbitol, mannitol) or the like, may be used.
  • the principal ingredients may also be mixed in such a way as to provide timed release and various batches of encapsulate blended to provide timed release over a period of time.
  • Modified starches, such as "Capsul" above described have several advantages over the current edible sucrose-maltodextrin systems.
  • Flavor systems con ⁇ taining high levels of water can be encapsulated in accordance with this invention. For example, orange juice concentrate containing 42% water can be encapsulated at 10-15% loading levels. With current sucrose systems, 5 to 6% loading and 20% water is about the limit. No other encapsulation system presently known to us is satisfactory for fruit essences. Highly volatile materials, such as dimethyl sulfide, can be encapsulated in the present systems at a 10% level. Current encapsulating systems enable only one half that amount of dimethyl sulfide.
  • the propylene glycol added to the matrix, via the flavor is about 32%. It may still be desirable to add a viscosity controlling amount, for instance about 5% of additional propylene glycol for viscosity control, the balance being emulsifiers or the like.
  • active ingredient means active agent plus carrier, for instance flavor plus water, or propylene glycol. Because of the nonhygroscopic nature of the present systems, the need for anticaking agents is alleviated.
  • one may employ many different volatile flavoring agents for example orange oil, lemon oil, grapefruit oil, lime oil, clove oil, peppermint oil, bay oil, cedarwood oil, ethanol fruit essence extracts such as apple essence, pear essence, pineapple essence, grape essence, peach essence, apricot essence, strawberry essence, raspberry essence, cherry essence, prune essence, plum essence, cinnamon oil,, oil of nutmeg, oil of sage, oil of bitter almonds, cassia oil, teaseed oil, coffee essence, and so forth. Mixtures of different flavoring agents may of course be employed.
  • Examples are the edible flavor and aroma bearing aldehydes, alcohols, esters, ketones, phenols, and lactones, for instance methyl anthranilate, decanal, nonanal, undecanal, cinnamic aldehyde, geraniol, menthol, methyl salicylate, phenylethyl alcohol, diacetyl, citronellol, citral, and so forth.
  • the proportion of flavoring agent to be in ⁇ corporated in the carrier base may be varied depending on the flavor strength desired in the final product.
  • the active agents in the encapsulants of the present invention may be organoleptics, e.g., flavors or fragrances, agricultural chemicals, e.g., insecticides, fertilizers, flavor enhancers, e.g., acetaldehyde or citral, growth hormones, maturation inhibitors, etc. , and pharmaceuticals, with or without carriers.
  • These encap ⁇ sulating matrices materials are soluble in water to release the active ingredient. They may be used as ingredients of candy or lozenges, or breath deodorants.
  • the active ingredients useful herein are desirably normally liquid and form a distinct dispersed phase in the hot matrix.
  • the method of preparing the encapsulates of the present invention is analogous to that in U.S. Patent No. 3,704,137 to Beck.
  • a tank having heating and agitating means, to effect the steps of mixing, cook- ing and cooling.
  • the matrix ingredients, water and other ingredients such as emulsifying agent and viscosity controlling agent, if desired, are charged into the tank, and the mass is stirred and subjected to heating or cooking, under a vacuum effective to remove water, until the boiling point of the mixture reaches, by way of example, about
  • the amount of water used initially is a solubilizing amount, sufficient to solubilize the matrix ingredients.
  • the amount is reduced to about 3-12%, for instance about 10%, depending in part upon proportions of ingredients and viscosity desired (for the susequent extrusion step) .
  • the vacuum selected for the boiling or cooking step is dependent in part on the active ingredient to be added. Cooking at 120Β°C. would prevent adding a highly volatile active ingredient to the cook solution. A typical vacuum may be about 685 m m Hg.
  • the com ⁇ position is in the form of an emulsion or slurry, depending upon whether the active ingredient is oil based or water based.
  • the cooking tank is provided with an extrusion cap or spinneret, isolated from the tank by a valve. Open- ing the valve allows the tank contents to move under pressure through the extrusion cap or spinneret into a basket carried in a shallow tray of. cold solvent for the active ingredient, such as isopropyl alcohol.
  • the extruder has a head pro ⁇ vided with a large number of about 1/64 inch diameter orifices through which the combined mix is forced under
  • the cold solvent serves two purposes, to remove excess active ingredient from the surface of the extrudate, and to effect solidification of the extruded melt (an example of a solvent temperature effective to solidify the extrudate is about -10Β°C).
  • the extruded rods can be subjected to agitation and comminution to wash off the excess oil, and also to break up the rods into desired lengths. From the tank, the broken-up rods are separated from a major portion of the liquid solvent by a settling or draining action, and the broken-up rods are then charged into a centrifuge to remove most of the liquid solvent, the solvent being dis ⁇ charged from the centrifuge into a solvent tank.
  • the particulate, rod-like solids from the centrifuge are discharged into a mixer, into which is also charged an anticaking agent.
  • the preferred anti ⁇ caking agent is siliceous material, preferably pyrogenic silica, of a particle size comparable to that desired in the final essential oil composition of my invention.
  • the anti-caking agent is incorporated into the melt mix prior to drying and screening, but the siliceous material can be added to the liquid solvent prior to extrusion or can be added to the rod-like particles after the centrifuging step.
  • the finished product contains an amount of essential oil up to about 40% of oil by weight of the finished product.
  • the product has good keeping properties in that it will not crystallize upon long standing, nor is it subject to substantial deterioration if suitably packaged and protected by antioxidants.
  • the use of about 0.5% by weight of the final composition of pyrogenic silica powder effectively prevents the rod-like particles of the com ⁇ position from sticking together upon long standing in a packaged condition and, also, of course, facilitates the transfer of the composition from the packages to the points of actual use of the composition.
  • This mixture was placed in a steel vessel fitted with a thermometer, a stirrer, an inlet tube and an exhaust and provided with heating and vacuum means.
  • the mass was charged into the vessel, stirred, a vacuum of 685 mm * created and the cook continued until the temperature reached 110Β°C. Water is continually removed.
  • the cook was terminated and at atmospheric pressure, 982 grams of orange oil was added. Mixing was carried on for 10 to 20 minutes at 110Β°C.
  • An extrusion cap or spinneret is fitted on the apparatus and isolated from the balance of the apparatus by a valve.
  • Opening the valve allows the contents to move through the spinneret and into a basket carried in a shallow tray of cold isopropyl alcohol.
  • Extrusion was done under nitrogen pressure of 20 to 100 psi over a period of 10 to 20 minutes and at a temperature of 105Β°C. to 110Β°C.
  • the rod-like extrudate was captured in a basket immersed in cold (-20 to 23Β°C.) alcohol and the resulting extruded rods broken with a suitable beater to provide particulate encapsulated orange oil.
  • Excess oil is removed from the exterior of the particles and can be recovered for recycling. The particles may be washed with more alcohol and centrifuged. The resultant granular powder is dried at a temperature not over about 38Β°C.
  • Example II The procedure of Example I is interrupted at the point just prior to introduction of the essential oil, and the encapsulation matrix material extruded per se. This material is useful as a powder diluent for encapsulated active agents in dry application in the case of agricultural chemicals. In this case no emulsifier is necessary. The ultimate water content is from 5 to 8% by weight.
  • EXAMPLE III The following ingredients in the amounts indicated were treated in the manner set forth in Example I, except where indicated. Maltodextrin 468 grams
  • EXAMPLE IV This example is like Example III except that 72 grams of propylene glycol are substituted for the orange juice. Extrusion was carried out at 105Β°C. to 110Β°C. at 20 psi of nitrogen. The resultant granular product carried a loading of propylene glycol of 10%. The viscosity control agent, propylene glycol, is useful in the extrusion step. When the material is dissolved in water in its ultimate use, the propylene glycol is released but is regarded as safe for human consumption.
  • the coke was carried out to 109Β°C. and 300 grams of dimethyl sulfide injected under pressure from a nitrogen pressurized vessel. After mixing, extrusion was carried out at 100Β°C. to 110 ⁇ C. at 50 psi nitrogen.
  • This example illustrates the encapsulation of a low boiling point (37Β°C.) material.
  • the loading was found to be 3.45% by weight.
  • the product is used by addition to water or an aqueous medium.
  • Lemon oil 125 grams The cook temperature is carried to 105Β°-110 ⁇ C. and extrusion carried out at the same temperature at 50 psi nitrogen. This yields a sugar sweetened encapsulate of lemon oil.

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Abstract

An extrudable encapsulation matrix composition having improved loading capacity for oils, flavors, fragrances, agricultural chemicals, insecticides, drugs, etc. The matrix comprises a maltodextrin and hydrogen octenylbutanedioate amylodextrin or equivalent.

Description

ENCAPSULATION MATRIX COMPOSITION AND ENCAPSULATE CONTAINING SAME
This invention relates to encapsulation, and more particularly a matrix composition for encapsulating an active ingredient at high loading levels. The active ingredient may be an organoleptic material, an agricultural chemical, or a physiologically active material, e.g., a drug or insect control agent.
BACKGROUND OF THE INVENTION A particular problem with prior art encapsulation matrices has been their inability to hold more than about 10% by weight of an encapsulate or dispersed phase, such as an essential oil. Accordingly, a principal object of the present invention is to provide an improved matrix composition adapted for extrusion and further having an improved capacity to contain in a stable manner a normally liquid dispersed phase, such as an organoleptic material, e.g., lemon oil, orange oil, or the like.
This improvement arose out of work orginally done by Beck as described in U.S. Patent No. 3,704,137 dated November 28, 1972. This patent describes certain relatively stable particulate essential oil-containing compositions and a process for making the solid particulate material. The procedural steps described by Beck can be used in preparing the novel encapsulates of the present invention. We have found that the load carrying capacity of the Beck material is below about 10% by weight. It has been found that increased loading capacity can be achieved by formulating a matrix composition to contain a) maltodextrin, a starch hydrolysate, and b) a modified starch which is a derivative of waxy maize. The com¬ position is characterized by high load capacity for an active ingredient, and handleability according to the Beck procedure, supra, at reasonable pressures and * temperatures. A similar procedure is disclosed in Swisher U.S. Patent No. 3,041,180.
Currently, modified starches are used in the production of spray dried flavors, but they are not used commercially as an ingredient in extrusion encapsulation process formulations. These encapsulation processes are basically different. In encapsulating by spray drying, flavorant and emulsifier are added directly to the encapsulation matrix consisting of water, maltodextrin, gum arabic, etc. Water is then removed by spray drying. The product is porous and not as stable as that produced by extrusion technology. In the latter case, water is removed before flavor is added and locked in as in U.S. Patent No. 3,704,137, supra. Extrusion products have superior shelf stability. However, until the present invention, active ingredient loadings available in extrusion were much lower (9-10%) than the 15 to 25% levels typical of spray dried products. According to the present invention, the advantages of extrusion encapsulation such as stability can be realized and loadings of up to 20-35 or 40% achieved. Still further, certain of the prior art encapsulation pro¬ cedures require substantial extrusion pressures and equip¬ ment capable of handling such pressures. These pressures are commonly above 1000 psi, e.g., 3000 to 4000 psi. The present invention allows extrusion to occur at pressures below 150 psig. and generally below 100 psig.
Various methods of producing altodextrins are known. Maltodextrins are identified by Chemical Abstracts Registry Number 9050-36-6. Reference may be had to
U.S. Patent No. 3,974,033 to Harjes et. al dated August 10, 197 and to the prior art discussed therein. The maltodextrins useful herein have a low DE (dextrose equivalent), i.e., in the range of 3 to 40. Generally, they are made by first liquefying native starch with an acid or an enzyme to a DE less than about 15, followed by enzymatic conversion, e.g., with bacterial alpha-amylase (See U.S. Patent No. 3,849,194 and Reissue 30,880). As pointed out in U.S. Patent 3,974,033, maltodextrins are first prepared in syrup form and then spray dried to a moisture content of 3-5% by weight. These prior art maltodextrin materials and those prepared from oxidized starch as described in U.S. Patent No. 3,974,033 are useful herein.
The second principal ingredient of the improved matrix compositions hereof is a derivative of waxy maize identified as hydrogen octenylbutanedioate a ylodextrin. It has a Chemical Abstracts Registry Number 61932-62-5. This material is commercially available from National Starch and Chemical Corp. as "Capsul". "Capsul" has been used as an encapsulating agent in spray drying techniques. (See "Modified Starch Encapsulating Agents Offer Superior Emulsification, Film Forming, and Low Surface Oil" by King et al. Food Product Development, Volume 10, No. 10, pages 54, 56, 57, December, 1976; and Sair et al U.S. Patent No. 4,232,047, particularly Example 9 in Column 14, describing extrusion of a mixture of "Capsul brand dextrin" and beef extract in a Brabender extruder) . In using these materials as extrusion encapsulating matrices, the emulsions become too viscous and extrusion pressures in the range of from 800 to 4000+ psi are required. The cost limitations imposed by equipment able to generate and withstand extrusion pressures for these materials is prohibitive. Again, as previously indicated, for this and other reasons, the modified starches are not used today commercially as an ingredient in extrusion encapsulation process formulations. According to the present invention, the maxiumum extrusion pressure is below 150 psi, and usually below 100 psi. The . two principal ingredients, when blended together with water and heated, preferably although not essentially under vacuum, to remove 85% or more of the water, form a com¬ position which is normally solid and is soluble in water at ordinary temperatures.
As indicated above, the combination of maltodextrin and "Capsul" enables high loading of active ingredients and extrusion at pressures below 150 psi. None of the prior art of which we are aware suggests or discloses this combination of starch derivatives as a matrix composition for extrusion encapsulating active ingredients.
Another ingredient which is desirably, although not essentially present is an emulsifier. This material is desirably edible, although where insecticides or maturation inhibitors are involved the emulsifying agent may be inedible by humans. In general, the emulsifiers are present in amounts from 0.25 to 5% by weight, and usually from 1% to 3%. Higher levels of emulsifier may be used, but appear not to be beneficial, and at the same time are not harmful. Specific examples of emulsifying' agents useful herein include diacetyl tartaric acid ester of a mono-diglyceride of C8-C,8 fatty acids, e.g., palmitic stearic or oleiσ acids, ethoxylated mono-diglycerides, mono-diglyceride sodium sulfoacetate, monostearin sodium sulfoacetate, polymeric alkylaryl polyether alcohol, polyethylene glycol oleates or stearates, sodium lauryl sulfate, vegetable oils, glyceryl onooleate, glyceryl monostearate, sorbitan monostearate, acetylated monoglycerides, sodium stearoyl-2-lactylate, citrus stereoptene, lecithin, gum arabic, gum acacia, locust bean gum, guar gum, tragacanth gum, pectin, pectin albedo, agar agar, algin, hydrogenated animal fat, etc. Also useful as emulsifiers are the sulfonate salts, e.g., sodium lauryl sulfonate, sodium petroleum sulfonate, sodium napthalene sulfonate, etc. BRIEF STATEMENT OF THE INVENTION
Briefly stated, therefore, the present invention is in an encapsulating matrix composition extrudable at a pressure in the range of from about 1 to about 10 atmospheres and having an improved loading capacity up to about 40% comprising a) from about 5 to about 95 parts by weight of maltodextrin and b) from about 95 to about 5 parts by weight of hydrogen octenylbutanedioate amylodextrin. Components a) and b) total 100 parts by weight. The invention also contemplates a particulate composition comprising the foregoing matrix composition and from about 5% to about 40 weight percent of a normally liquid or volatile active ingredient, such as an organo¬ leptic material. Other ingredients may be present in the basic matrix composition. These include water, emulsifiers, viscosity control agents, e.g., C2-C. alkylene glycols such as ethylene glycol, propylene glycol, butylene glycol, etc., -in effective quantities, generally below 10% by weight. The role of the modified starch is, primarily, utilization of its lipophilic characteristics to absorb the oil of the active ingredient into the matrix and hold it there. The role of the maltodextrin is to provide matrix bulk, and at the same time an emulsion, prior to extrusion, of reasonable viscosity. The relative pro¬ portions of these two components can vary within the above ranges, depending upon the loadings and extrusion pressures desired. Preferred proportions are about 80-60 parts maltodextrin and about 20-40 parts modified starch. DETAILED DESCRIPTION AND SPECIFIC EXAMPLES
Weight percents as given herein are basis total composition unless otherwise specified.
As indicated above, the principal ingredients of the matrix compositions hereof are individually well known and commercially available as dry powders. Another commercially available modified starch having a low DE is produced by American Maize Products Co. under the name "Amaizo ARD 2326". This material is substantially equivalent to "Capsul" in the environment of this invention. It is described as an octenyl succinic anhydride derivative. Either of these components may be replaced in part with natural gums, e.g., gum acacia, gum arabic, gum tragacanth, etc., corn syrup solids having a DE below about 40, or sucrose. Up to 25% by weight of the component may be so replaced. It should be noted, particularly with reference to edible compositions, that sucrose can be omitted or included as desired, and it is thus possible to produce "sugar-free" or sweetened compositions. Instead of sucrose, equivalent amounts of saccharin, cyclamate, aspartame, fructose, glucose, cellulose compounds, or polyhydric alcohols (e.g., sorbitol, mannitol) or the like, may be used. The principal ingredients may also be mixed in such a way as to provide timed release and various batches of encapsulate blended to provide timed release over a period of time. Modified starches, such as "Capsul" above described, have several advantages over the current edible sucrose-maltodextrin systems. Total replacement of the sucrose with "Capsul" or its equivalent results in a sugar- free product and enables use in consumer food products making that claim. Inversion of sucrose is a primary factor causing hygrosσopicity of the finished product. The presence of sucrose in the encapsulating system limits the length of the cook, the extrusion time and the cook temperature because of each of these parameters affects the degree of inversion. Finished products produced at higher temperatures and/or longer cook and extrusion times tend to be hygroscopic, sticky and unacceptable.
Replacement of part or all of the sucrose with Capsul or the like, reduces or eliminates sucrose inversion and attendant sensitivity to ambient moisture. Also larger batch sizes can be handled and processing times and temperatures made less critical. Flavor systems con¬ taining high levels of water (fruit essences) can be encapsulated in accordance with this invention. For example, orange juice concentrate containing 42% water can be encapsulated at 10-15% loading levels. With current sucrose systems, 5 to 6% loading and 20% water is about the limit. No other encapsulation system presently known to us is satisfactory for fruit essences. Highly volatile materials, such as dimethyl sulfide, can be encapsulated in the present systems at a 10% level. Current encapsulating systems enable only one half that amount of dimethyl sulfide.
Many flavor systems include high levels of propylene glycol. Such systems cannot be encapsulated successfully in current sucrose containing systems. Propylene glycol has the same adverse effect on sucrose containing systems as water; it makes the end product sticky and non-functional. However, with the systems of the present invention, loadings of propylene glycol of 15-20% by weight can be obtained. It should be noted that the addition of propylene glycol for viscosity control, up to 10% by weight, mentioned above, is in addition to the propylene glycol incidentally present in the flavor system. By way of example, the com¬ position of this invention may contain about 20% maltodextrin, about 30% Capsul, and about 40% flavor, of which 20% is oil and 80% is carrier (propylene glycol). Thus, the propylene glycol added to the matrix, via the flavor, is about 32%. It may still be desirable to add a viscosity controlling amount, for instance about 5% of additional propylene glycol for viscosity control, the balance being emulsifiers or the like.
Again, the present invention contemplates active ingredient loadings of from about 5 to about 40% by weight. For purposes of this application, the term "active ingredient" means active agent plus carrier, for instance flavor plus water, or propylene glycol. Because of the nonhygroscopic nature of the present systems, the need for anticaking agents is alleviated.
Regarding the active ingredients of the emulsion, one may employ many different volatile flavoring agents, for example orange oil, lemon oil, grapefruit oil, lime oil, clove oil, peppermint oil, bay oil, cedarwood oil, ethanol fruit essence extracts such as apple essence, pear essence, pineapple essence, grape essence, peach essence, apricot essence, strawberry essence, raspberry essence, cherry essence, prune essence, plum essence, cinnamon oil,, oil of nutmeg, oil of sage, oil of bitter almonds, cassia oil, teaseed oil, coffee essence, and so forth. Mixtures of different flavoring agents may of course be employed. In the case of fruit essences, such as those enumerated above, it is preferable to first purify them to remove water and low-molecular weight alcohols. It is also pre¬ ferred to add an edible oil and/or an edible emulsifying agent to the purified fruit essence so that it will emulsify properly with the matrix. Instead of or together with natural flavoring principles, synthetic flavoring agents may be employed. Examples are the edible flavor and aroma bearing aldehydes, alcohols, esters, ketones, phenols, and lactones, for instance methyl anthranilate, decanal, nonanal, undecanal, cinnamic aldehyde, geraniol, menthol, methyl salicylate, phenylethyl alcohol, diacetyl, citronellol, citral, and so forth.
The proportion of flavoring agent to be in¬ corporated in the carrier base may be varied depending on the flavor strength desired in the final product. As indicated above, the active agents in the encapsulants of the present invention may be organoleptics, e.g., flavors or fragrances, agricultural chemicals, e.g., insecticides, fertilizers, flavor enhancers, e.g., acetaldehyde or citral, growth hormones, maturation inhibitors, etc. , and pharmaceuticals, with or without carriers. These encap¬ sulating matrices materials are soluble in water to release the active ingredient. They may be used as ingredients of candy or lozenges, or breath deodorants. The active ingredients useful herein are desirably normally liquid and form a distinct dispersed phase in the hot matrix. The method of preparing the encapsulates of the present invention is analogous to that in U.S. Patent No. 3,704,137 to Beck.
In essence, a tank is provided, having heating and agitating means, to effect the steps of mixing, cook- ing and cooling. Initially, the matrix ingredients, water and other ingredients such as emulsifying agent and viscosity controlling agent, if desired, are charged into the tank, and the mass is stirred and subjected to heating or cooking, under a vacuum effective to remove water, until the boiling point of the mixture reaches, by way of example, about
104-116Β°C. At this point, the cook is terminated and the active ingredient is added, in the amount of about 5-40 weight percent. Mixing is carried out until complete, still at about the same elevated temperature, since no substantial cooling takes place.
In the above procedure, the amount of water used initially is a solubilizing amount, sufficient to solubilize the matrix ingredients. During the boiling, the amount is reduced to about 3-12%, for instance about 10%, depending in part upon proportions of ingredients and viscosity desired (for the susequent extrusion step) . The vacuum selected for the boiling or cooking step is dependent in part on the active ingredient to be added. Cooking at 120Β°C. would prevent adding a highly volatile active ingredient to the cook solution. A typical vacuum may be about 685 m m Hg.
Use of a higher vacuum permits boiling at a temperature even as low as about 70-80°C, permitting use of even more volatile active ingredients. Once the active ingredient is added the com¬ position is in the form of an emulsion or slurry, depending upon whether the active ingredient is oil based or water based.
The cooking tank is provided with an extrusion cap or spinneret, isolated from the tank by a valve. Open- ing the valve allows the tank contents to move under pressure through the extrusion cap or spinneret into a basket carried in a shallow tray of. cold solvent for the active ingredient, such as isopropyl alcohol. The extruder has a head pro¬ vided with a large number of about 1/64 inch diameter orifices through which the combined mix is forced under
20 to 150 psig air pressure. The cold solvent serves two purposes, to remove excess active ingredient from the surface of the extrudate, and to effect solidification of the extruded melt (an example of a solvent temperature effective to solidify the extrudate is about -10°C). In the tank, the extruded rods can be subjected to agitation and comminution to wash off the excess oil, and also to break up the rods into desired lengths. From the tank, the broken-up rods are separated from a major portion of the liquid solvent by a settling or draining action, and the broken-up rods are then charged into a centrifuge to remove most of the liquid solvent, the solvent being dis¬ charged from the centrifuge into a solvent tank.
The particulate, rod-like solids from the centrifuge are discharged into a mixer, into which is also charged an anticaking agent. The preferred anti¬ caking agent is siliceous material, preferably pyrogenic silica, of a particle size comparable to that desired in the final essential oil composition of my invention. The anti-caking agent is incorporated into the melt mix prior to drying and screening, but the siliceous material can be added to the liquid solvent prior to extrusion or can be added to the rod-like particles after the centrifuging step. The finished product contains an amount of essential oil up to about 40% of oil by weight of the finished product. The product has good keeping properties in that it will not crystallize upon long standing, nor is it subject to substantial deterioration if suitably packaged and protected by antioxidants. The use of about 0.5% by weight of the final composition of pyrogenic silica powder effectively prevents the rod-like particles of the com¬ position from sticking together upon long standing in a packaged condition and, also, of course, facilitates the transfer of the composition from the packages to the points of actual use of the composition.
The following examples are illustrative of the mode of making the compositions of this invention. All temperatures are in degrees Celsius and all percents are by weight unless otherwise stated. EXAMPLE I
The following ingredients in the amounts indicated were stirred together at room temperature to form a uniform liquid blend: This example represents the best mode of practicing our invention presently known to us. Maltodextrin 1940 grams
"Capsul" 485 grams
Polyglycerol esters of Cg-C10 fatty acids (emulsifying agent) 150 grams Water 1880 grams
This mixture was placed in a steel vessel fitted with a thermometer, a stirrer, an inlet tube and an exhaust and provided with heating and vacuum means. The mass was charged into the vessel, stirred, a vacuum of 685 mm* created and the cook continued until the temperature reached 110Β°C. Water is continually removed. The cook was terminated and at atmospheric pressure, 982 grams of orange oil was added. Mixing was carried on for 10 to 20 minutes at 110Β°C. An extrusion cap or spinneret is fitted on the apparatus and isolated from the balance of the apparatus by a valve.
Opening the valve allows the contents to move through the spinneret and into a basket carried in a shallow tray of cold isopropyl alcohol. Extrusion was done under nitrogen pressure of 20 to 100 psi over a period of 10 to 20 minutes and at a temperature of 105°C. to 110°C. The rod-like extrudate was captured in a basket immersed in cold (-20 to 23°C.) alcohol and the resulting extruded rods broken with a suitable beater to provide particulate encapsulated orange oil. Excess oil is removed from the exterior of the particles and can be recovered for recycling. The particles may be washed with more alcohol and centrifuged. The resultant granular powder is dried at a temperature not over about 38°C. for a period of 2 hours at a temperature sufficient to volatilize the isopropyl alcohol. An anti¬ caking agent, such as pyrogenic silica, calcium sulfate, mont orillonite clay, or the like, may be added in an amount of about l%-2%, if desired. The product is then screened to desired size and packaged. Further details of the process and apparatus will be found in U.S. Patent No. 3,704,137, supra. Alternative emulsifying agents that may be used instead of the polyglyceryl esters of fatty acids are exemplified in Swisher U.S. Patent No. 3,041,180. The loading level was 24.2% by weight. In use, the flavor can be released by disolving the particu¬ late product in water or an aqueous medium. This example illustrates the high loading capability of the matrices of the present invention.
EXAMPLE II The procedure of Example I is interrupted at the point just prior to introduction of the essential oil, and the encapsulation matrix material extruded per se. This material is useful as a powder diluent for encapsulated active agents in dry application in the case of agricultural chemicals. In this case no emulsifier is necessary. The ultimate water content is from 5 to 8% by weight. EXAMPLE III The following ingredients in the amounts indicated were treated in the manner set forth in Example I, except where indicated. Maltodextrin 468 grams
"Capsul" 117 grams
Emulsifier* 10 grams
Water 450 grams
Orange Juice 58Β°Conc. 115 grams Extrusion was carried out at 105Β°C. to 110Β°C. under 40 psi nitrogen.
This example illustrates the application of the invention to high moisture fruit flavors. The loading level was 15%. The juice is released on dissolution in water. *See Example I.
EXAMPLE IV This example is like Example III except that 72 grams of propylene glycol are substituted for the orange juice. Extrusion was carried out at 105Β°C. to 110Β°C. at 20 psi of nitrogen. The resultant granular product carried a loading of propylene glycol of 10%. The viscosity control agent, propylene glycol, is useful in the extrusion step. When the material is dissolved in water in its ultimate use, the propylene glycol is released but is regarded as safe for human consumption.
EXAMPLE V Following the procedure set forth in Example I, the following ingredients in the amounts indicated were blended, cooked and extruded. Maltodextrin 1940 grams
"Capsul" 485 grams
Emulsifier* 80 grams
Water 1880 grams
The coke was carried out to 109Β°C. and 300 grams of dimethyl sulfide injected under pressure from a nitrogen pressurized vessel. After mixing, extrusion was carried out at 100Β°C. to 110Ξ²C. at 50 psi nitrogen.
This example illustrates the encapsulation of a low boiling point (37Β°C.) material. The loading was found to be 3.45% by weight.
EXAMPLE VI Following the procedure of Example I, the follow¬ ing ingredients in the amounts indicated were blended, cooked and extruded. Maltodextrin M-100 2304 grams
Amaizo A R D 2326 121 grams Emulsifier* 80 grams
Water 1880 grams
Orange oil 440 grams Cooking was carried out to 105Β°C.-110Ξ²C.; extrusion was at 105Β°-110Β°C. at 20 psi nitrogen. The loading in this case was found to be 15.12% by weight. ♦Emulsifier of Example I
EXAMPLE VII Following the procedure of Example I, the follow¬ ing ingredients in the amounts indicated were blended, cooked and extruded.
Maltodextrin M-100 526 grams
Amaizo A R D 2326 58 grams Emulsifier* 34 grams
Water 450 grams
Lemon oil 175 grams
Cooking was carried out to 105Ξ²-110Β°C; extrusion was at 105Ξ²-110Β°C. at 20 psi nitrogen. The loading in this case was 12.4% by weight. ♦Emulsifier of Example I.
EXAMPLE VIII Following the procedure of Example I, the following ingredients in the amounts indicated were blended, cooked and extruded. Maltodextrin M-100 407 grams Staley Modified Starch 175 grams Emulsifier* 35 grams Water 450 grams Orange oil 125 grams
The cook temperature reached 105-110Β°C; extrusion was carried out at 105-110Β°C. at 20 psi nitrogen. The extrudate when washed and dried had an oil loading of 16% by weight. The product is used by addition to water or an aqueous medium.
♦Emulsifier of Example I.
EXAMPLE IX Following the procedure of Example I. The following ingredients in the amounts indicated are blended, cooked and extruded:
Maltodextrin 1940 grams "Capsul" 400 grams Sucrose 100 grams
Glyceryl monostearate 100 grams Water 1900 grams
Lemon oil 125 grams The cook temperature is carried to 105Β°-110Ξ²C. and extrusion carried out at the same temperature at 50 psi nitrogen. This yields a sugar sweetened encapsulate of lemon oil.

Claims

C L I M S
1. An encapsulating matrix composition extrudable at a pressure ranging from 1 to 10 atmospheres and having im¬ proved loading capacity comprising a) from about 5 to about 95 parts by weight of maltodextrin and b) from about 95 to about 5 parts by weight of hydrogen octenyl butanedioate amylodextrin, the combined weight of a) and b) being 100 parts by weight.
2. An encapsulating matrix composition as defined in claim 1, wherein component a) is present in the range of from about 80 to about 60 parts by weight and component b) is present in the range of about 20 to about 40 parts by weight.
3. An encapsulating matrix composition as defined in either of claims 1 and 2, wherein a part of component b) is replaced with a mono- or disaccharide.
4. An encapsulating matrix composition as defined in claim 3, wherein the disaccharide is sucrose..
5. An encapsulating matrix composition as defined in any one of the preceding claims, wherein the matrix composition also contains from about 0.25 to about 5 parts by weight of an emulsifier.
6. An encapsulating matrix composition as defined in claim 5, wherein the emulsifier is a mono-glyceride of stearic or oleic acid, a diglyceride or stearic or oleic acid, or a mixed mono-diglyceride of stearic or oleic acid or a polyglycerol ester of a Cg to C,g fatty acid.
7. An encapsulating matrix composition as defined in any one of the preceding claims in slurry form including a viscosity controlling amount of an alkylene glycol.
8. An encapsulating matrix composition as defined in claim 7, wherein said alkylene glycol is a C, to C. glycol.
9. An encapsulating matrix composition as defined in claim 8, wherein the glycol is propylene glycol.
10. A particulate composition comprising 1) an encapsulating matrix composition as claimed in any one of the preceding claims, and 2) up to about 40% by weight of an active ingredient.
11. A composition as defined in claim 10, wherein the active ingredient is a fruit essence or an essential oil composition.
12. A method of preparing a stable, particulate essential oil composition, comprising the steps of
1) agitating and boiling a mixture of a) from about 5 to about 95 parts by weight of maltodextrin; b) from about 95 to about 5 parts by weight of hydrogen octenylbutanedioate amylodextrin; c) the combined weights of a) and b) being 100 parts by weight; and d) water; to form an encapsulating matrix composition.
2) mixing an active ingredient with said matrix composition to form a slurry or emulsion composition;
3) extruding said slurry or emulsion composition into a cold solvent for the active ingredient to form an extrudate, the solvent being at a temperature effective to solidify the extrudate; and
4) comminuting the extrudate;
5) the extrusion being carried out at a pressure in the range of about 1-10 atmospheres.
13. The method of claim 12, wherein said slurry com¬ position comprises up to about 40 percent by weight active ingredient.
14. The method of claim 13, wherein said active in¬ gredient is an essential oil composition or a fruit essence.
15. The method of claim 14, wherein said essential oil composition comprises essential oil plus carrier.
16. The method of claim 15, wherein said carrier is propylene glycol.
17. The method of any one of claims 14 to 16, wherein said matrix composition comprises about 80 to about 60 parts by weight of a) and about 20 to about 40 parts by weight of b) .
18. The method of any one of claims 12 to 17, wherein said matrix composition further comprises a) a viscosity controlling amount of an alkylene glycol, or b) an emulsifying amount of an emulsifier; or c) a carbohydrate in a flavoring or bulking amount; or d) a natural gum in a bulking amount; or e) combinations of a) , b) , c) and d) .
19.- The method of claim 18, wherein said carbohydrate is a mono- or disaccharide.
20. The method of claim 18, wherein said emulsifier is a) a monoglyceride of stearic or oleic acid; or b) a mono- diglyceride of stearic or oleic acid; or c) a polyglycerol ester of a Cg to C.8 fatty acid.
PCT/US1985/000143 1984-01-31 1985-01-25 Encapsulation matrix composition and encapsulate containing same WO1985003414A1 (en)

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EP0379147A3 (en) * 1989-01-17 1991-04-03 Sterling Winthrop Inc. Extrudable elastic gel for use as carrier for therapeutic agent
US5108762A (en) * 1989-04-19 1992-04-28 Wm. Wrigley Jr. Company Gradual release structures for chewing gum
US5128155A (en) * 1990-12-20 1992-07-07 Wm. Wrigley Jr. Company Flavor releasing structures for chewing gum
US5154939A (en) * 1989-04-19 1992-10-13 Wm. Wrigley Jr. Company Use of salt to improve extrusion encapsulation of chewing gum ingredients
US5165944A (en) * 1989-04-19 1992-11-24 Wm. Wrigley Jr. Company Gradual release structures for chewing gum
US5198251A (en) * 1989-04-19 1993-03-30 Wm. Wrigley Jr. Company Gradual release structures for chewing gum
EP0540460A1 (en) * 1991-10-25 1993-05-05 Fuisz Technologies Ltd. Novel saccharide-based matrix
EP0550067A1 (en) * 1991-12-30 1993-07-07 Hercules Incorporated High load spray dry encapsulation
US5229148A (en) * 1989-04-19 1993-07-20 Wm. Wrigley Jr. Company Method of combining active ingredients with polyvinyl acetates
WO1994001092A1 (en) * 1992-07-03 1994-01-20 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Composition for controlled release of an active substance and method for the preparation of such a composition
EP0599535A1 (en) * 1992-11-24 1994-06-01 Cerestar Holding Bv Starch based material
EP0601964A2 (en) * 1992-10-20 1994-06-15 Fuisz Technologies Ltd. A controlled melting point matrix formed with admixtures of a shearform matrix material and an oleaginous material
EP0601965A2 (en) * 1992-10-23 1994-06-15 Fuisz Technologies Ltd. Process for making shearform matrix
EP0621752A1 (en) * 1992-09-22 1994-11-02 McCORMICK & COMPANY, INCORPORATED Flavor encapsulation
US5364627A (en) * 1989-10-10 1994-11-15 Wm. Wrigley Jr. Company Gradual release structures made from fiber spinning techniques
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WO2002000039A3 (en) * 2000-06-27 2002-04-25 Nestle Sa Flavour composition
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WO2004049827A1 (en) * 2002-12-02 2004-06-17 Takasago International Corporation Granulated flavor and method for producing the same
WO2006127293A2 (en) * 2005-05-23 2006-11-30 Cadbury Adams Usa Llc Enhanced flavor-release comestible compositions and methods for same
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US7727565B2 (en) 2004-08-25 2010-06-01 Cadbury Adams Usa Llc Liquid-filled chewing gum composition
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EP0379147A3 (en) * 1989-01-17 1991-04-03 Sterling Winthrop Inc. Extrudable elastic gel for use as carrier for therapeutic agent
US5229148A (en) * 1989-04-19 1993-07-20 Wm. Wrigley Jr. Company Method of combining active ingredients with polyvinyl acetates
US5154939A (en) * 1989-04-19 1992-10-13 Wm. Wrigley Jr. Company Use of salt to improve extrusion encapsulation of chewing gum ingredients
US5165944A (en) * 1989-04-19 1992-11-24 Wm. Wrigley Jr. Company Gradual release structures for chewing gum
US5198251A (en) * 1989-04-19 1993-03-30 Wm. Wrigley Jr. Company Gradual release structures for chewing gum
US5108762A (en) * 1989-04-19 1992-04-28 Wm. Wrigley Jr. Company Gradual release structures for chewing gum
US5364627A (en) * 1989-10-10 1994-11-15 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
EP0540460A1 (en) * 1991-10-25 1993-05-05 Fuisz Technologies Ltd. Novel saccharide-based matrix
US5811123A (en) * 1991-12-17 1998-09-22 Fuisz Technologies Ltd. Method of treating mucosal tissue
EP0550067A1 (en) * 1991-12-30 1993-07-07 Hercules Incorporated High load spray dry encapsulation
US5427804A (en) * 1992-03-05 1995-06-27 Fuisz Technologies Ltd. Low-fat edible proteins with maltodextrins and low-saturate oils
WO1994001092A1 (en) * 1992-07-03 1994-01-20 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Composition for controlled release of an active substance and method for the preparation of such a composition
US5585114A (en) * 1992-07-03 1996-12-17 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Composition for controlled release of an active substance and method for the preparation of such a composition
EP0621752A1 (en) * 1992-09-22 1994-11-02 McCORMICK & COMPANY, INCORPORATED Flavor encapsulation
EP0621752A4 (en) * 1992-09-22 1995-08-23 Mccormick & Co Inc Flavor encapsulation.
US5601865A (en) * 1992-09-22 1997-02-11 Mccormick & Company, Inc. Flavor encapsulation
EP0601964A3 (en) * 1992-10-20 1994-08-17 Fuisz Technologies Ltd A controlled melting point matrix formed by admixtures of a shear formed matrix material with an oleaginous material.
EP0601964A2 (en) * 1992-10-20 1994-06-15 Fuisz Technologies Ltd. A controlled melting point matrix formed with admixtures of a shearform matrix material and an oleaginous material
EP0601965A3 (en) * 1992-10-23 1994-08-31 Fuisz Technologies Ltd
EP0601965A2 (en) * 1992-10-23 1994-06-15 Fuisz Technologies Ltd. Process for making shearform matrix
EP0599535A1 (en) * 1992-11-24 1994-06-01 Cerestar Holding Bv Starch based material
US6652895B2 (en) 1993-04-16 2003-11-25 Mccormick & Company, Inc. Encapsulation compositions
US6187351B1 (en) 1993-04-16 2001-02-13 Mccormick & Company, Inc. Encapsulation compositions
US6139872A (en) * 1996-08-14 2000-10-31 Henkel Corporation Method of producing a vitamin product
US7588793B1 (en) 1998-06-05 2009-09-15 Cadbury Adams Usa, Llc Enhanced flavoring compositions containing N-ethyl-p-menthane-3-carboxamide and method of making and using same
WO2002000039A3 (en) * 2000-06-27 2002-04-25 Nestle Sa Flavour composition
WO2002065858A1 (en) * 2001-02-16 2002-08-29 Firmenich Sa Encapsulated flavor and/or fragrance composition
US6932982B2 (en) 2001-02-16 2005-08-23 Firmenich Sa Encapsulated flavor and/or fragrance composition
WO2003056938A1 (en) * 2002-01-10 2003-07-17 Firmenich Sa Process for the preparation of extruded delivery systems
US8017060B2 (en) 2002-01-10 2011-09-13 Firmenich Sa Process for the preparation of extruded delivery systems
WO2004049827A1 (en) * 2002-12-02 2004-06-17 Takasago International Corporation Granulated flavor and method for producing the same
US9271904B2 (en) 2003-11-21 2016-03-01 Intercontinental Great Brands Llc Controlled release oral delivery systems
US8097271B2 (en) 2004-08-11 2012-01-17 Kraft Foods Global Brands Llc Warming compositions and delivery systems therefor
US8101208B2 (en) 2004-08-11 2012-01-24 Kraft Foods Global Brands Llc Sensate compositions and delivery systems therefor
US7727565B2 (en) 2004-08-25 2010-06-01 Cadbury Adams Usa Llc Liquid-filled chewing gum composition
US9198448B2 (en) 2005-02-07 2015-12-01 Intercontinental Great Brands Llc Stable tooth whitening gum with reactive ingredients
WO2006127293A2 (en) * 2005-05-23 2006-11-30 Cadbury Adams Usa Llc Enhanced flavor-release comestible compositions and methods for same
WO2006127293A3 (en) * 2005-05-23 2007-03-01 Cadbury Adams Usa Llc Enhanced flavor-release comestible compositions and methods for same
KR101411072B1 (en) * 2005-07-20 2014-06-27 λ””μ—μŠ€μ—  아이피 μ–΄μ…‹μΈ  λΉ„.브이. Novel stabilized carotenoid compositions
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WO2017203006A1 (en) * 2016-05-27 2017-11-30 Firmenich Sa High load flavor particles
CN109195456A (en) * 2016-05-27 2019-01-11 εΌ—ι—¨ε°Όθˆζœ‰ι™ε…¬εΈ High useful load seasoning particle
CN109195456B (en) * 2016-05-27 2022-10-11 εΌ—ι—¨ε°Όθˆζœ‰ι™ε…¬εΈ High load seasoning particles

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JPS61501078A (en) 1986-05-29
EP0169893A4 (en) 1987-01-22
EP0169893A1 (en) 1986-02-05

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