WO1985003414A1 - Encapsulation matrix composition and encapsulate containing same - Google Patents
Encapsulation matrix composition and encapsulate containing same Download PDFInfo
- 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
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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 “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.
- 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 120°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 -10°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 110°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 110°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.
- 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 105°C. to 110°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 109°C. and 300 grams of dimethyl sulfide injected under pressure from a nitrogen pressurized vessel. After mixing, extrusion was carried out at 100°C. to 110 ⁇ C. at 50 psi nitrogen.
- This example illustrates the encapsulation of a low boiling point (37°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 105°-110 ⁇ C. and extrusion carried out at the same temperature at 50 psi nitrogen. This yields a sugar sweetened encapsulate of lemon oil.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US57565484A | 1984-01-31 | 1984-01-31 | |
US575,654 | 1984-01-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1985003414A1 true WO1985003414A1 (en) | 1985-08-15 |
Family
ID=24301184
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1985/000143 WO1985003414A1 (en) | 1984-01-31 | 1985-01-25 | Encapsulation matrix composition and encapsulate containing same |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0169893A4 (de) |
JP (1) | JPS61501078A (de) |
WO (1) | WO1985003414A1 (de) |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0252374A1 (de) * | 1986-06-25 | 1988-01-13 | Nabisco Brands, Inc. | Eingekapselte aktive Ingredienzien, Verfahren zu deren Herstellung und ihre Anwendung in eingenommenen Produkten |
EP0379147A3 (de) * | 1989-01-17 | 1991-04-03 | Sterling Winthrop Inc. | Extrudierbares elastisches Gel zur Verwendung als Träger für Arzneistoffe |
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 (de) * | 1991-10-25 | 1993-05-05 | Fuisz Technologies Ltd. | Neue Matrix auf Saccharid-Basis |
EP0550067A1 (de) * | 1991-12-30 | 1993-07-07 | Hercules Incorporated | Verkapselung einer hohen Ladung durch Sprühtrocknung |
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 (de) * | 1992-11-24 | 1994-06-01 | Cerestar Holding Bv | Material basiert auf Stärke |
EP0601965A2 (de) * | 1992-10-23 | 1994-06-15 | Fuisz Technologies Ltd. | Verfahren zur Herstellung eines "Shearform" Matrix |
EP0601964A2 (de) * | 1992-10-20 | 1994-06-15 | Fuisz Technologies Ltd. | Grundmasse mit kontrolliertem Schmelzpunkt die durch Vermischen eines "shearform" Matrix mit einem öligen Material gebildet wird |
EP0621752A1 (de) * | 1992-09-22 | 1994-11-02 | McCORMICK & COMPANY, INCORPORATED | Geschmackstoffverkapselung |
US5364627A (en) * | 1989-10-10 | 1994-11-15 | Wm. Wrigley Jr. Company | Gradual release structures made from fiber spinning techniques |
US5427804A (en) * | 1992-03-05 | 1995-06-27 | Fuisz Technologies Ltd. | Low-fat edible proteins with maltodextrins and low-saturate oils |
US5601865A (en) * | 1992-09-22 | 1997-02-11 | Mccormick & Company, Inc. | Flavor encapsulation |
US5811123A (en) * | 1991-12-17 | 1998-09-22 | Fuisz Technologies Ltd. | Method of treating mucosal tissue |
US6139872A (en) * | 1996-08-14 | 2000-10-31 | Henkel Corporation | Method of producing a vitamin product |
US6187351B1 (en) | 1993-04-16 | 2001-02-13 | Mccormick & Company, Inc. | Encapsulation compositions |
WO2002000039A3 (en) * | 2000-06-27 | 2002-04-25 | Nestle Sa | PERFUME COMPOSITION |
WO2002065858A1 (en) * | 2001-02-16 | 2002-08-29 | 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 |
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 |
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 |
US7727565B2 (en) | 2004-08-25 | 2010-06-01 | Cadbury Adams Usa Llc | Liquid-filled chewing gum composition |
US8097271B2 (en) | 2004-08-11 | 2012-01-17 | Kraft Foods Global Brands Llc | Warming compositions and delivery systems therefor |
KR101411072B1 (ko) * | 2005-07-20 | 2014-06-27 | 디에스엠 아이피 어셋츠 비.브이. | 신규의 안정화된 카로티노이드 조성물 |
US8846007B2 (en) | 2005-12-23 | 2014-09-30 | Intercontinental Great Brands Llc | Compositions providing a heating sensation for oral or dermal delivery |
US9198448B2 (en) | 2005-02-07 | 2015-12-01 | Intercontinental Great Brands Llc | Stable tooth whitening gum with reactive ingredients |
US9271904B2 (en) | 2003-11-21 | 2016-03-01 | Intercontinental Great Brands Llc | Controlled release oral delivery systems |
WO2017203006A1 (en) * | 2016-05-27 | 2017-11-30 | Firmenich Sa | High load flavor particles |
Families Citing this family (1)
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WO2005029967A1 (en) * | 2003-09-26 | 2005-04-07 | National Starch And Chemical Investment Holding Corporation | Bulking agents for baked goods |
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1985
- 1985-01-25 EP EP19850900925 patent/EP0169893A4/de not_active Withdrawn
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- 1985-01-25 JP JP60500577A patent/JPS61501078A/ja active Pending
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Cited By (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0252374A1 (de) * | 1986-06-25 | 1988-01-13 | Nabisco Brands, Inc. | Eingekapselte aktive Ingredienzien, Verfahren zu deren Herstellung und ihre Anwendung in eingenommenen Produkten |
EP0379147A3 (de) * | 1989-01-17 | 1991-04-03 | Sterling Winthrop Inc. | Extrudierbares elastisches Gel zur Verwendung als Träger für Arzneistoffe |
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 (de) * | 1991-10-25 | 1993-05-05 | Fuisz Technologies Ltd. | Neue Matrix auf Saccharid-Basis |
US5811123A (en) * | 1991-12-17 | 1998-09-22 | Fuisz Technologies Ltd. | Method of treating mucosal tissue |
EP0550067A1 (de) * | 1991-12-30 | 1993-07-07 | Hercules Incorporated | Verkapselung einer hohen Ladung durch Sprühtrocknung |
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 |
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EP0621752A1 (de) * | 1992-09-22 | 1994-11-02 | McCORMICK & COMPANY, INCORPORATED | Geschmackstoffverkapselung |
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Also Published As
Publication number | Publication date |
---|---|
JPS61501078A (ja) | 1986-05-29 |
EP0169893A4 (de) | 1987-01-22 |
EP0169893A1 (de) | 1986-02-05 |
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