WO1990013994A2 - Controlled release of dihydrochalcones in chewing gum - Google Patents

Controlled release of dihydrochalcones in chewing gum Download PDF

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Publication number
WO1990013994A2
WO1990013994A2 PCT/US1990/004005 US9004005W WO9013994A2 WO 1990013994 A2 WO1990013994 A2 WO 1990013994A2 US 9004005 W US9004005 W US 9004005W WO 9013994 A2 WO9013994 A2 WO 9013994A2
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WO
WIPO (PCT)
Prior art keywords
sweetener
neodhc
dihydrochalcone
chewing gum
gum
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Application number
PCT/US1990/004005
Other languages
French (fr)
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WO1990013994A3 (en
Inventor
Robert J. Yatka
Original Assignee
Wm. Wrigley Jr. Company
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.)
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Publication date
Application filed by Wm. Wrigley Jr. Company filed Critical Wm. Wrigley Jr. Company
Priority to PCT/US1990/004005 priority Critical patent/WO1990013994A2/en
Publication of WO1990013994A2 publication Critical patent/WO1990013994A2/en
Publication of WO1990013994A3 publication Critical patent/WO1990013994A3/en

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Classifications

    • 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
    • A23G4/10Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • 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
    • A23G4/08Chewing gum characterised by the composition containing organic or inorganic compounds of the chewing gum base
    • 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

Definitions

  • the present invention relates to methods for producing chewing gum. More particularly the invention relates to producing chewing gum containing high- potency sweeteners which have been treated to control their release and enhance shelf-life stability.
  • One such high potency sweetener is dihydrochalcone.
  • This sweetener which is not approved for use in food products or in chewing gum, is being considered by many European countries as a food additive.
  • This high potency sweetener gives chewing gum a mild, fast sweetness release and a long, mild lingering sweetness and after taste. This type of sweetness does not balance with the various types of chewing gum flavors. Methods of treating the high potency sweetener to increase the sweetness release initially and control the release of sweetness in balance with the chewing gum flavor would therefore be a definite improvement.
  • U.S. Patent No. 3,653,923 discloses a composition of dihydrochalcone and a saccharin sweetener.
  • U.S. Patent No. 4,158,068 discloses a sweetener mixture of acesulfame and other sweeteners including dihydrochalcones.
  • U.S. Patent No. 4,254,155 discloses a process for preparing a dihydrochalcone-base sweetening composition containing neohesperidin dihydrochalcones, a taste modifier, and having an acidic pH.
  • U.S. Patent No. 4,085,232 discloses a sweetening composition comprising a dihydrochalcone, a sugar, cream of tarter and a vanilla flavor.
  • U.S. Patent No. 4,803,082 discloses a powdered flavor composition encapsulated in a matrix of thaumatin, dihydrochalcones, and a wax or fat. Other patents disclose how a sweetener like aspartame can be physically modified to control its release rate in chewing gum.
  • U.S. Patent No. 4,597,970 to Sharma et al. teaches a process for producing an agglomerated sweetener wherein the sweetener is dispersed in a hydrophobic matrix consisting essenti ⁇ ally of lecithin, a glyceride, and a fatty acid or wax having a melting point between 25°C and 100°C.
  • the method disclosed uses a spray-congealing step to form the sweetener-containing matrix into droplets, followed by a fluid-bed second coating on the agglomerated par ⁇ ticles.
  • U.S. Patent No. 4,230,687 to Sair et al. teaches a process for encasing an active ingredient to achieve gradual release of the ingredient in a product such as chewing gum.
  • the method described involves adding the ingredient to an encapsulating material in the form of a viscous paste. High-shear mixing is used to achieve a homogeneous dispersion of the ingredient within the matrix, which is subsequently dried and ground.
  • U.S. Patent No. 4,139,639 to Bahoshy et al. teaches a process of "fixing" aspartame by co-drying (by spray drying or fluid-bed coating) a solution con ⁇ taining aspartame and an encapsulating agent, such as gum arabic, to thereby surround and protect the aspar ⁇ tame in the gum during storage.
  • U.S. Patent No. 4,384,004 to Cea et al. teaches a method of encapsulating aspartame with vari ⁇ ous solutions of encapsulating agents using various encapsulation techniques, such as spray drying, in order to increase the shelf-stability of the aspartame.
  • U.S. Patent No. 4,634,593 to Stroz et al. teaches a method for producing controlled release sweeteners for confections, such as chewing gum.
  • the method taught therein involves the use of an insoluble fat material which is mix mulled with the sweetener.
  • the present invention includes a method for producing chewing gum ⁇ with a modified high-potency sweetener, specifically dihydrochalcones (DHC) , as well as the chewing gum so produced.
  • the controlled- release, high-potency sweetener is obtained by modifying the sweetener by encapsulation, partial encapsulation or partial coating, entrapment or absorption with water-soluble materials or water- insoluble materials.
  • the procedures for modifying the sweetener include spray drying, spray chilling, fluid- bed coating, coacervation, and other agglomerating and standard encapsulating techniques.
  • the sweetener may also be absorbed onto an inert or water-insoluble material.
  • the sweetener may be modified in a multiple step process comprising any of the processes or combination of processes noted.
  • the sweetener, DHC may also be combined with other sweeteners including, but not limited to, sucrose, dextrose, fructose, maltose, maltodextrin, xylose, palatinose, or others that are considered bulk sweeteners, as well as sugar alcohols including but not limited to sorbitol, mannitol, xylitol, maltitol, lactitol, palatinit, and lycasin.
  • the high-potency sweetener DHC may also be combined with other high-potency sweeteners including. but not limited to, thaumatin, aspartame, acesulfame K, sodium saccharin, sucralose, alitame, cyclamate, stevioside and glycyrrhizin.
  • This sweetener when modified according to the present invention, gives a chewing gum having a controlled-release sweetener.
  • a higher quantity of sweetener can be used having a controlled sweetness release that is compatible with the flavor release in chewing gum, giving a highly consumer-acceptable chewing gum product.
  • DHC dihydrochalcone
  • concentrations usually used DHC has a mild sweet taste that does linger, and has a lingering aftertaste, with a slight licorice, menthol aftertaste.
  • DHC Dihydrochalcone
  • NeoDHC Neohesperidin Dihydrochalcone
  • NDHC Naringin Dihydrochalcone
  • HDHCG Hesperetin Dihydrochalcone 4'- ⁇ -D-glucoside
  • Other DHC compounds may be sweeteners, but virtually all toxicology studies have been done on these three DHC sweeteners. Only NeoDHC is currently commercially available and approved for food use in a few countries.
  • the sweetener When DHC is added to chewing gum at a level of about 0.001% to 0.1%, the sweetener gives chewing gum a mild sweetness that leaves a menthol/licorice flavor character. It would be considered a significant improvement to a chewing gum to have the DHC sweetener release its sweetness more slowly as the flavor in the gum is released, thus balancing the overall taste perception. This would also slow the release of the menthol/licorice aftertaste, so that more sweetener could be used without a significant aftertaste. Physical modifications of this sweetener would also improve its stability in the final product.
  • Dihydrochalcone can be added as a powder, as an aqueous solution, or dissolved in glycerine, propylene glycol, corn syrup, hydrogenated starch hydrolyzate, or any other compatible aqueous solutions.
  • an emulsifier can also be mixed in the solution with the DHC sweetener and the mixture added to a chewing gum.
  • a flavor can also be added to the sweetener/emulsifier mixture.
  • the emulsion formed can be added to chewing gum.
  • Powdered DHC may also be mixed into a molten chewing gum base during base manufacture or prior to manufacture of the gum. DHC may also be mixed with base ingredients during base manufacture.
  • DHC usage levels of DHC in water or aqueous solvent is limited to its solubility in the aqueous solvent.
  • solubility in water at 25°C is 3.5 grams per liter and increases with temperature, to 650 grams per liter at 80°C.
  • the solubility of NeoDHC is less than in plain water.
  • NeoDHC is also soluble in ethanol and methanol.
  • the amount of DHC added to chewing gum of the present invention is about 0.001% to 0.1%.
  • the range of DHC in gum is about 0.004% to 0.04%, or 40 to 400 ppm.
  • DHC releases slowly from chewing gum during the early stages of mastication of the gum because of its low solubility in water.
  • Physical modifications of the sweetener by encapsulation with another substrate will increase its release in chewing gum by increasing the solubility or dissolution rate of DHC. Also, some modifications may make the DHC solubility even lower so that its release rate in chewing gum would be even more delayed.
  • Any standard technique which gives partial or full encapsulation of the DHC sweetener can be used. These techniques include, but are not limited to, spray drying, spray chilling, fluid-bed coating and coacervation. These encapsulation techniques that give partial encapsulation or full encapsulation can be used individually or in any combination in a single step process or multiple step process.
  • more delayed release of sweetener is obtained in multistep processes like spray drying the sweetener and then fluid-bed coating of the resultant powder.
  • a fast release sweetener is obtained by a single step like spray drying the sweetener with water soluble materials.
  • the encapsulation techniques here described are standard coating techniques and generally give varying degrees of coating, from partial to full coat ⁇ ing, depending on the coating composition used in the process.
  • the coating compositions may be suscep ⁇ tible to water permeation to various degrees.
  • compositions that have high organic solubility, good film-forming properties and low water solubility give better delayed release of the sweetener.
  • Such compositions include acrylic polymers and copolymers, carboxyvinyl polymer, polyamides, polystyrene, polyr vinyl acetate, polyvinyl acetate phthalate, polyvinyl- pyrrolidone, and waxes.
  • DHC sweetener Although all of these materials are possible for encapsulation of DHC sweetener, only food-grade materials should be con ⁇ sidered.
  • Two standard food-grade coating materials that are good film formers but not water soluble are shellac and Zein. Others which are more water soluble. but good film formers, are materials like agar, algi- nates, a wide range of cellulose derivatives like ethyl cellulose, methyl cellulose, sodium hydroxymethyl cellulose, and hydroxypropylmethyl cellulose, dextrin, gelatin, and modified starches. These ingredients, which are generally approved for food use, also give a fast or a delayed release when used as an encapsulant for DHC. Other encapsulants like acacia or malto- dextrin can also encapsulate DHC, and give a very fast release rate of DHC in gum.
  • the amount of coating or encapsulating ma ⁇ terial on the sweetener DHC also controls the length of time for its release from chewing gum. Generally, the higher the level of coating and the lower the amount of active DHC, the slower the release of the sweetener during mastication. The release is generally not in ⁇ stantaneous, but gradual over an extended period of time.
  • the encapsulant should be a minimum of about 20% of the coated sweetener. Preferably, the encapsulant should be a minimum of about 30% of the coated sweetener, and most preferably should be a minimum of about 40% of the coated sweetener. Depending on the coating material, a higher or lower amount of coating material may be needed to give the desired release of sweetener to balance sweetness release with flavor release.
  • Another method of giving a delayed release of the sweetener, DHC is agglomeration of the sweetener with an agglomerating agent which partially coats the sweetener.
  • This method includes the step of mixing the sweetener and agglomerating agent with a small amount of water or solvent. The mixture is prepared in such a way as to have individual wet particles in contact with each other so that a partial coating can be applied. After the water or solvent is removed, the mixture is ground and used as a powdered, coated sweetener.
  • agglomerat ⁇ ing agent Materials that can be used as the agglomerat ⁇ ing agent are the same as those used in encapsulation procedures mentioned previously. However, since the coating is only a partial encapsulation, and the DHC sweetener is slightly water soluble, some agglomerating agents are more effective in delaying the sweetener release than others. Some of the better agglomerating agents are the organic polymers like acrylic polymers and copolymers, polyvinyl acetate, polyvinylpyrroli- done, waxes, shellac, and Zein. Other agglomerating agents are not as effective in giving the sweetener a delayed release as are the polymers, waxes, shellac and Zein, but can be used to give some delayed release.
  • agglomerating agents include, but are not limited to, agar, alginates, a wide range of cellulose derivatives like ethyl cellulose, methyl cellulose, sodium hydroxymethyl cellulose, hydroxypropylmethyl cellulose, dextrin, gelatin, modified starches, and vegetable gums like guar gum, locust bean gum, and carrageenin.
  • Agglomerating agents like maltodextrin or acacia can be used to increase the rate of sweetener release. Even though the agglomerated sweetener is only partially coated, when the quantity of coating is increased compared to the quantity of DHC sweetener, the release of the sweetener can be increased or delayed for a longer time during mastication.
  • the level of coating used in the agglomerated product is a minimum of about 5%. Preferably the coating level is a minimum of about 15% and more preferably about 20%. Depending on the agglomerating agent, a higher or lower amount of agent may be needed to give the desired release of sweetener to balance sweetness release with flavor release.
  • the DHC sweetener may be coated in a two-step process or multiple step process. The sweetener may be encapsulated with any of the materials as described previously and then the encapsulated sweetener can be agglomerated as described previously to obtain an en ⁇ capsulated/agglomerated/sweetener product that could be used in chewing gum to give a more delayed release of sweetener.
  • DHC sweetener may be absorbed onto another component which is porous and become entrapped in the matrix of the porous component.
  • Common materials used for absorbing the sweetener include, but are not limited to, silicas, silicates, pharmasorb clay, spongelike beads or microbeads, amorphous sugars like spray-dried dextrose, sucrose, alditols, amorphous carbonates and hydroxides, including aluminum and calcium lakes, vegetable gums and other spray dried materials.
  • the amount of DHC sweetener that can be loaded onto the absorbant will vary. Generally materials like polymers or sponglike beads or microbeads, amorphous sugars and alditols and amorphous carbonates and hydroxides absorb an amount equal to about 10% to about 40% of the weight of the absorbant. Other materials like silicas and pharmasorb clays may be able to absorb about 20% to about 80% of the weight of the absorbant.
  • the general procedure for absorbing the sweetener onto the absorbent is as follows.
  • An absorbent like fumed silica powder can be mixed in a powder blender and an aqueous solution of the DHC sweetener can be sprayed onto the powder as mixing con ⁇ tinues.
  • the aqueous solution can be about 1% to 5% DHC solids, and higher solid levels may be used if temperatures up to 90°C are used. Generally water is - li ⁇ the solvent, but other solvents like alcohol could also be used if approved for use in food.
  • the powder mixes the liquid is sprayed onto the powder. Spraying is stopped before the mix becomes damp.
  • the still free-flowing powder is removed from the mixer and dried to remove the water or other solvent, and then ground to a specific particle size.
  • the fixative/sweetener can be coated by encapsulation. Either full or partial encapsulation may be used, de ⁇ pending on the coating composition used in the process. Full encapsulation may be obtained by coating with a polymer as in spray drying, spray chilling, fluid-bed coating, coacervation, or any other standard technique. A partial encapsulation or coating can be obtained by agglomeration of the fixative/sweetener mixture using any of the materials discussed above.
  • the three methods of use to obtain a controlled release of DHC sweetener are: (1) encapsulation by spray drying, fluid-bed coating, spray chilling and coacervation to give full or partial encapsulation, (2) agglomeration to give partial encapsulation and (3) fixation or entrapment/absorption which also gives partial encapsulation. These three methods, combined in any usable manner which physically isolates the DHC sweetener, reduces or increases its dissolvability or modifies the release of sweetener, are included in this invention.
  • the DHC sweetener may be added to the liquid inside a liquid center gum product.
  • the center fill of a gum product may comprise one or more carbohydrate syrups, glycerin, thickeners, flavors, acidulants, colors, sugars and sugar alcohols in conventional amounts.
  • the ingredients are combined in a conventional manner.
  • the DHC sweetener is dissolved in the center-fill liquid and the amount of DHC sweetener added to the center-fill liquid is about 10 ppm to about 500 ppm by weight of the entire chewing gum formula.
  • This method of using DHC * sweetener in chewing gum can allow for a lower usage level of the sweetener, can give the sweetener a smooth release rate, and can reduce or eliminate any possible reaction of the sweetener with gum base, flavor components or other components, yielding improved shelf stability.
  • Another method of isolating DHC sweetener from other chewing gum ingredients is to add DHC to the dusting compound of a chewing gum.
  • a rolling or dusting compound is applied to the surface of chewing gum as it is formed. This rolling or dusting compound serves to reduce sticking to machinery as it is formed, reduces sticking of the product to machinery as it is wrapped, and sticking to its wrapper after it is wrapped and being stored.
  • the rolling compound com ⁇ prises DHC sweetener in combination with mannitol, sorbitol, sucrose, starch, calcium carbonate, talc, other orally acceptable substances or a combination thereof.
  • the rolling compound constitutes from about 0.25% to about 10.0%, but preferably about 1% to about 3% of weight of the chewing gum composition.
  • the amount of DHC sweetener added to the rolling compound is about 0.05% to about 20% of the rolling compound- or about 5 ppm to about 500 ppm of the chewing gum com ⁇ position.
  • This method of using DHC sweetener in the chewing gum can allow a lower usage level of the sweetener, can give the sweetener a more controlled release rate, and can reduce or eliminate any possible reaction of the sweetener with gum base, flavor components, or other components, yielding improved shelf stability.
  • DHC sweetener Another method of isolating DHC sweetener is to use it in the coating/panning of a pellet chewing gum.
  • Pellet or ball gum is prepared as conventional chewing gum, but formed into pellets that are pillow shaped, or into balls.
  • the pellets/balls can be then sugar coated or panned by conventional panning techniques to make a unique sugar coated pellet gum.
  • the DHC sweetener is fairly stable and water soluble, and can be easily added to a sugar solution prepared for sugar panning.
  • DHC can also be added as a powder blended with other powders often used in some types of conventional panning procedures. Using DHC sweetener isolates the sweetener from other gum ingredients and modifies its release rate in chewing gum.
  • Levels of use of DHC may be about 10 ppm to about 1,000 ppm in the coating and about 5 ppm to about 500 ppm of the weight of the chewing gum product.
  • the weight of the coating may be about 20% to about 50% of the weight of the finished gum product.
  • panning modifiers including, but not limited to, gum arabic, maltodextrins, corn syrup, gelatin, cellulose type materials like carboxymethyl cellulose or hydroxymethyl cellulose, starch and modified starches, vegetable gums like alginates, locust bean gum, guar gum, and gum tragacanth, in ⁇ soluble carbonates like calcium carbonate or magnesium carbonate and talc.
  • Antitack agents may also be added as panning modifiers which allow the use of a variety of carbohydrates and sugar alcohols to be used in the development of new panned or coated gum products. Flavors may also be added with the sugar coating and with the DHC sweetener to yield unique product characteristics.
  • pan coating would also iso ⁇ late the DHC sweetener from the chewing gum in ⁇ gredients.
  • This technique is referred to as film coat ⁇ ing and is more common in pharmaceuticals than in chew ⁇ ing gum, but procedures are similar.
  • a film like shellac, Zein, or cellulose-type material is applied onto a pellet-type product forming a thin film on the surface of the product.
  • the film is applied by mixing the polymer, a plasticizer and a solvent (pigments are optional) and spraying the mixture onto the pellet sur ⁇ face. This is done in conventional type panning equip ⁇ ment, or in more advanced side-vended coating pans. When a solvent like alcohol is used, extra precautions are needed to prevent fires and explosions, and specialized equipment must be used.
  • Some film polymers can use water as the sol ⁇ vent in film coating. Recent advances in polymer re ⁇ search and in film coating technology eliminates the problem associated with the use of solvents in coating. These advances make it possible to apply aqueous films to a pellet or chewing gum product.
  • DHC sweetener As DHC sweetener is water soluble, it can be added to this aqueous film solution and applied with the film to the pellet or chewing gum product.
  • the aqueous film or even the alcohol solvent film, in which DHC is highly soluble may also contain a flavor along with the polymer and plasticizer.
  • DHC sweetener By adding DHC sweetener to the polymer/plasticizer/solvent system, either as an emulsion or solution, the sweetener can add sweetness to the flavor and a balanced flavor/sweetness can be obtained.
  • the DHC sweetener can also be dissolved in the aqueous solvent and coated on the surface with the aqueous film. This will give a unique sweetness release to a film coated product.
  • the previously described encapsulated, agglomerated, or absorbed high-potency sweetener may readily be incorporated into a chewing gum composition.
  • the remainder of the chewing gum ingredients are non- critical to the present invention. That is, the coated particles of high-potency sweetener can be incorporated into conventional chewing gum formulations in a con ⁇ ventional manner.
  • the preferred chewing gum formulation is a sugarless chewing gum.
  • the high-potency sweeteners may also be used in a sugar chewing gum to intensify and/or extend the sweetness thereof.
  • the coated high-potency sweetener may be used in either regular chewing gum or bubble gum.
  • a chewing gum composition typic ⁇ ally comprises a water-soluble bulk portion, a water- insoluble chewable gum base portion and typically water-insoluble flavoring agents.
  • the water-soluble portion dissipates with a portion of the flavoring agent over a period of time during chewing.
  • the gum base portion is retained in the mouth throughout the chew.
  • the insoluble gum base generally comprises elastomers, resins, fats and oils, waxes, softeners and inorganic fillers.
  • Elastomers may include polyisobuty- lene, isobutylene-isoprene copolymer and styrene buta ⁇ diene rubber, as well as natural latexes such as chicle.
  • Resins include polyvinylacetate and terpene resins.
  • Fats and oils may also be included in the gum base, including tallow, hydrogenated and partially hydrogenated vegetable oils, and cocoa butter.
  • Com ⁇ monly employed waxes include paraffin, microcrystalline and natural waxes such as beeswax and carnauba.
  • the insoluble gum base constitutes between about 5 to about 95 percent by weight of the gum. More preferably the insoluble gum base comprises between 10 and 50 percent by weight of the gum and most preferably about 20 to about 35 percent by weight of the gum.
  • the gum base typically also includes a filler component.
  • the filler component may be calcium carbon ⁇ ate, magnesium carbonate, talc, dicalcium phosphate or the like.
  • the filler may constitute between about 5 and about 60 percent by weight of the gum base. Pre ⁇ ferably, the filler comprises about 5 to about 50 per ⁇ cent by weight of the gum base.
  • Gum bases typically also contain softeners, including glycerol monostearate and glycerol triace ⁇ tate. Further, gum bases may also contain optional ingredients such as antioxidants, colors, and emulsi- fiers. The present invention contemplates employing any commercially acceptable gum base.
  • the water-soluble portion of the chewing gum may further comprise softeners, sweeteners, flavoring agents and combinations thereof.
  • Softeners are added to the chewing gum in order to optimize the chewability and mouth feel of the gum.
  • Softeners also known in the art as plasticizers or plasticizing agents, gener ⁇ ally constitute between about 0.5 to about 15.0 percent by weight of the chewing gum.
  • Softeners contemplated by the present invention include glycerin, lecithin, and combinations thereof.
  • aqueous sweetener solutions such as those containing sorbitol, hydrogen ⁇ ated starch hydrolysates, corn syrup and combinations thereof may be used as softeners and binding agents in gum.
  • sugar sweeteners of the present invention will most likely be used in sugarless gum formulations.
  • formula- tions containing sugar are also within the scope of the invention.
  • Sugar sweeteners generally include saccha- ride- containing components commonly known in the chew ⁇ ing gum art which comprise, but are not limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup solids and the like, alone or in any combination.
  • the coated high-potency sweeteners of the present invention can also be used in combination with other sugarless sweeteners.
  • sugarless sweet ⁇ eners include components with sweetening character ⁇ istics but which are devoid of the commonly known sugars and comprise, but are not limited to, sugar al ⁇ cohols such as sorbitol, mannitol, xylitol, hydrogen ⁇ ated starch hydrolysates, maltitol and the like, alone or in any combination.
  • coated high- potency sweeteners of the present invention can also be used in combination with uncoated high-potency sweet ⁇ eners or with high-potency sweeteners coated with other materials and by other techniques.
  • a flavoring agent may be present in the chew ⁇ ing gum in an amount within the range of from about 0.1 to about 10.0 weight percent and preferably from about 0.5 to about 3.0 weight percent of the gum.
  • the flavoring agents may comprise essential oils, synthetic flavors, or mixture thereof including, but not limited to, oils derived from plants and fruits such as citrus oils, fruit essences, peppermint oil, spearmint oil, clove oil, oil of wintergreen, anise, and the like. Artificial flavoring components are also contemplated for use in gums of the present invention. Those skilled in the art will recognize that natural and artificial flavoring agents may be combined in any sensorally acceptable blend. All such flavors and flavor blends are contemplated by the present in ⁇ vention.
  • Optional ingredients such as colors, e ulsi- fiers and pharmaceutical agents may be added to the chewing gum.
  • chewing gum is manufactured by sequentially adding the various chewing gum ingredients to a commercially available mixer known in the art. After the ingredients have been thoroughly mixed, the gum mass is discharged from the mixer and shaped into the desired form such as by rolling into sheets and cutting into sticks, extruding into chunks or casting into pellets.
  • the ingredients are mixed by first melting the gum base and adding it to the running mixer.
  • the base may also be melted in the mixer itself.
  • Color or emulsifiers may also be added at this time.
  • a softener such as glycerin may also be added at this time, along with syrup and a portion of the bulk ⁇ ing agent. Further portions of the bulking agent may then be added to the mixer.
  • a flavoring agent is typically added with the final portion of the bulking agent.
  • the coated sweetener of the present invention is preferably added after the final portion of bulking agent and flavor have been added.
  • the formulas listed in Table 1 comprise vari ⁇ ous sugar-free formulas in which NeoDHC can be added to gum after it is dissolved in various aqueous type solvents.
  • NeoDHC blend 0.01 0.20 1.0 1.0 1.0
  • Example 1 - DHC powder can be added directly to the gum.
  • Example 2 A 5.0 g portion of NeoDHC can be dissolved in 95.0 g hot water, making a 5.0% solution, and added to gum.
  • NeoDHC A 1.0 gram portion of NeoDHC can be dissolved in 99 grams of propylene glycol, making a 1.0% solution, and added to gum.
  • Example 4 A 1.0 gram portion of NeoDHC can be dissolved in 99 grams of glycerin, making a 1.0% solution, and added to gum.
  • Example 5 A 1.0 gram portion of NeoDHC can be dissolved in 99 grams of hot hydrogenated starch hydrolysates, making a 1.0% solution, and added to gum.
  • NeoDHC can be dissolved in water and emulsifiers can be added to the aqueous solution.
  • Example solutions can be prepared by dissolving 1.0 grams of NeoDHC in 84 grams hot water and adding 15 grams of emulsifiers of various hydrophilic-lipophilic balance (HLB) values to the solution. The mixtures can then be used in the following formulas.
  • HLB hydrophilic-lipophilic balance
  • Examples 12-16 The same as the formulations made in Examples 6-11, respectively, except that the flavor can be mixed together with the aqueous sweetener solution and emulsified before adding the mixture to the gum batch.
  • NeoDHC sweetener can also be blended into various base ingredients.
  • a typical base formula is as follows: Wt . %
  • the individual base components can be softened prior to their addition in the base manufacturing pro ⁇ cess.
  • NeoDHC can be added and mixed, and then the presoftened base/sweet ⁇ ener blend can be added to make the finished base.
  • NeoDHC can be mixed first with one of the base ingredients, and the mixed ingredient can then be used in making a base.
  • the ingredients blended with NeoDHC can then be used at the levels indicated in the typical base formula above.
  • Example 17 The terpene resin used to make the base is 99.8% polyterpene resin and 0.2% NeoDHC.
  • Example 18 The polyvinyl acetate used to make the base is 99.8% low M.W. polyvinyl acetate and 0.2% NeoDHC.
  • Example 19 The paraffin wax used to make the base is 99.6% paraffin wax and 0.4% NeoDHC.
  • NeoDHC may also be added to an otherwise complete gum base.
  • NeoDHC can be mixed with 99.95% of a gum base having the above listed typical formula.
  • the NeoDHC can be added near the end of the process after all the other ingredients are added.
  • NeoDHC sweetener The theoretical level of NeoDHC sweetener is 0.01% in the finished gum.
  • NeoDHC samples Using the following formulation of a sugar- free gum, a variety of encapsulated NeoDHC samples can be evaluated:
  • Active NeoDHC 0.01% for spray drying, the solids level of an aqueous or alcoholic solution can be about 10-50%, but preferred levels are indicated in the examples listed.
  • Example 22 - A 90% shellac, 10% active NeoDHC powder mixture is obtained by spray drying an alcohol/shellac/NeoDHC solution at total solids of 10%.
  • Example 23 A 50% shellac, 50% active NeoDHC powder mixture is obtained by spray drying an appropriate ratio alcohol/shellac/NeoDHC solution at 10% solids.
  • Example 24 A 70% Zein, 30% active NeoDHC powder mixture is obtained by spray drying an alcohol/Zein/NeoDHC solution at 10% solids.
  • Example 25 A 40% shellac, 60% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an alcohol/shellac solution at 20% solids.
  • Example 26 - -A 60% shellac, 40% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an alcohol/shellac solution of 20% solids.
  • Example 27 - A 40% Zein, 60% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an alcohol/Zein solution of 20% solids.
  • Example 28 An 85% wax, 15% active NeoDHC powder mixture is obtained by spray chilling a mixture of molten wax and NeoDHC.
  • Example 29 A 70% wax, 30% active NeoDHC powder mixture is obtained by spray chilling a mixture of molten wax and NeoDHC.
  • Example 30 A 70% Zein, 30% active NeoDHC powder mixture is obtained by spray drying an aqueous mixture of NeoDHC and Zein dispersed in an aqueous, high-pH (pH of 11.6-12.0) media at 10% solids.
  • Example 32 A 20% Zein, 20% shellac, 60% active NeoDHC powder mixture is obtained by spray drying an alcohol/shellac/NeoDHC mixture and then fluid-bed coating the spray dried product for a second coating of alcohol and Zein.
  • Example 22 to 32 would all give nearly com ⁇ plete encapsulation and would delay the release of NeoDHC sweetener when used in the sugarless gum formulation in Table 4.
  • the higher levels of coating would give a longer delayed release of sweetener than the lower levels of coating.
  • Example 33 An 80% gelatin, 20% active NeoDHC powder mixture is obtained by spray drying a gelatin/NeoDHC solution at 10% solids.
  • Example 34 A 30% hydroxypropylmethyl cellulose (HPMC), 70% NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an aqueous solution of HPMC at 10% solids.
  • HPMC hydroxypropylmethyl cellulose
  • Example 35 A 30% carboxymethyl cellulose, 70% active NeoDHC powder mixture is obtained by fluid bed coating NeoDHC with an aqueous solution of carboxy methyl cellulose at 10% solids.
  • Example 36 A 50% maltodextrin, 50% active NeoDHC powder mixture is obtained by spray drying an aqueous solution of NeoDHC and maltodextrin at 20% solids.
  • Example 37 A 40% gum arabic, 60% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an aqueous solution of gum arabic at 20% solids.
  • NeoDHC from Examples 33, 34 and 35 when used in the chewing gum formula in Table 4, might give a delayed release or fast release of sweetener. However, this delayed release would not be extended as much as in the previous examples (22-32), but might show some delayed release or fast release.
  • NeoDHC could also be used in gum as an agglomerated sweetener to give modified sweetness re ⁇ lease.
  • Agglomerated sweeteners can be prepared as in the following examples:
  • Example 38 A 15% hydroxypropylmethyl cel ⁇ lulose (HPMC), 85% active ' NeoDHC powder mixture is prepared by agglomerating NeoDHC and HPMC blended together, with water being added, and the resulting product being dried-and ground.
  • HPMC hydroxypropylmethyl cel ⁇ lulose
  • Example 39 A 15% gelatin, 85% active NeoDHC powder mixture is made by agglomerating NeoDHC and gelatin blended together, with water being added, and the resulting product being dried and ground.
  • Example 40 - A 10% Zein, 90% active NeoDHC powder mixture is made by agglomerating NeoDHC with an alcohol solution containing 25% Zein, and drying and grinding the resulting product.
  • Example 41 - A 15% shellac, 85% active NeoDHC powder mixture is made by agglomerating NeoDHC with an alcohol solution containing 25% shellac, and drying and grinding the resulting product.
  • Example 42 A 20% HPMC, 80% active NeoDHC powder mixture is obtained by agglomerating an HPMC and NeoDHC mixture blended together, with water being added, and the resulting product being dried and ground.
  • Example 43 A 20% Zein, 80% active NeoDHC powder mixture is obtained by agglomerating NeoDHC and Zein dissolved in high-pH water (11.6-12.0) at 15% solids, with the resulting product being dried and ground.
  • Example 44 A 20% wax, 80% active NeoDHC powder mixture is obtained by agglomerating NeoDHC and molten wax, and cooling and grinding the resulting product.
  • Example 45 A 15% maltodextrin, 85% active NeoDHC powder mixture is obtained by agglomerating a blend of NeoDHC and maltodextrin, then adding water, drying and grinding.
  • NeoDHC agglomerated ma ⁇ terial
  • NeoDHC can also be used in sugar type gum formulations containing other sugars, such as in the following formulations A- G:
  • These formulations may also contain sugar alcohols such as sorbitol, mannitol, xylitol, lactitol, maltitol, palatinit, and lycasin or combinations thereof.
  • Sugarless type gum formulations with partially coated or fully coated NeoDHC can also be made using various sugar alcohols, such as the following formulations H-P: TABLE 7 (Wt. %)
  • Example 46 - NeoDHC is spray dried with maltodextrin at 10% solids to prepare a powder. This powder is then agglomerated with a hydroxypropylmethyl cellulose (HPMC) in a ratio of 85/15 powder/HPMC, wetted with water and dried. After grinding the resulting powder will contain about 68% active NeoDHC, 17% maltodextrin and 15% HPMC.
  • HPMC hydroxypropylmethyl cellulose
  • Example 47 - NeoDHC is agglomerated with HPMC in a ratio of 85/15 sweetener/HPMC. After drying and grinding, the resulting powder is fluid-bed coated with an alcohol/shellac solution at about 20% solids to give a final product containing about 60% active NeoDHC, 10% HPMC, and about 30% shellac.
  • Example 48 - NeoDHC is agglomerated with HPMC in a ratio of 85/15 Sweetener/HPMC. After drying and grinding, the resulting powder is agglomerated with a 15% solids, high-pH, aqueous solution of Zein to give a final product containing about 60% active NeoDHC, 10% HPMC, and 30% Zein. '
  • NeoDHC is spray dried with a 20% solution of gelatin.
  • the spray dried product is then agglomerated with a 15% solids, high-pH, aqueous r solution of Zein.
  • the final product will contain about 50% active NeoDHC, 20% gelatin, and 30% Zein.
  • Example 50 - NeoDHC is agglomerated with molten wax in a ratio of 85/15 sweetener/wax. When the mixture cools and is ground, it is fluid-bed coated with a 20% Zein - 80% alcohol solution, giving a final product containing 60% active NeoDHC, 10% wax and 30% Zein.
  • NeoDHC a delayed release and delayed sweetness.
  • These multiple step procedures can actually give more delayed release then the single step processes. Multiple step processes of more than two steps may give even longer delayed release times, but may generally become less cost effective and less efficient.
  • spray drying can be the first step, with additional steps of fluid-bed coating, spray chilling and agglomeration being part of the latter steps.
  • NeoDHC sweetener For absorption type examples, modified release of NeoDHC sweetener is dependent on the type of absorbing material. Most materials like silicas, sili ⁇ cates, cellulose, carbonates, and hydroxides would be expected to give a delayed release compared to amorphous sugar and sugar alcohols, which would give a fast release.
  • Example 51 A hot 10% solution of NeoDHC is sprayed onto a precipitated silica to absorb the sweetener. The mixture is dried and coated with a fumed silica. The final product is about 50% active NeoDHC.
  • Example 52 A hot 10% solution of NeoDHC is sprayed onto a pharmasorb clay to absorb the sweetener. The mixture is dried and ground and gives a final product of about 80% clay and 20% active NeoDHC.
  • Example 53 A hot 10% solution of NeoDHC is sprayed onto a microcrystalline cellulose powder to absorb the sweetener. The mixture is dried and ground and gives a product that is about 70% microcrystalline cellulose and 30% active NeoDHC.
  • Example 54 A hot 10% solution of NeoDHC is sprayed onto a high absorption starch to absorb the sweetener. The mixture is dried and ground and gives a product that is about 80% starch and 20% active NeoDHC.
  • Example 55 A hot 10% solution of NeoDHC is sprayed onto a calcium carbonate powder to absorb the sweetener. The mixture is dried and ground and gives a product of about 90% calcium carbonate and 10% active NeoDHC.
  • Example 56 A hot 10% solution of NeoDHC is sprayed onto a highly absorptive dextrose material to absorb the sweetener. The mixture is dried and ground and gives a product of about 80% dextrose and 20% active NeoDHC.
  • Example 57 A hot 10% solution of NeoDHC is sprayed onto a sorbitol powder to absorb the material. The mixture is dried and ground and gives a product of about 90% sorbitol and 10% active NeoDHC.
  • the samples prepared in examples 51-57 can be used in gum formulations as noted in Tables 5, 6, and 7. Those preparations which have NeoDHC absorbed onto a material that is not water soluble are expected to give a delayed release of NeoDHC sweetener. Those preparations having NeoDHC absorbed onto water soluble materials are expected to give a fast release.
  • NeoDHC NeoDHC
  • sugar or sugar alcohol a sugar or sugar alcohol
  • resolidify the sweetener with sugar or sugar alcohol after both are mixed together in a molten state.
  • Example 58 - NeoDHC is added to molten sorbitol in a ratio of 90 parts sorbitol to 10 parts NeoDHC. After mixing, the blend is cooled and ground.
  • Example 59 - NeoDHC is added to molten dextrose in a ratio of 90 parts dextrose to 10 parts NeoDHC. After mixing, the blend is cooled and ground.
  • Example 60 - 1% NeoDHC is dissolved in 99% high fructose corn syrup. The mixture is evaporated to a low moisture and ground.
  • examples 58-60 may be added to the gum formulations shown in Tables 5, 6 and 7 and -are expected to give a fast release of NeoDHC.
  • NeoDHC sweetener may be obtained by combining the various processes of encapsulation, agglomeration, absorption, and entrapment.
  • Any of the preparations made in Examples 51-60 can be further treated in fluid-bed coating, spray chilling, or coacervation processes to encapsulate the product, and can be agglomerated with various materials and procedures in a variety of multiple step processes.
  • NeoDHC sweetener may also be used with a variety of other high-intensity sweeteners and blended together before encapsulation, agglomeration, absorption, and entrapment. Some examples are:
  • Example 61 - NeoDHC and aspartame are blended together in a 1/5 ratio as a powder. This mixture is then spray chilled with wax in a ratio of 60/40 mix ⁇ ture/wax to obtain a powder containing 10% NeoDHC, 50% aspartame, and 40% wax.
  • Example 62 - NeoDHC and thaumatin in a 1/1 ratio are dissolved in water with a 10% solution of gelatin and spray dried. This spray dried powder is then agglomerated with a high-pH aqueous 15% Zein solu ⁇ tion. The mixture is dried and ground and gives a pro ⁇ duct containing 25% NeoDHC, 25% thaumatin, 35% gelatin, and 15% Zein.
  • Example 63 - NeoDHC and alitame in a 1/1 ratio are prepared in a hot 10% solution. This solution is sprayed onto a high absorption silica powder. The mixture is dried, ground and fluid-bed coated with an alcohol/shellac mixture, giving a product that contains 20% NeoDHC, 20% alitame, 40% silica, and 20% shellac.
  • Example 64 - NeoDHC and sodium cyclamate in a 1/5 ratio are blended together as a powder and then - agglomerated with water and hydroxypropylmethyl cellu ⁇ lose (HPMC). This blend is dried, ground and ag ⁇ glomerated further with a high-pH, aqueous 15% solution of Zein to obtain a product containing 55% sodium cyclamate, 11% NeoDHC, 14% HPMC and 20% Zein.
  • Example 65 Sucralose and NeoDHC in a 3/1 ratio are blended together as a powder and fluid-bed coated with a solution of 25% shellac in alcohol.
  • the coated product is agglomerated further with water and hydroxypropylmethyl cellulose (HPMC) to obtain a product containing 45% sucralose, 15% NeoDHC, 25% shellac, and 15% HPMC.
  • HPMC hydroxypropylmethyl cellulose
  • Example 66 - NeoDHC and sodium saccharin in a ratio of 1/5 are blended together as a powder and fluid bed coated with a solution of 25% shellac in alcohol.
  • the coated product is agglomerated further with water and hydroxypropylmethyl cellulose (HPMC) to obtain a product containing 10% NeoDHC, 50% sodium saccharin, 25% shellac, and 15% HPMC.
  • HPMC hydroxypropylmethyl cellulose
  • NeoDHC and other high- intensity sweeteners of Examples 61-66 are tested in gum formulations such as those noted in Tables 4, 5, 6 and 7, a significant delayed release of the sweetener and sweetness should be expected. This delayed release would improve the quality of flavor giving it the im ⁇ pression of a longer lasting flavor. Due to the syner- gistic effects of some of the sweetener combinations in Examples 61-66, less total sweetener can be used to give the same sweetness level as the single delayed release NeoDHC sweetener.
  • NeoDHC may also be combined with other high intensity sweetener without encapsulation, agglom ⁇ eration, or absorption and used in chewing gum, as in the following examples:
  • Example 67 - A combination of NeoDHC and aspartame can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.05% aspartame.
  • Example 68 - A combination of NeoDHC and thaumatin can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.01% thaumatin.
  • Example 69 - A combination of NeoDHC and sodium cyclamate can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.24% sodium cyclamate.
  • Example 70 - A combination of NeoDHC and acesulfame K can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.05% acesulfame K.
  • Example 71 - A combination of sucralose and NeoDHC can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.05% sucralose and 0.01% NeoDHC.
  • Example 72 A combination of NeoDHC and sodium saccharin can be used in the formulas listed in Tables 5, 6 and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.05% sodium saccharin.
  • Examples 68-72 may give a delayed release for those sweeteners which normally have a slow release. Some of these sweetener combinations may be synergistic, in which case less total sweetener may be needed to give the same sweetness level as a single sweetener.

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Abstract

The present invention includes a method for producing a chewing gum with a modified release dihydrochalcone sweetener, as well as the chewing gum so produced. The modified release dihydrochalcone sweetener is obtained by physically modifying dihydrochalcone properties by coating and drying. Dihydrochalcone sweetener is coated by encapsulation, partially coated by agglomeration, entrapped by absorption, or treated by multiple steps of encapsulation, agglomeration, and absorption. The coated sweetener is then co-dried and particle sized to produce a release-modified dihydrochalcone high-intensity sweetener. When incorporated into the chewing gum, these particles are adapted to enhance the shelf stability of the sweetener and/or produce a modified release when the gum is chewed.

Description

METHOD OF CONTROLLING RELEASE OF
DIHYDROCHALCONES IN CHEWING GUM
AND GUM PRODUCED THEREBY
BACKGROUND OF THE INVENTION
The present invention relates to methods for producing chewing gum. More particularly the invention relates to producing chewing gum containing high- potency sweeteners which have been treated to control their release and enhance shelf-life stability.
In recent years, efforts have been devoted to controlling release characteristics of various ingredi¬ ents in chewing gum. Most notably, attempts have been made to delay the release of sweeteners and flavors in various chewing gum formulations to thereby lengthen the satisfactory chewing time of the gum. Delaying the release of sweeteners and flavors can also avoid an undesirable overpowering burst of sweetness or flavor during the initial chewing period. On the other hand, some ingredients have been treated so as to increase their rate of release in chewing gum.
In addition, other efforts have been directed at perfecting the use of high-potency sweeteners within the chewing gum formulation, to thereby increase the shelf-life stability of the ingredients, i.e. the pro¬ tection against degradation of the high-potency sweetener over time.
One such high potency sweetener is dihydrochalcone. This sweetener, which is not approved for use in food products or in chewing gum, is being considered by many European countries as a food additive. This high potency sweetener gives chewing gum a mild, fast sweetness release and a long, mild lingering sweetness and after taste. This type of sweetness does not balance with the various types of chewing gum flavors. Methods of treating the high potency sweetener to increase the sweetness release initially and control the release of sweetness in balance with the chewing gum flavor would therefore be a definite improvement.
The use of dihydrochalcone artificial sweeteners was disclosed in U.S. Patents Nos. 3,625,700; 3,826,856; 3,890,298; 3,932,678; 3,976,790; 4,025,535; 4,031,260; 4,055,678; 4,064,167; 4,087,558 and 4,283,434.
The use of dihydrochalcones in chewing gum has been disclosed in U.K. Patent No. 1,310,329; U.S. Patents Nos. 4,863,745; 3,821,417; 3,857,962; 4,001,453 and 4,087,557; and EPO Patent Applications Nos. 0 320 522 and 0 320 523.
U.S. Patent No. 3,653,923 discloses a composition of dihydrochalcone and a saccharin sweetener.
U.S. Patent No. 4,158,068 discloses a sweetener mixture of acesulfame and other sweeteners including dihydrochalcones.
U.S. Patent No. 4,254,155 discloses a process for preparing a dihydrochalcone-base sweetening composition containing neohesperidin dihydrochalcones, a taste modifier, and having an acidic pH.
U.S. Patent No. 4,085,232 discloses a sweetening composition comprising a dihydrochalcone, a sugar, cream of tarter and a vanilla flavor.
U.S. Patent No. 4,803,082 discloses a powdered flavor composition encapsulated in a matrix of thaumatin, dihydrochalcones, and a wax or fat. Other patents disclose how a sweetener like aspartame can be physically modified to control its release rate in chewing gum.
For example, U.S. Patent No. 4,597,970 to Sharma et al. teaches a process for producing an agglomerated sweetener wherein the sweetener is dispersed in a hydrophobic matrix consisting essenti¬ ally of lecithin, a glyceride, and a fatty acid or wax having a melting point between 25°C and 100°C. The method disclosed uses a spray-congealing step to form the sweetener-containing matrix into droplets, followed by a fluid-bed second coating on the agglomerated par¬ ticles.
U.S. Patent Nos. 4,515,769 and 4,386,106, both to Merrit et al., teach a two step process for preparing a delayed release flavorant for chewing gum. In this process, the flavorant is prepared in an emul¬ sion with a hydrophilic matrix. The emulsion is dried and ground, and the resulting particles are then coated with a water-impermeable substance.
U.S. Patent No. 4,230,687 to Sair et al. teaches a process for encasing an active ingredient to achieve gradual release of the ingredient in a product such as chewing gum. The method described involves adding the ingredient to an encapsulating material in the form of a viscous paste. High-shear mixing is used to achieve a homogeneous dispersion of the ingredient within the matrix, which is subsequently dried and ground.
U.S. Patent No. 4,139,639 to Bahoshy et al. teaches a process of "fixing" aspartame by co-drying (by spray drying or fluid-bed coating) a solution con¬ taining aspartame and an encapsulating agent, such as gum arabic, to thereby surround and protect the aspar¬ tame in the gum during storage. U.S. Patent No. 4,384,004 to Cea et al. teaches a method of encapsulating aspartame with vari¬ ous solutions of encapsulating agents using various encapsulation techniques, such as spray drying, in order to increase the shelf-stability of the aspartame.
U.S. Patent No. 4,634,593 to Stroz et al. teaches a method for producing controlled release sweeteners for confections, such as chewing gum. The method taught therein involves the use of an insoluble fat material which is mix mulled with the sweetener.
SUMMARY OF INVENTION
The present invention includes a method for producing chewing gum with a modified high-potency sweetener, specifically dihydrochalcones (DHC) , as well as the chewing gum so produced. The controlled- release, high-potency sweetener is obtained by modifying the sweetener by encapsulation, partial encapsulation or partial coating, entrapment or absorption with water-soluble materials or water- insoluble materials. The procedures for modifying the sweetener include spray drying, spray chilling, fluid- bed coating, coacervation, and other agglomerating and standard encapsulating techniques. The sweetener may also be absorbed onto an inert or water-insoluble material. The sweetener may be modified in a multiple step process comprising any of the processes or combination of processes noted. The sweetener, DHC, may also be combined with other sweeteners including, but not limited to, sucrose, dextrose, fructose, maltose, maltodextrin, xylose, palatinose, or others that are considered bulk sweeteners, as well as sugar alcohols including but not limited to sorbitol, mannitol, xylitol, maltitol, lactitol, palatinit, and lycasin. The high-potency sweetener DHC may also be combined with other high-potency sweeteners including. but not limited to, thaumatin, aspartame, acesulfame K, sodium saccharin, sucralose, alitame, cyclamate, stevioside and glycyrrhizin.
This sweetener, DHC, when modified according to the present invention, gives a chewing gum having a controlled-release sweetener. A higher quantity of sweetener can be used having a controlled sweetness release that is compatible with the flavor release in chewing gum, giving a highly consumer-acceptable chewing gum product.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Dihydrochalcone (DHC) is a high-potency sweetener which is about 600-2000 times sweeter than sugar. The taste properties of DHC are considered good. At concentrations usually used, DHC has a mild sweet taste that does linger, and has a lingering aftertaste, with a slight licorice, menthol aftertaste.
The United States Food and Drug Administra¬ tion has not allowed DHC as a food additive. The manufacturer of DHC is Zoster, SA in Spain, and the distributor in the United States is Centerchem, Inc. of Tarrytown, New York. Dihydrochalcone (DHC) sweeteners may be either Neohesperidin Dihydrochalcone (NeoDHC), Naringin Dihydrochalcone (NDHC), or Hesperetin Dihydrochalcone 4'-β-D-glucoside (HDHCG) . Other DHC compounds may be sweeteners, but virtually all toxicology studies have been done on these three DHC sweeteners. Only NeoDHC is currently commercially available and approved for food use in a few countries.
When DHC is added to chewing gum at a level of about 0.001% to 0.1%, the sweetener gives chewing gum a mild sweetness that leaves a menthol/licorice flavor character. It would be considered a significant improvement to a chewing gum to have the DHC sweetener release its sweetness more slowly as the flavor in the gum is released, thus balancing the overall taste perception. This would also slow the release of the menthol/licorice aftertaste, so that more sweetener could be used without a significant aftertaste. Physical modifications of this sweetener would also improve its stability in the final product.
Dihydrochalcone can be added as a powder, as an aqueous solution, or dissolved in glycerine, propylene glycol, corn syrup, hydrogenated starch hydrolyzate, or any other compatible aqueous solutions.
For aqueous solutions, an emulsifier can also be mixed in the solution with the DHC sweetener and the mixture added to a chewing gum. A flavor can also be added to the sweetener/emulsifier mixture. The emulsion formed can be added to chewing gum. Powdered DHC may also be mixed into a molten chewing gum base during base manufacture or prior to manufacture of the gum. DHC may also be mixed with base ingredients during base manufacture.
Usage levels of DHC in water or aqueous solvent is limited to its solubility in the aqueous solvent. For NeoDHC, solubility in water at 25°C is 3.5 grams per liter and increases with temperature, to 650 grams per liter at 80°C. In most other aqueous solvents, like glycerine or propylene glycol, the solubility of NeoDHC is less than in plain water. NeoDHC is also soluble in ethanol and methanol. Whether as a powder or dissolved in liquid, the amount of DHC added to chewing gum of the present invention is about 0.001% to 0.1%. Preferably the range of DHC in gum is about 0.004% to 0.04%, or 40 to 400 ppm.
As stated previously, DHC releases slowly from chewing gum during the early stages of mastication of the gum because of its low solubility in water. Physical modifications of the sweetener by encapsulation with another substrate will increase its release in chewing gum by increasing the solubility or dissolution rate of DHC. Also, some modifications may make the DHC solubility even lower so that its release rate in chewing gum would be even more delayed. Any standard technique which gives partial or full encapsulation of the DHC sweetener can be used. These techniques include, but are not limited to, spray drying, spray chilling, fluid-bed coating and coacervation. These encapsulation techniques that give partial encapsulation or full encapsulation can be used individually or in any combination in a single step process or multiple step process. Generally, more delayed release of sweetener is obtained in multistep processes like spray drying the sweetener and then fluid-bed coating of the resultant powder. Generally, a fast release sweetener is obtained by a single step like spray drying the sweetener with water soluble materials.
The encapsulation techniques here described are standard coating techniques and generally give varying degrees of coating, from partial to full coat¬ ing, depending on the coating composition used in the process. Also, the coating compositions may be suscep¬ tible to water permeation to various degrees. Gener¬ ally, compositions that have high organic solubility, good film-forming properties and low water solubility give better delayed release of the sweetener. Such compositions include acrylic polymers and copolymers, carboxyvinyl polymer, polyamides, polystyrene, polyr vinyl acetate, polyvinyl acetate phthalate, polyvinyl- pyrrolidone, and waxes. Although all of these materials are possible for encapsulation of DHC sweetener, only food-grade materials should be con¬ sidered. Two standard food-grade coating materials that are good film formers but not water soluble are shellac and Zein. Others which are more water soluble. but good film formers, are materials like agar, algi- nates, a wide range of cellulose derivatives like ethyl cellulose, methyl cellulose, sodium hydroxymethyl cellulose, and hydroxypropylmethyl cellulose, dextrin, gelatin, and modified starches. These ingredients, which are generally approved for food use, also give a fast or a delayed release when used as an encapsulant for DHC. Other encapsulants like acacia or malto- dextrin can also encapsulate DHC, and give a very fast release rate of DHC in gum.
The amount of coating or encapsulating ma¬ terial on the sweetener DHC also controls the length of time for its release from chewing gum. Generally, the higher the level of coating and the lower the amount of active DHC, the slower the release of the sweetener during mastication. The release is generally not in¬ stantaneous, but gradual over an extended period of time. To obtain the desired sweetness release to blend with a gum's flavor release, the encapsulant should be a minimum of about 20% of the coated sweetener. Preferably, the encapsulant should be a minimum of about 30% of the coated sweetener, and most preferably should be a minimum of about 40% of the coated sweetener. Depending on the coating material, a higher or lower amount of coating material may be needed to give the desired release of sweetener to balance sweetness release with flavor release.
Another method of giving a delayed release of the sweetener, DHC, is agglomeration of the sweetener with an agglomerating agent which partially coats the sweetener. This method includes the step of mixing the sweetener and agglomerating agent with a small amount of water or solvent. The mixture is prepared in such a way as to have individual wet particles in contact with each other so that a partial coating can be applied. After the water or solvent is removed, the mixture is ground and used as a powdered, coated sweetener.
Materials that can be used as the agglomerat¬ ing agent are the same as those used in encapsulation procedures mentioned previously. However, since the coating is only a partial encapsulation, and the DHC sweetener is slightly water soluble, some agglomerating agents are more effective in delaying the sweetener release than others. Some of the better agglomerating agents are the organic polymers like acrylic polymers and copolymers, polyvinyl acetate, polyvinylpyrroli- done, waxes, shellac, and Zein. Other agglomerating agents are not as effective in giving the sweetener a delayed release as are the polymers, waxes, shellac and Zein, but can be used to give some delayed release. These other agglomerating agents include, but are not limited to, agar, alginates, a wide range of cellulose derivatives like ethyl cellulose, methyl cellulose, sodium hydroxymethyl cellulose, hydroxypropylmethyl cellulose, dextrin, gelatin, modified starches, and vegetable gums like guar gum, locust bean gum, and carrageenin. Agglomerating agents like maltodextrin or acacia can be used to increase the rate of sweetener release. Even though the agglomerated sweetener is only partially coated, when the quantity of coating is increased compared to the quantity of DHC sweetener, the release of the sweetener can be increased or delayed for a longer time during mastication. The level of coating used in the agglomerated product is a minimum of about 5%. Preferably the coating level is a minimum of about 15% and more preferably about 20%. Depending on the agglomerating agent, a higher or lower amount of agent may be needed to give the desired release of sweetener to balance sweetness release with flavor release. The DHC sweetener may be coated in a two-step process or multiple step process. The sweetener may be encapsulated with any of the materials as described previously and then the encapsulated sweetener can be agglomerated as described previously to obtain an en¬ capsulated/agglomerated/sweetener product that could be used in chewing gum to give a more delayed release of sweetener.
In another embodiment of this invention, DHC sweetener may be absorbed onto another component which is porous and become entrapped in the matrix of the porous component. Common materials used for absorbing the sweetener include, but are not limited to, silicas, silicates, pharmasorb clay, spongelike beads or microbeads, amorphous sugars like spray-dried dextrose, sucrose, alditols, amorphous carbonates and hydroxides, including aluminum and calcium lakes, vegetable gums and other spray dried materials.
Depending on the type of absorbant material and how it is prepared, the amount of DHC sweetener that can be loaded onto the absorbant will vary. Generally materials like polymers or sponglike beads or microbeads, amorphous sugars and alditols and amorphous carbonates and hydroxides absorb an amount equal to about 10% to about 40% of the weight of the absorbant. Other materials like silicas and pharmasorb clays may be able to absorb about 20% to about 80% of the weight of the absorbant.
The general procedure for absorbing the sweetener onto the absorbent is as follows. An absorbent like fumed silica powder can be mixed in a powder blender and an aqueous solution of the DHC sweetener can be sprayed onto the powder as mixing con¬ tinues. The aqueous solution can be about 1% to 5% DHC solids, and higher solid levels may be used if temperatures up to 90°C are used. Generally water is - li ¬ the solvent, but other solvents like alcohol could also be used if approved for use in food. As the powder mixes, the liquid is sprayed onto the powder. Spraying is stopped before the mix becomes damp. The still free-flowing powder is removed from the mixer and dried to remove the water or other solvent, and then ground to a specific particle size.
After the DHC sweetener is absorbed onto an absorbant or fixed onto an absorbant, the fixative/sweetener can be coated by encapsulation. Either full or partial encapsulation may be used, de¬ pending on the coating composition used in the process. Full encapsulation may be obtained by coating with a polymer as in spray drying, spray chilling, fluid-bed coating, coacervation, or any other standard technique. A partial encapsulation or coating can be obtained by agglomeration of the fixative/sweetener mixture using any of the materials discussed above.
The three methods of use to obtain a controlled release of DHC sweetener are: (1) encapsulation by spray drying, fluid-bed coating, spray chilling and coacervation to give full or partial encapsulation, (2) agglomeration to give partial encapsulation and (3) fixation or entrapment/absorption which also gives partial encapsulation. These three methods, combined in any usable manner which physically isolates the DHC sweetener, reduces or increases its dissolvability or modifies the release of sweetener, are included in this invention.
Other methods of treating the DHC sweetener to physically isolate the sweetener from other chewing gum ingredients may also have some effect on its release rate and stability. The DHC sweetener may be added to the liquid inside a liquid center gum product. The center fill of a gum product may comprise one or more carbohydrate syrups, glycerin, thickeners, flavors, acidulants, colors, sugars and sugar alcohols in conventional amounts. The ingredients are combined in a conventional manner. The DHC sweetener is dissolved in the center-fill liquid and the amount of DHC sweetener added to the center-fill liquid is about 10 ppm to about 500 ppm by weight of the entire chewing gum formula. This method of using DHC* sweetener in chewing gum can allow for a lower usage level of the sweetener, can give the sweetener a smooth release rate, and can reduce or eliminate any possible reaction of the sweetener with gum base, flavor components or other components, yielding improved shelf stability. Another method of isolating DHC sweetener from other chewing gum ingredients is to add DHC to the dusting compound of a chewing gum. A rolling or dusting compound is applied to the surface of chewing gum as it is formed. This rolling or dusting compound serves to reduce sticking to machinery as it is formed, reduces sticking of the product to machinery as it is wrapped, and sticking to its wrapper after it is wrapped and being stored. The rolling compound com¬ prises DHC sweetener in combination with mannitol, sorbitol, sucrose, starch, calcium carbonate, talc, other orally acceptable substances or a combination thereof. The rolling compound constitutes from about 0.25% to about 10.0%, but preferably about 1% to about 3% of weight of the chewing gum composition. The amount of DHC sweetener added to the rolling compound is about 0.05% to about 20% of the rolling compound- or about 5 ppm to about 500 ppm of the chewing gum com¬ position. This method of using DHC sweetener in the chewing gum can allow a lower usage level of the sweetener, can give the sweetener a more controlled release rate, and can reduce or eliminate any possible reaction of the sweetener with gum base, flavor components, or other components, yielding improved shelf stability.
Another method of isolating DHC sweetener is to use it in the coating/panning of a pellet chewing gum. Pellet or ball gum is prepared as conventional chewing gum, but formed into pellets that are pillow shaped, or into balls. The pellets/balls can be then sugar coated or panned by conventional panning techniques to make a unique sugar coated pellet gum. The DHC sweetener is fairly stable and water soluble, and can be easily added to a sugar solution prepared for sugar panning. DHC can also be added as a powder blended with other powders often used in some types of conventional panning procedures. Using DHC sweetener isolates the sweetener from other gum ingredients and modifies its release rate in chewing gum. Levels of use of DHC may be about 10 ppm to about 1,000 ppm in the coating and about 5 ppm to about 500 ppm of the weight of the chewing gum product. The weight of the coating may be about 20% to about 50% of the weight of the finished gum product.
Conventional panning procedures generally coat with sucrose, but recent advances in panning have allowed the use of other carbohydrate materials to be used in the place of sucrose. Some of these components include, but are not limited to, dextrose, maltose, palatinose, xylitol, lactitol, palatinit and other new additols or a combination thereof. These materials may be blended with panning modifiers including, but not limited to, gum arabic, maltodextrins, corn syrup, gelatin, cellulose type materials like carboxymethyl cellulose or hydroxymethyl cellulose, starch and modified starches, vegetable gums like alginates, locust bean gum, guar gum, and gum tragacanth, in¬ soluble carbonates like calcium carbonate or magnesium carbonate and talc. Antitack agents may also be added as panning modifiers which allow the use of a variety of carbohydrates and sugar alcohols to be used in the development of new panned or coated gum products. Flavors may also be added with the sugar coating and with the DHC sweetener to yield unique product characteristics.
Another type of pan coating would also iso¬ late the DHC sweetener from the chewing gum in¬ gredients. This technique is referred to as film coat¬ ing and is more common in pharmaceuticals than in chew¬ ing gum, but procedures are similar. A film like shellac, Zein, or cellulose-type material is applied onto a pellet-type product forming a thin film on the surface of the product. The film is applied by mixing the polymer, a plasticizer and a solvent (pigments are optional) and spraying the mixture onto the pellet sur¬ face. This is done in conventional type panning equip¬ ment, or in more advanced side-vended coating pans. When a solvent like alcohol is used, extra precautions are needed to prevent fires and explosions, and specialized equipment must be used.
Some film polymers can use water as the sol¬ vent in film coating. Recent advances in polymer re¬ search and in film coating technology eliminates the problem associated with the use of solvents in coating. These advances make it possible to apply aqueous films to a pellet or chewing gum product. As DHC sweetener is water soluble, it can be added to this aqueous film solution and applied with the film to the pellet or chewing gum product. The aqueous film or even the alcohol solvent film, in which DHC is highly soluble, may also contain a flavor along with the polymer and plasticizer. By adding DHC sweetener to the polymer/plasticizer/solvent system, either as an emulsion or solution, the sweetener can add sweetness to the flavor and a balanced flavor/sweetness can be obtained. The DHC sweetener can also be dissolved in the aqueous solvent and coated on the surface with the aqueous film. This will give a unique sweetness release to a film coated product.
The previously described encapsulated, agglomerated, or absorbed high-potency sweetener may readily be incorporated into a chewing gum composition. The remainder of the chewing gum ingredients are non- critical to the present invention. That is, the coated particles of high-potency sweetener can be incorporated into conventional chewing gum formulations in a con¬ ventional manner. Naturally, the preferred chewing gum formulation is a sugarless chewing gum. However, the high-potency sweeteners may also be used in a sugar chewing gum to intensify and/or extend the sweetness thereof. The coated high-potency sweetener may be used in either regular chewing gum or bubble gum.
In general, a chewing gum composition typic¬ ally comprises a water-soluble bulk portion, a water- insoluble chewable gum base portion and typically water-insoluble flavoring agents. The water-soluble portion dissipates with a portion of the flavoring agent over a period of time during chewing. The gum base portion is retained in the mouth throughout the chew.
The insoluble gum base generally comprises elastomers, resins, fats and oils, waxes, softeners and inorganic fillers. Elastomers may include polyisobuty- lene, isobutylene-isoprene copolymer and styrene buta¬ diene rubber, as well as natural latexes such as chicle. Resins include polyvinylacetate and terpene resins. Fats and oils may also be included in the gum base, including tallow, hydrogenated and partially hydrogenated vegetable oils, and cocoa butter. Com¬ monly employed waxes include paraffin, microcrystalline and natural waxes such as beeswax and carnauba. According to the preferred embodiment of the present invention, the insoluble gum base constitutes between about 5 to about 95 percent by weight of the gum. More preferably the insoluble gum base comprises between 10 and 50 percent by weight of the gum and most preferably about 20 to about 35 percent by weight of the gum.
The gum base typically also includes a filler component. The filler component may be calcium carbon¬ ate, magnesium carbonate, talc, dicalcium phosphate or the like. The filler may constitute between about 5 and about 60 percent by weight of the gum base. Pre¬ ferably, the filler comprises about 5 to about 50 per¬ cent by weight of the gum base.
Gum bases typically also contain softeners, including glycerol monostearate and glycerol triace¬ tate. Further, gum bases may also contain optional ingredients such as antioxidants, colors, and emulsi- fiers. The present invention contemplates employing any commercially acceptable gum base.
The water-soluble portion of the chewing gum may further comprise softeners, sweeteners, flavoring agents and combinations thereof. Softeners are added to the chewing gum in order to optimize the chewability and mouth feel of the gum. Softeners, also known in the art as plasticizers or plasticizing agents, gener¬ ally constitute between about 0.5 to about 15.0 percent by weight of the chewing gum. Softeners contemplated by the present invention include glycerin, lecithin, and combinations thereof. Further, aqueous sweetener solutions such as those containing sorbitol, hydrogen¬ ated starch hydrolysates, corn syrup and combinations thereof may be used as softeners and binding agents in gum.
As mentioned above, the coated high-potency sweeteners of the present invention will most likely be used in sugarless gum formulations. However, formula- tions containing sugar are also within the scope of the invention. Sugar sweeteners generally include saccha- ride- containing components commonly known in the chew¬ ing gum art which comprise, but are not limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup solids and the like, alone or in any combination.
The coated high-potency sweeteners of the present invention can also be used in combination with other sugarless sweeteners. Generally sugarless sweet¬ eners include components with sweetening character¬ istics but which are devoid of the commonly known sugars and comprise, but are not limited to, sugar al¬ cohols such as sorbitol, mannitol, xylitol, hydrogen¬ ated starch hydrolysates, maltitol and the like, alone or in any combination.
Depending.on the particular sweetness release profile and shelf-stability needed, the coated high- potency sweeteners of the present invention can also be used in combination with uncoated high-potency sweet¬ eners or with high-potency sweeteners coated with other materials and by other techniques.
A flavoring agent may be present in the chew¬ ing gum in an amount within the range of from about 0.1 to about 10.0 weight percent and preferably from about 0.5 to about 3.0 weight percent of the gum. The flavoring agents may comprise essential oils, synthetic flavors, or mixture thereof including, but not limited to, oils derived from plants and fruits such as citrus oils, fruit essences, peppermint oil, spearmint oil, clove oil, oil of wintergreen, anise, and the like. Artificial flavoring components are also contemplated for use in gums of the present invention. Those skilled in the art will recognize that natural and artificial flavoring agents may be combined in any sensorally acceptable blend. All such flavors and flavor blends are contemplated by the present in¬ vention.
Optional ingredients such as colors, e ulsi- fiers and pharmaceutical agents may be added to the chewing gum.
In general, chewing gum is manufactured by sequentially adding the various chewing gum ingredients to a commercially available mixer known in the art. After the ingredients have been thoroughly mixed, the gum mass is discharged from the mixer and shaped into the desired form such as by rolling into sheets and cutting into sticks, extruding into chunks or casting into pellets.
Generally, the ingredients are mixed by first melting the gum base and adding it to the running mixer. The base may also be melted in the mixer itself. Color or emulsifiers may also be added at this time. A softener such as glycerin may also be added at this time, along with syrup and a portion of the bulk¬ ing agent. Further portions of the bulking agent may then be added to the mixer. A flavoring agent is typically added with the final portion of the bulking agent. The coated sweetener of the present invention is preferably added after the final portion of bulking agent and flavor have been added.
The entire mixing procedure typically takes from five to fifteen minutes, but longer mixing times may sometimes be required. Those skilled in the art will recognize that many variations of the above de¬ scribed procedure may be followed. Examples
The following examples of the invention and comparative examples are provided by way of explanation and illustration.
The formulas listed in Table 1 comprise vari¬ ous sugar-free formulas in which NeoDHC can be added to gum after it is dissolved in various aqueous type solvents.
TABLE 1 (Wt. %)
Example Examplee Example Example Example 1 2 3 4 5
Sorbitol 49.6 49.6 49.3 49.3 49.3
Manitol 8.0 8.0 8.0 8.0 8.0
Gum Base 25.5 25.5 25.5 25.5 25.5
Glycerin 8.4 8.2 7.7 7.7 7.7
Hydro¬ genated Starch Hydroly- sates 6.8 6.8 6.8 6.8 6.8
Lecithin 0.2 0.2 0.2 0.2 0.2
Pepper¬ mint Flavor 1.44 1.45 1.45 1.45 1.45
Color 0.05 0.05 0.05 0.05 0.05
Liquid/
NeoDHC blend 0.01 0.20 1.0 1.0 1.0
Example 1 - DHC powder can be added directly to the gum.
Example 2 - A 5.0 g portion of NeoDHC can be dissolved in 95.0 g hot water, making a 5.0% solution, and added to gum.
Example 3 - A 1.0 gram portion of NeoDHC can be dissolved in 99 grams of propylene glycol, making a 1.0% solution, and added to gum.
Example 4 - A 1.0 gram portion of NeoDHC can be dissolved in 99 grams of glycerin, making a 1.0% solution, and added to gum. Example 5 - A 1.0 gram portion of NeoDHC can be dissolved in 99 grams of hot hydrogenated starch hydrolysates, making a 1.0% solution, and added to gum.
In the next examples of a sugar gum formula¬ tion, NeoDHC can be dissolved in water and emulsifiers can be added to the aqueous solution. Example solutions can be prepared by dissolving 1.0 grams of NeoDHC in 84 grams hot water and adding 15 grams of emulsifiers of various hydrophilic-lipophilic balance (HLB) values to the solution. The mixtures can then be used in the following formulas.
TABLE 2
(Wt. %)
Example Example Example Example Example Example 6 7 8 9 10 11
Sugar 55.2 55.2 55.2 55.2 55.2 55.2
Base 19.2 19.2 19.2 19.2 19.2 19.2
Corn Syrup 12.9 12.9 12.9 12.9 12.9 12.9
Glycerine 0.9 0.9 0.9 0.9 0.9 0.9
Dextrose Monohydrate 9.9 9.9 9.9 9.9 9.9 9.9
Peppermint Flavor 0.9 0.9 0.9 0.9 0.9 0.9
Sweetener/ Emulsifier/ Water Mixture 1.0 1.0 1.0 1.0 1.0 1.0
None HLB=2 H B=4 HLB=6 HLB=9 HLB=12
Examples 12-16 - The same as the formulations made in Examples 6-11, respectively, except that the flavor can be mixed together with the aqueous sweetener solution and emulsified before adding the mixture to the gum batch.
NeoDHC sweetener can also be blended into various base ingredients. A typical base formula is as follows: Wt . %
Polyvinyl acetate 27
Synthetic rubber 13
Paraffin Wax 13
Fat 3
Glycerol Monostearate 5
Terpene Resin 27
Calcium Carbonate Filler 12 100%
The individual base components can be softened prior to their addition in the base manufacturing pro¬ cess. To the presoftened base component, NeoDHC can be added and mixed, and then the presoftened base/sweet¬ ener blend can be added to make the finished base. In the following examples, NeoDHC can be mixed first with one of the base ingredients, and the mixed ingredient can then be used in making a base. The ingredients blended with NeoDHC can then be used at the levels indicated in the typical base formula above.
Example 17 - The terpene resin used to make the base is 99.8% polyterpene resin and 0.2% NeoDHC.
Example 18 - The polyvinyl acetate used to make the base is 99.8% low M.W. polyvinyl acetate and 0.2% NeoDHC.
Example 19 - The paraffin wax used to make the base is 99.6% paraffin wax and 0.4% NeoDHC.
NeoDHC may also be added to an otherwise complete gum base.
Example 20 - 0.05% NeoDHC can be mixed with 99.95% of a gum base having the above listed typical formula. The NeoDHC can be added near the end of the process after all the other ingredients are added.
The samples of finished base made with NeoDHC added to different base components can then be evaluated in a sugar-type chewing gum formulated as follows:
TABLE 3
(Wt, % ) (For examples 17, 18, 19, and 20)
Sugar 55.2
Base 19.2
Corn Syrup 13.4
Glycerine 1.4
Dextrose
Monohydrate 9.9
Peppermint Flavor 0.9
100%
The theoretical level of NeoDHC sweetener is 0.01% in the finished gum.
Using the following formulation of a sugar- free gum, a variety of encapsulated NeoDHC samples can be evaluated:
Table 4
(Wt. %)
Sorbitol 49.5
Manitol 8.0
Gum Base 25.5
Glycerin 8.5
Lycasin 6.8
Lecithin 0.2
Peppermint Flavor 1.44
Color 0.05
Active NeoDHC 0.01% For spray drying, the solids level of an aqueous or alcoholic solution can be about 10-50%, but preferred levels are indicated in the examples listed. Example 22 - A 90% shellac, 10% active NeoDHC powder mixture is obtained by spray drying an alcohol/shellac/NeoDHC solution at total solids of 10%.
Example 23 - A 50% shellac, 50% active NeoDHC powder mixture is obtained by spray drying an appropriate ratio alcohol/shellac/NeoDHC solution at 10% solids.
Example 24 - A 70% Zein, 30% active NeoDHC powder mixture is obtained by spray drying an alcohol/Zein/NeoDHC solution at 10% solids.
Example 25 - A 40% shellac, 60% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an alcohol/shellac solution at 20% solids.
Example 26 - -A 60% shellac, 40% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an alcohol/shellac solution of 20% solids.
Example 27 - A 40% Zein, 60% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an alcohol/Zein solution of 20% solids.
Example 28 - An 85% wax, 15% active NeoDHC powder mixture is obtained by spray chilling a mixture of molten wax and NeoDHC.
Example 29 - A 70% wax, 30% active NeoDHC powder mixture is obtained by spray chilling a mixture of molten wax and NeoDHC.
Example 30 - A 70% Zein, 30% active NeoDHC powder mixture is obtained by spray drying an aqueous mixture of NeoDHC and Zein dispersed in an aqueous, high-pH (pH of 11.6-12.0) media at 10% solids.
Example 31 - A 20% Zein, 80% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with a an aqueous, high-pH (pH=ll.6-12.0) Zein dispersion of 10% solids. Example 32 - A 20% Zein, 20% shellac, 60% active NeoDHC powder mixture is obtained by spray drying an alcohol/shellac/NeoDHC mixture and then fluid-bed coating the spray dried product for a second coating of alcohol and Zein.
Example 22 to 32 would all give nearly com¬ plete encapsulation and would delay the release of NeoDHC sweetener when used in the sugarless gum formulation in Table 4. The higher levels of coating would give a longer delayed release of sweetener than the lower levels of coating.
Other polymers that are more water soluble would have less of an effect of delaying the release of the "NeoDHC sweetener and may increase the release of the sweetener if used in the coating.
Example 33 - An 80% gelatin, 20% active NeoDHC powder mixture is obtained by spray drying a gelatin/NeoDHC solution at 10% solids.
Example 34 - A 30% hydroxypropylmethyl cellulose (HPMC), 70% NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an aqueous solution of HPMC at 10% solids.
Example 35 - A 30% carboxymethyl cellulose, 70% active NeoDHC powder mixture is obtained by fluid bed coating NeoDHC with an aqueous solution of carboxy methyl cellulose at 10% solids.
Example 36 - A 50% maltodextrin, 50% active NeoDHC powder mixture is obtained by spray drying an aqueous solution of NeoDHC and maltodextrin at 20% solids.
Example 37 - A 40% gum arabic, 60% active NeoDHC powder mixture is obtained by fluid-bed coating NeoDHC with an aqueous solution of gum arabic at 20% solids.
The coated NeoDHC from Examples 33, 34 and 35, when used in the chewing gum formula in Table 4, might give a delayed release or fast release of sweetener. However, this delayed release would not be extended as much as in the previous examples (22-32), but might show some delayed release or fast release. The product coated with maltodextrin and gum arabic in Examples 36 and 37, when used in the gum formula in Table 4, would show a fast release of sweetener in chewing gum compared to NeoDHC added directly.
NeoDHC could also be used in gum as an agglomerated sweetener to give modified sweetness re¬ lease. Agglomerated sweeteners can be prepared as in the following examples:
Example 38 - A 15% hydroxypropylmethyl cel¬ lulose (HPMC), 85% active 'NeoDHC powder mixture is prepared by agglomerating NeoDHC and HPMC blended together, with water being added, and the resulting product being dried-and ground.
Example 39 - A 15% gelatin, 85% active NeoDHC powder mixture is made by agglomerating NeoDHC and gelatin blended together, with water being added, and the resulting product being dried and ground.
Example 40 - A 10% Zein, 90% active NeoDHC powder mixture is made by agglomerating NeoDHC with an alcohol solution containing 25% Zein, and drying and grinding the resulting product.
Example 41 - A 15% shellac, 85% active NeoDHC powder mixture is made by agglomerating NeoDHC with an alcohol solution containing 25% shellac, and drying and grinding the resulting product.
Example 42 - A 20% HPMC, 80% active NeoDHC powder mixture is obtained by agglomerating an HPMC and NeoDHC mixture blended together, with water being added, and the resulting product being dried and ground.
Example 43 - A 20% Zein, 80% active NeoDHC powder mixture is obtained by agglomerating NeoDHC and Zein dissolved in high-pH water (11.6-12.0) at 15% solids, with the resulting product being dried and ground.
Example 44 - A 20% wax, 80% active NeoDHC powder mixture is obtained by agglomerating NeoDHC and molten wax, and cooling and grinding the resulting product.
Example 45 - A 15% maltodextrin, 85% active NeoDHC powder mixture is obtained by agglomerating a blend of NeoDHC and maltodextrin, then adding water, drying and grinding.
All of the above mixtures can be added to any of the following types of chewing gum formulas:
TABLE 5
(Wt. %)
Sugar Sugarless Sugarless
With With With Sugarless
Sugar Sorbitol Water Lye sin No Water
Gum Base 19.2 19.2 25.5 25.5 25.5
Sugar 55.495 53.495 — — —
Sorbitol — 2.0 53.8 49.5 52.3
Mannitol — — 8.0 8.0 12.0
Corn Syrup 13.1 13.1 — — —
Lycasin/ — 9.5<a> 6.8(b> —
Sorbitol liquid
Glycerin 1.4 1.4 1.5 8.5 8.5
Lecithin — — 0.2 0.2 0.2
Dextrose 9.9 9.9 ___
Monohydrate
Flavor 0.9 0.9 1.49 1.49 1.49
Level of 0.005 0.005 0.01 0.01 0.01
Active
NeoDHC
(a) liquid sorbitol (70% sorbitol, 30% water)
(b) hydrogenated starch hydrolyzate syrup
If each of the examples of agglomerated ma¬ terial (38-45) were evaluated in the formulations shown in Table 5, all samples except Example 45 with malto¬ dextrin would give NeoDHC a modified release. Samples using Zein, wax, and shellac would give the slowest release rate, whereas samples with HPMC and gelatin would give a moderate release. Maltodextrin would give a fast release of the NeoDHC sweetener.
Partially coated or fully coated NeoDHC can also be used in sugar type gum formulations containing other sugars, such as in the following formulations A- G:
TABLE 6 (Wt. %)
A B C D E F G
Gum Base 19.2. 19.2 19.2 19.2 19.2 19.2 19.2
Sugar 59.4 50.4 49.4 49.4 50.4 52.4 52.4
Glycerin 1.4 1.4 1.4 1.4 1.4 1.4 1.4
Corn Syrup 19.0 23.0 19.0 19.0 23.0 16.0 16.0
Dextrose — — 5.0 — — — —
Lactose — — — — 5.0 — —
Fructose — — 5.0 — — — —
Invert Sugar — — — 10.0 — — —
Maltose — — — — — 10.0 —
Palatinose — — — — — — 10.0
Corn Syrup — 5.0 — — — — — Solids
Peppermint 0.99 0.99 0.99 0.99 0.99 0.99 0.99
Flavor
Level of 0.01 0.01 0.01 0.01 0.01 0.01 0.01
Active NeoDHC
These formulations may also contain sugar alcohols such as sorbitol, mannitol, xylitol, lactitol, maltitol, palatinit, and lycasin or combinations thereof. Sugarless type gum formulations with partially coated or fully coated NeoDHC can also be made using various sugar alcohols, such as the following formulations H-P: TABLE 7 (Wt. %)
H M
Base 25.5 25.5 25.5 25.5 25.5 25.5 25.5 25.5 25.5
Sorbitol 53.9 46.9 41.9 41.9 41.9 41.9 36.9 37.9 46.9
Sorbitol 17.0 14.0 6.0 — 5.0 — 6.0<a> 18.0(a>
Liquid/
Lycasin
Mannitol — 10.0 8.0 8.0 8.0 8.0 8.0 8.0 8.0
Maltitol — — — 5.0 — — 5.0
Xylitol — — 15.0 10.0 — — 5.0 15.0
Lactitol — — — — 10.0 —
Palatinit — — — — — 15.0 10.0
Glycerin 2.0 2.0 2.0 8.0 8.0 8.0 8.0 6.0 —
Flavor 1.59 1.59 1.59 1.59 1.59 1.59 1.59 1.59 1.59
Level of 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01
Active
NeoDHC
(a) lycasin, all others use sorbitol liquid
All of these formulations in Table 6 and Table 7 which use the agglomerated NeoDHC as described in the examples (38-45) and in the previous encapsulation examples (22-35) would be expected to give a modified release of sweetness compared to a product made by adding NeoDHC directly to gum as a powder.
Multiple step agglomeration/encapsulation procedures can also be used in making release-modified sweeteners for use in the formulations in Tables 5, 6 and 7. Examples of multiple step treatments are here described:
Example 46 - NeoDHC is spray dried with maltodextrin at 10% solids to prepare a powder. This powder is then agglomerated with a hydroxypropylmethyl cellulose (HPMC) in a ratio of 85/15 powder/HPMC, wetted with water and dried. After grinding the resulting powder will contain about 68% active NeoDHC, 17% maltodextrin and 15% HPMC.
Example 47 - NeoDHC is agglomerated with HPMC in a ratio of 85/15 sweetener/HPMC. After drying and grinding, the resulting powder is fluid-bed coated with an alcohol/shellac solution at about 20% solids to give a final product containing about 60% active NeoDHC, 10% HPMC, and about 30% shellac.
Example 48 - NeoDHC is agglomerated with HPMC in a ratio of 85/15 Sweetener/HPMC. After drying and grinding, the resulting powder is agglomerated with a 15% solids, high-pH, aqueous solution of Zein to give a final product containing about 60% active NeoDHC, 10% HPMC, and 30% Zein. '
Example 49 - NeoDHC is spray dried with a 20% solution of gelatin. - The spray dried product is then agglomerated with a 15% solids, high-pH, aqueous r solution of Zein. The final product will contain about 50% active NeoDHC, 20% gelatin, and 30% Zein.
Example 50 - NeoDHC is agglomerated with molten wax in a ratio of 85/15 sweetener/wax. When the mixture cools and is ground, it is fluid-bed coated with a 20% Zein - 80% alcohol solution, giving a final product containing 60% active NeoDHC, 10% wax and 30% Zein.
These examples 46-50, when used in any of the formulations noted in Tables 5, 6, and 7 above, give NeoDHC a delayed release and delayed sweetness. These multiple step procedures can actually give more delayed release then the single step processes. Multiple step processes of more than two steps may give even longer delayed release times, but may generally become less cost effective and less efficient. Preferably spray drying can be the first step, with additional steps of fluid-bed coating, spray chilling and agglomeration being part of the latter steps.
For absorption type examples, modified release of NeoDHC sweetener is dependent on the type of absorbing material. Most materials like silicas, sili¬ cates, cellulose, carbonates, and hydroxides would be expected to give a delayed release compared to amorphous sugar and sugar alcohols, which would give a fast release. Some examples:
Example 51 - A hot 10% solution of NeoDHC is sprayed onto a precipitated silica to absorb the sweetener. The mixture is dried and coated with a fumed silica. The final product is about 50% active NeoDHC.
Example 52 - A hot 10% solution of NeoDHC is sprayed onto a pharmasorb clay to absorb the sweetener. The mixture is dried and ground and gives a final product of about 80% clay and 20% active NeoDHC.
Example 53 - A hot 10% solution of NeoDHC is sprayed onto a microcrystalline cellulose powder to absorb the sweetener. The mixture is dried and ground and gives a product that is about 70% microcrystalline cellulose and 30% active NeoDHC.
Example 54 - A hot 10% solution of NeoDHC is sprayed onto a high absorption starch to absorb the sweetener. The mixture is dried and ground and gives a product that is about 80% starch and 20% active NeoDHC.
Example 55 - A hot 10% solution of NeoDHC is sprayed onto a calcium carbonate powder to absorb the sweetener. The mixture is dried and ground and gives a product of about 90% calcium carbonate and 10% active NeoDHC.
Example 56 - A hot 10% solution of NeoDHC is sprayed onto a highly absorptive dextrose material to absorb the sweetener. The mixture is dried and ground and gives a product of about 80% dextrose and 20% active NeoDHC.
Example 57 - A hot 10% solution of NeoDHC is sprayed onto a sorbitol powder to absorb the material. The mixture is dried and ground and gives a product of about 90% sorbitol and 10% active NeoDHC.
The samples prepared in examples 51-57 can be used in gum formulations as noted in Tables 5, 6, and 7. Those preparations which have NeoDHC absorbed onto a material that is not water soluble are expected to give a delayed release of NeoDHC sweetener. Those preparations having NeoDHC absorbed onto water soluble materials are expected to give a fast release.
Another modification or absorption technique is to dry the NeoDHC together with a sugar or sugar alcohol, or resolidify the sweetener with sugar or sugar alcohol, after both are mixed together in a molten state.
Example 58 - NeoDHC is added to molten sorbitol in a ratio of 90 parts sorbitol to 10 parts NeoDHC. After mixing, the blend is cooled and ground.
Example 59 - NeoDHC is added to molten dextrose in a ratio of 90 parts dextrose to 10 parts NeoDHC. After mixing, the blend is cooled and ground.
Example 60 - 1% NeoDHC is dissolved in 99% high fructose corn syrup. The mixture is evaporated to a low moisture and ground.
The product of examples 58-60 may be added to the gum formulations shown in Tables 5, 6 and 7 and -are expected to give a fast release of NeoDHC.
Many of the examples listed are single step processes. However, more delayed release of the NeoDHC sweetener may be obtained by combining the various processes of encapsulation, agglomeration, absorption, and entrapment. Any of the preparations made in Examples 51-60 can be further treated in fluid-bed coating, spray chilling, or coacervation processes to encapsulate the product, and can be agglomerated with various materials and procedures in a variety of multiple step processes.
The NeoDHC sweetener may also be used with a variety of other high-intensity sweeteners and blended together before encapsulation, agglomeration, absorption, and entrapment. Some examples are:
Example 61 - NeoDHC and aspartame are blended together in a 1/5 ratio as a powder. This mixture is then spray chilled with wax in a ratio of 60/40 mix¬ ture/wax to obtain a powder containing 10% NeoDHC, 50% aspartame, and 40% wax.
Example 62 - NeoDHC and thaumatin in a 1/1 ratio are dissolved in water with a 10% solution of gelatin and spray dried. This spray dried powder is then agglomerated with a high-pH aqueous 15% Zein solu¬ tion. The mixture is dried and ground and gives a pro¬ duct containing 25% NeoDHC, 25% thaumatin, 35% gelatin, and 15% Zein.
Example 63 - NeoDHC and alitame in a 1/1 ratio are prepared in a hot 10% solution. This solution is sprayed onto a high absorption silica powder. The mixture is dried, ground and fluid-bed coated with an alcohol/shellac mixture, giving a product that contains 20% NeoDHC, 20% alitame, 40% silica, and 20% shellac.
Example 64 - NeoDHC and sodium cyclamate in a 1/5 ratio are blended together as a powder and then - agglomerated with water and hydroxypropylmethyl cellu¬ lose (HPMC). This blend is dried, ground and ag¬ glomerated further with a high-pH, aqueous 15% solution of Zein to obtain a product containing 55% sodium cyclamate, 11% NeoDHC, 14% HPMC and 20% Zein.
Example 65 - Sucralose and NeoDHC in a 3/1 ratio are blended together as a powder and fluid-bed coated with a solution of 25% shellac in alcohol. The coated product is agglomerated further with water and hydroxypropylmethyl cellulose (HPMC) to obtain a product containing 45% sucralose, 15% NeoDHC, 25% shellac, and 15% HPMC.
Example 66 - NeoDHC and sodium saccharin in a ratio of 1/5 are blended together as a powder and fluid bed coated with a solution of 25% shellac in alcohol. The coated product is agglomerated further with water and hydroxypropylmethyl cellulose (HPMC) to obtain a product containing 10% NeoDHC, 50% sodium saccharin, 25% shellac, and 15% HPMC.
If the blends of NeoDHC and other high- intensity sweeteners of Examples 61-66 are tested in gum formulations such as those noted in Tables 4, 5, 6 and 7, a significant delayed release of the sweetener and sweetness should be expected. This delayed release would improve the quality of flavor giving it the im¬ pression of a longer lasting flavor. Due to the syner- gistic effects of some of the sweetener combinations in Examples 61-66, less total sweetener can be used to give the same sweetness level as the single delayed release NeoDHC sweetener.
NeoDHC may also be combined with other high intensity sweetener without encapsulation, agglom¬ eration, or absorption and used in chewing gum, as in the following examples:
Example 67 - A combination of NeoDHC and aspartame can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.05% aspartame.
Example 68 - A combination of NeoDHC and thaumatin can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.01% thaumatin. Example 69 - A combination of NeoDHC and sodium cyclamate can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.24% sodium cyclamate.
Example 70 - A combination of NeoDHC and acesulfame K can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.05% acesulfame K.
Example 71 - A combination of sucralose and NeoDHC can be used in the formulas listed in Tables 5, 6, and 7 by adjusting the formulas to contain 0.05% sucralose and 0.01% NeoDHC.
Example 72 - A combination of NeoDHC and sodium saccharin can be used in the formulas listed in Tables 5, 6 and 7 by adjusting the formulas to contain 0.01% NeoDHC and 0.05% sodium saccharin.
The formulations of Examples 68-72 may give a delayed release for those sweeteners which normally have a slow release. Some of these sweetener combinations may be synergistic, in which case less total sweetener may be needed to give the same sweetness level as a single sweetener.

Claims

I CLAIM :
1. A method for producing chewing gum with dihydrochalcones comprising the steps of: a) mixing a quantity of dihydrochalcones with a spray drying solvent and an encapsulating material; b) spray drying the mixture in such a way as to encapsulate the dihydrochalcones; and c) adding a quantity of the spray dried material to a chewing gum formulation to provide a dihydrochalcones level in the gum of from 0.001% to 0.1%.
2. The method of Claim 1 wherein the solvent is selected from the group consisting of alcohol and water.
3. The method of Claim 1 wherein the encapsula¬ ting material -is selected from the group consisting of shellac and Zein.
4. The method of Claim 1 wherein an additional high-potency sweetener selected from the group consis¬ ting of aspartame, alitame, salts of acesulfame, cycla¬ mate and its salts, saccharin and its salts, sucralose, thaumatin, monellin, glycyrrhizin, and combinations thereof is mixed in the spray drying mixture in combination with the dihydrochalcones.
5. A chewing gum made according to the method of Claim 1,
6. The method of Claim 1 wherein the dihydrochalcone is selected from the group consisting of neohesperidin dihydrochalcone, naringin dihydro- chalcone, hesperetin dihydrochalcone 4'-β-D-glucoside, and food acceptable derivatives of dihydrochalcone.
7. A method for producing chewing gum with dihydrochalcone comprising the steps of: a) fluid-bed coating dihydrochalcone with a solution of an encapsulating material and a solvent; b) drying said fluid-bed coated material; and c) adding a quantity of the fluid-bed coated material to a chewing gum formulation to provide a dihydrochalcone level in the gum formulation of from about 0.001% to about 0.1%.
8. The method of Claim 7 wherein the solvent is selected from the group consisting of alcohol and water.
9. The method of Claim 7 wherein the encapsulat¬ ing material is selected from the group consisting of shellac and Zein.
10. The method of Claim 7 wherein an additional high-potency sweetener selected from the group consis¬ ting of aspartame, alitame, salts of acesulfame, cycla¬ mate and its salts, saccharin and its salts, sucralose, thaumatin, monellin, glycyrrhizin, and combinations thereof is mixed in the spray drying mixture in com¬ bination with the dihydrochalcone.
11. A chewing gum made according to the method of Claim 7.
12. The method of Claim 7 wherein the dihydrochalcone is selected from the group consisting of neohesperidin dihydrochalcone, naringin dihydrochalcone, hesperetin dihydrochalcone 4'-β-D- glucoside, and food acceptable derivatives of dihydrochalcone.
PCT/US1990/004005 1990-07-17 1990-07-17 Controlled release of dihydrochalcones in chewing gum WO1990013994A2 (en)

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WO1992005682A2 (en) * 1991-08-16 1992-04-16 Wm. Wrigley Jr. Company Spray dried flavor and gum base ingredient
US5139798A (en) * 1990-11-21 1992-08-18 Wm. Wrigley Jr. Company Polyvinyl acetate encapsulation of codried sucralose for use in chewing gum
EP0507598A1 (en) * 1991-04-05 1992-10-07 TATE &amp; LYLE PUBLIC LIMITED COMPANY Sweetening agents
US5192563A (en) * 1986-10-22 1993-03-09 Wm. Wrigley, Jr. Company Strongly mint-flavored chewing gums with reduced bitterness and harshness
US5270061A (en) * 1992-03-26 1993-12-14 Wm. Wrigley Jr. Company Dual composition hard coated gum with improved shelf life
US5286502A (en) * 1992-04-21 1994-02-15 Wm. Wrigley Jr. Company Use of edible film to prolong chewing gum shelf life
EP0722274A1 (en) * 1993-09-30 1996-07-24 Wm. Wrigley Jr. Company Chewing gum containing low levels of maltitol and a high-intensity sweetener
EP0784933A2 (en) * 1995-10-16 1997-07-23 Leaf, Inc. Extended release of additives in comestible products
US5665406A (en) * 1992-03-23 1997-09-09 Wm. Wrigley Jr. Company Polyol coated chewing gum having improved shelf life and method of making
EP1241949A1 (en) * 1999-12-30 2002-09-25 Wm. Wrigley Jr. Company Release of lipophilic active agents from chewing gum
US20050118273A1 (en) * 2001-11-15 2005-06-02 Yasushi Sasaki Microcapsules and oral composition containing the same
WO2006127934A2 (en) * 2005-05-23 2006-11-30 Cadbury Adams Usa, Llc Taste potentiator compositions and edible confectionery and chewing gum products containing same
EP0758849B1 (en) * 1994-05-06 2007-03-07 Wm. Wrigley Jr. Company Method for creating a chewing gum including a liquid sorbitol/mannitol/glycerin blend
US7727565B2 (en) 2004-08-25 2010-06-01 Cadbury Adams Usa Llc Liquid-filled chewing gum composition
US9011946B2 (en) 2011-04-29 2015-04-21 Intercontinental Great Brands Llc Encapsulated acid, method for the preparation thereof, and chewing gum comprising same
CN108752400A (en) * 2018-06-29 2018-11-06 湖南省农产品加工研究所 The preparation method of aurantiin dihydrochalcone

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US9198448B2 (en) 2005-02-07 2015-12-01 Intercontinental Great Brands Llc Stable tooth whitening gum with reactive ingredients

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US5192563A (en) * 1986-10-22 1993-03-09 Wm. Wrigley, Jr. Company Strongly mint-flavored chewing gums with reduced bitterness and harshness
US5139798A (en) * 1990-11-21 1992-08-18 Wm. Wrigley Jr. Company Polyvinyl acetate encapsulation of codried sucralose for use in chewing gum
EP0507598A1 (en) * 1991-04-05 1992-10-07 TATE &amp; LYLE PUBLIC LIMITED COMPANY Sweetening agents
WO1992005682A3 (en) * 1991-08-16 1992-05-29 Wrigley W M Jun Co Spray dried flavor and gum base ingredient
US5153011A (en) * 1991-08-16 1992-10-06 Wm. Wrigley Jr. Company Chewing gum flavor ingredient
WO1992005682A2 (en) * 1991-08-16 1992-04-16 Wm. Wrigley Jr. Company Spray dried flavor and gum base ingredient
US5665406A (en) * 1992-03-23 1997-09-09 Wm. Wrigley Jr. Company Polyol coated chewing gum having improved shelf life and method of making
US5270061A (en) * 1992-03-26 1993-12-14 Wm. Wrigley Jr. Company Dual composition hard coated gum with improved shelf life
US5286502A (en) * 1992-04-21 1994-02-15 Wm. Wrigley Jr. Company Use of edible film to prolong chewing gum shelf life
US5433960A (en) * 1992-04-21 1995-07-18 Wm. Wrigley Jr. Company Chewing gum including agent containing edible film
US5376388A (en) * 1992-04-21 1994-12-27 The Wm. Wrigley Jr. Company Use of edible film to improve the packaging of chewing gum
US5409715A (en) * 1992-04-21 1995-04-25 Wm. Wrigley Jr. Company Use of edible film to prolong chewing gum shelf life
EP0722274A1 (en) * 1993-09-30 1996-07-24 Wm. Wrigley Jr. Company Chewing gum containing low levels of maltitol and a high-intensity sweetener
EP0722274A4 (en) * 1993-09-30 1997-03-05 Wrigley W M Jun Co Chewing gum containing low levels of maltitol and a high-intensity sweetener
EP0758849B1 (en) * 1994-05-06 2007-03-07 Wm. Wrigley Jr. Company Method for creating a chewing gum including a liquid sorbitol/mannitol/glycerin blend
EP0784933A2 (en) * 1995-10-16 1997-07-23 Leaf, Inc. Extended release of additives in comestible products
EP0784933A3 (en) * 1995-10-16 1997-11-26 Leaf, Inc. Extended release of additives in comestible products
US5912030A (en) * 1995-10-16 1999-06-15 Leaf Inc. Comestible products having extended release of addititives and method of making
EP1241949A1 (en) * 1999-12-30 2002-09-25 Wm. Wrigley Jr. Company Release of lipophilic active agents from chewing gum
EP1241949A4 (en) * 1999-12-30 2004-12-08 Wrigley W M Jun Co Release of lipophilic active agents from chewing gum
US20050118273A1 (en) * 2001-11-15 2005-06-02 Yasushi Sasaki Microcapsules and oral composition containing the same
US7727565B2 (en) 2004-08-25 2010-06-01 Cadbury Adams Usa Llc Liquid-filled chewing gum composition
WO2006127934A2 (en) * 2005-05-23 2006-11-30 Cadbury Adams Usa, Llc Taste potentiator compositions and edible confectionery and chewing gum products containing same
WO2006127936A3 (en) * 2005-05-23 2007-03-08 Cadbury Adams Usa Llc Taste potentiator compositions and edible confectionery and chewing gum products containing same
WO2006127934A3 (en) * 2005-05-23 2007-03-08 Cadbury Adams Usa Llc Taste potentiator compositions and edible confectionery and chewing gum products containing same
US9011946B2 (en) 2011-04-29 2015-04-21 Intercontinental Great Brands Llc Encapsulated acid, method for the preparation thereof, and chewing gum comprising same
US9737082B2 (en) 2011-04-29 2017-08-22 Intercontinental Great Brands Llc Chewing gum composition comprising encapsulated acid
CN108752400A (en) * 2018-06-29 2018-11-06 湖南省农产品加工研究所 The preparation method of aurantiin dihydrochalcone
CN108752400B (en) * 2018-06-29 2020-05-22 湖南省农产品加工研究所 Preparation method of naringin dihydrochalcone

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