WO1993000828A2 - Composition edulcorante stabilisee - Google Patents

Composition edulcorante stabilisee Download PDF

Info

Publication number
WO1993000828A2
WO1993000828A2 PCT/US1992/004262 US9204262W WO9300828A2 WO 1993000828 A2 WO1993000828 A2 WO 1993000828A2 US 9204262 W US9204262 W US 9204262W WO 9300828 A2 WO9300828 A2 WO 9300828A2
Authority
WO
WIPO (PCT)
Prior art keywords
mixtures
encapsulated
group
sweetener
dipeptide
Prior art date
Application number
PCT/US1992/004262
Other languages
English (en)
Other versions
WO1993000828A3 (fr
Inventor
Subraman Rao Cherukuri
Tommy L. Chau
Dhananjaya Alli
Original Assignee
Warner-Lambert 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.)
Filing date
Publication date
Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company
Publication of WO1993000828A2 publication Critical patent/WO1993000828A2/fr
Publication of WO1993000828A3 publication Critical patent/WO1993000828A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/18—Chewing gum characterised by shape, structure or physical form, e.g. aerated products
    • A23G4/20—Composite products, e.g. centre-filled, multi-layer, laminated
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives

Definitions

  • the present invention relates generally to the
  • dipeptide sweetener known as aspartame (alpha-L-aspartyl-L-phenyalanine methyl ester) or APM has
  • the sweetener is not without its drawbacks. Of major significance is the sweetener's instability in the presence of heat, moisture and alkaline environments. This instability has prevented its use in most if not all 5 cooking and baking applications and is a factor that must be considered in products that require a long shelf life. Many attempts have been made using different coatings and/or physical/mechanical processing parameters to increase the
  • APM 35 vinyl polymers, gelatin, zein, waxes and mixtures thereof in a ratio of coating material to APM of 1:1 or less.
  • the APM is coated by conducting the APM particles in a stream of air that passes through a zone of atomized liquid droplets of the coating material thereby forming discrete layers about the APM particles under substantially anhydrous conditions.
  • the stabilized APM particles are particularly useful in chewing gum applications.
  • U.S. Patent No. 4,828,857 to Sharma et al discloses a sweetener delivery system wherein the sweetener core " material is formed in an agglomerate hydrophobic matrix by spray congealing.
  • the agglomerated matrix is selected 20 from the group consisting of waxes, fatty acids and mixtures thereof.
  • the agglomerated sweetener is then given a second coating of these hydrophobic materials and lecithin is added as a wetting agent to increase the affinity of the fat or wax for the APM crystals. Chewing 25 um and boiled hard candy are specifically taught applications for the sweetener delivery system.
  • U.S. Patent No. 4,722,845 to Cherukuri et al discloses a stable, cinnamon-flavored chewing gum composition wherein a dipeptide or amino acid sweetener 30 is protected from reacting with the degradative aldehydes of the flavor oil by encapsulating the sweetener in a mixture of fat and high melting point (106°) polyethylene wax.
  • the materials are coated onto the aspartame crystals using a modified spray congealing technique to " form aggregated particles that may be mixed into the gum base for longer lasting shelf life stability.
  • U.S. Patent No. 4,816,265 also to Cherukuri discloses chewing gum compositions containing APM that is encapsulated with a mixture of a low molecular weight polyvinyl acetate (PVA) and an emulsifier.
  • PVA polyvinyl acetate
  • the sweetener is blended into a homogeneous melted molten mass of PVA and the resultant mixture is a semi-solid mass which is cooled to a solid and ground into particles . with a U.S. standard mesh size of 30 to about 200.
  • the sweeteners are protected from adverse conditions such as moisture, pH, temperature and reactive, chemicals such as flavor oils in the gums.
  • Aspartame is first granulated to particles with a U.S. mesh size of from about 8 to about 40 that are then coated with partially dehydrogenated vegetable oil. Both the type of fat and particle size are critical to the
  • U.S Patent No. 4,816,265 to Zibell discloses chewing ' gum with a delayed release, high potency sweetener such as aspartame.
  • the APM is initially coated with modified
  • the APM particles are then mixed with a zein solution with a pH of from 11.5 to 12.5.
  • the damp mix is then dried to produce twice coated particles of the high intensity sweetener which allegedly enhance the shelf life
  • PCT Application No. PCT/US88/02398 also to Tsau discloses another heat stabilized form of APM wherein the dipeptide crystals are "spheronized" into dense,
  • non-porous granules of substantially spherical shape within a narrow particle size range.
  • the dense, spherical granules are preferably further encapsulated with a hydrophobic coating such as fats, starches, proteins and/or fibers and allegedly possess both
  • U.S. Patent No. 4,588,612 to Perkins et al discloses the compaction of needle-like crystals of a material such as aspartame into a plurality of dense chips which are then ground to an average particle size of 20 to 400 standard U.S. mesh. The granules are then spread on a . fluid bed spray reactor and encapsulated with a molten hydrogenated lipid or wax. The encapsulated aspartame granules are disclosed as being useful in baking applications since the encapsulating material essentially protects the granule from degradation that would fl otherwise result from the effects of heat and alkaline pH. The Perkins et al.
  • the present invention is an improved dipeptide sweetener with longer lasting shelf life stability that is particularly useful in chewing gum compositions and especially useful in cinnamon-flavored chewing gum.
  • the dipeptide sweetener is encapsulated through a hydrous process that compresses the crystals within a mixture of inert binder ingredients so as to form granules which are then further ground into a fine granular powder (40-60 U.S. Standard mesh).
  • the compressed cores are then coated with a hydrophobic material such as either fat or wax resulting in a dipeptide sweetener with improved shelf life stability in the presence of otherwise adverse flavor oils and high processing temperatures.
  • Figure 1 is a Differential Scanning Calorimetry profile of APM core materials of the present invention.
  • Figure 2. is a graph displaying the shelf life stability of the encapsulated aspartame compositions of Q the present invention in cinnamon gum as a function of percent APM remaining over time.
  • the dipeptide sweetener compositions of the present invention are stabilized by a process that imbeds the j needle-like, dendritic crystals of aspartame into a hydrous mixture of inert elements that further stabilize the sweetener from the adverse affects of temperature, ' moisture and reactive chemicals.
  • coatings such as fat, waxes, cellulose etc. have been used extensively in the past in an effort to protect materials such as aspartame from adverse conditions
  • the dendritic, needle-like shape of the crystals are highly irregular and difficult to impossible to coat in a complete and uniform manner.
  • mechanical stresses and/or forces would inevitably break them off leading to exposed and unprotected APM at numerous places which is unsatisfactory.
  • compositions of the present invention are 0 comprised of a dipeptide sweetener such as aspartame, alitame and others.
  • the sweetener is first combined in a hydrous mixture or blend of a number of inert compounds which serve in a protective and binding capacity.
  • the amount of dipeptide sweetener used can vary * depending upon the type of food application that it is used in and the degree of sweetness desired.
  • the sweetener can comprise anywhere from 5-70% by weight of the core material, preferably 15-45% and most preferably 20-40% of the total weight of the core material.
  • a binder component selected from the group consisting of gums, pectins, alginates, mucilages, microcrystalline cellulose and mixtures thereof may be employed.
  • the hydrocolloid may comprise gum arabic, tragacanth, karaya, .
  • the binder is the major component of the core blend and can comprise anywhere from about 10% to about 50% by weight of the core and preferably 15%-45% and most preferably 20% to
  • An inert material such as polyols, carbohydrates or calcium phosphates may optionally be added in a 0 protective capacity to prevent the core sweetener material from reacting with certain constituents of the flavor oils and other chemicals. Cinnamon for example, contains aldehyde groups which react with the dipeptide and result in a loss of sweetness.
  • Polyols suitable in 5 the practice of the present invention include sorbitol, mannitol, xylitol or erythritol and are added in order to stabilize the dipeptide from the adverse conditions of heat, moisture and flavor oils. Mannitol is the polyol most preferred in the practice of the present invention.
  • the polyols may be added to the hydrous blend in amounts from about 5.0% - 80.0%, preferably 10% - 50% and most preferably, 20% to 40% by weight is added to the blend.
  • Carbohydrates such as polydextrose and palatinit as well as mono-, di- and tri-calcium phosphate may also * optionally serve as suitable inert protective materials.
  • the wet granulated APM granules may then be coated with a fat such as animal fat, vegetable fat, waxes, cellulose, or mixtures thereof. This is readily achievable despite the non-uniformity of the particle size shape.
  • the particles are coated with a mixture of partially hydrogenated soybean oil and glycerol monostearate.
  • the soybean oil may consist of from about 60% to about 99% and most preferably of from about 90% to about 98% by weight of the entire coating composition
  • the glycerol monostearate may be incorporated in amounts of from about 0.5% to about 80% and preferably of from about 0.5% to about 20%.
  • the coating process may be carried out using a standard fluidized bed coating apparatus such as the Verse Glatt Fluid Bed Agglomerator/Dryer Model GPCG-1 (Glatt Air Techniques, Inc., Ramsey, N.J.).
  • the compressed APM particle cores are suspended in an air stream and sprayed with the molten fat composition that is passed through a compressed air nozzle as atomized particles and gradually coats the APM cores.
  • the amount of coating applied to the core is preferably no more than" a 1:1 APM core/fat ratio and may be applied as discrete layers during the fluidization process.
  • the encapsulated dipeptide sweetener may be used in many applications where " long shelf life is a consideration and conditions such as reactive flavor ingredients, temperature, moisture and pH of the food matrix present a hostile or degradative environment
  • the present inventions is particularly useful in the incorporation in chewing gum and most particularly, cinnamon chewing gums wherein aldehyde components of the flavor oil react with the dipeptide sweeteners causing diketopiperazine formation.
  • the APM granules of the present invention are also stable in the presence of high temperatures.
  • the absence of any peaks in the Differential Scanning Calorimetry (DSC) Profile is indicative of no phase changes occurring in the APM granules even when heated to 100°C.
  • the small peak in the DSC curve that appears near 60° is merely due to some melting of the fat coating caused by the increased temperatures.
  • the surprising and unexpected stability at these high temperatures make the granules of the present invention suitable for baking applications as well.
  • the amount of gum base will vary greatly depending on various factors such . as the type of base used, consistency desired and other components used to make the final product.
  • the gum base may be any water-insoluble gum base well known in the art.
  • suitable polymers in gum bases include both natural and synthetic elastomers and rubbers.
  • those polymers which are suitable l « in gum bases include, without limitation, substances of vegetable origin such as chicle, jelutong, gutta percha and crown gum.
  • Synthetic elastomers such as "butadiene-styrene copolymers, isobutylene-isoprene copolymers, polyethylene, polyisobutylene and 0 polyvinylacetate and mixtures thereof, are particularly useful.
  • the gum base composition may contain elastomer solvents to aid in softening the rubber component.
  • elastomer solvents may comprise methyl, glycerol or 5 pentaerythritol esters of rosins or modified rosins, such as hydrogenated, dimerized or polymerized rosins or mixtures thereof.
  • elastomer solvents suitable for use herein include the pentaerythritol ester of partially hydrogenated wood rosin, pentaerythritol 0 ester of wood rosin, glycerol ester of wood rosin, glycerol ester of partially dimerized rosin, glycerol ester of polymerized rosin, glycerol ester of tall oil rosin, glycerol ester of wood rosin and partially hydrogenated wood rosin and partially hydrogenated methyl 5 ester of rosin, such as polymers of alpha-pinene or beta-pinene; terpene resins including polyterpene and mixtures thereof.
  • the solvent may be employed in an amount ranging from about 10% to about 75% and preferably about 45% to about 70% by weight to the gum base.
  • a variety of traditional ingredients such as plasticizers or softeners such as lanolin, stearic acid, sodium stearate, potassium stearate, glyceryl triacetate, . glycerine, natural waxes and petroleum waxes such as polyurethane waxes, paraffin waxes and microcrystalline waxes may also be incorporated into the gum base to obtain a variety of desirable textures and consistency properties.
  • the chewing gum composition may additionally include the conventional additives of flavoring agents, coloring
  • ⁇ j agents such as titanium dioxide, emulsifiers such as lecithin and glyceryl monostearate; and additional fillers such as hydroxide, alumina, aluminum silicates, calcium carbonate, and talc and combinations thereof. These fillers may also be used in the gum base in various
  • the amount of fillers when used will vary from about 4% to about 30% by weight of the final chewing gum.
  • auxiliary sweeteners are utilized in addition to those in the present delivery 5 system
  • the present invention contemplates the inclusion of those sweeteners well known in the art, including both natural and artificial sweeteners.
  • additional sweeteners may be chosen from the following non-limiting list, sugars such as sucrose, glucose (corn syrup),
  • sugar alcohols such as sorbitol, sorbitol syrup, mannitol, xylitol, and the like.
  • additional sweetener is the nonfermentable sugar substitute (hydrogenated starch hydrolysate) which is described in U.S. Pat. No. Re. 26,959.
  • synthetic sweetener 3, 6-dihydro-6-methyl-l-l,2, 3-oxathiazin-4-one-2,2-dioxide, particularly the potassium (Acesulfame-K) , sodium and calcium salts thereof as described in German Patent No. 2,001,017.7. .
  • Suitable flavorings include both natural and artificial flavors, and mints such as peppermint, menthol, artificial vanilla, cinnamon, various fruit flavors, both individual and mixed, and the like are contemplated.
  • cinnamon is used and the - a flavorings are generally utilized in amounts that will vary depending upon the individual flavor, and may, for example, range in amounts of about 0.5% to about 3% by weight of the final chewing gum composition weight.
  • the colorants useful in the chewing gums of the 3 present invention include the pigments such as titanium dioxide and may be incorporated in amounts of up to about 1% by weight, preferably up to about 6% by weight.
  • the colorants may include other dyes suitable for food, drug and cosmetic applications, and known as F.D. & 0 C. dyes and the like.
  • the materials acceptable for the foregoing spectrum of use are preferably water-soluble.
  • Illustrative examples include indigo dye, known as F.D. & C. Blue No. 2, which is the disodium salt of 5.5'-indigotindisulfonic acid.
  • the chewing gums of the invention may be in any form 5 known in the art, such as stick gum, slab gum, chunk gum, shredded gum, hard coated gum, tabletted gum, as well as center-filled gum.
  • the process of preparing the inventive chewing gum compositions is as follows.
  • the gum base is melted (about 85° to about 90°C) , cooled to 78° C. and placed in a pre-warmed (60°C.) standard mixing kettle equipped with sigma blades.
  • the emulsifier is then added and mixed in.
  • a portion of the sorbitol and the glycerin is added and mixed in for an additional 3 to 6 minutes.
  • the mixing kettle is cooled and mannitol and the remainder of the sorbitol and glycerin are then added and mixing is continued.
  • the unflavored chewing gum temperature is about 39°-42° C.
  • Flavor oil is then added
  • the encapsulated dipeptide sweetener material is added and mixed for an additional 1 to 10 minutes.
  • the encapsulated dipeptide is added as the last ingredient.
  • the final gum temperature is about 39°C to
  • the chewing gum composition is then discharged from the kettle, rolled, scored and formed into chewing gum pieces.
  • APM particles possessing extended shelf life stability were made as follows. All percentages are based upon a 100% dry weight percent basis. Aspartame (28.3%), mannitol (17.0%), microcrystalline cellulose (17.0%), anhydrous dicalcium phosphate, (17.0%), and gum
  • 35 arabic (9.3%) was placed into a mixing bowl of a three speed mixer (Model C-100, Hobart Co., Troy, Ohio and mixed for 2 minutes at low speed. Additional gum arabic (11.4%) was separately dissolved in water to make a 40% gum arabic solution. The gum arabic solution was slowly blended into the sweetener powder mixture and an additional 277 grams of deionized water was added to the mixture to finish the wet granulation process. A wet granular mass was then formed. . The wet granular mass was dried in an oven (40-45°C) overnight.
  • the dried mass was milled in the Pennwalt Stokes Compacting equipment (Model 43-6; Warminister, Penna. ) and particles between 30-45 U.S. Standard mesh (590-350 « a micron) were collected and coated.
  • the particles were then coated using a Glatt GPCG-1 granulator/dryer on a 1:1 particle weight/coating weight ratio with partially hydrogenated soybean oil and glycerol monostearate mixture on a 1:1 particle
  • Stabilized aspartame particles were also made utilizing starch instead of mannitol together with gum 0 arabic as the inert binder material.
  • Citrus acid (0.24%) was added to the solution as buffer.
  • the gum arabic solution was mixed slowly into the sweetner powder mixture to form a wet granular mass which 0 was then dried in an oven (40-45°C) overnight.
  • the dried mass was milled in the Pennwalt Stokes
  • Standard mesh (590-350 microns) were collected, and coated with partially hydrogenated soybean oil and * glycerol monostearate mixture, using a Glatt GPCG-1
  • Stabilized aspartame particles were made as in Examples 1 and 2 with the exception that starch alone was used as the binder material.
  • Aspartame (26.92%), microcrystalline cellulose , (17.49%), dicalcium phosphate (17.49%), and starch were added in the bowl of a three speed mixer and blended for 2 minutes at low speed.
  • a starch solution was made by dissolving starch (18.88%) in 770 grams of deionized water. Both sodium citrate (.18%) and citric acid (.245)
  • Starch solution was then slowly added into the sweetener powder mixture to form a wet granular mass which was dried in an oven (40-45%°C) overnight. The dried mass was milled in the Pennwalt Stokes Compacting
  • Figure 2 shows gum sweetened with aspartame from examples 1-3 as compared with two standard compositions sweetened with aspartame not stabilized by the process of the present invention.
  • the aspartame granules made by the wet granulation process of the present invention show significantly greater stability than that of either of the two standard formulations. Even the formulation displaying the least amount of aspartame remaining
  • the milled granules are 0 easier to coat since a uniform layer is far easier to achieve with the compacted, denser crystals.
  • coatings must be able to wet and adhere to the crystalline surface which is not generally possible considering the needle-like tips and 5 other spike-like shape varations of pure aspartame powder.
  • the coatings in addition to being protective barriers, must be flexible enough to conform to the surface irregularities without cracking due to mechanical stresses which occur when the sweetener is incorporated into one of the numerous food applications, chewing gum in particular.
  • the dipeptide granule not only facilitates such coating but is self-stabilized to a degree as well.

Landscapes

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

Abstract

Composition édulcorante dipeptidique stabilisée à utiliser pour fabriquer du chewing-gum, qui donne une stabilité pendant une durée de conservation plus longue et un pouvoir édulcorant prolongé amélioré. Un édulcorant dipeptidique tel que l'aspartame est encapsulé à l'aide d'un procédé anhydre qui comprime les cristaux au sein d'un mélange d'ingrédients liants inertes de manière à former une plaque ou feuille solide qui est ensuite broyée pour obtenir des particules granulaires fines. Ces particules peuvent ensuite être recouvertes à l'aide d'un matériau hydrophobe, tel que de la graisse ou de la cire, puis incorporées dans divers produits alimentaires, tels que le chewing-gum. Ladite composition édulcorante est ainsi protégée de conditions néfastes de l'environnement telles qu'une température élevée, la moisissure et le pH.
PCT/US1992/004262 1991-07-08 1992-05-20 Composition edulcorante stabilisee WO1993000828A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72645991A 1991-07-08 1991-07-08
US726,459 1991-07-08

Publications (2)

Publication Number Publication Date
WO1993000828A2 true WO1993000828A2 (fr) 1993-01-21
WO1993000828A3 WO1993000828A3 (fr) 1993-03-18

Family

ID=24918686

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/004262 WO1993000828A2 (fr) 1991-07-08 1992-05-20 Composition edulcorante stabilisee

Country Status (2)

Country Link
MX (1) MX9203705A (fr)
WO (1) WO1993000828A2 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5397579A (en) * 1993-09-30 1995-03-14 Wm. Wrigley Jr. Company Environmentally stable chewing gum compositions containing erythritol
US5494685A (en) * 1994-05-17 1996-02-27 Wm. Wrigley Jr. Company Chewing gum with a rolling compound containing erythritol
US5536511A (en) * 1994-05-06 1996-07-16 Wm. Wrigley Jr. Company Chewing gum pellet coated with a hard coating containing erythritol and xylitol
US5545415A (en) * 1993-12-30 1996-08-13 Wm. Wrigley Jr. Company Low moisture chewing gum compositions containing erythritol
US5603970A (en) * 1994-05-06 1997-02-18 Wm. Wrigley Jr. Company Chewing gum pellet coated with a hard coating containing erythritol
WO1998052541A1 (fr) * 1997-05-20 1998-11-26 Warner-Lambert Company Comprimes a dissolution rapide et procede de fabrication par compression directe
US5916606A (en) * 1993-09-30 1999-06-29 Wm. Wrigley Jr. Company Chewing gum compositions containing erythritol and a moisture binding agent
US6264999B1 (en) * 1993-09-30 2001-07-24 Wm. Wrigley Jr. Company Chewing gum containing erythritol and method of making
US6864311B2 (en) 1997-03-25 2005-03-08 Rhodia Chimie Composition (e. g. ink or varnish) which can undergo cationic and/or radical polymerization and/or crosslinking by irradiation, based on an organic matrix, a silicone diluent and a photoinitiator
WO2005084446A1 (fr) * 2004-03-04 2005-09-15 Csm Nederland B.V. Granule contenant un ingredient fonctionnel pour les produits alimentaires et son procede de fabrication
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
WO2022216319A1 (fr) * 2021-04-06 2022-10-13 Altria Client Services Llc Granulés d'édulcorant encapsulés et leurs procédés de préparation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0053844A1 (fr) * 1980-12-10 1982-06-16 Ajinomoto Co., Inc. Composition édulcorante de dipeptide
EP0067595A2 (fr) * 1981-06-02 1982-12-22 Warner-Lambert Company Composition de gomme à mâcher contenant l'ester méthylique enrobé de la L-aspartyl-L-phénylalanine
EP0273857A2 (fr) * 1986-12-23 1988-07-06 Warner-Lambert Company Composition pour gomme à mâcher stable parfumée à la cannelle
EP0411326A2 (fr) * 1989-06-30 1991-02-06 Bio-Dar Ltd. Additifs alimentaires comprenant des microcapsules et leur usage
EP0458750A1 (fr) * 1990-05-25 1991-11-27 Warner-Lambert Company Composition À©dulcorante stabilisée

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0053844A1 (fr) * 1980-12-10 1982-06-16 Ajinomoto Co., Inc. Composition édulcorante de dipeptide
EP0067595A2 (fr) * 1981-06-02 1982-12-22 Warner-Lambert Company Composition de gomme à mâcher contenant l'ester méthylique enrobé de la L-aspartyl-L-phénylalanine
EP0273857A2 (fr) * 1986-12-23 1988-07-06 Warner-Lambert Company Composition pour gomme à mâcher stable parfumée à la cannelle
EP0411326A2 (fr) * 1989-06-30 1991-02-06 Bio-Dar Ltd. Additifs alimentaires comprenant des microcapsules et leur usage
EP0458750A1 (fr) * 1990-05-25 1991-11-27 Warner-Lambert Company Composition À©dulcorante stabilisée

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5397579A (en) * 1993-09-30 1995-03-14 Wm. Wrigley Jr. Company Environmentally stable chewing gum compositions containing erythritol
US6264999B1 (en) * 1993-09-30 2001-07-24 Wm. Wrigley Jr. Company Chewing gum containing erythritol and method of making
US5916606A (en) * 1993-09-30 1999-06-29 Wm. Wrigley Jr. Company Chewing gum compositions containing erythritol and a moisture binding agent
US5545415A (en) * 1993-12-30 1996-08-13 Wm. Wrigley Jr. Company Low moisture chewing gum compositions containing erythritol
US5603970A (en) * 1994-05-06 1997-02-18 Wm. Wrigley Jr. Company Chewing gum pellet coated with a hard coating containing erythritol
US5536511A (en) * 1994-05-06 1996-07-16 Wm. Wrigley Jr. Company Chewing gum pellet coated with a hard coating containing erythritol and xylitol
US5494685A (en) * 1994-05-17 1996-02-27 Wm. Wrigley Jr. Company Chewing gum with a rolling compound containing erythritol
US6864311B2 (en) 1997-03-25 2005-03-08 Rhodia Chimie Composition (e. g. ink or varnish) which can undergo cationic and/or radical polymerization and/or crosslinking by irradiation, based on an organic matrix, a silicone diluent and a photoinitiator
WO1998052541A1 (fr) * 1997-05-20 1998-11-26 Warner-Lambert Company Comprimes a dissolution rapide et procede de fabrication par compression directe
US5939091A (en) * 1997-05-20 1999-08-17 Warner Lambert Company Method for making fast-melt tablets
WO2005084446A1 (fr) * 2004-03-04 2005-09-15 Csm Nederland B.V. Granule contenant un ingredient fonctionnel pour les produits alimentaires et son procede de fabrication
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
WO2022216319A1 (fr) * 2021-04-06 2022-10-13 Altria Client Services Llc Granulés d'édulcorant encapsulés et leurs procédés de préparation

Also Published As

Publication number Publication date
WO1993000828A3 (fr) 1993-03-18
MX9203705A (es) 1993-01-01

Similar Documents

Publication Publication Date Title
US5043169A (en) Stabilized Sweetner Composition
EP0434321B1 (fr) Système de libération d'édulcorant à encapsulation multiple et son procédé de fabrication
US4722845A (en) Stable cinnamon-flavored chewing gum composition
AU719781B2 (en) Chewing gum composition containing sodium glycinate
US4816265A (en) Sweetener delivery systems containing polyvinyl acetate
EP0446170B1 (fr) Système de libération d'acides alimentaires contenant un acétate de polyvinyle
EP0426428B1 (fr) Système de libération d'édulcorant-arôme encapsulé et sa fabrication
US4933190A (en) Multiple encapsulated sweetener delivery system
CA2002702C (fr) Systemes de dispensation d'acide alimentaire contenant de l'acetate de polyvinyle
AU610840B2 (en) Chewing gum composition with encapsulated sweetener having extended flavor release
EP0453397B1 (fr) Système de libération d'arômes à encapsulation multiple et procédé de fabrication
US4803082A (en) Flavor and sweetness enhancement delivery systems and method of preparation
KR100237733B1 (ko) 소수성 액체를 위한 수용성 전달 시스템
US6472000B1 (en) Method of controlling release of bitterness inhibitors in chewing gum and gum produced thereby
WO1993000828A2 (fr) Composition edulcorante stabilisee
US6080432A (en) Chewing gum composition containing sodium glycinate and method of making a chewing gum product therefrom
EP0401956A2 (fr) Système de distribution d'un édulcorant ayant un point de fusion élevé

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): BR CA JP

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU MC NL SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): BR CA JP

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU MC NL SE

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA