[go: up one dir, main page]

WO1992011084A1 - Microencapsulated sweeteners for use in baked goods - Google Patents

Microencapsulated sweeteners for use in baked goods Download PDF

Info

Publication number
WO1992011084A1
WO1992011084A1 PCT/US1991/009434 US9109434W WO9211084A1 WO 1992011084 A1 WO1992011084 A1 WO 1992011084A1 US 9109434 W US9109434 W US 9109434W WO 9211084 A1 WO9211084 A1 WO 9211084A1
Authority
WO
WIPO (PCT)
Prior art keywords
sweetener
capsules
making
aspartame
wax
Prior art date
Application number
PCT/US1991/009434
Other languages
English (en)
French (fr)
Inventor
Bruce K. Redding, Jr.
Brian Butcher
Walter S. Garrison
Arden E. Schmucker
Original Assignee
Redding Bruce K Jr
Brian Butcher
Garrison Walter S
Schmucker Arden E
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 Redding Bruce K Jr, Brian Butcher, Garrison Walter S, Schmucker Arden E filed Critical Redding Bruce K Jr
Publication of WO1992011084A1 publication Critical patent/WO1992011084A1/en

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening
    • B01J13/22—Coating
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening

Definitions

  • This invention relates to the use of encapsulation to provide stability of artificial and certain natural sweeteners in baked good applications such as cakes, pies, cookies and certain confectionery products including candies. More specifically, this invention relates to the encapsulation of Aspartame to provide for small capsules with Ph, temperature and moisture stability.
  • Aspartame is an artificial sweetener currently in use in "cold" food applications and short term heated applications. Examples of cold applications include soda, toothpaste, and snack foods processed at room temperature. Short term heated applications include coffee and tea beverages. Aspartame has not heretofore been effective in baked goods where a combination of Ph, high temperatures and moisture content may act to chemically degrade the Aspartame. Items such as cakes, cookies and pies which may be baked at elevated temperatures for several minutes to nearly an hour tend not to be good candidates for use by certain temperature, Ph, or moisture sensitive sweeteners including Aspartame. Several efforts have been attempted to produce a bake survivable
  • the capsule sizes produced were so large as to affect the distribution of the capsules throughout the batter. Large capsules do not distribute well, resulting in many areas of a cake or cookie which were void of sweetness or which were aesthetically undesirable due to a speckled appearance in the product.
  • the invention described herein is a means of avoiding these problems.
  • the current invention provides for smaller capsules, with little agglomeration, and with a more complete enclosure of the capsule shell, thereby preventing or reducing the number of cracks or fissures which have led to past problems.
  • Figure 1 depicts several microcapsuie constructions available to encapsulate sweeteners.
  • Figure 2 is a DSC thermographic spectrum of granulated Aspartame using a fat/wax binding material.
  • Figure 3 is a DSC thermographic spectrum of the encapsulated Aspartame using a natural polymer as the shell coating of the capsule.
  • Figure 4 depicts the decomposition products produced by Aspartame when subjected to the temperatures, Ph and moisture present during most baking operations.
  • Figure 5 is a graph illustrating the decomposition ranges of Aspartame at various Ph levels at a standard temperature.
  • Figure 6 depicts the use of fats or waxes in the encapsulation of Aspartame, illustrating the use of normal fat/wax coatings vs. a tempered fat/wax coating.
  • Figure 7 depicts a block diagram of the process used to temper fats and waxes as applied in the encapsulation of particulate sweeteners.
  • Figure 8 depicts a prior art method of encapsulation known as coacervation.
  • Food sweeteners which may be either natural, artificial or a combination of both natural and artificial materials, are coated with a substance which will enable the sweeteners to survive the effects of and the conditions present in various baked goods, and additionally to provide a means of reducing any aftertaste associated with the use of certain artificial sweeteners.
  • a partial list of natural sweeteners and artificial sweeteners are shown, respectively in Tables 2A and 2B.
  • Tsau describes the use of encapsulated Aspartame in the field of baked good applications. Tsau teaches coatings comprised of fat materials, and capsule sizes over 177 microns in diameter. It has been found that these capsules produce void spots in various baked goods including cakes, pies and cookies. "Void Spots" are defined as areas within the baked good which are not sweet, being either totally devoid of sweeteners, bland to the taste, or actually abhorrent to the taste.
  • Void spots may occur because the capsules are not completely formed, thereby offering little protection for the Aspartame leading to degradation of the core material during the baking process (Aspartame is known to be Ph, moisture and temperature sensitive, resulting in a breakdown of the Aspartame molecule into certain distasteful or bland decomposition by products, as described in Figure 4).
  • the void spots may also form because the capsules are too large thereby preventing adequate dispersion through the batter. Void spots result in poor distribution within the baked good leaving void spots in many sections which are then devoid of taste.
  • Table 5 illustrates the survivability of sweetness after baking chocolate cake with regular Aspartame sweetener when used in either raw or granulated form as compared to various samples of encapsulated Aspartame.
  • Table 1 shows the appearance of both raw and granulated Aspartame in cake in relation to encapsulated Aspartame samples of a smaller average size.
  • the raw Aspartame has an average particle size of just 29 microns, as shown in Table #6 while the granulated Aspartame has an average size over 650 microns.
  • the leaves specks in the baked good which are especially visible on the underside of cakes, pies and cupcakes as evidenced by the descriptions present in Table 1.
  • the void spots may occur because the large granulated sweetener may not completely release the sweetener during the baking process or immediately afterwards, thereby not allowing contact between the user and the sweetener's active material at the taste point. The taster then perceives no sweet taste in the baked good at all. Additionally, these large capsules provide a severe aftertaste problem for many users after the baking process.
  • Smaller capsules provide for greater dispersion in a homogeneous manner within the batter, resulting in cakes, cookies and pies with no visible sweetener specks, and with fewer or no void spots.
  • Aspartame capsule which is really a granulated
  • the present invention produces capsules with an average size as low as 4.0 microns.
  • Cakes, cookies and pies produced with these sweetener capsules exhibit no void spots at all and no visible specks in the final product after baking. Note the results indicated in the size comparison shown on Table #6, the sweetness taste test illustrated in Table 3 and the aesthetic appearance comparison in chocolate cake as shown in Table 1.
  • SCALE Least amount of aftertase (O) Most amount of aftertaste (10)
  • Results are based on a subjective blind taste test conducted using 20 persons.
  • the capsules of the prior art therefore, offer little protection against the degradation effects of Ph, moisture and temperature presented during the preparation of the dough or during the baking of various pies, cakes, cookies and other baked goods.
  • the fat/wax shell material is not an effective barrier due to the micropores and crevices in the structure as illustrated in Figure 6. While it has been discovered by applicants that an improved fat/wax material in all beta or nearly all beta crystalline form provides a more protective coating in the encapsulation of APM (Aspartame), other materials have also been observed to provide similar protective abilities. These other materials include natural polymers such as those listed in Table 4.
  • GLYCEROL TRISTEARIN GELATIN GLYCEROL TRISTEARIN GELATIN
  • the encapsulation of Aspartame using a fat/wax based coating is possible using a fat which has been forced into a more stable beta crystalline form by heat treatment methods employing either a thermal tempering of the fat while in a molten state or soon after it has solidified to help prevent the formation of lesions and micropores in the coated sweetener product. Additionally, fats and waxes may be melted into a molten liquid state which is then subjected to an abrupt pressure change before the molten fat or wax is applied as a shell to core sweetener particles in a granulation or hot melt encapsulation method.
  • FIG. 7 illustrates the procedure used to pressure treat the molten fat or wax and then apply the treated shell material to a sweetener core, such as Aspartame particles.
  • Figure 2 is a thermograph of a prior art product. It shows that the product (tested using a Dupont Model TA-2000 Differential Scanning Calorimeter) has a mixed melting point profile. This is caused by the instability in the fat material used as the coating on Aspartame.
  • Figure 3 illustrates the thermal profile of the coated Aspartame product of the present invention. Note the single higher melting point, which is characteristic of the Beta Crystalline form in the resolidified pressure treated fat. The material in Figure 3 has greater thermal stability than that of ordinary melted and granulated fat coatings.
  • Example 4 An example of the use of fats treated to solidify in the Beta crystalline form, in a hot melt coating method of forming capsules using a sweetener particle as a core is given in Example 4.
  • Sweeteners may also be encapsulated using traditional encapsulation methods employing natural polymer shell materials, listed in Table 4.
  • Figure 8 illustrates a conventional encapsulation process known as coacervation which may employ such natural polymers.
  • FIG. 1 shows several capsule constructions which may be employed in practicing the present invention which include Reservoir, Micro-Sponge, Multi-Shell and Capsules within Capsules.
  • Reservoir capsule 2 has a shell 4 and a case 6.
  • Micro-sponge capsule 8 has porus openings 10 in shell layers 12 which encompass core droplets on particles 14.
  • Encapsulated capsule 6 includes a Reservoir capsule 2 surrounded by a second case 18 which is in turn encompassed by an outer shell 20.
  • a multi-wall capsule 22 includes a Reservoir capsule 2 with additional shell layers 24.
  • step one a core material 26 and shell material 28 are mixed with a volatile organic solvent 30 to form a dispersion 32.
  • the second step of the process is to add the dispersion 32 to water with a dispersing agent 34 while stirring the agent.
  • the final step is to permit the solvent to evaporate as indicated by numeral 36 while the dispersion is being stirred at a fast speed 35 or a slow speed 37.
  • Microcapsules 38 or 40 made of core material 26 and shell material 28 are formed. Large capsules 38 or small capsules 40 are formed when stirring occurs at the slow speed 37, conversely stirring at a fast speed 35 produces smaller capsules 40.
  • the following examples illustrate the production of sweeteners using Aspartame as the target sweetener and employing natural polymers processed in a solvent, natural polymers processed in an aqueous media, a combination of two natural polymer shells and a tempered fat shell.
  • This example demonstrates a process for making encapsulated
  • Aspartame using a cellulosic material as a shell coating is apparent when considering the application of those capsules to baked goods, wherein the sugar would be replaced by a bulking agent which then would be used to maintain the integrity of the cake, cookie, pie or other baked good products.
  • Ethylcellulose is a version of Ethylcellulose or Methylcelloluse. Therefore, to provide compatibility between the Aspartame capsules and the bulking agent used to replace the sugar in cake it was decided to use Ethylcellulose as a coating material for Aspartame. This would then provide compatibility between the Ethylcellulose used as a bulking agent in particular cake formulations and the Ethylcellulose used in the Aspartame capsule.
  • the Aspartame capsules were produced, according to the following procedure: 20g of Ethocell ST 100 supplied by Dow Chemical Company, was dissolved in 600ml heated Cyclohexane, which was supplied by Aldrich Chemical Company. The Cyclohexane, had been previously heated to 70°C under mild agitation. The mixture of Ethocell and Cyclohexane was stirred until the mixture became clear. Within the Cyclohexane, the Ethocell has formed a film at this point. The mixture was cooled slightly to 60°C and 60g of Aspartame, which was supplied by Tosoh Canada Ltd., was added and the entire mixture was stirred for approximately 1 minute to allow for homogenization.
  • the apparatus known as the M-CAP #L50 device, using a size control Chamber #2 was employed to actually form the capsules.
  • This apparatus and method of forming capsules is described in United States Patent number 4,978,483.
  • the M-CAP apparatus applies an abrupt pressure change to a mixture of core material and shell material within a liquid dispersion, to form capsules.
  • the device was set for 75 PSI inlet pressure and the mixture of Ethylcellulose, Aspartame and Cyclohexane was processed through the device at a temperature of 60°C for one pass through the device. Capsules were observed to be formed immediately upon exiting the machine and were then later vacuum filtered from the Cyclohexane solvent and dried overnight in a fume exhaust hood.
  • the resulting product consisted of 73.4g of encapsulated product, with a yield of 92%, containing mostly spherical capsules with an average particle size as indicated in Table #6. This sample was known as AES-B-40. TABLE #6
  • Ethocell coated Aspartame capsules were then applied to cake and cookie formulations, according to cake recipes #1 and #2 and cookie recipes #3 and #4.
  • the results of this baking test indicated that the capsules were well formed and provided for a good dispersion within the cake mix with no void spots, locations which were not sweet, and the cake had no speckles. See Tables #1 and #3.
  • Table #5 indicated the survivability of these capsules after the baking trial.
  • Table #6 shows the average size range of capsules produced according to this method. 08/28/89
  • PROCEDURE Preheat oven to 350°F, grease and flour one 9x1 " x 1/2" round pan. Sift encapsulated sweetener and bulking agent together. Then sift all remaining dry ingredients thoroughly. In a separate bowl, blend milk, egg, shortening and vanilla. Slowly add dry ingredient to the liquid. Using a Deluxe Mixmaster blender, by Sunbeam, blend all ingredients together using medium speed, setting #2 for 3 minutes, scraping side of bowl to insure complete mixing. Remove mixing bowl from mixer and scrape excess batter off mixing blades and add to mixing bowl. Pour into prepared pan. Bake for 20-30 minutes in a 350°F oven or until wood tooth pick inserted in center comes out clean. Remove cake from over and cool in pan for 10 minutes. Remove from pan and let cool completely. 09/23/89
  • Sift encapsulated sweetener and bulking agent together. Hand blend sweetening mixture with butter until smooth and creamed (approximately 2 minutes). Add vanilla and egg until well blended. Slowly add in flour until well blended, making sure all flour is mixed homogeneously throughout mixture. Place small chunks of mixture on an ungreased sheet pan and bake for 10 minutes or until cookies are brown around the edges. Remove cookies from sheet pan and let cool.
  • Example #1 using a cellulose material as a shell, provided an encapsulated Aspartame which survived the baking process of cakes and cookies, with adequate sweetness throughout, even though only a small quantity of the encapsulated product was used.
  • Starch Company was used as the shell of a sweetener capsule and
  • Aspartame was used as the core sweetener.
  • the capsule mix is made in an aqueous media according to the following procedure: 100 grams of Capsul starch material is placed in a glass beaker containing 4 liters of distilled water which has been preheated to 75°C with rapid stirring, until the starch dissolved into a clear solution. The solution was allowed to cool to approximately 50°C until a slight haze formed. 260g of Aspartame supplied by Tosoh Canada Ltd. was added to the solution over a 15 to 20 minute period of time while still agitating the mixture.
  • the combined starch-water Aspartame mixture was then passed through the M-CAP device which is the #L50 model, using chamber #2, at 75 PSI, 2 strokes/sec, producing small capsules the size of which is indicated as sample number AES-B-39 in Table #6.
  • the capsules slurry was stirred until the sample reached ambient temperature and was then spray dried Bowen 7 foot spray dryer.
  • the inlet temperature was 290°C
  • the outlet temperature was 90°C at 8 PSI and 160 ml per hour rate.
  • the fuel rate to the spray dryer was set at a slow rate to avoid burning the starch shell.
  • the resulting sweetener capsules were mostly spherical with a yield of 60.8%.
  • the capsules were applied to cake and cookie recipes number 1 through 4 inclusive, and the cake was examined for speckles, sweetness or void spots, and survivability of the Aspartame component after baking. The results are evident in Tables #1 , #3 and #5 respectively.
  • a sweetener capsule composed of both natural polymer shells in a single wall matrix.
  • 30g of Gum Arabic and 30g of Ethylcellulose 41 1 also known as Bermocell E411 FQ, were blended together and then added to 3,640 ml of distilled water at an ambient temperature in a 4 liter glass beaker under mild agitation.
  • the mixture was then heated to a temperature of 50°C while stirring over a period of 30 minutes until the solution became clear.
  • the resultant sweetener capsules were well formed with an average size as indicated in material sample AES-B-36 in Table #6.
  • the Sweetener capsule mixture was then spray dried using a Bowen 7 foot spray drier, to obtain free flowing discrete sweetener capsule solids.
  • the total yield was 172 grams or 53.75%.
  • sweetener capsules proved superior in resistance to moisture, temperature and Ph degradation during baking, and when applied to cakes and cookies produced a superior baked product.
  • the use of multiple materials in a single matrix shell composition provides strength to the capsule and greater protection than is possible in some cases where a thin single wall material is employed.
  • the fat must first be tempered into a more stable polymorphic crystalline form. This can be accomplished by thermal or pressure tempering treatments. The result of such tempering treatments is indicated in Figure 6B, where a capsule 2 is shown with a shell 4 with fewer or no cracks or crevices or micropores.
  • a giycerol tristearin fat in wax form known as Dynasan 118, supplied by Huls of America, with a melting point of 70°C was chosen because of its significantly high melting temperature, offering the potential to be a superior thermal barrier for the targeted sweetener during the baking process. Additionally, it was chosen because of its high purity and crystalline structure.
  • the Beta Processor applies an abrupt pressure change to a molten fat or wax for the purpose of tempering the fat or wax upon cooling into a resolidified form.
  • the Beta Processor unit was set at 75 PSI inlet pressure at 1 stroke/sec while the molten Dynasan 1 18 was passing through the apparatus.
  • the pressure treated fat/wax was collected and was then applied while still in a molten state to 75 grams of Aspartame, supplied by Tosoh Canada Ltd., in a mixing bowl of an orbital mixer supplied by Hobart Company. The mix was agitated until the temperature cooled in the Dynasan
  • the resulting white solid product had a yield of 98%. There were no solvents used in this process. This sample is identified as AES-B-43.1 in Table #6, the size scan comparison.
  • the sweetener capsules made in the above Example 4 proved superior in resistance to moisture, temperature and Ph degradation during baking, and when applied to cakes and cookies produced superior baked goods.
  • the DSC spectra evident in Figure 3 is superior to the DSC spectra illustrated in Figure 2 which is Aspartame coated with a simple, untempered fat formulation obtained from Nutrasweet Company. Note the higher melting point and more stable crystalline structure of the Beta crystalline form fat/wax of Figure 3 compared to the instability and lower melting point of the fat DSC spectra of Figure 2.
  • the untempered fat illustrated in Figure 2 has a less defined melting point and, under microscopic examination, is found to contain several micropores, cracks and crevices, as shown in Figure 6A, thereby having reduced resistance to moisture penetration.
  • the decomposition products include Phenylalanine, Diketopiperazine Aspartic Acid and Aspartylphenylalanine.
  • the pressure treated fat which results in the Beta crystalline form have far fewer cracks or micropores, as may be observed through the illustration provided in Figure 6B, thereby resisting moisture penetration and the Ph difficulties accompanying moisture penetration. Additionally, tempered fat shell has a higher more stable melting point enabling resistance to heat during the baking stage, as seen in Figure 3. Because a fat is used as the shell, the fat tends to immediately release the sweetener upon contact in the mouth. This enables the sweetness to be sensed instantly upon the first bite of the baked goods incorporating the sweetener capsules.
  • the customer when using an encapsulated sweetener in a baked good, the customer expects instant gratification upon the first taste of the baked product. If the capsule protects the sweetener from the degradating effects of dough preparation or baking, but does not allow instant sensing of sweetness upon the first taste by a customer, the encapsulation effort is wasted. Most Reservoir type capsules, as shown in Figure 1 , would never release the sweetener if they were designed to be totally secure enclosures, until the capsules were actually digested. To provide an instant gratification to the customer, the capsules should ideally provide protection of the sweetener core throughout the dough preparation and baking stages, but allow release of the sweetener at the very end of the baking cycle.
  • the capsule has released, or has had at least a partial dissolution of the capsule shell leaving the sweetener core exposed, at the end of the baking cycle, so that there is an immediate sweet taste sensation upon first bite.
  • the particular coating materials listed in Table #4 were selected because they would offer protection during the baking stage but would partially release toward the end of the baking cycle, enabling instant sweet gratification upon first bite.
  • Table #3A shows the perceptions of a test audience composed of 20 persons when taste testing various cake and cookie formulations.
  • a comparison was made of cakes made with no Aspartame, raw Aspartame, Granulated Aspartame and each of the examples of encapsulated Aspartame listed herein. Note that in each case the encapsulated Aspartame was superior.
  • Table #3B indicates that during the taste test the baked goods tested had little or not aftertaste when the encapsulated Aspartame was used, and a severe aftertaste when the raw or the granulated Aspartame was used.
  • Various bulking agents may be used to replace the bulk when using high potent sweeteners in place of the normal sugar bulk.
  • Aspartame which is nearly 200 times sweeter than sugar
  • only 1 to 2 grams of Aspartame active material may be applied to a conventional cake formation, which would normally contain as much as 100 to 200 grams of sugar.
  • the lost bulk approximately 198 grams by weight, must be replaced by using a bulking agent.
  • Most bulking agents are cellulosic compounds which, when used in large quantities as is required in the use of Aspartame, can offer laxative problems. Certain bulking agents do not offer laxative problems; one such bulking agent is a product known as Snowite Oat Fiber supplied by Canadian Harvest Company.
  • Bulking agents control body or viscosity, and provide smooth, stable textures which improve mouth feel. Most bulking agents are soluble in cold water, improve browning and provide low to moderate sweetness with no starch flavors. One of the biggest advantages in using bulking agents is caloric reduction; however, few bulking agents claim to reduce calories.
  • the Aspartame capsules of the present invention has shells of a fat or wax having at least two crystalline forms.
  • the capsules shells are formed so that they are in the Beta crystalline form, which forms a more homogenous shell which is more resistant to moisture, temperature and Ph degradation during baking.
  • the present invention treats the fat or wax by an abrupt pressure change to the molten fat or wax; this causes it to solidify into the Beta crystalline form as opposed to its normal Alpha crystalline form.
  • the shell material can be treated and then used to form capsules using a conventional method, as in Example 4 where a hot melt process was used.
  • Example 4 where a hot melt process was used.
  • the shell material is treated as the capsules are formed using the M-CAP method referred to above.
  • the encapsulated sweeteners of the present invention offer improved survival during baking, thus permitting the use of non-sugar sweeteners in baked goods, such as cakes and cookies.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)
  • Confectionery (AREA)
PCT/US1991/009434 1990-12-17 1991-12-17 Microencapsulated sweeteners for use in baked goods WO1992011084A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62972190A 1990-12-17 1990-12-17
US629,721 1990-12-17

Publications (1)

Publication Number Publication Date
WO1992011084A1 true WO1992011084A1 (en) 1992-07-09

Family

ID=24524206

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/009434 WO1992011084A1 (en) 1990-12-17 1991-12-17 Microencapsulated sweeteners for use in baked goods

Country Status (5)

Country Link
CN (1) CN1066765A (zh)
AU (1) AU1241192A (zh)
IL (1) IL100398A0 (zh)
MX (1) MX9102619A (zh)
WO (1) WO1992011084A1 (zh)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5607697A (en) * 1995-06-07 1997-03-04 Cima Labs, Incorporated Taste masking microparticles for oral dosage forms
WO2000016643A1 (de) * 1998-09-18 2000-03-30 Haarmann & Reimer Gmbh Eingekapselte riechstoffe und/oder aromen mit speziellem freisetzungsverhalten
EP1133929A1 (de) * 2000-03-13 2001-09-19 Haarmann & Reimer Gmbh Eingekapselte Substanzen mit kontrollierter Freisetzung
WO2002000033A1 (en) * 2000-06-30 2002-01-03 Societe Des Produits Nestle S.A. Confectionery product containing active ingredients
JP2004532106A (ja) * 2001-02-12 2004-10-21 ドーバー ケミカル コーポレイション 制御された放出添加剤組成物
EP1210880A4 (en) * 1998-10-28 2005-03-11 San Ei Gen Ffi Inc COMPOSITIONS CONTAINING SUCRALOSE AND USE THEREOF
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
US8383154B2 (en) 2004-05-11 2013-02-26 Egalet A/S Swellable dosage form comprising gellan gum
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
RU2609226C1 (ru) * 2015-06-02 2017-01-31 Ольга Павловна Неклеса Дрожжевое тесто, сдоба, способ его получения и дрожжевое изделие из него
RU2609225C1 (ru) * 2015-06-02 2017-01-31 Ольга Павловна Неклеса Сдоба к дрожжевому тесту, способ получения дрожжевого теста и полученные из него дрожжевые изделия
WO2017136259A1 (en) * 2016-02-01 2017-08-10 Hello Delicious Brands Llc Fermented pizza dough snacks

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9445613B2 (en) * 2009-03-26 2016-09-20 Advanced Bionutrition Corporation Microencapsulation of bioactive substances and methods of making the same
CN108112954B (zh) * 2017-12-14 2021-07-02 广州市恒裕香料有限公司 一种微胶囊食品甜味剂及其制备方法

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3962468A (en) * 1974-03-07 1976-06-08 General Foods Corporation Spray-dried L-aspartic acid derivatives
US4122195A (en) * 1977-01-24 1978-10-24 General Foods Corporation Fixation of APM in chewing gum
US4230687A (en) * 1978-05-30 1980-10-28 Griffith Laboratories U.S.A., Inc. Encapsulation of active agents as microdispersions in homogeneous natural polymeric matrices
US4384004A (en) * 1981-06-02 1983-05-17 Warner-Lambert Company Encapsulated APM and method of preparation
US4465694A (en) * 1980-12-10 1984-08-14 Ajinomoto Company, Incorporated Dipeptide sweetening composition
US4515769A (en) * 1981-12-01 1985-05-07 Borden, Inc. Encapsulated flavorant material, method for its preparation, and food and other compositions incorporating same
US4704288A (en) * 1984-07-25 1987-11-03 Tsau Josef H Heat stabilized sweetener composition containing APM
US4740376A (en) * 1986-01-07 1988-04-26 Warner-Lambert Company Encapsulation composition for use with chewing gum and edible products
US4804548A (en) * 1984-10-05 1989-02-14 Warner-Lambert Company Novel sweetener delivery systems
US4824681A (en) * 1986-12-19 1989-04-25 Warner-Lambert Company Encapsulated sweetener composition for use with chewing gum and edible products
US4933190A (en) * 1986-12-23 1990-06-12 Warner-Lambert Co. Multiple encapsulated sweetener delivery system
US4978483A (en) * 1987-09-28 1990-12-18 Redding Bruce K Apparatus and method for making microcapsules
US4997659A (en) * 1989-03-28 1991-03-05 The Wm. Wrigley Jr. Company Alitame stability in chewing gum by encapsulation

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3962468A (en) * 1974-03-07 1976-06-08 General Foods Corporation Spray-dried L-aspartic acid derivatives
US4122195A (en) * 1977-01-24 1978-10-24 General Foods Corporation Fixation of APM in chewing gum
US4230687A (en) * 1978-05-30 1980-10-28 Griffith Laboratories U.S.A., Inc. Encapsulation of active agents as microdispersions in homogeneous natural polymeric matrices
US4465694A (en) * 1980-12-10 1984-08-14 Ajinomoto Company, Incorporated Dipeptide sweetening composition
US4384004B1 (zh) * 1981-06-02 1993-06-22 Warner Lambert Co
US4384004A (en) * 1981-06-02 1983-05-17 Warner-Lambert Company Encapsulated APM and method of preparation
US4515769A (en) * 1981-12-01 1985-05-07 Borden, Inc. Encapsulated flavorant material, method for its preparation, and food and other compositions incorporating same
US4704288A (en) * 1984-07-25 1987-11-03 Tsau Josef H Heat stabilized sweetener composition containing APM
US4804548A (en) * 1984-10-05 1989-02-14 Warner-Lambert Company Novel sweetener delivery systems
US4740376A (en) * 1986-01-07 1988-04-26 Warner-Lambert Company Encapsulation composition for use with chewing gum and edible products
US4824681A (en) * 1986-12-19 1989-04-25 Warner-Lambert Company Encapsulated sweetener composition for use with chewing gum and edible products
US4933190A (en) * 1986-12-23 1990-06-12 Warner-Lambert Co. Multiple encapsulated sweetener delivery system
US4978483A (en) * 1987-09-28 1990-12-18 Redding Bruce K Apparatus and method for making microcapsules
US4997659A (en) * 1989-03-28 1991-03-05 The Wm. Wrigley Jr. Company Alitame stability in chewing gum by encapsulation

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5607697A (en) * 1995-06-07 1997-03-04 Cima Labs, Incorporated Taste masking microparticles for oral dosage forms
WO2000016643A1 (de) * 1998-09-18 2000-03-30 Haarmann & Reimer Gmbh Eingekapselte riechstoffe und/oder aromen mit speziellem freisetzungsverhalten
US7229658B1 (en) 1998-10-28 2007-06-12 San-Ei Gen F.F.I., Inc Compositions containing sucralose and application thereof
EP1210880A4 (en) * 1998-10-28 2005-03-11 San Ei Gen Ffi Inc COMPOSITIONS CONTAINING SUCRALOSE AND USE THEREOF
EP1133929A1 (de) * 2000-03-13 2001-09-19 Haarmann & Reimer Gmbh Eingekapselte Substanzen mit kontrollierter Freisetzung
WO2002000033A1 (en) * 2000-06-30 2002-01-03 Societe Des Produits Nestle S.A. Confectionery product containing active ingredients
AU2001283838B2 (en) * 2000-06-30 2006-07-06 Societe Des Produits Nestle S.A. Confectionery product containing active ingredients
JP2004532106A (ja) * 2001-02-12 2004-10-21 ドーバー ケミカル コーポレイション 制御された放出添加剤組成物
EP1370351A4 (en) * 2001-02-12 2006-12-13 Dober Chemical Corp COMPOSITION OF CONTROLLED RELEASE ADDITIVES FOR COOLING CIRCUIT
US7524434B2 (en) 2001-02-12 2009-04-28 Dober Chemical Corporation Controlled release cooling additive composition
US8383154B2 (en) 2004-05-11 2013-02-26 Egalet A/S Swellable dosage form comprising gellan gum
US8383155B2 (en) 2004-05-11 2013-02-26 Egalet A/S Swellable dosage form comprising gellan gum
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
RU2609226C1 (ru) * 2015-06-02 2017-01-31 Ольга Павловна Неклеса Дрожжевое тесто, сдоба, способ его получения и дрожжевое изделие из него
RU2609225C1 (ru) * 2015-06-02 2017-01-31 Ольга Павловна Неклеса Сдоба к дрожжевому тесту, способ получения дрожжевого теста и полученные из него дрожжевые изделия
WO2017136259A1 (en) * 2016-02-01 2017-08-10 Hello Delicious Brands Llc Fermented pizza dough snacks

Also Published As

Publication number Publication date
IL100398A0 (en) 1992-09-06
CN1066765A (zh) 1992-12-09
MX9102619A (es) 1992-06-01
AU1241192A (en) 1992-07-22

Similar Documents

Publication Publication Date Title
DE69223024T2 (de) Essbare Folie
DE69300590T2 (de) Hitzestabile und aufbrechbare spruehtrocknete freifliessige geschmacksoelkapseln, verfahren zur herstellung derselben und ihre verwendung zu nahrungsmitteln.
CN101111164B (zh) 具有封装香料包衣的加热食品
WO1992011084A1 (en) Microencapsulated sweeteners for use in baked goods
NZ210051A (en) Insoluble dietary fibre from grain source coated with soluble dietary fibre
JP3213319B2 (ja) 水性液体香料油カプセル、その製造方法、及び食品への使用方法
JPS5953808B2 (ja) ソルビト−ルカプセル化されたフレ−バ−
CA2103524C (en) Method for imparting ability of preventing obesity and impaired glucose tolerance to foods and foods and sugar preparations exhibiting such preventive effects
JP2001521726A (ja) 低カロリー小麦粉代替品としての物理的にコーチングされたセルロース
CZ287471B6 (en) Chocolate chips with low content of fat and process for preparing thereof
EP1113725B1 (de) Eingekapselte riechstoffe und/oder aromen mit speziellem freisetzungsverhalten
EP1879470B1 (en) Fat, wax or oil-based food ingredient comprising encapsulated flavors
TW202011816A (zh) 烘烤甜食用改良劑
KR20210038545A (ko) 스펀지 케이크용 개량제
WO2020026997A1 (ja) 焼菓子の製造方法
US3737322A (en) Treatment of arabinogalactan
JPS6366490B2 (zh)
KR910009204B1 (ko) 디펩티드 감미제의 열안정도를 향상시키는 방법
DD141106A5 (de) Verfahren zur herstellung eines essbaren hefeproduktes
JP7421329B2 (ja) 小麦ふすま加工品
JP3164521B2 (ja) ウエハースシート及びその製造方法
JP5599255B2 (ja) カプセル化されたフレーバーを含んでなる脂肪、ろう又は脂をベースとする食品原材料
US20060286212A1 (en) Low moisture, low water activity caramel, caramel composite products and process for preparation
JP5073091B1 (ja) コーティング食品の製造方法
JP2800991B2 (ja) ケーキミックス

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR CA JP KR SU US

AL Designated countries for regional patents

Kind code of ref document: A1

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)

Free format text: US

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

Ref country code: CA