WO2020240257A1 - Processus pour la production de microparticules et de nanoparticules porteuses d'édulcorants - Google Patents

Processus pour la production de microparticules et de nanoparticules porteuses d'édulcorants Download PDF

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Publication number
WO2020240257A1
WO2020240257A1 PCT/IB2019/054446 IB2019054446W WO2020240257A1 WO 2020240257 A1 WO2020240257 A1 WO 2020240257A1 IB 2019054446 W IB2019054446 W IB 2019054446W WO 2020240257 A1 WO2020240257 A1 WO 2020240257A1
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WO
WIPO (PCT)
Prior art keywords
high intensity
nanoparticles
production
continuous process
sweetener
Prior art date
Application number
PCT/IB2019/054446
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English (en)
Spanish (es)
Inventor
Fabio Rafael DUQUE CARDONA
Original Assignee
Biodynamic Process S.A.S.
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 Biodynamic Process S.A.S. filed Critical Biodynamic Process S.A.S.
Priority to PCT/IB2019/054446 priority Critical patent/WO2020240257A1/fr
Priority to CONC2019/0011579A priority patent/CO2019011579A2/es
Publication of WO2020240257A1 publication Critical patent/WO2020240257A1/fr

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G3/00—Glycosides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/64—Preparation of S-glycosides, e.g. lincomycin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y99/00—Subject matter not provided for in other groups of this subclass

Definitions

  • the present invention refers to a continuous process for the production of sweetener-bearing micro and nanoparticles, preferably steviol glycosides from Stevia rebaudiana Bertoni, which comprises formation of inclusion complexes based on cyclodextrins, followed by an encapsulation step with polysaccharides , an extrusion stage and finally, a stage of application of controlled temperatures, where the product obtained is a non-caloric sweetener composition, with clean and natural flavor, dissolution, dosage and diamond granulometry more similar to sugar and not hygroscopic.
  • alternative sweeteners have low solubility in water, some even give rise to solutions with high turbidity, which makes their use even more difficult in the production of low-calorie beverages and foods.
  • oligosaccharides such as cyclodextrins, which form inclusion complexes by trapping hydrophobic molecules inside their toroid nucleus.
  • the product reported in the application MX2015007522 is a whitish powder without any apparent granulometry, which is not assimilated to the shiny or diamond texture typical of sugar.
  • the use of gamma cyclodextrins, which are preferred according to the claims of this application, involves high costs and has the disadvantage of having been associated with the production of solutions with turbidity.
  • the Mexican application MX2012009166 discloses an inclusion complex comprising a substantially pure terpene glycoside and at least one cyclodextrin to increase the solubility of the inclusion complex.
  • this invention has the same problems of temporary improvement of the flavor, its granulometry that is not assimilated to the shiny and diamond texture of sugar, and when using the cyclodextrins range , whose price is high, production costs make the product industrially unprofitable.
  • the product that uses cyclodextrin range has the disadvantage of having been associated with the production of solutions with turbidity.
  • the spraying process in this case is carried out by lyophilization, which makes the process increase its costs and its profitability even less.
  • sweetener delivery systems for sweetener compositions comprising at least one high potency natural sweetener
  • the application MX2009012450 as well as the patent US 8,254,740 propose the production of a mass, preferably with sweeteners, binders and plasticizers, which is extruded through holes to produce small cylinders or pellets, which can be dried and crushed to generate compact particles with a certain granulometry, which will be difficult to dissolve due to their hard and smooth texture, which offers greater resistance to dissolution in aqueous medium, since it lacks spaces porous that allow the entry of liquid for rapid dissolution. Additionally, these blends do not reduce or eliminate the aftertaste of high intensity sweeteners. Its sole objective is to achieve the stability of the sweetener when it is subjected to high temperatures and to ensure the uniform dissolution and dispersion of the sweetener within products that require a high temperature in their process.
  • the present invention relates to a continuous process for the production of high intensity sweetener carrier micro- and nanoparticles comprising preparing an aqueous solution of sweetener and cyclodextrins or their derivatives for the formation of inclusion complexes.
  • a stage of addition of polysaccharides or their derivatives with mechanical stirring to encapsulate the inclusion complexes and free cyclodextrins present in the solution of the first stage, promoting that these free cyclodextrins form inclusion complexes with the polysaccharide molecules and generating a homogeneous and stable dough.
  • Said mass is subjected to an extrusion stage, forming thin films, stretching its molecular architecture and weakening hydrogen bonds, thereby increasing the solubility of the final product. These films are taken to a drying stage at controlled temperatures.
  • the dried films are cooled and subjected to a milling and sieving step to obtain a product with a shiny and diamond grain size more similar to sugar.
  • the method can include a second drying, after screening, to remove residual moisture and obtain the final product.
  • the product obtained by the method described above is part of the present invention, which is a non-caloric sweetener composition, with micro and nanoparticles carrying high intensity sweeteners that presents a clean and natural flavor, dissolution, dosage and granulometry non-hygroscopic diamond more similar to sugar.
  • the high intensity sweetener is a steviol glycoside from Stevia rebaudiana Bertoni, preferably rebaudioside A.
  • the present invention is related to a continuous process for the production of micro and nanoparticles carrying high intensity sweeteners that comprises the following steps:
  • step c) Extrude the mass from step b), forming thin films, stretching its molecular architecture and weakening hydrogen bonds, thereby increasing the solubility of the final product, and
  • step c) Dry the films of step c) by means of thermal processes.
  • the method of the invention additionally comprises the following steps: e) Cooling the dried films,
  • the method can include a step h) consisting of a second drying to remove residual moisture and obtain the final product.
  • the high intensity sweetener (with a sweetness intensity greater than sucrose), added in step a) is selected from the group consisting of artificial sweeteners such as sucralose, acesulfame potassium, aspartame, alitame, saccharin, neohesperidine dihydrochalcone, cyclamate, dulcin, neotame, N- [N- [3-hydroxy-4-methoxyphenyl) propyl] -L- a-aspartyl] -L-phenylalanine ester, 1-methyl ester -methyl of N- [N- [3- (3-hydroxy-4-methoxyphenyl) -3 methylbutyl] -La-aspartyl] -L-phenylalanine, 1-methyl ester of N- [N- [3- (3-methoxy-4-hydroxyphenyl) propyl] -L- a-aspartyl] -L- phenylalanine,
  • the sweetener is a steviol glycoside from Stevia rebaudiana Bertoni, and preferably, the sweetener is rebaudioside A.
  • the inclusion complex that is formed in step a) comprises a mixture of sweeteners.
  • the mixture preferably comprises two or more terpene glycosides derived from stevia, and in an even more preferred embodiment, the complex includes stevia extract or a combination comprising rebaudioside A.
  • the cyclodextrin also called cycloamylose
  • added in the solution of step a) of the method of the present invention refers to any cyclodextrin that increases the solubility of the sweetener.
  • said cyclodextrin is selected from the group consisting of a-cyclodextrin, b-cyclodextrin, and-cyclodextrin, derivatives thereof or a mixture thereof.
  • Non-limiting examples of such cyclodextrin derivatives include alkylated cyclodextrins, hydroxyalkylated cyclodextrins; ethylcarboxymethyl cyclodextrins; sulfonated and sulfoalkyl ether cyclodextrins; cyclodextrins substituted with ammonium groups, phosphate groups, and hydroxyl groups, and salts thereof; fluorinated cyclodextrins; and saccharide substituted cyclodextrins.
  • ⁇ -cyclodextrin Preferably ⁇ -cyclodextrin.
  • the solvent is water and the sweetener: water ratio is 1: 10, 1: 100, 1: 200, 1: 300, 1: 400, 1: 500, 1: 600, 1: 700 , 1: 800, 1: 900, 1: 1000, preferably 1: 100 to 1: 500, and the ratio of sweetener: cyclodextrin added in step a) is 1: 1, 1: 10, 1: 20, 1 : 30, 1: 40, 1:50, 1:60, 1:70, 1:80, 1:90, 1: 100, 1: 1000, preferably 1:10 to 1:30.
  • the preferable polysaccharide is maltodextrin and said polysaccharide is added in a ratio of 1: 1, 1: 25, 1: 50, 1: 75, 1: 100, 1: 125, 1: 150 , 1: 175, 1: 200 with respect to the solution of step a).
  • the polysaccharide: solution ratio is in the range of 1: 50 to 1: 100.
  • the homogeneous mass composed of sweetener, cyclodextrins and maltodextrins, is extruded during step c) to form lamellae of 0.5 mm to 5 mm.
  • the extruder used is a piston extruder, which passes the mass through small nozzles, at pressures sufficient to stretch the molecular structure, weakening the hydrogen bonds and thus increasing the solubility of the final product.
  • the films are subjected to thermal processes for drying and crystallization.
  • Said term processes can be conventional processes, including ovens, whether electric or gas, fluidized bed dryer, hot air, infrared rays, microwaves, among others.
  • microwave appliances Preferably microwave appliances.
  • the temperatures at which said processes are carried out are in the range of 1 ° C to 200 ° C, preferably 150 ° to 200 ° C.
  • the process comprises a stage of cooling the dried films in stage d), followed by a stage of milling with a roller mill, which allows obtaining nano and microparticles and agglomeration of them, and a stage of screening the ground product, using sieves of 150 microns to 1,350 microns, preferably from 500 to 650 microns, to obtain a product with shiny and diamond granulometry with a clean and natural flavor more similar to sugar .
  • the method can include a step h) consisting of a second drying to remove residual moisture and obtain the final product.
  • this drying is carried out in infrared rotary kilns, where the temperature is from 60 ° C to 80 ° C.
  • composition with high intensity sweetener carrier micro and nanoparticles obtained by the method described above is part of the present invention, which is a non-caloric sweetener composition, with a clean and natural flavor, dissolution, dosage and granulometry non-hygroscopic diamond more similar to sugar.
  • clean taste implies the elimination of undesirable flavors such as delayed onset of sweetness, prolonged sweet aftertaste, back taste, metallic taste, bitter taste, taste with a refreshing sensation, or menthol-like taste, flavor similar to liquor or liquorice, and / or the like.
  • the process and the granulometry of the present invention allow the sweetness of one teaspoon of the composition with nano and microparticles of sweetener to be equal to the sweetness of a teaspoon of sugar. However, its weight varies substantially, since a teaspoon of sugar is equal to 5 g (20 Kcal.), While a teaspoon of the composition with micro and nanoparticles carrying high intensity sweeteners of the present application is equal to 0, 9 gr (less than 5 Kcal.)
  • composition with high intensity sweetener carrier micro and nanoparticles resulting from the process described in this application can be considered calorie-free, since it has less than 5 calories and less than one carbohydrate per serving (one teaspoon dulcera), which meets the standards established by the United States Federal Drug Administration (FDA) to categorize them as calorie-free foods and additives.
  • FDA United States Federal Drug Administration
  • composition with micro and nanoparticles carrying high intensity sweeteners obtained by the method of the present invention can have a solubility at room temperature greater than 5%, greater than 10%, greater than 15%, or greater than 20% with respect to to the solubility exhibited by the initial sweetener.
  • the use of the composition with micro and nanoparticles carrying high intensity sweeteners obtained by the method of the present invention is part of the present invention to make products for human or animal consumption by ingestion.
  • the sweetener composition with micro- and nanoparticles bearing sweeteners of high intensity is added to the product in the form of powder, granules, packages, tablets, sachets, cubes, solids, syrup or liquids.
  • Another aspect of the invention includes products for human or animal consumption by ingestion that comprise the composition with micro and nanoparticles bearing high intensity sweeteners obtained by the method of the present invention.
  • the expression “products for human or animal consumption by ingestion” refers both to substances that are taken in the mouth and subsequently expelled from it, as well as to substances that are ingested and enter the digestive tract. , such as food, drinks or any other substance that is swallowed or introduced into the mouth. These products include but are not limited to beverages, foods, tobacco, nutraceuticals, oral hygiene / cosmetic products, medications, and the like.
  • Non-limiting examples of the products of the present invention include beverages selected from the group consisting of non-carbonated or carbonated beverages such as soft drinks or sodas, cola drinks, ginger ale, beer, cider, fruit flavored drinks, powdered drinks. and the like; fruit or vegetable juices, fruit juices, fruit drinks, drinks containing fruit juice, fruit flavored drinks, vegetable juices, juices containing vegetables, and mixed juices containing fruits and vegetables; sports drinks, energy drinks, pulps and similar drinks; drinks such as tea, coffee, cocoa, chocolate, black tea, green tea, oolong tea, among others.
  • non-carbonated or carbonated beverages such as soft drinks or sodas, cola drinks, ginger ale, beer, cider, fruit flavored drinks, powdered drinks. and the like
  • sports drinks, energy drinks, pulps and similar drinks such as tea, coffee, cocoa, chocolate,
  • the products of the present invention include dairy foods such as butter, milk cream, whipped cream, yogurt, drinks with lactic acid bacteria or the like, drinks that contain milk or its derivatives, among them, drinks that mix milk with coffee, tea or fruits, among others.
  • the food products of the invention cover bakery products without limitation; including sugary food products, breads, cakes, cookies, desserts, biscuits, jellies, bowls, puddings, creams, sauces, chocolate, chocolates, candied fruits and seeds, arequipe, white delicacy, cakes, chocolate cakes, cheese, chicken, meat and nuts, mus and the like.
  • Other products that are part of the present invention are those that are produced from wheat flour, starch flour, barley flour or corn flour, oats, cereals, expanded cereals, pasta and their derivatives.
  • Products that can be made by adding the composition of the present invention also include frozen foods, such as sorbets, desserts, ice creams, popsicles and the like; common sugary confectionery products such as chewing gum or chewing gum, candies, soft candies, hard candy, nougats, columbines, chocolates, jelly candies and the like; edible gels; jellies, jam and the like; spices; sauces including fruit flavored sauces, chocolate sauces, and the like; soy sauce, ketchup, mayonnaise, mustard sauces, and seasonings including flavorings, such as seasoning broths and the like; unprocessed meat products and processed, such as hams, sausages, sausages and the like; retorted food products, pickles in brine or vinegar, preserves, snacks such as fried foods or other products marketed in bags or packages.
  • frozen foods such as sorbets, desserts, ice creams, popsicles and the like
  • common sugary confectionery products such as chewing gum or
  • Products of the present invention also include processed agricultural products, concentrates, animal feed, livestock products, or seafood.
  • drugs or quasi-drugs for oral administration in their different forms of administration are included in the scope of the products of the present invention; nutraceutical products, oral care products such as mouth fresheners, gargling agents, mouthwash agents, toothpaste, whitening toothpaste, dentifrices, mouth sprays, teeth whitening agents and the like; Dietary supplements; cannabis-containing products, tobacco products including smokeless and smokeless tobacco products such as shaved tobacco, shredded or powdered tobacco, cigarettes, pipe and cigar tobacco, chewable.
  • the products of the present invention may comprise, in addition to the usual components of the product, at least one additional additive selected from the group consisting of flavoring ingredients, flavorings, vitamins, amino acids, acids fatty, oil, protein or protein hydrolyzates, minerals, organic acids, astringent compounds, surfactants, thickeners, emulsifiers, edible colorants, flavonoids, alcohols, polymers, other additives used in the food sector, and even sugar or other sweeteners.
  • at least one additional additive selected from the group consisting of flavoring ingredients, flavorings, vitamins, amino acids, acids fatty, oil, protein or protein hydrolyzates, minerals, organic acids, astringent compounds, surfactants, thickeners, emulsifiers, edible colorants, flavonoids, alcohols, polymers, other additives used in the food sector, and even sugar or other sweeteners.
  • Suitable flavoring and flavoring ingredient additives that may accompany the products of the present invention are selected, without being limited thereto, from the group consisting of vanillin, vanilla extract, mango extract, cinnamon, citrus fruit, coconut, ginger, viridiflorol, almond nuts, menthol (including menthol without mint), fruit extracts or artificial flavors, such as substances that simulate fruit, coffee, chocolate, nut flavors or provide an intense bitter or acid, among others.
  • the sweetener produced by the method of the present invention is a table-top sweetener composition comprising micro- and nanoparticles bearing high intensity sweeteners obtained by the method of the present invention.
  • the tabletop sweetener compositions can be in the form of powders, granules, packets, tablets, sachets, cubes, solids, or liquids.
  • the tabletop sweetener composition comprises a single serving package (portion control) comprising a volume of sweetener composition with high intensity sweetener carrier micro- and nanoparticles obtained by the method of the present invention equivalent to 5 grams of sugar, but its weight is equal to 0.9 grams.
  • a syrup to sweeten foods characterized in that it comprises the sweetening composition with micro and nanoparticles carrying high intensity sweeteners obtained by the method of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Wood Science & Technology (AREA)
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  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
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  • Medicinal Preparation (AREA)

Abstract

La présente invention se rapporte à un processus continu pour la production de microparticules et de nanoparticules porteuses d'édulcorants, de préférence des glucosides de stéviol de la stevia rebaudinana Bertoni, qui comprend la formation de complexes d'inclusion à base de cyclodextrines, suivie d'une étape d'encapsulation avec des polysaccharides, d'une étape d'extrusion et en dernier lieu, d'une étape d'application de températures contrôlées, le produit obtenu étant une composition édulcorante non calorique, à saveur nette et naturelle, dissolution, dosage et granulométrie du diamant très similaires à ceux du sucre et non hygroscopique.
PCT/IB2019/054446 2019-05-29 2019-05-29 Processus pour la production de microparticules et de nanoparticules porteuses d'édulcorants WO2020240257A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IB2019/054446 WO2020240257A1 (fr) 2019-05-29 2019-05-29 Processus pour la production de microparticules et de nanoparticules porteuses d'édulcorants
CONC2019/0011579A CO2019011579A2 (es) 2019-05-29 2019-10-18 Proceso para la producción de micro y nanopartículas portadoras de edulcorantes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2019/054446 WO2020240257A1 (fr) 2019-05-29 2019-05-29 Processus pour la production de microparticules et de nanoparticules porteuses d'édulcorants

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WO2020240257A1 true WO2020240257A1 (fr) 2020-12-03

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190021382A1 (en) * 2016-03-01 2019-01-24 Wm. Wrigley Jr. Company Long-lasting sweetener formulations

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190021382A1 (en) * 2016-03-01 2019-01-24 Wm. Wrigley Jr. Company Long-lasting sweetener formulations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHRANIOTIA CHARIKLEIA, SOFIA CHANIOTIA , AND CONSTANTINA TZIAA: "Microencapsulation of steviol glycosides (Stevia rebaudiana Bertoni) by a spray drying method . Evaluation of encapsulated products and prepared syrups", INTERNATIONAL JOURNAL OF FOOD STUDIES, vol. 4, 2015, pages 212 - 220, XP055764523, Retrieved from the Internet <URL:10.7455/ijfs/4.2.2015.a9> *
MICANQUER-CARLOSAMA ADRIANA , LILIANA SERNA-COCK ; ALFREDO AYALA-APONTE: "Double emulsion and complex coacervation in stevia encapsulation", VITAE 2017 UNIVERSIDAD DE ANTIOQUIA, vol. 24, no. 3, 2017, pages 167 - 177, XP055764530, ISSN: 0121-4004, DOI: 10.17533/udea.vitae.v24n3a02 *
WALSH JENNIFER ET AL.: "Playing hide and seek with poorly tasting paediatric medicines: Do not forget the excipients", ADVANCED DRUG DELIVERY REVIEWS, vol. 73, 12 March 2014 (2014-03-12), AMSTERDAM, NL, pages 14 - 33, XP028855087, ISSN: 0169-409X, DOI: 10.1016/j.addr. 2014.02.01 2 *

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