WO2013128121A1 - Maltodextrines hyperbranchees hypo-glycemiantes - Google Patents
Maltodextrines hyperbranchees hypo-glycemiantes Download PDFInfo
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- WO2013128121A1 WO2013128121A1 PCT/FR2013/050407 FR2013050407W WO2013128121A1 WO 2013128121 A1 WO2013128121 A1 WO 2013128121A1 FR 2013050407 W FR2013050407 W FR 2013050407W WO 2013128121 A1 WO2013128121 A1 WO 2013128121A1
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- maltodextrins
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- hyperbranched
- soluble
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 235000020985 whole grains Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
- C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
- C08B30/18—Dextrin, e.g. yellow canari, white dextrin, amylodextrin or maltodextrin; Methods of depolymerisation, e.g. by irradiation or mechanically
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
- A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
-
- 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
- C12P19/20—Preparation of compounds containing saccharide radicals produced by the action of an exo-1,4 alpha-glucosidase, e.g. dextrose
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the invention relates to new hyperbranched maltodextrins of low molecular weight, ie having an equivalent dextrose (DE) of between 8 and 15 and a molecular weight or W of between 1700 and 3000 daltons, characterized by their particular content of glucosidic bonds. 6, their soluble indigestible fiber content, and especially by their remarkable hypoglycemic properties.
- DE dextrose
- these new hyperbranched maltodextrins have a glucoside bond content 1 -> 6 of between 30 and 45%, a soluble indigestible fiber content of between 75 and 100% (according to the AOAC method No. 2001-03) and remarkable hypoglycemic properties, which they translate in vitro as in situ, by a protective effect vis-à-vis the digestion of standard maltodextrins.
- standard maltodextrins are defined as purified and concentrated mixtures of glucose and glucose polymers which are essentially ⁇ -1,4-linked with only 4 to 5% of glucosidic bonds (X-1,6). of various molecular weights, completely soluble in water and with low reducing power.
- maltodextrins are conventionally produced by acid or enzymatic hydrolysis of starch from cereals or tubers.
- the classification of standard maltodextrins relies mainly on the measurement of their reducing power, classically expressed by the concept of Dextrose Equivalent or DE
- DE Dextrose Equivalent
- the "protective effect" expressed by the hyperbranched maltodextrins of the invention with regard to the Standard maltodextrins results in their ability, when mixed with standard maltodextrins:
- hyperbranched maltodextrins of the invention slow down and therefore reduce the increase in blood glucose following a meal (postprandial), as well as the secretion of 'insulin.
- This action is likely to help diabetics improve the control of their blood sugar.
- compositions comprising such hyperbranched maltodextrins for use in many industrial applications, particularly in the food and pharmaceutical industries.
- the invention finally relates to a process for producing said hyperbranched maltodextrins.
- Dietary fiber is often classified according to its solubility, insoluble and soluble fiber.
- Insoluble fibers such as cellulose, resistant starches, corn (duff) or soybean fiber, have an essentially mechanical role in the gastrointestinal tract.
- Insoluble fiber helps prevent constipation by increasing stool weight and reducing intestinal transit time.
- Soluble fibers such as pectin and inulin, which are not digestible by human intestinal enzymes, are fermented by the intestinal bacterial flora. This fermentation releases short-chain fatty acids into the colon, which in turn reduces the pH of the colon and consequently limits the development of pathogenic bacteria and stimulates the development of beneficial bacteria.
- Short-chain fatty acids are also an important source of energy for colon cells and inhibit the growth and proliferation of cancer cells in the intestine.
- the targets of their functional effects are normally the colonic flora which ferments them and for which they serve as specific and selective substrates, the gastrointestinal physiology and in particular the functions ensured by the large intestine, the immune system, the bioavailability of minerals and the metabolism. lipids.
- the compounds classically classified in soluble fibers are fructooliqosaccharides and transqalacto-oliqosaccharides, but also lactulose, isomaltooliqosaccharides, oliqosaccharides extracted from soya, xylooliqosaccharides, etc.
- fructooliqosaccharides are polymers of short chain fructose units which are not hydrolysed in the gut in the human, but are degraded by the resident flora of the colon.
- FOS mainly induce the growth of lactobacilli and endoqene bifidobacteria of the gut in humans and animals.
- Polydextrose is for example synthesized by random polymerization of glucose in the presence of sorbitol and a suitable acid catalyst (such as citric acid) and at high temperature.
- a suitable acid catalyst such as citric acid
- Polydextrose is widely used in food as a feedstock and as a low calorific ingredient. Polydextrose is not dieterized or absorbed in the gut and a significant portion is found in the feces.
- the Applicant Company itself has also described in its patent application EP 1.006.128 "branched maltodextrins" having between 15 and 35% glucoside bonds 1-6, a reducing sugar content of less than 20%, a polymolecularity index. less than 5 and a number average molecular weight n at most equal to 4500 g / mol.
- branched maltodextrins are especially indigestible, which has the effect of reducing their caloric power, preventing their assimilation in the intestine. hail, and they thus constitute a source of indigestible fiber.
- fibers can be dosed according to different AOAC methods. Examples of such methods are AOAC 997.08 and 999.03 for fructans, FOS and inulin, AOAC 2000.11 for polydextrose, AOAC 2001.03 for the determination of fibers in branched maltodextrins or AOAC 2001.02 method for GOS as well as soluble oligosaccharides of oleaginous or proteinaceous origin.
- the hyperbranched maltodextrins according to the invention constitute a new family in the sense that it is very different from those of the state of the art, including the other low molecular weight branched maltodextrins which the applicant company has already proposed and described in its own prior patent applications.
- branched maltodextrins is meant within the meaning of the invention maltodextrins described in patent EP 1,006,128 which the applicant company holds.
- the hyperbranched maltodextrins of the invention have an equivalent dextrose (DE) of at least 8 to at most 15 and a molecular weight or w of at least 1700 to at most 3000 daltons.
- DE equivalent dextrose
- a soluble indigestible fiber content determined by the AOAC Method No. 2001-03, of not less than 75 and not more than 100%, and
- hypoglycemic capacity expressed according to an A test, resulting in:
- a first family of products in accordance with the invention consists of hyperbranched maltodextrins having a DE of between at least 8 and at most 12 and a w of between at least 2500 and at most 3000 daltons, characterized by:
- glucoside bond content of from 1 to 6 between at least 30 and at most 35%
- soluble indigestible fiber content determined according to AOAC Method No. 2001-03, between at least 75% and not more than 80%.
- a second family of products in accordance with the invention consists of hyperbranched maltodextrins having an ED of between at least 12 and at most 15 and a Mw of between at least 1700 and at most 2500 daltons, characterized by:
- a soluble indigestible fiber content determined according to AOAC Method No. 2001-03, between at least 80 and not more than 100%.
- the hyperbranched maltodextrins according to the invention are firstly characterized by their DE and by their molecular weight.
- the hyperbranched maltodextrins according to the invention by their DE and their molecular weight, are similar to this family of branched maltodextrins.
- the analytical parameters of DE and molecular weight (or w) are determined by any method otherwise known to those skilled in the art:
- the method for determining Dextrose Equivalent is, for example, the constant titration method of LANE-EYNON
- the Mw values are measured by size exclusion chromatography, based on the selective retention of the solute molecules according to their size, because of their penetration or not into the pores of the stationary phase.
- the hyperbranched maltodextrins of the invention thus have a DE limited to a value between 8 and 15, for a low molecular weight, between 1700 and 3000 daltons.
- hyperbranched maltodextrins according to the invention differ from the branched maltodextrins of EP 1.006.128, they exhibit:
- the determination of the glucoside bond content 1 -> 2, 1 -> 3, 1 -> 4 and 1 -> 6 is carried out according to the conventional methylation technique described in HAKOMORI, S. 1964, J. Biol. Chem, 55, 205.
- hypoglycemic properties they are determined by the implementation of an enzymatic test in vitro and in situ, to measure the capacity hyperbranched maltodextrins of the invention to reduce the digestion of standard maltodextrins.
- this test consists of measuring over time the amount of reducing sugars released by action of pork pancreatic ⁇ -amylase on standard maltodextrins in the presence of hyperbranched maltodextrins 1 of the invention.
- the measurements are also carried out on the control (digestion of GLUCIDEX® 6 alone with ⁇ -amylase) and the results of this in vitro test are expressed in% of ⁇ -amylase activity versus the control.
- the hyperbranched maltodextrins of the invention thus reduce by 80 to 90% the hydrolysis of GLUCIDEX® 6 by pancreatic ⁇ -amylase.
- test For its "in situ" component, the test consists of performing a continuous intestinal infusion in the rat, so as to calculate the percentage of hydrolysis of standard maltodextrins.
- the small intestine of an OFA rat of Sprague-Dawley origin is infused into the duodenum and ileum.
- a closed circuit, in which circulates a constant current is realized.
- the current is provided by a peristaltic pump.
- a solution of the product to be tested is injected into the circuit.
- PEG polyethylene glycol
- the hyperbranched maltodextrins of the invention thus are able to reduce from 30 to 45% hydrolysis of the 6 GLUCIDEX ® end of intestinal perfusion.
- the acidified starch thus dehydrated is treated in a thin-film type reactor at a temperature between 120 and 300 ° C, preferably between 150 and 200 ° C,
- the low molecular weight fraction thus obtained is treated with an amyloglucosidase, f. the solution thus obtained is treated on a chromatographic column so as to exclude the oligomers of degree of polymerization 1 and 2, g. the hyperbranched maltodextrins thus obtained are recovered.
- step a.to step d. Steps which lead to the preparation of the low molecular weight fraction, any methods accessible to those skilled in the art can be employed herein.
- step e The fifth step of the process (step e) according to the invention, which is optional, consists in treating the low molecular weight fraction thus obtained with an amyloglucosidase.
- This enzymatic treatment is intended to hydrolyze predominantly the linear structures of the product thus obtained (glucosidic linkage ⁇ 1 4) so as to optimize the content of indigestible glucosidic bonds.
- the sixth step of the process (step f) according to the invention consists in treating the solution thus obtained on a chromatographic column so as to exclude the oligomers of degree of polymerization 1 and 2.
- This step may be carried out by any means known to those skilled in the art, for example by chromatography on DIAION UBR 35 K resin in sodium form, sold by MITSUBISHI.
- a mass yield of 40% allows, as will be exemplified below, to limit the content of DPI + DP2 to a value ⁇ 6% dry, preferably ⁇ 0.5% dry.
- the last step of the process according to the invention finally consists in recovering the hyperbranched maltodextrins thus obtained.
- Wheat starch is acidified with hydrochloric acid at a rate of 19.6 meq H + / kg dry, then dried at a residual moisture of 4%.
- This raw material is then introduced into a BUSS PR type mixer 46 maintained at a temperature of 180 ° C, at a flow rate of 20 kg / h, with a residence time of 5 seconds.
- the reaction is rapidly stopped by spraying cold water at 15 ° C. After purification by filtration, decolorization on adsorbent resins and on cationic and anionic resins, the branched starch derivatives thus obtained are brought to a solids content of 50%.
- the product obtained is subjected to a PUROLITE C 145 macroporous strong resin cation chromatography in potassium form, of particle size 250-350 ⁇ m, configured in 6 trays of 200 liters, maintained at 75 ° C.
- the feed rates of the syrup of branched starch derivatives and of the elution water are fixed at 60 l / h and 400 l / h, at the first and third plateau, respectively.
- the choice of outlet rates of the second and fourth plateau conditions obtaining branched maltodextrin fractions of high molecular weight and low molecular weight.
- the flow rate at the output of the fourth plate is set at 140 l / h.
- the fraction of n equal to 400 g / mol is obtained with an adjustment of the chromatographic parameters setting the yield at 30% (the yield being understood here as the proportion of dry matter extracted from this fraction of high molecular weight with respect to the dry matter introduced into the chromatographic system).
- AOAC fiber content (% / sec) 70.4
- the DPI and DP2 molecules are excluded by passing this low molecular weight fraction on a UBR 35 K chromatography column in Na + form.
- the mass yield is estimated at 50%.
- the product thus obtained is demineralized on cationic resins (PUROLITE C150) and anionic (Amberlite IRA 910 from ROHM & HAAS), and then optionally atomized.
- the DPI and DP2 molecules are also excluded from the product (A) treated beforehand.
- NUTRIOSE FB10 NUTRIOSE FB10
- commercial products are also tested in controls.
- NUTRIOSE ® FB10 has the following characteristics: - FROM: 10
- polydextrose As for polydextrose (marketed under the brand name LITESSE ® ), it presents:
- the measurement of the inhibition of intestinal digestion performed according to the test described hereinabove, it is carried on the GLUCIDEX ® 6-10 g / 1, the product (B) to 10 g / 1 and the product ( C) tested at 10 g / l.
- Product (B) limits the hydrolysis of GLUCIDEX ® 6. At the end of intestinal infusion, the percentage hydrolysis of GLUCIDEX 6 is 63.9% compared to 98.0 obtained when GLUCIDEX ® 6 is tested alone.
- the product (C) limits the hydrolysis of GLUCIDEX ® 6.
- the hydrolysis of the pourcentaqe GLUCIDEX ® 6 is 56.9% compared to 100.5% obtained when the GLUCIDEX ® 6 is tested alone.
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020147023852A KR102080562B1 (ko) | 2012-02-28 | 2013-02-27 | 혈당강하 고분지형 말토덱스트린 |
EP13712862.5A EP2820050A1 (fr) | 2012-02-28 | 2013-02-27 | Maltodextrines hyperbranchees hypo-glycemiantes |
CA2865063A CA2865063C (fr) | 2012-02-28 | 2013-02-27 | Maltodextrines hyperbranchees hypo-glycemiantes |
JP2014559278A JP6291425B2 (ja) | 2012-02-28 | 2013-02-27 | 血糖降下性多分岐マルトデキストリン |
US14/379,362 US9783619B2 (en) | 2012-02-28 | 2013-02-27 | Hypoglycemic hyper-branched maltodextrins |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1251810A FR2987360B1 (fr) | 2012-02-28 | 2012-02-28 | Maltodextrines hyperbranchees hypo-glycemiantes |
FR1251810 | 2012-02-28 |
Publications (1)
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WO2013128121A1 true WO2013128121A1 (fr) | 2013-09-06 |
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ID=48014075
Family Applications (1)
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PCT/FR2013/050407 WO2013128121A1 (fr) | 2012-02-28 | 2013-02-27 | Maltodextrines hyperbranchees hypo-glycemiantes |
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Country | Link |
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US (1) | US9783619B2 (fr) |
EP (1) | EP2820050A1 (fr) |
JP (1) | JP6291425B2 (fr) |
KR (1) | KR102080562B1 (fr) |
CA (1) | CA2865063C (fr) |
FR (1) | FR2987360B1 (fr) |
WO (1) | WO2013128121A1 (fr) |
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FR3077959B1 (fr) | 2018-02-22 | 2021-09-24 | Roquette Freres | Procede de fabrication de dextrine de pois resistante |
US11540549B2 (en) | 2019-11-28 | 2023-01-03 | Tate & Lyle Solutions Usa Llc | High-fiber, low-sugar soluble dietary fibers, products including them and methods for using them |
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WO2024036206A1 (fr) * | 2022-08-12 | 2024-02-15 | Cargill, Incorporated | Polycondensation de sucres en présence d'eau à l'aide d'un microréacteur |
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FR3032709A1 (fr) * | 2015-02-16 | 2016-08-19 | Roquette Freres | Malto-oligo-saccharides riches en fibres et presentant une faible biosdisponibilite en glucose, leur procede de fabrication et leurs utilisations en nutrition humaine et animale |
WO2016132064A1 (fr) | 2015-02-16 | 2016-08-25 | Roquette Freres | Malto-oligo-saccharides riches en fibres et presentant une faible biosdisponibilite en glucose, leur procede de fabrication et leurs utilisations en nutrition humaine et animale |
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JP2018507856A (ja) * | 2015-02-16 | 2018-03-22 | ロケット フレールRoquette Freres | グルコースの生体利用効率が低い繊維を多く含むマルトオリゴ糖、その製造方法、食品および動物飼料におけるその使用 |
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CA2865063C (fr) | 2020-04-28 |
KR102080562B1 (ko) | 2020-02-24 |
JP2015510014A (ja) | 2015-04-02 |
JP6291425B2 (ja) | 2018-03-14 |
KR20140141580A (ko) | 2014-12-10 |
CA2865063A1 (fr) | 2013-09-06 |
US20150025037A1 (en) | 2015-01-22 |
US9783619B2 (en) | 2017-10-10 |
EP2820050A1 (fr) | 2015-01-07 |
FR2987360A1 (fr) | 2013-08-30 |
FR2987360B1 (fr) | 2014-03-28 |
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