WO2001048024A1 - Complexes de cyclodextrine stabilises - Google Patents

Complexes de cyclodextrine stabilises Download PDF

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Publication number
WO2001048024A1
WO2001048024A1 PCT/IB2000/002060 IB0002060W WO0148024A1 WO 2001048024 A1 WO2001048024 A1 WO 2001048024A1 IB 0002060 W IB0002060 W IB 0002060W WO 0148024 A1 WO0148024 A1 WO 0148024A1
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WO
WIPO (PCT)
Prior art keywords
cyclodextrin
complex
emulsifying agent
water
guest
Prior art date
Application number
PCT/IB2000/002060
Other languages
English (en)
Inventor
Ansui Xu
Helena Qi
Wen Shieh
Original Assignee
Cerestar Holding B.V.
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 Cerestar Holding B.V. filed Critical Cerestar Holding B.V.
Priority to EP00991302A priority Critical patent/EP1155043A1/fr
Priority to JP2001548563A priority patent/JP2003518515A/ja
Publication of WO2001048024A1 publication Critical patent/WO2001048024A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
    • 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
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof

Definitions

  • This invention relates to a method for forming a cyclodextrin complex and, more specifically, a method for forming complexes of a cyclodextrin and a guest molecule which are smooth, stable, uniform and spherical.
  • Cyclodextrins also called “Schardingers dextrins", cycloamyloses, cyclomaltoses and cycloglucans, are oligomers of anhydroglucose, bonded together by alpha 1,4 bonds to form a ringed compound.
  • a six membered ring is called alpha cyclodextrin; seven, beta cyclodextrin; and eight, gamma cyclodextrin. These six, seven and eight membered rings are also referred to as cyclomaltohexaose, cyclomaltoheptaose and cyclomaltoctaose, respectively.
  • cyclodextrins are obtained by treating a starch slurry with enzyme or acid to produce a gelatinized and liquefied slurry having a DE between 1 and 5.
  • the gelatinized and liquefied starch slurry is then treated with cyclodextrin glycosyltransferase (CGT) , at the appropriate pH, temperature and time for the selected CGT.
  • CGT cyclodextrin glycosyltransferase
  • the enzyme, CGT is obtained from microorganisms such as Bacillus macerans, B. magaterium, B. circulans, B. stearothermohiilus, and Bacillus sp. (alkalophilic) as well as others.
  • the resulting digest from treatment of a gelatinized and liquefied starch slurry with CGT is then subjected to a separation and purification process to obtain cyclodextrins.
  • cyclodextrins are their ability to form complexes with other chemical compounds. Physically, a cyclodextrin is toriodal in shape. The interior of the cavity is hydrophobic while the exterior is somewhat hydrophilic. The consequence of this is that cyclodextrins are able to form inclusion complexes with substances that are less polar than water and have at least one outer geometric dimension corresponding to the diameter of the cyclodextrin cavity. Often the exterior of the cyclodextrin is modified to increase its hydrophilic nature. The cyclodextrin or modified cyclodextrin can be complexed with an insoluble or hydrophobic compound thereby forming a hydrophilic complex.
  • Cyclodextrin complexes are being employed in foods, pharmaceuticals, cosmetics, agricultural and chemical fields to act as a means for delivering a guest molecule.
  • the cyclodextrin is used not only to solubilize a guest but also to stabilize the guest or allow for slow release of the guest.
  • the guest is a flavor, a fragrance, a drug, an insecticide, or ' another key ingredient or component.
  • the most widely used method for forming a complex between a cyclodextrin and a guest molecule involves dissolving the cyclodextrin and guest molecule in water and collecting the precipitate that forms.
  • This precipitate is technically an agglomerate of a plurality of complexes.
  • One of the problems with such a process is that the recovered precipitate is rod-like in shape and increases in size over time such that different sized agglomerates are formed.
  • the different sized agglomerates yield uneven distribution of the complexes in the resulting composition. This uneven distribution can result in problems when the complex is used in a pharmaceutical application such as a drug.
  • these agglomerates also provide a grainy appearance and a gritty feel to the composition in which the complex is employed.
  • the gritty feel and grainy appearance of the complex are undesirable in both foods and cosmetics.
  • Dry or semi-dry methods have also been suggested for forming a complex of cyclodextrin and guest.
  • U.S. Patent Nos. 5,635,238; 5,580,851; 5,571,782; 5,552,378; and 5,543,157 teach a method for kneading cyclodextrin and a guest molecule to form complexes.
  • U.S. Patent No. 5,007,966 teaches a method for using a ball mill to form complexes between cyclodextrin and a guest molecule. Although these methods can produce a small particulate complex agglomerate, they do not necessarily provide a smooth, spherical uniform complex.
  • Beta cyclodextrin is currently the only cyclodextrin which is Generally Recognized As Safe (GRAS) for foods. It is also considered to be one of the most versatile of the cyclodextrins in its ability to complex with a variety of guest molecules.
  • GRAS Generally Recognized As Safe
  • the solution to the low solubility problem of beta cyclodextrin has been to chemically modify the cyclodextrin.
  • chemically modified beta cyclodextrin is not currently GRAS for food. Additionally, such modification can alter the complexation properties of the cyclodextrin and produce impurities which are difficult to separate from the product.
  • the resulting complex agglomerates take the form of small spherical particles which are smooth, stable and uniform in distribution.
  • the complexation process is conducted in water and the resulting cyclodextrin-guest complex agglomerates are encapsulated by the emulsifying agent.
  • emulsifying agent will be used throughout the specification and claims to refer to both an emulsifier and an emulsion stabilizer.
  • the process of the present invention entails combining water, cyclodextrin, a guest molecule and an emulsifying agent; and then mixing these components to form a uniform dispersion in water.
  • the particulate portion of the dispersion comprises the cyclodextrin complexed with the guest molecule with the emulsifying agent acting to stabilize the complexes.
  • a starch hydrolysate such as a corn syrup or a maltodextrin can be combined with the other components prior to mixing.
  • the starch hydrolysate forms part of the particulate of the dispersion.
  • the mixing must be vigorous enough to provide a uniform dispersion.
  • any order of adding and mixing can be employed, however, it is preferred to form the complex first by combining the water, guest molecule and cyclodextrin; mixing these components; and then adding the emulsifying agent and optional starch hydrolysate while continuing to mix.
  • the agglomerated complexes can be recovered by drying the mixture to provide a particulate material.
  • the starch hydrolysate is preferably employed when the resulting agglomerate is intended for use as a dried product or is intended to be dried and stored for a period of time.
  • the starch hydrolysate provides the dried particulate with protection against oxygen and deterioration of the guest molecule due to oxidation. Such protection is generally not necessary when the product is used in an aqueous medium.
  • All the components can be combined and then mixed or they can be combined and mixed a few at a time with the separate mixtures being combined and mixed to form the final dispersion.
  • water, cyclodextrin and a guest are combined and mixed in one step and the emulsifying agent with or without the starch hydrolysate is nixed with water in a separate step, then the two mixtures are combined F.nd mixed to form the uniform dispersion.
  • the mixing of the components must be such that a uniform dispersion is formed.
  • a homogenizer is used to form the mixture.
  • Suitable homogenizers include colloidal mills and high speed mixers/blenders.
  • the homogenizer is used in a conventional manner to form the dispersion.
  • a kneader device can be used provided a sufficient amount of water is present to allow the emulsifying agent to have an effect on the particle size and stability during the drying step.
  • the cyclodextrin and guest are combined and mixed in water for an extended period of time, for example, about two or more hours, to cause complexation to occur while the emulsifying agent, with or without the starch hydrolysate, is mixed in water also for an extended period of time, for example, about two or more hours, and then these two mixtures are mixed in a homogenizer to form the dispersion.
  • the cyclodextrin and guest are combined and mixed in water for a short period of time, for example, about ten minutes, to cause complexation to occur while the emulsifying agent, with or without the starch hydrolysate, is mixed in water also for a short period of time, for example, about ten minutes, and then these two mixtures are combined and mixed in a homogenizer to form the dispersion.
  • Complexation can, in some instances, take place fairly rapidly, however, it has been found that complexation is dependent upon the guest molecule and its interaction with cyclodextrin.
  • the combining and mixing steps are conducted at ambient temperature.
  • the mixing time is sufficient to cause complexation. As recognized, complexation can occur fairly rapidly. Mixing can be divided into two steps. One step to cause complexation and a second step to cause formation of a uniform dispersion/emulsion. Alternatively, mixing is conducted all at once to cause both complexation and formation of the uniform dispersion/emulsion. As brought out above, it is preferred that the mixing be in two steps, a first step to cause complexation and a second step with a homogenizer to form the uniform dispersion/emulsion. The first mixing step, to cause complexation, is done in a less vigorous manner than the second step.
  • the complexes are recovered from their aqueous environment, in a conventional manner using conventional equipment.
  • One preferred method is to spray dry the dispersion/emulsion. Such a step produces a powdery, dry particulate which comprises a complex of cyclodextrin and guest encapsulated by emulsifying agent.
  • a starch hydrolysate has been employed, the particulate recovered from the spray drying operation also has the dried starch hydrolysate present in the dried particulate.
  • the cyclodextrin employed in the present invention includes alpha cyclodextrin, beta cyclodextrin, gamma cyclodextrin, modified alpha cyclodextrin, modified beta cyclodextrin, modified gamma cyclodextrin, a branched alpha, beta or gamma cyclodextrin, or combinations thereof.
  • the process of the present invention has been found to work especially well with beta cyclodextrin because it increases the efficiency in forming complexes with beta cyclodextrin.
  • the cyclodextrin which is combined with the other components is in liquid form, e.g. an aqueous slurry of cyclodextrin .
  • Suitable guest molecules employed in the present invention include food additives, drugs, cosmetic components, insecticides, flavors, fragrances, pharmaceutical ingredients, agrochemical ingredients, biocides and pesticides.
  • Suitable starch hydrolysates for use in the present invention include corn syrups, corn syrup solids and maltodextrins . Good results have been obtained with maltodextrins having a Dextrose Equivalent (DE) of about 5. Good results have been obtained with corn syrups having a DE of 36.
  • the starch hydrolysate which is combined with the other components is in liquid form, e.g. an aqueous slurry of starch hydrolysate, such as a corn syrup.
  • Suitable emulsifying agents for use in the present invention include carbohydrate-based emulsifiers and especially starch-based emulsifiers.
  • the starch-based emulsifiers are starch alkenyl succinates .
  • Good results have been obtained with starch octenyl succinate and especially a hydrolyzed n-octenyl succinate of starch.
  • Suitable emulsifiers for use in the present invention include propylene glycol monostearate, polyglycerol monostearate, ethoxylated monoglyceride and lecithin.
  • Suitable emulsion stabilizers for use in the present invention include hydrolyzed n-octenyl succinate of starch (n-OSAN starch) , Gum Arabic, Gum Tragacanth and Gum Ghatti.
  • the cyclodextrin: guest molar ratio in the water is preferably between about 0.5:1 to about 5:1 and, more preferably, between about 0.75:1 to about 2:1. Good results have been obtained with a molar ratio of about 1:1, i.e. one mole of cyclodextrin to one mole of guest.
  • the amount of emulsifying agent used in the present invention is preferably about 1% to about 30% based on the total weight of the components in the combination and, more preferably, about 5% by weight to about 20% by weight. Good results have been obtained with about 10% by weight.
  • the amount of water used in the present invention is conventional.
  • the mixture comprises at least 50% by weight water based on the total weight of components in the combination .
  • the amount of starch hydrolysate used in the present invention is preferably about 0% to about 30% based on the total weight of the components in the combination and, more preferably, about 5% by weight to about 15% by weight. Good results have been obtained with about 10% by weight.
  • EXAMPLE I This example illustrates that n-OSA starch helps reduce the complex particle (agglomerate) size through homogenization and that the formation of a CD/active complex step is preferable prior to adding an emulsifying agent.
  • Table 1 The results of this example are illustrated in Table 1 below.
  • BCD beta cyclodextrin
  • MDX maltodextrin (5 DE) (a starch hydrolysate)
  • DIW Deionized water
  • Oil Orange oil (guest)
  • n-OSA C*EmCap Instant from Cerestar USA, an n-octenyl succinate of starch .(emulsifier)
  • CSS Corn syrup solid (36 DE) (a starch hydrolysate)
  • Trials A, B, C and E all the ingredients in the formulas were mixed in a plastic jug and placed in a sample shaker at 200 rpm for 12 hours at room temperature.
  • Trial D one half of the water was mixed with the BCD while the other half of the water was mixed with the oil, n-OSA and CSS. These two mixtures, in separate jugs, were shaken at 200 rpm for 12 hours at room temperature, and then they were combined.
  • each formula including the combined formula D, was blended in a Waring blender at high speed for 2 minutes with 65% power, followed by homogenization in a Gaulin- Homogenizer (Gaulin, Everett, MA) with a first step pressure of about 3000-3500 psig and a second step pressure of about 500-800 psig.
  • Gaulin- Homogenizer Gaulin, Everett, MA
  • the homogenized samples were tested on a Brinkmann Particle Size Analyzer for size distribution.
  • Trials C and D gave the finest particles, indicating effect of n-OSA (emulsifier) on BCD complex particle sizes.
  • n-OSA emulsifier
  • the particle sizes were finer after homogenization (Trial D versus Trial C) .
  • Microscopic examination of the final products showed that Trial D gave spherical particles while other trials gave mostly irregularly- shaped crystals among rod-shaped and plate-shaped crystals.
  • Trial E did not result in an emulsion-like product and BCD crystals precipitated immediately after homogenization. This shows that n-OSA interacts with BCD-oil complexes, not with BCD, to reduce the particle sizes.
  • EXAMPLE II This example illustrates that multiple passes in the homogenizer effectively reduce particle sizes of BCD complexes without pre-formation of the complexes in absence of an emulsifier.
  • Trial G was done a little differently from Trial F although the total formula was the same.
  • Half of the water was used to dissolve the emulsifier and the other half of the water was mixed with BCD and oil. Only the mixture of BCD/oil in water was blended in a Waring blender and processed for the first pass of homogenization. After the first pass and sample taking, the emulsifier solution was added and blended in a Waring blender before the second pass of homogenization.
  • Trial H used the same procedure as for Trial A except for the formula and Trial I was replicate of Trial D. After 20 days of storage of the emulsions at room temperature, without emulsifier, the particle sizes increased greatly, while with the emulsifier, the particle sizes showed good stability.
  • EXAMPLE IV This example illustrates forming complexes with a fish oil in accordance with the present invention and then drying the complex by a freeze drying technique.
  • the formulation using a blend of BCD, n-OSA and CSS (Trail M) delivered the highesr amounts of total oil and omega-3 fatty acids.
  • Trial M gave a powdered fish oil without detectable fishy odor.
  • GCD gamma cyclodextrin
  • Trials J, K, and M all the ingredients, including carrier materials listed above, water, and fish oil (40% w/w of solids) were mixed in a plastic jug and placed in a sample shaker at 250 rpm for 23 hours at 37°C.
  • Trial M two thirds of the water was mixed with BCD and the oil while the one third of the water was mixed with n-OSA and CSS. These two mixtures, in separate jugs, were shaken at 250 rpm for 23 hours at 37°C, and then were combined. The combined mixture was homogenized using a hand-held homogenizer, as those of Trials J, K, and M. Each emulsion was then freeze dried to yield a powder product.
  • a sensory test on the products showed that Trial L product has an obvious rancid odor, and that Trial K product has a very faint fish odor while products from Trials J and M did not have detectable fish odor.
  • EXAMPLE V This example illustrates preparation of powdered complexes of fish oil with a blend of BCD, n-OSA and CSS using a spray drying technique .

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  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
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Abstract

L'invention concerne des particules de complexes de cyclodextrine lisses, stables, sphériques et uniformément réparties, formées par utilisation d'un agent émulsifiant et par agitation vigoureuse et/ou homogénéisation afin de former une dispersion aqueuse de complexe hôte de cyclodextrine, et de récupérer, ensuite, les particules de complexe résultantes.
PCT/IB2000/002060 1999-12-23 2000-12-20 Complexes de cyclodextrine stabilises WO2001048024A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP00991302A EP1155043A1 (fr) 1999-12-23 2000-12-20 Complexes de cyclodextrine stabilises
JP2001548563A JP2003518515A (ja) 1999-12-23 2000-12-20 安定化シクロデキストリン複合体

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US17209999P 1999-12-23 1999-12-23
US60/172,099 1999-12-23
US68669500A 2000-10-11 2000-10-11
US09/686,695 2000-10-11

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WO2001048024A1 true WO2001048024A1 (fr) 2001-07-05

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WO (1) WO2001048024A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003015528A1 (fr) * 2001-08-14 2003-02-27 Cerestar Holding B.V. Procede de fabrication d'une composition huile-amidon et produit obtenu
US6916463B2 (en) 2002-09-24 2005-07-12 The Procter & Gamble Company Oral products having an aesthetic layer
JP2006519779A (ja) * 2003-01-20 2006-08-31 サーントゥル ナシオナル ドゥ ラ ルシェルシュ シャーンティフィク マイクロカプセル封入系およびその適用
EP1793673A1 (fr) * 2004-09-27 2007-06-13 Cargill, Incorporated Complexes d'inclusion a base de cyclodextrine et leurs procedes de preparation
US7740742B2 (en) * 2003-07-31 2010-06-22 Kao Corporation Powder composition for paper manufacturing
EP2335704A1 (fr) * 2009-11-27 2011-06-22 Les Laboratoires Servier Composition pharmaceutique comprenant un sel de strontium, de la vitamine D et une cyclodextrine
US8252358B2 (en) * 2006-10-06 2012-08-28 Rich Products Corporation Stable Protein-free whippable food product
ITMI20112244A1 (it) * 2011-12-12 2013-06-13 S I I T S R L Complesso di inclusione tra una ciclodestrina e un olio vegetale e suo impiego
WO2013188366A3 (fr) * 2012-06-12 2014-02-27 Cornell University Nanosystèmes pour la formulation de biocides efficaces à risque minimal

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Publication number Priority date Publication date Assignee Title
JP5906518B2 (ja) * 2011-08-11 2016-04-20 地方独立行政法人鳥取県産業技術センター シクロデキストリン包接化合物含有組成物の製造方法
ES2850427T3 (es) * 2016-05-24 2021-08-30 Bayer Cropscience Ag Formulaciones que contienen insecticidas volátiles con mejorada estabilidad a largo plazo y actividad
KR102195259B1 (ko) * 2019-12-17 2020-12-28 주식회사 내츄럴스푸드 토코페롤을 포함하는 혼합 분말 제형

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6638557B2 (en) * 2001-08-14 2003-10-28 Cerestar Holding B.V. Dry, edible oil and starch composition
EP1416805A1 (fr) * 2001-08-14 2004-05-12 Cerestar Holding Bv Procede de fabrication d'une composition huile-amidon et produit obtenu
EP1416805A4 (fr) * 2001-08-14 2007-01-17 Cerestar Holding Bv Procede de fabrication d'une composition huile-amidon et produit obtenu
WO2003015528A1 (fr) * 2001-08-14 2003-02-27 Cerestar Holding B.V. Procede de fabrication d'une composition huile-amidon et produit obtenu
US6916463B2 (en) 2002-09-24 2005-07-12 The Procter & Gamble Company Oral products having an aesthetic layer
JP2006519779A (ja) * 2003-01-20 2006-08-31 サーントゥル ナシオナル ドゥ ラ ルシェルシュ シャーンティフィク マイクロカプセル封入系およびその適用
US7740742B2 (en) * 2003-07-31 2010-06-22 Kao Corporation Powder composition for paper manufacturing
EP1793673A1 (fr) * 2004-09-27 2007-06-13 Cargill, Incorporated Complexes d'inclusion a base de cyclodextrine et leurs procedes de preparation
EP1793673A4 (fr) * 2004-09-27 2009-08-12 Cargill Inc Complexes d'inclusion a base de cyclodextrine et leurs procedes de preparation
US8252358B2 (en) * 2006-10-06 2012-08-28 Rich Products Corporation Stable Protein-free whippable food product
EP2335704A1 (fr) * 2009-11-27 2011-06-22 Les Laboratoires Servier Composition pharmaceutique comprenant un sel de strontium, de la vitamine D et une cyclodextrine
ITMI20112244A1 (it) * 2011-12-12 2013-06-13 S I I T S R L Complesso di inclusione tra una ciclodestrina e un olio vegetale e suo impiego
WO2013188366A3 (fr) * 2012-06-12 2014-02-27 Cornell University Nanosystèmes pour la formulation de biocides efficaces à risque minimal
EP2861085A4 (fr) * 2012-06-12 2016-04-13 Univ Cornell Nanosystèmes pour la formulation de biocides efficaces à risque minimal

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