EP1349913A1 - Microcapsules contenant des substances a action detergente et nettoyante - Google Patents

Microcapsules contenant des substances a action detergente et nettoyante

Info

Publication number
EP1349913A1
EP1349913A1 EP01990565A EP01990565A EP1349913A1 EP 1349913 A1 EP1349913 A1 EP 1349913A1 EP 01990565 A EP01990565 A EP 01990565A EP 01990565 A EP01990565 A EP 01990565A EP 1349913 A1 EP1349913 A1 EP 1349913A1
Authority
EP
European Patent Office
Prior art keywords
microcapsules
membrane
cleaning
washing
polyelectrolyte
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP01990565A
Other languages
German (de)
English (en)
Inventor
Ute Krupp
Wolfgang Von Rybinski
Dieter Nickel
Michael Dreja
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1349913A1 publication Critical patent/EP1349913A1/fr
Withdrawn legal-status Critical Current

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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules

Definitions

  • Microcapsules containing washing and cleaning-active substances are referred to as “Microcapsules containing washing and cleaning-active substances".
  • the present invention relates to a process for the production of microcapsules containing detergent and / or cleaning agents with a semipermeable capsule shell (membrane) by complexing suitable polyelectrolytes, and to the microcapsules produced in this way containing detergent and cleaning agents and their use, in particular in washing and Detergents, cosmetic products and personal care products.
  • detergents and cleaning agents contain additional active ingredients and auxiliaries that are active in washing and cleaning, which are incorporated into the formulation.
  • additional active ingredients and auxiliaries that are active in washing and cleaning, which are incorporated into the formulation.
  • Negative interactions can be in particular: destabilization of emulsions (e.g. BAC in fabric softener), decomposition of the active ingredients after prolonged storage (e.g. amino-functional silicone oils in acid detergents), general incompatibility of individual ingredients (e.g. complexation of QAVs with anionic surfactants).
  • Microcapsules or particles are used in particular in pharmacy, e.g. B. to increase the stability of the active ingredients, to cover taste, for targeted organ-specific release of active ingredients and also to avoid incompatibilities with other auxiliaries and active ingredients.
  • Microcapsules are also used in adhesive technology. Also known are fragrance capsules with gelatin as wall material, from which perfume oils are released by mechanical destruction. In general, these microcapsules are particles with diameters _ 1 mm.
  • PVAI polyvinyl alcohol
  • These capsules can e.g. B. be produced by a dripping process, wherein to increase the mechanical stability, the carrier material is crosslinked physically or chemically.
  • EP 0 782 853 A2 and the corresponding DE 195 19 804 A1 describe bioactive capsules with a variable shell, in particular for use in living tissue or in biotechnological applications, with a core containing living cells and / or enzymes and a shell consisting of several , the core is built up completely surrounding individual layers, which consist of a porous network of intertwined macromolecules, at least one of the layers consisting of a material that changes or dissolves the structure as a function of an ion concentration and / or physical quantities and / or by reagents , WO 99/02252 describes a process for the production of high-strength capsules which have a core made of a polyanionic polysaccharide, which is coated with a polycationic polysaccharide membrane.
  • the capsules described there are used in particular in the field of pharmacy, but also in the field of catalysis, biology, pesticides and herbicides, agriculture, cosmetics and the food industry.
  • US-A-4,352,883 describes a method for encapsulating living tissue, single cells, hormones, enzymes or antibodies in a semi-permeable membrane which is permeable to small molecules but is impermeable to potentially harmful large molecules.
  • the semipermeable membrane is applied to discrete, temporary capsules or gel droplets that retain their shape, the gel then being liquefied again.
  • WO 91/15196 describes an osmotic dosing system for active pharmaceutical ingredients, which consists of an outer semipermeable membrane, an osmotically active middle layer and an inner capsule, which comprises a liquid formulation with the active pharmaceutical ingredient.
  • EP 0 280 155 B1 describes the microencapsulation of biologically active material by producing a semipermeable membrane which consists of a biocompatible, non-toxic polyacid and a polybase, the polybase being formed from a special polymer with special, defined, repeating monomer units.
  • Chitosan microcapsules and networks are formed in a suspension medium which contains chitosan, acetic acid, an emulsifier and a crosslinking agent, namely glutaraldehyde.
  • the present invention is therefore based on the object of providing a capsule system which enables a wide range of applications.
  • a capsule system should be usable in particular in detergents and cleaning agents, preferably liquid detergents and cleaning agents, fabric softeners and laundry aftertreatment agents, but also in other products, such as cosmetic products and personal care products.
  • such a capsule system should have a relatively large storage stability even in water-containing products, but nevertheless enable a quick, easily inducible release of the ingredients during use and be able to be dissolved or removed without residue after use.
  • the object on which the invention is based is achieved by a capsule system which opens because of osmotic effects.
  • This is accomplished by providing capsules with a semi-permeable polymer membrane that is permeable to small molecules such as solvent and water molecules, but is impermeable or substantially impermeable to the encapsulated ingredients (e.g. enzymes), i.e. H. at least of the encapsulated ingredients is considerably slower than what happens to the solvent and water molecules.
  • the concentration of the substances dissolved in the capsules is adapted to the concentration of the substances in the surrounding medium (e.g. FWM), the capsules are stable. Do the concentrations change in the continuous phase, e.g. B. by dilution with water, there is a high osmotic pressure in the capsules, which causes them to burst or swell and thus to release the ingredients.
  • the present invention thus relates to a process for the preparation of microcapsules containing detergent and / or cleaning substances with a semipermeable capsule shell (membrane), which is characterized by an in-situ complexation of suitable polyelectrolytes or polyelectrolyte mixtures in the presence of an aqueous solution or dispersion
  • At least one matrix-forming material so that a semipermeable capsule shell (membrane) comprising the complexed polyelectrolytes (mixtures) is formed, which covers the washable and / or cleaning-active substance, completely encloses the optionally present further ingredient and the optionally present matrix-forming material.
  • the complexation reaction can be followed, if appropriate after a curing step, by removing the microcapsules.
  • Methods which are known per se and are familiar to the person skilled in the art are used here, such as in particular filtration, freeze-drying (lyophilization) or spray drying, preferably filtration.
  • excessive shear forces should not be exerted on the microcapsules so that they are not damaged.
  • the optionally carried out separation step can then optionally be followed by a method step in which at least one further semipermeable membrane layer is applied to the previously produced inner semipermeable capsule shell, wherein the additional membrane layer (s) can be constructed from the same or different material as the innermost capsule shell.
  • the additional membrane layer (s) can be constructed from the same or different material as the innermost capsule shell.
  • the method according to the invention comprises the following method steps:
  • first solution or dispersion can optionally also contain at least one matrix-forming material and the second solution or dispersion in this case can optionally also contain polyvalent metal ions (e.g. alkaline earth metal ions).
  • polyvalent metal ions e.g. alkaline earth metal ions
  • Such multivalent metal ions can cause additional crosslinking of the matrix-forming material.
  • the concentration of oppositely charged electrolyte or polyelectrolyte or of oppositely charged surfactant or of a mixture of electrolytes, polyelectrolytes or surfactants in the same or opposite positions can, for example, be equally 0.001-100 g / l, in particular 0.01-50 g / l. If a mixture of electrolytes, polyelectrolytes or surfactants with the same or opposite charge is used in the second solution or dispersion, For example, the mixing ratio of substances stored in the same or opposite directions can be between 1:99 and 99: 1, in particular between 15:85 and 85:15.
  • coreless capsules are formed, i. H. Capsules without a matrix core, which contain at least one washing and / or cleaning active substance and optionally at least one further ingredient, encased by the semipermeable membrane.
  • nucleated capsules are formed, i. H. Capsules with a matrix core, which is completely enclosed by the semipermeable capsule shell (membrane) and in which the washing and / or cleaning substance and optionally the further ingredient is embedded or embedded. This increases the stability of the capsules.
  • the semipermeable capsule shell (membrane) is formed in that a polyelectrolyte undergoes a complexation reaction with an oppositely charged electrolyte or polyelectrolyte or with an oppositely charged surfactant or with a mixture of equally and oppositely charged electrolytes, polyelectrolytes or surfactants.
  • Suitable surfactants according to the invention are all anionic or cationic surfactants known per se, provided that they form a stable complex with the polyelectrolyte and are in particular compatible with the capsule shell material formed in this way, in particular do not dissolve it.
  • Polyelectrolytes suitable according to the invention can be synthetic and natural polyelectrolytes.
  • Anionic synthetic polyelectrolytes suitable according to the invention can in particular be selected from the group of polyacrylates and methacrylates, polyvinyl sulfates, polystyrene sulfonates and polyphosphates.
  • Cationic synthetic polyelectrolytes suitable according to the invention can in particular be selected from the group of poly (N, N, N-trialkylammonium alkyl acrylate) cations, poly (N-alkylpyridinium) cations, cations of linear polyethyleneimines, cations of aliphatic ions and poly ( dimethyldiallylammonium) ammonium cations.
  • Anionic polyelectrolytes of natural origin which are suitable according to the invention can in particular be selected from the group of alkali metal and alkaline earth metal carboxymethyl celluloses, alkali metal and alkaline earth metal cellulose sulfates, alkali metal and alkaline earth metal celluronates, alkali metal and alkaline earth metal carrageenans, alkali metal and alkaline earth metal hyaluronates, and alkali metal and alkaline earth metal - lignosulfonates and alkali and alkaline earth polyribonucleates.
  • Cationic polyelectrolytes of natural origin suitable according to the invention can in particular be selected from the group of chitosans and chitosan derivatives such as quaternized chitosans, aminoalkylated and subsequently quaternized celluloses and poly-L-lysine.
  • Polyelectrolytes suitable according to the invention can also be polyampholytes, in particular polyampholytes on a natural basis, preferably on the basis of natural polypeptides.
  • the semipermeable capsule shell (membrane) can be formed by complexing reaction of at least one of the following polyelectrolyte complexing pairs:
  • the semipermeable capsule shell (membrane) can also be formed, for example, by complexing reaction of at least one polyelectrolyte with at least one surfactant, in particular cellulose sulfate / N-dodecylpyridinium chloride.
  • the semipermeable capsule shell (membrane) can also be formed by complexing reaction of at least one cationic polyelectrolyte with at least one anionic layered silicate, in particular poly (diallyldimethylammonium chloride) / montmorillonite.
  • the wash- and / or cleaning-active substance is selected in particular in such a way that it cannot or essentially cannot pass through the semipermeable membrane. At least the washing and / or cleaning active substance should diffuse through the semipermeable capsule shell (membrane) considerably more slowly, preferably by at least an order of magnitude, than water molecules.
  • the washing and / or cleaning active substance can in particular be selected from the group of washing and / or cleaning active inorganic and organic acids, in particular carboxylic acids, soil repellent and soil release active ingredients, bleaching agents such as hypochlorites, washing and cleaning active enzymatic Systems and enzymes such as amylases, cellulases, lipases and proteases, fragrances, in particular perfume oils, antimicrobial agents, in particular antibacterial, antiviral and / or fungicidal agents, graying and discoloration inhibitors, active substances for color protection, substances and additives for laundry care, surfactants, especially surfactants with fabric softener properties, as well as pH adjusting agents and pH buffer substances.
  • washing and / or cleaning active inorganic and organic acids in particular carboxylic acids, soil repellent and soil release active ingredients, bleaching agents such as hypochlorites, washing and cleaning active enzymatic Systems and enzymes such as amylases, cellulases, lipases and proteases, fragrances, in particular perfume oils, anti
  • the washing and / or cleaning-active substance is selected such that it is compatible with the capsule shell, preferably inert towards the capsule shell material. Furthermore, it should also be compatible with the other capsule ingredients.
  • the additional ingredient which may be present is selected in particular in such a way that it too cannot or essentially cannot pass through the semipermeable capsule shell (membrane) or at least diffuses considerably more slowly, preferably at least one order of magnitude slower, than water molecules through the semipermeable capsule shell (membrane) , Furthermore, it should be inert to the capsule shell material and / or should preferably have no surfactant properties.
  • the further ingredient is selected in particular in such a way that, when diluted, in particular with water, it builds up an osmotic pressure in the interior of the capsule which can explode the capsule.
  • Other ingredients suitable according to the invention can in particular be selected from the group of alcohols, glycols, in particular polyethylene and polypropylene glycols, ionic and polar compounds, inorganic and organic salts and sugars of all kinds.
  • the matrix-forming material can be selected in particular from the group of pectins, agar-agar, xanthanes, guar gum, gelatins, gel formers, polyvinyl alcohols (PVAI), gellan gum, carrageenan, starch derivatives and polysaccharides.
  • pectins agar-agar, xanthanes, guar gum, gelatins, gel formers, polyvinyl alcohols (PVAI), gellan gum, carrageenan, starch derivatives and polysaccharides.
  • reaction time for the process according to the invention can vary within wide ranges.
  • the complexation reaction proceeds spontaneously.
  • the temperatures at which the process according to the invention is carried out can vary within wide limits. In general, the invention Process at temperatures from 0 to 100 ° C, in particular 20 to 60 ° C, preferably at room temperature.
  • the pH values at which the process according to the invention is carried out can vary within wide ranges. In general, the process according to the invention is carried out at pH values from 0 to 10, in particular from 1 to 6.
  • the pressures at which the process according to the invention is carried out can vary within a wide range.
  • the process according to the invention is carried out under reduced, elevated or normal pressure, preferably under normal pressure.
  • the stability of the capsules according to the invention can be increased by applying a polymer membrane to a solid core in which the ingredients are embedded.
  • the membrane can be constructed, for example, from one or more layers of oppositely charged polyelectrolytes, which are held together due to electrostatic interactions, or other (bio) polymers.
  • Multi-layer casings can be produced, for example, by repeated dipping in polymer solutions or by methods such as spray drying.
  • the core of the capsules can e.g. B. consist of polyvinyl alcohols, starch derivatives, gelatin, etc.
  • carrier materials made of other polymers are also conceivable, which can form a matrix for encapsulating active ingredients. It is particularly advantageous if the matrix formation is reversible, for example in the case of certain starches which are physically crosslinked by polyvalent ions. This means that any stabilities can be set.
  • the microcapsules according to the invention with a semipermeable wall membrane are produced, for example, by complexing a polyelectrolyte, such as, for. B. chitosan, with vesicles from a complex mixture of cationic and anionic, d. H. equally charged and oppositely charged surfactants.
  • a polyelectrolyte such as, for. B. chitosan
  • two oppositely charged polyelectrolytes or a polyelectrolyte and an oppositely charged surfactant can also be complexed together.
  • appropriately concentrated solutions of the polymers or of surfactant (s) and polymer can be combined, in particular by dropping.
  • capsules spontaneously form which have a semipermeable membrane shell. This shell is generally permeable to the diffusion of water, but impermeable to ingredients dissolved therein, or only significantly slower, preferably at least an order of magnitude slower, can be passed through diffusion than in the case of water molecules.
  • the present invention also relates to the microcapsules obtainable by the process according to the invention.
  • microcapsules with a semipermeable capsule shell (membrane) which, in addition to water, contain at least one washing and / or cleaning active substance and optionally at least one further ingredient in the interior of the capsule, the washing and / or cleaning active substance and optionally the further ingredient can be embedded in a matrix-forming material
  • the semipermeable capsule shell (membrane) comprising a polyelectrolyte complex and the shell consisting of at least one layer of such polyelectrolyte complexes and the semipermeable membrane being permeable to water molecules and to the encapsulated washing and / or cleaning-active substances and preferably also is impermeable to the further ingredient and the matrix-forming material or at least one order of magnitude slower than can be passed to water moles, so that when the microcapsules are introduced into an aqueous phase, an osmotic pressure can build up inside the capsule, causing the
  • the semipermeable capsule shell (membrane) of the capsules according to the invention is therefore generally permeable to water molecules, but impermeable or - in comparison to water molecules - at least only passable much more slowly to the detergent and / or cleaning substance and preferably also impermeable or - in comparison to water molecules - at least passable only much more slowly for the possibly present further ingredient and the possibly existing matrix material.
  • the term "considerably slower” in the present case means in particular "at least one order of magnitude slower", based on the rate of diffusion at which the molecules diffuse through the semipermeable capsule shell (membrane).
  • the microcapsules according to the invention have average diameters of 1 to 5,000 ⁇ m, in particular 50 to 3,000 ⁇ m, preferably 100 to 2,000 ⁇ m.
  • the content of encapsulated ingredients can - depending on the desired properties of the capsules and properties of the starting materials - vary within a wide range.
  • the microcapsules according to the invention contain 1 to 99% by weight, in particular 1 to 60% by weight, preferably 2 to 50% by weight, of the detergent and / or cleaning agent, based on the total weight of the microcapsules.
  • the microcapsules according to the invention contain 1 to 99% by weight, in particular 1 to 60% by weight, preferably 2 to 50% by weight, of the further ingredient, based on the total weight of the microcapsules.
  • the microcapsules according to the invention can contain 0.1 to 50% by weight, in particular 0.5 to 30% by weight, preferably 0.5 to 10% by weight, of the matrix-forming material included, based on the total weight of the microcapsules.
  • the microcapsules according to the invention have a wide range of applications. They can be used in particular in washing and cleaning agents, preferably liquid washing and cleaning agents, fabric softeners, post-washing agents and the like, in cosmetic products and in products for personal care. They are suitable as an osmosis-controlled metering system, in particular for use in detergents and cleaning agents, preferably liquid detergents and cleaning agents, fabric softeners, laundry aftertreatment agents and the like.
  • the present invention thus also relates to detergents and cleaning agents, in particular liquid detergents and cleaning agents, fabric softeners, laundry aftertreatment agents and the like, which contain the microcapsules according to the invention.
  • the content of the microcapsules according to the invention can vary within wide limits.
  • the microcapsules according to the invention are used in amounts of 0.01 to 30% by weight, in particular 0.1 to 20% by weight, preferably 1 to 10% by weight, based on the detergent and cleaning agent.
  • osmotic pressure can e.g. B. generated by different concentrations of salt in the capsule and the surrounding outer phase, as they usually occur with dilutions.
  • a membrane-like coating which is impermeable to salts or at least only diffuses more slowly than water molecules, but is designed to be permeable to water molecules, this effect can be exploited by, for example, either including salt in the interior of the capsule or but the capsules can also be placed in a saline solution without the inclusion of salt.
  • capsules according to the invention with a semipermeable membrane shell, for example with a solution in the interior of the capsule, with a content of approx. 10% NaCI or filled with an alcoholic solution and these capsules are brought into an essentially salt-free environment, for example by dilution, so water diffuses into the interior of the capsule. This creates a positive pressure difference between the interior of the capsule and the environment, which ultimately leads to the capsule being blown up. The further content of the capsule is released.
  • the encapsulated ingredients are released regardless of the temperature by a dilution step.
  • the capsules according to the invention can consequently be used in all temperature programs. The action of mechanical forces is also not necessary.
  • membrane layers are sufficient to enclose the ingredients. If the ingredients are additionally embedded in a (initially) solid matrix core which is enveloped by the membrane, additional stabilization of the capsules according to the invention is achieved.
  • the “mesh size” or pore size of the semipermeable membrane can be set in a targeted manner, inter alia, by the choice of the polymers or the number of the individual layers.
  • the stability of the membrane can also be increased by chemical cross-linking.
  • carrier matrix e.g. a detergent enzyme
  • the capsule systems according to the invention have the advantage that they are stable in storage even in water-containing products, that they enable quick, easily inducible release of the ingredients during use and that they can be dissolved or removed without residue after use.
  • Example 2 Use of the capsules from example 1 in a liquid detergent
  • Example 1 3% of the capsules produced in Example 1 are stirred into a gel-form liquid detergent (see below for frame formulation). After a few days, the pectin core becomes due to the interaction of the complexing agents with the calcium ions partially re-liquefied from the pectin matrix. However, the active cleaning ingredient remains enclosed in the capsule by the membrane.
  • the contents are released by diluting the detergent (e.g. by a factor of 1: 100).
  • a high osmotic pressure develops in the capsules, which leads to the membrane bursting and the contents being released.
  • APG alkyl polyglycosides 1-5
  • Example 3 Production of capsules according to the invention without a matrix core.
  • Capsules were prepared by complexing polyelectrolytes with surfactant mixtures with salt content, which show an osmotic switching effect, according to the following recipe:
  • capsules according to the invention act as an osmosis switch.
  • capsules without a semipermeable wall membrane do not have the described effect.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne un procédé permettant la production de microcapsules contenant des substances à action détergente et nettoyante, et comprenant une enveloppe capsulaire (membrane) semi-perméable, par complexion de polyélectrolytes appropriés. Les microcapsules ainsi produites conviennent par exemple à l'utilisation dans des détergents et des agents de nettoyage.
EP01990565A 2001-01-09 2001-12-14 Microcapsules contenant des substances a action detergente et nettoyante Withdrawn EP1349913A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10100689 2001-01-09
DE2001100689 DE10100689A1 (de) 2001-01-09 2001-01-09 Wasch- und reinigungsaktive Substanzen enthaltende Mikrokapseln
PCT/EP2001/014782 WO2002055649A1 (fr) 2001-01-09 2001-12-14 Microcapsules contenant des substances a action detergente et nettoyante

Publications (1)

Publication Number Publication Date
EP1349913A1 true EP1349913A1 (fr) 2003-10-08

Family

ID=7670052

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01990565A Withdrawn EP1349913A1 (fr) 2001-01-09 2001-12-14 Microcapsules contenant des substances a action detergente et nettoyante

Country Status (3)

Country Link
EP (1) EP1349913A1 (fr)
DE (1) DE10100689A1 (fr)
WO (1) WO2002055649A1 (fr)

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DE10244503A1 (de) * 2002-09-25 2004-04-08 Capsulution Nanoscience Ag Methode zur Herstellung und Stabilisierung von Mikro- und Nanosuspensionen mit Amphiphilen und Polyelektrolyten
ATE387487T1 (de) * 2003-05-23 2008-03-15 Procter & Gamble Waschmittelzusammensetzung zum gebrauch in einer textilwasch- oder geschirrspülmaschine
DE10361084A1 (de) 2003-06-13 2005-01-05 Henkel Kgaa Lagerstabile Bleichmittelzusammensetzungen auf Basis von Peroxycarbonsäuren
DE10361170A1 (de) † 2003-06-13 2005-01-05 Henkel Kgaa Lagerstabiles Polyelektrolytkapselsystem auf Basis von Peroxycarbonsäuren
EP1502646B1 (fr) 2003-08-01 2016-07-13 The Procter & Gamble Company Microcapsules
EP1502645A1 (fr) 2003-08-01 2005-02-02 The Procter & Gamble Company Microcapsules
DE60312150T2 (de) * 2003-08-01 2007-11-08 The Procter & Gamble Company, Cincinnati Wässriges Flüssigwaschmittel enthaltend sichtbare Teilchen
US9271904B2 (en) 2003-11-21 2016-03-01 Intercontinental Great Brands Llc Controlled release oral delivery systems
US7955630B2 (en) 2004-09-30 2011-06-07 Kraft Foods Global Brands Llc Thermally stable, high tensile strength encapsulated actives
US7727565B2 (en) 2004-08-25 2010-06-01 Cadbury Adams Usa Llc Liquid-filled chewing gum composition
US9198448B2 (en) 2005-02-07 2015-12-01 Intercontinental Great Brands Llc Stable tooth whitening gum with reactive ingredients
EP1700633A1 (fr) * 2005-03-07 2006-09-13 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé pour l'encapsulation d'un liquide
DE102005020551A1 (de) * 2005-05-03 2006-11-09 Degussa Ag Feste, redispergierbare Emulsion
EP3307427B1 (fr) * 2015-06-09 2023-08-16 Danisco US Inc. Produits encapsulés osmotiques à éclatement

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Also Published As

Publication number Publication date
DE10100689A1 (de) 2002-07-18
WO2002055649A1 (fr) 2002-07-18

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