WO2002020148A1 - Capsules transparentes pour agent actif - Google Patents

Capsules transparentes pour agent actif Download PDF

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Publication number
WO2002020148A1
WO2002020148A1 PCT/EP2001/010003 EP0110003W WO0220148A1 WO 2002020148 A1 WO2002020148 A1 WO 2002020148A1 EP 0110003 W EP0110003 W EP 0110003W WO 0220148 A1 WO0220148 A1 WO 0220148A1
Authority
WO
WIPO (PCT)
Prior art keywords
beads
droplets
organic phase
active
organosilicon compound
Prior art date
Application number
PCT/EP2001/010003
Other languages
German (de)
English (en)
Inventor
Michael Dreja
Wolfgang Rybinski
Matthias Hof
Herbert Leonhard
Heinz Rehage
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU2002218159A priority Critical patent/AU2002218159A1/en
Publication of WO2002020148A1 publication Critical patent/WO2002020148A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/18—In situ polymerisation with all reactants being present in the same phase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening
    • B01J13/22—Coating
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)

Definitions

  • the present invention relates to a process for the production of transparent or largely transparent polymer capsules, beads or droplets containing active or active ingredient by polycondensation of organosilicon compounds, and to the use of the transparent capsules, beads or droplets produced in this way as delivery systems for active ingredients , in particular for use in cosmetic products, pharmaceutical compositions, adhesives, washing and cleaning agents and the like.
  • Sensitive substances are often enclosed in capsules of various sizes, adsorbed on suitable carrier materials or chemically modified. The release can then be nes suitable mechanism can be activated, for example mechanically by shear, or diffusively directly from the matrix material.
  • Systems are therefore sought which are suitable as encapsulation, transport or delivery vehicles - often also referred to as “delivery systems” or “carrier systems”.
  • liposomes e.g. B. 'Nanotopes'® from Ciba-Geigy or sponge-like particles such as' Mikrosponges'® from Advanced Polymer Systems.
  • EP 0 941 761 A2 describes a process for producing microencapsulated products with organopolysiloxane walls, the shell walls being built up in situ by hydrolysis and polycondensation of organosilanes and / or their condensation products with at most four silicon atoms.
  • the organosilanes used for polycondensation are not surface-active.
  • free alcohol is formed which has to be removed.
  • the core material / shell wall ratio of the microcapsules described in EP 0 941 761 A2 is in the range from 0.3 to 4.0.
  • the weight ratio of the shell wall and capsule core to the aqueous phase is in the range from 0.05 to 0.6.
  • EP 0 304 416 AI describes a process for the formation of microcapsules or micromatrix bodies with the aid of organosilicon compounds in the presence of catalysts.
  • the silicon-containing starting monomers used are not surface-active.
  • the material to be encapsulated is limited to water-insoluble substances.
  • EP 0 934 773 A2 describes a process for the formation of microcapsules with specific capsule walls from organopolysiloxanes.
  • an organosilicon compound with at least one OH group is used, which is formed from a hydrolyzable precursor.
  • the reaction to this takes place at an acidic or basic pH, preferably at a pH of 2 to 4.
  • the starting compounds used are not surface-active.
  • WO 90/10436 describes a process for encapsulating perfume oils in membranes made of organosilanes.
  • the capsules formed are only 0.05 to 50 ⁇ m in size. Only short chain, non-surface active silanes are used as starting materials for the formation of the polymeric capsules.
  • the membranes have to be cross-linked afterwards.
  • active substances kind such as in particular dyes and fragrances, care oils, vitamins, enzymes and antibacterial substances, active ingredients and acids, bases and oxidizing agents.
  • the resulting active ingredient capsules should be transparent or essentially transparent and should be able to be colored in the desired color by adding dyes.
  • the resulting inorganic capsule or shell walls are intended to serve as a protective cover and optical delimitation aids for the substances or mixtures of substances to be encapsulated, which are used in particular in cosmetics, washing and cleaning agents and pharmaceutical products.
  • the mechanical properties of the capsules should be based on the selection of the manufacturing parameters on the desired release mechanism, e.g. B. the degree of shear, as well as the material to be absorbed and released.
  • the capsule size should be determined by the choice of manufacturing conditions, e.g. B. can be controlled by the reaction parameters, the type of shear or the density of the reactants and oils used.
  • the object can be achieved by a process which comprises the encapsulation of the active compounds by a sol-gel process at the oil / water interface by polycondensation of alkylsilanes, alkysilanols or alkylsiloxanes and thus one represents a new and simple possibility of producing transparent or essentially transparent, possibly colored microcapsules and macrocapsules with an extremely high active ingredient content and a wide application profile for numerous products in the field of detergents and cleaning agents, as well as cosmetics and pharmaceuticals.
  • the present invention thus relates to a process for the production of transparent or essentially transparent polymer capsules, beads or droplets containing active ingredient or active ingredient, which comprises the following process steps: (a) Providing an emulsion containing
  • At least one monomeric, trifunctional, surface-active organosilicon compound polymerizable by polycondensation selected from the group of trifunctional alkylhalosilanes and the corresponding alkylsilanols and trifunctional alkylsiloxanes, each with a long-chain alkyl chain;
  • a mixture of water, oil and the monomeric alkylsilane dissolved in the oil and optionally a surfactant is generally emulsified, in particular by stirring, shaking or treating with suitable dispersing devices (e.g. Ultra-Turrax®), and then the emulsion formed is allowed to react.
  • suitable dispersing devices e.g. Ultra-Turrax®
  • e.g. B. also a solution dripped into the other or sprayed.
  • ODTCS n-octadecyltrichlorosilane
  • ODTCS n-octadecyltrichlorosilane
  • n-hexadecyltrichlorosilane n-dodecyltrichlorosilane
  • 15-hexadecenyltrichlorosilane 13-tetradecenyltrichlorosilane
  • oils z. B aliphatic and aromatic oils of any kind, but especially fragrance oils such as diphenyl ether and orange oil or silicone oils can be used.
  • surfactants or block copolymers can be used as surfactants, but preferably cationic n-alkyltrimethylammonium bromides such as CTABr (cetyltrimethylammonium bromide) and anionic sodium alkyl sulfates and sulfonates or sodium alkyl ether sulfates such as, for. B. SDS (sodium dodecyl sulfate).
  • CTABr cetyltrimethylammonium bromide
  • anionic sodium alkyl sulfates and sulfonates or sodium alkyl ether sulfates such as, for. B.
  • SDS sodium dodecyl sulfate
  • the polymerization initially proceeds via aqueous hydrolysis of the alkylsilane to silanol and acid and subsequent polycondensation to give the polysiloxane or via acidic or alkaline hydrolysis of the alkylsiloxane to silanol and subsequent polycondensation to give the polysiloxane.
  • oil-filled capsules or capsules that coat the aqueous phase can be produced.
  • the capsules obtained can be characterized with the aid of optical microscopy in terms of their size and monodispersity. With the help of theological studies, statements can be made about the stability and deformability of the capsule shell.
  • Transparent or essentially transparent capsules are formed.
  • the transmission of the uncolored capsules in the laser light is generally above 90%. • ⁇ . / '
  • the present invention relates to an in-situ encapsulation of oils in water.
  • the density of the mixture of Si monomer and oil to be encapsulated which contains the fragrance or active ingredient, optionally by mixing with an inert carrier oil, is adjusted to the density of the aqueous medium or the density of the aqueous medium by addition adapted from salts or inert additives such as glucose, glycerol or PVA1 (polyvinyl alcohol).
  • the monomers can react undisturbed in the interface of the droplets to be encapsulated. This preferably takes place when the droplets are kept in suspension during the reaction or sink only slowly to the bottom of the reaction vessel.
  • a surfactant component that stabilizes the capsules in the aqueous phase is helpful.
  • a sterically stabilizing polymer such as polyvinyl alcohol (PVA1), polysaccharides or PEG (polyethylene glycol) is often helpful.
  • the storage of the fragrance or active ingredients is particularly effective if the substances have poor water solubility, i. H. are hydrophobic. Amphiphilic substances can also be easily emulsified and enclosed.
  • the proportion of fragrance or active ingredient can be varied over a wide range. Because of the very thin shell that forms, loads of more than 90% by weight of the active ingredient are possible.
  • Coloring to increase the optical stimulus can be achieved, for example, with the addition of oil-soluble dyes.
  • the present invention relates to an in-situ encapsulation of aqueous components in oil.
  • aqueous components such as. B. aqueous acids, bases, oxidizing agents, dyes, fragrances and active ingredients, in an inert carrier oil, such as. B. Dodecane
  • the volume fraction of the aqueous phase can be up to 95%.
  • the components are put together in a suitable container and evenly, e.g. B. 5 to 10 minutes, shaken, stirred or treated with a suitable dispersing device (z. B. Ultra-Turrax®).
  • z. B. Ultra-Turrax® z. B. Ultra-Turrax®
  • it is advantageous to the oil phase for. B. after about 20 to 30 minutes to replace with fresh dodecane.
  • the proportion of water in the mixture increases, the size of the capsules obtained increases. With increasing concentration of Si monomer, smaller capsules are obtained with the same type of stirring. Coloring to increase the optical stimulus can be achieved with the addition of water-soluble dyes.
  • the capsule properties can be modified by adjusting the reaction parameters.
  • the capsule properties can be tailored to the desired application.
  • the properties of the resulting inorganic polymer network such as, for example, the nature of the trifunctional alkylsilanes or alkylsilanols or alkylsiloxanes used, B. glass temperature, elasticity, stretchability and ductility as well as melting or decomposition temperature.
  • the thickness of the capsule shell can be controlled via the concentration of the Si monomers.
  • the degree of crosslinking and the thickness of the capsules can in turn be used to control the release effect or release effect when sheared.
  • the exact setting of the rheological properties of the capsule shells is of crucial importance for later applications, since the targeted shearing of the polymer shell can tear them open and thus activate the release (release) of the included fragrance and active substance.
  • the boundary deformation of a pure interfacial film made of poly-ODTCS is approximately 4%.
  • This effect can e.g. B. be used during spraying to generate an increased fragrance release from the cleaning solution with the capsules.
  • Thicker capsule shells generally have a higher resistance to shear and can be more easily incorporated into formulations.
  • Coating with a polymer or a surfactant is one way of increasing the thickness of the capsule shell, which at the same time serves to increase stability against shear.
  • Another effect that can be induced by coating is the substantiation or surface modification of the capsules for fibers, laundry and fabrics.
  • the present invention also relates to the transparent or essentially transparent polymer capsules, beads or droplets containing active or active ingredient.
  • the active or active substance-containing transparent or largely transparent polymer capsules, beads or droplets obtainable by the process according to the invention can be prepared with significantly shorter reaction times.
  • the method according to the invention therefore represents a new and simple possibility of producing selectively effective delivery systems with a broad application profile for numerous products, in particular for the fields of cosmetics and personal care, pharmacy, adhesive processing and / or washing and cleaning agents.
  • the products produced by the process according to the invention are particularly suitable as encapsulation, transport or administration vehicles, ie as delivery systems or carrier systems for a wide variety of applications (for example in the field of cosmetics and personal care) the field of pharmacy, for adhesive processing and / or for use in the detergent and cleaning agent industry).
  • the controlled or encapsulated active ingredients are released in a controlled manner so that they can be used at the desired place of use with maximum effect. Under certain circumstances, a certain depot effect can be exploited (e.g. for pharmaceutical applications).
  • the active ingredient or active ingredient-containing polymer capsules, beads or droplets provide an efficient method for controlling the release kinetics, which can be varied by the choice of the manufacturing and reaction parameters used, as previously described.
  • the present invention thus also relates to a method or a method for the controlled release of active ingredients.
  • Capsules were prepared by sol-gel polycondensation of alkylsilanes or alkylsilanols or alkylsiloxanes at the oil-water interface according to the following recipes:
  • Example 1 In-situ encapsulation of oils in water 1 to 10 mmol / L ODTCS are dissolved in diphenyl ether. Using a Pasteur pipette, this solution is dripped into a solution of 3 g NaCl and 1 to 10 ⁇ mol / L CTABr in 100 ml water. The oil droplets are agitated by gentle shaking or stirring to avoid premature coalescence. The formation of the polymer network (capsule) is complete after approx. 5-8 min; the capsules are completely hardened after approx. 30 min. The capsules obtained are optically transparent, the thickness of the capsule shells is approximately 0.5-50 ⁇ m. Table 1 gives an overview of the oils used.
  • Table 1 Variation of the oil type when encapsulating oils in water with ODTCS.
  • the concentration of ODTCS is 10 mmol / L each.
  • Encapsulated oil (g) diameter of the capsules ( ⁇ m)
  • Example 2 In-situ encapsulation of aqueous components in oil
  • Table 2 Variation of the addition to the aqueous phase when encapsulating aqueous components in oil with ODTCS.
  • the concentration of ODTCS is 1 mmol / L each

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Manufacturing Of Micro-Capsules (AREA)

Abstract

L'invention concerne un procédé pour produire des conditionnements polymères transparents ou en grande partie transparents, contenant un agent actif et se présentant sous forme de capsules, de perles ou de gouttelettes, par polycondensation de composés organiques à base de silicium. La présente invention concerne également l'utilisation de ces capsules, perles ou gouttelettes transparentes ainsi produites pour l'administration d'agents actifs, notamment pour des produits cosmétiques, des compositions pharmaceutiques, des colles, des lessives et des agents nettoyants, et autres produits similaires.
PCT/EP2001/010003 2000-09-08 2001-08-30 Capsules transparentes pour agent actif WO2002020148A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002218159A AU2002218159A1 (en) 2000-09-08 2001-08-30 Transparent active substance capsules

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10044635.3 2000-09-08
DE2000144635 DE10044635A1 (de) 2000-09-08 2000-09-08 Transparente Wirkstoffkapseln

Publications (1)

Publication Number Publication Date
WO2002020148A1 true WO2002020148A1 (fr) 2002-03-14

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Application Number Title Priority Date Filing Date
PCT/EP2001/010003 WO2002020148A1 (fr) 2000-09-08 2001-08-30 Capsules transparentes pour agent actif

Country Status (3)

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AU (1) AU2002218159A1 (fr)
DE (1) DE10044635A1 (fr)
WO (1) WO2002020148A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008002637A2 (fr) * 2006-06-27 2008-01-03 Dow Corning Corporation MICROCAPSULES à partir de la polymérisation en émulsion de TéTRAALcOXYSILANE
FR2910345A1 (fr) * 2006-12-20 2008-06-27 Oreal Particules coeur/ecorce a base de composes silicones
US8435560B2 (en) 2006-12-28 2013-05-07 Dow Corning Corporation Polynuclear microcapsules
US8815291B2 (en) 2005-06-17 2014-08-26 Austrailian Nuclear Science & Technology Organisation Particles comprising a releasable dopant therein

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011080888A1 (de) 2011-08-12 2013-02-14 Technische Universität München Verfahren zur Herstellung von poly(hydroxymethyl)-funktionellen Siloxanen und Kieselgelen
DE102012009181B4 (de) * 2012-05-10 2018-11-08 ADLER-Werk Lackfabrik Johann Berghofer GmbH & Co. KG Transparente Mikrokapseln, deren Herstellung und deren Verwendung

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0304416A1 (fr) * 1987-08-18 1989-02-22 F. Joh. KWIZDA Gesellschaft m.b.H. Procédé de fabrication de microcapsules ou de substances à micromatrice
EP0508155A1 (fr) * 1991-03-14 1992-10-14 Wacker-Chemie Gmbh Procédé de microencapsulation de produits émulsionnables dans l'eau, non-thermoplastiques
US5232782A (en) * 1989-12-27 1993-08-03 Rhone-Poulenc Chimie Magnetizable "core-shell" microspheres based on a cross-linked organopolysiloxane and a process for their preparation
EP0934773A2 (fr) * 1998-02-06 1999-08-11 Seiwa Kasei Co., Ltd. Microcapsule à paroi particulière et son procédé de fabrication
EP0941761A2 (fr) * 1998-03-12 1999-09-15 Wacker-Chemie GmbH Procédé de fabrication de produits microencapsulés à parois en organopolysiloxane

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0304416A1 (fr) * 1987-08-18 1989-02-22 F. Joh. KWIZDA Gesellschaft m.b.H. Procédé de fabrication de microcapsules ou de substances à micromatrice
US5232782A (en) * 1989-12-27 1993-08-03 Rhone-Poulenc Chimie Magnetizable "core-shell" microspheres based on a cross-linked organopolysiloxane and a process for their preparation
EP0508155A1 (fr) * 1991-03-14 1992-10-14 Wacker-Chemie Gmbh Procédé de microencapsulation de produits émulsionnables dans l'eau, non-thermoplastiques
EP0934773A2 (fr) * 1998-02-06 1999-08-11 Seiwa Kasei Co., Ltd. Microcapsule à paroi particulière et son procédé de fabrication
EP0941761A2 (fr) * 1998-03-12 1999-09-15 Wacker-Chemie GmbH Procédé de fabrication de produits microencapsulés à parois en organopolysiloxane

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8815291B2 (en) 2005-06-17 2014-08-26 Austrailian Nuclear Science & Technology Organisation Particles comprising a releasable dopant therein
US9017643B2 (en) 2005-06-17 2015-04-28 Australian Nuclear Science & Technology Organisation Particles comprising a releasable dopant therein
US9131681B2 (en) 2005-06-17 2015-09-15 Australian Nuclear Science & Technology Organisation Particles comprising a releasable dopant therein
WO2008002637A2 (fr) * 2006-06-27 2008-01-03 Dow Corning Corporation MICROCAPSULES à partir de la polymérisation en émulsion de TéTRAALcOXYSILANE
WO2008002637A3 (fr) * 2006-06-27 2008-03-06 Dow Corning MICROCAPSULES à partir de la polymérisation en émulsion de TéTRAALcOXYSILANE
US8435559B2 (en) 2006-06-27 2013-05-07 Dow Corning Corporation Microcapsules from emulsion polymerization of tetraalkoxysilane
KR101374756B1 (ko) * 2006-06-27 2014-03-17 다우 코닝 코포레이션 테트라알콕시실란의 에멀젼 중합에 의해 제조된 마이크로캡슐
FR2910345A1 (fr) * 2006-12-20 2008-06-27 Oreal Particules coeur/ecorce a base de composes silicones
EP1938891A1 (fr) * 2006-12-20 2008-07-02 L'oreal Particules coeur/écorce à base de composés siliconés
US8435560B2 (en) 2006-12-28 2013-05-07 Dow Corning Corporation Polynuclear microcapsules
US8734840B2 (en) 2006-12-28 2014-05-27 Dow Corning Corporation Polynuclear microcapsules

Also Published As

Publication number Publication date
DE10044635A1 (de) 2002-04-04
AU2002218159A1 (en) 2002-03-22

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