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EP1449911B1 - Compositions aqueuses contenant des matières actives microencapsulées - Google Patents

Compositions aqueuses contenant des matières actives microencapsulées Download PDF

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Publication number
EP1449911B1
EP1449911B1 EP03003176A EP03003176A EP1449911B1 EP 1449911 B1 EP1449911 B1 EP 1449911B1 EP 03003176 A EP03003176 A EP 03003176A EP 03003176 A EP03003176 A EP 03003176A EP 1449911 B1 EP1449911 B1 EP 1449911B1
Authority
EP
European Patent Office
Prior art keywords
preparations
matrix
alcohol
active components
aqueous
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.)
Expired - Lifetime
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EP03003176A
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German (de)
English (en)
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EP1449911A1 (fr
Inventor
Nuria Dr. Bonastre Gilabert
Agustin Sanchez
Maria Dr. De Moragas
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Cognis IP Management GmbH
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Cognis IP Management GmbH
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Priority to DE50307461T priority Critical patent/DE50307461D1/de
Priority to EP03003176A priority patent/EP1449911B1/fr
Priority to AT03003176T priority patent/ATE364681T1/de
Priority to ES03003176T priority patent/ES2286341T3/es
Publication of EP1449911A1 publication Critical patent/EP1449911A1/fr
Application granted granted Critical
Publication of EP1449911B1 publication Critical patent/EP1449911B1/fr
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/12—Processes in which the treating agent is incorporated in microcapsules
    • 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
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/18—Hydrocarbons
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3749—Polyolefins; Halogenated polyolefins; Natural or synthetic rubber; Polyarylolefins or halogenated polyarylolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease

Definitions

  • the invention is in the field of laundry treatment compositions and relates to novel formulations with microencapsulated active ingredients which improve the ironing behavior, a process for the treatment of textiles and the use of special microencapsulated active ingredients for laundry equipment.
  • silicone compounds paraffin waxes and polyolefin waxes.
  • a disadvantage of these materials is that they can be incorporated homogeneously and storage stable in corresponding aqueous preparations only with difficulty. Rather, both the silicone compounds and the waxes mentioned tend to separate, with the result that the preparations must first be intensively mixed again by agitation before use. Apart from the fact that consumers do not reward such additional expenditure by a particular interest in buying, the demixed preparations are at best cloudy; the clear, transparent means desired in the market can not be produced in this way or can not be stored.
  • capsules for use in liquid fabric treatment compositions wherein the core of the capsules consists of a first substance, which vivifies the thus-finished fabric and reduces the static charge, and a second component, which is either a silicone oil or is a functionalized alkyl or ether compound.
  • the capsules themselves can be formed by polycondensation at the interfaces of two monomers and represent polyurethanes, polyesters or polyamides.
  • the WO 01/062376 A1 relates to micro- or nanocapsules that can be loaded with a wide variety of active ingredients and are available by a variety of methods.
  • microcapsules which are formed by coacervation of chitosan and anionic polymers and have a matrix of gelling agents and active substances inside.
  • the object of the present invention was thus to provide new aqueous preparations with which textiles can be so equipped that a slight ironing is possible ("easy ironing effect"), without causing the disadvantages of the prior art connected are.
  • the active ingredients should be easy to incorporate and the resulting aqueous preparations should be stable on storage.
  • Another desire was to use those active substances that have additional positive effects associated with the textile finish.
  • the invention relates to aqueous preparations, such as fabric softeners, liquid detergents or laundry aftertreatment, with microencapsulated agents, which are characterized in that the active substances are substances which improve the ironing behavior of textiles and are selected from the group formed by paraffin waxes and polyolefin waxes, wherein the shell of the capsules consists entirely or predominantly of chitosan.
  • microencapsulated active substances are used in which the shell consists wholly or at least predominantly of chitosan. Chitosan also has a tendency to grow on fibers. Because it has nourishing and antibacterial properties, the added benefit of using Chitosan microcapsules is also achieved.
  • paraffin waxes As active ingredients which improve the ironing behavior of textiles, paraffin waxes, polyolefin waxes and mixtures thereof are used.
  • paraffin waxes means saturated hydrocarbons of sufficient carbon chain length which soften or melt only at temperatures above 50 ° C., preferably above 60 ° C.
  • the paraffin waxes may also be partially oxidized, i. have free carboxyl groups.
  • polyolefin waxes means polyethylene waxes, polypropylene waxes and mixtures thereof. Suitable representatives are those which soften or melt only at temperatures above 50, preferably above 60 ° C. Particularly preferred are polyolefin waxes, e.g. the product Adalin® K (Cognis Germany GmbH & Co. KG)
  • the waxes can be used in the form of aqueous emulsions or dispersions, wherein the active substance content can be in the range of 1 to 25 wt .-%.
  • suitable emulsifiers can be used as further constituents.
  • microcapsule is understood by those skilled spherical aggregates having a diameter in the range of about 0.0001 to about 5 mm, containing at least one solid or liquid core, which is enclosed by at least one continuous shell. More specifically, it is finely dispersed liquid or solid phases coated with film-forming polymers, in the preparation of which the polymers precipitate on the material to be enveloped after emulsification and coacervation or interfacial polymerization. According to another method, molten waxes are taken up in a matrix (“microsponge”), which may additionally be enveloped as microparticles with film-forming polymers.
  • microsponge a matrix
  • the microscopic capsules, also called nanocapsules, can be dried like powder.
  • multinuclear aggregates also called microspheres
  • mononuclear microcapsules which contain two or more cores distributed in the continuous shell material.
  • Mono- or polynuclear microcapsules can also be enclosed by an additional second, third, etc., sheath.
  • the shell may be made of natural, semi-synthetic or synthetic materials.
  • shell materials are, for example, gum arabic, agar-agar, agarose, maltodextrins, alginic acid or its salts, e.g.
  • Synthetic shell materials include chemically modified celluloses, especially cellulose esters and ethers, e.g. Cellulose acetate, ethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose and carboxymethylcellulose, as well as starch derivatives, in particular starch ethers and esters.
  • Synthetic envelope materials are, for example, polymers such as polyacrylates, polyamides, polyvinyl alcohol or polyvinylpyrrolidone.
  • microcapsules of the prior art are the following commercial products (in parentheses is the shell material) : Hallcrest Microcapsules (gelatin, gum arabic), Coletica Thalaspheres (marine collagen), Lipotec Millicapseln (alginic acid, agar-agar), Induchem Unispheres (lactose , microcrystalline cellulose, hydroxypropylmethylcellulose); Unicerin C30 (lactose, microcrystalline cellulose, hydroxypropylmethylcellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar-agar) and Kuhs Probiol Nanospheres (phospholipids) as well as Primaspheres and Primasponges (chitosan, alginates) and Primasys (phospholipids) ,
  • those substances which have the property of forming gels in aqueous solution at temperatures above 40 ° C. are preferably considered as gelling agents.
  • Typical examples are heteropolysaccharides and proteins.
  • Preferred thermogelling heteropolysaccharides are agaroses which, in the form of the agar agar to be obtained from red algae, may also be present together with up to 30% by weight of non-gel-forming agaropectins.
  • the main constituent of the agaroses are linear polysaccharides of D-galactose and 3,6-anhydro-L-galactose, which are linked alternately to ⁇ -1,3- and ⁇ -1,4-glycosidic compounds.
  • the heteropolysaccharides preferably have a molecular weight in the range of 110,000 to 160,000 and are both colorless and tasteless.
  • Alternatives include pectins, xanthans (also xanthan gum) and their mixtures in question. Furthermore, preference is given to those types which still form gels in 1% strength by weight aqueous solution which do not melt below 80 ° C. and solidify again above 40 ° C. From the group of thermogeling proteins are exemplified the different types of gelatin.
  • Chitosans are biopolymers and are counted among the group of hydrocolloids. Chemically, they are partially deacetylated chitins of different molecular weight containing the following - idealized - monomer unit:
  • chitosans are cationic biopolymers under these conditions.
  • the positively charged chitosans can interact with oppositely charged surfaces and are therefore used in cosmetic hair and body care products as well as pharmaceuticals Preparations used.
  • chitosans is based on chitin, preferably the shell remains of crustaceans, which are available as cheap raw materials in large quantities.
  • the chitin is thereby used in a process first described by Hackmann et al. has been described, usually initially deproteinized by the addition of bases, demineralized by the addition of mineral acids and finally deacetylated by the addition of strong bases, wherein the molecular weights may be distributed over a broad spectrum.
  • the chitosans are generally used in the form of their salts, preferably as glycolates.
  • the matrix may optionally be dispersed in an oil phase prior to the formation of the membrane.
  • oils for this purpose for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C 6 -C 22 fatty acids with linear C 6 -C 22 fatty alcohols, esters of branched C 6 -C 13 carboxylic acids with linear C 6 -C 22 -fatty alcohols, such as myristyl myristate, myristyl palmitate, myristyl stearate, Myristylisostearat, myristyl, Myristylbehenat, Myristylerucat, cetyl myristate, cetyl palmitate, cetyl stearate, Cetylisostearat, cetyl oleate, cetyl behenate, Cetylerucat, Stearylmyristat, stearyl palmitate, stearyl stearate, Stearylis
  • esters of linear C 6 -C 22 fatty acids with branched alcohols in particular 2-ethylhexanol
  • esters of hydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols in particular dioctyl malates
  • esters of linear and / or branched fatty acids with polyhydric alcohols such as propylene glycol, dimerdiol or trimer triol
  • polyhydric alcohols such as propylene glycol, dimerdiol or trimer triol
  • Guerbet alcohols triglycerides based on C 6 -C 10 fatty acids, liquid mono- / di / triglyceride mixtures based on C 6 -C 18 fatty acids
  • esters of C 6 - C 22 -fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids in particular benzoic acid
  • the anionic polymers have the task of forming membranes with the chitosans. Salts of alginic acid are preferably suitable for this purpose.
  • Alginic acid is a mixture of carboxyl-containing polysaccharides with the following idealized monomer unit:
  • the average molecular weight of the alginic acids or alginates is in the range of 150,000 to 250,000.
  • Salts of alginic acid are to be understood as meaning both their complete and their partial neutralization products, in particular the alkali metal salts and, preferably, the sodium alginate ("algin") as well as the ammonium and alkaline earth salts.
  • algin the sodium alginate
  • ammonium and alkaline earth salts especially preferred are mixed alginates, e.g. Sodium / magnesium or sodium / calcium alginates.
  • anionic chitosan derivatives e.g. Carboxylation and especially Succinylmaschines.
  • poly (meth) acrylates having average molecular weights in the range of 5,000 to 50,000 daltons and the various carboxymethylcelluloses come into question.
  • anionic polymers it is also possible to use anionic surfactants or low molecular weight inorganic salts, for example pyrophosphates, for the formation of the enveloping membrane.
  • the microcapsules For the preparation of the microcapsules is usually prepared from 1 to 10, preferably 2 to 5 wt .-% aqueous solution of the gelling agent, preferably the agar agar ago and heated them under reflux. At the boiling point, preferably at 80 to 100 ° C, a second aqueous solution is added, which contains the chitosan in amounts of 0.1 to 2, preferably 0.25 to 0.5 wt .-% and the active ingredients in amounts of 0 , 1 to 25 and especially 0.25 to 10 Wt .-% contains; this mixture is called a matrix.
  • the loading of the microcapsules with active ingredients can therefore also amount to 0.1 to 25% by weight, based on the capsule weight.
  • water-insoluble constituents for example inorganic pigments
  • inorganic pigments can also be added at this time to adjust the viscosity, these being added as a rule in the form of aqueous or aqueous / alcoholic dispersions.
  • emulsifiers and / or solubilizers can also be added to the matrix.
  • the matrix can optionally be very finely dispersed in an oil phase under high shear in order to produce the smallest possible particles in the subsequent encapsulation.
  • the matrix has proved to be particularly advantageous to heat the matrix to temperatures in the range of 40 to 60 ° C, while the oil phase is cooled to 10 to 20 ° C.
  • the actual encapsulation takes place, ie the formation of the envelope membrane by contacting the chitosan in the matrix with the anionic polymers.
  • the optionally dispersed in the oil phase matrix at a temperature in the range of 40 to 100, preferably 50 to 60 ° C with an aqueous, about 1 to 50 and preferably 10 to 15 wt .-% aqueous solution of the anion polymer and, if necessary, at the same time or subsequently to remove the oil phase.
  • the resulting aqueous preparations generally have a microcapsule content in the range of 1 to 10 wt .-%. In some cases, it may be advantageous if the solution of the polymers contains other ingredients, such as emulsifiers or preservatives.
  • microcapsules After filtration, microcapsules are obtained which on average have a diameter in the range of preferably about 1 mm. It is recommended to sift the capsules to ensure the most even size distribution possible.
  • the microcapsules thus obtained may have any shape in the production-related framework, but they are preferably approximately spherical. Alternatively, one can also use the anionic polymers for the preparation of the matrix and perform the encapsulation with the chitosans.
  • an O / W emulsion is prepared which, in addition to the oil body, water and the active ingredients, contains an effective amount of emulsifier.
  • this preparation is mixed with vigorous stirring with an appropriate amount of an aqueous anionic polymer solution.
  • the membrane formation takes place by adding the chitosan solution.
  • the viscosity can be achieved by adding further thickening agents, such as, for example, polysaccharides, in particular xanthan gum.
  • thickening agents such as, for example, polysaccharides, in particular xanthan gum.
  • Guar-guar, agar-agar, alginates and tyloses, carboxymethylcellulose and hydroxyethylcellulose, higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyacrylamides and the like can still be supported.
  • the microcapsules are separated from the aqueous phase, for example by decantation, filtration or centrifugation.
  • the preparations may contain selected microencapsulated active compounds in amounts of 0.1 to 10, preferably 1 to 8 and in particular 2 to 5 wt .-% - based on the means.
  • the agents are aqueous solutions containing only the microcapsules and optionally suitable thickening agents. This is the case, for example, with laundry aftertreatment products of the type in which the laundry is treated immediately before ironing.
  • the preparations may contain, above all, anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants.
  • anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acyl amino
  • anionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution. Preference is given to using alkylbenzenesulfonates, alkyl sulfates, soaps, alkanesulfonates, olefinsulfonates, methyl ester sulfonates and mixtures thereof.
  • Preferred alkylbenzenesulfonates follow the formula (I), R 1 -Ph-SO 3 X (I) in which R 1 is a branched, but preferably linear alkyl radical having 10 to 18 carbon atoms, Ph is a phenyl radical and X is an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • R 1 is a branched, but preferably linear alkyl radical having 10 to 18 carbon atoms
  • Ph is a phenyl radical
  • X is an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • Alkyl and / or alkenyl sulfates which are also frequently referred to as fatty alcohol sulfates, are the sulfation products of primary and / or secondary alcohols, which preferably follow the formula (II) , R 2 O-SO 3 X (II) in which R 2 is a linear or branched, aliphatic alkyl and / or alkenyl radical having 6 to 22, preferably 12 to 18 carbon atoms and X is an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • alkyl sulfates which can be used according to the invention are the sulfation products of caproic alcohol, caprylic alcohol, capric alcohol, 2-ethylhexyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, Behenyl alcohol and erucyl alcohol and their technical mixtures obtained by high-pressure hydrogenation of technical methyl ester fractions or aldehydes from the Roelen oxo synthesis.
  • the sulfation products can preferably be used in the form of their alkali metal salts and in particular their sodium salts. Particular preference is given to alkyl sulfates based on C 16/18 tallow fatty alcohols or vegetable fatty alcohols of comparable C chain distribution in the form of their sodium salts.
  • alkyl sulfates based on C 16/18 tallow fatty alcohols or vegetable fatty alcohols of comparable C chain distribution in the form of their sodium salts.
  • branched primary alcohols are oxo alcohols, as they are accessible, for example, by reacting carbon monoxide and hydrogen to alpha-olefins by the shop process.
  • Such alcohol mixtures are commercially available under the trade names Dobanol® or Neodol®. Suitable alcohol mixtures are Dobanol 91®, 23®, 25®, 45®.
  • oxo alcohols as obtained by the classical oxo process of Enichema or the Condea by addition of carbon monoxide and hydrogen to olefins.
  • These alcohol mixtures are a mixture of highly branched alcohols.
  • Such alcohol mixtures are commercially available under the trade name Lial®.
  • Suitable alcohol mixtures are Lial 91®, 111®, 123®, 125®, 145®.
  • Soaps are to be understood as meaning fatty acid salts of the formula (III) R 3 CO-OX (III) in which R 3 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 and preferably 12 to 18 carbon atoms and in turn X is alkali metal and / or alkaline earth metal, ammonium, alkylammonium or alkanolammonium.
  • Typical examples are the sodium, potassium, magnesium, ammonium and triethanolammonium salts of caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, Linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • coconut or palm kernel fatty acids are used in the form of their sodium or potassium salts.
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol ethers, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, alk (en) yloligoglycosides, fatty acid N-alkylglucamides, protein hydrolysates (especially wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters , Polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
  • fatty alcohol polyglycol ethers, alkoxylated fatty acid lower alkyl esters or alkyl oligoglucosides are used.
  • the preferred fatty alcohol polyglycol ethers follow the formula (IV), R 4 O (CH 2 CHR 5 O) n 1 H (IV) in which R 4 is a linear or branched alkyl and / or alkenyl radical having 6 to 22, preferably 12 to 18 carbon atoms, R 5 is hydrogen or methyl and n 1 is a number from 1 to 20.
  • Typical examples are the addition products of an average of 1 to 20 and preferably 5 to 10 moles of ethylene and / or propylene oxide to caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol , Elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures. Particularly preferred are addition products of 3, 5 or 7 moles of ethylene oxide to technical Kokosfettalkohole.
  • Suitable alkoxylated fatty acid lower alkyl esters are surfactants of the formula (V), R 6 CO- (OCH 2 CHR 7) n2 OR 8 (V) in the R 6 CO is a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms, R 7 is hydrogen or methyl, R 8 is linear or branched alkyl radicals having 1 to 4 carbon atoms and n 2 is a number from 1 to 20 stands.
  • Typical examples are the formal charge products of an average of 1 to 20 and preferably 5 to 10 moles of ethylene and / or propylene oxide in the methyl, ethyl, propyl, isopropyl, butyl and tert-butyl esters of caproic acid, caprylic acid, 2 Ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid, and technical mixtures thereof.
  • the production takes place the products by insertion of the alkylene oxides into the carbonyl ester bond in the presence of special catalysts, such as calcined hydrotalcite.
  • catalysts such as calcined hydrotalcite.
  • Particularly preferred are reaction products of on average 5 to 10 moles of ethylene oxide in the ester bond of technical Kokosfettklamethylestern.
  • Alkyl and alkenyl oligoglycosides which are also preferred nonionic surfactants, usually follow the formula (VI), R 9 O- [G] p (VI) where R 8 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10. They can be obtained by the relevant methods of preparative organic chemistry.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses having 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • alkyl and / or alkenyl oligoglycosides having an average degree of oligomerization p of from 1.1 to 3.0. From an application point of view, those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4 are preferred.
  • the alkyl or alkenyl radical R 9 can be derived from primary alcohols having 4 to 11, preferably 8 to 10 carbon atoms.
  • Typical examples are butanol, caproic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol, and technical mixtures thereof, as obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 9 can also be derived from primary Derive alcohols having 12 to 22, preferably 12 to 14 carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol, and technical mixtures thereof which can be obtained as described above. Preference is given to alkyl oligoglucosides based on hydrogenated C 12/14 coconut alcohol having a DP of 1 to 3.
  • cationic surfactants are in particular tetraalkylammonium compounds, such as dimethyldistearylammonium chloride or hydroxyethyl hydroxycetyl dimmonium chloride (Dehyquart E) or else esterquats, which are typically constituents of softening agents.
  • R 10 CO for an acyl radical having 6 to 22 carbon atoms
  • R 11 and R 12 are each independently hydrogen or R 10 CO
  • R 11 is an alkyl radical having 1 to 4 carbon atoms or a (CH 2 CH 2 O) m4 H Group
  • m1, m2 and m3 are in total 0 or numbers from 1 to 12
  • m4 is numbers from 1 to 12
  • Y is halide, alkylsulfate or alkyl phosphate.
  • esterquats which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachidic acid, behenic acid and erucic acid and their technical mixtures, such as They occur, for example, in the pressure splitting of natural fats and oils. It is preferred to use technical C 12/18 coconut fatty acids and, in particular, partially hydrogenated C 16/18 tallow or palm oil fatty acids and also high-acid C 16/18 fatty acid cuts having high elaidic acid content.
  • the fatty acids and the triethanolamine in a molar ratio of 1.1: 1 to 3: 1 can be used.
  • an employment ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred esterquats are technical mixtures of mono-, di- and triesters having an average degree of esterification of from 1.5 to 1.9 and conducting from technical C 16/18 - tallow or palm fatty acid (iodine value 0 to 40) from.
  • quaternized fatty acid triethanolamine ester salts of the formula (VII) have proven particularly advantageous in which R 10 CO is an acyl radical having 16 to 18 carbon atoms, R 11 is R 10 CO, R 12 is hydrogen, R 13 is a methyl group, m1 , m2 and m3 are 0 and Y is methylsulfate.
  • quaternized ester salts of fatty acids with diethanolalkylamines of the formula (VIII) are also suitable as esterquats.
  • R 14 CO for an acyl radical having 6 to 22 carbon atoms
  • R 15 is hydrogen or R 14 CO
  • R 16 and R 17 are independently alkyl radicals having 1 to 4 carbon atoms
  • m5 and m6 in total for 0 or numbers from 1 to 12
  • Y again represents halide, alkyl sulfate or alkyl phosphate.
  • R 18 CO for an acyl radical having 6 to 22 carbon atoms
  • R 19 is hydrogen or R 18 CO
  • R 20 , R 21 and R 22 are independently alkyl radicals having 1 to 4 carbon atoms, m7 and m8 in total for 0 or numbers from 1 to 12
  • X again represents halide, alkyl sulfate or alkyl phosphate.
  • suitable esterquats are substances in which the ester is replaced by an amide bond and which preferably follow the formula (X) based on diethylenetriamine, in which R 23 is CO for an acyl radical having 6 to 22 carbon atoms, R 24 is hydrogen or R 23 CO, R 25 and R 26 are independently alkyl radicals having 1 to 4 carbon atoms and Y is again halide, alkyl sulfate or alkyl phosphate.
  • Such Amidesterquats are available for example under the brand Incroquat® (Croda) in the market.
  • alkylbetaines examples include alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • alkylbetaines are the carboxyalkylation products of secondary and in particular tertiary amines which follow the formula (XI) , R 27 is alkyl and / or alkenyl radicals having from 6 to 22 carbon atoms, R 28 is hydrogen or alkyl radicals having from 1 to 4 carbon atoms, R 29 is alkyl radicals having from 1 to 4 carbon atoms, q 1 is from 1 to 6, and Z is from 1 to 6 Alkali and / or alkaline earth metal or ammonium.
  • Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, dodecylethylmethylamine, C 12/14 cocoalkyldimethylamine, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearylethylmethylamine, oleyldimethylamine, C 16/18 tallowalkyldimethylamine, and technical mixtures thereof.
  • carboxyalkylation products of amidoamines which follow the formula (XII) , in the R 30 CO for an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds, R 31 is hydrogen or alkyl radicals having 1 to 4 carbon atoms, R 32 is alkyl radicals having up to 4 carbon atoms, q 2 is from 1 to 6 , q3 represents numbers from 1 to 3 and Z again represents an alkali and / or alkaline earth metal or ammonium.
  • Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic, caprylic, capric, lauric, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic, behenic and erucic acids and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-diethylaminopropylamine, which are condensed with sodium chloroacetate.
  • condensation product of C 8/18 coconut fatty acid N, N-dimethylaminopropylamide with sodium chloroacetate is preferred.
  • imidazolinium betaines are also suitable. These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines, such as, for example, aminoethylethanolamine (AEEA) or diethylenetriamine.
  • AEEA aminoethylethanolamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the abovementioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again C 12/14 coconut fatty acid, which are subsequently betainized with sodium chloroacetate.
  • the preparations such a high viscosity that the microcapsules remain stably dispersed, ie do not sediment over time.
  • the term increased viscosity is thus to be understood as meaning a rheology which ensures the stabilization of the microcapsules in the aqueous (surfactant) phase.
  • Such viscosities are usually above 100 and preferably above 500 mPas, preferably in the range from 200 to 2000 and in particular 500 to 1000 mPas.
  • Suitable thickeners are all the substances which give the formulations a correspondingly high viscosity.
  • Typical examples are Aerosil types (hydrophilic silicic acids), polysaccharides, especially xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters fatty acids, polyacrylates, (eg Carbopole® and Pemulen types from Goodrich, Synthalene® from Sigma, Keltrol types from Kelco, sepiolite types from Seppic, Salcare types from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol and polyvinylpyrrolidone.
  • Aerosil types hydrophilic silicic acids
  • polysaccharides especially xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl cellulose, and also higher molecular
  • Bentonites such as Bentone® Gel VS-5PC (Rheox), which is a mixture of cyclopentasiloxane, disteardimonium hectorite and propylene carbonate, have also proven to be particularly effective.
  • the proportion of these thickeners in the aqueous preparations may be 0.1 to 5, preferably 0.5 to 3 and in particular 1 to 2 wt .-% amount.
  • Two further objects of the present invention relate to a process for improving the ironing behavior of textiles by providing the fibers, yarns or fabrics with microencapsulated active ingredients selected from the group formed by paraffin waxes and polyolefin waxes and wherein the Shell of the capsules wholly or predominantly consists of chitosan and the use of microencapsulated paraffin waxes and / or polyolefin waxes in which the shell of the capsules wholly or mainly consists of chitosan, for the production of laundry treatment products.
  • agar-agar were dissolved in 200 ml of water in the boiling heat.
  • the mixture was then stirred for about 30 minutes with vigorous stirring first with a solution of 10 g of glycerol 90 ml of water and then with a preparation of 2.5 g of sodium alginate in the form of a 10 wt .-% aqueous solution, 3 g of an aqueous Paraffin wax emulsion, 0.5 g preservative (Phenonip®) and 0.5 g polysorbate-20 (Tween® 20, ICI) in 64 g of water.
  • the resulting matrix was filtered, heated to 60 ° C and added dropwise to a 1% by weight solution of chitosan glycolate in water. To obtain microcapsules of the same diameter, the preparations were then sieved.
  • Table 1 contains formulation examples for a liquid detergent (A) and a softening agent (B): ⁇ b> ⁇ u> Table 1 ⁇ / u> ⁇ /b> Composition of aqueous preparations composition A B C 12/18 cocoalcohol + 5EO Dehydol® LTS 25.0 - C 12/18 coconut alcohol + 7EO Dehydol® LT7 - - Mixed ethers 1) Dehypon® KE 3447 10.0 - Dipalmoylmethylethoxymonium Methosulfate Dehyquart® AU 54 - 25.0 Carbopol 0.49 0.49 dye 0.01 0.01 Microcapsules Ex. 1 1.0 - Microcapsules Ex. 2 - 1.0 water ad 100 1) Reaction product of 1,2-dodecene epoxide and octanol + 1PO + 40EO

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Detergent Compositions (AREA)

Claims (12)

  1. Préparations aqueuses comportant des agents actifs microencapsulés,
    caractérisées en ce que
    les agents actifs sont des substances facilitant le repassage de textiles et choisies dans le groupe constitué de cires de paraffine et de cires de polyoléfine, l'enveloppe des capsules étant constituée entièrement ou pour l'essentiel de chitosane.
  2. Préparations selon la revendication 1, caractérisées en ce qu'
    il s'agit de produits adoucissants.
  3. Préparations selon la revendication 1, caractérisées en ce qu'
    il s'agit de produits de lavage liquides.
  4. Préparations selon la revendication 1, caractérisées en ce qu'
    il s'agit de produits de post-traitement du linge.
  5. Préparations selon au moins l'une des revendications 1 à 4,
    caractérisées en ce que
    les cires de polyoléfine sont des cires à base de polyéthylène et/ou polypropylène.
  6. Préparations selon au moins l'une des revendications 1 à 5,
    caractérisées en ce que
    les agents actifs se présentent en émulsion ou dispersion aqueuse.
  7. Préparations selon au moins l'une des revendications 1 à 6,
    caractérisées en ce qu'
    elles contiennent des microcapsules d'un diamètre moyen dans la plage de 0,0001 à 5 mm, constituées d'une membrane enveloppe, et d'une matrice contenant les agents actifs, et pouvant être obtenues :
    (a1) en préparant une matrice à partir de gélifiants, de chitosanes et d'agents actifs,
    (a2) en dispersant le cas échéant la matrice dans une phase huileuse,
    (a3) en traitant la matrice dispersée avec des solutions aqueuses de polymères anioniques tout en éliminant, le cas échéant, la phase huileuse,
    ou
    (b1) en préparant une matrice à partir de gélifiants, de polymères anioniques et d'agents actifs,
    (b2) en dispersant le cas échéant la matrice dans une phase huileuse,
    (b3) en traitant la matrice dispersée avec des solutions aqueuses de chitosane tout en éliminant, le cas échéant, la phase huileuse,
    ou
    (c1) en transformant des préparations aqueuses d'agents actifs en émulsions H/E avec des corps huileux en présence d'émulsifiants,
    (c2) en traitant les émulsions ainsi obtenues avec des solutions aqueuses de polymères anioniques,
    (c3) en mettant la matrice ainsi obtenue en contact avec des solutions aqueuses de chitosane et
    (c4) en séparant les produits d'encapsulation ainsi obtenus de la phase aqueuse.
  8. Préparations selon au moins l'une des revendications 1 à 7,
    caractérisées en ce qu'
    elles contiennent les agents actifs microencapsulés en quantités de 0,1 à 10 % en poids par rapport aux produits.
  9. Préparations selon au moins l'une des revendications 1 à 8,
    caractérisées en ce qu'
    elles contiennent en outre, des tensioactifs anioniques, non ioniques, cationiques, et/ou amphotères ou zwitterioniques.
  10. Préparations selon au moins l'une des revendications 1 à 9,
    caractérisées en ce qu'
    elles contiennent en outre des agents épaississants.
  11. Procédé pour faciliter le repassage de textiles, selon lequel on apprête les fibres, fils ou articles textiles plats avec des agents actifs microencapsulés choisis dans le groupe constitué de cires de paraffine et de cires de polyoléfine, et dont l'enveloppe des capsules est constituée entièrement ou essentiellement de chitosan.
  12. Utilisation de cures de paraffine et/ou de cires de polyoléfines microencapsulées dont l'enveloppe des capsules est constituée entièrement ou essentiellement de chitosane, pour fabriquer des produits pour le traitement du linge.
EP03003176A 2003-02-18 2003-02-18 Compositions aqueuses contenant des matières actives microencapsulées Expired - Lifetime EP1449911B1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE50307461T DE50307461D1 (de) 2003-02-18 2003-02-18 Wässrige Zubereitungen mit mikroverkapselten Wirkstoffen
EP03003176A EP1449911B1 (fr) 2003-02-18 2003-02-18 Compositions aqueuses contenant des matières actives microencapsulées
AT03003176T ATE364681T1 (de) 2003-02-18 2003-02-18 Wässrige zubereitungen mit mikroverkapselten wirkstoffen
ES03003176T ES2286341T3 (es) 2003-02-18 2003-02-18 Preparaciones acuosas con productos activvos microencasulados.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP03003176A EP1449911B1 (fr) 2003-02-18 2003-02-18 Compositions aqueuses contenant des matières actives microencapsulées

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EP1449911B1 true EP1449911B1 (fr) 2007-06-13

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AT (1) ATE364681T1 (fr)
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2882765B1 (fr) * 2005-03-07 2007-04-27 Rowenta Werke Gmbh Ges Mit Bes Appareil pour repasser ou defroisser le linge comportant un reservoir d'additif
WO2012126786A1 (fr) 2011-03-22 2012-09-27 Henkel Ag & Co. Kgaa Lessive liquide comprenant des capsules
CN103806285B (zh) * 2013-10-11 2016-05-11 天津市中科健新材料技术有限公司 一种用于卫生制品的恒温无纺布制备方法

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Publication number Priority date Publication date Assignee Title
US3632296A (en) * 1968-04-12 1972-01-04 Cluett Peabody & Co Inc Application of reactants and/or catalysts to textile fabrics in microencapsulated form
DE2632318A1 (de) * 1975-07-21 1977-02-17 Procter & Gamble Zur verwendung in fluessigen textilkonditioniermitteln geeignete kapseln
ATE258417T1 (de) * 1999-07-02 2004-02-15 Cognis Iberia Sl Mikrokapseln - i
CA2385870A1 (fr) * 1999-10-05 2001-04-12 Ciba Specialty Chemicals Holding Inc. Compositions adoucissantes pour tissus
EP1257353B1 (fr) * 2000-02-23 2004-11-03 Henkel Kommanditgesellschaft auf Aktien Composition de lavage ou nettoyage comprenant des composantes sous forme de micro- et/ou nanocapsules
EP1201818A1 (fr) * 2000-10-27 2002-05-02 The Procter & Gamble Company Procédé pour le repassage du linge, et cartouche de recharge pour fers à repasser
US20030045446A1 (en) * 2001-02-12 2003-03-06 Dihora Jiten Odhavji Delivery system having encapsulated porous carrier loaded with additives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
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ATE364681T1 (de) 2007-07-15
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ES2286341T3 (es) 2007-12-01

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