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WO2008116330A2 - Couche multifonction sur des fibres textiles et structures planes permettant de recevoir et de libérer des substances actives - Google Patents

Couche multifonction sur des fibres textiles et structures planes permettant de recevoir et de libérer des substances actives Download PDF

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Publication number
WO2008116330A2
WO2008116330A2 PCT/CH2008/000107 CH2008000107W WO2008116330A2 WO 2008116330 A2 WO2008116330 A2 WO 2008116330A2 CH 2008000107 W CH2008000107 W CH 2008000107W WO 2008116330 A2 WO2008116330 A2 WO 2008116330A2
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WO
WIPO (PCT)
Prior art keywords
phase
multifunctional layer
layer according
membrane
composite
Prior art date
Application number
PCT/CH2008/000107
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German (de)
English (en)
Other versions
WO2008116330A3 (fr
Inventor
Oliver Marte
Martin Meyer
Original Assignee
Tex-A-Tec Ag
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 Tex-A-Tec Ag filed Critical Tex-A-Tec Ag
Publication of WO2008116330A2 publication Critical patent/WO2008116330A2/fr
Publication of WO2008116330A3 publication Critical patent/WO2008116330A3/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
    • 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

Definitions

  • the invention relates to a multifunctional layer on textile fibers and fabrics for the active ingredient in and dispensing according to claim 1, as well as processes for their preparation and processes using the same according to claims 23 to 34.
  • a highly topical subject in this regard are functional layers on textiles worn close to the body, which make it possible to transfer cosmetic and therapeutic active substances to the skin or transdermally, after these active substances were previously incorporated into the functional layer.
  • the range of active ingredients used in this regard is very broad, ranging from simple molecules such as vitamin E to complex natural products with a Variety of species that lead to interactions and synergisms of the various mechanisms of action that can not be used in the oral administration of such preparations.
  • the drug delivery layers known today in the textile industry consist essentially of a polymer layer sorbing the active substance and / or of particulate "cage molecules" such as cyclodextrins or dendrimers (HJ Buschmann et al., Textiles as depot for fragrances, Fragrances - S ⁇ FW Citernesi, P. Cappellori, Cosmetic Clothes - Fabrics with Protective Functions, Fragrances - S ⁇ fW Journal, 127 (2001), pp. 64-71, HJ. Buschmann, E. Schollmeyer, textiles with cyclodextrins as passive protection against mosquitoes, Melliand Textilberichte 10 (2004), pp. 790-792). In most cases, these layers are loaded directly during their production and are therefore so-called "one-way" layers.
  • the kinetics for the release of the active substance is in all first or pseudo-first order D rrug delivery functional layers realized today. This means that the temporal substance release decreases exponentially. On the one hand, the freshly loaded layer thus leads to a significant excess of the active substance on the skin and, on the other hand, to a rapid depletion of the active substance in the functional layer.
  • the object of the invention is to provide a multifunctional layer on textile fibers and fabrics for active ingredient absorption and Abgab, and provide methods for their preparation and methods using the same, both a controllable kinetics for delivery of the active substance and a certain washing resistance in the layer ensure stored active substance.
  • a washing resistance of the active substances stored in the multifunctional layer limited to a few washing cycles, in order to save on active substance costs and to simplify the use of such textiles or garments;
  • Controllability of the kinetics for delivery of the active substance in order to adapt the kinetics of the absorption rate through the skin and thereby to avoid undesirable side effects due to excess concentrations of the active substance on the skin (fat feeling, wetness, etc.);
  • the realization of the various objectives is carried out with a multi-phase layer concept, which has a clear target-oriented layer structure and has an active substance absorption by the skin adapted transport mechanism of the substance stored in the layer.
  • phase I An innermost phase (Phase I) of the multifunctional layer forms a storage medium later. applied or to be introduced active substances S 1 -.
  • the phase I can be both particulate and flat, the fiber enveloping formed and located on the fiber surface F of a textile fibers or fabrics.
  • the ingredients incorporated in this phase I cause a polarity, which results in a very high affinity for lipophilic substances (active substances S 1 ).
  • Phase I is able to absorb up to 200% of its own mass of lipophilic substances.
  • the phase I has a first shell with membrane character, or a membrane M1 similar to one Vacuole of eukaryotic cells.
  • the permeability for amphiphilic cationic or anionic compounds is determined by the prevailing in the membrane M1 pH. This is the case in particular when it is a dipolar membrane M1, ie the layer enveloping the phase I has a betaine structure.
  • phase I forms a storage medium, or a storage phase for the active substance S.
  • Phase I consists of at least one lipophilic, water-insoluble, non-reactive and / or amino and / or OH-functional Compound used as a monomolecular, oligomeric and / or polymeric compound.
  • Phase I is chemically fixed in the presence of reactive compounds with suitable crosslinker systems, which preferably takes place after application to the textile substrate. This results in a non-water-soluble gel or a gel body.
  • polysiloxanes As unploused amino- and hydroxyl-containing compounds derivatized polysaccharides, polysiloxanes, polyurethanes, polyesters and polyamides, ester and acid waxes are used.
  • Polymers which are terminated as preferred lipophilic amino- and OH-groups are silicone compounds which are preferably crosslinked with di- or polyisocyanates.
  • phase I is the use of predominantly nanoscale polymeric silicic acids. These are coated with at least one lipophilic .Amino and / or OH-functional compound with the addition of suitable crosslinkers and at least one amphiphilic polymeric compound and crosslinked as described above.
  • the advantage of using coated nanoparticles lies in their higher mechanical strength, which may be of importance depending on the textile material or its intended use.
  • Both the pure gel bodies and the gel bodies solidified with polysilicic acids have in the particulate state a size of 200-1000 nm, preferably of 500-800 nm.
  • ingredients for the formation of the membrane M1 are monomeric and polymeric lipophilic-hydrophilic (amphiphilic) acting substances that show an orientation (hydrophobic / hydrophilic) due to these properties in the boundary phase 'gel body / water'.
  • the orientation takes place on its own momentum when the gel phase is stirred into an aqueous solution containing the crosslinking chemical.
  • the crosslinking of the amphiphilic substance forming the boundary phase results in a membrane M1, or a membrane layer which encloses the active substance reservoir.
  • non-ionic, cationic and anionic surfactants may be mentioned whose fatty residues from a C 3 -C 24 -Fettkohlenwasserstoff- chain (preferably C 12 -C 18 ) such as sorbitan laurate, laurylamine or dilaurylamine, quaternary compounds such as dimethyllaurylbenzylammonium chloride or dialkyldimethylammonium chloride and anionic compounds such as phospholipids, alkyl and Alkyllaurylsulfonate.
  • a C 3 -C 24 -Fettkohlenwasserstoff- chain preferably C 12 -C 18
  • sorbitan laurate laurylamine or dilaurylamine
  • quaternary compounds such as dimethyllaurylbenzylammonium chloride or dialkyldimethylammonium chloride
  • anionic compounds such as phospholipids, alkyl and Alkyllaurylsulfonate.
  • amphiphilic polymers such as fat-modified polysaccharides and acrylates having a fatty hydrocarbon chain of C 3 -C 24 , preferably C 12 -C 18 , or alcohol ethoxylate maleate / ⁇ -olefin copolymers.
  • amphiphilic compounds such as ethylene oxide derivatives (EO 2 - EO 20 ) and lipophilic radicals (C 3 -C 24 ) carrying polyelectrolytes, which are also crosslinkable, eg Pemulen (Noveon, Germany).
  • the crosslinking of the membrane M1 forming compounds is made in contrast to the Geivemetzung with a reaction technically different cross-linking system.
  • a typical example is the use of an amino group-terminated silicone wax and a diisocyanate forming the active substance-receiving gel bodies (Phase I) and an alcohol ethoxylate maleate / ⁇ -olefin copolymer with an aziridine crosslinker, which form the first membrane layer M1 around the gel body ,
  • the choice of the crosslinker system is based on the reaction groups present in the particular system to be crosslinked.
  • Nucleophilic reaction groups such as OH-R, H 2 NR are preferably crosslinked in phase I and phase II with isocyanates, dialdehydes and ⁇ -Arninoalkyl michs occurn.
  • R-CONH 2 or R 1 -CONH-R 2 are preferably used in the membrane M1 with ⁇ -aminoalkylation products or dialdehydes (eg glutaric acid). aldehyde) and carboxyl-bearing compounds with aziridines.
  • R is representative of an aliphatic, aromatic or heterocyclic radical.
  • typical crosslinkers are: 1,6-diisocyanatohexane (Bayer, Germany), 3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate (Hüls, Germany) or uretdione of 2,4-diisocyanatotoluene (Bayer , Germany).
  • the aziridines used are divided into aliphatic and aromatic.
  • Typical representatives of aliphatic propylenimine derivatives are: 1,1'-azelaoyl-bis (2-methyiaziridine) and N, N ', N ", N'" - tetrapropylene-1,2,3,4-butanetetracarboxamide.
  • Typical representatives of aromatic propylenimine derivatives are: toluene-2,6-dipropyleneurea (TPH) or diphenylmethane-bis-4,4'-N, N'-dipropyleneurea.
  • phase II shows, according to the concept, a markedly reduced absorption capacity for lipophilic active substances in comparison to phase I. It can consist of several layers that differ physically and chemically, but always have membrane character and thus the kinetics for delivery of the active substance compared to conventional drug delivery layers essential changes. Due to the ingredients used to prepare the phase II (membrane phase), this layer tends to be hydrophilic and capable of adsorbing water. The possibility of water sorption is of essential importance to the inventive concept. The water absorption and the resulting swelling of the phase II or of the membrane matrix produces an aqueous barrier layer which largely prevents both the washout process of the active substance and the access of wash liquor ingredients.
  • Phase II which forms the outer membrane phase, encloses the gel bodies or the gel layer with its membrane M1, which represents the active substance reservoir (phase I).
  • the preparation of the phase II is carried out by the use of various differently polar, in water. Partial swelling and crosslinkable polymers. Examples of the polymers to be used are polyacrylates, polyurethanes, derivatized polyvinyl alcohols and acetates, polysaccharides and their derivatives, gelatin, etc.
  • the layered polymers should be chosen such that the hydrophilic character dominates ( HLB values> 12). On the one hand results in only limited solubility of the active substance S and on the other hand, an increased water absorption.
  • phase II Known drug delivery layers show a first-order delivery kinetics while, according to the coating concept according to the invention for the first 2/3 of the active substance mass, a delivery kinetics of quasi-zeroth or pseudo-zero order is realized.
  • the solubility of the active substance in phase II largely determines the delivery rate.
  • the release rate is thus controlled by the chemical nature of the phase II, or via the components which form the phase II as a membrane layer.
  • phase III forms the boundary layer, or the boundary phase 'phase M / air' or 'phase II / Hauf. While the phase II is hydrophilic dominated, the phase III in the formed layer again shows a predominantly hydrophobic character. Due to the intrinsically amphiphilic structure of the compounds forming the phase III, a thermodynamically favored orientation of the apolar, aprotic molecule radicals to the air results. Thus, this boundary phase has at least the dimension of a molecular layer.
  • suitable amphiphilic substances can be monomolecular as well as used as polymers, for example in the form of a fluorocarbon resin (Softgard M3, soft Chemicals, Italy).
  • phase III serves on the one hand the soil repellency while wearing the garment and on the other hand, the rejection of polar but also non-polar washing liquor ingredients.
  • the phase III can also be constructed in several phases, but each of the sub-phases performs the same function.
  • the third phase Mi which is likewise emulsified in the second phase II, preferably consists of a crosslinkable polymer of a fluorinated fatty hydrocarbon (C 2 -C 121, preferably C 4 -C 8 ).
  • the phase III forms the dirt-repellent boundary layer by self-organization during the layer drying.
  • Phase II crosslinker is added.
  • These are preferably isocyanates or ⁇ -aminoalkylation products in combination with corresponding catalyst systems.
  • isocyanates dibutyltin laurate or 1, 4-diazabicyclo [2.2.2] octane are used.
  • metal-set catalysts organic and inorganic acids and their mixtures of metal salt catalysts and acids such as MgCl 2 - used 6 H 2 O and citric acid.
  • a fourth phase IV to be introduced optionally represent bactericidal and / or fungicidal components or compounds which are incorporated into phase II. These serve exclusively to protect the multifunctional layer and the active substances stored therein from bacterial and / or fungicidal infestation.
  • the coating concept according to the invention largely avoids contamination of the skin with bactericidal and / or fungicidal compounds and thus minimizes or eliminates the risk of transdermal absorption of these compounds.
  • the optionally used fourth phase IV which consists of bactericidal and / or fungicidal compounds, is also admixed with the formulation of phase II (membrane phase). These are inorganic compounds, in particular metal particles, ceramic particles with metal layers of copper and silver and their salts.
  • organic compounds or quaternary ammonium compounds carrying reactive groups such as e.g. Dimethyltetradecyl (3-trimethoxysilyl) propylammonium chloride, dimethyloctadecyltrimethoxysilylpropylammonium chloride or aldehyde and peroxide releasing compounds.
  • Phase IV can also consist of several subphases, all of which serve the same function. multiphase drug delivery layer.
  • the active substance in the nano-container or in phase I with a concentration A is in equilibrium with the active substance S in the matrix, or in phase II with a concentration B.
  • the corresponding transport constants are designated ⁇ ⁇ and r .
  • the concentration B of the active substance in the matrix is transferred to the skin with a transport constant r 2 on which a concentration C of the active substance S is built up and sorbed by the skin with a transport constant r 3 , the concentration D of which in the Skin dissolved active substance concentration corresponds.
  • a further great advantage of the coating concept according to the invention is the production of composites, which, on the one hand, enormously facilitates the formulation technology of the textile supplier and, on the other hand, substantially increases process safety.
  • One or more water-insoluble compounds such as silicone waxes and oils, micronized ester and amide waxes which may also carry reactive groups, are mixed and dissolved or dispersed in a solvent adapted to the waxes or oils.
  • the solvents to be used are in an M number range of 8-20, preferably 12-15.
  • a polyfunctional crosslinking reagent having at least two crosslinking groups per molecule is added and the solution L1 is heated to 25-50.degree.
  • Preferably used crosslinking reagents are free and blocked polyisocyanates, ⁇ -aminoalkylation products and dialdehydes.
  • phase I forming polymer solution or suspension is emulsified to form Mikrocontainem in a second solution L2 by means of a Hochdruckhomogenisier learners.
  • the second solution contains a water-soluble electrolyte to adjust an ionic strength of 0.005 - 0.1, preferably 0.01 - 0.05, and an amphiphilic crosslinkable substance and a crosslinking component.
  • droplets or particles are formed whose diameters are 200-1000 nm, preferably 500-800 nm, which are enveloped by the amphiphilic substance and thus form a membrane M1 in combination with the crosslinker present.
  • the emulsifier system consists of a combination of a carboxyl-bearing and an amino-terminated surfactant, this combination leading to a betaine structure of the membrane M1.
  • pressure-resistant microcontainers can be produced by adding highly porous organic and / or inorganic particles to phase I.
  • microcontainers produced in this way represent the composite K1, which is later processed with the composite K2 into a finishing formulation.
  • phase II which envelops the phase I and membrane M1 in the multifunctional layer, is hydrophilic dominated and also has membrane character, or it provides a
  • phase II At least one polymer which is water-soluble or in the form of an emulsion in water-insoluble form is used. When using water-soluble it is imperative to use an adequate crosslinking agent.
  • an amphiphilic substance is added, preferably a fluorocarbon resin emuted in water.
  • bactericidal and / or fungicidal substances are added in this phase.
  • the thus completed phase since it is present as an emulsion, conveniently emulsified again by means of a high pressure homogenizer and is now available as a composite K2 for the preparation of a finishing formulation.
  • x g of the composite K2 are metered into a water reservoir and, after intensive mixing, mixed with y g of the composite K1.
  • the mixing ratio is dependent on the goals that the multifunctional layer has to meet.
  • Typical mixing ratios of composite K1 to composite K2 range from 90/10 to 20/80%, preferably 60/40 to 30/70%.
  • Any further ingredients serve to adjust the pH and to ensure wettability of the textile material by the finish formulation.
  • the finish formulation to the textile substrate is by a padding, coating or spraying process.
  • the liquor order is based on the fiber material of the textile material and is 30 - 80% based on the dry weight of the textile material.
  • the drying conditions should be selected so that the cooling limit temperature on the fabric is between 25 and 50 ° C. Under these conditions, the boundary layer, or the boundary phase 'phase H / air' can form, which has a barrier function to prevent the ingress of dirt and Waschflotteningredienzien in membrane M2 (membrane phase).
  • Example 1 Production of a Repeatable Multifunctional Layer to be Loaded.
  • This polymer solution is emulsified in 64.9 g of a 0.05 molar sodium chloride solution containing 4.5 g of an alcohol ethoxylate maleate / ⁇ -olefin copolymer. Subsequently the emulsion are 7 (Fievo Chemie, Netherlands) were added and stirred for 15 minutes at about 30 0 C 00:11 g Aziridinvernetzer XAMA.
  • the emulsion thus prepared contains the phase I coated with a membrane M1 in a droplet size of 700-800 nm.
  • the formulation thus prepared is applied to the textile material by means of an impregnation process.
  • the fleet order is 70% based on the dry weight of the textile material.
  • the drying is performed at a cooling limit temperature 25-70 ° C, preferably at 40 - 50 0 C.
  • the layer fixing is carried out at 120-170 0 C, preferably at 140-160 0 C for 1 - 5 minutes, preferably 2 - 3 minutes.
  • the particulate suspension is poured into an aqueous 0.03 molar sodium sulfate solution
  • the composite K1 thus produced contains the phase enveloped by a membrane M1
  • an acrylate resin mixture (10% binder VSO, 90% binder ASM, soft Chemicals, Italy) are stirred into 260 g / kg of water and 80 g / kg of a fluorocarbon resin (Softgard M3, soft chemicals, Italy) and 80 g / kg IPDI trimer (Bayer Material Science, Germany) and 80 g / kg Dorafresh AG (silver salt suspension, Dohmen GmbH, Germany) and homogenized.
  • the composite K2 thus produced is used in combination with composite K1 by the customer for the preparation of the application liquor formulation.
  • 600 g / l of water serve as a template into which 80 g / l of the composite K1 and 120 g / l of the
  • Komposits K2 be stirred. In addition, the solution becomes 200 g / L of a 5%
  • Methocel solution (Methocel K100, Dow Germany GmbH & Co.) added and homogenized.
  • the fleet application to the textile substrate is carried out by a padding process with a liquor order of 70 - 72% based on the substrate dry weight.
  • the subsequent drying takes place at a cooling limit temperature on the fabric of

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention concerne une couche multifonction sur des fibres textiles et des structures planes permettant de recevoir et de libérer des substances actives. Cette couche présente une première phase (I) qui est constituée d'au moins un composé lipophile insoluble dans l'eau. Au moins une substance active (S) est introduite dans cette première phase (I), laquelle phase (I) constituant à cette fin un milieu de support. La première phase (I) est entourée d'une première membrane (M1) qui est perméable aux matières lipophiles et hydrophiles non dissociées. La couche multifonction selon cette invention présente également au moins une deuxième phase (II) qui est conçue sous forme d'autre membrane hydrophile (M2) et qui adsorbe l'eau. La vitesse de libération de la substance active incluse peut être commandée par l'intermédiaire de l'établissement de la deuxième phase (II). Au moins une autre troisième phase (III), constituée de composants amphiphiles qui portent des groupes de corps gras et/ou des groupes hydrocarbure perfluoré, forme une couche limite par rapport à l'air. Cette invention concerne également des procédé de production de composites au moyen de ladite couche multifonction, lesquels procédés permettent de recharger la couche multifonction avec des substances actives principalement lipophiles. Il est ainsi possible de commander la libération des substances actives sur la peau qui est en contact avec des textiles pourvus de ces substances et portés près du corps.
PCT/CH2008/000107 2007-03-27 2008-03-15 Couche multifonction sur des fibres textiles et structures planes permettant de recevoir et de libérer des substances actives WO2008116330A2 (fr)

Applications Claiming Priority (2)

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CH4892007 2007-03-27
CH489/07 2007-03-27

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WO2008116330A2 true WO2008116330A2 (fr) 2008-10-02
WO2008116330A3 WO2008116330A3 (fr) 2009-05-07

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH699118A1 (de) * 2008-07-15 2010-01-15 Tex A Tec Ag Multifunktionelle, responsive Funktionsschichten auf festen Oberflächen und Verfahren zur Herstellung dazu.

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1359247A1 (fr) * 2002-04-30 2003-11-05 Cognis Iberia, S.L. Fibres et tissus finis avec des microcapsules
WO2006007753A1 (fr) * 2004-07-20 2006-01-26 Schoeller Textil Ag Apprets pouvant etre appliques plusieurs fois sur des fibres textiles et des tissus

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1359247A1 (fr) * 2002-04-30 2003-11-05 Cognis Iberia, S.L. Fibres et tissus finis avec des microcapsules
WO2006007753A1 (fr) * 2004-07-20 2006-01-26 Schoeller Textil Ag Apprets pouvant etre appliques plusieurs fois sur des fibres textiles et des tissus

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH699118A1 (de) * 2008-07-15 2010-01-15 Tex A Tec Ag Multifunktionelle, responsive Funktionsschichten auf festen Oberflächen und Verfahren zur Herstellung dazu.
WO2010006457A1 (fr) 2008-07-15 2010-01-21 Heiq Materials Ag Couches fonctionnelles réactives à fonctions multiples sur surfaces solides et leurs procédés de fabrication

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