WO2007054232A1 - Procede d’enduction de surfaces avec des hydrogels et substrat polymerique enduit d’un revetement d'hydrogel - Google Patents

Procede d’enduction de surfaces avec des hydrogels et substrat polymerique enduit d’un revetement d'hydrogel Download PDF

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Publication number
WO2007054232A1
WO2007054232A1 PCT/EP2006/010503 EP2006010503W WO2007054232A1 WO 2007054232 A1 WO2007054232 A1 WO 2007054232A1 EP 2006010503 W EP2006010503 W EP 2006010503W WO 2007054232 A1 WO2007054232 A1 WO 2007054232A1
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WO
WIPO (PCT)
Prior art keywords
hydrogel
forming polymer
polymer
coating
composition
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Application number
PCT/EP2006/010503
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German (de)
English (en)
Inventor
Stefan DRÖSCHEL
Original Assignee
Fresenius Medical Care Deutschland Gmbh
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Filing date
Publication date
Application filed by Fresenius Medical Care Deutschland Gmbh filed Critical Fresenius Medical Care Deutschland Gmbh
Publication of WO2007054232A1 publication Critical patent/WO2007054232A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials

Definitions

  • the present invention relates to methods for coating surfaces with hydrogels, hydrogel-coated polymer substrates, and medical products comprising such polymeric substrates.
  • Hydrogel coatings are used to improve the biocompatibility of surfaces that are brought into contact with body fluids, particularly blood. Such hydrogel coatings are intended here to reduce the occupancy of the surfaces with cells and protein, which lead to the activation of the body's own defense systems against foreign materials or promote blood clotting. In addition, such hydrogel coatings are applied to polymeric substrates to increase lubricity and improve wettability for aqueous solutions.
  • hydrogels used for this purpose are polyethylene glycol (PEG) and polyvinylpyrrolidone (PVP), which are already incorporated in the preparation of corresponding medical products in the matrix of the respective polymer substrates.
  • PEG polyethylene glycol
  • PVP polyvinylpyrrolidone
  • the polymer substrates are made of polymers that are immiscible in molten or dissolved form with hydrogel-forming compounds. In this case, the substrate surfaces are usually subsequently coated with hydrogels.
  • hydrogel coatings can be bonded to polymer substrates via interlayers.
  • an isocyanate coating can first be formed on the polymer substrate surface, onto which polyvinylpyrrolidone is subsequently applied.
  • the PVP layer is fixed by heating.
  • interpenetrating polymer networks are known in order to bind polyvinylpyrrolidone hydrogels to surfaces (see WO 00/02937).
  • WO 2004/026356 describes a process for the immobilization of hydrogels on polymer substrates, in which the applied hydrogel layer is fixed on polymer surfaces with a vitamin starter and irradiation with UV light.
  • a disadvantage of this method is that hydrogel coatings can not be immobilized on surfaces which are not accessible to UV light. Therefore, it is difficult to form coatings on inner surfaces of hoses or connectors.
  • hydrogel coatings should be able to be produced inexpensively and on a large scale on surfaces.
  • claims 24 and 25 provide a solution to the underlying problem.
  • hydrogel-forming polymer is immobilized by thermal treatment under inert gas at a temperature in the range of 50-180 ° C on a surface, it is not readily predictable way to provide methods for coating surfaces with hydrogels, comprising the steps of applying to a surface a composition containing at least one hydrogel-forming polymer and forming on the surface a hydrogel coating capable of producing hydrogel coatings even in inaccessible areas of surfaces.
  • a number of other advantages can be achieved by the method according to the invention. These include:
  • the processes of the invention produce hydrogel coatings without the need to use or form harmful substances.
  • Hydrogel coatings according to the invention have a high adhesive strength on many substrates. Accordingly, these coatings are very stable on surfaces and release no harmful materials.
  • surfaces are coated with hydrogels.
  • any surface of a substrate can be coated on which the hydrogel coatings according to the invention have sufficient adhesive strength.
  • polymer substrates are coated.
  • polymer substrates it is possible to use any polymers or copolymers commonly used in particular in medical technology.
  • the polymers contained in the polymer substrate can be processed thermoplastically.
  • such polymers have a weight average molecular weight in the range of 5,000-1,000,000, preferably 10,000-500,000 g / mole.
  • polymers include, but are not limited to, vinyl polymers such as polyvinyl chloride, polyvinyl acetate, polyvinyl ethers; Polyolefins, for example, polyethylene, polypropylene and polybutylene; Polycarbonates, polyurethanes, polyesters, polyamides, polystyrenes, thermoplastic elastomers and polysiloxanes.
  • vinyl polymers such as polyvinyl chloride, polyvinyl acetate, polyvinyl ethers
  • Polyolefins for example, polyethylene, polypropylene and polybutylene
  • Polycarbonates polyurethanes, polyesters, polyamides, polystyrenes, thermoplastic elastomers and polysiloxanes.
  • polyolefins in the context of the present invention refers to polymers which consist essentially of carbon and hydrogen. These are generally selected from ⁇ -olefins, especially ethylene, propylene and butylene, for example Butadiene and isoprene, and / or aromatic hydrocarbons, for example styrene. In addition to these hydrocarbons, polyolefins may have small amounts, for example up to 10% by weight, preferably at most 5% by weight and more preferably at most 1% by weight, based on the weight of the polyolefin, of units other than those set forth above Monomers are derived, consisting of carbon and hydrogen.
  • Thermoplastic elastomers are known in the art. These include modified polyolefin elastomers (TPE-O), in particular polypropylene elastomers such as ethylene / propylene terpolymer / propylene (PP-EPDM), crosslinked ethylene / propylene terpolymer / propylene (PP-X / EPDM), nitrile Butadiene rubber / polypropylene (PP-NBR); crosslinked polyolefin elastomers (TPE-V); Elastomers based on polyetherester or polyesterester (TPE-E), polyetherurethane elastomer and / or polyesterurethane elastomer (TPE-U); Polyetheramide elastomer (TPE-A) and / or styrene elastomer (TPE-S), in particular styrene-butadiene-styrene copolymers (SBS), sty
  • copolymers are polymers comprising two, three or more different monomer units, with preferred monomer units being derived from the monomers from which the polymers illustrated above are derived.
  • Preferred copolymers include polymers which in addition to vinylic monomers additionally comprise ⁇ -olefins, for example ethylene-vinyl acetate copolymers. Furthermore, these include polyolefin copolymers, for example ethylene-propylene copolymers, and also copolymers which have styrene, ethylene and / or butylene units.
  • the polymer substrate to be coated may be a medical product or a part thereof. These include, in particular, dialyzers, tubes and tube systems, catheters, stents, urethra, filters, blood bags, apheresis sets and connectors.
  • a composition containing at least one hydrogel-forming polymer is applied to a substrate surface.
  • the hydrogel-forming polymer can be applied to the substrate in the form of a suspension, dispersion, emulsion or solution.
  • the composition comprises at least one hydrogel-forming polymer.
  • Hydrogels are well known in the art and described for example in Roempp Chemielexikon. In general, this term refers to water-containing gels based on hydrophilic but water-insoluble polymers. Accordingly, all polymers which can be used to form these hydrogels can be used to prepare the hydrogel coatings according to the invention. These include, in particular, polymers based on polyalkylene glycol, polyvinyl alcohol, polyethyleneimine, polyvinylamine, poly (meth) acrylic acids and / or poly (meth) acrylates. Preference is given to using polymers based on polyvinylpyrrolidone, polyalkylene glycol, polyvinyl alcohol and / or polyethyleneimine.
  • polymers based on polyvinylpyrrolidone are particularly preferably used for the preparation of the hydrogel coating according to the invention.
  • the hydrogel-forming polymer may comprise at least 90 weight percent polyvinylpyrrolidone, based on the weight of the hydrogel-forming polymer.
  • Polymers based on polyvinylpyrrolidone include polyvinylpyrrolidione, copolymers comprising vinylpyrrolidone units and derivatives of these polymers.
  • Preferred copolymers based on polyvinylpyrrolidone comprise at least 50% by weight, more preferably at least 75% by weight, of units derived from vinylpyrrolidone.
  • these polyvinylpyrrolidione copolymers include units which derived from vinyl esters or vinyl ethers, for example vinyl acetate, methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether and isobutyl vinyl ether.
  • Derivatives of polymers based on polyvinylpyrrolidone include units derived from polyvinylpyrrolidone and polyvinylpyrrolidone copolymers, respectively.
  • derivatives which are capable of modifying or modulating physiological reactions include compounds which may affect blood clotting or immune system functions.
  • polyvinylpyrrolidone derivatives for example, oligosaccharide-substituted PVP polymers and peptide-substituted PVP polymers can be cited.
  • An example of this is PVP-heparin complexes, as described, for example, in US Pat. No. 4,239,664, to which reference is explicitly made here.
  • the derivatives of polyvinylpyrrolidone further include polymers obtainable by polymerization of Vinylpyrrolidonderivaten.
  • the vinylpyrrolidone derivatives include, in particular, substituted vinylpyrrolidone monomers which have in particular one or more alkyl substituents.
  • Preferred alkyl substituents may have 1 to 10, more preferably 1 to 6, and most preferably 1 to 4 carbon atoms. These include in particular methyl, ethyl, propyl, isopropyl, n-butyl and tert-butyl groups.
  • the alkyl substitution can be provided both on the side chain and on the pyrrolidone ring.
  • Polymers based on polyalkylene glycol include, for example, polyethylene glycol (PEG), polypropylene glycol and / or copolymers comprising ethylene glycol and / or propylene glycol units. Furthermore, it also covers derivatives of these polymers, which are capable of modifying or modulating physiological reactions. In particular, this includes compounds which may affect blood clotting or immune system functions, as set forth above with respect to PVP.
  • PEG polyethylene glycol
  • polypropylene glycol and / or copolymers comprising ethylene glycol and / or propylene glycol units.
  • derivatives of these polymers which are capable of modifying or modulating physiological reactions. In particular, this includes compounds which may affect blood clotting or immune system functions, as set forth above with respect to PVP.
  • the molecular weight of the hydrogel-forming polymers can vary widely.
  • the hydrogel-forming polymers have a weight average molecular weight in the range of 1,000-10,000,000 g / mol, more preferably 10,000-1,500,000, and most preferably 100,000 g / mol to 13,000,000 g / mol.
  • the poly- Dispersity of the hydrogel-forming polymer Mw / Mn is preferably in the range of 1-10, more preferably 1.5-5, without this being a limitation.
  • the weight average molecular weight Mw and the number average molecular weight Mn can be determined by gel permeation chromatography (GPC).
  • Polymers based on polyvinylpyrrolidone preferably have a K value of at least 15.
  • the K value is in the range of 25-150, more preferably 90-120.
  • Preferred polymers based on polyvinylpyrrolidone have a weight-average molecular weight of 250,000 g / mol (K60), 85,000 (K80) or 1,000,000 (K90).
  • the K value is a measure of the molecular weight and is described, for example, in H. Fikentscher, Cellulose-Chemie 13 (1932), pages 58 to 64 and 71 to 74, and Roempp Chemielexikon, 10th edition.
  • the K value of the polymers can be adjusted, for example, via the amount of initiator, the temperature and the pH within the polymerization conditions.
  • hydrogel-forming polymers can be obtained commercially in many cases, their preparation and commercial suppliers being widely used in Ullmann's Encyclopedia of Industrial Chemistry 5th Ed. are presented on CD-ROM.
  • the hydrogel-forming polymer concentrations used in the hydrogel-forming composition are not specifically limited. However, the concentration should be high enough to ensure complete coating of the desired substrate surface.
  • the viscosity of the hydrogel-forming composition should be suitable for the coating method to be used. The exact concentration can be chosen accordingly by a person skilled in the art.
  • the concentration of hydrogel-forming polymer is in the range of 0.5-50 wt%, more preferably 0.1-10 wt%, and most preferably about 1 wt%.
  • the composition may preferably consist of 90.0 to 99.9% by weight of solvent and 0.1% by weight to 10.0% by weight of hydrogel-forming polymer.
  • the composition is in the form of a solution.
  • solution in this context means that the composition is essentially a homogeneous phase that has no visible inhomogeneities.
  • a harmless compound is understood as meaning a substance with an LD50 (rat)> 500 mg / kg, more preferably> 950 mg / kg and particularly preferably> 2,000 mg / kg.
  • the solvent is a safe alcohol, especially ethanol and / or isopropanol.
  • the solvent preferably has a boiling point at atmospheric pressure (1 bar) of at most 100 ° C., more preferably at most 80 ° C.
  • the solvent is preferably selected according to the substrate surface to achieve a homogeneous distribution of hydrogel-forming polymer.
  • a composition comprising at least one hydrogel-forming polymer is applied to a surface.
  • This can be done by any method known to those skilled in the art. These include, in particular, spray coatings, dip coatings, roller application and flood coatings.
  • the composition is applied to a substrate by dip coating.
  • the resulting solvent-containing layer is dried.
  • the drying is carried out using an inert gas stream, in particular a nitrogen stream.
  • the drying temperature depends on the nature of the solvent, wherein the drying is preferably carried out at temperatures in the range of 80 ° C to 120 ° C.
  • the immobilization of the hydrogel-forming polymer is carried out according to the invention by thermal treatment under inert gas at a temperature in the range of 50 ° C to 180 ° C, preferably 80 ° C to 150 ° C and most preferably 80 ° C to 120 ° C.
  • immobilization means that after this treatment, the hydrogel coating is not water-soluble, so that a hydrogel layer can be detected after treatment with water.
  • the detection of a hydrogel layer can be carried out in a known manner.
  • the friction of substrates that have a hydrogel coating decreases upon contact with water.
  • some hydrogels lead to complex formation, which can be detected by dyes.
  • the thermal treatment is carried out under inert gas.
  • any gas can be used which has no adverse effect on the immobilization of the hydrogel-forming polymer.
  • An inert gas, nitrogen and / or water vapor is preferably used as the inert gas.
  • the gas atmosphere in the immobilization treatment comprises at most 1% by volume, more preferably at most 0.5% by volume and most preferably at most 0.1% by volume of oxygen.
  • An inert gas, nitrogen and / or water vapor is preferably used as the inert gas.
  • nitrogen and / or steam is preferably used.
  • the gas atmosphere in this case preferably comprises at least 99% by volume of noble gas, nitrogen and / or water vapor.
  • the immobilization of the hydrogel-forming polymer is carried out at a pressure in the range of 0.5-3 bar, more preferably 0.8-2.5 bar and most preferably in the range of atmospheric pressure (0.95 bar to 1.05 bar ).
  • the period of immobilization treatment is not specifically limited. In general, the immobilization process is used for a time sufficient to obtain a strong, water-insoluble hydrogel coating. The exact period of time can be selected accordingly by a specialist. In general, this period is in the range of 10-60 min, without this being a restriction.
  • the thickness of the hydrogel coating is not particularly limited.
  • the hydrogel coating preferably has a thickness in the range from 10 ⁇ m to 50 ⁇ m in the swollen state.
  • hydrogel coatings do not release any such substances.
  • Harmful substances are compounds with an LD-50 (rat) of ⁇ 2,000 mg / kg, preferably ⁇ 950 mg / kg and most preferably ⁇ 500 mg / kg.
  • solvents such as dimethylformamide are among the substances of health concern.
  • a flexible 20m-long plastic tubing is wound on a drum and rinsed at room temperature with a 1% PVP-K90 solution while rotating the drum to complete wetting of the inner surface. After this flushing process, the tubing is stored in a heated room with further rotation so that the coated surfaces dry. Subsequently, a laminar flow of nitrogen is passed through the tube at near atmospheric pressure. It is maintained at a temperature of 120 ° C for a period of 30 minutes. It has proved to be advantageous, after the annealing process under nitrogen, to follow a rinsing process in order to extract non-immobilized PVP.
  • the treated tube is rinsed with 70 ° C hot distilled water for 30 min and then treated with an acid Dragendorff see solution. Under these conditions, soluble PVP moieties should elute from the surface layer. Even browning over the entire coated surface indicates an existing PVP layer compared to the rinse cycle immobilized with isopropanol. The proof with the Dragendorff see solution can also take place before the rinsing process. The browning that occurs then remains stable during a subsequent rinsing process.
  • FIG. 1 shows a characteristic inner surface of the tube, which comes about through the polymer used and the extrusion process. It can be seen on a smooth surface raised, isolated from each other tips.
  • FIGS. 2 and 3 clearly show that an unspulled hose and a flushed hose have a smooth surface compared to the untreated hose. This is an indication that the raised peaks were covered with the added PVP layer and thus are no longer visible. Since the images were taken after the rinsing process, immobilization of the PVP layer is evidently proven.

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  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Materials For Medical Uses (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne un procédé d’enduction de surfaces avec des hydrogels, comprenant les étapes suivantes : placer une solution comprenant au moins un polymère formant un hydrogel sur une surface et former un revêtement d’hydrogel sur ladite surface, ledit polymère formant un hydrogel étant immobilisé sur ladite surface par traitement thermique sous gaz inerte à une température comprise entre 50 et 180 °C et à une pression supérieure à 1 bar. La présente invention concerne également un substrat polymère enduit d’un revêtement d’hydrogel obtenu par le procédé selon la présente invention.
PCT/EP2006/010503 2005-11-12 2006-11-02 Procede d’enduction de surfaces avec des hydrogels et substrat polymerique enduit d’un revetement d'hydrogel WO2007054232A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005054106.2 2005-11-12
DE200510054106 DE102005054106A1 (de) 2005-11-12 2005-11-12 Verfahren zum Beschichten von Oberflächen mit Hydrogelen und mit Hydrogelbeschichtungen versehene Polymersubstrate

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WO2007054232A1 true WO2007054232A1 (fr) 2007-05-18

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585666A (en) * 1982-04-22 1986-04-29 Astra Meditec Preparation of hydrophilic coating
US4589873A (en) * 1984-05-29 1986-05-20 Becton, Dickinson And Company Method of applying a hydrophilic coating to a polymeric substrate and articles prepared thereby
EP0455323A2 (fr) * 1990-04-23 1991-11-06 Lrc Products Limited Procédé pour préparer des articles en caoutchouc préparés par trempage
WO1996023600A1 (fr) * 1995-02-01 1996-08-08 Schneider (Usa) Inc. Procede de preparation de revetements a base d'un melange d'hydrogels de polymeres de polyurethane-uree et de poly-n-vinylpyrrolidone
WO2000002937A1 (fr) * 1998-07-08 2000-01-20 Sunsoft Corporation Hydrogels hydrophiles a reseau polymere penetrant pour lentilles de contact

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU629203B2 (en) * 1988-03-23 1992-10-01 E.I. Du Pont De Nemours And Company Low coefficient of friction surface
US6110483A (en) * 1997-06-23 2000-08-29 Sts Biopolymers, Inc. Adherent, flexible hydrogel and medicated coatings
DE10238559A1 (de) * 2002-08-22 2004-03-04 Fresenius Medical Care Deutschland Gmbh Verfahren zur Immobilisierung von Hydrogel-bildenden Polymeren auf Polymersubstratoberflächen

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585666A (en) * 1982-04-22 1986-04-29 Astra Meditec Preparation of hydrophilic coating
US4589873A (en) * 1984-05-29 1986-05-20 Becton, Dickinson And Company Method of applying a hydrophilic coating to a polymeric substrate and articles prepared thereby
EP0455323A2 (fr) * 1990-04-23 1991-11-06 Lrc Products Limited Procédé pour préparer des articles en caoutchouc préparés par trempage
WO1996023600A1 (fr) * 1995-02-01 1996-08-08 Schneider (Usa) Inc. Procede de preparation de revetements a base d'un melange d'hydrogels de polymeres de polyurethane-uree et de poly-n-vinylpyrrolidone
WO2000002937A1 (fr) * 1998-07-08 2000-01-20 Sunsoft Corporation Hydrogels hydrophiles a reseau polymere penetrant pour lentilles de contact

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