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
  • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
  • A61L29/08—Materials for coatings
  • A61L29/085—Macromolecular materials
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
  • C10M107/40—Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
  • C10M107/44—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
  • A61M25/00—Catheters; Hollow probes
  • A61M25/0043—Catheters; Hollow probes characterised by structural features
  • A61M25/0045—Catheters; Hollow probes characterised by structural features multi-layered, e.g. coated
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
  • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
  • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M107/28—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
• • 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
  • A61L2400/00—Materials characterised by their function or physical properties
  • A61L2400/10—Materials for lubricating medical devices
• • 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
  • A61L2420/00—Materials or methods for coatings medical devices
  • A61L2420/02—Methods for coating medical devices
• • 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
  • A61L2420/00—Materials or methods for coatings medical devices
  • A61L2420/06—Coatings containing a mixture of two or more compounds
• • 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
  • A61L2420/00—Materials or methods for coatings medical devices
  • A61L2420/08—Coatings comprising two or more layers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
  • A61M25/00—Catheters; Hollow probes
  • A61M25/0043—Catheters; Hollow probes characterised by structural features
  • A61M25/0045—Catheters; Hollow probes characterised by structural features multi-layered, e.g. coated
  • A61M2025/0046—Coatings for improving slidability
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
  • C10M2209/0845—Acrylate; Methacrylate used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
  • C10M2209/0863—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/045—Polyureas; Polyurethanes
  • C10M2217/0453—Polyureas; Polyurethanes used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/50—Medical uses
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/023—Multi-layer lubricant coatings

Definitions

• the present disclosure relates generally to coatings for medical appliances. More specifically, the present disclosure relates to polymeric coatings for medical appliances, the polymeric coatings having high levels of durability and selectable lubricity. Related methods are also disclosed.
• FIG. 1 depicts a representation of the structure of a coating in accordance with an embodiment.
• FIG. 2A is a cross-sectional view of a medical device before the application of a layer of a coating.
• FIG. 2B is a cross-sectional view of a medical device after the application of a base layer of the coating.
• FIG. 2C is a cross-sectional view of a medical device after the application of a top layer of the coating.
• FIG. 3 is a graph of a lubricity test of exemplary coatings.
• FIG. 4 is a graph of a wear/durability test of exemplary coatings.
• FIG. 5 is a graph of an additional wear/durability test of exemplary coatings.
• FIG. 6 is a graph of an additional wear/durability test of exemplary coatings.
• a coating may be used for such an elongated medical device (e.g., a catheter, guidewire, hypotube, stylet, etc.).
• the coating may be applied to or disposed on at least a portion of a surface of the medical device.
• the coating may comprise one or more biocompatible polymeric materials, where each polymeric material or the particular combination thereof is selected to impart particular properties to the coating.
• lubricity and durability can be of particular relevance to typical use of these devices, which can involve navigating tortuous but delicate anatomical features to reach a target site while effectively transiting intervening areas of resistance.
• a coating for a medical device comprises a base coating layer and a top coating layer, where the top coating layer comprises two or more polymeric components.
• the types and relative amounts of the components of the top coating layer can be selected to impart particular levels of lubricity and durability to the coating.
• n, p, and q are integers greater than or equal to 1 .
• R can include various aromatic or aliphatic groups.
• the R can include groups to form methylene diphenyl diisocyanate (MDI), toluene diisocyanate (TDI), hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), or 4,4’-dicyclohexylmethane diisocyanate (HMDI, etc.
• MDI methylene diphenyl diisocyanate
• TDI toluene diisocyanate
• HDI hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• HMDI 4,4’-dicyclohexylmethane diisocyanate
• materials in the base coating layer are suited for application to nitinol or nitinol that is optionally jacketed with tungsten-impregnated polyurethane.
• the base coating layer has a thickness of from about 2 pm to about 20 pm, and more particularly from about 2 pm to about 10 pm, from about 10 pm to about 20 pm, or from about 5 pm to about 15 pm.
• the thickness of the base coating layer can be selected so as to be suitable for the dimensions of the medical device coated with the coating. For example, in coatings for guidewires, a thicker coating may be used for a larger diameter guidewire than for a guidewire having a thinner diameter.
• the toughening polymer can be a polymer or co-polymer selected to provide structural strength and integrity to the top coating layer.
• the toughening polymer is selected from: (poly(benzyl methacrylate), poly(butyl methacrylate), poly(tert-butyl methacrylate), poly(cyclohexyl methacrylate), poly(ethyl methacrylate), poly(tetrahydrofurfuryl methacrylate) and poly(methyl methacrylate).
• the toughening polymer is an acrylate polymer, i.e., comprising polymerized monomers including acrylate or methacrylate monomers, each of which may be alkylated or unalkylated.
• the acrylate polymer is a poly(methacrylate), i.e., comprising polymerized unalkylated or alkylated methacrylate monomers.
• the poly(methacrylate) is a poly(methyl methacrylate), i.e., comprising a polymerized monomer having the structure:
• x is between about 20 and about 30,000.
• the poly(methyl methacrylate) has a molecular weight of between about 2,000 and about 3,000,000 g/mol.
• Poly(methyl methacrylate), also referred to hereinafter as PMMA, used in accordance with the described embodiments can be a homopolymer or alternatively modified with other comonomers such as acrylates and alkyl acrylates.
• Other modifications that may be suitable for use in this application are also contemplated by the present disclosure, as will be recognized by those of skill in the art with the aid of said disclosure.
• the lubricity of the coating can be related to the hydrophilicity of the coating as a whole, or more particularly the top coating layer, or still more particularly to the hydrophilicity of one or more polymer components of top coating layer.
• n is between about 840 and about 12,900. In additional embodiments, the molecular weight is between about 130,000 and about 3,000,000 g/mol.
• the maleic acid salt monomers are optionally converted to divalent salts as in Formulas 6 and 7:
• the inclusion of a plurality of components in the top coating layer provides for coatings having selected levels of certain properties by selecting the ratio of amounts of the components.
• various ratios of lubricative polymer to toughening polymer included in the top coating layer of the coatings described herein can provide coatings having different levels of lubricity and durability.
• the weight ratio of the toughening polymer to the lubricative polymer in the top coating layer is between about 0.001 :100 and about 4:100, or between about 0.1 :100 to about 2:100. Other ratios can also be used.
• the weight fractions of lubricative polymer and toughening polymer in the top coating layer can be selected by incorporating polymer chains of each of having chain lengths or molecular weights within selected ranges.
• the molecular weight of the toughening polymer e.g., PMMA
• the molecular weight of the lubricative polymer is between about 130,000 and about 3,000,000 g/mol, or between about 1 ,250,000 and about 2,500,000 g/mol. Other molecular weights can also be used.
• the components of the top coating layer can exhibit an arrangement within that layer that also contributes to the physical and chemical properties of the coating.
• the component polymers form one or more polymer chain networks within the top coating layer.
• only certain components of the top coating layer are chemically bound or otherwise directly adhered to the underlying base coating layer.
• other components can form a network that is interpenetrating or semi- interpenetrating with the polymers attached to the base coating layer.
• the lubricative polymer is bound to the base coating layer.
• FIG. 1 shows a representation of the various polymer components in an illustrative embodiment of a coating 100 comprising PMMA as the toughening polymer 110 and a poly(methyl vinyl ether-co-maleic anhydride) as the lubricative polymer 108.
• the lubricative polymer chains 108 are chemically bound to the underlying polyurethane base coating layer 106, which is disposed on a polyurethane-tungsten jacket 104 of a medical device, while the PMMA polymer chains 110 form a semi-interpenetrating polymer network with the poly(methyl vinyl ether-co-maleic anhydride) 108.
• the top coating layer can optionally further comprise a crosslinker.
• a crosslinker It will be recognized by those of skill in the art with the aid of the present disclosure that a number of approaches and agents may be suitably employed to provide crosslinking in polymeric material. Available crosslinkers that establish crosslinking under a wide variety of stimuli including but not limited to, light, pH, temperature, hydration, and various chemical agents.
• the crosslinker can form links between crosslinkable moieties in one or more of the component polymers in the top coating layer.
• the crosslinker forms links between crosslinkable moieties in the lubricative polymer, such that the lubricative polymer is at least partially crosslinked.
• the crosslinker is an alkoxylated polyol.
• the crosslinker is trimethylolpropane ethoxylate. Other crosslinkers can also be used.
• the crosslinker is selected to form links with functional groups other than those that contribute to the hydrophilicity of the coating.
• a crosslinker may be used that forms crosslinks with moieties in the other monomers, leaving any maleic acid carboxylate groups free to form salts.
• the top coating layer has a thickness of from about 1 pm to about 15 pm, and more particularly from about 1 pm to about 5 pm, from about 5 pm to about 15 pm, or from about 2 pm to about 10 pm.
• the thickness of the base coating layer can be selected so as to be suitable for the dimensions of the medical device that is coated with the coating.
• FIGS. 2A-2C show cross-sectional views of a guidewire, which is one an example of a medical device 200 that can be coated as disclosed herein.
• the medical device 200 comprises an elongate body 202 having an exterior surface on or over which the coating is disposed.
• the medical device is jacketed, i.e., at least a portion of the exterior surface is covered with a jacket coating 204.
• Certain medical devices 200, particularly catheters, guidewires and the like, are manufactured with jacket coating 204 designed to provide a measure of hydrophilicity.
• the jacket coating 204 may be impregnated with materials such as tungsten or barium to confer a level of radiopacity, which aids the use of real-time imaging to guide placement of the device in a subject's body.
• the medical device 200 has a jacket coating 204 comprising polyurethane.
• the jacket coating 204 comprises polyurethane impregnated with a radiopaque material, such as tungsten.
• the top coating layer formulation further includes one or more solvents.
• the solvent can be selected based on its ability to solubilize the polymeric materials, as well as its suitability for the coating process to be used. In some embodiments, a combination of solvents may be used due to the respective characteristics of the plurality of polymer components in the top coating layer formulation.
• the curing step is performed to cause binding of one or more polymer components to the base coating layer.
• curing results in binding of the lubricative polymer to the base coating layer.
• the curing step comprises heating the top coating layer formulation on the base coating layer for a time and at a temperature to achieve these endpoints. While not wishing to be bound to a particular theory, such a curing step at elevated temperatures promotes the breakdown of hydrogen bonds in the polyurethane of the base coating layer, which facilitates a reaction between the polyurethane and particular monomers in the lubricative polymer.
• an activating solution to convert acid anhydride monomers to salt monomers includes a base, and optionally an alcohol.
• the activating solution has a pH of from about 9 and about 14.
• an activating solution to convert acid anhydride monomers to sodium salt monomers includes sodium hydroxide, ethanol, and water.
• activation is performed by dipping, spraying, rinsing or other suitable means of contacting the coating with the activating solution.
• the coating is dipped in the activating solution for from about 1 minute to about 30 minutes, or more particularly from about 1 minute to about 10 minutes, or from about 3 minutes to about 15 minutes, or from about 10 minutes to about 30 minutes, or from about 2 minutes to about 5 minutes.
• Example 1 The lubricity of various coatings was tested by varying the ratio of a toughening polymer (PMMA) to a lubricative polymer (poly(methyl vinyl ether-co-maleic anhydride)) in the top coating layer of a medical device. In doing so, six polyurethane- tungsten jacketed nitinol wires were first coated with a base layer comprising an aliphatic polyether-based polyurethane (2.5% w/v in THF).
• PMMA toughening polymer
• a lubricative polymer poly(methyl vinyl ether-co-maleic anhydride)
• Samples I and J were subjected to a wear/durability test using an OakRiver Technology DL1000 lubricity/wear tester. In doing so, the pads of the tester were covered with woven gauze before the wire was tested. Initially high grip force was applied and then the wire was pulled with a specific speed. The parameters of the test were as follows: test distance (100 mm); cycles (60); speed (10 mm/s); acceleration (200 mm/s) grip force (900 g); environment (PBS 1 x, 37°C). The results of the wear/durability are depicted in FIG. 6. [0057] As shown in FIG.
• Any methods disclosed herein include one or more steps or actions for performing the described method.
• the method steps and/or actions may be interchanged with one another.
• the order and/or use of specific steps and/or actions may be modified.
• sub-routines or only a portion of a method described herein may be a separate method within the scope of this disclosure. Stated otherwise, some methods may include only a portion of the steps described in a more detailed method.

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• 2021
  • 2021-05-20 US US17/326,041 patent/US12104136B2/en active Active
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