# US 2014/0193474 A1 · Low particulate lubricious coating with vinyl pyrrolidone and acidic polymer-containing layers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0193474 A1 - Document ID: US20140193474A1 - Status: Published application - Kind: A1 - Application number: 14/148,339 - Filed: 2014-01-06 - Published: 2014-07-10 - Earliest claimed: 2013-01-04 - Assignees: SurModics, Inc. - Applicants: Surmodics, Inc - Inventors: DAVID E. BABCOCK; TIMOTHY M. KLOKE; JOSEPH S. MCGONIGLE - Web page: https://patentgrep.com/patent/US20140193474A1 ## CPC - A61L 29/14: Materials characterised by their function or physical properties {, e.g. lubricating compositions} - A61L 29/041: {obtained by reactions only involving carbon-to-carbon unsaturated bonds} - A61L 29/085: {Macromolecular materials} - B05D 7/54: {No clear coat specified} - C10M 107/28: containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate - C10M 107/42: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - C10M 107/46: containing sulfur - C10M 107/48: containing phosphorus - C10M 107/50: containing silicon - C10M 135/36: the ring containing sulfur and carbon with nitrogen or oxygen - C10M 169/04: Mixtures of base-materials and additives - C10M 177/00: Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes - A61L 2400/10: Materials for lubricating medical devices - A61L 2420/02: Methods for coating medical devices - A61L 2420/08: Coatings comprising two or more layers - C10M 2209/084: Acrylate; Methacrylate - C10M 2209/0845: used as base material - C10M 2217/0245: used as base material - C10M 2217/0285: used as base material - C10N 2020/01: {Physico-chemical properties} - C10N 2050/023: {Multi-layer lubricant coatings} - C10N 2050/025: {in the form of films or sheets} - Y10T 428/31573: Next to addition polymer of ethylenically unsaturated monomer - Y10T 428/31699: Ester, halide or nitrile of addition polymer - Y10T 428/3175: Next to addition polymer from unsaturated monomer[s] - Y10T 428/31928: Ester, halide or nitrile of addition polymer - 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 (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract Embodiments of the disclosure include lubricious coatings. In an embodiment the disclosure includes a lubricious coating for a medical device including first and second coated layers. The first coated layer is between the second coated layer and the device surface and includes a vinyl pyrrolidone polymer and a photo reactive group. The second coated layer is in direct contact with the first coated layer and is a top coating that includes an acrylic acid polymer. The second coated layer can optionally include photoreactive groups. The coating was found to have a very low number of particulates (e.g., 10 μm or greater) which is very desirable for in vivo use. ## Claims ### Claim 1 A lubricious coating comprising: a first coated layer comprising a vinyl pyrrolidone polymer and photoreactive groups, wherein the photoreactive groups are pendent from the vinyl pyrrolidone polymer or on a first cross-linking agent comprising at least two photoreactive groups, or both; and a second coated layer that is a top coating comprising an acrylic acid polymer, wherein the second coated layer is in direct contact with the first coated layer, wherein the first coated layer is between the second coated layer and a substrate surface. ### Claim 2 (depends on 1) The coating of claim 1 wherein the second coated layer further comprises an acrylamide polymer comprising at least one photo reactive group. ### Claim 3 (depends on 2) The coating of claim 2 wherein the acrylamide polymer comprises acrylamide-, 2-acrylamido-2-methylpropanesulfonate (AMPS)-, and poly(ethylene glycol)-containing subunits. ### Claim 4 (depends on 2) The coating of claim 2, wherein the vinyl pyrrolidone polymer and the acrylamide polymer are present in the coating at a weight ratio in the range of approximately 3:1 to 1:3 (wt./wt.), respectively. ### Claim 5 (depends on 2) The coating of claim 2, wherein the acrylic acid polymer and the acrylamide polymer are present in the coating at a weight ratio in the range of approximately 2:1 to 1:2 (wt./wt.), respectively. ### Claim 6 (depends on 1) The coating of claim 1 wherein comprising a first cross-linking agent, wherein the vinyl pyrrolidone polymer and the first cross-linking agent are present in the coating at a weight ratio in the range of about 8:1 to about 20:1 (wt./wt.). ### Claim 7 (depends on 1) The coating of claim 1 comprising a first or second cross-linking reagent, wherein at least one of the first and second cross-linking agent(s) is a compound of formula Photo1-LG-Photo2, wherein Photo1 and Photo2, independently represent at least one photoreactive group and LG represents a linking group comprising at least one silicon or at least one phosphorus atom, there is a covalent linkage between at least one photoreactive group and the linking group, wherein the covalent linkage between at least one photoreactive group and the linking group is interrupted by at least one heteroatom. ### Claim 8 (depends on 7) The coating of claim 7 at least one of the first and second cross-linking agents is a compound of formula selected from: wherein R1, R2, R8 and R9 are any substitution; R3, R4, R6 and R7 are alkyl, aryl, or a combination thereof; R5 is any substitution; and each X, independently, is O, N, Se, S, or alkyl, or a combination thereof; wherein R1 and R5 are any substitution; R2 and R4 can be any substitution, except OH; R3 can be alkyl, aryl, or a combination thereof; and each X, independently, is O, N, Se, S, alkyl or a combination thereof; wherein R1, R2, R4 and R5 are any substitution; R3 is any substitution; R6 and R7 are alkyl, aryl, or a combination thereof; and each X, independently, is O, N. Se, S, alkyl, or a combination thereof; and (d). ### Claim 9 (depends on 8) The coating of claim 8 wherein at least one of the first and second cross-linking agent(s) is sodium bis[(4-benzoylphenyl) phosphate. ### Claim 10 (depends on 1) The coating of claim 1, wherein the acrylic acid polymer has an average molecular weight of 150 kDa or greater. ### Claim 11 (depends on 1) The coating of claim 1, the coating releasing particulates of less than 3,000 particles greater than 10 microns. ### Claim 12 (depends on 1) The coating of claim 1, wherein the thickness of the first and second coated layers combined is between about 100 and 1000 nm when dry. ### Claim 13 (depends on 1) The coating of claim 1, wherein (a) the coating exhibits a lubricity when wetted of between 0 and 30 grams of force for at least 10 consecutive testing cycles, or wherein (b) the coating exhibits a durability of lubricity such there is less than a 30 percent increase in measured friction between the average of cycles 1-5 of testing and cycles 10-15 of testing, or both (a) and (b). ### Claim 14 (depends on 1) The coating of claim 1, wherein (a) the coating exhibits reduced platelet accumulation, (b) reduced fibrin accumulation, or both (a) and (b), as compared to a control coating having only the first coated layer. ### Claim 15 (depends on 14) The coating of claim 14, wherein (a) the coating exhibits reduced platelet accumulation, the reduction being greater than 20% of the control, greater than 30% of the control, greater than 40% of the control, greater than 50% of the control, greater than 60% of the control, or greater than 70% of the control, or (b) reduced fibrin accumulation, the reduction being greater than 25% of the control, greater than 50% of the control, greater than 60% of the control, greater than 70% of the control, greater than 80% of the control, or greater than 90% of the control, or both (a) and (b). ### Claim 16 (depends on 1) A medical device comprising the coating of claim 1. ### Claim 17 (depends on 16) The medical device of claim 16, wherein the substrate comprises polyamide, polyimide, polyether block amide (PEBAX), polyether ether ketone (PEEK), high density polyethylene (HDPE), polyethylene, polyurethane, or polyethylene vinyl acetate. ### Claim 18 (depends on 17) The medical device of claim 17, the medical device comprising a catheter. ### Claim 19 (depends on 16) The medical device of claim 16, the medical device comprising a metal substrate, or that is selected from the group consisting of embolic protection devices and mapping/ablation catheters. ### Claim 20 (depends on 1) The medical device of claim 1 wherein the coating further comprises a coated layer comprising an extracellular matrix protein or peptide, or a protein or peptide that provides hemocompatible or thromboresistant properties. ### Claim 21 A method making a coating on a medical device comprising: applying a first coating solution directly or indirectly on a medical device surface, the first coating solution comprising a vinyl pyrrolidone polymer and photoreactive groups, wherein the photoreactive groups are pendent from the vinyl pyrrolidone polymer or present on a first cross-linking agent comprising at least two photoreactive groups; and a first solvent, and drying the first coating solution; exposing the first coating solution to actinic radiation to form a first layer; applying a second coating solution onto the first layer, the second coating solution comprising an acrylic acid polymer, and a second solvent, and optionally a second cross-linking agent comprising at least two photoreactive groups, and drying the second coating solution; and exposing the second coating solution to actinic radiation to form a second layer. ### Claim 22 (depends on 21) The method of claim 21, wherein the first solvent comprises isopropyl alcohol (IPA) and water at a volume ratio in the range of 95:5 to 10:90 (% vol. IPA:water). ### Claim 23 (depends on 21) The method of claim 21, wherein the second solvent comprises IPA and water at a volume ratio in the range of 0:100 to 100:0 (% vol. IPA:water). ### Claim 24 (depends on 21) The method of claim 21, wherein the viscosity of the first solution, second solution, or both first and second solution is less than about 30 cP. ### Claim 25 (depends on 21) The method of claim 21 comprising use of a coating application unit comprising a movement restriction structure; a fluid applicator; an air nozzle; and a rotation mechanism; and an axial motion mechanism, the axial motion mechanism configured to cause movement of at least one of the coating application unit and the rotation mechanism with respect to one another. ### Claim 26 A method for preparing a coated device comprising extruding a composition comprising vinyl pyrrolidone polymer and a thermoplastic polymer to form an extruded surface and then coating the extruded surface with an acrylic acid polymer.