# US 8,541,498 B2 · Lubricious coatings for medical devices > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,498 B2 - Document ID: US8541498B2 - Status: Granted - Kind: B2 - Application number: 12/877,233 - Filed: 2010-09-08 - Published: 2012-03-08 - Granted: 2013-09-24 - Earliest claimed: 2010-09-08 - Assignees: BioInteractions Ltd. - Applicants: Shivpal S. Sandhu; Alan Rhodes; Simon Jon Onis - Inventors: Shivpal S. Sandhu; Alan Rhodes; Simon Jon Onis - Web page: https://patentgrep.com/patent/US8541498B2 ## CPC - A61L 27/34: Macromolecular materials - A61L 29/085: {Macromolecular materials} - A61L 31/10: Macromolecular materials - C09D 133/062: {Copolymers with monomers not covered by C09D133/06} - A61L 2400/10: Materials for lubricating medical devices - A61N 1/056: {Transvascular endocardial electrode systems} - 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) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B) ## Abstract Substrates may be coated with copolymers of N-vinyl pyrrolidinone and aryl ketones. Processes are described for making the copolymers at high molecular weight with the ketones randomly dispersed on the copolymer. ## Claims ### Claim 1 A coating on a medical device comprising a hydrophilic layer comprising copolymers covalently crosslinked by photoinitiation of diaryl ketones pendant on the copolymers, with the copolymers, before photoinitiation, being polymerized from a plurality of monomers comprising N-vinyl pyrrolidinone and diaryl ketone vinyl monomer, having a weight average molecular weight of more than about 100,000, at least about 60% by weight N-vinyl pyrrolidinone, no more than about 5% by weight of diaryl ketone monomer that provides the pendant diaryl ketones, and a random distribution of the diaryl ketones, wherein the coating has a friction coefficient of no more than about 0.2. ### Claim 2 (depends on 1) The coating of claim 1 wherein the diaryl ketone is benzophenone. ### Claim 3 (depends on 1) The coating of claim 1 wherein the diaryl ketone monomer comprises a methacrylate group or an acrylate group. ### Claim 4 (depends on 1) The coating of claim 1 wherein the diaryl ketone of the copolymers is selected from the group consisting of 2-hydroxybenzophenone, 3-hydroxybenzophenone, 4-hydroxybenzophenone, 2,2′-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, 3,4-dihydroxybenzophenone, 4,4′-dihydroxybenzophenone, 2,3,4-trihydroxybenzophenone, 2,4,4′-trihydroxybenzophenone, 2,2′,4,4′-tetrahydroxybenzophenone, 2-aminobenzophenone, 3-aminobenzophenone, 4-aminobenzophenone, 3 ,4-diaminobenzophenone, 4,4′-diamonibenzophenone, 4-(bromomethyl)benzophenone, 2-benzoylbenzoic acid, 3-benzoylbenzoic acid, 4-benzoylbenzoic acid, 4-benzoylbenzoyl chloride, 4-isocyanatobenzophenone, benzophenone-3,3′,4,4′-tetracarboxylic dianhydride, 3-bromo-2′,5-dichloro-2-hydroxybenzophenone, 2-hydroxy-2′,3,5-trichlorobenzophenone, 3-bromo-5-chloro-2-hydroxybenzophenone, 5-bromo-2′-chloro-2-hydroxybenzophenone, 4′-chloro-5-fluoro-2-hydroxybenzophenone, 2′,5-dichloro-2-hydroxybenzophenone, 5-bromo-2-hydroxybenzophenone, 4-fluoro-4′-hydroxybenzophenone, 2-amino-4′-bromobenzophenone, 2-amino-5-chlorobenzophenone, 4-amino-3-nitrobenzophenone, 2′-chloro-2-hydroxy-4-methylbenzophenone, 2′-chloro-2-hydroxy-5-methylbenzophenone, 2-hydroxy-5-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-amino-4-methylbenzophenone, benzoin, 4,4′-dimethoxybenzoin, 4-chlorobenzoin, benzyl 4-hydroxyphenyl ketone, benzyl 2,4-dihydroxyphenyl ketone, 2-phenyl-2′,4′,6′-trihydroxyacetophenone. ### Claim 5 (depends on 1) The coating of claim 1 wherein the diaryl ketone monomer comprises a polymerizable group selected from the group consisting of acrylate groups, methacrylate groups, and methylmethacrylate groups. ### Claim 6 (depends on 1) The coating of claim 1 wherein the plurality of monomers further comprises one or more monomers selected from the group consisting of poly(ethylene glycol) methacrylate, poly(propylene glycol) methacrylate, poly(ethylene glycol) methyl ether methacrylate, poly(ethylene glycol) ethyl ether methacrylate, 3-trimethoxysilyl propyl methacrylate, vinyl sulfonic acid (sodium salt), ammonium sulfatoethyl methacrylate, 2-acryloylamido-2-methylpropanesulfonic acid monomer, [2-(methacryloyloxy)ethyl] dimethyl-(3-sulfopropyl)ammonium hydroxide (MEDSAH), [3-(methacryloylamino)propyl]dimethyl-(3-sulfopropyl)ammonium hydroxide (MPDSAH), 2-methacryloyloxyethyl phopshorylcholine (MPC), acrylic acid (sodium salt), dimethylaminoethyl methacrylate, 2-hydroxyethyl methacrylate (HEMA), polyhexanide methacrylate and chlorhexidine methacrylate. ### Claim 7 (depends on 1) The coating of claim 1 wherein the plurality of monomers further comprises a monomer that comprises a polyethylene glycol pendant group. ### Claim 8 (depends on 1) The coating of claim 1 wherein the plurality of monomers further comprises a monomer that comprises a pendant group terminating in a sulfonate group. ### Claim 9 (depends on 1) The coating of claim 1 wherein the plurality of monomers further comprises a monomer that comprises a silyl pendant group. ### Claim 10 (depends on 1) The coating of claim 1 wherein the plurality of monomers further comprise a monomer that comprises a zwitterionic group. ### Claim 11 (depends on 1) The coating of claim 1 wherein the plurality of monomers further comprise a monomer that comprises a hydroxyl group. ### Claim 12 (depends on 1) The coating of claim 1 wherein the copolymers, before photoinitiation, consist essentially of the polymerization product of the N-vinyl pyrrolidinone and the diaryl ketone monomer. ### Claim 13 (depends on 1) The coating of claim 1 wherein the medical device is selected from the group consisting of a stent, a guidewire, a pacemaker lead, a catheter, a medical balloon, a nasogastric feeding tube, and an endotracheal tube. ### Claim 14 (depends on 1) The coating of claim 1 wherein the monomers comprise an n-alkyl methacrylate monomer. ### Claim 15 (depends on 14) The coating of claim 14 wherein the n-alkyl methacrylate monomer is butyl methacrylate and the monomers comprise methoxypolyethylene glycol methacrylate. ### Claim 16 A coating on a medical device comprising a hydrophilic layer comprising copolymers covalently crosslinked by photoinitiation of diaryl ketones pendant on the copolymers, with the copolymers, before photoinitiation, being polymerized from a plurality of monomers comprising N-vinyl pyrrolidinone and diaryl ketone vinyl monomer, having a weight average molecular weight of more than about 100,000, at least about 60% by weight N-vinyl pyrrolidinone, no more than about 5% by weight of diaryl ketone monomer that provides the pendant diaryl ketones, and a random distribution of the diaryl ketones, wherein the copolymers, before photoinitiation, consist essentially of the polymerization product of the N-vinyl pyrrolidinone and the diaryl ketone monomer. ### Claim 17 A coating on a medical device comprising a hydrophilic layer comprising copolymers covalently crosslinked by photoinitiation of diaryl ketones pendant on the copolymers, with the copolymers, before photoinitiation, being polymerized from a plurality of monomers comprising N-vinyl pyrrolidinone and diaryl ketone vinyl monomer, having a weight average molecular weight of more than about 100,000, at least about 60% by weight N-vinyl pyrrolidinone, no more than about 5% by weight of diaryl ketone monomer that provides the pendant diaryl ketones, and a random distribution of the diaryl ketones, wherein the plurality of monomers comprises a monomer that comprises a pendant group chosen from the group consisting of polyethylene glycol, a silyl pendant group, a zwitterionic group, a hydroxyl group, and a pendant group terminating in a sulfonate group. ### Claim 18 (depends on 17) The coating of claim 17, wherein the coating has a friction coefficient of no more than about 0.2. ### Claim 19 (depends on 17) The coating of claim 17 wherein the diaryl ketone is benzophenone. ### Claim 20 (depends on 17) The coating of claim 17 wherein the diaryl ketone monomer comprises a polymerizable group selected from the group consisting of acrylate groups, methacrylate groups, and methylmethacrylate groups. ### Claim 21 (depends on 17) The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the polyethylene glycol pendant group. ### Claim 22 (depends on 17) The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the pendant group terminating in a sulfonate group. ### Claim 23 (depends on 17) The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the silyl pendant group. ### Claim 24 (depends on 17) The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the zwitterionic group. ### Claim 25 (depends on 17) The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the hydroxyl group. ### Claim 26 (depends on 17) The coating of claim 17 wherein the medical device is selected from the group consisting of a stent, a guidewire, a pacemaker lead, a catheter, a medical balloon, a nasogastric feeding tube, an endotracheal tube a PICC line, and a surface exposed to blood. ### Claim 27 A coating on a medical device comprising a hydrophilic layer comprising copolymers covalently crosslinked by photoinitiation of diaryl ketones pendant on the copolymers, with the copolymers, before photoinitiation, being polymerized from a plurality of monomers comprising N-vinyl pyrrolidinone and diaryl ketone vinyl monomer, having a weight average molecular weight of more than about 100,000, at least about 60% by weight N-vinyl pyrrolidinone, no more than about 5% by weight of diaryl ketone monomer that provides the pendant diaryl ketones, and a random distribution of the diaryl ketones, wherein the medical device is selected from the group consisting of a stent, a guidewire, a pacemaker lead, a catheter, a medical balloon, a nasogastric feeding tube, an endotracheal tube a PICC line, and a surface exposed to blood. ### Claim 28 (depends on 27) The coating of claim 27, wherein the coating has a friction coefficient of no more than about 0.2. ### Claim 29 (depends on 27) The coating of claim 27 wherein the diaryl ketone is benzophenone. ### Claim 30 (depends on 27) The coating of claim 27 wherein the diaryl ketone monomer comprises a polymerizable group selected from the group consisting of acrylate groups, methacrylate groups, and methylmethacrylate groups. ### Claim 31 (depends on 27) The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a polyethylene glycol pendant group. ### Claim 32 (depends on 27) The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a pendant group terminating in a sulfonate group. ### Claim 33 (depends on 27) The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a silyl pendant group. ### Claim 34 (depends on 27) The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a zwitterionic group. ### Claim 35 (depends on 27) The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a hydroxyl group. ### Claim 36 (depends on 27) The coating of claim 27 wherein the monomers comprise an n-alkyl methacrylate monomer. ### Claim 37 (depends on 36) The coating of claim 36 wherein the n-alkyl methacrylate monomer is butyl methacrylate and the monomers comprise methoxypolyethylene glycol methacrylate.