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.
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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
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. 2. The coating of claim 1 wherein the diaryl ketone is benzophenone. 3. The coating of claim 1 wherein the diaryl ketone monomer comprises a methacrylate group or an acrylate group. 4. 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. 5. 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. 6. 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. 7. The coating of claim 1 wherein the plurality of monomers further comprises a monomer that comprises a polyethylene glycol pendant group. 8. The coating of claim 1 wherein the plurality of monomers further comprises a monomer that comprises a pendant group terminating in a sulfonate group. 9. The coating of claim 1 wherein the plurality of monomers further comprises a monomer that comprises a silyl pendant group. 10. The coating of claim 1 wherein the plurality of monomers further comprise a monomer that comprises a zwitterionic group. 11. The coating of claim 1 wherein the plurality of monomers further comprise a monomer that comprises a hydroxyl group. 12. 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. 13. 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. 14. The coating of claim 1 wherein the monomers comprise an n-alkyl methacrylate monomer. 15. The coating of claim 14 wherein the n-alkyl methacrylate monomer is butyl methacrylate and the monomers comprise methoxypolyethylene glycol methacrylate. 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. 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. 18. The coating of claim 17, wherein the coating has a friction coefficient of no more than about 0.2. 19. The coating of claim 17 wherein the diaryl ketone is benzophenone. 20. 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. 21. The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the polyethylene glycol pendant group. 22. The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the pendant group terminating in a sulfonate group. 23. The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the silyl pendant group. 24. The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the zwitterionic group. 25. The coating of claim 17 wherein the plurality of monomers comprises the monomer that comprises the hydroxyl group. 26. 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. 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. 28. The coating of claim 27, wherein the coating has a friction coefficient of no more than about 0.2. 29. The coating of claim 27 wherein the diaryl ketone is benzophenone. 30. 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. 31. The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a polyethylene glycol pendant group. 32. The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a pendant group terminating in a sulfonate group. 33. The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a silyl pendant group. 34. The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a zwitterionic group. 35. The coating of claim 27 wherein the plurality of monomers comprises a monomer that comprises a hydroxyl group. 36. The coating of claim 27 wherein the monomers comprise an n-alkyl methacrylate monomer. 37. The coating of claim 36 wherein the n-alkyl methacrylate monomer is butyl methacrylate and the monomers comprise methoxypolyethylene glycol methacrylate.
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