Hydrophilic polymeric coatings for medical articles with visualization moiety
View Patent ↗The invention is directed to medical device coatings, such as coated guidewires and catheters, containing a visualization moiety providing color to the coating in ambient or applied light. The coating allows for visual or machine inspection of coating properties such as uniformity of coverage. In some embodiments the coatings include the visualization moiety and an activated UV photogroup, which is used to provide covalent bonding in the coating. The visualization moiety can be in particulate form and entrained in the coating, or can be covalently bonded to the hydrophilic polymer backbone. In other embodiments the visualization moiety includes a stilbene chemical group. Exemplary coatings include a hydrophilic vinyl pyrrolidone polymer, which can provide lubricity to the device surface, along with the colored properties.
1. A medical device having a coating, the coating a polymeric matrix comprising
a hydrophilic polymer, an ultraviolet light-activated aryl ketone photogroup providing covalent bonding in the coating and covalently bonded to the hydrophilic polymer, and a visualization moiety pendent from the hydrophilic polymer,
wherein the hydrophilic polymer is covalently crosslinked to other hydrophilic polymers, covalently crosslinked to a coating material that is different than the hydrophilic polymer, covalently bonded to a surface of the medical article, or combinations thereof, and
wherein the visualization moiety comprises a fluorophore that provides color under visible light, or can be induced to provide color.
2. The device of claim 1 wherein the fluorophore comprises coumarin, coumarin-3-carboxylic acid, 7-hydroxycoumarin, 7-hydroxycoumarin-3-carboxylic acid, calcofluor white (fluorescent brightener 28), DAPI, AMCA, Lysotracker blue, Hoechst 33258, dansyl chloride, fluorescamine, fluorescein, or rhodamine.
3. The device of claim 1 wherein the visualization moiety is made pendent from the hydrophilic polymer by reacting an amine group on the hydrophilic polymer with an amine-reactive group on the visualization moiety.
4. The device of claim 1 wherein the ultraviolet light-activated aryl ketone photogroup is pendent from the hydrophilic polymer.
5. The medical device of claim 4 , wherein the hydrophilic polymer is formed by a process comprising polymerizing a monomer composition comprising an UV-activatable aryl ketone photogroup-derivatized monomer.
6. The device of claim 1 wherein the hydrophilic polymer comprises vinylpyrrolidone.
7. The device of claim 1 wherein the hydrophilic polymer comprises aminopropylmethacrylamide (APMA).
8. The device of claim 1 wherein the UV light-activatable aryl ketone photogroup is present on a compound of formula I:
X 1 —Y—X 2
where Y is a radical containing at least one acidic group, basic group, or a salt of an acidic group or basic group, and X 1 and X 2 are each independently the UV light-activatable aryl ketone photogroup.
9. The device of claim 1 which is a cardiovascular catheter or an endoscopic sheath.
10. The medical device of claim 1 , wherein the hydrophilic polymer is covalently crosslinked to a coating material that is different than the hydrophilic polymer, wherein the coating material that is different than the hydrophilic polymer is a basecoat.
11. The medical device of claim 1 , wherein the hydrophilic polymer is covalently crosslinked to a coating material that is different than the hydrophilic polymer, wherein the coating material that is different than the hydrophilic polymer is a homopolymer or copolymer that does not have a pendent UV-activatable aryl ketone photogroup.
12. A method for forming the coating of claim 1 comprising steps of
(a) providing a composition comprising a hydrophilic polymer comprising a pendent visualization moiety, wherein the visualization moiety comprises a fluorophore that provides color under visible light, or can be induced to provide color;
(b) providing a UV light-activatable aryl ketone photoreactive moiety that is present in the composition, pre-immobilized on a surface of a device, or pendent from the hydrophilic polymer;
(c) disposing the composition on a surface of a device; and
(d) treating the composition on a surface of a device to cause formation of a hydrophilic polymeric of the coating wherein the aryl ketone photoreactive moiety is covalently bonded to the hydrophilic polymer in the coating.