IP Library Granted Patent US 8,071,660
Granted Patent B2
US 8,071,660 · App. 12/329,694 · Granted Dec 6, 2011

Surface modified biomedical devices

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Quick Facts
Patent No.
US 8,071,660
App. No.
12/329,694
Granted
Dec 6, 2011
Kind
B2
Abstract

A method for making a surface modified biomedical device is disclosed, the method comprising contacting a surface of a biomedical device with a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers.

Claims (25)

1. A method for making a surface modified biomedical device, the method comprising (a) providing a biomedical device having a plurality of biomedical device surface functional groups; and (b) attaching a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers to the surface of the biomedical device through the biomedical device surface functional groups.

2. The method of claim 1 , wherein the biomedical device surface functional group of the biomedical device is selected from the group consisting of a hydroxy group, amino group, carboxy group, carbonyl group, aldehyde group, sulfonic acid group, sulfonyl chloride group, isocyanato group, carboxy anhydride group, lactone group, azlactone group, epoxy group and mixtures thereof.

3. The method of claim 1 , wherein the polymerizable polyhydric alcohol is a polyhydric alcohol terminated with a polymerizable ethylenically unsaturated radical and the polymerizable fluorine-containing monomer is a fluorine-containing monomer terminated with a polymerizable ethylenically unsaturated radical.

4. The method of claim 1 , wherein the polymerizable polyhydric alcohol is selected from the group consisting of a polymerizable glycerol-containing compound, polymerizable erythritol-containing compound, polymerizable xylitol-containing compound, polymerizable sorbitol-containing compound and mixtures thereof.

5. The method of claim 1 , wherein the polymerizable polyhydric alcohol is selected from the group consisting of glycerol (meth)acrylate, erythritol (meth)acrylate, xylitol (meth)acrylate, sorbitol (meth)acrylate and mixtures thereof.

6. The method of claim 1 , wherein the polymerizable fluorine-containing monomer is a fluorinated (meth)acrylate monomer.

7. The method of claim 1 , wherein the polymerizable fluorine-containing monomer is selected from the group consisting of 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 2,2,3,3,3,-pentafluoropropyl (meth)acrylate, 1-trifluoromethyl-2,2,2-trifluoroethyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, 2,2,3,3,4,4-hexafluorobutyl (meth)acrylate and mixtures thereof.

8. The method of claim 1 , wherein the copolymer is terminated with an ethylenically unsaturated-containing radical.

9. The method of claim 1 , wherein step (b) comprises contacting the surface of the biomedical device with the copolymer under free radical polymerization conditions.

10. The method of claim 1 , wherein the biomedical device is an ophthalmic lens.

11. The method of claim 10 , wherein the ophthalmic lens is a contact lens or an intraocular lens.

12. The method of claim 1 , wherein the biomedical device is a silicone hydrogel.

13. A biomedical device comprising a bulk material having a plurality of biomedical device surface functional groups and a surface coating, in which the biomedical device is characterized by a copolymer attached to the surface of the biomedical device through the biomedical device surface functional groups, wherein the copolymer is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers.

14. The biomedical device of claim 13 , wherein the biomedical device surface functional group of the biomedical device is selected from the group consisting of a hydroxy group, amino group, carboxy group, carbonyl group, aldehyde group, sulfonic acid group, sulfonyl chloride group, isocyanato group, carboxy anhydride group, lactone group, azlactone group, epoxy group and mixtures thereof.

15. The biomedical device of claim 13 , wherein the polymerizable polyhydric alcohol is a polyhydric alcohol terminated with a polymerizable ethylenically unsaturated radical and the polymerizable fluorine-containing monomer is a fluorine-containing monomer terminated with a polymerizable ethylenically unsaturated radical.

16. The biomedical device of claim 13 , wherein the polymerizable polyhydric alcohol is selected from the group consisting of glycerol (meth)acrylate, erythritol (meth)acrylate, xylitol (meth)acrylate, sorbitol (meth)acrylate and mixtures thereof and the polymerizable fluorine-containing monomer is a fluorinated (meth)acrylate monomer.

17. The biomedical device of claim 13 , wherein the polymerizable fluorine-containing monomer is selected from the group consisting of 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 2,2,3,3,3,-pentafluoropropyl (meth)acrylate, 1-trifluoromethyl-2,2,2-trifluoroethyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, 2,2,3,3,4,4-hexafluorobutyl (meth)acrylate and mixtures thereof.

18. The biomedical device of claim 13 , wherein the copolymer is terminated with an ethylenically unsaturated-containing radical.

19. The biomedical device of claim 13 , wherein the biomedical device is an ophthalmic lens.

20. The biomedical device of claim 19 , wherein the ophthalmic lens is a contact lens or an intraocular lens.

21. The biomedical device of claim 13 , wherein the biomedical device is a silicone hydrogel.

22. A method for making a surface modified biomedical device, the method comprising contacting a surface of a biomedical device with a copolymer which is the reaction product of one or more polymerizable polyhydric alcohols and one or more polymerizable fluorine-containing monomers.

23. The method of claim 22 , wherein the polymerizable polyhydric alcohol is selected from the group consisting of glycerol (meth)acrylate, erythritol (meth)acrylate, xylitol (meth)acrylate, sorbitol (meth)acrylate and mixtures thereof and the polymerizable fluorine-containing monomer is a fluorinated (meth)acrylate monomer.

24. The method of claim 22 , wherein the copolymer is terminated with an ethylenically unsaturated-containing radical.

25. The method of claim 22 , wherein the biomedical device is an ophthalmic lens.

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
NOTICE OF SUCCESSION OF AGENCY Recorded Jan 9, 2015
From: GOLDMAN SACHS LENDING PARTNERS, LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 034749/0689 →
SECURITY AGREEMENT Recorded Sep 4, 2013
From: BAUSCH & LOMB INCORPORATED
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 031156/0508 →
RELEASE OF SECURITY INTEREST Recorded Aug 13, 2013
From: CITIBANK N.A., AS ADMINISTRATIVE AGENT
To: WP PRISM INC. (N/K/A BAUSCH & LOMB HOLDINGS INC.); BAUSCH & LOMB INCORPORATED; ISTA PHARMACEUTICALS
Reel/Frame 030995/0444 →
SECURITY AGREEMENT Recorded Aug 6, 2012
From: BAUSCH & LOMB INCORPORATED; EYEONICS, INC.
To: CITIBANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 028728/0645 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2012
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 028726/0142 →
SECURITY AGREEMENT Recorded Apr 23, 2012
From: BAUSCH & LOMB INCORPORATED
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
Reel/Frame 028090/0019 →