IP Library › Granted Patent US 8,133,960
Granted Patent B2
US 8,133,960 · App. 12/456,421 · Granted Mar 13, 2012

Biomedical devices

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Quick Facts
Patent No.
US 8,133,960
App. No.
12/456,421
Filed
Jun 16, 2009
Granted
Mar 13, 2012
Kind
B2
Art Unit
1762
USPC
526/263
Abstract

Biomedical devices such as contact lenses formed from a polymerization product of a mixture comprising (a) a random copolymer comprising hydrophilic units and hydrophobic units, wherein the random copolymer has at least one thio carbonyl thio fragment of a reversible addition fragmentation chain transfer (“RAFT”) agent are disclosed.

Claims (24)

1. A biomedical device comprising a polymerization product of a mixture comprising a random copolymer comprising hydrophilic units and hydrophobic units, wherein the random copolymer has at least one thio carbonyl thio fragment of a reversible addition fragmentation chain transfer (“RAFT”) agent.

2. The biomedical device of claim 1 , wherein the thio carbonyl thio fragment comprises a dithioester group, xanthate group, dithiocarbamate group or trithiocarbonate group.

3. The biomedical device of claim 1 , wherein the hydrophilic units are derived from a hydrophilic monomer selected from the group consisting of an unsaturated carboxylic acid, acrylamide, vinyl lactam, ethylenically unsaturated poly(alkylene oxide), (meth)acrylic acid, hydroxyl-containing-(meth)acrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomer, and mixtures thereof.

4. The biomedical device of claim 1 , wherein the hydrophilic units are derived from a hydrophilic monomer selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate and mixtures thereof.

5. The biomedical device of claim 1 , wherein the hydrophilic units are derived from an ethylenically unsaturated polymerizable alkoxylated polymer selected from the group consisting of polyethylene glycol (PEG)-200 methacrylate, PEG-400 methacrylate, PEG-600 methacrylate, PEG-1000 methacrylate and mixtures thereof.

6. The biomedical device of claim 1 , wherein the random copolymer has a number average molecular weight of about 1000 to about 300,000.

7. The biomedical device of claim 1 , wherein the random copolymer has a number average molecular weight of about 10,000 to about 100,000.

8. The biomedical device of claim 1 , wherein the hydrophobic units are derived from a hydrophobic monomer selected from the groups consisting of an ethylenically unsaturated polymerizable fluorine-containing monomer, ethylenically unsaturated polymerizable fatty acid ester-containing monomer, ethylenically unsaturated polymerizable polysiloxanylalkyl-containing monomer, ethylenically unsaturated polymerizable monomer having ring-opening reactive functionalities, ethylenically unsaturated polymerizable nitrogen protected monomer with amino functionality in which all or a portion of the amino functionality is blocked with a nitrogen protecting group, and mixtures thereof.

9. The biomedical device of claim 8 , wherein the ethylenically unsaturated 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, octafluoropentyl methacrylate, octafluoropentyl vinyl carbonate, octafluoropentyl n-vinyl carbamate, hexafluoroisopropyl(meth)acrylate, 2,2,3,3,4,4-hexafluorobutyl(meth)acrylate, pentafluorophenyl(meth)acrylate, pentafluorohexyl(meth)acrylate and mixtures thereof.

10. The biomedical device of claim 8 , wherein the ethylenically unsaturated polymerizable fatty acid ester-containing monomer is selected from the group consisting of vinyl laurate, vinyl nonanoate, vinyl pivalate, vinyl crotonate, allyl crotonate, vinyl stearate and mixtures thereof.

11. The biomedical device of claim 8 wherein the ethylenically unsaturated polymerizable polysiloxanylalkyl-containing monomer is selected from the group consisting methacryloxypropyl tris(tnmethylsiloxy)silane, (trimethylsilyl)propyl vinyl carbonate; 3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane]; 3-[tris(tri-methylsiloxy)silyl]propyl vinyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, tris(trimethylsiloxy)silylpropyl methacrylamide, M1-MCR-C12 and mixtures thereof.

12. The biomedical device of claim 9 , wherein the ethylenically unsaturated polymerizable monomer having ring-opening reactive functionalities is selected from the group consisting of glycidyl methacrylate, maleic anhydride, itaconic anhydride and mixtures thereof.

13. The biomedical device of claim 1 , wherein the hydrophobic units are derived from a hydrophobic monomer selected from the group consisting of alkyl (meth)acrylates, N-alkyl(meth)acrylamides, alkyl vinylcarbonates, alkyl vinylcarbamates, fluoroalkyl(meth)acrylates, N-fluoroalkyl(meth)acrylamides, N-fluoroalkyl vinylcarbonates, N-fluoroalkyl vinylcarbamates, silicone-containing (meth)acrylates, (meth)acrylamides, vinyl carbonates, vinyl carbamates, vinyl esters, styrenic monomers, polyoxypropylene (meth)acrylates and mixtures thereof.

14. The biomedical device of claim 1 , wherein the mixture further comprises a biomedical device-forming comonomer.

15. The biomedical device of claim 14 , wherein the biomedical device-forming comonomer is a silicone-containing monomer.

16. The biomedical device of claim 1 , wherein the mixture further comprises a hydrophilic monomer, hydrophobic monomer or both.

17. The biomedical device of claim 14 , wherein the mixture further comprises a hydrophilic monomer selected from the group consisting of an unsaturated carboxylic acid, acrylamide, vinyl lactam, poly(alkyleneoxy)(meth)acrylate, (meth)acrylic acid, hydroxyl-containing-(meth)acrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomer and mixtures thereof.

18. The biomedical device of claim 1 , wherein the mixture further comprises a hydrophilic monomer selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate and mixtures thereof.

19. The biomedical device of claim 1 , wherein the device is a contact lens.

20. The biomedical device of claim 19 , wherein the contact lens is a rigid gas permeable contact lens.

21. The biomedical device of claim 19 , wherein the contact lens is a soft contact lens.

22. The biomedical device of claim 19 , wherein the contact lens is a hydrogel contact lens.

23. The biomedical device of claim 1 , wherein the device is an intraocular lens.

24. The biomedical device of claim 1 , wherein the device is a corneal implant.

Assignments (25)
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 073637/0001 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
Reel/Frame 073637/0126 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
Reel/Frame 073654/0242 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (059913/0548) Recorded Aug 14, 2025
From: CITIBANK, N.A., AS RESIGNING AGENT
To: JPMORGAN CHASE BANK, N.A., AS SUCCESSOR AGENT
Reel/Frame 072469/0091 →
PATENT SECURITY AGREEMENT Recorded Jul 1, 2025
From: BAUSCH & LOMB INCORPORATED; ALDEN OPTICAL LABORATORIES, INC.; BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 071773/0871 →
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 →
PATENT SECURITY AGREEMENT Recorded Oct 4, 2023
From: BAUSCH & LOMB INCORPORATED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 065120/0086 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 045444/0634) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; LABORATOIRE CHAUVIN S.A.S.; TECHNOLAS PERFECT VISION GMBH; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 061872/0295 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 043251/0932) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; TECHNOLAS PERFECT VISION GMBH
Reel/Frame 061872/0099 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 048556/0758) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH COMPANIES INC.; TECHNOLAS PERFECT VISION GMBH; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 061872/0484 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 056811/0814) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061872/0669 →
OMNIBUS PATENT SECURITY RELEASE AGREEMENT (REEL/FRAME 059121/0001) Recorded Nov 2, 2022
From: THE BANK OF NEW YORK MELLON
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061873/0001 →
RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (REEL/FRAME 045444/0299) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED; TECHNOLAS PERFECT VISION GMBH; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; PF CONSUMER HEALTHCARE 1 LLC; LABORATOIRE CHAUVIN S.A.S.
Reel/Frame 061779/0001 →
RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (REEL/FRAME 031156/0508) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061778/0446 →
RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (REEL/FRAME 034749/0689) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED; UNIVERSITY OF ROCHESTER
Reel/Frame 061778/0146 →
PATENT SECURITY AGREEMENT Recorded May 10, 2022
From: BAUSCH & LOMB INCORPORATED
To: CITIBANK, N.A. AS COLLATERAL AGENT
Reel/Frame 059913/0548 →
SECURITY AGREEMENT Recorded Feb 10, 2022
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 059121/0001 →
SECURITY INTEREST Recorded Jun 8, 2021
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 056811/0814 →
SECURITY INTEREST Recorded Mar 11, 2019
From: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 048556/0758 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 045444/0299 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 045444/0634 →
SECURITY INTEREST Recorded Jul 19, 2017
From: BAUSCH & LOMB INCORPORATED
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043251/0932 →
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 →