IP Library Granted Patent US 8,138,290
Granted Patent B2
US 8,138,290 · App. 12/350,262 · Granted Mar 20, 2012

High water content ophthalmic devices

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Quick Facts
Patent No.
US 8,138,290
App. No.
12/350,262
Granted
Mar 20, 2012
Kind
B2
Abstract

An ophthalmic device is disclosed that is a polymerization product of a monomeric mixture comprising (a) a major amount of a non-silicone-containing hydrophilic monomer; (b) a hydrophobic monomer; and (c) a crosslinking agent, wherein the ophthalmic device has an equilibrium water content of at least about 70 weight percent and further wherein the ophthalmic device has an evaporative dehydration barrier layer on the surface thereof. A method for the mitigation of evaporative corneal dehydration employing the high water content ophthalmic device is also disclosed.

Claims (26)

1. An ophthalmic device that is a polymerization product of a monomeric mixture comprising: (a) a major amount of a non-silicone-containing hydrophilic monomer; (b) a hydrophobic monomer; and (c) a crosslinking agent, wherein the ophthalmic device has an equilibrium water content of at least about 70 weight percent and further wherein the ophthalmic device has an evaporative dehydration barrier layer on the surface thereof.

2. The ophthalmic device of claim 1 , having an equilibrium water content of at least about 80 weight percent.

3. The ophthalmic device of claim 1 , wherein the non-silicone-containing hydrophilic monomer is selected from the group consisting of an amide, cyclic lactam, poly(alkene glycols) functionalized with polymerizable groups and mixtures thereof.

4. The ophthalmic device of claim 1 , wherein the non-silicone-containing hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-vinyl-2-pyrrolidone and mixtures thereof.

5. The ophthalmic device of claim 1 , wherein the non-silicone-containing hydrophilic monomer is present in the monomeric mixture in an amount of greater than about 70 weight percent, based on the total weight of the monomeric mixture.

6. The ophthalmic device of claim 1 , wherein the non-silicone-containing hydrophilic monomer is present in the monomeric mixture in an amount of greater than about 80 weight percent, based on the total weight of the monomeric mixture.

7. The ophthalmic device of claim 1 , wherein the hydrophobic monomer is represented by the structure of Formula I:

wherein R 1 is methyl or hydrogen; R 2 is —O— or —NH—; R 3 and R 4 are independently a divalent radical selected from the group consisting of —CH 2 —, —CHOH— and —CHR 6 —; R 5 and R 6 are independently a branched C 3 -C 8 alkyl group; and n is an integer of at least 1, and m and p are independently 0 or an integer of at least 1, provided that the sum of m, p and n is 2, 3, 4 or 5.

8. The ophthalmic device of claim 1 , wherein the hydrophobic monomer is present in the monomeric mixture in an amount of about 0.5 to about 25 weight percent.

9. The ophthalmic device of claim 1 , wherein the monomeric mixture further comprises a hydrophobic silicon-containing monomer.

10. The ophthalmic device of claim 9 , wherein the hydrophobic silicon-containing monomer is O-(methacryloxyethyl)-N-(triethoxysilylpropyl)urethane.

11. The ophthalmic device of claim 9 , wherein the hydrophobic silicon-containing monomer is present in the monomeric mixture in an amount up to about 15 weight percent.

12. The ophthalmic device of claim 1 , having a dehydration rate of less than or equal to about 0.600 mg/minute.

13. The ophthalmic device of claim 9 , having a dehydration rate of less than or equal to about 0.450 mg/minute.

14. The ophthalmic device of claim 1 , wherein the ophthalmic device is a contact lens.

15. An ophthalmic device that is a polymerization product of a monomeric mixture comprising: (a) a major amount of a non-silicone-containing hydrophilic monomer; (b) a hydrophobic monomer; and (c) a crosslinking agent, wherein the ophthalmic device has an equilibrium water content of at least about 70 weight percent and further wherein the ophthalmic device has a dehydration rate of less than or equal to about 0.600 mg/minute.

16. The ophthalmic device of claim 15 , having an equilibrium water content of at least about 80 weight percent.

17. The ophthalmic device of claim 15 , wherein the non-silicone-containing hydrophilic monomer is selected from the group consisting of an amide, cyclic lactam, poly(alkene glycols) functionalized with polymerizable groups and mixtures thereof.

18. The ophthalmic device of claim 15 , wherein the monomer mixture further comprises a silicone-containing hydrophobic monomer and further wherein the ophthalmic device has a dehydration rate of less than or equal to about 0.450 mg/minute.

19. A method comprising the step of casting a monomeric mixture comprising (a) a major amount of a non-silicone-containing hydrophilic monomer; (b) a hydrophobic monomer; and (c) a crosslinking agent in a hydrophobic substrate to form an ophthalmic device having an evaporative dehydration barrier layer on the surface thereof and wherein the ophthalmic device has an equilibrium water content of at least about 70 weight percent.

20. The method of claim 19 , wherein the ophthalmic device has an equilibrium water content of at least about 80 weight percent.

21. The method of claim 19 , wherein the ophthalmic device has a dehydration rate of less than or equal to about 0.600 mg/minute.

22. The method of claim 19 , wherein the hydrophilic monomer is present in the monomeric mixture in an amount of greater than about 70 weight percent.

23. The method of claim 19 , wherein the monomeric mixture further comprises a hydrophobic silicon-containing monomer.

24. The method of claim 19 , wherein the hydrophobic substrate comprises polypropylene, polystyrene, silanized glass or a combination thereof.

25. A method for substantially mitigating evaporative corneal dehydration associated with an ophthalmic device having an equilibrium water content of at least about 70 weight percent, the method comprising contacting the surface of an eye of a subject with an ophthalmic device that is a polymerization product of a monomeric mixture comprising: (a) a major amount of a non-silicone-containing hydrophilic monomer; (b) a hydrophobic monomer; and (c) a crosslinking agent, wherein the ophthalmic device has an equilibrium water content of at least about 70 weight percent and further wherein the ophthalmic device has a dehydration rate of less than or equal to about 0.600 mg/minute.

Assignments (22)
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 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 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 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 034749/0689) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED; UNIVERSITY OF ROCHESTER
Reel/Frame 061778/0146 →
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 →
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: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 045444/0634 →
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 Jul 19, 2017
From: BAUSCH & LOMB INCORPORATED
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043251/0932 →