IP Library Granted Patent US 8,967,799
Granted Patent B2
US 8,967,799 · App. 13/722,073 · Granted Mar 3, 2015

Method of preparing water extractable silicon-containing biomedical devices

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Quick Facts
Patent No.
US 8,967,799
App. No.
13/722,073
Granted
Mar 3, 2015
Kind
B2
Abstract

A method of preparing a water extractable silicon-containing biomedical device is disclosed. The method involves curing a monomer mixture comprising one or more silicon-containing biomedical device-forming monomers in the presence of a diluent to produce a silicon-containing biomedical device; wherein the diluent comprises a boric acid ester of a C 1 to C 8 monohydric alcohol.

Claims (28)

1. A method of preparing a water extractable silicon-containing biomedical device comprising; curing a monomer mixture in a mold, the monomer mixture comprising one or more silicon-containing biomedical device-forming monomers in the presence of a diluent to produce a silicon-containing biomedical device; wherein the diluent comprises a boric acid ester of a C 1 to C 8 monohydric alcohol; and dry releasing the silicon-containing biomedical device from the mold.

2. The method of claim 1 , wherein the silicon-containing biomedical device-forming monomer is a silicon-containing monomer containing one or more Si—O units.

3. The method of claim 1 , wherein the monomer mixture further comprises a hydrophilic monomer, hydrophobic monomer or both.

4. The method of claim 3 , wherein the hydrophilic monomer is selected from the group consisting of an unsaturated carboxylic acid, vinyl lactam, acrylamide, polymerizable amine, vinyl carbonate, vinyl carbamate, oxazolone monomer and mixtures thereof.

5. The method of claim 3 , wherein the hydrophilic monomer is selected from the group consisting of methacrylic and acrylic acids, 2-hydroxyethylmethacrylate, N-vinylpyrrolidone, methacrylamide, N,N-dimethylacrylamide and mixtures thereof.

6. The method of claim 3 , wherein the hydrophobic monomer is 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, and mixtures thereof.

7. The method of claim 3 , wherein the hydrophobic monomer is selected from the groups consisting of an ethylenically unsaturated polymerizable fluorine-containing monomer, ethylenically unsaturated polymerizable fatty acid ester-containing monomer, ethylenically unsaturated polymerizable ethylenically unsaturated polymerizable monomer having ring-opening reactive functionalities, and mixtures thereof.

8. The method of claim 1 , wherein the monomeric mixture comprises two or more silicon-containing biomedical device-forming monomer which are silicon-containing monomer containing one or more Si—O units, and one or more hydrophilic units.

9. The method of claim 1 , wherein the C 1 to C 8 monohydric alcohol of the boric acid ester is selected from the group consisting of C 1 to C 8 straight or branched chain monohydric alcohols, C 5 to C 8 cycloalkyl monohydric alcohols, C 5 to C 8 aromatic monohydric alcohols and mixtures thereof.

10. The method of claim 9 , wherein the C 1 to C 8 monohydric alcohol of the boric acid ester is selected from the group consisting of methanol, ethanol, propanol, n-propanol, iso-propanol, n-butanol, t-butanol, isobutanol, 2-ethylhexanol, 2-methylcyclohexanol, 2- methyl-1-propanol, n-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, 3,7-dimethyl-3-octanol, 2,2-dimethyl-1-propanol, 1-hexanol, 1-octanol, 2-octanol, cyclohexanol, cyclopentanol, benzyl alcohol, and mixtures thereof.

11. The method of claim 1 , wherein the boric acid ester of a C 1 to C 8 monohydric alcohol is trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, or tri-tert-butyl borate.

12. The method of claim 1 , wherein the monomer mixture comprises about 5 to about 50 percent by weight of the boric acid ester of a C 1 to C 8 monohydric alcohol, based on the total weight of the monomer mixture.

13. The method of claim 1 , wherein the monomer mixture comprises about 15 to about 30 percent by weight of the boric acid ester of a C 1 to C 8 monohydric alcohol, based on the total weight of the monomer mixture.

14. The method of claim 1 , further comprising the step of replacing the diluent with water.

15. The method of claim 14 , wherein the silicon-containing biomedical device is a silicon hydrogel.

16. The method of claim 1 , further comprising lathing the silicon-containing biomedical device.

17. The method of claim 1 , wherein the mold is a one-piece mold having a concave bottom surface.

18. The method of claim 1 , wherein the mold comprises a first mold section having a molding surface shaped to provide a posterior biomedical device surface and a second mold section having a molding surface shaped to provide an anterior biomedical device surface.

19. The method of claim 18 , further comprising de-capping the first mold section from the second mold section and dry releasing the silicon-containing biomedical device from either the first mold section or the second mold section.

20. The method of claim 1 , further comprising contacting the silicon-containing biomedical device with a solvent.

21. The method of claim 20 , wherein the solvent is a polar solvent.

22. The method of claim 21 , wherein the polar solvent is water.

23. The method of claim 21 , wherein the polar solvent is an alcohol.

24. The method of claim 1 , wherein the silicon-containing biomedical device is an ophthalmic lens.

25. The method of claim 24 , wherein the ophthalmic lens is a contact lens.

26. A method for dry releasing a silicon-containing biomedical device from a mold, the method comprising the steps of:

(a) curing a monomer mixture in a mold under conditions sufficient to polymerize the monomer mixture to produce a water extractable silicon-containing biomedical device, wherein the monomer mixture comprises one or more silicon-containing biomedical device-forming monomers and a diluent; wherein the diluent comprises a boric acid ester of a C 1 to C 8 monohydric alcohol; and

(b) dry releasing the silicon-containing biomedical device from the mold.

Assignments (21)
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 039380/0385) Recorded Oct 26, 2022
From: BARCLAYS BANK PLC
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 061775/0128 →
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 →
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 →