IP Library Granted Patent US 6,918,931
Granted Patent B2
US 6,918,931 · App. 10/657,639 · Granted Jul 19, 2005

Prepolymers with yellow dye moiety

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 6,918,931
App. No.
10/657,639
Granted
Jul 19, 2005
Kind
B2
Abstract

Yellow dye moiety-containing prepolymers with blue light absorbing priorities and methods for producing the same for use in the production of relatively high refractive index polymeric compositions are described herein. Polymeric compositions so produced are useful in the production of ophthalmic devices such as for example intraocular lenses and corneal inlays.

Claims (43)

1. Prepolymers comprising:

wherein the V groups may be the same or different reactive or polymerizable groups; the R 1 groups may be the same or different spacer groups, nothing or an organic spacing group; the R 2 groups may be the same or different C 1-6 alkyl groups; R 3 is either R 2 or R 4 ; R 4 is a C 6-30 aromatic group; R 5 is a yellow dye-containing moiety; the U groups may be the same or different difunctional linkage or nothing; and m, n, p and q represent the same or different non-negative integers greater than zero.

2. The prepolymer of claim 1 wherein q is an integer such that the weight of R 5 is less than approximately 5 percent of the weight of the prepolymer.

3. The prepolymer of claim 1 wherein q is an integer such that the weight of R 5 is less than approximately 1 percent of the weight of the prepolymer.

4. The prepolymer of claim 1 wherein said V groups are selected from the group consisting of vinyl, allyl, acrylate, methacrylate, acrylamide, methylacrylamide, fumarate, maleate and styrene.

5. The prepolymers of claim 1 wherein said R 1 groups are selected from the group consisting of spacer groups, nothing or an organic spacing group.

6. The prepolymers of claim 5 wherein said spacer groups are selected from the group consisting of C 1-12 alkylenes.

7. The prepolymers of claim 5 wherein said organic spacing group is composed of up to 12 atoms in any combination.

8. The prepolymers of claim 7 wherein said atoms are selected from the group consisting of carbon, hydrogen, silicon, oxygen, nitrogen, phosphorous, sulfur, chloride, bromine and fluorine.

9. The prepolymers of claim 1 wherein said R 5 group contains a yellow dye moiety.

10. The prepolymers of claim 1 wherein said U group is nothing or a difunctional linkage, which renders the prepolymer with multiple blocks of polysiloxane groups and yellow dye moieties.

11. The prepolymers of claim 1 wherein said U group is urethane.

12. The prepolymers of claim 1 wherein said prepolymers have blue light absorption properties.

13. A polymeric composition produced through the copolymerization of one or more prepolymers of claim 1 with one or more monomers or oligomers.

14. A polymeric composition produced through the copolymerization of one or more prepolymers of claim 1 with one or more monomers or oligomers, one or more strengthening agents, one or more crosslinking agents and one or more catalysts.

15. The polymeric composition of claim 13 or 14 wherein said one or more monomers or oligomers are selected from the group consisting of high refractive index siloxane-containing acrylates, high refractive index siloxane-containing methacrylates, aromatic-group-containing acrylates, aromatic-group-containing methacrylates, vinyl- or allyl-containing siloxane monomers having high refractive indices, and vinyl or allyl-containing aromatic monomers.

16. The polymeric composition of claim 14 wherein said strengthening agent is selected from a group consisting of a silica filler and a siloxane-based resin with at least one vinyl group.

17. The polymeric composition of claim 14 wherein said strengthening agent is a silica filler.

18. The polymeric composition of claim 14 wherein said strengthening agent is a siloxane-based resin with at least one vinyl groups.

19. The polymeric composition of claim 14 wherein said crosslinking agent is polydimethyl- co -methylhydrosiloxane.

20. The polymeric composition of claim 14 wherein said catalyst is a Pt-silicone complex.

21. The polymeric composition of claim 14 wherein said catalyst is Pt-silicone complex.

22. A process for producing the prepolymers of claim 1 comprising:

linking one or more yellow dye moiety-containing compounds with one or more polysiloxane compounds to produce a prepolymer intermediate; and

reacting said prepolymer intermediate with an ethylenically unsaturated monomer containing a functional group.

23. A process for producing a polymeric composition comprising:

polymerizing one or more prepolymers of claim 1 with one or more monomers or oligomers.

24. A process for producing a polymeric composition comprising:

polymerizing one or more prepolymers of claim 1 with one or more monomers or oligomers, one or more strengthening agents, one or more crosslinking agents and one or more catalysts.

25. The process of claim 23 or 24 wherein said one or more monomers or oligomers are selected from the group consisting of high refractive index siloxane-containing acrylates, high refractive index siloxane-containing methacrylates, aromatic-group-containing acrylates, aromatic-group-containing methacrylates, vinyl- or allyl-containing siloxane monomers having high refractive indices, and vinyl or allyl-containing aromatic monomers.

26. The process of claim 24 wherein said reinforcing component is selected from a group consisting of silica filler or a siloxane-based-resin with at least one vinyl groups.

27. The process of claim 24 wherein said reinforcing component is a silica filler.

28. The process of claim 24 wherein said reinforcing component is a siloxane-based resin with at least one vinyl group.

29. A method of producing an ophthalmic device using the polymeric composition produced through the process of claim 23 or 24 comprising:

casting said polymeric composition into a shaped body.

30. A method of using the ophthalmic device produced through the method of claim 29 comprising:

implanting said ophthalmic device in an eye.

31. A method of producing an ophthalmic device using a polymeric composition produced from one or more of the prepolymers of claim 1 comprising:

casting said polymeric composition into a shaped body.

32. The method of using the ophthalmic device produced through the method of claim 31 comprising:

implanting said ophthalmic device in an eye.

33. A medical device containing one or more of the prepolymers of claim 1 .

34. An intraocular lens containing one or more of the prepolymers of claim 1 .

Assignments (26)
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 →
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 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 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 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: 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 →
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 →