IP Library Granted Patent US 7,582,704
Granted Patent B2
US 7,582,704 · App. 11/173,703 · Granted Sep 1, 2009

Biomedical devices

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 7,582,704
App. No.
11/173,703
Granted
Sep 1, 2009
Kind
B2
Abstract

Biomedical devices formed from a polymerization product of a monomeric mixture comprising one or more monomers comprising at least two trifluorovinyl groups are provided. Also provided are biomedical devices formed from a network of a polymer comprising one or more perfluorocyclobutane rings in the polymer backbone wherein the network is formed by crosslinks in the polymer.

Claims (31)

1. An ophthalmic lens formed from a network of a polymer comprising one or more perfluorocyclobutane groups in the polymer backbone wherein the network is formed by crosslinks in the polymer.

2. The ophthalmic lens of claim 1 , wherein the crosslinked polymer is a polymerization product of a monomeric mixture comprising one or more monomers comprising at least three trifluorovinyl groups.

3. The ophthalmic lens of claim 1 , wherein the crosslinked polymer is a polymerization product of a monomeric mixture comprising one or more monomers comprising at least three trifluorovinyl ether groups.

4. The ophthalmic lens of claim 1 , wherein the crosslinked polymer is a polymerization product of a monomeric mixture comprising one or more monomers comprising at least three trifluorovinyl aromatic ether groups.

5. The ophthalmic lens of claim 1 , wherein the crosslinked polymer is a polymerization product of a monomeric mixture comprising one or more monomers of the general formula

F 2 C═CF—X—R 5 —(X—CF═CF 2 ) m

wherein R 5 represents one or more inertly substituted groups; X is independently a group which links the inertly substituted groups and the trifluorovinyl group and m is an integer of 2 to about 1000.

6. The ophthalmic lens of claim 5 , wherein R 5 comprises a substituted or unsubstituted cyclic or polycyclic containing group optionally containing one or more heteroatoms or a substituted or unsubstituted cyclic or polycyclic siloxane containing group; X is independently a bond, an oxygen atom, a sulfur atom, a carboxylic or thiocarboxylic ester group, an amide group, a sulfone, a sulfoxide, a carbonate, a carbamate, a perfluoroalkylene, a perfluoroalkylene ether, an alkylene, an acetylene, a phosphine, a carbonyl or thiocarbonyl group; seleno; telluro; nitrido; a silanediyl group, a trisilanedjyl group, a tetrasilanetetrayl group, a siloxanediyl group, a disiloxanediyl group, a trisiloxyldiyl group, a trisilazanyl group, a silythio group, or a boranediyl group and m is from 2 to about 10.

7. The ophthalmic lens of claim 5 , wherein each X is O and R 5 is an aromatic group selected from the group consisting of

wherein R is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, a C 1 -C 20 alkoxy group, CO 2 − , SO 3 − , PO 3 − , OPO 3 2− , F, Br, I, NA 2 or NA 3 + wherein A is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, or a C 1 -C 20 alkoxy group, or two R groups together with the carbon atom to which they are bonded are joined together to form a cyclic structure optionally containing one or more heterocyclic groups; R 2 is a bond, a C 1 -C 20 alkylene or haloalkylene group optionally containing ether or ester linkages and m is from 1 to about 10 and wherein each X group may independently be bonded to the aromatic group either ortho, meta and/or para with respect to one another.

8. The ophthalmic lens of claim 1 , wherein the crosslinked polymer is a polymerization product of a monomeric mixture comprising one or more monomers of the general formula:

wherein R 3 is independently hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 3 -C 30 cycloalkenyl, a substituted or unsubstituted C 5 -C 30 aryl, a substituted or unsubstituted a C 5 -C 30 arylalkyl, a substituted or unsubstituted C 5 -C 30 heteroaryl, a substituted or unsubstituted C 3 -C 30 heterocyclic ring, a substituted or unsubstituted C 4 -C 30 heterocycloalkyl, or a substituted or unsubstituted C 6 -C 30 heteroarylalkyl; X′ is independently a bond, an oxygen atom, a sulfur atom, a carboxylic or thiocarboxylic ester group, a sulfone, a sulfoxide, perfluoroalkylene, perfluoroalkylene ether, alkylene, acetylene, a phosphine, a carbonyl or thiocarbonyl group; seleno; telluro; nitrido; a silanediyl group, a trisilanediyl group, a tetrasilanetetrayl group, a siloxanediyl group, a disiloxanediyl group, a trisiloxyl group, a trisilazanyl group, a silythio group, or a boranediyl group; a is from 3 to about 100; and T is the same or different and is of the general formula:

wherein R 4 is independently one or more inertly substituted groups; X is independently a group which links the inertly substituted groups and the trifluorovinyl group and L is an optional linking group and is independently a straight or branched C 1 -C 30 alkylene group, a C 3 -to C 30 cycloalkylene group, a C 5 -C 3O aryl group, an ether group, a C 1 -C 20 ester group, an amide group, a siloxanyl, an arylsiloxanyl or a fluorosiloxanyl.

9. The ophthalmic lens of claim 8 , wherein X′ and X are O, R 3 is a substituted or unsubstituted straight or branched C 1 -C 30 alkyl, and R 4 is an aromatic group selected from the group consisting of

wherein R is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, a C 1 -C 20 alkoxy group, CO 2 − , SO 3 − , PO 3 − , OPO 3 2− , F, Br, I, NA 2 or NA 3 + wherein A is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, or a C 1 -C 20 alkoxy group, or two R groups together with the carbon atom to which they are bonded are joined together to form a cyclic structure optionally containing one or more heterocyclic groups; R 2 is a bond, a C 1 -C 20 alkylene or haloalkylene group optionally containing ether or ester linkages and m is from 1 to about 10 and wherein the X group and either the L group or Si atom may independently be bonded to the aromatic group either ortho, meta and/or para with respect to one another.

10. The ophthalmic lens of claim 5 , wherein the monomeric mixture further comprises one or more prepolymers having one or more trifluorovinyl groups.

11. The ophthalmic lens of claim 10 , wherein the prepolymers are selected from the group consisting of poly(siloxane) prepolymers, poly(alkyl ether) prepolymers, poly(aromatic ether) prepolymers, poly(perfluorocyclobutane) prepolymers, copolymers thereof and mixtures thereof.

12. The ophthalmic lens of claim 5 , wherein the monomeric mixture further comprises one or more poly(siloxane) prepolymers of the general formula:

wherein n and p are independently integers from 1 to about 1000; o is an integer from 1 to about 1000; R 7 independently represents one or more inertly substituted groups; X is independently a group which links the inertly substituted groups and the trifluorovinyl group; R 8 is independently an amide group, a C 1 -C 20 ester group, an ether group, an ureido, a substituted or unsubstituted C 3 -C 30 cyclicalkyl, or a C 1 -C 30 alkylene or haloalkylene group optionally containing ether or ester linkages; and R 9 , R 10 , R 11 and R 12 are independently hydrogen, a straight or branched C 1 -C 30 alkyl group, a C 1 -C 30 fluoroalkyl group, one or more substituted or unsubstituted aromatic groups, a C 1 -C 20 ester group, an ether group, an ureido group, an amide group, an amine group, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 3 -C 30 cycloalkylalkyl, a substituted or unsubstituted C 3 -C 30 cycloalkenyl, a substituted or unsubstituted C 5 -C 30 aryl, a substituted or unsubstituted C 5 -C 30 arylalkyl, a substituted or unsubstituted C 5 -C 30 heteroaryl, a substituted or unsubstituted C 3 -C 30 heterocyclic ring, a substituted or unsubstituted C 4 -C 30 heterocyclylalkyl, a substituted or unsubstituted C 6 -C 30 heteroarylalkyl, fluorine, a vinyl group, a C 5 -C 30 fluoroaryl, or a hydroxyl.

13. The ophthalmic lens of claim 12 , wherein each X is O and each R 7 is an aromatic group selected from the group consisting of

wherein R is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 2 carboxylic acid group, a C 1 -C 20 ester group, a C 1 -C 20 alkoxy group, CO 2 − , SO 3 − , PO 3 − , OPO 3 2− , F, Br, I, NA 2 or NA 3 + wherein A is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, or a C 1 -C 20 alkoxy group, or two R groups together with the carbon atom to which they are bonded are joined together to form a cyclic structure optionally containing one or more heterocyclic groups; and R 2 is a bond, a C 1 -C 20 alkylene or haloalkylene group optionally containing ether or ester linkages and wherein the X and R 8 groups may independently be bonded to the aromatic group either ortho, meta and/or para with respect to one another.

14. The ophthalmic lens of claim 8 , wherein the monomeric mixture further comprises one or more prepolymers having one or more trifluorovinyl groups.

15. The ophthalmic lens of claim 14 , wherein the prepolymers are selected from the group consisting of poly(siloxane) prepolymers, poly(alkyl ether) prepolymers, poly(aromatic ether) prepolymers, poly(perfluorocyclobutane) prepolymers, copolymers thereof and mixtures thereof.

16. The ophthalmic lens of claim 8 , wherein the monomeric mixture further comprises one or more poly(siloxane) prepolymers of the general formula:

wherein n and p are independently integers from 1 to about 1000; o is an integer from 1 to about 1000; R 7 independently represents one or more inertly substituted groups; X is independently a group which links the inertly substituted groups and the trifluorovinyl group; R 8 is independently an amide group, a C 1 -C 20 ester group, an ether group, an ureido, a substituted or unsubstituted C 3 -C 30 cyclicalcyl, or a C 1 -C 30 alkylene or haloalkylene group optionally containing ether or ester linkages; and R 9 , R 10 , R 11 and R 12 are independently hydrogen, a straight or branched C 1 -C 30 alkyl group, a C 1 -C 30 fluoroalkyl group, one or more substituted or unsubstituted aromatic groups, a C 1 -C 20 ester group, an ether group, an ureido group, an amide group, an amine group, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 3 -C 30 cycloalkylalkyl, a substituted or unsubstituted C 3 -C 30 cycloalkenyl, a substituted or unsubstituted C 5 -C 30 aryl, a substituted or unsubstituted C 5 -C 30 arylalkyl, a substituted or unsubstituted C 5 -C 30 heteroaryl, a substituted or unsubstituted C 3 -C 30 heterocyclic ring, a substituted or unsubstituted C 4 -C 30 heterocyclylalkyl, a substituted or unsubstituted C 6 -C 30 heteroarylalkyl, fluorine, a vinyl group, a C 5 -C 30 fluoroaryl, or a hydroxyl.

17. The ophthalmic lens of claim 16 , wherein each X is O and R 7 is an aromatic group selected from the group consisting of

wherein R is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, a C 1 -C 20 alkoxy group, CO 2 SO 3 − , PO 3 − , OPO 3 2− , F, Br, I, NA 2 or NA 3 + wherein A is independently hydrogen, a C 1 -C 20 alkyl group, a hydroxyl group, a C 1 -C 20 carboxylic acid group, a C 1 -C 20 ester group, or a C 1 -C 20 alkoxy group, or two R groups together with the carbon atom to which they are bonded are joined together to form a cyclic structure optionally containing one or more heterocyclic groups; and R 2 is a bond, a C 1 - C 20 alkylene or haloalkylene group optionally containing ether or ester linkages and wherein the X and R 8 groups may independently be bonded to the aromatic group either ortho, meta and/or para with respect to one another.

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

19. The ophthalmic lens of claim 18 , wherein the contact lens is a rigid gas permeable lens.

20. The ophthalmic lens of claim 18 , wherein the contact lens is a soft, hydrogel lens.

21. The ophthalmic lens of claim 18 , wherein the contact lens is a soft, non-hydrogel lens.

Assignments (9)
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 Nov 12, 2009
From: WP PRISM INC.; BAUSCH & LOMB INCORPORATED; B&L CRL, INC; B&L CRL PARTNERS L.P.; B & L DOMESTIC HOLDINGS CORP.; B&L FINANCIAL HOLDINGS CORP.; B&L SPAF INC.; B&L VPLEX HOLDINGS, INC.; BAUSCH & LOMB CHINA, INC.; BAUSCH & LOMB INTERNATIONAL INC.; BAUSCH & LOMB REALTY CORPORATION; BAUSCH & LOMB SOUTH ASIA, INC.; BAUSCH & LOMB TECHNOLOGY CORPORATION; IOLAB CORPORATION; RHC HOLDINGS INC.; SIGHT SAVERS, INC.; WILMINGTON MANAGEMENT CORP.; WILMINGTON PARTNERS L.P.; B&L MINORITY DUTCH HOLDINGS LLC; EYEONICS, INC.
To: CREDIT SUISSE, AS ADMINISTRATIVE AGENT
Reel/Frame 023510/0078 →
SECURITY AGREEMENT Recorded Nov 16, 2007
From: BAUSCH & LOMB INCORPORATED; B&L CRL INC.; B&L CRL PARTNERS L.P.; B & L DOMESTIC HOLDINGS CORP.; B&L FINANCIAL HOLDINGS CORP.; B&L SPAF INC.; B&L VPLEX HOLDINGS, INC.; BAUSCH & LOMB CHINA, INC.; BAUSCH & LOMB INTERNATIONAL INC.; BAUSCH & LOMB TECHNOLOGY CORPORATION; BAUSCH & LOMB REALTY CORPORATION; BAUSCH & LOMB SOUTH ASIA, INC.; SIGHT SAVERS, INC.; WILMINGTON MANAGEMENT CORP.; WILMINGTON PARTNERS L.P.; B&L MINORITY DUTCH HOLDINGS LLC; IOLAB CORPORATION; RHC HOLDINGS, INC.; WP PRISM, INC.
To: CREDIT SUISSE
Reel/Frame 020122/0722 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2005
From: SCHORZMAN, DEREK; SALAMONE, JOSEPH C.
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 016726/0277 →