IP Library Granted Patent US 8,183,325
Granted Patent B2
US 8,183,325 · App. 12/131,434 · Granted May 22, 2012

Perfluorocyclobutane copolymers

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Quick Facts
Patent No.
US 8,183,325
App. No.
12/131,434
Granted
May 22, 2012
Kind
B2
Abstract

The present invention provides copolymer having repeating units based on polyoxyalkylene radicals, polysiloxane radicals and perfluorocyclobutane radicals. The copolymers are useful as biomedical devices such as contact lenses or intraocular lenses.

Claims (19)

1. A copolymer containing perfluorocyclobutane groups in the polymer backbone and comprising at least two of the following units;

(a) an oxyalkylene unit of the formula

wherein R 2 and R 3 are independently hydrogen, a straight or branched C 1 -C 6 alkyl group, a C 3 -C 30 cycloalkyl group, a C 5 -C 30 aryl group, a straight or branched C 1 -C 6 fluoroalkyl group, a C 3 -C 30 fluorocycloalkyl group, a C 5 -C 30 fluoroaryl group, an ether group, a C 1 -C 20 ester group, an amide group, an amine group, fluorine, a vinyl group, or a hydroxyl group, m is 1 to about 10 and n is 1 to about 100,000;

(b) a polysiloxane unit of the formula

wherein R 4 and R 5 are independently hydrogen, a straight or branched C 1 -C 6 alkyl group, a C 3 -C 30 cycloalkyl group, a C 5 -C 30 aryl group, a straight or branched C 1 -C 6 fluoroalkyl group, a C 3 -C 30 fluorocycloalkyl group, a C 5 -C 30 fluoroaryl group, an ether group, a C 1 -C 20 ester group, C 1 -C 6 alkoxy group, an amide group, an amine group, fluorine, a vinyl group, or a hydroxyl group and n is 1 to about 100,000; and

(c) a perfluorocyclobutane unit of the formula

wherein 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, R 6 independently represents one or more inertly substituted groups and n is 1 to about 100,000.

2. The copolymer of claim 1 , comprising one or more of the oxyalkylene units (a) and one or more of the perfluorocyclobutane units (c).

3. The copolymer of claim 2 , wherein in the oxyalkylene unit (a) R 2 and R 3 are independently a straight or branched C 1 -C 6 alkyl group or a straight or branched C 1 -C 6 fluoroalkyl group and the oxyalkylene units are formed as random copolymers, and in the perfluorocyclobutane unit (c) X′ is O and R 6 comprises a cyclic or polycyclic group optionally containing one or more heteroatoms.

4. The copolymer of claim 2 , wherein in the oxyalkylene unit (a) R 2 and R 3 are independently a straight or branched C 1 -C 6 alkyl group or a straight or branched C 1 -C 6 fluoroalkyl group and the oxyalkylene units are formed as block copolymers, and in the perfluorocyclobutane unit (c) X′ is O and R 6 comprises a cyclic or polycyclic group optionally containing one or more heteroatoms.

5. The copolymer of claim 1 , comprising one or more of the oxyalkylene units (a) and one or more of the polysiloxane units (b).

6. The copolymer of claim 5 , wherein in the oxyalkylene unit (a) R 2 and R 3 are independently a straight or branched C 1 -C 6 alkyl group or a straight or branched C 1 -C 6 fluoroalkyl group and wherein in the polysiloxane unit (b) R 4 and R 5 are independently a straight or branched C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group.

7. The copolymer of claim 1 , comprising one or more of the polysiloxane units (b) and one or more of the perfluorocyclobutane units (c).

8. The copolymer of claim 7 , wherein in the polysiloxane unit (b) R 4 and R 5 are independently a straight or branched C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group, and in the perfluorocyclobutane unit (c) X′ is O and R 6 comprises a cyclic or polycyclic group optionally containing one or more heteroatoms.

9. The copolymer of claim 1 , comprising one or more of the oxyalkylene unit (a), one or more of the polysiloxane units (b) and one or more of the perfluorocyclobutane units (c).

10. A biomedical device comprising the copolymer of claim 1 .

11. The biomedical device of claim 10 , which is an ophthalmic lens.

12. The biomedical device of claim 11 , wherein the ophthalmic lens is a contact lens.

13. The biomedical device of claim 12 , wherein the contact lens is a rigid gas permeable lens.

Assignments (7)
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 →
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 →
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 15, 2012
From: BAUSCH & LOMB INCORPORATED
To: CITIBANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 028788/0271 →
SECURITY AGREEMENT Recorded Aug 6, 2012
From: BAUSCH & LOMB INCORPORATED; EYEONICS, INC.
To: CITIBANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 028728/0645 →