IP Library Granted Patent US 8,198,375
Granted Patent B2
US 8,198,375 · App. 12/421,056 · Granted Jun 12, 2012

Trifluorovinyl aromatic containing poly(alkyl ether) prepolymers

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Quick Facts
Patent No.
US 8,198,375
App. No.
12/421,056
Granted
Jun 12, 2012
Kind
B2
Abstract

The present invention provides prepolymers based on poly(alkyl ethers) having terminal trifluorovinyl aromatic containing groups and polymers produced from such prepolymers. The prepolymers and polymers are useful as biomedical devices such as contact lenses or intraocular lenses.

Claims (23)

1. A poly(alkyl ether) polymer or copolymer containing one or more perfluorocyclobutane aromatic ether radicals in the polymer backbone.

2. The poly(alkyl ether) polymer or copolymer of claim 1 , which is a polymerization product of a monomeric mixture comprising one or trifluorovinyl aromatic ether containing poly(alkyl ether) prepolymers of the general formula T-(P) n -T wherein n is 1 to about 100,000, T is independently of the general formula

wherein L is an optional linking group and is independently a straight or branched C 1 -C 30 alkylene group, a C 3 -C 30 cycloalkylene group, a C 5 -C 30 arylene group, an ether group, a C 1 -C 20 ester group, an amide group, a siloxanyl, an arylsiloxanyl or a fluorosiloxanyl, and R 1 is the same or different and comprises a substituted or unsubstituted cyclic or polycyclic group optionally containing one or more heteroatoms; and P is independently an oxyalkylene radical of the general 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 and m is 1 to about 10.

3. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein R 1 is one or more aromatic groups 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 4 is a bond, a C 1 -C 20 alkylene or haloalkylene group optionally containing ether or ester linkages and wherein the O atom and either the L or P group may independently be bonded to the aromatic group either ortho, meta and/or para with respect one another.

4. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein R 1 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 4 is a bond, a C 1 -C 20 alkylene or haloalkylene group optionally containing ether or ester linkages and wherein the O atom and either the L or P group may independently be bonded to the aromatic group either ortho, meta and/or para with respect one another and 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.

5. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein R 2 and R 3 are independently a straight or branched C 1 -C 6 alkyl group.

6. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein R 2 and R 3 are independently a straight or branched C 1 -C 6 fluoroalkyl group.

7. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein n is 3 to about 10,000, and R 2 and R 3 are independently a straight or branched C 1 -C 6 alkyl group and the oxyalkylene units are formed as random copolymers.

8. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein n is 3 to about 10,000, R 2 and R 3 are independently a straight or branched C 1 -C 6 alkyl group and the oxyalkylene units are formed as block copolymers.

9. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein n is 3 to about 10,000, and R 2 and R 3 are independently a straight or branched C 1 -C 6 fluoroalkyl group and the oxyalkylene units are formed as random copolymers.

10. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein n is 3 to about 10,000, and R 2 and R 3 are independently a straight or branched C 1 -C 6 fluoroalkyl group and the oxyalkylene units are formed as block copolymers.

11. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein the monomeric mixture further comprises one or more crosslinking monomers and/or one or more wetting agents.

12. The poly(alkyl ether) polymer or copolymer of claim 2 , wherein the monomeric mixture further comprises one or more prepolymers selected from the group consisting of poly(siloxane) prepolymers, poly(aromatic ether) prepolymers, poly(perfluorocyclobutane) prepolymers, copolymers thereof and mixtures thereof.

13. The poly(alkyl ether) polymer or copolymer of claim 2 , which is selected from the group consisting of

wherein x, y and z are independently 0 and at least 1 with x+y+z being from 1 to equal to or less than about 10,000 and R 5 is independently hydrogen or a C 1 -C 4 alkyl group; and

wherein m and n are independently 0 and at least 1 with m+n being from 1 to equal to or less than about 10,000.

14. A biomedical device comprising the poly(alkyl ether) polymer or copolymer of claim 1 .

15. The biomedical device of claim 14 , which is an ophthalmic lens.

16. The biomedical device of claim 15 , wherein the ophthalmic lens is a contact lens.

17. The biomedical device of claim 16 , 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 →