Photocurable siloxane polymers

• US 6,737,496 B2
• Filed: 04/29/2002
• Issued: 05/18/2004
• Est. Priority Date: 10/13/1998
• Status: Expired due to Term

• Current Assignee: Advanced Medical Optics Uppsala AB (Abbott Medical Optics Norden AB)
• Original Assignee: Pharmacia Groningen BV
• Inventors: Hodd, Kenneth A., Norrby, Sverker
• Primary Examiner(s): PENG, KUO LIANG
• Application Number:
  US10/134,710
• Publication Number:
  US 20030088044A1
• Time in Patent Office: 750 Days
• Field of Search: 623/6.11, 528/32, 528/12, 528/33, 528/36, 528/43, 526/279
• US Class Current: 528/32
• CPC Class Codes: A61L 2400/06 Flowable or injectable implant compositions
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08G 77/44 containing only polysiloxane sequences
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to photocurable siloxane polymers having functional acryl groups, useful in the preparation of intraocular lenses (IOLs). The polymers are siloxane copolymers, wherein the siloxane can be selected from the group consisting of diphenyl siloxane, phenylalkyl siloxane, dialkyl siloxane, and trifluoroalkyl alkyl siloxane. The invention also relates to methods for producing the said siloxane polymers, as well as to producing accommodating lenses in vivo, which means that the lens is formed in the capsular bag of the eye.

Claims

1. A photopolymerizable polysiloxane copolymer having functional acryl groups at terminal ends thereof, a specific gravity greater than about 1.0, and a refractive index suitable for restoring the refractive power of the natural crystalline lens, wherein the polysiloxane copolymer has siloxane monomer units selected from the group consisting of substituted and unsubstituted arylsiloxanes, substituted and unsubstituted arylalkylsiloxanes, substituted and unsubstituted alkyl(alkyl)siloxanes, and mixtures thereof, wherein at least one of the siloxane monomer units is substituted with one or more fluorine atoms, and wherein at least one siloxane monomer unit is an arylsiloxane or an arylalkylsiloxane.

2. The polysiloxane copolymer according to claim 1, having a refractive index above about 1.39.

3. A polysiloxane copolymer according to claim 1, having a backbone of the general formula:

wherein R¹ and R² are independently C₁-C₆ alkyl;

R³ is phenyl;

R⁴ is phenyl or C₁-C₆ alkyl;

R⁵ is CF₃(CH₂)_x wherein x is 1-5;

R⁶ is C₁-C₆ alkyl or or fluoroalkyl;

1 is in the molar fraction range of 0 to 0.95;

m is in the molar fraction range of from greater than 0 to 0.7; and

n is in the molar fraction range of from greater than 0 to 0.65.

4. The copolymer according to claim 3, wherein R¹ is methyl.

5. The copolymer according to claim 4, wherein R² is methyl.

6. The copolymer according to claim 5, wherein R⁴ is phenyl.

7. The copolymer according to claim 3, wherein R⁴ is phenyl.

8. The copolymer according to claim 3, wherein x is 2.

9. The copolymer according to claim 6, wherein x is 2.

10. The copolymer according to claim 3, wherein R⁶ is 2 methyl.

11. The copolymer according to claim 9, wherein R⁶ is methyl.

12. The copolymer according to claim 3, wherein 1 is in the molar range of from greater than 0 to 0.95.

13. The copolymer according to claim 3, wherein the copolymer is a copolymer of diphenyl siloxane or phenylalkyl siloxane units and trifluoroalkyl alkyl siloxane units.

14. The copolymer according to claim 3, wherein the copolymer is a terpolymer or higher order copolymer of diphenyl siloxane or phenylalkyl siloxane units, dialkyl siloxane units and trifluoroalkyl alkyl siloxane units.

15. The copolymer according to claim 5, wherein the copolymer is a terpolymer of dimethyl siloxane units, diphenyl siloxane units and trifluoroalkyl methyl siloxane units.

16. The copolymer according to claim 1, having a viscosity of less than about 60,000 cSt.