Photocurable siloxane polymers

• US 6,399,734 B1
• Filed: 10/13/1999
• Issued: 06/04/2002
• 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 AB (Pharmacia Corp.)
• Inventors: Norrby, Sverker, Hodd, Kenneth A.
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): PENG, KUO LIANG
• Application Number:
  US09/416,773
• Time in Patent Office: 965 Days
• Field of Search: 623/6.11, 623/4.1, 522/6, 264/1-32, 528/32, 528/12, 528/18, 528/23, 528/33, 528/36
• 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 tens is formed in the capsular bag of the eye.

Claims

1. An injectable lens material having suitable viscosity for being injected through standard cannula and comprising a mixture of a polysiloxane copolymer, a photoinitiator, and, optionally, a crosslinking agent, wherein the polysiloxane copolymer is capable of being photopolymerized into a solid intraocular lens and has functional acryl groups at terminal ends of the copolymer, a specific gravity greater than about 1.0, a refractive index suitable for restoring the refractive power of the natural crystalline lens, and siloxane monomer units in the polysiloxane copolymer selected from the group consisting of substituted and unsubstituted arylsiloxanes, substituted and unsubstituted arylalkylsiloxanes, and 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. An injectable lens material according to claim 1, wherein the copolymer has a refractive index above about 1.39.

3. An injectable lens material according to claim 1, wherein the copolymer has 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 fluoroalkyl;

l 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. An injectable lens material according to claim 3, wherein R¹ is methyl.

5. An injectable lens material according to claim 4, wherein R² is methyl.

6. An injectable lens material according to claim 3, wherein R⁴ is phenyl.

7. An injectable lens material according to claim 3, wherein x is 2.

8. An injectable lens material according to claim 3, wherein R⁶ is methyl.

9. An injectable lens material according to claim 3, wherein l is in the molar fraction of greater than 0.

10. An injectable lens material according to claim 3, wherein the copolymer is a copolymer of diphenyl siloxane or phenylalkyl siloxane units and trifluoroalkyl alkyl siloxane units.

11. An injectable lens material according to claim 3, wherein the copolymer is a terpolymer or higher order copolymer of diphenyl or phenylalkyl siloxane, dialkyl siloxane and trifluoroalkyl alkyl siloxane.

12. An injectable lens material according to claim 3, wherein the copolymer is a terpolymer of dimethyl siloxane, diphenyl siloxane and trifluoropropyl methyl siloxane.

13. An injectable lens material according to claim 1, wherein the polysiloxane has a viscosity of less than about 60,000 cSt.

14. An injectable lens material having suitable viscosity for being injected through standard cannula and comprising a mixture of a polysiloxane copolymer, a photoinitiator, and, optionally, a crosslinking agent, wherein the polysiloxane copolymer has functional acryl groups at the terminal ends thereof capable of being photopolymerized into a solid intraocular lens, a specific gravity greater than about 1.0, a refractive index suitable for restoring the refractive power of the natural crystalline lens, and siloxane monomer units in the polysiloxane copolymer selected from the group consisting of substituted and unsubstituted arylsiloxanes, substituted and unsubstituted arylalkylsiloxanes, and substituted and unsubstituted alkyl(alkyl)siloxanes, and wherein the photoinitiator is activated by blue light.