Biological Polysiloxanes

• US 20090276042A1
• Filed: 05/03/2007
• Published: 11/05/2009
• Est. Priority Date: 05/03/2006
• Status: Abandoned Application

• Current Assignee: Vision CRC Ltd.
• Original Assignee: Vision CRC Ltd.
• Inventors: Jeffery, Justine Leigh, Nguyen, Xuan Thi Thanh, Hughes, Timothy Charles, Wilkie, John Stuart, Hao, Xiaojuan
• Application Number:
  US12/296,998
• Publication Number:
  US 20090276042A1
• Time in Patent Office: Days
• US Class Current: 623/6.560
• 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 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to a macromonomer having a polydimethylsiloxane backbone that has a mol % dimethyl siloxanes, b mol % siloxanes substituted with -K-RIM, c mol % siloxanes substituted with -K-RIM-Z and d mol % siloxanes substituted with -L-Z, and in which the terminal siloxane groups are tri-substituted with R, wherein RIM is a refractive index modifying group; Z is a free radically polymerisable group; K is a spacer group; L is optional and is a spacer group; each R is independently selected from an RIM, a lower alkyl group, hydrogen or Z; and a is a molar percentage of the macromonomer which is in the range of from 0 to 95 mol %; b is a molar percentage of the macromonomer which is in the range of from 5 to 99 mol %; c is a molar percentage of the macromonomer which is in the range of from 0 to 2 mol %; and d is a molar percentage of the macromonomer which is in the range of from 0 to 2 mol %; with the proviso that c and d are not both 0 mol %.

Claims

1. A macromonomer of the formula I:

wherein

RIM is a refractive index modifying group;

Z is a free radically polymerisable group;

K is a spacer group;

L is optional and is a spacer group;

each R is independently selected from an RIM, a lower alkyl group, hydrogen or Z;

a is a molar percentage of the macromonomer which is in the range of from 0 to 95 mol %;

b is a molar percentage of the macromonomer which is in the range of from 5 to 99 mol %;

c is a molar percentage of the macromonomer which is in the range of from 0 to 2 mol %; and

d is a molar percentage of the macromonomer which is in the range of from 0 to 2 mol %;

with the proviso that c and d are not both 0 mol %.

2. A macromonomer according to claim 1 wherein each RIM is independently selected from the group consisting of a substituted or unsubstituted aromatic group, a fluorinated group, a group containing bromine, iodine, or chlorine atom(s) and a sulphur containing group.

3. A macromonomer according to claim 2 wherein each RIM is a substituted or unsubstituted phenyl ring.

4. A macromonomer according to claim 1 wherein each Z is an ethylenically unsaturated group.

5. A macromonomer according to claim 1 wherein each K is independently selected from the group consisting of a linear, branched, or cyclic lower alkyl, which is optionally interrupted by one or more heteroatoms or substituted by one or more of an ester, amide, urethane, carbonate, thioester or —

C(S)—

NH—

.

6. A macromonomer according to claim 5 wherein each K is a lower alkyl of the formula —

(CH₂)n-, wherein n is an integer 1, 2, 3, 4 or 5.

7. A macromonomer according to claim 1 wherein each L is a lower alkyl of the formula —

(CH₂)n-, wherein n is an integer 1, 2, 3, 4 or 5.

8. A macromonomer according to claim 1 having a refractive index at 37°

C. is in the range of from greater than 1.33 to 1.60.

9. A macromonomer according to claim 1 having a viscosity at 25°

C. of less than 150,000 cSt.

10. A macromonomer according to claim 1 having, when cured into a polymer, a modulus at 37°

C. of less than 50 kPa.

11. A composition curable into a biomedical device including a macromonomer according to claim 1.

13. An in situ curable, accommodating intraocular lens formed from the composition of claim 11.

14. A method of producing in situ an intraocular lens including the steps of introducing a composition according to claim 11 into a lens capsular bag and curing the composition.

12. (canceled)

15. (canceled)