Shape memory polymer intraocular lenses

Patent metadata

Field	Value
Publication number	US-10286107-B2
Application number	US-201615157290-A
Country	US
Kind code	B2
Filing date	May 17, 2016
Priority date	Mar 7, 2011
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

A shape memory polymer (SMP) intraocular lens may have a refractive index above 1.45, a Tg between 10° C. and 60° C., inclusive, de minimis or an absence of glistening, and substantially 100% transmissivity of light in the visible spectrum. The intraocular lens is then rolled at a temperature above Tg of the SMP material. The intraocular device is radially compressed within a die to a diameter of less than or equal to 1.8 mm while maintaining the temperature above Tg. The compressed intraocular lens device may be inserted through an incision less than 2 mm wide in a cornea or sclera or other anatomical structure. The lens can be inserted into the capsular bag, the ciliary sulcus, or other cavity through the incision. The SMP can substantially achieve refractive index values of greater than or equal to 1.45.

First claim

What is claimed is:

1. An intraocular lens (IOL) comprising a shape memory polymer (SMP), wherein the SMP is derived from a formulation comprising:
50-85 wt % tert-butyl acrylate (tBA);
3-25 wt % of one or more poly(ethylene glycol) dimethacrylate (PEGDMA) monomers having a number average molecular weight (M n ) ranging from 500 g/mol to 2,000 g/mol; and
0.25-1.5 wt % of one or more UV-blockers;
the IOL having:
a refractive index above 1.45;
a Tg between 10° C. and 60° C., inclusive;
de minimis or an absence of glistening; and
substantially 100% transmissivity of light in the visible spectrum.

2. The IOL of claim 1 , wherein the formulation further comprises 0.05-3.0 wt % of one or more polymerization initiators.

3. The IOL of claim 1 , wherein the formulation further comprises n-butyl acrylate (nBA).

4. The IOL of claim 1 , wherein the formulation further comprises 2-hydroxy-3-phenoxypropyl acrylate (HPPA).

5. The IOL of claim 1 , wherein the formulation further comprises:
0.05-3.0 wt % of one or more polymerization initiators;
nBA; and
HPPA.

6. The IOL of claim 1 , wherein the PEGDMA is selected from the group consisting of:
PEGDMA 550;
PEGDMA 750;
PEGDMA 1000;
PEGDMA 2000; and
any combination thereof.

7. The IOL of claim 1 , wherein the PEGDMA is PEGDMA 750.

8. The IOL of claim 1 , wherein the PEGDMA is PEGDMA 1000.

9. The IOL of claim 1 , wherein the one or more UV-blockers are selected from the group consisting of:
a methacryloyl chlorobenzotriazole;
a methacryloyl methoxybenzotriazole;
a yellow dye; and
any combination thereof.

10. The IOL of claim 1 , wherein the UV-blocker is selected from the group consisting of:
2-methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester (UVB); and
2-(2-hydroxy-3-tert-butyl-5-vinylphenyl)-5-chloro-2H-benzotriazole (UVAM).

11. The IOL of claim 1 , wherein the UV-blocker is 3-(tert-butyl)-4-hydroxy-5-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenethyl methacrylate.

12. The IOL of claim 2 , wherein the one or more polymerization initiators are selected from the group consisting of:
2,2-dimethoxy-2-phenylacetophenone (Irgacure 651);
phenylbis(2,4,6-trimethylbenzoyl) phosphine oxide (Irgacure 819);
azobisisobutyronitrile (AIBN);
lauroyl peroxide;
di(4-tert-butylcyclohexyl) peroxydicarbonate (Perkadox 16);
camphorquinone;
diphenyl-(2,4,6-trimethylbenzoyl)-phosphine oxide (TPO); and
any combination thereof.

13. The IOL of claim 2 , wherein the polymerization initiator is lauroyl peroxide.

14. The IOL of claim 2 , wherein the polymerization initiator includes a photo initiator and a thermal initiator.

15. An intraocular lens (IOL) comprising a shape memory polymer (SMP), wherein the SMP is derived from a formulation selected from the group consisting of SMP208, SMP209, SMP210, SMP211, SMP212, SMP213, SMP214, SMP215, SMP218, SMP219, and SMP230b, wherein:
SMP208 comprises tBA (77.5%), UVB (0.5%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP209 comprises tBA (77.0%), UVB (1.0%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP210 comprises tBA (76.0%), UVB (2.0%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP211 comprises tBA (77.5%), UVAM (0.5%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP212 comprises tBA (77.0%), UVAM (1.0%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP213 comprises tBA (76.0%), UVAM (2.0%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP214 comprises tBA (77.3%), UVB (0.7%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP215 comprises tBA (77.45%), UVAM (0.55%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP218 comprises tBA (64.30%), nBA (13.0%), UVB (0.7%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%);
SMP219 comprises tBA (64.45%), nBA (13.0%), UVAM (0.55%), PEGDMA 1000 (22%), and IRGACURE819 (0.15%); and
SMP230b comprises tBA (59.80%), nBA (12.00%), UVB (0.80%), PEGDMA 1000 (10%), lauroyl peroxide (0.15%), and HPPA (17.50%);
wherein UVB is 2-methylacrylic acid 3-(3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester, UVAM is 2-(2-hydroxy-3-tert-butyl-5-vinylphenyl)-5-chloro-2H-benzotriazole (UVAM), and IRGACURE819 is phenylbis(2,4,6-trimethylbenzoyl) phosphine oxide,
the IOL having:
a refractive index above 1.45;
a Tg between 10° C. and 60° C., inclusive:
de minimis or an absence of glistening; and
substantially 100% transmissivity of light in the visible spectrum.

16. The IOL of claim 5 , wherein the formulation comprises:
59.80 wt % tBA;
12.00 wt % nBA;
17.50 wt % HPPA;
0.70 wt % 2-methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester (UVB);
10 wt % PEGDMA 1000; and
0.15 wt % of a polymerization initiator, wherein the polymerization initiator is lauroyl peroxide.

17. A method of implanting an intraocular lens, comprising:
making an incision in a cornea or sclera less than 2 mm wide; and
inserting the intraocular lens according to claim 1 into the capsular bag through the incision;
wherein the intraocular lens is implanted in a compressed and deformed configuration.

18. A method of implanting an intraocular lens comprising:
making an incision in a cornea or sclera less than 2 mm wide; and
inserting the intraocular lens according to claim 1 into the ciliary sulcus through the incision;
wherein the intraocular lens is implanted in a compressed and deformed configuration.

19. A method of implanting an intraocular lens device comprising
making an incision into a cornea less than 2 mm wide to access the anterior chamber, and
inserting the intraocular lens according claim 1 into the anterior chamber through the incision;
wherein the intraocular lens device is implanted in a compressed and deformed configuration.

20. An intraocular lens (IOL) comprising a shape memory polymer (SMP), wherein the SMP is derived from a formulation comprising:
50-85 wt % tert-butyl acrylate (tBA);
3-25 wt % of one or more poly(ethylene glycol) dimethacrylate (PEGDMA) monomers having a number average molecular weight (M n ) ranging from 500 g/mol to 2,000 g/mol;
n-butyl acrylate (nBA); and
2-hydroxy-3-phenoxypropyl acrylate (HPPA),
the IOL having:
a refractive index above 1.45;
a Tg between 10° C. and 60° C., inclusive;
de minimis or an absence of glistening; and
substantially 100% transmissivity of light in the visible spectrum.

21. The IOL of claim 20 , wherein the formulation comprises about 5 wt %, about 10 wt %, about 15 wt %, or about 20 wt % nBA.

22. The IOL of claim 20 , wherein the formulation comprises about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, or 15 wt % to 20 wt % HPPA.

23. The IOL of claim 20 , wherein the PEGDMA is selected from the group consisting of: PEGDMA 550;
PEGDMA 750;
PEGDMA 1000;
PEGDMA 2000; and
any combination thereof.

24. The IOL of claim 20 , wherein the PEGDMA is PEGDMA 750.

25. The IOL of claim 20 , wherein the PEGDMA is PEGDMA 1000.

26. A method of implanting an intraocular lens, comprising:
making an incision in a cornea or sclera less than 2 mm wide; and
inserting the intraocular lens according to claim 20 into the capsular bag through the incision;
wherein the intraocular lens is implanted in a compressed and deformed configuration.

27. A method of implanting an intraocular lens comprising:
making an incision in a cornea or sclera less than 2 mm w

Assignees

• Univ Colorado Regents

Inventors

• Kahook Malik Y
• Mandava Naresh
• Shandas Robin
• Rech Bryan
• Lowery Michael D
• Urbaniak Daniel

Classifications

• B29L2031/7532

  Artificial members, protheses · CPC title

• A61F2002/169053

  Segments fold · CPC title

• B29C61/06

  Making preforms having internal stresses, e.g. plastic memory · CPC title

• A61F2/14

  Eye parts, e.g. lenses or corneal implants; Artificial eyes · CPC title

• A61F2/142

  Cornea, e.g. artificial corneae, keratoprostheses or corneal implants for repair of defective corneal tissue · CPC title