Compositions with high refractive index and Abbe number

Patent metadata

Field	Value
Publication number	US-11795252-B2
Application number	US-202117451125-A
Country	US
Kind code	B2
Filing date	Oct 15, 2021
Priority date	Oct 29, 2020
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

Disclosed are co-polymers which are produced from reactive monomer mixtures and which have both high refractive index and a high Abbe number. These materials are well suited for use as implantable ophthalmic devices and have a refractive index which may be edited through application of energy. When used for an intraocular lens, the high refractive index allows for a thin lens which compresses to allow a small incision size.

First claim

We claim:

1. A composition made by free radical polymerization of a reactive monomer mixture comprising:
a) at least one low glass transition temperature monomer;
b) a tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate cross-linking agent; and
c) an ethylene glycol dicyclopentenyl ether (meth)acrylate;

wherein the concentration of the ethylene glycol dicyclopentenyl ether (meth)acrylate in the reactive monomer mixture excluding any diluent is greater than 80 weight percent; and
wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

2. The composition of claim 1 , wherein the reactive monomer mixture comprises the at least one low glass transition temperature monomer in an amount between about 1 and about 19 weight percent, between about 4 and about 17 weight percent, between about 6 and about 15 weight percent, or between about 8 and about 15 weight percent.

3. The composition of claim 1 , wherein the at least one low glass transition temperature monomer is a hydrophilic monomer.

4. The composition of claim 3 , wherein the hydrophilic monomer is a poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol) (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, and combinations thereof.

5. The composition of claim 1 , wherein the at least one low glass transition temperature monomer is a hydrophobic monomer.

6. The composition of claim 5 , wherein the hydrophobic monomer is a (meth)acrylate monomer selected from an aliphatic (meth)acrylate, a haloalkyl (meth)acrylate, a cycloaliphatic (meth)acrylate, an aromatic (meth)acrylate, and any combination thereof.

7. The composition of claim 6 , wherein the aliphatic (meth)acrylate is selected from ethyl acrylate, n-propyl acrylate, n-butyl acrylate, iso-butyl acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, n-decyl (meth)acrylate, iso-decyl (meth)acrylate, and any combination thereof.

8. The composition of claim 6 , wherein the hydrophobic monomer is a cycloaliphatic (meth)acrylate selected from 2-cyclohexylethyl acrylate, 3-cyclohexylpropyl acrylate, 4-cyclohexylbutyl acrylate, and any combination thereof.

9. The composition of claim 6 , wherein the hydrophobic monomer is an aromatic (meth)acrylate selected from the group consisting of 2-phenylethyl acrylate, 3-phenylpropyl acrylate, 4-phenylbutyl acrylate, 2-phenoxyethyl acrylate, 3-phenoxypropyl acrylate, 4-phenoxybutyl acrylate, and any combination thereof.

10. The composition of claim 5 , wherein the hydrophobic monomer is a hydroxy silicone monomer selected from 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propoxy)-2-hydroxypropyl methacrylate, mono-n-butyl terminated monomethacryloxypropyl terminated polydimethylsiloxane, and mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated mono-n-butyl terminated polydimethylsiloxane, and any combination thereof.

11. The composition of claim 1 , wherein the at least one low glass transition temperature monomer is a monomer whose homopolymer exhibits a glass transition temperature lower than 0° C., lower than minus 5° C. (−5° C.), lower than minus 10° C. (−10° C.), lower than minus 15° C. (−15° C.), or lower than minus 20° C. (−20° C.).

12. The composition of claim 1 , wherein the tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate cross-linking agent is tricyclo[5.2.1.0 2,6 ]decanedimethanol diacrylate.

13. The composition of claim 12 , wherein the reactive monomer mixture comprises the tricyclo[5.2.1.0 2,6 ]decanedimethanol diacrylate in an amount between about 0.5 weight percent and about 10 weight percent, about 0.5 weight percent and about 5 weight percent, or about 1 weight percent and about 4 weight percent.

14. The composition of any one of claim 1 , wherein the ethylene glycol dicyclopentenyl ether (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

15. The composition of claim 14 , wherein the reactive monomer mixture comprises the ethylene glycol dicyclopentenyl ether acrylate in an amount between about 80.1 weight percent and about 95 weight percent, between about 80.1 weight percent and about 92 weight percent, or between about 80.1 weight percent and about 90 weight percent.

16. The composition of claim 1 , wherein the reactive monomer mixture further comprises a non-cycloaliphatic cross-linking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl (meth)acrylate) terminated polydimethylsiloxanes, and any combination thereof.

17. The composition of claim 1 , wherein the reactive monomer mixture further comprises at least one hydroxyalkyl (meth)acrylate monomer selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

18. The composition of claim 1 , wherein the reactive monomer mixture further comprises at least one UV/HEV absorbing compound.

19. The composition of claim 1 , wherein the reactive monomer mixture further comprises at least one hydroxy silicone monomer.

20. The composition of claim 19 , wherein the at least one hydroxy silicone monomer comprises mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyloxy)-propyl terminated polydimethylsiloxane, 3-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propoxy)-2-hydroxypropyl methacrylate, 3-(3-(1,5-di-tert-butyl-1,1,3,5,5-pentamethyltrisiloxan-3-yl)propoxy)-2-hydroxypropyl methacrylate, or any combination thereof.

21. The composition of claim 19 , wherein the reactive monomer mixture comprises the at least one hydroxy silicone monomer in an amount between about 1 and about 25 weight percent.

22. The composition of claim 1 , having a water content of between about 0 weight percent and about 15 weight percent, about 1 weight percent and about 10 weight percent, or about 1 weight percent and about 5 weight percent.

23. The composition of claim 1 , wherein the composition has a refractive index of at least 1.45 and an Abbe number of at least 45.

24. An ophthalmic device comprising the composition of claim 1 , wherein the ophthalmic device comprises an intraocular lens, contact lens, corneal inlay, corneal onlay or corneal insert.

25. A method for making an ophthalmic device, the method comprising:
a. providing a composition of any claim 1 ; and
b. forming an ophthalmic device.

Assignees

• Johnson & Johnson Surgical Vision Inc

Inventors

• Alli Azaam
• Arnold Stephen
• Joslin Scott L
• Johnson Bart A

Classifications

• C08F220/281 Primary

  and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate · CPC title

• A61L27/16

  obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61L27/50

  Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} · CPC title

• C08L33/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title