High refractive index, high abbe number intraocular lens materials

Patent metadata

Field	Value
Publication number	US-10712474-B2
Application number	US-201916509667-A
Country	US
Kind code	B2
Filing date	Jul 12, 2019
Priority date	Jun 5, 2017
Publication date	Jul 14, 2020
Grant date	Jul 14, 2020

Abstract

Disclosed are high refractive index, hydrophobic, acrylic materials. These materials have both high refractive index and a high Abbe number. This combination means the materials have a low refractive index dispersion and thus are especially suitable for use as intraocular lens materials. The materials are also suitable for use in other implantable ophthalmic devices, such as keratoprostheses, corneal rings, corneal implants, and corneal inlays.

First claim

I claim:

1. A polymeric ophthalmic device material made by polymerizing a mixture of monomers wherein the mixture comprises:
a) a total of 70-90 wt. % of one or more cycloaliphatic acrylic monomers of formula (I)

wherein: A is H or CH 3 ;
B is O, NR, or S;
D is O, S, or nothing;
E is CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , CH 2 OH or H;
R is H, CH 3 , CH 2 CH 3 , or CH(CH 3 ) 2 ;
x is 1-4, provided that if x is >1, then not more than one CHE group has E≠H;
y is 0-2; and
z is 0-4, provided that if D=nothing, then z≠0.

b) a total of 5-25 wt. % of one or more hydrophilic monomers selected from the group consisting of: hydroxy(C 2 -C 4 alkyl)methacrylates, glycerol methacrylate, and N-vinyl pyrrolidone; and
c) a copolymerizable cross-linking agent;
wherein the ophthalmic device material has a refractive index of 1.46-1.50 and an Abbe number greater than 47, a Tg<15° C., and an equilibrium water content of the polymerized ophthalmic device material is less than 4%.

2. The ophthalmic device material of claim 1 , wherein for the cycloaliphatic acrylic monomer of formula (I):
A is H or CH 3 ;
B is O;
D is O or nothing;
E is CH 3 or H;
x is 2-2, provided that not more than one CHE group has E=CH 3 ;
y is 0; and
z is 0-2, provided that if D=nothing, then z≠0.

3. The ophthalmic device material of claim 2 , wherein for the cycloaliphatic acrylic monomer of formula (I):
A is H or CH 3 ;
B is O;
D is nothing;
E is H;
x is 3;
y is 0; and
z is 2.

4. The ophthalmic device material of claim 1 , wherein the cycloaliphatic acrylic monomer of formula (I) is selected from the group consisting of: 2-cyclohexylethyl acrylate; 2-cyclopentylethyl acrylate; 3-cyclohexylpropyl acrylate; 3-cyclopentylpropyl acrylate; and 2-(cyclohexyloxy)ethyl acrylate.

5. The ophthalmic device material of claim 1 , wherein the mixture comprises a total of 75-85 wt. % of cycloaliphatic acrylic monomer of formula (I).

6. The ophthalmic device material of claim 5 , wherein the mixture comprises a total of 77-82 wt. % of cycloaliphatic acrylic monomer of formula (I).

7. The ophthalmic device material of claim 1 , wherein the hydrophilic monomer is a hydroxy(C 2 -C 4 alkyl)methacrylate and the mixture comprises a total of 12-22 wt. % of hydrophilic monomer.

8. The ophthalmic device material of claim 7 , wherein the hydrophilic monomer is 2-hydroxethyl methacrylate.

9. The ophthalmic device material of claim 8 , wherein the mixture comprises a total of 16-19 wt. % of 2-hydroxethyl methacrylate.

10. The ophthalmic device material of claim 1 , wherein the equilibrium water content of the polymerized ophthalmic device material is less than 2%.

11. The ophthalmic device material of claim 1 , wherein the copolymerizable cross-linking agent is a terminally ethylenically unsaturated compound having more than one unsaturated group.

12. The ophthalmic device material of claim 11 , wherein the copolymerizable cross-linking agent is selected from the group consisting of: ethylene glycol diacrylate; diethylene glycol diacrylate; allyl acrylate; 1,3-propanediol diacrylate; 2,3-propanediol diacrylate; 1,6-hexanediol diacrylate; 1,4-butanediol diacrylate; triethylene glycol diacrylate; cyclohexane-1,1-diyldimethanol diacrylate, 1,4-cyclohexanediol diacrylate, 1,3-adamantanediol diacrylate, 1,3-adamantanedimethyl diacrylate, 2,2-diethyl-1,3-propanediol diacrylate, 2,2-diisobutyl-1,3-propanediol diacrylate, 1,3-cyclohexanedimethyl diacrylate, 1,4-cyclohexanedimethyl diacrylate; neopentyl glycol diacrylate; ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; allyl methacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,4-butanediol dimethacrylate; triethylene glycol dimethacrylate; cyclohexane-1,1-diyldimethanol dimethacrylate, 1,4-cyclohexanediol dimethacrylate, 1,3-adamantanediol dimethacrylate, 1,3-adamantanedimethyl dimethacrylate, 2,2-diethyl-1,3-propanediol dimethacrylate, 2,2-diisobutyl-1,3-propanediol dimethacrylate, 1,3-cyclohexanedimethyl dimethacrylate, 1,4-cyclohexanedimethyl dimethacrylate; neopentyl glycol dimethacrylate; poly(ethylene glycol) dimethacrylate (M n =700 Daltons) and poly(ethylene glycol) dimethacrylate (M n =2000 Daltons).

13. The ophthalmic device material of claim 12 , wherein the mixture comprises 0.5-2 wt. % neopentyl glycol diacrylate.

14. The ophthalmic device material of claim 1 , wherein the mixture comprises a total of 0.5-10 wt. % of cross-linking agent.

15. The ophthalmic device material of claim 1 , wherein the mixture comprises 0.1-5 wt. % of a reactive UV absorber.

16. The ophthalmic device material of claim 1 , wherein the ophthalmic device material has an Abbe number greater than 50.

17. An ophthalmic device material made by polymerizing a mixture of monomers wherein the mixture comprises:
a) 75-85 wt. % 2-cyclohexylethyl acrylate;
b) 12-22 wt. % 2-hydroxethyl methacrylate; and
c) 1-3 wt. % of a cross-linking agent having a molecular weight of 100-500 Daltons;
wherein the ophthalmic device material has a refractive index of 1.48-1.50, an Abbe number greater than 52, a Tg<15° C., and an equilibrium water content less than 2%.

Assignees

• Novartis Ag
• Alcon Inc

Inventors

• Schlueter Douglas

Classifications

• A61L27/16 Primary

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

• G02B1/041 Primary

  Lenses · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• G02C7/108

  Colouring materials · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title