Hydrophobic acrylic intraocular lens materials

1. A copolymeric ophthalmic device material formed by polymerizing a mixture comprising

a) 40-80% (w/w) or more of an aryl acrylic hydrophobic monomer of formula (I)

wherein:

A is H;

B is (CH 2 ) m , S(CH 2 ) u , O(CH 2 ) v , or [O(CH 2 ) 2 ] n ;

u is 1-4;

v is 1-4;

C is (CH 2 ) w ;

m is 1-6;

n is 1-10;

Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH 2 ) m ;

R is H, CH 3 , C n H 2n+1 (n=1-10), iso-OC 3 H 7 , C 6 H 5 , or CH 2 C 6 H 5 ;

w is 0-6, provided that m+w≦8; and

D is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 6 H 5 , CH 2 C 6 H 5 , Br, F, Cl, or I;

b) 0.1-3.9% (w/w) of a macromer of formula (II)

wherein

R 1 and R 2 are independently —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , —C 6 H 5 , —CH 2 C 6 H 5 , —CH 2 CH 2 C 6 H 5 , —CH 2 CH 2 CH 2 C 6 H 5 , or —CH 2 CH 2 CH 2 CH 2 C 6 H 5 ;

R 3 is H, CH 3 , or CH 2 CH 3 ;

z is 2-11; and

x indicates the number of repeating units and determines the molecular weight of the macromer and is such that the macromer has a molecular weight of about 300-about 3500;

c) 5-30% (w/w) of a siloxane monomer of formula (III)

wherein

R 4 is H or CH 3 ;

T is nothing, O(CH 2 ) b , or OCH 2 CH(OH)CH 2 ;

b is 1-3;

J is (CH 2 ) z ; and

K 1 , K 2 , and K 3 independently are CH 3 , C 6 H 5 , or OSi(CH 3 );

d) 5-30% (w/w) of a hydrophilic monomer selected from the group consisting of: hydroxy(C 2 -C 4 alkyl)methacrylates, glycerol methacrylate, and N-vinyl pyrrolidone;

e) a cross-linking monomer; and

f) a reactive UV absorber;

wherein the copolymeric ophthalmic device material has an equilibrium water content at 35° C. of less than 4%.

2. The copolymeric device material of claim 1 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of: benzyl acrylate; 2-phenylethyl acrylate; 2-phenoxyethyl acrylate; 4-phenylbutyl acrylate; 5-phenylpentyl acrylate; 2-benzyloxyethyl acrylate; 3-benzyloxypropyl acrylate; 3-phenylpropyl acrylate; 3-phenoxypropyl acrylate; 2-(phenylthio)propyl acrylate; and 2-(phenylthio)ethyl acrylate.

3. The copolymeric device material of claim 2 wherein the aryl acrylic hydrophobic monomer is selected from the group consisting of: 2-phenylethyl acrylate; 2-phenoxyethyl acrylate; benzyl acrylate; and 2-(phenylthio)ethyl acrylate.

4. The copolymeric device material of claim 1 wherein the mixture comprises 40-74% (w/w) of the aryl acrylic hydrophobic monomer.

5. The copolymer device material of claim 4 wherein the mixture comprises 50-72% (w/w) of the aryl acrylic hydrophobic monomer.

6. The copolymeric device material of claim 1 wherein the mixture comprises 1-3% (w/w) of the macromer of formula (II).

7. The copolymeric device material of claim 6 wherein the mixture comprises 1.5-2.5% (w/w) of the macromer of formula (II).

8. The copolymeric device material of claim 1 wherein the macromer of formula (II) has a molecular weight of 350-2,000.

9. The copolymeric device material of claim 8 wherein the macromer of formula (II) has a molecular weight of 800-1,400.

10. The copolymeric device material of claim 8 wherein the macromer of formula (II) has a molecular weight of 550-700.

11. The copolymeric device material of claim 1 wherein the mixture comprises 5-25% (w/w) of the siloxane monomer of formula (III).

12. The copolymeric device material of claim 11 wherein the mixture comprises 5-15% (w/w) of the siloxane monomer of formula (III).

13. The copolymeric device material of claim 1 wherein the hydrophilic monomer is a hydroxy(C 2 -C 4 alkyl)methacrylate and the mixture comprises 10-20% (w/w) of the hydrophilic monomer.

14. The copolymeric device material of claim 13 wherein the hydrophilic monomer is 2-hydroxyethyl methacrylate and the mixture comprises 13-20% (w/w) of the hydrophilic monomer.

15. The copolymeric device material of claim 1 wherein the mixture comprises 0.5-10% (w/w) of the cross-linking agent.

16. The copolymeric device material of claim 15 wherein the mixture comprises 1-3% (w/w) of the cross-linking agent and the cross-linking agent is selected from the group consisting of: 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; and their corresponding acrylates.

17. The copolymeric device material of claim 16 wherein the cross-linking agent is selected from the group consisting of 1,4-butanediol dimethacrylate and triethylene glycol dimethacrylate.

18. The copolymeric device material of claim 1 wherein the mixture further comprises a reactive blue-light absorbing compound.

19. An intraocular lens comprising the copolymeric device material of claim 1 .