Low-tack, hydrophobic ophthalmic device materials

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

a) 70% (w/w) or more of an aryl acrylic hydrophobic monomer of the formula

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) 0.8-2.5% (w/w) of an acryloxy-terminated poly(ethylene glycol)-polydimethylsiloxane-poly(ethylene glycol) ABA block copolymer of formula 1:

wherein

R 1 is H or CH 3 ;

x is 5-10;

y is 3; and

a is 5-15;

c) 5-30% (w/w) of a siloxane monomer of formula 2:

wherein

R 2 is H or CH 3 ;

G is nothing, O(CH 2 ) z , or OCH 2 CH(OH)CH 2 ;

z 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 ) 3 ;

d) 2-20% (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.

2. The copolymeric ophthalmic device material of claim 1 wherein the copolymeric device material has an equilibrium water content at 35° C. of less than 4%.

3. 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.

4. The copolymeric device material of claim 3 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.

5. The copolymeric device material of claim 1 wherein for the siloxane monomer of formula 2 R 2 is CH 3 , G is nothing or OCH 2 CH(OH)CH 2 , J is (CH 2 ) 3 , and K 1 , K 2 , and K 3 independently are CH 3 , C 6 H 5 , or OSi(CH 3 ) 3 .

6. The copolymeric device material of claim 5 wherein the siloxane monomer of formula 2 is selected from the group consisting of:

3-[tris(trimethylsilyloxy)silyl]-propyl methacrylate;

3-(methacryloxy-2-hydroxypropoxy)propylmethylbis(trimethoxy)silane;

methacryloxypropylpentamethyldisiloxane;

3-methacryloxypropylbis(trimethylsiloxy)methylsilane;

methacryloxymethyltris(trimethylsiloxy)silane;

(methacryloxymethyl)phenyl-dimethylsilane; and

(methacryloxymethyl)bis(trimethylsiloxy)methylsilane.

7. The copolymeric device material of claim 1 wherein the mixture comprises 5-25% (w/w) of the siloxane monomer of formula 2.

8. The copolymeric device material of claim 7 wherein the mixture comprises 5-15% (w/w) of the siloxane monomer of formula 2.

9. The copolymeric device material of claim 1 wherein the hydrophilic monomer is a hydroxy(C 2 -C 4 alkyl)methacrylate and the mixture comprises 5-15% (w/w) of the hydrophilic monomer.

10. The copolymeric device material of claim 9 wherein the hydrophilic monomer is 2-hydroxyethyl methacrylate and the mixture comprises 8-13% (w/w) of the hydrophilic monomer.

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

12. The copolymeric device material of claim 11 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.

13. The copolymeric device material of claim 12 wherein the cross-linking agent is selected from the group consisting of 1,4-butanediol dimethacrylate and triethylene glycol dimethacrylate.

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

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