High refractive index, acrylic ophthalmic device materials with reduced glistenings

1. A polymeric ophthalmic or otorhinolaryngological device material comprising

a) 50-93% of a polymerizable monomer of the structure:

wherein: A is H or CH 3 ;

B is (CH 2 ) m or [O(CH 2 ) 2 ] z ;

m is 2-6;

z 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 , iso-OC 3 H 7 , C 6 H 5 , or CH 2 C 6 H 5 ;

n′=1-10;

w is 0-6, provided that m+w≦8; and

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

b) 1-5% of a high molecular weight, linear polyethylene glycol component of the structure:

wherein: X, X′ independently=nothing, O, or NH;

R, R′ independently=nothing or (CH 2 ) p ;

p=1-3;

Q, Q′ independently=nothing or C(═O)NHCH 2 CH 2 O;

A′=H or CH 3 ;

G=H, C 1 -C 4 alkyl, (CH 2 ) m NH 2 , (CH 2 ) m CO 2 H, or R′—X′-Q′—C(═O)C(═CH 2 )A′; and

n=45-225 when G=H, C 1 -C 4 alkyl, (CH 2 ) m NH 2 , or (CH 2 ) m CO 2 H; otherwise, n=51-225; and

c) a polymerizable cross-linking agent.

2. The polymeric device material of claim 1 wherein the monomer of structure (I) is selected from the group consisting of: 2-ethylphenoxy acrylate; phenyl acrylate; benzyl acrylate; 2-phenylethyl acrylate; 3-phenylpropyl acrylate; 4-phenylbutyl acrylate; 4-methylphenyl acrylate; 4-methylbenzyl acrylate; 2-2-methylphenylethyl acrylate; 2-3-methylphenylethyl acrylate; 2-4-methylphenylethyl acrylate; 2-(4-propylphenyl)ethyl acrylate; 2-(4-(1-methylethyl)phenyl)ethyl acrylate; 2-(4-methoxyphenyl)ethyl acrylate; 2-(4-cyclohexylphenyl)ethyl acrylate; 2-(2-chlorophenyl)ethyl acrylate; 2-(3-chlorophenyl)ethyl acrylate; 2-(4-chlorophenyl)ethyl acrylate; 2-(4-bromophenyl)ethyl acrylate; 2-(3-phenylphenyl)ethyl acrylate; 2-(4-phenylphenyl)ethyl acrylate; 2-(4-benzylphenyl)ethyl acrylate; 2-ethylphenoxy methacrylate; phenyl methacrylate; benzyl methacrylate; 2-phenylethyl methacrylate; 3-phenylpropyl methacrylate; 4-phenylbutyl methacrylate; 4-methylphenyl methacrylate; 4-methylbenzyl methacrylate; 2-2-methylphenylethyl methacrylate; 2-3-methylphenylethyl methacrylate; 2-4-methylphenylethyl methacrylate; 2-(4-propylphenyl)ethyl methacrylate; 2-(4-(1-methylethyl)phenyl)ethyl methacrylate; 2-(4-methoxyphenyl)ethyl methacrylate; 2-(4-cyclohexylphenyl)ethyl methacrylate; 2-(2-chlorophenyl)ethyl methacrylate; 2-(3-chlorophenyl)ethyl methacrylate; 2-(4-chlorophenyl)ethyl methacrylate; 2-(4-bromophenyl)ethyl methacrylate; 2-(3-phenylphenyl)ethyl methacrylate; 2-(4-phenylphenyl)ethyl methacrylate; and 2-(4-benzylphenyl)ethyl methacrylate.

3. The polymeric device material of claim 1 wherein for the monomer of structure (I): B is (CH 2 ) m , m is 2-5, Y is nothing or O, w is 0-1, and D is H.

4. The polymeric device material of claim 3 wherein the monomer of structure (I) is selected from the group consisting of: 2-phenylethyl acrylate; 4-phenylbutyl acrylate; 5-phenylpentyl acrylate; 2-benzyloxyethyl acrylate; 3-benzyloxypropyl acrylate; 2-phenylethyl methacrylate; 4-phenylbutyl methacrylate; 5-phenylperityl methacrylate; 2-benzyloxyethyl methacrylate; and 3-benzyloxypropyl methacrylate.

5. The polymeric device material of claim 1 wherein the amount of monomer of structure (I) is 75-90% (w/w).

6. The polymeric device material of claim 1 wherein for the monomer of structure (II):

X, X′ independently=nothing or O;

R, R′=nothing;

Q, Q′ independently=nothing or C(═O)NHCH 2 CH 2 O;

A′=H or CH 3 ;

G=C 1 -C 4 alkyl or R′—X′-Q′—C(═O)C(═CH 2 )A′; and

n=45-180 when G=C 1 -C 4 alkyl; otherwise, n=51-225.

7. The polymeric device material of claim 1 wherein for the monomer of structure (II) has a polyethylene glycol component having a number average molecular weight of 2,000-8,000 Daltons.

8. The polymeric device material of claim 7 wherein the monomer of structure (II) has a polyethylene glycol component having a number average molecular weight of 2,000-6,000 Daltons.

9. The polymeric device material of claim 8 wherein the monomer of structure (II) has a polyethylene glycol component having a number average molecular weight of 2,500-6,000 Daltons.

10. The polymer device material of claim 1 wherein the amount of monomer of structure (II) is 2-5% (w/w).

11. The polymeric device material of claim 10 wherein the amount of monomer of structure (II) is 2-4% (w/w).

12. The polymeric device material of claim 1 wherein the cross-linking monomer is selected from the group consisting of: ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, allyl methacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,4-butanediol dimethacrylate; CH 2 ═C(CH 3 )C(═O)O—(CH 2 CH 2 O) p —C(═O)C(CH 3 )═CH 2 where p=1-50; and CH 2 ═C(CH 3 )C(═O)O(CH 2 ) t O—C(═O)C(CH 3 )═CH 2 where t=3-20; and their corresponding acrylates.

13. The polymeric device material of claim 12 wherein the cross-linking monomer is selected from the group consisting of ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; triethylene glycol dimethacrylate; triethylene glycol diacrylate; 1,4-butanediol diacrylate; and CH 2 ═C(CH 3 )C(═O)O—(CH 2 CH 2 O) p —C(═O)C(CH 3 )═CH 2 where p is such that the number-average molecular weight is about 400, about 600, or about 1000.

14. The polymeric device material of claim 1 further comprising an ingredient selected from the group consisting of polymerizable UV absorbers and polymerizable colorants.

15. The polymeric device material of claim 14 comprising 0.1-5% (w/w) of a polymerizable UV absorber and 0.01-0.5% (w/w) of a polymerizable colorant.

16. The polymeric device material of claim 1 wherein the polymeric device material has an equilibrium water content of less than 2.0 weight % across the temperature range of 16-45° C.

17. The polymeric device material of claim 1 wherein the polymeric device material further comprises a siloxane monomer of the structure:

wherein

R 2 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 ) 3 .

18. The polymeric device material of claim 1 wherein the polymeric device material further comprises 2-hydroxyethyl methacrylate.

19. An ophthalmic or otorhinolaryngological device comprising the polymeric device material of claim 1 wherein the ophthalmic or otorhinolaryngological device is selected from the group consisting of intraocular lenses; contact lenses; keratoprostheses; corneal inlays or rings; otological ventilation tubes; and nasal implants.

20. The ophthalmic or otorhinolaryngological device of claim 17 wherein the ophthalmic or otorhinolaryngological device is an intraocular lens.