Ophthalmic and otorhinolaryngological device materials containing a reactive NVP macromer

1. An intraocular lens comprising a polymeric device material, wherein the polymeric device material has an equilibrium water content of: 0.5 to 3 weight percent and is formed by polymerizing a composition comprising

a) 75 to 97% (w/w) of a monofunctional monomer of formula [1]:

wherein

B═O(CH 2 ) n , NH(CH 2 ) n , or NCH 3 (CH 2 ) n ;

R 1 ═H, CH 3 , CH 2 CH 3 , or CH 2 OH;

n=0-12;

A=C 6 H 5 or O(CH 2 ) m C 6 H 5 , where the C 6 H 5 group is optionally substituted with —(CH 2 ) n H, —O(CH 2 ) n H, —CH(CH 3 ) 2 , —C 6 H 5 , —OC 6 H 5 , —CH 2 C 6 H 5 , F, Cl, Br, or I;

and

m=0-22;

b) a difunctional cross-linking monomer of formula [2]:

wherein

R 2 , R 3 independently═H, CH 3 , CH 2 CH 3 , or CH 2 OH;

W, W′ independently═O(CH 2 ) d , NH(CH 2 ) d , NCH 3 (CH 2 ) d , O(CH 2 ) d C 6 H 4 , O(CH 2 CH 2 O) d CH 2 , O(CH 2 CH 2 CH 2 O) d CH 2 , O(CH 2 CH 2 CH 2 CH 2 O) d CH 2 , or nothing;

J=(CH 2 ) a , O(CH 2 CH 2 O) b , O, or nothing, provided that if W and W′=nothing, then J≠nothing;

d=0-12;

a=1-12; and

b=1-24;

and

c) 1 to 8% (w/w) of a macromer of formula [3]:

wherein:

D=OCH 2 CH 2 S, SCH 2 C═O, CH 3 CH(O)CH 2 S, SCH 2 CH(OH)CH 2 O, S(CH 2 ) 11 O, S(CH 2 ) 10 C═O, S(CH 2 ) 14 C═O, S(CH 2 ) 15 C═O, SC 6 H 4 CH 2 O, CH 3 CH(S)C═O, S(CH 2 CH 2 CH 2 )O, CH 3 CH(S)CH(O)CH 3 , OCH 2 CH 2 C(CH 3 ) 2 S, SCH 2 CH 2 C═O, S(CH 2 ) 4 O, SC 6 H 4 CH 2 C═O, SC 6 H 4 C═O, S(CH 2 ) 11 C═O, CH 3 CH(O)CH(S)CH 3 , SC 6 H 4 C═O, S(CH 2 ) 6 OC 6 H 4 CH 2 O, S(CH 2 ) 6 O, S(CH 2 ) 5 C═O, S(CH 2 ) 7 C═O, or S(CH 2 ) 9 O;

E=nothing, O(CH 2 ) n NH, O(CH 2 ) n NHC═O, or HN(CH 2 ) n NH;

n=2-12;

R 1 ═H, CH 3 , CH 2 CH 3 , or CH 2 OH; and

p=10-100.

2. The intraocular lens of claim 1 wherein

B═O(CH 2 ) n ;

R 1 ═H or CH 3 ;

n=1-4; and

A=C 6 H 5 .

3. The intraocular lens of claim 1 wherein

R 2 , R 3 independently═H or CH 3 ;

W, W′ independently═O(CH 2 ) d , O(CH 2 ) d C 6 H 4 , or nothing;

J=O(CH 2 CH 2 O) b or nothing, provided that if W and W′=nothing, then J≠nothing;

d=0-6; and

b=1-10.

4. The intraocular lens of claim 1 wherein

D=OCH 2 CH 2 S, CH 3 CH(O)CH 2 S, SCH 2 CH(OH)CH 2 O, S(CH 2 ) 11 O, SC 6 H 4 CH 2 O, S(CH 2 CH 2 CH 2 )O, CH 3 CH(S)CH(O)CH 3 , OCH 2 CH 2 C(CH 3 ) 2 S, S(CH 2 ) 4 O, CH 3 CH(O)CH(S)CH 3 , S(CH 2 ) 6 OC 6 H 4 CH 2 O, S(CH 2 ) 6 O, or S(CH 2 ) 9 O;

E=nothing or O(CH 2 ) 2 NHC═O;

R 1 ═H, CH 3 , CH 2 CH 3 , or CH 2 OH; and

p=10-75.

5. The intraocular lens of claim 4 wherein

D=OCH 2 CH 2 S, S(CH 2 CH 2 CH 2 )O, SCH 2 CH(OH)CH 2 O, SC 6 H 4 CH 2 O,

S(CH 2 ) 4 O, or S(CH 2 ) 6 OC 6 H 4 CH 2 O;

E=nothing;

R 1 ═H or CH 3 ; and

p=10-50.

6. The intraocular lens of claim 1 wherein the monomer of formula [1] is selected from the group consisting of benzyl methacrylate; 2-phenylethyl methacrylate; 3-phenylpropyl methacrylate; 4-phenylbutyl methacrylate; 5-phenylpentyl methacrylate; 2-phenoxyethyl methacrylate; 2-(2-phenoxyethoxy)ethyl methacrylate; 2-benzyloxyethyl methacrylate; 2-(2-(benzyloxy)ethoxy)ethyl methacrylate; 3-benzyloxypropyl methacrylate; benzyl acrylate; 2-phenylethyl acrylate; 3-phenylpropyl acrylate; 4-phenylbutyl acrylate; 5-phenylpentyl acrylate; 2-phenoxyethyl acrylate; 2-(2-phenoxyethoxy)ethyl acrylate; 2-benzyloxyethyl acrylate; 2-(2-(benzyloxy)ethoxy)ethyl acrylate; and 3-benzyloxypropyl acrylate.

7. The intraocular lens of claim 1 wherein the monomer of formula [2] is selected from the group consisting of ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; triethylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,4-butanediol dimethacrylate; 1,4-benzenedimethanol dimethacrylate; ethylene glycol diacrylate; diethylene glycol diacrylate; triethylene glycol diacrylate; 1,6-hexanediol diacrylate; 1,4-butanediol diacrylate; and 1,4-benzenedimethanol diacrylate.

8. The intraocular lens of claim 1 wherein the amount of monomer [1] is 80 to 95% (w/w).

9. The intraocular lens of claim 1 wherein the amount of monomer [2] is 0.5 to 3% (w/w).

10. The intraocular lens of claim 1 wherein the amount of monomer [3] is 2 to 7% (w/w).

11. The intraocular lens of claim 10 wherein the amount of monomer [3] is 2 to 6% (w/w).

12. The intraocular lens of claim 1 wherein the composition further comprises an ingredient selected from the group consisting of a polymerizable UV absorbers and a polymerizable colorants.

13. The intraocular lens of claim 12 wherein the composition comprises 0.1-5% (w/w) of a polymerizable UV absorber and 0.01-0.5% (w/w) of a polymerizable colorant.