Ophthalmic and otorhinolaryngological device materials containing a multi-arm PEG macromer

1. A polymeric ophthalmic or otorhinolaryngological device material comprising

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

wherein

B═O(CH 2 ) n , NH(CH 2 ), 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 acrylate or methacrylate 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

k=2-75;

s=0 or 1;

t=0-4;

Y independently=H, C(O)CCH 2 R 4 , CH 2 CH 2 NH 2 , CH 2 CH 2 NHC(O)CCH 2 R 4 , CH 2 CH 2 CH(OH)CH 2 OC(O)CCH 2 R 4 , CH 2 CH 2 NHC(O)NHCH 2 CH 2 OC(O)CCH 2 R 4 , C(O)NHCH 2 CH 2 OC(O)CCH 2 R 4 , or CH 2 CH 2 SH; and

R 4 =H, CH 3 , CH 2 CH 3 , or CH 2 OH;

and wherein the polymeric device material has an equilibrium water content (EWC) of 0.5 to 3%.

2. The polymeric device material 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 polymeric device material 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 polymeric device material of claim 1 wherein:

k=8-55;

s=0 or 1;

t=0 or 4;

Y independently=H, C(O)CCH 2 R 4 , CH 2 CH 2 NH 2 , CH 2 CH 2 NHC(O)CCH 2 R 4 , or C(O)NHCH 2 CH 2 OC(O)CCH 2 R 4 ; and

R 4 ═H, CH 3 , CH 2 CH 3 , or CH 2 OH.

5. The polymeric device material of claim 4 wherein:

k=11-35;

s=1;

t=0;

Y═H, C(O)CCH 2 R 4 , CH 2 CH 2 NH 2 , or CH 2 CH 2 NHC(O)CCH 2 R 4 ; and

R 4 ═H or CH 3 .

6. The polymeric device material 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 polymeric device material 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 polymeric device material of claim 1 wherein the amount of monomer [1] is 80 to 95% (w/w).

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

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

11. The polymeric device material of claim 10 wherein the amount of monomer [3] is 3 to 5% (w/w).

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

13. The polymeric device material of claim 12 comprising 0.1-5% (w/w) of a polymerizable UV absorber and 0.01-0.5% (w/w) of a polymerizable colorant.

14. An ophthalmic or otorhinolaryngological device comprising the 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.

15. The ophthalmic or otorhinolaryngological device of claim 14 wherein the ophthalmic or otorhinolaryngological device is an intraocular lens.