Methacrylic materials suitable for ophthalmic and otorhinolaryngological devices

1. A methacrylic polymeric ophthalmic or otorhinolaryngological device material made by polymerizing a mixture of monomers wherein the mixture comprises

a) 65 to 90% (w/w) of a monofunctional methacrylate monomer of formula [1]:

wherein

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

R 1 =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 methacrylate cross-linking monomer of formula [2]:

wherein

R 2 , R 3 independently=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;

c) 1 to 15% (w/w) of an ethoxylate selected from the group consisting of alkyl ethoxylate monomers of formula [3a] and alkylphenol ethoxylate monomers of formula [3b]:

wherein:

n=12, 13, or 14;

e=1-100;

R 4 =CH 3 , CH 2 CH 3 , CH 2 OH; and

R 5 =CH 2 CH 2 OC(═O)C(CH 3 )═CH 2 or

wherein:

T=C 8 H 17 or C 9 H 19 ;

f=1-100;

R 6 =CH 3 , CH 2 CH 3 , CH 2 OH; and

R 7 =CH 2 CH 2 OC(═O)C(CH 3 )═CH 2 or

and

d) 5 to 20% (w/w) of a methacrylate monomer of formula [4]

wherein:

G=C p H 2p+1 ;

R 8 =CH 3 , CH 2 CH 3 , or CH 2 OH; and

p=5-22.

2. The polymeric device material of claim 1 wherein for the monomer of formula [1]:

B=O(CH 2 ) n ;

R 1 =CH 3 ;

n=1-4; and

A=C 6 H 5 .

3. The polymeric device material of claim 1 wherein for the monomer of formula [2]:

R 2 , R 3 independently=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 for the monomer of formula [3a]:

n=12, 13, or 14;

e=8-50;

R 4 =CH 3 ; and

R 5 =CH 2 CH 2 OC(═O)C(CH 3 )═CH 2 or

5. The polymeric device material of claim 4 wherein for the monomer of formula [3a]:

n=13;

e=15-40;

R 4 =CH 3 .

6. The polymeric device material of claim 1 wherein for the monomer of formula [3b]:

T=C 8 H 17 or C 9 H 19 ;

f=8-50;

R 6 =CH 3 .

7. The polymeric device material of claim 6 wherein for the monomer of formula [3b]:

T=2,4,4-trimethylpentan-2-yl or 3-ethyl-4-methylhexan-2-yl;

f=15-40;

R 6 =CH 3 .

8. The polymeric device material of claim 1 wherein for the monomer of formula [4]:

G=(CH 2 ) p CH 3 ;

R 8 =CH 3 ; and

p=5-21.

9. 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; and 3-benzyloxypropyl methacrylate.

10. 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; and 1,4-benzenedimethanol dimethacrylate.

11. The polymeric device material of claim 1 wherein the amount of monomer [1] is 70 to 85% (w/w).

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

13. The polymeric device material of claim 1 wherein the polymeric device material comprises both a monomer of formula [3a] and a monomer of formula [3b] and wherein the total amount of monomer [3a] and [3b] is 1 to 10% (w/w).

14. The polymeric device material of claim 13 wherein the total amount of monomer [4] is 10 to 20% (w/w).

15. 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.

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

17. 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.

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