Ophthalmic and otorhinolaryngological device materials

1. A polymeric ophthalmic or otorhinolaryngological device material formed by polymerizing a composition compromising

a) 70 to 98% (w/w) of a monofunctional acrylate or methacrylate monomer of formula [1]:

wherein

B=—O(CH 2 ) n —, —(OCH 2 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=0-18;

b) 0.5-3% (w/w) of 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) 1.5 to 4% (w/w) of a hydrophilic side-chain macromer of formula [3c]:

wherein for formula [3c]:

e=1-50;

X=—O—, NH—, —N(CH 3 )—, —N(CH 2 CH 3 )—, or —N(C 6 H 5 )—;

Y=—H, —(CH 2 ) p OH, —CH 2 CH 2 N(CH 3 ) 2 , —CH 2 CH 2 N(CH 2 CH 3 ) 2 , —CH 2 CH(OH)CH 2 OH, —(CH 2 CH 2 O) q CH 3 , —(CH 2 CH 2 O) q H, —(CH 2 CH 2 O) q C 6 H 5 , or

p=1-12;

q=1-230;

T, T′ 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;

K=NHC(O)O;

d′=0-12;

L=H, Cl, Br, —CH 2 C(O)CH 3 , CH 2 C(O)C(CH 3 ) 3 , —CH 2 C(O)C 6 H 5 , —CH 2 C(O)C 6 H 4 OH, —CH 2 C(O)C 6 H 4 OCH 3 ,

 or —CH 2 CH═CH 2 ;

R 4 , R 5 independently=H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , or CH 2 CH(CH 3 ) 2 ; and

R 7 , R 8 independently=H, CH 3 , CH 2 CH 3 , or CH 2 OH;

wherein % (w/w) is relative to the composition to be polymerized excluding any polymerization initator.

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

B=—O(CH 2 ) n — or —(OCH 2 CH 2 ) n —;

R 1 =—H or —CH 3 ;

n=1-5;

A=—C 6 H 5 , O(CH 2 ) m C 6 H 5 ; and

m=0-4.

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

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 for the macromer of formula [3c]:

e=2-40;

X=—O— or —N(CH 3 )—;

Y=(CH 2 CH 2 O) q CH 3 , —(CH 2 CH 2 O) q H, or —(CH 2 CH 2 O) q C 6 H 5 ;

q=2-23;

T, T′ independently=O(CH 2 ) d′ or nothing;

d′=0-6;

L=H, Cl, Br, —CH 2 C(O)C 6 H 5 , —CH 2 C(O)C 6 H 4 OH, —CH 2 C(O)C 6 H 4 OCH 3 , or —CH 2 CH═CH 2 ;

R 4 , R 5 independently=H, CH 3 , or CH 2 CH 3 ; and

R 7 , R 8 independently=H or CH 3 .

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

e=5-30;

X=—O—;

Y=(CH 2 CH 2 O) q CH 3 ;

q=4-15;

T, T′ independently=O(CH 2 ) d′ , O(CH 2 ) d′ C 6 H 4 , or nothing; and

L=H, —CH 2 C(O)C 6 H 5 , —CH 2 C(O)C 6 H 4 OCH 3 , or —CH 2 CH═CH 2 .

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 hydrophilic side-chain macroner in the composition is 2 to 4% (w/w).

10. 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.

11. The polymeric device material of claim 10 comprising 0.1-5% (w/w) of a polymerizable UV absorber and 0.01-0.5% (w/w) of a polymerizable colorant.

12. 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.

13. The ophthalmic or otorhinolaryngological device of claim 12 wherein the ophthalmic or otorhinolaryngological device is an intraocular lens.