Soft acrylic materials with high refractive index and minimized glistening

1. A polymeric ophthalmic or otorhhinolaryngological device material, having a refractive index of 1.57 or greater measured at 589 nm and at room temperature (23±3° C.) in fully hydrated state, a Young's modulus of about 60 MPa or less, a glass transition temperature of about 35° C. or less, an elongation of at least 100%, wherein the polymeric ophthalmic or otorhhinolaryngological device material is a copolymerization product of a polymerizable composition comprising a poly(phenyl ether)-containing monomer of formula (IA) and/or a poly(phenyl ether)-containing cross-linking agent of formula (IB)

wherein:

R 1 and R 1 ′ independently of each other are H or CH 3 ;

R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k , R l , R m , R n , R o , R p , and R q independent of one another are H, C 1 -C 12 alkyl, or C 1 -C 12 alkoxy;

B 1 and B 1 ′ independently of each other are a direct bond, (CH 2 ) m1 , or (OCH 2 CH 2 ) m2 , in which m1 is 2-6 and m2 is 1-10;

Q 1 and Q 1 ′ independently of each other are a direct bond, O, NH, or C(═O)NH(CH 2 ) m3 O in which m3 is an integer of 2-6;

n1 is an integer from 1 to 9;

n2 and n2′ independently of each other are an integer from 0 to 6;

n3 is an integer from 1 to 100; and

Y 1 and Y 1 ′ independently of each other are a direct bond, O, S, OC(═O)NH, NHC(═O)NH, or NR′ in which R′ is H, C 1 -C 10 alkyl, C 6 H 5 , or CH 2 C 6 H 5 .

2. The device material of claim 1 , wherein the device material is characterized by having a refractive index of 1.58 or greater measured at 589 nm and at room temperature in fully hydrated state, a Young's modulus of from about 1 MPa to about 45 MPa, a glass transition temperature of about 30° C. or less, an elongation of at least 110%.

3. The device material of claim 2 , wherein the polymerizable composition comprises:

a) from about 40% to about 95% by weight of at least one poly(phenyl ether)-containing monomer of formula (IA) as defined above; and

b) from about 1% to about 6% by weight of a poly(ethylene glycol)-containing polymerizable component comprising at least one polymerizable group which is acryloyl (OC(═O)CH═CH 2 ), methacryloyl (OC(═O)CCH 3 =CH 2 ), acrylamido (NHC(═O)CH═CH 2 ), methacrylamido (NHC(═O)CCH 3 ═CH 2 ), or thiol group.

4. The device material of claim 3 , wherein said at least one poly(phenyl ether)-containing monomer is selected from the group consisting of:

5. The device material of claim 4 , wherein the poly(ethylene glycol)-containing polymerizable component is represented by formula (II)

wherein: A′ is H or CH 3 ; Q and Q′ independently of each other are a direct bond, O, NH, or C(═O)NHCH 2 CH 2 O; X and X′ independently are a direct bond, O, NH, OC(═O)NH, or NHC(═O)NH; R and R′ independently of each other are a direct bond, or (CH 2 ) p ; p=1-3; m=2-6; G is H, C 1 -C 4 alkyl, (CH 2 ) m NH 2 , (CH 2 ) m CO 2 H, or R′-X′-Q′-C(═O)CA′=CH 2 ; 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.

6. The device material of claim 5 , wherein in formula (II), X and X′ independently of each other are a direct bond or O; R and R′ are a direct bond; Q and Q′ independently of each other are a direct bond or C(═O)NHCH 2 CH 2 O; A′ is H or CH 3 ; G is C 1 -C 4 alkyl or R′-X′-Q′-C(═O)CA′=CH 2 ; and n=45-180 when G=C 1 -C 4 alkyl; otherwise, n=51-225.

7. The device material of claim 5 , wherein the poly(ethylene glycol)-containing polymerizable component of formula (II) has a number average molecular weight of 2,000-10,000 Daltons.

8. The device material of claim 5 , wherein the polymerizable composition for making an ophthalmic device material of the invention further comprises from about 10% to about 45% by weight of one or more aryl acrylic monomers of formula (III)

wherein: A is H or CH 3 ; B 2 is (CH 2 ) m or [O(CH 2 ) 2 ] Z ; m is 2-6; z is 1-10; Y is a direct bond, 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 .

9. The device material of claim 8 , wherein the monomer of formula (III) is selected from the group consisting of: 2-ethylphenoxy acrylate; 2-ethylphenoxy methacrylate; phenyl acrylate; phenyl methacrylate; benzyl acrylate; benzyl methacrylate; 2-phenylethyl acrylate; 2-phenylethyl methacrylate; 3-phenylpropyl acrylate; 3-phenylpropyl methacrylate; 4-phenylbutyl acrylate; 4-phenylbutyl methacrylate; 4-methylphenyl acrylate; 4-methylphenyl methacrylate; 4-methylbenzyl acrylate; 4-methylbenzyl methacrylate; 2-2-methylphenylethyl acrylate; 2,2-methylphenylethyl methacrylate; 2,3-methylphenylethyl acrylate; 2,3-methylphenylethyl methacrylate; 2,4-methylphenylethyl acrylate; 2,4-methylphenylethyl methacrylate; 2-(4-propylphenyl)ethyl acrylate; 2-(4-propylphenyl)ethyl methacrylate; 2-(4-(1-methylethyl)phenyl)ethyl acrylate; 2-(4-(1-methylethyl)phenyl)ethyl methacrylate; 2-(4-methoxyphenyl)ethyl acrylate; 2-(4-methoxyphenyl)ethyl methacrylate; 2-(4-cyclohexylphenyl)ethyl acrylate; 2-(4-cyclohexylphenyl)ethyl methacrylate; 2-(2-chlorophenyl)ethyl acrylate; 2-(2-chlorophenyl)ethyl methacrylate; 2-(3-chlorophenyl)ethyl acrylate; 2-(3-chlorophenyl)ethyl methacrylate; 2-(4-chlorophenyl)ethyl acrylate; 2-(4-chlorophenyl)ethyl methacrylate; 2-(4-bromophenyl)ethyl acrylate; 2-(4-bromophenyl)ethyl methacrylate; 2-(3-phenylphenyl)ethyl acrylate; 2-(3-phenylphenyl)ethyl methacrylate; 2-(4-phenylphenyl)ethyl acrylate; 2-(4-phenylphenyl)ethyl methacrylate; 2-(4-benzylphenyl)ethyl acrylate; 2-(4-benzylphenyl)ethyl methacrylate; 2-(phenylthio)ethyl acrylate; 2-(phenylthio)ethyl methacrylate; 2-benzyloxyethyl acrylate; 3-benzyloxypropyl acrylate; 2-benzyloxyethyl methacrylate; 3-benzyloxypropyl methacrylate; 2-[2-(benzyloxy)ethoxy]ethyl acrylate; 2-[2-(benzyloxy)ethoxy]ethyl methacrylate; and combinations thereof.

10. The device material of claim 5 , wherein the polymerizable composition further comprises a poly(phenyl ether)-containing cross-linking agent of formula (IB) and/or a cross-linking agent 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(CH3)═CH2 where t=3-20; and their corresponding acrylates.

11. The device material of claim 10 , wherein the cross-linking agent is selected from the group consisting of: 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; ethylene glycol dimethacrylate (EGDMA); diethylene glycol dimethacrylate; triethylene glycol dimethacrylate; triethylene glycol diacrylate; and 1,4-butanediol diacrylate (BDDA).

12. The device material of claim 5 , wherein the polymerizable composition further comprises one or more polymerizable components selected from the group consisting of a polymerizable UV-absorber, a polymerizable colored dye, a siloxane monomer, and combinations thereof.

13. The device material of claim 12 , wherein the polymerizable composition further comprises a siloxane monomer of formula (IV)

Wherein: R 2 is H or CH 3 ; T is a direct bond, 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 .

14. An ophthalmic or otorhhinolaryngological device comprising a device material of claim 1 .

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