Wet-pack intraocular lens materials with high refractive index

Patent metadata

Field	Value
Publication number	US-10064977-B2
Application number	US-201615006287-A
Country	US
Kind code	B2
Filing date	Jan 26, 2016
Priority date	Feb 16, 2015
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

Intraocular lens materials are disclosed. They are soft and very deformable and have a high refractive index, and a high glistening resistance in fully hydrated state. They are particularly suitable for making wet-packed intraocular lenses (IOLs) which can be delivered through sub 2.0 mm incisions.

First claim

We claim:

1. A polymeric intraocular lens material, which is polymerization product of a polymerizable composition comprising
(a) from about 10% to about 30% by weight of a hydrophilic monomer relative to the total amount of all polymerizable components, wherein the hydrophilic monomer is hydroxyethylmethacrylate, hydroxyethylacrylate, N-hydroxyethylmethacrylamide, N-hydroxyethylacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, or a combination thereof,
(b) from about 20% to about 85% by weight of one or more poly(phenyl ether)-containing monomers of formula (I) relative to the total amount of all polymerizable components

wherein:
R 1 is H or CH 3 ;
R a , R b , R c , R d , R e , R f , R g , R h , and R i independent of one another are H, C 1 -C 12 alkyl, or C 1 -C 12 alkoxy;
B p is a direct bond, (CH 2 ) m1 , or (OCH 2 CH 2 ) m2 , in which m1 is 2-6 and m2 is 1-10;
n1 is an integer from 1 to 9;
n2 is an integer from 0 to 6;
Y p is 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 ,

(c) from 0 to about 50% by weight of one or more aryl acrylic monomers of formula (II) relative to the total amount of all polymerizable components

wherein A 1 is H or CH 3 ; B 1 is (CH 2 ) m1 or [O(CH 2 ) 2 ] Z1 in which m1 is 2-6 and z1 is 1-10; Y 1 is a direct bond, O, S, or NR″ in which R″ is H, CH 3 , C n′ H 2n′+1 in which n′=1-10, iso-OC 3 H 7 , C 6 H 5 , or CH 2 C 6 H 5 ; W1 is 0-6, provided that m1+w1≤8;
and D 1 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 , and

(d) one or more polymerizable crosslinking agents,
wherein the listed components and any additional polymerizable components add up to 100% by weight,
wherein the intraocular lens material in a fully-hydrated state has: a glass transition temperature of less than 22° C., a refractive index of 1.55 or greater measured at 589 nm and at room temperature (23±2° C.), an equilibrium water content of less than 5.0% by weight at a temperature of from 16° C. to 45° C., a Young's modulus of less than 80 MPa, an elongation of at least 100%, a 100% secant modulus of less than 6.0 MPa, and a glistening resistance characterized by having no bright field microvacuoles and about 10 or less microvacuoles per viewing screen.

2. The intraocular lens material of claim 1 , wherein the intraocular lens material in the fully hydrated state has a surface light scattering of less than 30 CCT units (computer-compatible-tape units) after 10-years accelerated aging (90° C., 81 days in a Balanced Salt Solution, BSS).

3. The intraocular lens material according to claim 2 , wherein the polymerizable composition comprises from about 15% to about 25% by weight of the hydrophilic monomer.

4. The intraocular lens material according to claim 2 , wherein the polymerizable composition comprises from about 25% to about 75% by weight of said one or more poly(phenyl ether)-containing monomers of formula (I).

5. The intraocular lens material according to claim 2 , wherein the polymerizable composition comprises from about 10% to about 45% by weight of said one or more aryl acrylic monomers of formula (II).

6. The intraocular lens material of according to claim 2 , wherein the polymerizable composition comprises from about 1.0% to about 4.0% by weight of the polymerizable crosslinking agent.

7. The intraocular lens material according to claim 2 , wherein in formula (I), R a , R b , R c , R d , R e , R f , R g , R h , and R i independent of one another are H, n1 is an integer from 2 to 6, n2 is an integer from 0 to 4.

8. The intraocular lens material of claim 2 , wherein said one or more poly(phenyl ether)-containing monomers of formula (I) are selected from the group consisting of:

9. The intraocular lens material of claim 2 , wherein said one or more aryl acrylic monomers are: 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; or combinations thereof.

10. The intraocular lens material of claim 2 , wherein said one or more aryl acrylic monomers are: 2-phenylethyl acrylate; 3-phenylpropyl acrylate; 4-phenylbutyl acrylate; 5-phenylpentyl acrylate; 2-benzyloxyethyl acrylate; 3-benzyloxypropyl acrylate; 2-[2-(benzyloxy)ethoxy]ethyl acrylate; their corresponding methacrylates, or combinations thereof.

11. The intraocular lens material of claim 2 , wherein the polymerizable crosslinking agents are 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; ethylene glycol diacrylate; diethylene glycol diacrylate; triethylene glycol diacrylate, tetraethylene glycol diacrylate, allyl acrylate; 1,3-propanediol diacrylate; 2,3-propanediol diacrylate; 1,6-hexanediol diacrylate; 1,4-butanediol diacrylate; N,N′-hexamethylene bisacrylamide; N,N′-hexamethylene bismethacrylamide; N,N′-dihydroxyethylene bisacrylamide; N,N′-dihydroxyethylene bismethacrylamide; N,N′-methylene bisacrylamide; N,N′-methylene bismethacrylamide; 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; CH 2 ═CHC(═O)O—(CH 2 CH 2 O) p —C(═O)CH═CH 2 where p=1-50; CH 2 ═C(CH 3 )C(═O)O(CH 2 ) t O—)C(CH 3 )═CH 2 where t=3-20; CH 2 ═CHC(═O)O(CH 2 ) t O—C(═O)CH═CH 2 where t=3-20, and combinations thereof.

12. The intraocular lens material of claim 11 , wherein the polymerizable crosslinking agents are selected from the group consisting of 1,6-hexanediol diacrylate, 1,4-butanediol diacrylate, N,N′-hexamethylene bisacrylamide, and

Assignees

• Novartis Ag

Inventors

• Jiang Xuwei
• Schlueter Douglas
• Laredo Walter

Classifications

• C08F220/305

  and containing a polyether chain in the alcohol moiety · CPC title

• A61L27/18 Primary

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61L27/50

  Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title

• A61F2/16

  Intraocular lenses · CPC title