High refractive index siloxane insert materials for embedded contact lenses

Patent metadata

Field	Value
Publication number	US-11618823-B2
Application number	US-202117205186-A
Country	US
Kind code	B2
Filing date	Mar 18, 2021
Priority date	Mar 19, 2020
Publication date	Apr 4, 2023
Grant date	Apr 4, 2023

Abstract

The invention is generally related to an insert for being embedded in a silicone hydrogel contact lens. The insert is made of a crosslinked materials which are rigid in dry state at room temperature (from about 22° C. to about 26° C.), have a high oxygen permeability and a high refractive index in fully hydrated state. Such materials are useful for making inserts in embedded contact lenses for correcting corneal astigmatism, presbyopia, and color blindness lenses and for imparting photochromic characteristics to the lenses. The invention is also related to a method for making embedded silicone hydrogel contact lenses comprising an insert of the invention therein and to embedded silicone hydrogel contact lenses comprising an insert of the invention therein.

First claim

What is claimed is:

1. An insert for being embedded in a silicone hydrogel contact lens, comprising a crosslinked polymeric material, which comprises:
(1) repeating units at least one vinyl-functional polysiloxane that comprises at least two vinyl groups each directly attached to one silicon atom and at least 15% by mole of siloxane units each having at least one phenyl substituent;
(2) repeating units of at least one aryl acrylic monomer; and
(3) repeating units of at least one vinylic crosslinking agent,
wherein the sum of the amounts of components (1) and (2) of the crosslinked polymeric material is at least about 70% by weight relative to the total weight of the crosslinked polymeric material, wherein the crosslinked polymeric material in dry state has a glass transition temperature of greater than about 28° C., wherein the crosslinked polymeric material in fully hydrated state has a water content of less than about 5% by weight, an oxygen permeability of at least about 40 barrers, and a refractive index of at least about 1.47.

2. The insert of claim 1 , wherein said at least one aryl acrylic monomer is a vinylic monomer of formula (I) or (II)

wherein A 1 is H or CH 3 (preferably H); 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 ; 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 (preferably all are H); w1 is 0-6, provided that m1+w1≤8; w2 is an integer from 1 to 3; 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 .

3. The insert of any one of claim 2 , wherein said at least one aryl acrylic monomer comprises at least one vinylic monomer 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-methylphenyl)ethyl acrylate; 2-(2-methylphenyl)ethyl methacrylate; 2-(3-methylphenyl)ethyl acrylate; 2-(3-methylphenyl)ethyl methacrylate; 2-(4-methylphenyl)ethyl acrylate; 2-(4-methylphenyl)ethyl 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.

4. The insert of claim 2 , wherein said at least one vinylic crosslinking agent comprises ethylene glycol dimethacrylate; ethylene glycol diacrylate; 1,3-propanediol diacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol diacrylate; 2,3-propanediol dimethacrylate; 1,4-butanediol dimethacrylate; 1,4-butanediol diacrylate; 1,5-pentanediol dimethacrylate; 1,5-pentanediol diacrylate; 1,6-hexanediol dimethacrylate; 1,6-hexanediol diacrylate; diethylene glycol dimethacrylate; diethylene glycol diacrylate; triethylene glycol dimethacrylate; triethylene glycol diacrylate; tetraethylene glycol dimethacrylate; tetraethylene glycol diacrylate; allyl methacrylate; allyl acrylate; N,N′-methylene bis(acrylamide); N,N′-methylene bis(methacrylamide); N,N′-ethylene bis(acrylamide); N,N′-ethylene bis(methacrylamide); N,N′-hexamethylene bisacrylamide; N,N′-hexamethylene bismethacrylamide, pentaerythritol triacrylate, pentaerythritol trimethacrylate, trimethyloylpropane triacrylate, trimethyloylpropane trimethacrylate, tris(2-hydroxyethyl)isocyanurate triacrylate, tris(2-hydroxyethyl)isocyanurate trimethacrylate, 1,3,5-triacryloxylhexahydro-1,3,5-triazine, 1,3,5-trimethacryloxylhexahydro-1,3,5-triazine; pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, di(trimethyloylpropane) tetraacrylate, di(trimethyloylpropane) tetramethacrylate, an aryl crosslinking agent (e.g., divinylbenzene, 2-methyl-1,4-divinylbenzene, bis(4-vinylphenyl)methane, 1,2-bs(4-vinylphenyl)ethane, etc.), or combinations thereof.

5. The insert of claim 2 , wherein the amount of said at least one vinylic crosslinking agent is from about 1% to about 30% by weight.

6. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises at least 30% by mole of siloxane units each having at least one phenyl substituent.

7. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises three or more vinylphenylsiloxane units each having at least one phenyl substituent and one vinyl substituent.

8. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises three or more phenylmethylsiloxane units.

9. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises three or more diphenylsiloxane units.

10. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises one or more vinyl terminated polyphenylmethysiloxanes, one or more vinylphenylmethyl terminated phenylmethyl-vinylphenylsiloxane copolymers, one or more vinyl terminated diphenylsiloxane-dimethylsiloxane copolymers, or combinations thereof.

11. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises one or more vinyl terminated polyphenylmethysiloxanes.

12. The insert of claim 5 , wherein said at least one vinyl-functional polysiloxane comprises one or more vinylphenylmethyl terminated phenylmethyl-vinylphenylsiloxane copolymers.

13. An embedded silicone hydrogel contact lenses, comprising: a silicone hydrogel material; and an insert of claim 1 within the silicone hydrogel material, wherein the silicone hydrogel material is a crosslinked material that has a polymer matrix and comprises (a) repeating units of at least one second silicone-containing vinylic monomer and/or at least one second silicone-containing vinylic crosslinker and (b) repeating units of at least one hydrophilic vinylic monomer, wherein the embedded silicone hydrogel contact lens in fully hydrated state has a water content of from about 15% to about 70% by weight of water when being fully hydrated.

14. The embedded silicone hydrogel contact lens of claim 13 , wherein the silicone hydrogel material comprises repeating units of at least one silicone-containing vinylic monomer selected from the group consisting of a vinylic monomer having a bis(trialkylsilyloxy)alkylsilyl group, a vinylic monomer having a tris(trialkylsilyloxy)silyl group, a polysiloxane viny

Assignees

• Alcon Inc

Inventors

• Cheng Jing
• Zhang Steve Yun

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• C08G2210/00

  Compositions for preparing hydrogels · CPC title

• C08L2205/02

  containing two or more polymers of the same C08L -group · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C08F290/068 Primary

  Polysiloxanes · CPC title