Hydroxyphenyl naphthotriazoles as polymerizable blockers of high energy light

Patent metadata

Field	Value
Publication number	US-10975040-B2
Application number	US-201916685001-A
Country	US
Kind code	B2
Filing date	Nov 15, 2019
Priority date	Jun 30, 2017
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

Described are high energy light blocking compounds and ophthalmic devices containing the compounds. In particular, described are hydroxyphenyl naphthotriazole structures with polymerizable functionality that block high energy light and are visibly transparent. The hydroxyphenyl naphthotriazole structures can be incorporated into ophthalmic devices, such as hydrogel contact lenses, to protect eyes from high energy light radiation.

First claim

We claim:

1. An ophthalmic device comprising a free radical reaction product of (a) at least one compound of formula I:

wherein:
R 1 at each occurrence is independently H, halo, C 1 -C 6 alkyl, C 3 -C 12 cycloalkyl, aryl, or aryl-C 1 -C 6 -alkyl;
at least one R 2 is a group of formula R g -L, wherein R g is a polymerizable group and L is a linking group, and the remaining R 2 are independently at each occurrence H, C 1 -C 6 alkyl, C 3 -C 12 cycloalkyl, aryl, or aryl-C 1 -C 6 -alkyl, wherein L at each occurrence is independently [CH 2 ] m Y—[CH 2 ] n —, wherein m is a number from 1 to 6, n is a number from 1 to 6, Y is O, S, C(═O)O, NR 3 , or C(═O)NR 3 , and R 3 is H or C 1 -C 4 alkyl; and

wherein each alkyl, cycloalkyl, and aryl group is unsubstituted or substituted; and
(b) at least one silicone-containing component and at least one hydrophilic monomer.

2. The ophthalmic device of claim 1 wherein R 1 is at each occurrence is independently H, chloro, C 1 -C 4 alkyl, phenyl, or benzyl.

3. The ophthalmic device of any one of claims 1 to 2 wherein R 2 at each occurrence is independently H, C 1 -C 4 alkyl, phenyl, benzyl, or Rg-L.

4. The ophthalmic device of claim 3 wherein Rg comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.

5. The ophthalmic device of claim 4 wherein the linking group comprises C 1 -C 6 oxaalkylene, C 1 -C 6 thiaalkylene, C 1 -C 4 alkylene-carboxylate-C 1 -C 4 alkylene, C 1 -C 4 alkylene-amide-C 1 -C 4 alkylene, or C 1 -C 4 alkylene-amine-C 1 -C 4 alkylene.

6. The ophthalmic device of claim 4 further comprising at least one additional component selected from the group consisting of diluents, initiators, UV absorbers, visible light absorbers, photochromic compounds, pharmaceuticals, nutraceuticals, antimicrobial substances, tints, pigments, copolymerizable dyes, nonpolymerizable dyes, release agents, and combinations thereof.

7. The ophthalmic device of claim 6 wherein the at least one hydrophilic monomer is selected from the group consisting of hydrophilic (meth)acrylate, hydrophilic (meth)acrylamide monomers, ionic monomers, hydrophilic N-vinyl lactam and N-vinyl amide monomers, hydrophilic O-vinyl carbamates and O-vinyl carbonates monomers, hydrophilic vinyl compounds and mixtures thereof.

8. The ophthalmic device of claim 7 wherein the hydrophilic monomer is selected from the group consisting of acrylamide, N-isopropyl acrylamide, N,N-dimethylaminopropyl (meth)acrylamide, N,N-dimethyl acrylamide (DMA), 2-hydroxyethyl methacrylate (HEMA), 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, N-(2-hydroxyethyl) (meth)acrylamide, N,N-bis(2-hydroxyethyl) (meth)acrylamide, N-(2-hydroxypropyl) (meth)acrylamide, N,N-bis(2-hydroxypropyl) (meth)acrylamide, N-(3-hydroxypropyl) (meth)acrylamide, N-(2-hydroxybutyl) (meth)acrylamide, N-(3-hydroxybutyl) (meth)acrylamide, N-(4-hydroxybutyl) (meth)acrylamide, 2-aminoethyl (meth)acrylate, 3-aminopropyl (meth)acrylate, 2-aminopropyl (meth)acrylate, N-2-aminoethyl (meth)acrylamides), N-3-aminopropyl (meth)acrylamide, N-2-aminopropyl (meth)acrylamide, N,N-bis-2-aminoethyl (meth)acrylamides, N,N-bis-3-aminopropyl (meth)acrylamide), N,N-bis-2-aminopropyl (meth)acrylamide, glycerol methacrylate, polyethyleneglycol monomethacrylate, (meth)acrylic acid, vinyl acetate, acrylonitrile and mixtures thereof.

9. The ophthalmic device of claim 4 that is a contact lens, a corneal onlay, a corneal inlay, an intraocular lens, or an overlay lens.

10. The ophthalmic device of claim 6 wherein the at least one hydrophilic monomer is selected from the group consisting of N,N-dimethyl acrylamide, 2-hydroxyethyl methacrylate, N-vinyl pyrrolidone, N-vinyl-N-methylacetamide, N-vinyl acetamide, and mixtures thereof.

11. The ophthalmic device of claim 6 wherein the at least one silicone-containing component comprises (a) one or more polymerizable groups selected from the group consisting of (meth)acrylate,(meth)acrylamide, or mixtures thereof; (b) one or more optionally repeating siloxane units; and (c) one or more linking groups connecting the polymerizable groups to the siloxane units.

12. The ophthalmic device of claim 6 wherein the at least one silicone-containing component is at least one mono-functional polymerizable compound of formula B:

wherein: j1 is zero and j2 is from 1 to 20, and Rg is a polymerizable group;
L is a linking group;
R A1 , R A2 , R A3 , R A4 , R A5 , and R A7 are independently at each occurrence C 1 -C 6 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 6 alkoxy, C 4 -C 12 cyclic alkoxy, alkoxy-alkyleneoxy-alkyl, aryl, aryl-alkyl, haloalkyl, siloxy, fluoro, or combinations thereof, wherein each alkyl in the foregoing groups is optionally substituted with one or more hydroxy, amino, amido, oxa, carboxy, alkyl carboxy, carbonyl, alkoxy, carbamate, carbonate, halo, phenyl, or benzyl, each cycloalkyl is optionally substituted with one or more alkyl, hydroxy, amino, amido, oxa, carbonyl, alkoxy, carbamate, carbonate, halo, phenyl, or benzyl and each aryl is optionally substituted with one or more alkyl, hydroxy, amino, amido, oxa, carboxy, alkyl carboxy, carbonyl, alkoxy, carbamate, carbonate, halo, phenyl, or benzyl; and
R A6 is siloxy, C 1 -C 8 alkyl, or aryl, wherein alkyl and aryl may optionally be substituted with one or more fluorine atoms.

13. The ophthalmic device of claim 8 wherein the at least one silicone-containing component is selected from the group consisting of mono-methacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxanes (mPDMS) containing from 3 to 15 SiO repeating units; mono-acryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane containing from 3 to 20 SiO repeating units; mono-acryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane containing from 3 to 20 SiO repeating units; mono(meth)acryloxypropyl terminated mono-n-methyl terminated polydimethylsiloxane containing from 3 to 20 SiO repeating units; mono(meth)acryloxypropyl terminated mono-n-methyl terminated polydimethylsiloxane containing from 3 to 20 SiO repeating units; mono(meth)acryloxypropyl terminated mono-n-butyl terminated polydiethylsiloxane containing from 3 to 20 SiO repeating units; mono(meth)acryloxypropyl terminated mono-n-methyl terminated polydiethylsiloxane containing from 3 to 20 SiO repeating units; mono(meth)acryloxypropyl terminated mono-n-methyl terminated polydiethylsiloxane containing from 3 to 20 SiO repeating units; mono(meth)acrylamidoalkylpolydialkylsiloxanes containing from 3 to 20 SiO repeating units; mono(meth)acryloxyalkyl terminated mono-alkyl polydiarylsiloxanes containing from 3 to 20 SiO repeating units; 3-methacryloxypropyltris(trimethylsiloxy)silane (TRIS); 3-methacryloxypropylbis(trimethylsiloxy)methylsilane; 3-methacryloxypropylpentamethyl disiloxane mono(meth)acrylamidoalkylpolydialkylsiloxanes containing from 3 to 20 SiO repeating units; mono(meth)acrylamidoalkyl polydimethylsiloxanes containing from 3 to 20 SiO repeating units; N-(2,3-dihydroxypropane)-N′-(propyl tetra(dimethylsiloxy) dimethylbutylsilane)acrylamide; N-[3-tris(trimethylsiloxy)silyl]-propyl acrylamide; 2-hydroxy-3-[3-methyl-3,3-di(trimethylsiloxy)silylpropoxy]-propyl methacrylate (SiMAA); 2-hydroxy-3-m

Assignees

• Johnson & Johnson Vision Care

Inventors

• Mahadevan Shivkumar
• Sonoda Leilani K
• Sinha Dola
• Martin Patricia

Classifications

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C07D249/22 Primary

  Naphthotriazoles · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08J2383/04

  Polysiloxanes · CPC title

• C08J3/075

  Macromolecular gels · CPC title