Polymerizable absorbers of UV and high energy visible light

Patent metadata

Field	Value
Publication number	US-12196916-B2
Application number	US-202217935677-A
Country	US
Kind code	B2
Filing date	Sep 27, 2022
Priority date	Sep 26, 2018
Publication date	Jan 14, 2025
Grant date	Jan 14, 2025

Abstract

Described are polymerizable high energy light absorbing compounds of formula I:wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and X are as described herein. The compounds absorb various wavelengths of ultraviolet and/or high energy visible light and are suitable for incorporation in various products, such as biomedical devices and ophthalmic devices.

First claim

We claim:

1. An ophthalmic device that is a free radical reaction product of a reactive mixture comprising: one or more monomers suitable for making the ophthalmic device; and a polymerizable high energy light absorbing compound of formula I:

wherein R 1 , R 2 and R 3 are independently H, C 1 -C 6 alkyl, C 5 -C 8 cycloalkyl, C 1 -C 6 alkoxy, aryl, aryloxy, halo, or —Y—P g ;
X is CR 4 R 5 , O, S, or NR 4 ;
R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently H, C 1 -C 6 alkyl, C 5 -C 8 cycloalkyl, or —Y—P g ;
Y is a linking group; and
P g is a polymerizable group comprising (meth)acrylate or (meth)acrylamide,

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is —Y—P g .

2. The ophthalmic device of claim 1 wherein the compound of formula I contains one —Y—P g group.

3. The ophthalmic device of claim 1 wherein R 1 is Y—P g .

4. The ophthalmic device of claim 1 wherein R 2 and R 3 are each H.

5. The ophthalmic device of claim 1 wherein R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each H.

6. The ophthalmic device of claim 1 wherein X is CH 2 , O, NH, or NCH 3 .

7. The ophthalmic device of claim 1 wherein Y comprises: C 1 -C 8 alkylene, alkyleneoxy, C 1 -C 8 oxaalkylene, C 1 -C 8 thiaalkylene, C 1 -C 8 alkylene-ester-C 1 -C 8 alkylene, C 1 -C 8 alkylene-amide-C 1 -C 8 alkylene, or C 1 -C 8 alkylene-amine-C 1 -C 8 alkylene.

8. The ophthalmic device of claim 1 wherein the polymerizable high energy light-absorbing compound is selected from the group consisting of
2-((1-amino-8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)ethyl methacrylate;
N-(2-((1-amino-8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)ethyl)methacrylamide;
N-(2-((1-amino-8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)ethyl)-N-methylmethacrylamide;
2-((5-amino-4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)ethyl methacrylate;
N-(2-((5-amino-4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)ethyl)methacrylamide;
N-(2-((5-amino-4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)ethyl)-N-methylmethacrylamide;
2-((5-amino-1-methyl-4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)ethyl methacrylate;
N-(2-((5-amino-1-methyl-4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)ethyl)methacrylamide;
N-(2-((5-amino-1-methyl-4-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)ethyl)-N-methylmethacrylamide;
2-((5-amino-4-oxochroman-6-yl)oxy)ethyl methacrylate;
N-(2-((5-amino-4-oxochroman-6-yl)oxy)ethyl)methacrylamide; or
N-(2-((5-amino-4-oxochroman-6-yl)oxy)ethyl)-N-methylmethacrylamide.

9. The ophthalmic device of claim 1 further comprising a second polymerizable high energy light absorbing compound.

10. The ophthalmic device of claim 9 wherein the second polymerizable high energy light absorbing compound is a UV absorbing compound.

11. The ophthalmic device of claim 10 wherein the UV absorbing compound comprises a compound of formula I, a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicyclic acid derivative, a benzoic acid derivative, a cinnamic acid derivative, a chalcone derivative, a dypnone derivative, a crotonic acid derivative, or mixtures thereof.

12. The ophthalmic device of claim 9 wherein the second polymerizable high energy light absorbing compound is 2-(2′-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole, (Z)-3-hydroxy-1-(naphthalen-2-yl)-3-(4-vinylphenyl) prop-2-en-1-one, 1-(2-amino-3-methoxyphenyl)-2-methylprop-2-en-1-one, or combinations thereof.

13. The ophthalmic device of claim 1 wherein the monomer suitable for making the ophthalmic device comprises a hydrophilic component, a silicone-containing component, or mixtures thereof.

14. The ophthalmic device of claim 1 that is a contact lens, a corneal onlay, a corneal inlay, an intraocular lens, or an overlay lens.

15. The ophthalmic device of claim 1 that is a hydrogel contact lens.

16. A method for making an ophthalmic device, the method comprising:
(a) providing a reactive mixture containing a compound of formula I:

wherein R 1 , R 2 and R 3 are independently H, C 1 -C 6 alkyl, C 5 -C 8 cycloalkyl, C 1 -C 6 alkoxy, aryl, aryloxy, halo, or —Y—P g ;
X is CR 4 R 5 O, S, or NR 4 ;
R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently H, C 1 -C 6 alkyl, C 5 -C 8 cycloalkyl, or —Y—P g ;
Y is a linking group; and
P g is a polymerizable group comprising (meth)acrylate or (meth)acrylamide,

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is —Y—P g ; and
one or more device forming monomers, and a radical initiator; and
(b) polymerizing the reactive mixture to form the ophthalmic device.

17. A silicone hydrogel contact lens that is a reaction product of a reactive mixture comprising: the polymerizable high energy light absorbing compound of formula I:

wherein R 1 , R 2 and R 3 are independently H, C 1 -C 6 alkyl, C 5 -C 8 cycloalkyl, C 1 -C 6 alkoxy, aryl, aryloxy, halo, or —Y—P g ;
X is CR 4 R 5 , O, S, or NR 4 ;
R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently H, C 1 -C 6 alkyl, C 5 -C 8 cycloalkyl, or —Y—P g ;
Y is a linking group; and
P g is a polymerizable group comprising (meth)acrylate or (meth)acrylamide,

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is —Y—P g ;
and one or more monomers suitable for making an ophthalmic device.

18. The silicone hydrogel contact lens of claim 17 wherein the contact lens has a contact angle of about 70° or less, a water content of at least 25 percent, and an oxygen permeability of at least 80 barrers.

19. The silicone hydrogel contact lens of claim 17 , wherein the reactive mixture further comprises a polyamide, an ultraviolet light absorber, a cross-linking agent, a diluent, or combinations thereof.

Assignees

• Johnson & Johnson Vision Care
• Johsnon & Johnson Vision Care Inc

Inventors

• Arnold Stephen C
• Mahadevan Shivkumar
• Maharvi Ghulam

Classifications

• C08F226/00

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen · CPC title

• C08F228/00

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur · CPC title

• A61F2002/1696

  Having structure for blocking or reducing amount of light transmitted, e.g. glare reduction · CPC title

• C08F283/12

  on to polysiloxanes · CPC title

• C08F290/068

  Polysiloxanes · CPC title