Polymerizable absorbers of UV and high energy visible light

Patent metadata

Field	Value
Publication number	US-11046636-B2
Application number	US-201916398722-A
Country	US
Kind code	B2
Filing date	Apr 30, 2019
Priority date	Jun 29, 2018
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

Described are polymerizable high energy light absorbing compounds of formula I:

Wherein Y, Pg, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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. A compound of formula I:

wherein:
Y is a linking group;
P g is a polymerizable group;
R 1 is H or C 1 -C 6 alkyl;
R 2 and R 3 are independently C 1 -C 6 alkyl or cycloalkyl;
R 4 is C 1 -C 6 alkyl; and
R 5 and R 6 are independently H or C 1 -C 6 alkyl.

2. The compound of claim 1 wherein R 1 is H.

3. The compound of claim 1 wherein R 5 and R 6 are independently H or methyl.

4. The compound 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.

5. The compound of claim 1 wherein P g comprises: styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.

6. The compound of claim 1 wherein R 2 , R 3 , and R 4 are independently C 1 -C 3 alkyl.

7. A compound of claim 1 that is:
2-(4-acetyl-3-amino-2,6-dimethoxyphenoxy)ethyl methacrylate;
2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)thio)ethyl methacrylate;
2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)(methyl)amino)ethyl methacrylate;
2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)amino)ethyl methacrylate;
N-(2-(4-acetyl-3-amino-2,6-dimethoxyphenoxy)ethyl)methacrylamide;
N-(2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)thio)ethyl)methacrylamide;
N-(2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)amino)ethyl)methacrylamide;
N-(2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)(methyl)amino)ethyl)methacrylamide;
N-(2-(4-acetyl-3-amino-2,6-dimethoxyphenoxy)ethyl)acrylamide;
N-(2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)thio)ethyl)acrylamide;
N-(2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)amino)ethyl)acrylamide;
N-(2-((4-acetyl-3-amino-2,6-dimethoxyphenyl)(methyl)amino)ethyl)acrylamide
3-(4-acetyl-3-amino-2,6-dimethoxyphenyl)propyl methacrylate
N-(3-(4-acetyl-3-amino-2,6-dimethoxyphenyl)propyl)methacrylamide
4-acetyl-3-amino-2,6-dimethoxyphenethyl methacrylate; or
N-(4-acetyl-3-amino-2,6-dimethoxyphenethyl)methacrylamide.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Maharvi Ghulam
• Mahadevan Shivkumar
• Arnold Stephen C
• Martin Patricia
• Sonoda Leilani K
• Sinha Dola

Classifications

• C07C225/22 Primary

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07C69/738 Primary

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title

• C08F290/068

  Polysiloxanes · CPC title

• C08K5/3475

  condensed with carbocyclic rings · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title