Ophthalmic devices comprising photochromic materials with reactive substituents

Patent metadata

Field	Value
Publication number	US-11256002-B2
Application number	US-201816224875-A
Country	US
Kind code	B2
Filing date	Dec 19, 2018
Priority date	Apr 8, 2005
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

Various non-limiting embodiments of the present disclosure relate to ophthalmic devices comprising photochromic materials comprising a reactive substituent. For example, the present disclosure contemplates ophthalmic devices comprising photochromic materials, such as photochromic naphthopyrans and indeno-fused naphthopyrans having a reactive substituent comprising a reactive moiety linked to the photochromic naphthopyran by one or more linking groups. In certain non-limiting embodiments, the reactive moiety comprises a polymerizable moiety. In other non-limiting embodiments, the reactive moiety comprises a nucleophilic moiety. Other non-limiting embodiments of the present disclosure relate to methods of making the photochromic ophthalmic device, wherein the photochromic ophthalmic devices comprise the photochromic naphthopyrans described herein.

First claim

We claim:

1. A method of making a photochromic ophthalmic device made of a polymeric material, the method comprising connecting a photochromic material to at least a portion of the polymeric material, wherein the photochromic material comprises:
a photochromic naphthopyran; and
at least one reactive substituent bonded to the photochromic naphthopyran, wherein each reactive substituent is independently represented by one of:
-A-D-E-G-J;
-G-E-G-J;
-D-E-G-J;
-A-D-J;
-D-G-J; and
-D-J;

wherein:
(i) each -A- is independently —C(═O)—, —OC(═O)—, —NHC(═O)—, or —CH 2 —;
(ii) each -D- is independently:
(a) a diamine residue or a derivative thereof, said diamine residue being an aliphatic diamine residue, a cyclo aliphatic diamine residue, a diazacycloalkane residue, an azacyclo aliphatic amine residue, a diazacrown ether residue, or an aromatic diamine residue, wherein a first amine nitrogen of said diamine residue forms a bond with -A- or the photochromic naphthopyran, and a second amine nitrogen of said diamine residue forms a bond with -E-, -G-, or -J; or
(b) an amino alcohol residue or a derivative thereof, said amino alcohol residue being an aliphatic amino alcohol residue, a cyclo aliphatic amino alcohol residue, an azacyclo aliphatic alcohol residue, a diazacyclo aliphatic alcohol residue, or an aromatic amino alcohol residue, wherein an amine nitrogen of said amino alcohol residue forms a bond with -A- or the photochromic naphthopyran, and an alcohol oxygen of said amino alcohol residue forms a bond with -E-, -G-, or -J, or said amine nitrogen of said amino alcohol residue forms a bond with -E-, -G-, or -J, and said alcohol oxygen of said amino alcohol residue forms a bond with -A- or the photochromic naphthopyran;

(iii) each -E- is independently a dicarboxylic acid residue or a derivative thereof, said dicarboxylic acid residue being an aliphatic dicarboxylic acid residue, cycloaliphatic dicarboxylic acid residue, or an aromatic dicarboxylic acid residue, wherein a first carbonyl group of said dicarboxylic acid residue forms a bond with -G- or -D-, and a second carbonyl group of said dicarboxylic acid residue forms a bond with -G-;
(iv) each -G- is independently:
(a) —[(OC 2 H 4 ) x (OC 3 H 6 ) y (OC 4 F 18 ) z ]—O—,
wherein x, y, and z, are each independently a number between 0 and 50, and the sum of x, y, and z ranges from 1 to 50; or

(b) a polyol residue or a derivative thereof, said polyol residue being an aliphatic polyol residue, a cyclo aliphatic polyol residue, and an aromatic polyol residue, wherein a first polyol oxygen of said polyol residue forms a bond with -E-, -D-, or the photochromic naphthopyran, and a second polyol oxygen of said polyol residue forms a bond with -E- or -J; and

(v) each -J is independently a group comprising a reactive moiety or residue thereof; or -J is hydrogen, provided that if -J is hydrogen, -J is bonded to an oxygen of group -D- or -G-, forming a reactive moiety.

2. The method according to claim 1 , wherein said connecting comprises incorporating the photochromic material into the at least a portion of the polymeric material by at least one of blending the photochromic material with the at least a portion of the polymeric material and bonding the photochromic material to the at least a portion of the polymeric material.

3. The method according to claim 2 , wherein the photochromic material is bonded by co-polymerizing the photochromic material with the at least a portion of the polymeric material.

4. The method according to claim 1 , wherein said connecting the photochromic material into the at least a portion of the polymeric material comprises casting-in-place the photochromic material and the at least a portion of the polymeric material.

5. The method according to claim 1 , wherein said connecting the photochromic material to the at least a portion of the polymeric material, comprises applying an at least partial coating comprising the photochromic material to the at least a portion of the polymeric material.

6. The method according to claim 5 , wherein applying the at least partial coating comprising the photochromic material to the at least a portion of the polymeric material comprises one of dip coating, spin coating, roll coating, spray coating, curtain coating, and in-mold casting.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Xiao Wenjing
• Van Gemert Barry
• Mahadevan Shivkumar
• Molock Frank

Classifications

• G03C1/73

  containing organic compounds · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• G02B5/23

  Photochromic filters · CPC title

• Y10T428/31935

  Ester, halide or nitrile of addition polymer · CPC title

• G02C7/04

  Contact lenses for the eyes (disinfection or sterilisation of contact lenses A61L12/00) · CPC title