Transitions Optical, Inc.

Ppg Industries, Inc.

Ppg Industries Ohio, Inc.

Johnson and Johnson Vision Care, Inc.

American Cyanamid Company

Barry Van Gemert

Anil Kumar

David B Knowles

Anu Chopra

Wenjing Xiao

Robert W Walters

Jerome M Lavanish

Shivkumar Mahadevan

Huayun Yu

Beon-Kyu Kim

Kevin J Stewart

Frank Molock

Jibing Lin

Clara E Nelson

Frank P Mallak

Clara M Nelson

Sidney B Richter

Robert A Smith

Jun Deng

Forrest R Blackburn

Massimiliano Tomasulo

Carol L Knox

Michael S Misura

Feng Wang

Elizabeth Ann Zezinka

Xiao-Man Dai

Stephen D Straight

Christopher D Selvig

James A Schwindeman

Victor A Montes

Jason Ryan Lewis

Patrick M Brown

Olga G Petrovskaia

Delbert G Kish

Kevin E Bancroft

Xiao Wenjing

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.

Ophthalmic devices comprising photochromic materials with reactive substituents

Ophthalmic devices comprising photochromic materials with reactive sub substituents

The present invention relates to indeno-fused naphthopyrans, and in particular indeno[2',3&#x2032;:3,4]naphtho[1,2-b]pyrans having certain groups bonded to the 3, 6, 7, 11, and 13 positions thereof. The indeno-fused naphthopyrans of the present invention have an ethylenically unsaturated group selected from (C-Calkyl)acrylate and (C-Calkyl)acrylamide, that is linked to the 11 position or 13 position thereof. The present invention also relates to photochromic articles and photochromic compositions containing such indeno-fused naphthopyrans.

Indeno-fused naphthopyrans having ethylenically unsaturated groups

The present invention relates to a method of making indeno-fused naphthol materials, that involves, with some embodiments, forming an indanone acid intermediate, represented by the following general Formula V, With Formula V, m is from 0 to 4, and Rfor each m, Rand Rcan each be independently selected from, for example, hydrogen and hydrocarbyl.

Method of making indeno-fused naphthol materials

The present invention relates to photochromic materials that include one or more indeno-fused naphthopyrans that have particular groups at the 7, 11, and 13 positions thereof, and at the position alpha to the oxygen of the pyran ring thereof. With some embodiments, hydrogen or an alkoxy group is bonded to the 7 position, an optionally substituted phenyl is bonded to the 11 position, two alkyl groups are bonded to the 13 position, and two optionally substituted phenyl groups are bonded to the position alpha to the oxygen of the pyran ring of the indeno-fused naphthopyran compound. The 13 position of the indeno-fused naphthopyrans is free of ether groups in which an ether oxygen is bonded to the 13 position, and hydroxyl. The present invention also relates to photochromic articles and compositions that include such indeno-fused naphthopyrans.

Photochromic materials that include indeno-fused naphthopyrans

The present invention relates to a method of making indeno-fused naphthol materials, that involves, with some embodiments, forming an indanone acid intermediate, which can be represented by the following general Formula V, With Formula V, m is from 0 to 4, and Rfor each m, Rand Rcan each be independently selected from, for example, hydrogen and hydrocarbyl. The present invention also relates to a method of making an indeno-fused naphthopyran that involves an indanone acid intermediate synthetic route.

Described are photochromic ocular devices such as contact lenses and intraocular lenses made of an organic polymeric material and at least one photochromic material capable upon exposure to actinic radiation to change from a less ultraviolet radiation absorbing unactivated form to a more ultraviolet radiation absorbing activated form. The photochromic ocular device is capable upon exposure to actinic radiation to exhibit a ratio of greater than 0.5:1.0 of increased ultraviolet radiation absorbance to increased visible radiation absorbance as measured in the Ultraviolet Photochromic Performance Test described herein.

Photochromic ocular devices

Described are contact lenses having photochromic materials within the central or pupillary area of the lens and methods for manufacturing such lenses. In one method, a photochromic amount of at least one photochromic material is added to the pupillary region of a casting mold containing a polymerizable monomer that can be at least partially cured before and/or after the addition. Another method involves providing an amount of polymerizable photochromic monomer for the pupillary region and an amount of polymerizable non-photochromic monomer for the remainder of the contact lens in a casting mold. The photochromic and non-photochromic monomers can differ by their degree of polymerization, viscosity and/or density.

Photochromic contact lenses and methods of manufacturing

Photochromic materials comprising indeno-fused naphthopyrans having a first electron-withdrawing substituent and, in certain non-limiting embodiments, a second electron-withdrawing substituent are disclosed. The photochromic materials according to the various embodiments may display faster fade rates, bathochromic shift, and higher performance ratings compared to comparable indeno-fused naphthopyrans without the electron-withdrawing substituents. Photochromic compositions and articles, such as optical elements, incorporating the photochromic materials are also disclosed.

Photochromic materials having electron-withdrawing substituents

Various non-limiting embodiments of the present disclosure relate to photochromic materials comprising a reactive substituent. For example, the present disclosure contemplates 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 or an electrophilic moiety. Other non-limiting embodiments of the present disclosure relate to photochromic articles, compositions, and methods of making the photochromic articles, wherein the photochromic articles and compositions comprise the photochromic naphthopyrans described herein.

Photochromic materials with reactive substituents

Various non-limiting embodiments disclosed herein related to photochromic materials comprising the reaction product of (a) at least one ring-opening cyclic monomer, and (b) a photochromic initiator. Other non-limiting embodiments related to photochromic materials represented by: wherein S' comprises the at least one ring-opened cyclic monomer as set forth herein. Other non-limiting embodiments related to photochromic compositions, optical elements, and methods of inhibiting migration of a photochromic material in a polymeric material using the photochromic materials disclosed herein. Methods of making such photochromic materials, compositions, and optical elements are also disclosed.

Photochromic materials derived from ring-opening monomers and photochromic initiators

Described are photochromic articles that include a substrate, a temperature dependent reducing amount of at least one organic photochromic material (b) that changes from more absorbing to less absorbing of radiation in its activating spectral absorbance as the temperature increases from 10&#xb0; C. to 35&#xb0; C. and at least one other photochromic material (c) that is different from photochromic material (b). In the article, photochromic material (b) is interposed between photochromic material (c) and a source of activating radiation. The photochromic article demonstrates a more consistent photochromic response, for example, an optical density response loss of 50 percent or less over a temperature range of from 10&#xb0; C. to 35&#xb0; C. as measured in the Photochromic Temperature Dependence Test. Methods for producing the aforedescribed articles are also disclosed.

Photochromic articles with reduced temperature dependency and methods for preparation

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Murrysville, PA, United States of America

Barry Van Gemert