Transitions Optical, Inc.

Johnson and Johnson Vision Care, Inc.

Wenjing Xiao

Anu Chopra

Huayun Yu

Barry Van Gemert

Beon-Kyu Kim

David B Knowles

Jun Deng

Stephen D Straight

Victor A Montes

Frank F Molock, Jr

Robert W Walters

Shivkumar Mahadevan

Sujit Mondal

Darrin R Dabideen

Frank Molock

Massimiliano Tomasulo

Xiao-Man Dai

Anil Kumar

Meng He

Ruisong Xu

Elizabeth Ann Zezinka

Jason Ryan Lewis

Feng Wang

M Frank Haley

Michael Frank Haley

Yunyi Lu

Brian Shaughnessy

Joseph D Turpen

An-Hung Yeh

Kevin E Bancroft

Nicholas J Parise

Emily Amond

Nick J Parise

Eric Spitler

Brian R Stepp

Suijit Mondal

Nick Parise

The present invention relates to a photochromic article that includes a substrate and a photochromic layer formed from a curable photochromic composition. The photochromic composition includes a polyol component that includes a polycarbonate diol, an isocyanate component that includes an unblocked polyfunctional isocyanate and/or a blocked polyfunctional isocyanate, and at least one photochromic compound. The equivalents ratio of blocked/unblocked isocyanate equivalents of the isocyanate component to hydroxyl equivalents of the polyol component is at least 5:1. The photochromic article exhibits a T(Fade Half Life) at 23° C. of less than or equal to 70 seconds.

Photochromic article

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

A photochromic compound including a core skeletal structure represented by the following Formula (I), 

Photochromic indeno-fused naphthopyran compounds with reduced temperature dependence

The present invention relates to photochromic compounds, such as thienochromene compounds represented by the following Formulas (1a) and/or (1b). The present invention also relates to photochromic compositions and articles containing one or more such photochromic thienochromene compounds. 

Photochromic thienochromene compounds

Ophthalmic devices comprising photochromic materials with reactive sub substituents

The present invention provides ophthalmic devices comprising at least one photochromic material which is an indeno-fused naphthopyran having a pi-conjugation extending group bonded to the 11-position of the indeno-fused naphthopyran, the pi-conjugation extending group having at least one pendent halo-substituted group bonded thereto. The pi-conjugation extending group extends the pi-conjugation system of said indeno-fused naphthopyran. The 13-position of the indeno-fused naphthopyran is substantially free of spiro-substituents. The invention further provides photochromic materials of specified structure, photochromic compositions, photochromic articles and optical elements that include the photochromic materials. Other non-limiting embodiments relate to methods of making the ophthalmic devices comprising photochromic materials.

Photochromic materials having extended pi-conjugated systems and compositions and articles including the same

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

Described herein are compounds generally comprising an indeno[2',3&#x2032;:3,4]naptho[1,2-b]pyran structure. Such compounds may be useful for their photochromic properties, and be used in certain photochromic compositions. Such compositions may further comprise other photochromic compositions and/or materials. Additionally, such compounds and/or compositions may be suitable for preparing certain photochromic articles. Also described herein are methods for preparing certain photochromic compounds, compositions, and articles.

Photochromic compounds and compositions

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

Described herein are compounds generally comprising an indeno[2',3&#x2032;:3,4]naptho[1,2-b]pyran structure. Such compounds may be useful for their photochromic properties, and be used in certain photochromic compositions. Such compositions may further comprise other photochromic compositions and/or materials. Additionally, such compounds and/or compositions may be suitable for preparing certain photochromic articles.

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.

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Murrysville, PA, United States of America

Wenjing Xiao