Transitions Optical, Inc.

Ppg Industries Ohio, Inc.

Darrin R Dabideen

Anil Kumar

Meng He

Terry A Kellar, Ii

Sujit Mondal

Ruisong Xu

Anu Chopra

Wenjing Xiao

Xiao-Man Dai

Robert W Walters

Massimiliano Tomasulo

Rachael L DeMeio

Huayun Yu

Matthew S Luchansky

Ryan Stayshich

Chien-Yang Chiu

Zachary Smith

Shengwen Yuan

Rachel L DeMeio

Barry R Havens

Nigel D Kidder-Wolff

Nick J Parise

Terry A Keller, Ii

Terry A Kellar

Suijit Mondal

Nick Parise

Terry A Ii Kellar

A method of preparing a low bubbling and low yellowing, high refractive index polyurethane or polythiourethane is provided. A method of evaluating an aromatic polyiso(thio)cyanate material, such as an aromatic diisocyanate, e.g., m-xylylene cyanate, is provided. The method evaluates transmittance in a sample of the isocyanate to determine if the aromatic polyiso(thio)cyanate material will lead to unacceptable bubbling or yellowing in a high refractive index or high Abbe number polymer composition.

Method of preparing low haze polymer compositions for use in high refractive index optical materials

Provided is a photochromic indolenaphthopyran compound having the skeletal structure of Formula (I): wherein Rand Reach independently have a steric bulk A, wherein at least one of Ror Rhas a steric bulk A of at least 0.6, Rand Reach independently have a Hammett σp value, and wherein the indolenaphthopyran compound has a calculated electronic steric factor of at least −3.3.

Indolonaphthopyrans

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 indeno fused phenanthrenopyran compounds represented by the following Formula (I). With some embodiments, the photochromic compounds represented by Formula (I) include at least one lengthening group (e.g., Rand/or Reach independently being a lengthening group) and the compounds of the present invention are photochromicdichroic compounds. The present invention also relates to photochromic compositions and photochromic articles, such as photochromic ophthalmic articles that include one or more photochromic compounds represented by Formula (I). 

Photochromic indeno fused phenanthrenopyran compounds

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being &#x2014;N, &#x2014;CN, &#x2014;COOR', &#x2014;CCR&#x2032;, &#x2014;C(R&#x2032;)C(R&#x2032;)R&#x2032;, &#x2014;OCOR&#x2032;, &#x2014;OCOOR&#x2032;, &#x2014;SR&#x2032;, &#x2014;OSOR&#x2032;&#x2033;, and/or CON(R&#x2032;)R&#x2032;, wherein each R&#x2032; is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R&#x2032;&#x2033; is &#x2014;CFor a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

Photochromic compounds

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being &#x2014;N, &#x2014;CN, &#x2014;COOR', &#x2014;CCR&#x2032;, &#x2014;C(R&#x2032;)C(R&#x2032;)R&#x2032;, &#x2014;OCOR&#x2032;, &#x2014;OCOOR&#x2032;, &#x2014;SR&#x2032;, &#x2014;OSOR&#x2033;&#x2032;, and/or &#x2014;CON(R&#x2032;)R&#x2032;, wherein each R&#x2032; is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R&#x2033;&#x2032; is &#x2014;CFor a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being &#x2014;N, &#x2014;CN, &#x2014;COOR', &#x2014;CCR&#x2032;, &#x2014;C(R&#x2032;)C(R&#x2032;)R&#x2032;, &#x2014;OCOR&#x2032;, &#x2014;OCOOR&#x2032;, &#x2014;SR&#x2032;, &#x2014;OSOR&#x2032;&#x2033;, and/or &#x2014;CON(R&#x2032;)R&#x2032;, wherein each R&#x2032; is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R&#x2033;&#x2032; is &#x2014;CFor a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

The present invention relates to photochromic articles that include a substrate and at least one photochromic material that is adapted to change from an unactivated form to an activated form by exposure to radiation substantially in the wavelength range from 380 to 450 nanometers when measured over a range of from 380 to 700 nanometers. The photochromic article is also adapted to retain at least 12 percent of the delta OD measured in the Outdoor Test when tested in the Behind the Windshield Test. The photochromic material can be selected from certain compounds including, for example, fluoranthenoxazines, naphthopyrans, phenanthropyrans, fluoranthenopyrans, and indenonaphthopyrans, which each have bonded thereto at least one chiral or achiral lengthening group that provides the photochromic compound with dichroic properties. The present invention also relates to methods of forming a photochromic article.

Photochromic articles that include photochromic-dichroic materials

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being &#x2014;N, &#x2014;CN, &#x2014;COOR', &#x2014;CCR&#x2032;, &#x2014;C(R&#x2032;)C(R&#x2032;)R&#x2032;, &#x2014;OCOR&#x2032;, &#x2014;OCOOR&#x2032;,&#x2014;SR&#x2032;, &#x2014;OSOR&#x2032;&#x2033;, and/or &#x2014;CON(R&#x2032;)R&#x2032;, wherein each R&#x2032; is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R&#x2032;&#x2033; is &#x2014;CFor a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being &#x2014;N, &#x2014;CN, &#x2014;COOR', &#x2014;CCR&#x2032;, &#x2014;C(R&#x2032;)C(R&#x2032;)R&#x2032;, &#x2014;OCOR&#x2032;, &#x2014;OCOOR&#x2032;, &#x2014;SR&#x2032;, &#x2014;OSOR&#x2032;&#x2033;, and/or &#x2014;CON(R&#x2032;)R&#x2032;, wherein each R&#x2032; is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R&#x2032;&#x2033; is &#x2014;CFor a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being &#x2014;N, &#x2014;CN, &#x2014;COOR', &#x2014;CCR&#x2032;, &#x2014;C(R&#x2032;)C(R&#x2032;)R&#x2032;, &#x2014;OCOR&#x2032;, &#x2014;OCOOR&#x2032;, &#x2014;SR&#x2032;, &#x2014;OSOR&#x2032;&#x2033;, and/or &#x2014;CON(R&#x2032;)R&#x2032;, wherein each R&#x2032; is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R&#x2032;&#x2033; is &#x2014;CFor a perfluorinated alkyl group having from 2 to 18 carbon atoms. The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

The present invention relates to compounds represented by the following Formula (II), Ring-A of Formula II can be, for example, an aryl group, and Q' and Q&#x2032;&#x2033; can each be independently selected from groups, such as, halogen, &#x2014;OH, &#x2014;CN, amine groups, amide groups, carboxylic acid ester groups, carboxylic acid groups, alkenyl groups, alkynyl groups, carbonate groups, sulfide groups, and sulfonic acid ester groups. The present invention also relates to photochromic compositions and photochromic articles that include one or more photochromic compounds such as represented by Formula II.

Indeno-fused ring compounds

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 naphthopyran compounds that include at least one compound represented by the following Formulas (I), (II), and (III): With reference to Formulas (I), (II), and (III), there is the proviso that: (i) at least one Ris a group L; and/or (ii) B and/or B' is substituted with at least one group L. The group L can be described as a lengthening group. The present invention also relates to photochromic-dichroic naphthopyran compounds and photochromic-dichroic articles containing such compounds.

Growing community of inventors

Pittsburgh, PA, United States of America

Darrin R Dabideen