Transitions Optical, Inc.

Ppg Industries Ohio, Inc.

Terry A Kellar, Ii

Anil Kumar

Meng He

Forrest R Blackburn

Peter C Foller

Jiping Shao

Darrin R Dabideen

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.

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&#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.

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.

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&#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 liquid crystal cell including a first substrate having a first surface; a second substrate having a second surface, wherein the second surface of the second substrate is opposite and spaced apart from the first surface of the first substrate so as to define a region; and within the region defined by the first surface and the second surface, a liquid crystal material adapted to be at least partially ordered and at least one thermally reversible photochromic-dichroic compound adapted to be at least partially aligned and having an average absorption ratio greater than 2.3 in an activated state.

Polarizing, photochromic devices and methods of making the same

Provided is an optical element including:

Various non-limiting embodiments disclosed herein relate generally to photochromic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. Other non-limiting embodiments relate to photochromic-dichroic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. For example, one non-limiting embodiment provides a thermally reversible, photochromic compound adapted to have at least a first state and a second state, wherein the thermally reversible, photochromic compound has an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD. Another non-limiting embodiment provides a photochromic compound comprising: (a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by the formula&#x2014;[S]-[Q&#x2014;[S]]-[Q&#x2014;[S]]-[Q&#x2014;[S]]&#x2014;S&#x2014;P, which is described herein.

Various non-limiting embodiments disclosed herein relate generally to photochromic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. Other non-limiting embodiments relate to photochromic-dichroic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. For example, one non-limiting embodiment provides a thermally reversible, photochromic compound adapted to have at least a first state and a second state, wherein the thermally reversible, photochromic compound has an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD. Another non-limiting embodiment provides a photochromic compound comprising: (a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by the formula &#x2014;[S]&#x2014;[Q&#x2014;[S]]&#x2014;[Q&#x2014;[S]]&#x2014;[Q&#x2014;[S]]&#x2014;S&#x2014;P, which is described herein.

Various non-limiting embodiments disclosed herein relate generally to photochromic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. Other non-limiting embodiments relate to photochromic-dichroic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. For example, one non-limiting embodiment provides a thermally reversible, photochromic compound adapted to have at least a first state and a second state, wherein the thermally reversible, photochromic compound has an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD. Another non-limiting embodiment provides a photochromic compound comprising: (a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by the formula &#x2014;[S]-[Q-[S]]-[Q-[S]]-[Q-[S]]&#x2014;S&#x2014;P, which is described herein.

A security element connected to at least a portion of a substrate, the security element including an at least partial coating having a first state and a second state connected to at least a portion of the substrate, the at least partial coating being adapted to switch from a first state to a second state in response to at least actinic radiation, to revert back to the first state in response to thermal energy, and to linearly polarize at least transmitted radiation in at least one of the first state and the second state.

Growing community of inventors

Monroeville, PA, United States of America

Terry A Kellar, Ii