# US 2013/0252000 A1 · Eyewear including nitrophenyl functionalized boron pyrromethene dye for neutralizing laser threat

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- Number: US 2013/0252000 A1
- Document ID: US20130252000A1
- Status: Published application
- Kind: A1
- Application number: 13/426,491
- Filed: 2012-03-21
- Published: 2013-09-26
- Earliest claimed: 2012-03-21
- Assignees: Revision Military Inc.
- Inventors: Larry Takiff; Kevin M. Bardon; Charles Lysogorski; Oliver Pentenrieder
- Web page: https://patentgrep.com/patent/US20130252000A1

## CPC

- G02B 5/223: {containing organic substances, e.g. dyes, inks or pigments}
- C07F 5/022: {without C-boron linkages}
- C09B 23/0008: {substituted on the polymethine chain}
- C09B 23/04: one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
- C09B 57/10: Metal complexes of organic compounds not being dyes in uncomplexed form
- C09B 69/105: {containing a methine or polymethine dye}
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- C08K 5/3415: Five-membered rings
- Y10T 428/31507: Of polycarbonate
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The embodiments described herein generally relate to compositions and articles including dye compounds having desirable optical properties, and related methods. In some cases, the compositions and articles may possess advantageous optical properties, including various degrees of absorbance, emission, and/or transmission at particular wavelengths or ranges of wavelength. Embodiments described herein may be useful as optical filters in protective eyewear applications.

## Claims

### Claim 1

An article, comprising:
an optical filter including a substantially optically transparent polymer; and
a boron pyrromethene compound associated with the polymer, wherein the boron pyrromethene compound comprises a nitro group.

### Claim 2 (depends on 1)

An article as in claim 1, wherein the boron pyrromethene compound is dispersed on or within the polymer or formed as a coating on the polymer.

### Claim 3

(canceled)

### Claim 4 (depends on 1)

An article as in claim 1, wherein the boron pyrromethene compound has a maximum absorption peak between about 400 nm and about 800 nm.

### Claim 5 (depends on 1)

An article as in claim 1, wherein the boron pyrromethene compound has a maximum absorption peak at about 532 nm.

### Claim 6

(canceled)

### Claim 7 (depends on 1)

An article as in claim 1, wherein the boron pyrromethene compound has the following structure,
wherein:
each R1-R6 can be the same or different and each is hydrogen, halo, acyl, carboxyl, cyano, nitro, sulfonate, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, any of which is optionally substituted; and any two of R1-R6 can be joined to form a ring, optionally substituted;
X is N or CR7, wherein R7 is hydrogen, halo, acyl, carboxyl, cyano, nitro, sulfonate, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, any of which is optionally substituted; and
Y1 and Y2 can be the same or different and each is halo, acyl, carboxyl, cyano, nitro, sulfonate, any of which is optionally substituted; or Y1 and Y2 are joined to form a ring, optionally substituted.

### Claim at position 8

8-13. (canceled)

### Claim 14 (depends on 7)

An article as in claim 7, wherein R7 is an aryl group substituted with at least one nitro group.

### Claim 15 (depends on 14)

An article as in claim 14, wherein Y1 and Y2 are each fluoro.

### Claim 16 (depends on 1)

An article as in claim 1, wherein the substantially optically transparent polymer is polycarbonate.

### Claim at position 12

17-18. (canceled)

### Claim 19 (depends on 1)

An article as in claim 1, wherein the optical filter is included in eyewear.

### Claim 20 (depends on 19)

An article as in claim 19, wherein the eyewear includes a lens, goggle, eyeglasses, or visor.

### Claim at position 15

21-23. (canceled)

### Claim 24

A composition, comprising:
a compound having the following structure,
wherein:
each R1-R6 can be the same or different and each is hydrogen, halo, acyl, carboxyl, cyano, nitro, sulfonate, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, any of which is optionally substituted; and any two of R1-R6 can be joined to form a ring, optionally substituted;
X is N or CR7, wherein R7 is hydrogen, halo, acyl, carboxyl, cyano, nitro, sulfonate, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, any of which is optionally substituted; and
Y1 and Y2 can be the same or different and each is halo, acyl, carboxyl, cyano, nitro, sulfonate, any of which is optionally substituted; or Y1 and Y2 are joined to form a ring, optionally substituted,
provided that the compound includes at least one electron-withdrawing group.

### Claim 25 (depends on 24)

A composition as in claim 24, wherein the electron-withdrawing group is halo, acyl, carboxyl, cyano, nitro, or sulfonate.

### Claim 26 (depends on 24)

A compound as in claim 24, wherein the electron-withdrawing group is nitro.

### Claim 27 (depends on 24)

A composition as in claim 24, wherein:
R1, R2, R3, R4, R5, and R6 are each independently alkyl;
X is CR7; and
Y1 and Y2 are each halo.

### Claim at position 20

28-33. (canceled)

### Claim 34 (depends on 24)

A composition as in claim 24, wherein R7 is an aryl group substituted with at least one nitro group.

### Claim 35 (depends on 34)

A composition as in claim 34, wherein Y1 and Y2 are each fluoro.

### Claim 36 (depends on 24)

A composition as in claim 24, wherein the compound has the following structure,

### Claim 37 (depends on 24)

A composition as in claim 24, wherein the compound has the following structure,

### Claim 38 (depends on 24)

A composition as in claim 24, wherein the compound has the following structure,

### Claim 39 (depends on 24)

A composition as in claim 24, wherein the compound has the following structure,