Photochromic articles that include photochromic-dichroic materials

Patent metadata

Field	Value
Publication number	US-9334439-B2
Application number	US-201313835413-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Mar 15, 2013
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

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.

First claim

What is claimed is:

1. A photochromic article comprising:
(a) a substrate; and
(b) at least one photochromic material 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, said photochromic article being adapted to retain at least 12 percent of the delta OD measured in the Outdoor Test when tested in the Behind the Windshield Test,
wherein photochromic material (b) is chosen from at least one of,
(1) a photochromic material chosen from at least one fluoranthenoxazine represented by the following Formula (I),

wherein for Formula (I),
(a) R 1 is chosen from hydrogen, C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, phen(C 1 -C 4 )alkyl, naphth(C 1 -C 4 )alkyl, allyl, acrylyloxy(C 2 -C 6 )alkyl, methacrylyloxy(C 2 -C 6 )alkyl, C 2 -C 4 acyloxy(C 2 -C 6 )alkyl, carboxy(C 2 -C 6 )alkyl, cyano(C 2 -C 6 )alkyl, hydroxy(C 2 -C 6 )alkyl, triarylsilyl, triarylsilyloxy, tri(C 1 -C 6 )alkylsilyl, tri(C 1 -C 6 )alkylsilyloxy, tri(C 1 -C 6 )alkoxysilyl, tri(C 1 -C 6 )alkoxysilyloxy, di(C 1 -C 6 )alkyl(C 1 -C 6 alkoxy)silyl, di(C 1 -C 6 )alkyl(C 1 -C 6 alkoxy)silyloxy, di(C 1 -C 6 )alkoxy(C 1 -C 6 alkyl)silyl, di(C 1 -C 6 )alkoxy(C 1 -C 6 alkyl)silyloxy, C 1 -C 6 alkoxy(C 2 -C 4 )alkyl or (C 2 H 4 O) r CH 3 , wherein r is an integer from 1 to 6,
(b) R 2 is chosen from C 1 -C 5 alkyl, C 1 -C 5 alkoxy, nitro, cyano, C 1 -C 8 alkoxycarbonyl, C 1 -C 4 acyloxy, halo, C 1 -C 4 monohaloalkyl or C 1 -C 4 polyhaloalkyl; said halo substituents being chloro, fluoro, iodo or bromo and q is 0, 1 or 2,
(c) R 3 and R 4 are each independently chosen from C 1 -C 5 alkyl, benzyl, phenyl, mono- or di-substituted phenyl, said phenyl substituents being C 1 -C 5 alkyl or C 1 -C 5 alkoxy; or R 3 and R 4 taken together form a group chosen from a cyclic ring of from 5 to 8 carbon atoms which includes the spiro carbon atom,
(d) R 5 is chosen from hydrogen, —CH 2 Q and —C(O)W, wherein Q is halogen, hydroxy, benzoyloxy, C 1 -C 6 alkoxy, C 2 -C 6 acyloxy, amino, C 1 -C 6 mono-alkylamino, C 1 -C 6 dialkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl, triarylsilyl, triarylsilyloxy, tri(C 1 -C 6 )alkylsilyl, tri(C 1 -C 6 )alkylsilyloxy, tri(C 1 -C 6 )alkoxysilyl, tri(C 1 -C 6 )alkoxysilyloxy, di(C 1 -C 6 )alkyl(C 1 -C 6 alkoxy)silyl, di(C 1 -C 6 )alkyl(C 1 -C 6 alkoxy)silyloxy, di(C 1 -C 6 )alkoxy(C 1 -C 6 alkyl)silyl, di(C 1 -C 6 )alkoxy(C 1 -C 6 alkyl)silyloxy, or the group, —OCH(R 8 )Z; W is the group, —OCH(R 8 )Z, or an unsubstituted, mono-substituted, or di-substituted heterocyclic ring containing 5 to 6 ring atoms, which ring includes as the hetero atom a nitrogen atom alone or one additional hetero atom of nitrogen or oxygen; wherein Z is —CN, —CF 3 , halogen, —C(O)R 8 , or —COOR 8 , R 8 is hydrogen or C 1 -C 6 alkyl; said heterocyclic ring substituents being chosen from C 1 -C 6 alkyl or C 1 -C 6 alkoxy; or W is —OR 9 or wherein R 9 is chosen from hydrogen, allyl, C 1 -C 6 alkyl, phenyl, mono(C 1 -C 6 )alkyl substituted phenyl, mono(C 1 -C 6 )alkoxy-substituted phenyl, phenyl(C 1 -C 3 )alkyl, mono(C 1 -C 6 )alkyl substituted phenyl(C 1 -C 3 )alkyl, mono(C 1 -C 6 )alkoxy substituted phenyl(C 1 -C 3 )alkyl, C 1 -C 6 alkoxy(C 2 -C 4 )alkyl, or C 1 -C 6 haloalkyl; and R 10 and R 11 are each independently chosen from hydrogen, C 1 -C 6 alkyl, C 5 -C 7 cycloalkyl, phenyl, mono- or di-substituted phenyl, or R 10 and R 11 together with the nitrogen atom form a mono- or di-substituted or unsubstituted heterocyclic ring containing from 5 to 6 ring atoms, which ring includes as the hetero atom said nitrogen atom alone or one additional hetero atom of nitrogen or oxygen, said phenyl and heterocyclic ring substituents being C 1 -C 6 alkyl or C 1 -C 6 alkoxy, and each of said halogen or halo groups in this part (d) being fluoro or chloro, and
(e) each R 6 and R 7 is independently chosen for each occurrence from aryl, mono(C 1 -C 6 )alkoxyaryl, di(C 1 -C 6 )alkoxyaryl, mono(C 1 -C 6 )alkylaryl, di(C 1 -C 6 )alkylaryl, bromoaryl, chloroaryl, fluoroaryl, C 3 -C 7 cycloalkylaryl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyloxy, C 3 -C 7 cycloalkyloxy(C 1 -C 6 )alkyl, C 3 -C 7 cycloalkyloxy(C 1 -C 6 )alkoxy, aryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkoxy, aryloxy, aryloxy(C 1 -C 6 )alkyl, aryloxy(C 1 -C 6 )alkoxy, mono- or di(C 1 -C 6 )alkylaryl(C 1 -C 6 )alkyl, mono- or di(C 1 -C 6 )alkoxyaryl(C 1 -C 6 )alkyl, mono- or di(C 1 -C 6 )alkylaryl(C 1 -C 6 )alkoxy, mono- or di(C 1 -C 6 )alkoxyaryl(C 1 -C 6 )alkoxy, amino, mono(C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, diarylamino, N—(C 1 -C 6 )alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrryl, C 1 -C 6 alkyl, C 1 -C 6 bromoalkyl, C 1 -C 6 chloroalkyl, C 1 -C 6 fluoroalkyl, C 1 -C 6 alkoxy, mono(C 1 -C 6 )alkoxy(C 1 -C 4 )alkyl, acryloxy, methacryloxy, bromo, chloro or fluoro; and q is independently chosen for each occurrence form the integer 0, 1, or 2,
provided that for Formula (I) at least one of and less than all of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is in each case independently an L-Group as defined below;
(2) a photochromic material chosen from at least one naphthopyran represented by the following Formula (II),

wherein for Formula (II),
(a) R 12 is hydrogen or a C 1 -C 6 alkyl,
(b) R 13 is hydrogen or the group, —C(O)J, J being —OR 15 or —N(R 10 )R 11 , wherein R 15 is hydrogen, allyl, C 1 -C 6 alkyl, phenyl, C 1 -C 6 monoalkyl substituted phenyl, C 1 -C 6 monoalkoxy substituted phenyl, phenyl(C 1 -C 3 )alkyl, C 1 -C 6 monoalkyl substituted phenyl(C 1 -C 3 )alkyl, C 1 -C 6 monoalkoxy substituted phenyl(C 1 -C 3 )alkyl, C 1 -C 6 alkoxy(C 2 -C 4 )alkyl, or C 1 -C 6 monohaloalkyl, and wherein R 10 and R 11 are the same as described hereinbefore in (1)(d), and said halo substituent being chloro or fluoro,
(c) R 14 is —OR 9 , —N(R 10 )R 11 , wherein R 9 , R 10 and R 11 are the same as described hereinbefore in (1)(d), or the group, —C(O)V; wherein V is C 1 -C 6 alkyl, phenyl, C 1 -C 6 mono- or C 1 -C 6 di-alkyl substituted phenyl, C 1 -C 6 mono- or C 1 -C 6 di-alkoxy substituted phenyl, C 1 -C 6 alkoxy, phenoxy, C 1 -C 6 mono- or C 1 -C 6 di-alkyl substituted phenoxy, C 1 -C 6 mono- or C 1 -C 6 di-alkoxy substituted phenoxy, C 1 -C 6 alkylamino, phenylamino, C 1 -C 6 mono- or C 1 -C 6 di-alkyl substituted phenylamino, or C 1 -C 6 mono- or C 1 -C 6 di-alkoxy substituted phenylamino, and said halo substituent being chloro, fluoro or bromo, provided that either R 12 or R 13 is hydrogen; and
(d) B and B′ are each independently chosen from,
(i) mono-T-substituted phenyl, wherein the group T is represented by the formula,
-G[(OC 2 H 4 ) x (OC 3 H 6 ) y (OC 4 H 8 ) z ]G′

[(OC 2 H 4 ) x (OC 3 H 6 ) y (OC 4 H 8 ) z ]G′

wherein -G being chosen from —C(O)— or —CH 2 —, G′ being chosen from C 1 -C 3 alkoxy or a polymerizable group, x, y and z each being independently chosen from a number between 0 and 50, and the sum of x, y and z being between 2 and 50,
(ii) an unsubstituted, mono-, di-, or tri-substituted aryl group, phenyl or naphthyl,
(iii) 9-julolidinyl or the unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl and het

Assignees

• Transitions Optical Inc

Inventors

• Demeio Rachael L
• Kumar Anil
• He Meng
• Dabideen Darrin R
• Mondal Sujit

Classifications

• C09K2211/1033

  with oxygen · CPC title

• G03C1/73

  containing organic compounds · CPC title

• G02B5/23 Primary

  Photochromic filters · CPC title

• G02B1/10

  Optical coatings produced by application to, or surface treatment of, optical elements (G02B1/08 takes precedence) · CPC title

• B60J3/007

  Sunglare reduction by coatings, interposed foils in laminar windows, or permanent screens (layered glass products B32B17/00; process of coating windows C03C17/00) · CPC title