ES2656823T3 - Compuestos fotocrómicos - Google Patents
Compuestos fotocrómicos Download PDFInfo
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- ES2656823T3 ES2656823T3 ES11001431.3T ES11001431T ES2656823T3 ES 2656823 T3 ES2656823 T3 ES 2656823T3 ES 11001431 T ES11001431 T ES 11001431T ES 2656823 T3 ES2656823 T3 ES 2656823T3
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- phenyl
- naphtho
- pyran
- piperidin
- indene
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- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3016—Polarising elements involving passive liquid crystal elements
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
Un compuesto fotocrómico: (I) que comprende: (A) al menos un grupo fotocrómico seleccionado entre un pirano, una oxazina y un fúlgido; y (B) al menos un agente de alargamiento unido a al menos un grupo fotocrómico, en donde el al menos un agente de alargamiento se selecciona entre: (1) 4-(4-fluoro-fenoxicarboniloxi)-piperidin-1-ilo; (2) 4-(bifenil-4-carboniloxi)-piperidin-1-ilo; (3) 4-(naftalen-2-carboniloxi)-piperidin-1-ilo; (4) 4-(4-pentadecafluoroheptiloxi-fenilcarbamoil)-benciloxi; (5) 4-(3-piperidin-4-il-propil)-piperidin-1-ilo; (6) éster de bis-[1-nombre del PC]-piperidin-4-ilo] del ácido bifenil-4,4'-dicarboxílico o (II) seleccionado entre: (a) 3-fenil-3-(4-(4-piperidinopiperidino)fenil)-13,13-dimetil-indeno[2',3':3,4]nafto[1,2-b]pirano; (b) 3-fenil-3-(4-(4-fenilpiperazina)fenil)-13,13-dimetil-indeno[2',3':3,4]nafto[1,2-b]pirano; (c) 3-fenil-3-(4-pirrolidin-1-il-fenil)-13,13-dimetil-6-metoxi-7-(4-fenil-piperazin-1-il)indeno[2',3':3,4]nafto[1,2- b]pirano; (d) 3-fenil-3-(4-pirrolidin-1-il-fenil)-13,13-dimetil-6-metoxi-7-([1,4']bipiperidinil-1``-il)indeno[2',3':3,4]nafto[1,2- b]pirano; (e) 3-fenil-3-(4-([1,4']bipiperidinil-1'-il)fenil)-13,13-dimetil-6-metoxi-7-([1,4']bipiperidinil-1'- il)indeno[2',3':3,4]nafto[1,2-b]pirano; (f) 3-fenil-3-(4-([1,4']bipiperidinil-1'-il)fenil)-13,13-dimetil-6-metoxi-7-(4-bencilpiperidin-1-il)indeno[2',3':3,4] nafto[1,2-b]pirano; (g) 3-fenil-3-(4-([1,4']bipiperidinil-1'-il)fenil)-13,13-dimetil-6-metoxi-7-(piperadin-1-il)indeno[2',3':3,4]nafto[1,2- b]pirano; (h) 3-fenil-3-(4-(4-fenil-piperazin-1-il)fenil)-13,13-dimetil-6-metoxi-7-(4-fenil-piperazin-1- il)indeno[2',3':3,4]nafto[1,2-b]pirano; (i) 1,3,3-trimetil-6'-(4-etoxicarbonil)-piperidin-1-il)-espiro[indolina-2,3'-3H-nafto[2,1-b][1,4]oxazina].
Description
(xiv) grupos R1 inmediatamente adyacentes junto a un grupo representado por una de las Fórmulas vii, viii y ix:
5 en donde
(A) W y W’ se seleccionan independientemente en cada ocasión entre -O-, -N(X7)-, -C(X14)-, -C(X17)-, (en donde X7, X14 y X17 son como se han expuesto anteriormente),
(B) X14, X15 y X17 son como se ha expuesto anteriormente y 10 (C) q es un número entero seleccionado entre 0, 1, 2, 3 y 4.
Otra realización no limitante proporciona un compuesto fotocrómico que comprende:
(a) al menos un grupo fotocrómico seleccionado entre un pirano, una oxazina y un fúlgido; y
15 (b) al menos un agente de alargamiento (L) unido al al menos un grupo fotocrómico, en donde el al menos un agente de alargamiento se selecciona entre uno de los siguientes compuestos enumerados (y representados gráficamente) a continuación en la Tabla I.
Tabla I:
- (1) 4-(4-fluoro-fenoxicarboniloxi)-piperidin-1-ilo
- (2) 4-(bifenil-4-carboniloxi)-piperidin-1-ilo
- imagen9
- (3) 4-(naftalen-2-carboniloxi)-piperidin-1-ilo
- (4) 4-(4-pentadecafluoroheptiloxi-fenilcarbamoil)-benciloxi
- (5) 4-(3-piperidin-4-il-propil)-piperidin-1-ilo
- (6) éster bis-[1-nombre del PC]-piperidin-4-ílico] del ácido bifenil4,4’-dicarboxílico
Otra realización no limitante desvelada en el presente documento proporciona un compuesto fotocrómico representado por la Fórmula II:
En referencia a la Fórmula II, A es un anillo aromático o un anillo aromático condensado seleccionado entre: nafto, benzo, fenantro, fluoranteno, anteno, quinolino, tieno, furo, indolo, indolino, indeno, benzofuro, benzotieno, tiofeno, nafto indenocondensado, nafto heterociclocondensado y benzo heterociclocondensado. Además, de acuerdo con diversas realizaciones no limitantes, B y B’ pueden seleccionarse cada uno independientemente entre:
9
(xiii) un anillo que contiene nitrógeno representado por la Fórmula i, que se ha expuesto anteriormente;
(xiv) un grupo representado por una de las Fórmulas ii o iii, que se han expuesto anteriormente; y
(xv) los grupos R3 inmediatamente adyacentes juntos forman un grupo representado por una de las Fórmulas vii, viii o ix, que se han expuesto anteriormente.
5 Además, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento, el compuesto fotocrómico representado por la Fórmula XII comprende al menos un agente de alargamiento (L) como se ha definido anteriormente.
10 Como se ha analizado anteriormente con respecto a los compuestos fotocrómicos generalmente representados por la Fórmula II desvelados en el presente documento, los compuestos fotocrómicos generalmente representados por la Fórmula XII pueden extenderse en cualquier posición disponible mediante sustitución con L o un grupo R3 sustituido con L, y/o en cualquier dirección deseada mediante distintas combinaciones de sustituciones de posiciones disponibles con L o grupos R3 sustituidos con L. Por lo tanto, por ejemplo, aunque de manera no limitante
15 en el presente documento, los compuestos fotocrómicos generalmente representados por la Fórmula XII pueden extenderse sustituyendo el grupo SP con L o un grupo R3 sustituido con L y/o sustituyendo el grupo A con L o un grupo R3 sustituido con L para proporcionar una relación de absorción promedio deseada para el compuesto fotocrómico.
20 Como se ha analizado anteriormente en referencia a la Fórmula XII, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento, el grupo SP puede ser indolino. Más específicamente, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento, el compuestos fotocrómico puede representarse por la Fórmula XIII:
25
en donde cada R’’ se selecciona independientemente en cada ocasión entre hidrógeno, un alquilo sustituido o sin sustituir, cicloalquilo, arilalquilo o juntos forman cicloalquilo que está sustituido o sin sustituir; R’’’ se selecciona entre un grupo alquilo, arilo o arilalquilo que está sin sustituir o sustituido con al menos uno de: (i) -CH(CN)2 o 30 CH(COOX1)2; (ii) -CH(X2)(X3); y (iii) -C(O)X24 (en donde X1, X2, X3 y X24 son como se ha definido anteriormente); y
(iv) halógeno, hidroxi, éster o amina; y en donde al menos uno de i y r es al menos 1 y al menos un R3 comprende L.
Por ejemplo, aunque de manera no limitante en el presente documento, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento en donde el grupo SP es indolino, el compuesto fotocrómico puede 35 representarse por al menos una de Fórmula XIV y Fórmula XV:
23
Secuencia de reacción I
5 Las secuencias de reacción más específicas para sintetizar los compuestos fotocrómicos de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento y generalmente representadas por la Fórmula XII anterior y más específicamente representadas por la Fórmula XIII anterior, en donde Y es N y SP es indolino se representan a continuación en las Secuencias de reacción J y K.
10 En la Secuencia de reacción J (a continuación), un nitrosofenol representado por la Fórmula φ1 se hace reaccionar en metanol con un agente de alargamiento L, que es piperazino fenol (representado por la Fórmula φ2), para formar el nitrosonaftol sustituido con L representado por la Fórmula φ3. Como se representa en la Secuencia de reacción J, el nitrosonaftol sustituido con L puede además sustituirse con uno o más grupos R, cada uno de los cuales puede comprender un agente de alargamiento L que es igual o diferente a los restantes sustituyentes L. El nitrosonaftol
15 sustituido con L representado por la Fórmula φ3 después se acopla por calentamiento con la base de Fischer representada por la Fórmula φ4 para producir la naftoxazina sustituida con L representada por la Fórmula φ5.
28
Claims (1)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US48410003P | 2003-07-01 | 2003-07-01 | |
US484100P | 2003-07-01 |
Publications (1)
Publication Number | Publication Date |
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ES2656823T3 true ES2656823T3 (es) | 2018-02-28 |
Family
ID=34062022
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES11001432T Active ES2706656T3 (es) | 2003-07-01 | 2004-05-26 | Compuestos fotocrómicos |
ES11001431.3T Active ES2656823T3 (es) | 2003-07-01 | 2004-05-26 | Compuestos fotocrómicos |
ES11001433T Active ES2704995T3 (es) | 2003-07-01 | 2004-05-26 | Compuestos fotocrómicos |
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Application Number | Title | Priority Date | Filing Date |
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ES11001432T Active ES2706656T3 (es) | 2003-07-01 | 2004-05-26 | Compuestos fotocrómicos |
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Application Number | Title | Priority Date | Filing Date |
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ES11001433T Active ES2704995T3 (es) | 2003-07-01 | 2004-05-26 | Compuestos fotocrómicos |
Country Status (13)
Country | Link |
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US (5) | US7342112B2 (es) |
EP (4) | EP1639058B1 (es) |
JP (12) | JP5197956B2 (es) |
KR (4) | KR100875002B1 (es) |
CN (4) | CN101276015B (es) |
AU (1) | AU2004256030B2 (es) |
BR (4) | BR122015025454B1 (es) |
CA (1) | CA2531088C (es) |
ES (3) | ES2706656T3 (es) |
HK (3) | HK1109645A1 (es) |
MX (1) | MXPA06000168A (es) |
WO (1) | WO2005005570A1 (es) |
ZA (1) | ZA200600143B (es) |
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US7342112B2 (en) * | 2003-07-01 | 2008-03-11 | Ppg Industries Ohio, Inc. | Photochromic compounds |
US7632540B2 (en) | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
US7097303B2 (en) * | 2004-01-14 | 2006-08-29 | Ppg Industries Ohio, Inc. | Polarizing devices and methods of making the same |
AU2005238090A1 (en) * | 2004-04-30 | 2005-11-10 | Advanced Polymerik Pty Ltd | Photochromic compositions and articles comprising siloxane, alkylene or substituted alkylene oligomers |
US8563212B2 (en) | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles, non-aqueous dispersions thereof and articles prepared therewith |
US8563213B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles |
US9028728B2 (en) | 2005-04-08 | 2015-05-12 | Transitions Optical, Inc. | Photochromic materials that include indeno-fused naphthopyrans |
US9139552B2 (en) | 2005-04-08 | 2015-09-22 | Transitions Optical, Inc. | Indeno-fused naphthopyrans having ethylenically unsaturated groups |
US8647538B2 (en) * | 2005-04-08 | 2014-02-11 | Transitions Optical, Inc. | Photochromic compounds having at least two photochromic moieties |
US7556750B2 (en) * | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
US9052438B2 (en) * | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
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