ES2525937T3 - Instalaciones de alineación para colorantes ópticos - Google Patents

Instalaciones de alineación para colorantes ópticos Download PDF

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Publication number
ES2525937T3
ES2525937T3 ES09764659.0T ES09764659T ES2525937T3 ES 2525937 T3 ES2525937 T3 ES 2525937T3 ES 09764659 T ES09764659 T ES 09764659T ES 2525937 T3 ES2525937 T3 ES 2525937T3
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phenylacryloyl
alkyl
alkoxy
liquid crystal
group represented
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Meng He
Anil Kumar
Peter C. Foller
Chenguang Li
Ruisong Xu
Jiping Shao
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Transitions Optical Inc
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Transitions Optical Inc
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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    • C09K19/00—Liquid crystal materials
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    • C09K19/38—Polymers
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/542—Macromolecular compounds
    • C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/12—Optical coatings produced by application to, or surface treatment of, optical elements by surface treatment, e.g. by irradiation
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
    • G02C7/108—Colouring materials
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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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
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/542—Macromolecular compounds
    • C09K2019/546—Macromolecular compounds creating a polymeric network
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C—CHEMISTRY; METALLURGY
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    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/03—Viewing layer characterised by chemical composition
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    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/06—Substrate layer characterised by chemical composition
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
    • Y10T428/264—Up to 3 mils
    • Y10T428/265—1 mil or less

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Nonlinear Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Mathematical Physics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Eyeglasses (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Liquid Crystal Substances (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Polymerisation Methods In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Sistema de polímeros con separación de fases que comprende: - una fase matriz al menos parcialmente curada que comprende: - un residuo polimérico de al menos un primer monómero de cristal líquido; y - una fase huésped que comprende: - al menos un material fotoactivo seleccionado entre compuestos fotocrómicos y compuestos fotocrómico-dicroicos; y - al menos un material de cristal líquido, en el que al menos una parte de la fase huésped se separa de al menos una parte de la fase matriz durante el curado al menos parcial del residuo polimérico del al menos un primer monómero de cristal líquido y en el que al menos uno del primer monómero de cristal líquido de la fase matriz y el al menos un material de cristal líquido de la fase huésped comprende al menos un compuesto que contiene mesógeno que tiene una estructura representada por la Fórmula I:**Fórmula** en la que, a) cada X es independientemente: i) un grupo R, ii) un grupo representado por -(L)y-R, iii) un grupo representado por -(L)-R, iv) un grupo representado por -(L)w-Q; v) un grupo representado por vi) un grupo representado por -(L)y-R; o vii) un grupo representado por -(L)w-[(L)w-P]y; b) cada P es un grupo reactivo seleccionado independientemente entre un grupo Q, hidrógeno, arilo, hidroxialquilo C1-C18, alquilo C1-C18, alcoxi C1-C18, aminoalquileno C1-C18, alquil(C1-C18)amino, dialquil(C1-C18)amino, alquil(C1-C18)alcoxi C1-C18, alcoxi(C1-C18)alcoxi C1-C18, nitro, polialquil C1-C18 éter, alquil(C1-C18)alcoxi(C1-C18)alquileno(C1-C18), polietilenoxi, polipropilenoxi, etileno, acriloílo, acriloiloxialquileno C1-C18, metacriloílo, metacriloiloxialquileno C1-C18, 2- cIoroacriloílo, 2-fenilacriloílo, acriloilfenileno, 2-cloroacriloilamino, 2-fenilacriloilamino, oxetanilo, glicidilo, ciano, isocianato de alquilo C1-C18, éster de ácido itacónico, vinil éter, éster de vinilo, un derivado de estireno, polímeros de cristal líquido de cadena principal y de cadena lateral, derivados de siloxano, derivados de etilenimina, derivados de ácido maleico, derivados de ácido fumárico, derivados de ácido cinámico sin sustituir, derivados de ácido cinámico que están sustituidos con al menos uno de metilo, metoxi, ciano y halógeno, o grupos monovalentes o divalentes quirales o no quirales sustituidos o sin sustituir, elegidos entre radicales esteroides, radicales terpenoides, radicales alcaloides y mezclas de los mismos, en los que los sustituyentes son elegidos independientemente entre alquilo C1-C18, alcoxi C1-C18, amino, cicloalquilo C3-C10, alquil(C1-C18)alcoxi C1-C18, fluoroalquilo C1-C18, ciano, cianoalquilo C1-C18, cianoalcoxi C1-C18 o mezclas de los mismos, o P es una estructura que tiene de 2 a 4 grupos reactivos o P es un precursor de polimerización por metátesis de apertura de anillo sin sustituir o sustituido; c) el grupo Q es hidroxi, amino, alquenilo C2-C18, alquinilo C2-C18, azido, sililo, siloxi, sililhidruro, (tetrahidro-2H-piran-2-il)oxi, tio, isocianato, tioisocianato, acriloiloxi, metacriloiloxi, 2-(acriloiloxi)etilcarbamilo, 2-(metacriloiloxi)etilcarbamilo, aziridinilo, aliloxicarboniloxi, epoxi, ácido carboxílico, éster carboxílico, acriloilamino, metacriloilamino, aminocarbonilo, alquil(C1-C18)aminocarbonilo, aminocarbonilalquileno C1-C18, alquil(C1-C18)oxicarboniloxi, o halocarbonilo.

Description

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E09764659
12-12-2014
aditivo BYK®-346 de BYK Chemie, USA.
(2)
El iniciador era IRGACURE® 819, un fotoiniciador que está disponible en Ciba-Geigy Corporation.
(3)
El estabilizante era 2-metil hidroquinona.
Tabla 2
Nº de Ejemplo
LCM Anfitriones LCM Huéspedes Colorante
4
RM-257(4)/LCM-1 (1:1) ZLI-1565 PC/DD-1
5
RM-257(4)/RM-105(5)/RM-23 (6)/RM-82(7) (1:1:1:1) LCM-2 PC/DD-1
6
RM-257(4)/RM-105(5)/RM-23 (6)/RM-82(7) (1:1:1:1) LCM-3 PC/DD-1
EC-1
RM-257(4)/RM-105(5)/RM-23 (6)/RM-82(7) (1:1:1:1) -- PC/DD-1
(4) RM 257 es un monómero de cristal líquido disponible en EMD Chemicals, Inc. y se informa que tiene la fórmula molecular de C33H32O10. (5) RM 105 es un monómero de cristal líquido disponible en EMD Chemicals, Inc. y se informa que tiene la fórmula molecular de C23H26O6. (6) RM 23 es un monómero de cristal líquido disponible en EMD Chemicals, Inc. y se informa que tiene la fórmula molecular de C29H23NO5. (7) RM 82 es un monómero de cristal líquido disponible en EMD Chemicals, Inc. y se informa que tiene la fórmula molecular de C23H26O6. (8) ZLI-1565 es una formulación de cristal líquido disponible en Merck.
A un vial (20 ml) que contenía una barra de agitación magnética se añadió cada uno de los monómeros de cristal líquido, colorantes, estabilizante, e iniciador. El disolvente se añadió a los contenidos en el vial, y el vial se tapó y se envolvió con lámina de aluminio y a continuación se colocó en un agitador magnético. La mezcla resultante se calentó a 80 °C y se agitó durante aproximadamente 30 min hasta que la solución se volvió transparente. La solución se enfrió a temperatura ambiente y se tomó una pequeña gota de solución mediante un capilar para el estudio de transición de fase. A continuación, la solución resultante se enfrió a temperatura ambiente y se almacenó en la oscuridad.
Ejemplo 8 -Preparación de Muestras revestidas con los Ejemplos 4-6 y EC-1
Cada uno de los Ejemplos y EC se usó en el procedimiento que se describe en lo sucesivo en el presente documento en las Partes A-E, para preparar revestimientos al menos parciales en la superficie de un sustrato. Antes de la preparación, se determinaron las transiciones de fase de cada ejemplo mediante el procedimiento descrito en la Parte
F. Las Relaciones de Absorción y las medidas de la respuesta óptica se describen en la Parte G.
Parte A -Limpieza del Sustrato
Se obtuvieron sustratos cuadrados que medían 5,08 cm por 5,08 cm por 0,318 cm (2 pulgadas por 2 pulgadas por 0,125 pulgadas) preparados a partir del monómero CR-39® de Homalite, Inc., Wilmington, DE. Cada sustrato se limpió pasando un trapo con un tejido empapado con acetona y secando con una corriente de gas nitrógeno.
Parte B -Aplicación de la Capa de Alineación
Una solución de una red de polímero foto-orientable disponible como solución Staralign® 2200 CP10 de Huntsman Advanced Materials, Basilea, Suiza, se diluyó al 4 por ciento en peso en ciclopentanona. La solución resultante se aplicó por revestimiento en centrífuga a una porción de la superficie del sustrato de ensayo administrando aproximadamente 1,0 ml de la solución Staralign® y centrifugando los sustratos a 1000 revoluciones por minuto (rpm) durante 10 segundos. A continuación, los sustratos revestidos se colocaron en un horno mantenido a 135 °C durante 30 minutos.
Para la capa de alineación producida por frotado, se disolvió triacetato de celulosa (TAC) en ciclopentanona al 4 por ciento en peso y se aplicó por revestimiento en centrífuga a una porción de la superficie del sustrato de ensayo administrando aproximadamente 1,0 ml de la solución de TAC y centrifugando los sustratos a 500 rpm durante 3 segundos seguido de 1000 rpm durante 10 segundos. A continuación, los sustratos revestidos se colocaron en un horno mantenido a 140 °C durante 60 minutos.
Parte C -Orientación de las Capas de Alineación
Después de la aplicación, la red de polímero foto-orientable se ordenó al menos parcialmente por exposición a radiación ultravioleta polarizada linealmente durante 5 minutos a una intensidad máxima de 80-100 Vatios/m2 de UVA (320-390 nm) tal como se mide usando Radiómetro de International Light Research, Modelo IL-1700 con un sistema detector que comprende un detector del Modelo SEDO33, Filtro B y difusor. La visualización de salida del radiómetro
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Claims (1)

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ES09764659.0T 2008-12-05 2009-11-25 Instalaciones de alineación para colorantes ópticos Active ES2525937T3 (es)

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US329197 2008-12-05
US12/329,197 US8003005B2 (en) 2003-07-01 2008-12-05 Alignment facilities for optical dyes
PCT/US2009/065850 WO2010065406A1 (en) 2008-12-05 2009-11-25 Alignment facilities for optical dyes

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US (5) US7632540B2 (es)
EP (1) EP2358845B1 (es)
JP (4) JP4891355B2 (es)
KR (5) KR20060026122A (es)
CN (3) CN100478716C (es)
AU (2) AU2009200311B2 (es)
BR (1) BRPI0917048A2 (es)
CA (2) CA2678715C (es)
ES (1) ES2525937T3 (es)
MX (1) MX2011005862A (es)
WO (1) WO2010065406A1 (es)
ZA (2) ZA200600144B (es)

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Publication number Priority date Publication date Assignee Title
US7632540B2 (en) * 2003-07-01 2009-12-15 Transitions Optical, Inc. Alignment facilities for optical dyes
US7256921B2 (en) * 2003-07-01 2007-08-14 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
US8545984B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Photochromic compounds and compositions
US8545015B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Polarizing photochromic articles
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