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WO2011071794A1 - Matériaux de photoalignement ayant une adhérence améliorée - Google Patents

Matériaux de photoalignement ayant une adhérence améliorée Download PDF

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Publication number
WO2011071794A1
WO2011071794A1 PCT/US2010/059035 US2010059035W WO2011071794A1 WO 2011071794 A1 WO2011071794 A1 WO 2011071794A1 US 2010059035 W US2010059035 W US 2010059035W WO 2011071794 A1 WO2011071794 A1 WO 2011071794A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
substituted
liquid crystal
coating
layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2010/059035
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English (en)
Inventor
Gobinda Saha
Anil Kumar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Transitions Optical Inc
Original Assignee
Transitions Optical Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=44082306&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2011071794(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to KR1020127017424A priority Critical patent/KR101415498B1/ko
Priority to ES10793096T priority patent/ES2431831T3/es
Priority to PH1/2012/501060A priority patent/PH12012501060A1/en
Priority to BR112012013530-9A priority patent/BR112012013530B1/pt
Priority to EP10793096.8A priority patent/EP2510023B9/fr
Priority to HK13101912.8A priority patent/HK1174933B/xx
Priority to MX2012006588A priority patent/MX2012006588A/es
Priority to JP2012543178A priority patent/JP5579275B2/ja
Priority to CA2782787A priority patent/CA2782787C/fr
Priority to AU2010328455A priority patent/AU2010328455B2/en
Application filed by Transitions Optical Inc filed Critical Transitions Optical Inc
Priority to CN201080060648.8A priority patent/CN102695732B/zh
Publication of WO2011071794A1 publication Critical patent/WO2011071794A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/12—Esters of phenols or saturated alcohols
    • C08F222/20—Esters containing oxygen in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • 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
    • C09K19/56—Aligning agents
    • 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
    • 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
    • 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
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • 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
    • 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
    • G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
    • G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/305—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C08F220/365—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate containing further carboxylic moieties
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/02—Alignment layer characterised by 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/02—Alignment layer characterised by chemical composition
    • C09K2323/023—Organic silicon compound, e.g. organosilicon
    • 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31931—Polyene monomer-containing

Definitions

  • photoalignment layers that are capable of aligning adherent liquid crystal layers of up to 1 ,000 microns in thickness are desired.
  • photoalignment materials that may be used to form layers having improved adhesion properties and thicker aligned liquid crystal layers, relative to known photoalignment materials, are desired.
  • the photoalignment materials of the present invention overcome the shortcomings of the previously known photo-aligning copolymers and alignment layers comprising them, and provide the desired improved adhesion properties.
  • each Z a is independently a photochemical ly active chromophore selected from a dimerizable substituted or unsubstituted cinnamate or substituted or unsubstituted coumarin, a cis/trans isomerizable substituted or unsubstituted azo, a photochemically decomposable substituted or unsubstituted polyimide, or a substituted or unsubstituted aromatic ester capable of undergoing a Photo-Fries rearrangement;
  • the (copolymers according to the various embodiments herein may have a polymeric form of a random copolymer, a block copolymer, a graft copolymer, a linear copolymer, a branched copolymer, a hyperbranched copolymer, a dendritic copolymer, or a star copolymer.
  • the (co)polymers may include a polymer chain where different sections may have different forms, such as, for example, a random polymeric section and a block polymeric section.
  • optical elements having the first at least partial layer may further comprise one or more additional at least partial layers on at least a portion of the surface of the substrate.
  • the phrase "on at least a portion of the surface of the substrate” includes layers applied directly onto the surface of the substrate and coating layers applied to one or more layers on the surface of the substrate. That is, the one or more additional layers may be applied directly onto the substrate surface or onto one or more intermediate layers that were previously applied to the surface of the substrate, thereby forming a laminar multilayer coating.
  • liquid crystal materials suitable for use with the photoaiignment materials include the mesogen containing compounds or residues thereof, liquid crystal polymers, liquid crystal pre-polymers, liquid crystal monomers, liquid crystal mesogens, dichroic materials, and photochromic-dichroic materials.
  • pre-polymer means partially polymerized materials.
  • organic materials suitable for use in forming the substrates according to various embodiments disclosed herein include both synthetic and natural organic materials, including: opaque or translucent polymeric materials, natural and synthetic textiles, and cellulosic materials such as, paper and wood,
  • the methods may further comprise at least partially aligning at least a second portion of the photoalignment (copolymer material by exposing the at least partial layer of the photoalignment (co)polymer material at the second portion to polarized UV radiation, wherein the alignment direction of tlie first portion of the pliotoaiignment (co)polymer material is different than the alignment direction of the second portion of the pliotoaiignment (co)polymer material.
  • the adhesion promoter groups on the (co)polymer material may also form attractive bonds with the second at least partial layer.
  • LCD liquid crystal monomers
  • LCM-5 is commercially available RM82 reported to be 2-methyl-l,4-phenylene bis(4-(6- (acryloyloxy)hexyloxy)benzoate), available from EMD Chemicals, inc., having the molecular formula of C39H44O10.
  • PC -2 is reported to be 3-(4-Fluorophenyl-3-(4-piperazinophenyl)-13-ethyl-13-methoxy-6- methoxy-7-(4-(4-(4-(trans)pentylcyclohexyl)benzoy]oxy)-phenyl) benzoyloxy- indeno[2',3':3,4]naphtho[ 1 ,2-b]pyran and was prepared following the procedures of U.S . Pat. No. 7,342, 1 12, which disclosure is incorporated herein by reference.
  • Step 1 To a suitable flask containing a mixture of anisole (3.5 g) and BYK®-346 additive (0.035 g, reported to be a polyether modified poly-dimetliyl-siloxane available from BYK Chemie, USA), was added LCM-2 (3.25 g), LCM-3 (3.25 g), DD- 1 (0.39 g), 4-methoxy phenol (0.0098 g), and IRGACURE ⁇ 819 (0.0975 g t a photoinitiator available from Ciba-Geigy Corporation). The resulting mixture was stirred for 2 hours at 80°C and cooled to about 26°C.
  • BYK®-346 additive 0.035 g, reported to be a polyether modified poly-dimetliyl-siloxane available from BYK Chemie, USA
  • Step 2 Hydroxyethyl methacrylate (0.65 g) and dibutyltin dilaurate (0,008 g) were added and the resulting mixture was stirred for 30 minutes at about 26°C.
  • Finished single vision lenses (6 base, 70 mm) made of polycarbonate from GENTEX OPTICS and semi-finished single vision lenses (4 base, 70 mm) without a hardcoat made of TRIVEX monomer were also used as indicated. These lenses were cleaned by wiping with a tissue soaked with isopropanol and dried with a stream of air.
  • the primer solution was applied to the test substrates by spin-coating on a portion of the surface of the test substrate by dispensing approximately 1.5 mL of the solution and spinning the substrates at 500 revolutions per minute (rpm) for 3 seconds, followed by 1,500 rpm for 7 seconds, followed by 2,500 rpm for 4 seconds.
  • a spin processor from La rell Technologies Corp. (WS- 400B-6NPP/LITE) was used for spin coating.
  • the coated substrates were placed in an oven maintained at 125° C for 60 minutes. The coated substrates were cooled to about 26° C.
  • the substrate was corona treated by passing on a conveyor belt in Tantec EST Systems Serial No.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Mathematical Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Crystal (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

La présente invention porte sur de nouveaux matériaux (co)polymères de photoalignement qui font preuve d'adhérence améliorée à un substrat. La structure (co)polymère comprend au moins un chromophore actif de façon photochimique et au moins un groupe promoteur d'adhérence. L'invention porte également sur des articles de manufacture, sur des éléments optiques, sur des éléments ophtalmiques et sur des cellules à cristaux liquides qui comprennent au moins une couche de photoalignement avec les matériaux (co)polymères de photoalignement, et sur des procédés pour leur fabrication.
PCT/US2010/059035 2009-12-08 2010-12-06 Matériaux de photoalignement ayant une adhérence améliorée Ceased WO2011071794A1 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CN201080060648.8A CN102695732B (zh) 2009-12-08 2010-12-06 具有改进粘合性的光定向材料
MX2012006588A MX2012006588A (es) 2009-12-08 2010-12-06 Materiales para fotoalineamiento que tienen propiedades de adhesion mejoradas.
PH1/2012/501060A PH12012501060A1 (en) 2009-12-08 2010-12-06 Photoalignment materials having improved adhesion
BR112012013530-9A BR112012013530B1 (pt) 2009-12-08 2010-12-06 (co) polímero, artigo de manufatura, método para aplicar um material de foto-alinhamento num elemento óptico e composição de (co) polímero
EP10793096.8A EP2510023B9 (fr) 2009-12-08 2010-12-06 Matériaux de photoalignement ayant une adhérence améliorée
HK13101912.8A HK1174933B (en) 2009-12-08 2010-12-06 Photoalignment materials having improved adhesion
CA2782787A CA2782787C (fr) 2009-12-08 2010-12-06 Materiaux de photoalignement ayant une adherence amelioree
KR1020127017424A KR101415498B1 (ko) 2009-12-08 2010-12-06 접착력이 향상된 광정렬 재료
JP2012543178A JP5579275B2 (ja) 2009-12-08 2010-12-06 向上した接着性を有する光配向材料
AU2010328455A AU2010328455B2 (en) 2009-12-08 2010-12-06 Photoalignment materials having improved adhesion
ES10793096T ES2431831T3 (es) 2009-12-08 2010-12-06 Materiales de fotoalineamiento que tienen una adhesión mejorada

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US26760409P 2009-12-08 2009-12-08
US61/267,604 2009-12-08
US12/959,467 US9475901B2 (en) 2009-12-08 2010-12-03 Photoalignment materials having improved adhesion
US12/959,467 2010-12-03

Publications (1)

Publication Number Publication Date
WO2011071794A1 true WO2011071794A1 (fr) 2011-06-16

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PCT/US2010/059035 Ceased WO2011071794A1 (fr) 2009-12-08 2010-12-06 Matériaux de photoalignement ayant une adhérence améliorée

Country Status (13)

Country Link
US (2) US9475901B2 (fr)
EP (1) EP2510023B9 (fr)
JP (4) JP5579275B2 (fr)
KR (1) KR101415498B1 (fr)
CN (1) CN102695732B (fr)
AU (1) AU2010328455B2 (fr)
BR (1) BR112012013530B1 (fr)
CA (1) CA2782787C (fr)
ES (1) ES2431831T3 (fr)
MX (1) MX2012006588A (fr)
PH (1) PH12012501060A1 (fr)
TW (1) TWI468476B (fr)
WO (1) WO2011071794A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013007802A (ja) * 2011-06-23 2013-01-10 National Printing Bureau 真偽判別媒体
WO2014157625A1 (fr) * 2013-03-29 2014-10-02 日産化学工業株式会社 Agent d'orientation de cristaux liquides contenant un polymère ayant un groupe isocyanate bloqué, film d'orientation de cristaux liquides et élément d'affichage à cristaux liquides
CN104379666A (zh) * 2012-06-20 2015-02-25 日产化学工业株式会社 固化膜形成用组合物、取向材以及相位差材
JP2015135526A (ja) * 2009-12-08 2015-07-27 トランジションズ オプティカル， インコーポレイテッド 向上した接着性を有する光配向材料
US9688501B2 (en) 2014-07-01 2017-06-27 Wincor Nixdorf International Gmbh Apparatus for separating sheet material
EP3527597A4 (fr) * 2016-10-11 2020-06-24 Mitsui Chemicals, Inc. Composition polymérisable pour matériau optique et son utilisation

Families Citing this family (74)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8545015B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Polarizing photochromic articles
US8613868B2 (en) 2008-06-27 2013-12-24 Transitions Optical, Inc Mesogenic stabilizers
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