WO2011071794A1 - Photoalignment materials having improved adhesion - Google Patents

Photoalignment materials having improved adhesion 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
Application number
PCT/US2010/059035
Other languages
English (en)
French (fr)
Inventor
Gobinda Saha
Anil Kumar
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
Family has litigation
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 AU2010328455A priority Critical patent/AU2010328455B2/en
Priority to KR1020127017424A priority patent/KR101415498B1/ko
Priority to MX2012006588A priority patent/MX2012006588A/es
Priority to BR112012013530-9A priority patent/BR112012013530B1/pt
Priority to JP2012543178A priority patent/JP5579275B2/ja
Application filed by Transitions Optical, Inc. filed Critical Transitions Optical, Inc.
Priority to CA2782787A priority patent/CA2782787C/en
Priority to ES10793096T priority patent/ES2431831T3/es
Priority to EP10793096.8A priority patent/EP2510023B9/en
Priority to CN201080060648.8A priority patent/CN102695732B/zh
Publication of WO2011071794A1 publication Critical patent/WO2011071794A1/en
Priority to HK13101912.8A priority patent/HK1174933A1/xx

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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)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Mathematical Physics (AREA)
  • Spectroscopy & Molecular 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)
PCT/US2010/059035 2009-12-08 2010-12-06 Photoalignment materials having improved adhesion WO2011071794A1 (en)

Priority Applications (10)

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
KR1020127017424A KR101415498B1 (ko) 2009-12-08 2010-12-06 접착력이 향상된 광정렬 재료
MX2012006588A MX2012006588A (es) 2009-12-08 2010-12-06 Materiales para fotoalineamiento que tienen propiedades de adhesion mejoradas.
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
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
CA2782787A CA2782787C (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
EP10793096.8A EP2510023B9 (en) 2009-12-08 2010-12-06 Photoalignment materials having improved adhesion
HK13101912.8A HK1174933A1 (en) 2009-12-08 2013-02-15 Photoalignment materials having improved adhesion

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 (en) 2011-06-16

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PCT/US2010/059035 WO2011071794A1 (en) 2009-12-08 2010-12-06 Photoalignment materials having improved adhesion

Country Status (13)

Country Link
US (2) US9475901B2 (ja)
EP (1) EP2510023B9 (ja)
JP (4) JP5579275B2 (ja)
KR (1) KR101415498B1 (ja)
CN (1) CN102695732B (ja)
AU (1) AU2010328455B2 (ja)
BR (1) BR112012013530B1 (ja)
CA (1) CA2782787C (ja)
ES (1) ES2431831T3 (ja)
HK (1) HK1174933A1 (ja)
MX (1) MX2012006588A (ja)
TW (1) TWI468476B (ja)
WO (1) WO2011071794A1 (ja)

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 (ja) * 2013-03-29 2014-10-02 日産化学工業株式会社 ブロック化されたイソシアネート基を有する重合体を含有する液晶配向剤、液晶配向膜、及び液晶表示素子
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 (en) * 2016-10-11 2020-06-24 Mitsui Chemicals, Inc. POLYMERIZABLE COMPOSITION FOR OPTICAL MATERIAL AND USE THEREOF

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* Cited by examiner, † Cited by third party
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US8545015B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Polarizing photochromic articles
US8623238B2 (en) 2008-06-27 2014-01-07 Transitions Optical, Inc. Mesogenic stabilizers
US8613868B2 (en) 2008-06-27 2013-12-24 Transitions Optical, Inc Mesogenic stabilizers
US9557456B2 (en) 2010-01-29 2017-01-31 The United States Of America As Represented By The Secretary Of The Army Broadband optics for manipulating light beams and images
US11366254B2 (en) 2010-01-29 2022-06-21 Beam Engineering For Advanced Measurements Co. High-efficiency wide-angle beam steering system
US10197715B1 (en) 2013-03-15 2019-02-05 Beam Engineering For Advanced Measurements Co. Methods of diffractive lens and mirror fabrication
US9983479B2 (en) 2010-04-21 2018-05-29 Beam Engineering For Advanced Measurements Co. Fabrication of high efficiency, high quality, large area diffractive waveplates and arrays
US10114239B2 (en) 2010-04-21 2018-10-30 Beam Engineering For Advanced Measurements Co. Waveplate lenses and methods for their fabrication
US20110262844A1 (en) 2010-04-21 2011-10-27 Beam Engineering For Advanced Measurement Co. Fabrication of high efficiency, high quality, large area diffractive waveplates and arrays
JP5679050B2 (ja) * 2011-06-30 2015-03-04 Dic株式会社 共重合体、ならびにその硬化物からなる液晶配向層
JP6010910B2 (ja) * 2012-01-23 2016-10-19 住友化学株式会社 組成物及び光学フィルム
JP6010911B2 (ja) * 2012-01-23 2016-10-19 住友化学株式会社 光学フィルム及びその製造方法
JP2015099170A (ja) * 2012-03-05 2015-05-28 シャープ株式会社 液晶表示装置及び液晶表示装置の製造方法
US20140017418A1 (en) * 2012-05-30 2014-01-16 Lg Chem, Ltd. Aqueous composition, optical film including the same, polarizing plate using the same, and liquid crystal display device using the same
US20130331482A1 (en) * 2012-06-06 2013-12-12 Jnc Petrochemical Corporation Polymer composition having photoalignable group, liquid crystal alignment film formed of the polymer composition, and optical device having phase difference plate formed of the liquid crystal alignment film
US8649081B1 (en) * 2012-09-14 2014-02-11 Transitions Optical, Inc. Photochromic article having two at least partially crossed photochromic-dichroic layers
US10107945B2 (en) 2013-03-01 2018-10-23 Beam Engineering For Advanced Measurements Co. Vector vortex waveplates
US10185182B2 (en) * 2013-03-03 2019-01-22 Beam Engineering For Advanced Measurements Co. Mechanical rubbing method for fabricating cycloidal diffractive waveplates
JP6250324B2 (ja) * 2013-08-02 2017-12-20 大阪有機化学工業株式会社 光配向膜用組成物および新規重合体
CN104345501B (zh) * 2013-08-05 2018-01-19 北京京东方光电科技有限公司 制备窄边框显示装置的方法
KR101976222B1 (ko) * 2014-07-18 2019-05-07 전북대학교산학협력단 액정배향 재료, 이를 이용한 액정표시소자 및 액정표시소자의 제조방법
WO2015036072A1 (en) * 2013-09-13 2015-03-19 Merck Patent Gmbh Polymerisable liquid crystal material and polymerised liquid crystal film
US9418273B2 (en) 2013-09-18 2016-08-16 Blackberry Limited Structure for multicolor biometric scanning user interface
US9311545B2 (en) 2013-09-18 2016-04-12 Blackberry Limited Multicolor biometric scanning user interface
CA2946693A1 (en) 2014-04-16 2015-10-22 David E. Roberts Methods and apparatus for human vision correction using diffractive waveplate lenses
JP6337594B2 (ja) * 2014-04-21 2018-06-06 Jsr株式会社 液晶配向剤、液晶配向膜の製造方法及び液晶表示素子
JP6269952B2 (ja) * 2014-07-02 2018-01-31 Jnc株式会社 光配向膜用組成物
CN106536575B (zh) * 2014-07-18 2020-09-29 富士胶片株式会社 聚合物、组合物、光学薄膜及液晶显示装置
KR102474637B1 (ko) 2014-09-30 2022-12-05 트랜지션즈 옵티칼 인코포레이티드 자외선 광 흡수제
JP6554777B2 (ja) * 2014-10-09 2019-08-07 Dic株式会社 光配向膜用の共重合体
JP6712846B2 (ja) * 2015-03-25 2020-06-24 日東電工株式会社 偏光フィルム用硬化型接着剤組成物、偏光フィルムおよびその製造方法、光学フィルムならびに画像表示装置
US11130912B2 (en) 2015-06-12 2021-09-28 Transitions Optical, Inc. Alignment polymers
US10875833B2 (en) 2015-06-12 2020-12-29 Transitions Optical, Inc. Alignment compounds
US10191296B1 (en) 2015-06-30 2019-01-29 Beam Engineering For Advanced Measurements Co. Laser pointer with reduced risk of eye injury
US9976911B1 (en) 2015-06-30 2018-05-22 Beam Engineering For Advanced Measurements Co. Full characterization wavefront sensor
WO2017065080A1 (ja) * 2015-10-16 2017-04-20 Dic株式会社 光配向膜用ポリマー、ポリマー溶液、光配向膜、光学異方体、及び液晶表示素子
JPWO2017065079A1 (ja) * 2015-10-16 2018-02-08 Dic株式会社 光配向膜用ポリマー、ポリマー溶液、光配向膜、光学異方体、及び液晶表示素子
US10436957B2 (en) 2015-10-27 2019-10-08 Beam Engineering For Advanced Measurements Co. Broadband imaging with diffractive waveplate coated mirrors and diffractive waveplate objective lens
MX2018005102A (es) 2015-10-30 2018-06-06 Transitions Optical Inc Metodo de fabricacion de articulos opticos que tienen propiedades que modifican el gradiente de luz.
CN108603960B (zh) 2015-10-30 2021-11-09 光学转变有限公司 用喷墨印刷设备制造光学制品的方法
KR102480724B1 (ko) 2015-10-30 2022-12-22 트랜지션즈 옵티칼 인코포레이티드 구배 광 반응성을 갖는 광학 제품 및 이의 제조 방법
CN116224481A (zh) * 2015-10-30 2023-06-06 光学转变公司 光学制品及其制备方法
KR20180094104A (ko) 2015-12-28 2018-08-22 닛산 가가쿠 가부시키가이샤 액정 배향제, 액정 배향막, 및 액정 표시 소자
US11028323B2 (en) 2015-12-28 2021-06-08 Nissan Chemical Industries, Ltd. Liquid crystal aligning agent containing crosslinking agent and polymer that has site having isocyanate group and/or blocked isocyanate group and site having photoreactivity, liquid crystal alignment film, and liquid crystal display element
CN109563384A (zh) * 2016-06-13 2019-04-02 阿卡特肖勒公司 离子聚合物及其作为湿粘合剂和涂料的用途
KR101970724B1 (ko) 2016-06-14 2019-04-22 삼성에스디아이 주식회사 감광성 수지 조성물, 감광성 수지막 및 이를 이용한 컬러필터
CN105954935B (zh) * 2016-06-24 2019-11-26 明基材料有限公司 液晶装置
US11035983B2 (en) * 2016-09-26 2021-06-15 Verily Life Sciences Llc Cast-moldable, high refractive index, rigid, gas permeable polymer formulations for an accommodating contact lens
US10423045B2 (en) 2016-11-14 2019-09-24 Beam Engineering For Advanced Measurements Co. Electro-optical diffractive waveplate beam shaping system
EP3558651B1 (en) 2016-12-23 2024-03-13 Transitions Optical, Ltd. Method of manufacture of a lens with gradient properties using imbibition technology
WO2018122719A1 (en) * 2016-12-27 2018-07-05 Sabic Global Technologies B.V. Methods for grafting liquid crystalline coatings onto polymer surfaces
WO2018121852A1 (en) 2016-12-28 2018-07-05 Transitions Optical, Ltd. Method for imparting an optical element with a light influencing property in a gradient pattern
WO2018121873A1 (en) 2016-12-30 2018-07-05 Transitions Optical, Ltd. Polarizing article and method of forming a polarizing article
US11453654B2 (en) 2017-05-10 2022-09-27 Transitions Optical, Ltd. Photochromic indeno fused phenanthrenopyran compounds
US10274805B2 (en) 2017-06-13 2019-04-30 Beam Engineering For Advanced Measurements Co. Polarization-independent switchable lens system
US10619099B2 (en) 2017-08-25 2020-04-14 Ppg Industries Ohio, Inc. Dielectric devices and methods of fabrication
US10866455B2 (en) 2017-10-19 2020-12-15 Ppg Industries Ohio, Inc. Display devices including photochromic-dichroic compounds and dichroic compounds
KR20200088846A (ko) * 2017-11-30 2020-07-23 닛산 가가쿠 가부시키가이샤 액정 배향제, 액정 배향막 및 액정 표시 소자
WO2019159707A1 (ja) * 2018-02-15 2019-08-22 富士フイルム株式会社 バインダー組成物、バインダー層、光学積層体および画像表示装置
US11982906B1 (en) 2018-03-05 2024-05-14 Beam Engineering For Advanced Measurements Co. Polarization-independent diffractive optical structures
US11175441B1 (en) 2018-03-05 2021-11-16 Beam Engineering For Advanced Measurements Co. Polarization-independent diffractive optical structures
KR102183676B1 (ko) 2018-04-17 2020-11-27 주식회사 엘지화학 타원 편광판 및 유기발광장치
GB2586124B (en) * 2019-07-31 2023-02-01 Flexenable Ltd Multiple layer optical cells
JP2022543238A (ja) * 2019-08-02 2022-10-11 ブルーワー サイエンス アイ エヌ シー． 持続的接合及びパターニングの材料
US11294240B2 (en) 2019-08-10 2022-04-05 Beam Engineering For Advanced Measurements Co. Diffractive waveplate devices that operate over a wide temperature range
CN111196714B (zh) * 2020-03-10 2021-08-31 福州大学 一种基于光定向沉积技术制备连续梯度材料的方法
CN111842003A (zh) * 2020-03-25 2020-10-30 杭州星华反光材料股份有限公司 一种大图型花式反光图案上胶装置和上胶方法
CA3183684A1 (en) 2020-06-01 2021-12-08 Icares Medicus, Inc. Double-sided aspheric diffractive multifocal lens, manufacture, and uses thereof
EP4244305A1 (en) 2020-11-10 2023-09-20 Transitions Optical, Ltd. Photochromic-dichroic articles
EP4244304A1 (en) 2020-11-10 2023-09-20 Transitions Optical, Ltd. Method for preparing a coated article
US20220298420A1 (en) * 2021-03-19 2022-09-22 Facebook Technologies, Llc Multifunctional liquid crystalline photoreactive polymers for polarization holography
US11827727B2 (en) * 2021-11-29 2023-11-28 Fujifilm Corporation Photo-alignment polymer, binder composition, binder layer, optical laminate, optical laminate manufacturing method, and image display device

Citations (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1097303A (en) 1913-05-28 1914-05-19 Thomas J Costello Annealing-furnace.
US4556605A (en) 1982-09-09 1985-12-03 Kabushiki Kaisha Suwa Seikosha Photochromic coating composition and photochromic synthetic resin ophthalmic lens
US4756973A (en) 1985-07-09 1988-07-12 Kureha Kagaku Kogyo Kabushiki Kaisha Photochromic lens
US5231194A (en) 1989-12-21 1993-07-27 Sumitomo Chemical Co., Ltd. Process for producing coumarin derivatives
US5247099A (en) 1989-08-17 1993-09-21 Abbott Laboratories Process for synthesis of 7-hydroxy coumarins having substitutions in the 4-position
US5300656A (en) 1989-11-21 1994-04-05 Bayer Aktiengesellschaft Coumarin derivatives, process for their preparation, their use and thiazolyl acetic acid derivatives as intermediates
US5342970A (en) 1991-05-30 1994-08-30 Laboratoires Eurobio Hydrosoluble coumarin derivatives, their preparation and their use as an enzyme substrate or for the preparation of such substrates
US5580819A (en) 1995-03-22 1996-12-03 Ppg Industries, Inc. Coating composition, process for producing antireflective coatings, and coated articles
US5637739A (en) 1990-03-21 1997-06-10 Research Corporation Technologies, Inc. Chiral catalysts and catalytic epoxidation catalyzed thereby
US5658501A (en) 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US5962617A (en) 1995-02-02 1999-10-05 Simula Inc. Impact resistant polyurethane and method of manufacture thereof
US6025026A (en) 1997-06-30 2000-02-15 Transitions Optical, Inc. Process for producing an adherent polymeric layer on polymeric substrates and articles produced thereby
WO2000015629A1 (en) * 1998-09-11 2000-03-23 Ppg Industries Ohio, Inc. Polymerizable polyalkoxylated naphthopyrans
US6042737A (en) 1997-06-05 2000-03-28 Ppg Industries Ohio, Inc. Process for improving adhesion of coatings to polymeric substrates and articles produced thereby
US6060001A (en) 1998-12-14 2000-05-09 Ppg Industries Ohio, Inc. Alkoxyacrylamide photochromic coatings compositions and photochromic articles
US6107427A (en) 1995-09-15 2000-08-22 Rolic Ag Cross-linkable, photoactive polymer materials
EP1038870A1 (en) * 1999-03-24 2000-09-27 Corning S.A. 3,3-bis(aryl)-5-((N-(un)substituted)amido)naphthopyrans, their preparation, compositions and (co)polymer matrices containing them
US6150430A (en) 1999-07-06 2000-11-21 Transitions Optical, Inc. Process for adhering a photochromic coating to a polymeric substrate
WO2001002449A2 (en) 1999-07-02 2001-01-11 Ppg Industries Ohio, Inc. Poly(meth)acrylic photochromic coating
US6187444B1 (en) 1997-02-21 2001-02-13 Ppg Industries Ohio, Inc. Photochromic polyurethane coating and articles having such a coating
US6217948B1 (en) 1997-09-17 2001-04-17 Merck Patent Gesellschaft Mit Polymer film
WO2001032661A1 (en) * 1999-11-04 2001-05-10 Corning S.A. Naphthopyrans with a heterocycle in the 5,6-position, preparation, and compositions and matrices containing them
WO2001036406A1 (en) * 1999-11-17 2001-05-25 Corning S.A. Naphthopyrans annelated in c5-c6 with an indene- or dihydronaphthalene-type and compositions and matrices containing them
US6268055B1 (en) 1997-12-08 2001-07-31 Ppg Industries Ohio, Inc. Photochromic epoxy resin coating composition and articles having such a coating
US6433043B1 (en) 2000-11-28 2002-08-13 Transitions Optical, Inc. Removable imbibition composition of photochromic compound and kinetic enhancing additive
US6432544B1 (en) 1998-12-18 2002-08-13 Ppg Industries Ohio, Inc. Aminoplast resin photochromic coating composition and photochromic articles
US6436525B1 (en) 1998-12-11 2002-08-20 Ppg Industries Ohio, Inc. Polyanhydride photochromic coating composition and photochromic articles
US6506488B1 (en) 1998-12-18 2003-01-14 Ppg Industries Ohio, Inc. Aminoplast resin photochromic coating composition and photochromic articles
US6531076B2 (en) 2000-02-04 2003-03-11 Ppg Industries Ohio, Inc. Photochromic organic resin composition
US6532076B1 (en) 2000-04-04 2003-03-11 Therma-Wave, Inc. Method and apparatus for multidomain data analysis
US20030165686A1 (en) 2001-12-27 2003-09-04 Blackburn William P. Photochromic optical article
US6641874B2 (en) 2000-03-02 2003-11-04 Merck Patent Gesellschaft Mit Beschraenkter Haftung Multilayer reflective film or pigment with viewing angle dependent reflection characteristics
WO2004060861A2 (en) 2002-12-06 2004-07-22 Rolic Ag Crosslinkable, photoactive polymers and their use
US20040207809A1 (en) 2001-12-27 2004-10-21 Blackburn William P Photochromic optical article
US20050004361A1 (en) 2003-07-01 2005-01-06 Anil Kumar Photochromic compounds
US20050012998A1 (en) 2003-07-01 2005-01-20 Anil Kumar Polarizing, photochromic devices and methods of making the same
WO2005015298A1 (en) 2003-08-08 2005-02-17 Merck Patent Gmbh Alignment layer with reactive mesogens for aligning liquid crystal molecules
US20050151926A1 (en) 2004-01-14 2005-07-14 Anil Kumar Polarizing devices and methods of making the same
US20050196617A1 (en) 2004-03-04 2005-09-08 King Eric M. Photochromic optical article
US20050196618A1 (en) 2004-03-04 2005-09-08 Knox Carol L. Photochromic optical article
US20050196616A1 (en) 2004-03-04 2005-09-08 Stewart Kevin J. Photochromic optical article
US20050196696A1 (en) 2004-03-04 2005-09-08 King Eric M. Photochromic optical article
US20050196626A1 (en) 2004-03-04 2005-09-08 Knox Carol L. Photochromic optical article
US7058249B2 (en) 2001-10-16 2006-06-06 Lightwave Microsystems Corporation Waveplate and optical circuit formed using mesogen-containing polymer
US20060226400A1 (en) * 2005-04-08 2006-10-12 Wenjing Xiao Photochromic materials with reactive substituents
US7169448B2 (en) 1999-09-16 2007-01-30 Merck Patent Gmbh Optical compensator and liquid crystal display l
US7173114B2 (en) 2003-02-08 2007-02-06 Samsung Electronics Co., Ltd. Lightfast colorant and lightfast ink composition including the same
USRE39605E1 (en) 1996-07-26 2007-05-01 Merck Patent Gmbh Combination of optical elements
US7238831B2 (en) 2001-01-23 2007-07-03 Southwest Research Institute Mesogens
US20090146104A1 (en) 2003-07-01 2009-06-11 Transitions Optical, Inc. Alignment facilities for optical dyes
US20090323011A1 (en) 2008-06-27 2009-12-31 Transitions Optical, Inc. Mesogen containing compounds

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0798413A (ja) 1993-09-29 1995-04-11 Fuji Photo Film Co Ltd 光学補償シート及びその製造方法およびそれを用いた液晶表示素子
JP3592735B2 (ja) 1993-11-05 2004-11-24 富士写真フイルム株式会社 光学補償シート及びその製造方法およびそれを用いた液晶表示素子
KR100955968B1 (ko) * 1999-07-02 2010-05-13 메르크 파텐트 게엠베하 모노반응성 메소제닉 화합물
EP1219651A1 (en) * 2000-12-29 2002-07-03 Rolic AG Photoactive copolymer
US7074344B2 (en) * 2001-10-03 2006-07-11 Jsr Corporation Liquid crystal aligning agent and liquid crystal display element
JP4524458B2 (ja) * 2002-05-31 2010-08-18 エルシコン・インコーポレーテッド 光学配向層調製用分岐ハイブリッドポリマー材料
US7978391B2 (en) * 2004-05-17 2011-07-12 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
WO2005005573A1 (en) * 2003-07-12 2005-01-20 Merck Patent Gmbh Polymerised liquid crystal film with improved adhesion
ITRM20050055U1 (it) * 2005-05-02 2006-11-03 Enea Ente Nuove Tec Sistema di accumulo energetico integrato.
US7892449B2 (en) * 2005-05-19 2011-02-22 Dai Nippon Printing Co., Ltd. Liquid crystal display and manufacturing method of same
US7666510B2 (en) * 2005-09-07 2010-02-23 Transitions Optical, Inc. Optical elements that include curable film-forming compositions containing blocked isocyanate adhesion promoters
JP2007086399A (ja) 2005-09-22 2007-04-05 Dainippon Printing Co Ltd 光学素子
WO2007052979A1 (en) 2005-11-07 2007-05-10 Lg Chem. Ltd. Copolymer for liquid crystal alignment, liquid crystal aligning layer including copolymer for liquid crystal alignment, and liquid crystal display including liquid crystal aligning layer
EP2103635B1 (en) 2007-01-17 2012-09-12 Asahi Glass Company, Limited Oil-repellent copolymer, method for producing the same and oil-repellent processing liquid
JP5597141B2 (ja) * 2008-01-11 2014-10-01 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 反応性メソゲン化合物および混合物
JP5321790B2 (ja) 2008-05-23 2013-10-23 Ｊｓｒ株式会社 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
US20100014010A1 (en) * 2008-06-27 2010-01-21 Transitions Optical, Inc. Formulations comprising mesogen containing compounds
US20090326186A1 (en) * 2008-06-27 2009-12-31 Transitions Optical, Inc. Mesogen containing compounds
EP2447769B1 (en) 2009-06-23 2015-03-25 Nissan Chemical Industries, Ltd. Composition for forming thermoset film having photo alignment properties
US9475901B2 (en) * 2009-12-08 2016-10-25 Transitions Optical, Inc. Photoalignment materials having improved adhesion

Patent Citations (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1097303A (en) 1913-05-28 1914-05-19 Thomas J Costello Annealing-furnace.
US4556605A (en) 1982-09-09 1985-12-03 Kabushiki Kaisha Suwa Seikosha Photochromic coating composition and photochromic synthetic resin ophthalmic lens
US4756973A (en) 1985-07-09 1988-07-12 Kureha Kagaku Kogyo Kabushiki Kaisha Photochromic lens
US5247099A (en) 1989-08-17 1993-09-21 Abbott Laboratories Process for synthesis of 7-hydroxy coumarins having substitutions in the 4-position
US5300656A (en) 1989-11-21 1994-04-05 Bayer Aktiengesellschaft Coumarin derivatives, process for their preparation, their use and thiazolyl acetic acid derivatives as intermediates
US5231194A (en) 1989-12-21 1993-07-27 Sumitomo Chemical Co., Ltd. Process for producing coumarin derivatives
US5637739A (en) 1990-03-21 1997-06-10 Research Corporation Technologies, Inc. Chiral catalysts and catalytic epoxidation catalyzed thereby
US5342970A (en) 1991-05-30 1994-08-30 Laboratoires Eurobio Hydrosoluble coumarin derivatives, their preparation and their use as an enzyme substrate or for the preparation of such substrates
US5962617A (en) 1995-02-02 1999-10-05 Simula Inc. Impact resistant polyurethane and method of manufacture thereof
US5580819A (en) 1995-03-22 1996-12-03 Ppg Industries, Inc. Coating composition, process for producing antireflective coatings, and coated articles
US5658501A (en) 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US6107427A (en) 1995-09-15 2000-08-22 Rolic Ag Cross-linkable, photoactive polymer materials
USRE39605E1 (en) 1996-07-26 2007-05-01 Merck Patent Gmbh Combination of optical elements
US6187444B1 (en) 1997-02-21 2001-02-13 Ppg Industries Ohio, Inc. Photochromic polyurethane coating and articles having such a coating
US6042737A (en) 1997-06-05 2000-03-28 Ppg Industries Ohio, Inc. Process for improving adhesion of coatings to polymeric substrates and articles produced thereby
US6025026A (en) 1997-06-30 2000-02-15 Transitions Optical, Inc. Process for producing an adherent polymeric layer on polymeric substrates and articles produced thereby
US6217948B1 (en) 1997-09-17 2001-04-17 Merck Patent Gesellschaft Mit Polymer film
US6268055B1 (en) 1997-12-08 2001-07-31 Ppg Industries Ohio, Inc. Photochromic epoxy resin coating composition and articles having such a coating
WO2000015629A1 (en) * 1998-09-11 2000-03-23 Ppg Industries Ohio, Inc. Polymerizable polyalkoxylated naphthopyrans
US6436525B1 (en) 1998-12-11 2002-08-20 Ppg Industries Ohio, Inc. Polyanhydride photochromic coating composition and photochromic articles
US6060001A (en) 1998-12-14 2000-05-09 Ppg Industries Ohio, Inc. Alkoxyacrylamide photochromic coatings compositions and photochromic articles
US6432544B1 (en) 1998-12-18 2002-08-13 Ppg Industries Ohio, Inc. Aminoplast resin photochromic coating composition and photochromic articles
US6506488B1 (en) 1998-12-18 2003-01-14 Ppg Industries Ohio, Inc. Aminoplast resin photochromic coating composition and photochromic articles
EP1038870A1 (en) * 1999-03-24 2000-09-27 Corning S.A. 3,3-bis(aryl)-5-((N-(un)substituted)amido)naphthopyrans, their preparation, compositions and (co)polymer matrices containing them
US6602603B2 (en) 1999-07-02 2003-08-05 Ppg Industries Ohio, Inc. Poly(meth)acrylic photochromic coating
WO2001002449A2 (en) 1999-07-02 2001-01-11 Ppg Industries Ohio, Inc. Poly(meth)acrylic photochromic coating
US6150430A (en) 1999-07-06 2000-11-21 Transitions Optical, Inc. Process for adhering a photochromic coating to a polymeric substrate
US7169448B2 (en) 1999-09-16 2007-01-30 Merck Patent Gmbh Optical compensator and liquid crystal display l
WO2001032661A1 (en) * 1999-11-04 2001-05-10 Corning S.A. Naphthopyrans with a heterocycle in the 5,6-position, preparation, and compositions and matrices containing them
WO2001036406A1 (en) * 1999-11-17 2001-05-25 Corning S.A. Naphthopyrans annelated in c5-c6 with an indene- or dihydronaphthalene-type and compositions and matrices containing them
US6531076B2 (en) 2000-02-04 2003-03-11 Ppg Industries Ohio, Inc. Photochromic organic resin composition
US6641874B2 (en) 2000-03-02 2003-11-04 Merck Patent Gesellschaft Mit Beschraenkter Haftung Multilayer reflective film or pigment with viewing angle dependent reflection characteristics
US6532076B1 (en) 2000-04-04 2003-03-11 Therma-Wave, Inc. Method and apparatus for multidomain data analysis
US6433043B1 (en) 2000-11-28 2002-08-13 Transitions Optical, Inc. Removable imbibition composition of photochromic compound and kinetic enhancing additive
US7238831B2 (en) 2001-01-23 2007-07-03 Southwest Research Institute Mesogens
US7058249B2 (en) 2001-10-16 2006-06-06 Lightwave Microsystems Corporation Waveplate and optical circuit formed using mesogen-containing polymer
US20040207809A1 (en) 2001-12-27 2004-10-21 Blackburn William P Photochromic optical article
US7410691B2 (en) 2001-12-27 2008-08-12 Ppg Industries Ohio, Inc. Photochromic optical article
US20030165686A1 (en) 2001-12-27 2003-09-04 Blackburn William P. Photochromic optical article
WO2004060861A2 (en) 2002-12-06 2004-07-22 Rolic Ag Crosslinkable, photoactive polymers and their use
US7173114B2 (en) 2003-02-08 2007-02-06 Samsung Electronics Co., Ltd. Lightfast colorant and lightfast ink composition including the same
US20050012998A1 (en) 2003-07-01 2005-01-20 Anil Kumar Polarizing, photochromic devices and methods of making the same
US20090146104A1 (en) 2003-07-01 2009-06-11 Transitions Optical, Inc. Alignment facilities for optical dyes
US7342112B2 (en) 2003-07-01 2008-03-11 Ppg Industries Ohio, Inc. Photochromic compounds
US20050004361A1 (en) 2003-07-01 2005-01-06 Anil Kumar Photochromic compounds
WO2005015298A1 (en) 2003-08-08 2005-02-17 Merck Patent Gmbh Alignment layer with reactive mesogens for aligning liquid crystal molecules
US20050151926A1 (en) 2004-01-14 2005-07-14 Anil Kumar Polarizing devices and methods of making the same
US7044599B2 (en) 2004-01-14 2006-05-16 Ppg Industries Ohio, Inc. Polarizing devices and methods of making the same
US20050196626A1 (en) 2004-03-04 2005-09-08 Knox Carol L. Photochromic optical article
US20050196696A1 (en) 2004-03-04 2005-09-08 King Eric M. Photochromic optical article
US20050196616A1 (en) 2004-03-04 2005-09-08 Stewart Kevin J. Photochromic optical article
US20050196618A1 (en) 2004-03-04 2005-09-08 Knox Carol L. Photochromic optical article
US20050196617A1 (en) 2004-03-04 2005-09-08 King Eric M. Photochromic optical article
US20060226400A1 (en) * 2005-04-08 2006-10-12 Wenjing Xiao Photochromic materials with reactive substituents
US20090323011A1 (en) 2008-06-27 2009-12-31 Transitions Optical, Inc. Mesogen containing compounds

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
"Flussige Kristalle in Tabellen II", 1984, VEB DEUTSCHER VERLAG FUR GRUNDSTOFFINDUSTRIE
"Flüssige Kristalle in Tabellen II", 1984, VEB DEUTSCHER VERLAG FÜR GRUNDSTOFFINDUSTRIE
"Kirk-Othmer Encyclopedia of Chemical Technology", vol. 7, 2004, article "Coating Processes", pages: 1 - 35
DEMUS ET AL.: "Flüssige Kristalle in Tabellen", 1974, VEB DEUTSCHER VERLAG FÜR GRUNDSTOFFINDUSTRIE
DEMUS ET AL.: "Flussige Kristalle in Tabellen", 1974, VEB DEUTSCHER VERLAG FUR GRUNDSTOFTINDUSTRIE
K. TAKATOH: "The Liquid Crystal Book Series: Alignment Technologies and Application of Liquid Crystal Devices", 2005, TAYLOR AND FRANCIS, pages: 63
KOHKI TAKOTAH ET AL.: "Alignment Technologies and Applications of Liquid Crystal Devices", 2005, TAYLOR AND FRANCIS, pages: 61 - 63
MACROMOL. CHEM. PHYS., vol. 210, 2009, pages 1484 - 1492
MACROMOLECULES, vol. 27, 1994, pages 832 - 837
MACROMOLECULES, vol. 36, 2003, pages 6527 - 6536
MOLECULAR CRYSTAL AND LIQUID CRYSTAL, vol. 479, 2007, pages 121
X. TASSEL ET AL.: "A New Blocking Agcnt of Isocyanates", EUROPEAN POLYMER JOURNAL, vol. 36, 2000, pages 1745 - 1751
Z. W. WICKS JR., PROGRESS IN ORGANIC COATINGS, vol. 3, 1975, pages 73 - 99

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US9688501B2 (en) 2014-07-01 2017-06-27 Wincor Nixdorf International Gmbh Apparatus for separating sheet material
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