WO2011095441A1 - Photopolymer-formulierung mit triazin-basierten schreibmonomeren - Google Patents

Photopolymer-formulierung mit triazin-basierten schreibmonomeren Download PDF

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Publication number
WO2011095441A1
WO2011095441A1 PCT/EP2011/051246 EP2011051246W WO2011095441A1 WO 2011095441 A1 WO2011095441 A1 WO 2011095441A1 EP 2011051246 W EP2011051246 W EP 2011051246W WO 2011095441 A1 WO2011095441 A1 WO 2011095441A1
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WIPO (PCT)
Prior art keywords
acrylate
meth
photopolymer formulation
holograms
formulation according
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/EP2011/051246
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German (de)
English (en)
French (fr)
Inventor
Thomas RÖLLE
Friedrich-Karl Bruder
Thomas Fäcke
Marc-Stephan Weiser
Dennis Hönel
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.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
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
Application filed by Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Priority to JP2012551583A priority Critical patent/JP6023592B2/ja
Priority to US13/576,775 priority patent/US9366957B2/en
Priority to KR1020127020255A priority patent/KR20120125270A/ko
Priority to CN2011800081361A priority patent/CN102763037A/zh
Priority to RU2012137134/04A priority patent/RU2012137134A/ru
Priority to BR112012019378A priority patent/BR112012019378A2/pt
Priority to EP11701279.9A priority patent/EP2531892B1/de
Publication of WO2011095441A1 publication Critical patent/WO2011095441A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
    • C08G18/3804—Polyhydroxy compounds
    • C08G18/3812—Polyhydroxy compounds having fluorine atoms
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/485—Polyethers containing oxyethylene units and other oxyalkylene units containing mixed oxyethylene-oxypropylene or oxyethylene-higher oxyalkylene end groups
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • G03C1/733—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds with macromolecular compounds as photosensitive substances, e.g. photochromic
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/001—Phase modulating patterns, e.g. refractive index patterns
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/035—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyurethanes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
    • G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/2403—Layers; Shape, structure or physical properties thereof
    • G11B7/24035—Recording layers
    • G11B7/24044—Recording layers for storing optical interference patterns, e.g. holograms; for storing data in three dimensions, e.g. volume storage
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/245—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing a polymeric component
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
    • G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
    • G03H2001/026—Recording materials or recording processes
    • G03H2001/0264—Organic recording material
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H2260/00—Recording materials or recording processes
    • G03H2260/12—Photopolymer

Definitions

  • the invention relates to a photopolymer formulation comprising polyurethane matrix polymers, writing monomers and photoinitiators. Further objects of the invention are the use of the photopolymer formulation for the production of holographic media.
  • JP 2004 300046 A, EP 1 229 389 A1 and EP 0 859 283 A1 each disclose photopolymerizable formulations which contain matrix polymers, photoinitiators and triazine derivatives.
  • the refractive index modulation ⁇ produced by the holographic exposure in the photopolymer plays the decisive role.
  • the interference field of signal and reference light beam in the simplest case that of two plane waves
  • the interference field of signal and reference light beam is converted by local photopolymerization of e.g. high refractive acrylates are imaged into a refractive index grating at high intensity locations in the interference field.
  • the width of the spectral range which may contribute to the reconstruction of the hologram, also depends only on the layer thickness d. In this case, the smaller the d the greater the acceptance widths. If you want to produce therefore bright and easily visible holograms, a high on and a small thickness d is desirable and in such a way that DE is as large as possible. That is, the higher the on, the more freedom to design the layer thickness d for bright holograms is achieved without loss of DE. Therefore, optimizing An in the optimization of photopolymer formulations is of paramount importance (P. Hariharan, Optical Holography, 2nd Edition, Cambridge University Press, 1996).
  • di-, tri- or polyisocyanates examples include butylene diisocyanate, hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), l, 8-diisocyanato-4- (isocyanatomethyl) octane, 2,2,4- and / or 2,4,4-trimethylhexamethylene diisocyanate (TMDI), the isomeric bis (4,4'-isocyanatocyclohexyl) methanes and mixtures thereof of any isomer content, isocyanatomethyl-1, 8-octanediisocyanate, 1,4-cyclohexylenediisocyanate, the isomeric cyclohexanedimethylene diisocyanates, 1,4-phenylenediisocyanate, 2,4- and / or 2,6-tolylene diisocyanate, 1,5-naphthylene diisocyanate, 2,4'- or
  • all polyfunctional, isocyanate-reactive compounds can be used per se, which have on average at least 1.5 isocyanate-reactive groups per molecule.
  • suitable alcohols are ethanediol, di-, tri-, tetraethylene glycol, 1,2-propanediol, di-, tri-, tetra-propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 2-butanediol , 3, pentanediol-1,5, 1,6-hexanediol, 2,2-dimethyl-1,3-propanediol, 1,4-dihydroxycyclohexane, 1,4-dimethylolcyclohexane, octanediol-1,8, decanediol-1 , 10, dodecanediol-l, 12, trimethylolpropane, glycerol or any mixtures thereof.
  • Suitable organic carbonates are dimethyl, diethyl and diphenyl carbonate.
  • Suitable diols or mixtures include the polyhydric alcohols of an OH functionality> 2, preferably 1,4-butanediol, 1,6-hexanediol and / or 3-methylpentanediol, which are per se within the scope of the polyester segments, or also polyester polyols can be polycarbonate polyols be reworked.
  • Suitable cyclic ethers are, for example, styrene oxides, ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide, epichlorohydrin, and also any desired mixtures thereof.
  • the starter used may be the polyhydric alcohols of an OH functionality> 2 mentioned in the context of the polyesterpolyols and also primary or secondary amines and aminoalcohols.
  • propylene oxide homopolymers and random or block copolymers which have oxyethylene, oxypropylene and / or oxybutenyl units, the proportion of oxypropylene units based on the total amount of all oxyethylene, oxypropylene and oxybutylene units being at least 20% by weight, preferably at least 45% by weight. -% makes up.
  • Oxypropylene and oxybutylene here include all respective linear and branched C3 and C4 isomers.
  • (type II) initiators such as benzoin and its derivatives, benzil ketals, acylphosphine oxides, for example 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bisacylophosphine oxides, phenylglyoxylic acid esters, camphorquinone, alpha-aminoalkylphenone, alpha-, alpha-dialkoxyacetophenone, [4- (phenylthio) phenyl] octane-1,2-dione-2- (0-benzoyloxime) and alpha-hydroxyalkylphenone.
  • (type II) initiators such as benzoin and its derivatives, benzil ketals, acylphosphine oxides, for example 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bisacylophosphine oxides, phenylglyoxylic acid esters, camphorquinone, alpha-aminoalkylphenone, al
  • Photoinitiator can be used.
  • Suitable ammonium ammonium borate are, for example, tetrabutylammonium triphenylhexylborate, tetrabutylammonium triphenylbutylborate, tetrabutylammonium trinapthylhexylborate, tetrabutylammonium tris (4-tert-butyl) -phenyl-butylborate, tetrabutylammonium tris- (3-fluorophenyl) -hexylborate, tetramethylammonium triphenylbenzylborate, tetra (n-hexyl) ammonium ( sec-butyl) triphenylborate, 1-methyl-3-octylimidazolium dipentyldiphenylborate and tetrabutylammonium tris (3-chloro-4-methylphenyl) hexy
  • anionic polymerization is the use of dyes, such as crystal violet leuconitrile or malachite green leuconitrile, which can polymerize cyanoacrylates by photolytic decomposition (Neckers et al., Macromolecules 2000, 33, 7761) Polymer incorporated so that the resulting polymers are colored through.
  • dyes such as crystal violet leuconitrile or malachite green leuconitrile
  • onium salts especially sulfonium and iodonium salts.
  • the photochemistry of these compounds has been studied sustainably.
  • the iodonium salts first disintegrate homo lyric after excitation and thus generate a radical and a radical anion which stabilizes by H abstraction and releases a proton and then starts the cationic polymerization (Dektar et al., J. Org. Chem. 55, 639, J. Org. Chem., 1991, 56, 1838). This mechanism also allows the use of iodonium salts for radical photopolymerization.
  • urethane acrylates obtainable from the reaction of tris (p-isocyanatophenyl) thiophosphate and m-methylthiophenyl isocyanate with alcohol-functional acrylates such as 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate.
  • Another object of the invention is the use of a photopolymer formulation according to the invention for the production of holographic media, which by appropriate
  • Exposure processes for optical applications in the entire visible and near UV range can be processed into holograms.
  • Visual holograms include all holograms that can be recorded by methods known to those skilled in the art. These include in-line (Gabor) holograms, off-axis holograms, full aperture transfer holograms, white light transmission holograms
  • the detector for the diffracted light can only detect a finite angular range
  • the Bragg curve is not completely detected by wide fetching patterns (small cT) in a ⁇ scan, but only the central area, with suitable detector positioning. Therefore, the complementary to the Bragg curve shape of the transmitted intensity to adjust the layer thickness cT is additionally used.
  • Example 4 Mixture of l, 3,5-triazine-2,4,6-triyltris (oxypropane-2, l-diyl) trisacrylate and l, 3,5-triazine-2,4,6-triyltris (oxypropane-l , 2-diyl) trisacrylate
  • the aqueous phase was separated and 200 mL of 5% NaOH and 200 mL of methylene chloride were added to the organic phase, the aqueous phase was separated again and the organic phase was washed twice with 80 mL of 5% NaOH and three times with each 180 mL of water and dried over sodium sulfate.
  • 0.05 g of hydroquinone (dissolved in methylene chloride) were added, filtered and the solvent was distilled off at a maximum of 45 ° C. bottom temperature under reduced pressure. The product was obtained as a colorless oil.
  • the aqueous phase was separated and 200 mL of 5% NaOH and 200 mL of methylene chloride were added to the organic phase, the aqueous phase was separated again and the organic phase was washed twice with 80 mL of 5% NaOH and three times with each 180 mL of water and dried over sodium sulfate.
  • 0.05 g of hydroquinone (dissolved in methylene chloride) were added. gave, filtered and the solvent was distilled off at a maximum of 45 ° C bottom temperature under reduced pressure. The product was obtained as a colorless oil.
  • the aqueous phase was separated and to the organic phase 50 ml of 5% NaOH and 50 ml of chloroform were added, the aqueous phase was separated again and the organic phase was washed twice with 20 ml of 5% NaOH and three times with each 50 mL of water and dried over sodium sulfate. There were added 0.005 g of hydroquinone (dissolved in acetone), filtered and the solvent was distilled off at a maximum of 45 ° C bottom temperature under reduced pressure. The product was obtained as a colorless oil.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Holo Graphy (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/EP2011/051246 2010-02-02 2011-01-28 Photopolymer-formulierung mit triazin-basierten schreibmonomeren Ceased WO2011095441A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2012551583A JP6023592B2 (ja) 2010-02-02 2011-01-28 トリアジン系書込モノマー含有感光性ポリマー組成物
US13/576,775 US9366957B2 (en) 2010-02-02 2011-01-28 Photopolymer formulation having triazine-based writing monomers
KR1020127020255A KR20120125270A (ko) 2010-02-02 2011-01-28 트리아진-기재 기록 단량체를 갖는 광중합체 배합물
CN2011800081361A CN102763037A (zh) 2010-02-02 2011-01-28 具有三嗪基书写单体的光聚合物配制品
RU2012137134/04A RU2012137134A (ru) 2010-02-02 2011-01-28 Фотополимерная композиция с записывающими мономерами на основе триазина
BR112012019378A BR112012019378A2 (pt) 2010-02-02 2011-01-28 formulação de fotopolímero apresentando monômeros graváveis à base de triazina
EP11701279.9A EP2531892B1 (de) 2010-02-02 2011-01-28 Verwendung einer photopolymer-formulierung mit triazin-basierten schreibmonomeren

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10001006 2010-02-02
EP10001006.5 2010-02-02

Publications (1)

Publication Number Publication Date
WO2011095441A1 true WO2011095441A1 (de) 2011-08-11

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US (1) US9366957B2 (enExample)
EP (1) EP2531892B1 (enExample)
JP (1) JP6023592B2 (enExample)
KR (1) KR20120125270A (enExample)
CN (1) CN102763037A (enExample)
BR (1) BR112012019378A2 (enExample)
RU (1) RU2012137134A (enExample)
WO (1) WO2011095441A1 (enExample)

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TWI489204B (zh) * 2009-11-03 2015-06-21 Bayer Materialscience Ag 製造全像媒體之方法
ATE548730T1 (de) * 2009-11-03 2012-03-15 Bayer Materialscience Ag Photopolymerformulierungen mit einstellbarem mechanischem modul guv
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