EP1694774A1 - Materiaux composites transparents luminescents - Google Patents

Materiaux composites transparents luminescents

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Publication number
EP1694774A1
EP1694774A1 EP04802635A EP04802635A EP1694774A1 EP 1694774 A1 EP1694774 A1 EP 1694774A1 EP 04802635 A EP04802635 A EP 04802635A EP 04802635 A EP04802635 A EP 04802635A EP 1694774 A1 EP1694774 A1 EP 1694774A1
Authority
EP
European Patent Office
Prior art keywords
luminescent
polymer
plastic
transparent
nanoparticles
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.)
Withdrawn
Application number
EP04802635A
Other languages
German (de)
English (en)
Inventor
Stefan Kaskel
Ullrich Holle
Holger Althues
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.)
Studiengesellschaft Kohle gGmbH
Original Assignee
Studiengesellschaft Kohle gGmbH
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 Studiengesellschaft Kohle gGmbH filed Critical Studiengesellschaft Kohle gGmbH
Publication of EP1694774A1 publication Critical patent/EP1694774A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/59—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing silicon
    • C09K11/592—Chalcogenides
    • C09K11/595—Chalcogenides with zinc or cadmium
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/54—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing zinc or cadmium
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/56—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing sulfur
    • C09K11/562—Chalcogenides
    • C09K11/565—Chalcogenides with zinc cadmium
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/61—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing fluorine, chlorine, bromine, iodine or unspecified halogen elements
    • C09K11/615—Halogenides
    • C09K11/616—Halogenides with alkali or alkaline earth metals
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/64—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing aluminium
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/64—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing aluminium
    • C09K11/641—Chalcogenides
    • C09K11/643—Chalcogenides with alkaline earth metals
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/67—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing refractory metals
    • C09K11/68—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing refractory metals containing chromium, molybdenum or tungsten
    • C09K11/681—Chalcogenides
    • C09K11/684—Chalcogenides with alkaline earth metals
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/70—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing phosphorus
    • C09K11/705—Halogenides
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/77—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing rare earth metals
    • C09K11/7701—Chalogenides
    • C09K11/7703—Chalogenides with alkaline earth metals
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/77—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing rare earth metals
    • C09K11/7704—Halogenides
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/77—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing rare earth metals
    • C09K11/7708—Vanadates; Chromates; Molybdates; Tungstates
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
    • C09K11/881—Chalcogenides
    • C09K11/883—Chalcogenides with zinc or cadmium

Definitions

  • the present invention relates to a luminescent transparent polymer, a method for producing this polymer and the use of the polymer for producing luminescent transparent glasses and for producing glasses coated with the polymer.
  • Doped zinc sulfide nanoparticles can be prepared in solution using different processes by precipitation reactions from zinc salts and a sulfur source such as thiourea or sodium sulfide.
  • a sulfur source such as thiourea or sodium sulfide.
  • zinc acetate and manganese acetate are reacted with Na 2 S in methanol, which results in 3-4 nm ZnS: Mn particles.
  • the ZnS nanoparticles doped with manganese luminesce with excitation with UV light (300 nm) with orange color (590 nm) but only with low quantum yields of up to 4%.
  • z. B. polymethacrylic acid can be used in aqueous solution. It is also known that the intensity of the photoluminescence of doped zinc sulfide nanoparticles can be increased considerably by the adsorption of acrylic acid or polyacrylic acid on the surface of the particles. Particles produced in this way can be used, for example, for the production of composite films.
  • ZnS nanocrystals doped with copper are also suitable for the production of polymer composites with polymethacrylic acid methyl ester (PMMA) in the form of thin films for the production of electroluminescent components.
  • PMMA polymethacrylic acid methyl ester
  • CN1394900 describes a method for producing ZnS nanoparticles, in which a zinc salt is reacted with H 2 S in an organic solvent and then processed with the polymer to form a film. It is not described whether the nano-ZnS / polymer dispersions are transparent or cloudy.
  • JP2002105325 describes a transparent film made of acrylic glass, which contains semiconductor nanoparticles such as ZnS and CdSe. The particles are stabilized by a phosphine oxide. These films typically contain a high proportion of solids and are a maximum of a few micrometers thick, to produce electroluminescent components from it.
  • JP2002047425 describes the production of thermoplastic composites from ZnS nanoparticles and a copolymer containing styrene-methacrylate for the production of high-index glasses. Thiols are used to stabilize the nanoparticles.
  • Stabilizers such as thiols, phosphine oxides or surfactants are generally added to improve stability.
  • Stabilizers such as thiols act as radical scavengers in the case of a radical-initiated polymerization and adversely affect the polymerization.
  • the object of the present invention was to provide luminescent plastic glasses which, in particular in terms of their transparency, differ little or only slightly from the pure plastic glass. These glasses should preferably be able to be produced in a simple manner.
  • the present invention accordingly relates to transparent, luminescent plastic glasses which contain luminescent nanoparticles.
  • transparent means that viewing the glass in visible light means that no clouding due to scattering effects can be observed.
  • the particles produced as powder must be separated from one another by suitable dispersion methods in the monomer in order to eliminate scattering effects from aggregates which are larger than the primary particle size, and this dispersion may also be used in the course of the polymerization of larger amounts of monomer in bulk, which leads to shaping and Manufacture of glazing is used, do not cloud it.
  • Plastic glass means that the plastic can take any shape, e.g. B. has the shape of a film or three-dimensional object.
  • the nanoparticles have a particle size of 1 to 300 nm, preferably up to 100 nm, which here means the individual discrete crystallites. It can also be agglomerates are present, the total size of which is above 3 nm and in particular below 100 nm.
  • the nanoparticles are preferably in the form of discrete crystallites or small agglomerates which do not exceed a particle size of 50 nm. Larger agglomerates are disadvantageous because they can reduce the transparency of the finished glass.
  • the glasses according to the invention are particularly suitable for the production of decorative objects, such as in luminescent glazing, decorative lamp parts or transparent color representations, which use a UV source as the active light source.
  • decorative objects such as in luminescent glazing, decorative lamp parts or transparent color representations, which use a UV source as the active light source.
  • they can be used to illuminate printed posters, timetables, etc.
  • the nanoparticles contained according to the invention can be used to modify the properties of the plastic glasses without reducing their transparency.
  • the refractive index can be increased by introducing the nanoparticles, which is advantageous for the use of the glasses in optical components.
  • Another advantage is that many luminescent nanoparticles have a fire-retardant effect and can therefore contribute to improving fire protection when using large-area glazing made from plastic glazing, in particular glazing made from polymethacrylic acid methyl esters.
  • the luminescent nanoparticles contained according to the invention can be selected from phosphors (luminous pigments) and / or phosphors doped with transition metals and / or lanthanides.
  • phosphors luminous pigments
  • Preferred and well-suited phosphors are e.g. B. ZnS and ZnO.
  • the phosphors are preferably present in the glasses in an amount of 0.1 to 20% by weight, based on the amount of polymer.
  • the nanoparticles can be doped with metals known for doping, such as Al, transition metals such as Cu, Ag, Mn, rare earths such as Eu, Yb etc. These metals are preferably in an amount of 0.1 to 5 wt .-%, based on the phosphor.
  • the plastic glasses used according to the invention are preferably selected from conventional transparent plastics.
  • the plastic glasses are preferably polymers or polymer mixtures which are selected from polyacrylates and their derivatives, for example based on acrylic acid, butanediol monoacrylate, trimethylol propane triacrylate, etc., polymethacrylates, polycarbonates, polystyrenes, epoxides, polyethylene terephthalates, ethylene-norbornene copolymers, and any copolymers of the corresponding monomers.
  • Another object of the present invention is a method for producing a luminescent, transparent plastic glass, which is characterized in that one or more luminescent nanoparticles are mixed with a polymer precursor or a solution of the polymer precursor and the mixture obtained is polymerized in a manner known per se.
  • the luminescent nanoparticles are preferably intimately mixed with the polymer precursor or a solution of this polymer precursor in a first process step, product with uniform luminescence and transparency being able to be obtained when the nanoparticles are dispersed in the polymer precursor.
  • the mixture can be heated during the dispersion, but the temperature should be below the polymerization or decomposition temperature of the polymer precursor.
  • the nanoparticles are produced from their soluble salts by precipitation reactions known to the person skilled in the art immediately before incorporation into the polymer precursor. It is also possible to form these in situ from the precursors in a mixture with the polymer precursor. Particularly stable dispersions are obtained when the nanoparticles are prepared from the soluble salts in an alcoholic solution, for example in the presence of methanol, ethanol, i-propanol, butanol or similar solvents. It is assumed that particles form during the precipitation reaction which can be stabilized particularly well by the polar residues, such as the OH groups and by polar groups in the polymer precursor. The phosphor particles obtained are notable for particularly good colloidal stability in the polymer precursor.
  • the nanoparticles are first mixed with a subset of the polymer precursor.
  • the mixture or dispersion obtained can then be mixed with further polymer precursor, which can be a different one than the first subset, and then polymerized.
  • nanoparticles which, as described above, by Precipitation reaction were obtained from an alcoholic solution, these are preferably at least partially separated from the solvent and mixed or dispersed with a polymer precursor.
  • the mixture obtained is preferably a clear dispersion in which the nanoparticles are colloidally dissolved or distributed.
  • the mixture or dispersion obtained is then mixed with further polymer precursor and, as described below, subjected to the polymerization.
  • the polymerization precursor is preferably selected from the monomers or polymerizable oligopolymers which are liquid at processing temperature or are soluble in a solvent.
  • the nanoparticles can be mixed with the pure monomer or a mixture of several monomers or oligopolymers that can be polymerized with one another. If it facilitates dispersing, polymerization or further processing, a solvent can also be added. The solvent should not negatively influence the polymerization and the stability of the nanoparticles in the polymer precursor or in the finished product and should be easy to remove.
  • Suitable solvents are, for example, water, methanol, ethanol, tetrahydrofuran, CH 2 Cl 2 , low-boiling alkanes such as pentane or hexane, aromatics such as toluene, etc.
  • the nanoparticles are as finely divided as possible in the mixture produced, i.e. finely dispersed, before.
  • the particle size of the dispersed nanoparticles is preferably below 100 nm.
  • the mixture of nanoparticles and polymer precursor obtained is polymerized in a known manner in the second process stage.
  • the nanoparticles are preferably only mixed with a subset of the polymer precursor required for producing the glass according to the invention. The remaining amount is added shortly before the polymerization. If it is advantageous for the polymerization, the mixture obtained and, if appropriate, further polymer precursors can be mixed with water to produce a dispersion. Depending on the type of polymerization, an initiator and / or catalyst etc. can also be added.
  • Luminescent transparent glasses are obtained.
  • the mixture obtained in the second process stage is applied to a finished plastic or silicate glass and polymerized on this glass. In this way, glasses coated with luminescent transparent plastic glass can be obtained.
  • Another object is the use of the luminescent transparent plastic glasses according to the invention for the production of lighting elements, luminescent representations including lettering on objects such as glasses, for marking plastics, etc.
  • Another object is the use of the luminescent transparent plastic glasses according to the invention for the production of coatings on inorganic or organic glasses.
  • a stable ethanolic dispersion of the ZnO nanoparticles can be produced as follows:
  • the particles luminesce under UV radiation.
  • BDMA butanediol monoacrylate
  • Ethanol can be distilled off from this mixture in vacuo, so that about 10 ml of dispersion remain.
  • BDMA butanediol monoacrylate
  • a white precipitate is centrifuged off.
  • the supernatant dispersion continues to show the green luminescence of the ZnO particles and is transparent; the precipitation does not contain any significant amounts of ZnO.
  • the surrounding BDMA is polymerizable and miscible with other monomers (methyl methacrylate, styrene and trimethylolpropane triacrylate (TMPTA)). The copolymerization with these monomers leads to transparent, luminescent composite materials.
  • 3 g of the BDMA / ZnO dispersion are mixed with 1 g of TMPTA and 0.004 g of Lucirin TPO (UV initiator) and placed between two glass plates, which are set to 1.5 by a soft PVC ring mm are kept.
  • the mixture and the gas space above the liquid are flushed with argon and irradiated with UV light for one minute (UVA-Cube, Hoenle).
  • a solid, transparent polymer plate is obtained which has the fluorescent properties of the ZnO.
  • 1.5 g of the BDMA / ZnO dispersion from Example 3 are mixed with 1.5 g of styrene, 1 g of TMPTA and 0.004 g of Lucirin TPO (UV initiator) and polymerized as transparent plates as in 3c).
  • 1.5 g of the BDMA / ZnO dispersion from Example 3 are mixed with 1.5 g of methyl methacrylate, 1 g of TMPTA and 0.004 g of Lucirin TPO (UV initiator) and polymerized as transparent plates as in 3c).

Abstract

L'invention concerne un verre plastique luminescent transparent contenant des nanoparticules luminescentes, ainsi qu'un procédé de production de ce verre plastique. Ledit verre plastique diffère à peine ou légèrement, en termes de transparence, d'un verre plastique pur. En outre, le verre plastique selon l'invention peut être produit facilement.
EP04802635A 2003-10-22 2004-10-20 Materiaux composites transparents luminescents Withdrawn EP1694774A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10349063A DE10349063A1 (de) 2003-10-22 2003-10-22 Lumineszierende transparente Kompositmaterialien
PCT/DE2004/002347 WO2005037925A1 (fr) 2003-10-22 2004-10-20 Materiaux composites transparents luminescents

Publications (1)

Publication Number Publication Date
EP1694774A1 true EP1694774A1 (fr) 2006-08-30

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EP04802635A Withdrawn EP1694774A1 (fr) 2003-10-22 2004-10-20 Materiaux composites transparents luminescents

Country Status (5)

Country Link
US (1) US20090014687A1 (fr)
EP (1) EP1694774A1 (fr)
JP (1) JP2007523221A (fr)
DE (2) DE10349063A1 (fr)
WO (1) WO2005037925A1 (fr)

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Also Published As

Publication number Publication date
US20090014687A1 (en) 2009-01-15
JP2007523221A (ja) 2007-08-16
DE10349063A1 (de) 2005-05-25
WO2005037925A1 (fr) 2005-04-28
DE112004002596D2 (de) 2006-09-14

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