EP3622353A1 - Feuille plastique dotée d'une couche de colle durcissable aux uv et destinée à la protection d'un hologramme en composite de feuilles-photopolymère - Google Patents

Feuille plastique dotée d'une couche de colle durcissable aux uv et destinée à la protection d'un hologramme en composite de feuilles-photopolymère

Info

Publication number
EP3622353A1
EP3622353A1 EP18721071.1A EP18721071A EP3622353A1 EP 3622353 A1 EP3622353 A1 EP 3622353A1 EP 18721071 A EP18721071 A EP 18721071A EP 3622353 A1 EP3622353 A1 EP 3622353A1
Authority
EP
European Patent Office
Prior art keywords
layer
photopolymer
composite
curable
hologram
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Withdrawn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
EP18721071.1A
Other languages
German (de)
English (en)
Inventor
Serguei Kostromine
Thomas RÖLLE
Thomas Fäcke
Enrico Orselli
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 Intellectual Property GmbH and Co KG
Original Assignee
Covestro Deutschland 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 Covestro Deutschland AG filed Critical Covestro Deutschland AG
Publication of EP3622353A1 publication Critical patent/EP3622353A1/fr
Withdrawn legal-status Critical Current

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Classifications

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    • G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
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    • B32B2310/0806—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation
    • B32B2310/0837—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation using actinic light
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2333/00—Polymers of unsaturated acids or derivatives thereof
    • B32B2333/04—Polymers of esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2333/00—Polymers of unsaturated acids or derivatives thereof
    • B32B2333/04—Polymers of esters
    • B32B2333/12—Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2429/00—Carriers for sound or information
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/204—Plasma displays
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/206—Organic displays, e.g. OLED
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2551/00—Optical elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2559/00—Photographic equipment or accessories
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2475/00—Presence of polyurethane
    • 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
    • G03H1/024—Hologram nature or properties
    • G03H1/0248—Volume holograms
    • 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
    • G03H1/0272—Substrate bearing the hologram
    • 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
    • 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
    • G03H1/04—Processes or apparatus for producing holograms
    • G03H1/18—Particular processing of hologram record carriers, e.g. for obtaining blazed holograms
    • G03H2001/186—Swelling or shrinking the holographic record or compensation thereof, e.g. for controlling the reconstructed wavelength
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H2250/00—Laminate comprising a hologram layer
    • G03H2250/10—Laminate comprising a hologram layer arranged to be transferred onto a carrier body
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H2250/00—Laminate comprising a hologram layer
    • G03H2250/35—Adhesive layer
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H2250/00—Laminate comprising a hologram layer
    • G03H2250/39—Protective layer
    • 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
    • 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
    • G03H2260/30—Details of photosensitive recording material not otherwise provided for
    • G03H2260/33—Having dispersed compound

Definitions

  • the invention relates to a sealed holographic medium comprising a layer structure containing a Photopolymers chi cht and a sealing layer, a method for producing the sealed holographic medium, a kit-of-part, a layer structure for sealing, and their use.
  • Photopolymer layers for the production of holographic media are basically e.g. from WO 201 1/054797 and WO 201 1/067057 known. Advantages of these holographic media are their high diffractive light diffraction efficiency and simplified processing since after holographic exposure no further chemical and / or thermal development steps are necessary.
  • the holographic film (Bayfol® HX from Covestro Deutschland AG) consists of a film substrate (A) and a photosensitive photopolymer layer (B). Optical holograms are formed in the layer (B) by local photopolymerization and fixed by surface UV-VIS exposure. Thus, layer (B) is formed into a non-photosensitive, through-polymerized layer ( ⁇ ') with a previously inscribed hologram. Although this hologram is inherently very stable in the long run, it may be affected by mechanical influences and / or by contact with e.g. organic substances (solvents) change its properties.
  • Possible protection methods are painting, laminating, sticking on a protective layer and / or a protective film.
  • sticking problems associated with liquid adhesive components that completely destroy the hologram upon contact with the (B ') layer or make it unusable due to high optical displacement. It is also problematic to provide an adhesive component capable of adhering to both of the materials, the hologram-containing layer B 'and the protective film.
  • a suitable protective film should be laminatable on the hologram-containing layer ( ⁇ ') and the adhesive layer on the protective film should be neutral to the hologram, ie, not cause deterioration of the intensity of the hologram and no spectral shift of its reflection maximum, as well as adherent to both adjacent layers , ie the hologram-containing layer and the protective film. Furthermore, after the seal, a good solvent resistance in combination with flexibility and elasticity should be ensured.
  • a medium for receiving holograms comprising a substrate layer, a photopolymer layer and one or two protective layers.
  • the protective layer is thereby bonded to the substrate layer, whereby the photopolymer layer between the substrate layer and the protective layer is embedded, without being glued even with the two layers.
  • these protected holographic media are used in I D cards.
  • I D cards For most applications of holographic media where a high standard of uniformity and quality applies to the entire surface of the holographic medium, such a layer structure is difficult or impossible to realize.
  • protective layers can be applied to an exposed photopolymer layer.
  • These protective layers can be prepared by reacting at least one radiation-curing resin I), an isocyanate-functional resin II) and a photoinitiator system III).
  • the protective layers described in EP 2613318 Bl fulfill the requirements for a suitable protective layer since, after application, they make it possible to provide a layer structure with a protective layer and an exposed photopolymer layer which can be fixedly connected to a wide variety of adjacent layers such as adhesive layers, without any volume changes the photopolymer layer and an associated color changes of the hologram comes.
  • the compositions disclosed in E 2 613 318 are not satisfactory in every respect. Due to the presence of an isocyanate-functional resin, they are relatively moisture-labile and chemically reactive to isocyanate-reactive components such as Ol I and NH 2 groups. However, such groups are often present in radiation curing resins or other excipients which are essential for engineering formulation.
  • the protective layer is applied to the photopolymer layer "wet", ie as a solution or dispersion, but it is expensive in industrial practice to build up corresponding liquid application systems and provide personnel who control the coating process. Lamming methods are therefore preferred, but have the disadvantage of The object of the present invention was therefore to provide a layer composite of the type mentioned in the introduction, wherein the seal is easy to apply and is adherent to the hologram-containing layer, the optical properties the exposed photopolymer layer influences as little as possible and ensures a durable resistance to external influences.
  • the sealed holographic medium according to the invention comprising a layer structure B ' -C ' -D.
  • B ' is a photopolymer layer containing a hologram, preferably a volume hologram, obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives,
  • C is an at least partially hardened by actinic radiation surface layer, available from a curable layer C comprising
  • D is a substrate layer which is at least partially bonded to layer C and is present in a planar manner, characterized in that all multifunctional acrylates of the curable layer C are identical to at least one semi-monomer of the unexposed photopolymer layer B.
  • the photopolymer layer B ' is a photopolymer layer in which a hologram, preferably a volume hologram, has been imprinted and this hologram has then been fixed by extensive broadband UV / VIS exposure, preferably fixing with a light energy dose of 5-10 J / cm 2 .
  • the advantage of the holographic medium according to the invention is that the photopolymer layer with the imprinted hologram is encapsulated by this seal, the component C being matched to the layers B 'and D so as to ensure good adhesion to B' and D on the one hand while maintaining frequency stability / grid stability of the log and protection against chemical, physical and mechanical stress.
  • a crosslinkable acrylate component as the adhesive in the layer C of the seal, which is also used as a later monomer in the photopolymer layer B, there is no negative interaction between the crosslinking component of the adhesive layer and the writing monomers, which is expressed by a high optical quality of the imprinted holograms.
  • the verification layer enables compatibility with further layers as well as general improved handling of the histogram, such B. a protection against dustiness by blocking of residual tackiness or by antistatic equipment of the sealing layer accessible.
  • the sealing layer according to the invention the photopolymer layer B 'containing the hologram is protected against physical and chemical influences, such as scratching and solvent damage, at the same time - zl - good adhesion of the layers of the structure with each other and flexibility and elasticity of the sealed holographic medium.
  • the "dry" application of the sealant layer to the unexposed photopolymer layer avoids the provision of expensive machinery and specially trained personnel, such as those required for "wet" application.
  • flat area is understood to mean a flat surface or else a concave or convex curved surface or wavy surface.
  • the photopolymer B 'containing the hologram must have a flat, curved or corrugated surface so that it is flat a lamination of the sealing layer is possible at least in the region of the hologram.
  • “functional” in the context of acrylates means the number of respectively radiation-curing, reactive groups, preferably in the form of double bonds, especially UV-VIS radiation.
  • the term “multi-functional acrylate” is understood to mean a molecule which has at least more than one radiation-curing group, in particular acrylate groups, and, for example, a molecule having three radiation-curing groups, in particular acrylate groups, under a "trifunctional acrylate.”
  • the radiation-curing groups are The term “a” in connection with countable quantities is to be understood as a number word in the context of the present invention only if expressly stated (eg by the expression "1"). exactly one "). If in the following example For example, the word “a” is to be understood as an indefinite article and not as a number word, so it is thus also a Principals form comprises, in which two or more polyisocyanates are present are, for example, structurally differ.
  • the photopolymer layer B ' is at least partially connected on one side to a substrate layer A present in a planar manner, wherein the layers are arranged directly one after the other in the order A-B'-C'-D.
  • Substrate layer A is preferably a transparent thermoplastic substrate layer or other support.
  • the layer structure CD also referred to as layer composite CD
  • the layer structure C'-D also called layer composite C-D, also referred to as a hardened sealing layer as part of a layer structure.
  • the back side of the photopolymer layer B ' is at least partially connected to a second at least partially cured by actinic radiation layer C, wherein the second layer C on the other side is at least partially connected to a two-dimensional substrate layer D, wherein the Layers in the order D-C'-B'-C-D are arranged directly on top of each other.
  • the second layer C and the second substrate layer D may be identical or different from the first layer C and the first substrate layer D.
  • the curable layer C further contains at least one thermoplastic mainly linear partially crystalline polyurethane resin.
  • the multifunctional acrylate of the curable layer C is an at least tri-functional acrylate.
  • the acrylate is selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, 2 -
  • the acrylate is phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate.
  • the layer C contains a UV absorber, preferably in an amount of 0.01 to 10 wt .-%, more preferably in an amount of 0.1 to 5 wt .-%, each based on the total weight of the layer C.
  • the substrate layer D is a thermoplastic transparent
  • the substrate layer D is a thermoplastic transparent amorphous plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent low-birefringence plastic layer. In a further preferred embodiment, the substrate layer D is an amorphous thermoplastic transparent low-birefringence plastic layer.
  • the substrate layer D consists of polycarbonate, copolycarbonate, polyethylene terephthalate, cellulose triacetate, polyamide, mixtures or material composites thereof. In another preferred embodiment, the substrate layer D consists of polycarbonate, copolycarbonate, cellulose triacetate, polyethylene terephthalate, mixtures or material composites thereof.
  • the substrate layer D has a layer thickness of 5 ⁇ to 500 ⁇ , preferably 20 ⁇ to 150 ⁇ on.
  • the sealed holographic medium according to the invention comprises a layer structure B'-C'-D, wherein B 'is a photopolymer layer containing a hologram, preferably a volume hologram, obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives,
  • C is an at least partially hardened by actinic radiation surface layer, available from a curable layer C comprising
  • thermoplastic mainly linear partially crystalline polyurethane resin optionally at least one thermoplastic mainly linear partially crystalline polyurethane resin
  • D is a substrate layer which is at least partially bonded to layer C and is characterized in that all multifunctional acrylates of curable layer C are identical to at least one semi-monomer of unexposed photopolymer layer B, where D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate is preferably polycarbonate preferably made of polycarbonate having an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ , or wherein D is a thermoplastic transparent plastic layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ m, more preferably ⁇ 100 ⁇ m and> 20 ⁇ m, preferably ⁇ 45 ⁇ m and> 20 ⁇ m, more preferably a plastic layer of polyethylene terephthalate (PET) which has been reduced by surface modification in its adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the sealed holographic medium according to the invention comprises a layer structure B'-C'-D, wherein
  • B ' is a photopolymer layer containing a hologram, preferably a volume hologram, obtainable from an unexposed photopolymer B comprising I) matrix polymers,
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives,
  • C is an at least partially hardened by actinic radiation surface layer, available from a curable layer C comprising
  • At least one multifunctional acrylate selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, 2- [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxy] ethyl prop-2-enoate,
  • thermoplastic mainly linear partially crystalline polyurethane resin optionally at least one thermoplastic mainly linear partially crystalline polyurethane resin
  • D is a substrate layer which is at least partially bonded to layer C and is characterized in that all multifunctional acrylates of curable layer C are identical to at least one semi-monomer of unexposed photopolymer layer B, where D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate is preferably polycarbonate preferably made of polycarbonate having an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ , or wherein D is a thermoplastic transparent plastic material layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , preferably ⁇ 45 ⁇ and> 20 ⁇ , more preferably a plastic layer of polyethylene terephthalate (PET) was reduced by surface modification in their adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the invention likewise relates to a layer structure comprising a curable layer C and a substrate layer D which is at least partially bonded to the layer C, characterized in that the curable layer C I) at least one multifunctional acrylate,
  • III optionally comprises auxiliaries and additives.
  • the abovementioned layer structure C-D according to the invention corresponds to the sealing layer according to the invention.
  • the curable layer C further contains at least one thermoplastic mainly linear partially crystalline polyurethane resin.
  • the multifunctional acrylate of the curable layer C is an at least tri-functional acrylate.
  • the acrylate is selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane
  • the acrylate is phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate.
  • the layer C contains a UV absorber, preferably in an amount of 0.01 to 10 wt .-%, more preferably in an amount of 0.1 to 5 wt .-%, each based on the total weight of the layer C.
  • the substrate layer D is a thermoplastic transparent plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent amorphous plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent low-birefringence plastic layer. In a further preferred embodiment, the substrate layer D is an amorphous thermoplastic transparent low-birefringence plastic layer.
  • the substrate layer D consists of polycarbonate, copolycarbonate, polyethylene terephthalate, cellulose triacetate, polyamide, mixtures or material composites thereof. In another preferred embodiment, the substrate layer D consists of polycarbonate, copolycarbonate, cellulose triacetate, polyethylene terephthalate, mixtures or composite materials thereof.
  • the substrate layer D has a layer thickness of 5 ⁇ to 500 ⁇ , preferably 20 ⁇ to 150 ⁇ on.
  • the layer structure according to the invention comprises a curable layer C and a substrate layer D, which is at least partially joined to the layer C, characterized in that the curable layer C I) at least one multifunctional acrylate,
  • III optionally comprises auxiliaries and additives.
  • D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate, preferably polycarbonate more preferably polycarbonate having an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ m preferably ⁇ 100 ⁇ m and> 20 ⁇ m, more preferably ⁇ 65 ⁇ m and> 20 ⁇ m, or wherein D is a thermoplastic transparent plastic layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ m, more preferably ⁇ 100 ⁇ m and> 20 ⁇ m, preferably ⁇ 45 ⁇ m and> 20 ⁇ m, more preferably a plastic layer of polyethylene terephthalate (PET) which has been reduced by surface modification in their adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the layer structure according to the invention comprises a curable layer C and a substrate layer D, which is at least partially joined to the layer C, characterized in that the curable layer C
  • At least one multifunctional acrylate selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, 2- [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxyethyl prop-2-enoate,
  • III optionally comprises auxiliaries and additives.
  • D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate, preferably polycarbonate more preferably polycarbonate having an average molecular weight Mw of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative Solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ , or wherein D is a thermoplastic transparent plastic material layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , preferably ⁇ 45 ⁇ and> 20 ⁇ , more preferably a plastic layer of polyethylene terephthalate (PET), which has been reduced by surface modification in its adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the layer structure C-D according to the invention can be used in the method according to the invention described below and can be part of the kit-of-parts according to the invention.
  • the invention likewise provides a process for the production of the sealed holographic medium according to the invention, characterized in that a sealing layer comprising a curable layer C and a substrate layer D which is at least partially bonded to the curable layer C is present on a photopolymer B ' Hologram is applied to give a layer composite B'-CD, and thereafter the curable layer C is at least partially cured with actinic radiation to form a layer structure B'-CD.
  • III optionally comprises auxiliaries and additives
  • hologram-containing photopolymer layer B ' is obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives, and
  • the method according to the invention has the advantage that the sealing layer, comprising a layer C and a substrate layer D, is applied "dry", thereby avoiding the provision of expensive machines and specially trained personnel, as required, for example, for "wet” application. Due to the very good adhesion of the cured layer C both to the substrate layer D and to the photopolymer layer B 'a stable and difficult to separate layer composite is formed in which the hologram is securely encapsulated and sufficiently protected from external influences.
  • the photopolymer layer B ' is present on a substrate layer A or another carrier such as glass or plastic.
  • a layer composite AB "or D-C'-B ' is provided in a first step, wherein A is a substrate layer
  • the curable layer C is applied to the substrate layer D to form a layer composite
  • the layer composite CD is connected to the layer composite AB 'or to the layer composite D-C'-B', preferably by lamination, to form a layer composite A-B'-CD or a layer composite D- C'-B'-CD to give
  • the layer composite A-B'-CD or the layer composite D-C'-B'-CD actinic radiation is applied to a composite layer A -B 'C'-D or a layer composite D-C'-B'-C'-D to give.
  • At least partial curing of the layer C of the layer composite A-B'-C-D with actinic radiation takes place within 60 minutes, preferably within 5 minutes, more preferably within less than 60 seconds.
  • this comprises the following steps:
  • Producing a composite CD with a UV-curable layer C comprising: o preparing a coating agent for the production of the layer C; Coating the substrate D with this coating agent; Producing a holographic film with the layer structure A-B'-CD, comprising applying the layer composite CD on the layer composite AB 'followed by a planar connection of the two layer composites with each other, preferably by lamination, so that a layer composite A-B'-CD arises; - Applying to the layer composite A-B'-CD with actinic radiation preferably with
  • the curable layer C further contains at least one thermoplastic mainly linear partially crystalline polyurethane resin.
  • the multifunctional acrylate of the curable layer C is an at least tri-functional acrylate.
  • the acrylate is selected from the group consisting of phosphorothioyltris (oxybenzene-4, 1-diylcarbamoyloxyethane-2, 1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4, 1-diylcarbamoyloxyethane-2, 1-diyl) trisacrylate, 2 - [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxy] ethyl prop-2-enoate.
  • the acrylate is phosphorothioyltris (oxybenzene-4,
  • the layer C contains a UV Ab absorber, preferably in an amount of 0.01 to 10 wt .-%, more preferably in an amount of 0.1 to 5 wt .-%, each based on the total weight of the layer C.
  • the substrate layer D is a thermoplastic transparent plastic layer, in another preferred embodiment, the substrate layer D is a thermoplastic transparent amorphous plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent low-birefringence plastic layer. In a further preferred embodiment, the substrate layer D is an amorphous thermoplastic transparent low-birefringence plastic layer.
  • the substrate layer D consists of polycarbonate, copolycarbonate, polyethylene terephthalate, cellulose triacetate, polyamide, mixtures or material composites thereof. In another preferred embodiment, the substrate layer D consists of polycarbonate, copolycarbonate, cellulose triacetate, polyethylene terephthalate, mixtures or material composites thereof. In a preferred embodiment, the substrate layer D has a layer thickness of 5 ⁇ to 500 ⁇ , preferably 20 ⁇ to 150 ⁇ on.
  • the method according to the invention for the production of the sealed holographic medium according to the invention is characterized in that a sealing layer comprising a curable layer C and a surface-present substrate layer D at least partially bonded to the curable layer C comprises a photopolymer B ' a hologram is applied to form a laminate B'-CD, and thereafter the curable layer C is at least partially cured with actinic radiation to give a layer structure B'-C'-D, where C is the at least partially cured layer C is
  • III optionally comprises auxiliaries and additives
  • hologram-containing photopolymer layer B ' is obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives, and
  • D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate, preferably polycarbonate more preferably polycarbonate having an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ m preferably ⁇ 100 ⁇ m and> 20 ⁇ m, more preferably ⁇ 65 ⁇ m and> 20 ⁇ m, or where D is a thermoplastic transparent plastic layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , preferably ⁇ 45 ⁇ and> 20 ⁇ , more preferably a plastic layer of polyethylene terephthalate (PET) by Surface modification was reduced in their adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the inventive method for producing the sealed holographic medium according to the invention characterized in that a sealing layer, comprising a curable layer C and a curable layer C at least partially bonded, planar present substrate layer D, is applied to a photopolymer B 'containing a hologram to give a layer composite B'-CD, and then the curable layer C is at least partially cured with actinic radiation to a layer structure B'-C D, where C is the at least partially cured layer C,
  • At least one multifunctional acrylate selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, 2- [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxyethyl prop-2-enoate,
  • III optionally comprises auxiliaries and additives
  • hologram-containing photopolymer layer B ' is obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives, and
  • D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate, preferably of polycarbonate more preferably polycarbonate having an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ , or wherein D is a thermoplastic transparent plastic layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , preferably ⁇ 45 ⁇ and> 20 ⁇ , more preferably a plastic layer of polyethylene terephthalate (PET), the was reduced by surface modification in their adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the invention likewise relates to a sealed holographic medium comprising a layer structure A-B'-C'-D, a sealed holographic medium comprising a layered structure.
  • Construction B'-C'-D and a sealed holographic medium comprising a layer structure DC-B'-C'-D obtainable from the inventive method described above.
  • At least one hologram may be imprinted into the sealed holographic medium according to the invention.
  • the spectral shift of the transmission spectrum is defined as the difference ( ⁇ ) from the wavelength of the inscribing laser ( ⁇ ») and the spectral peak of the inscribed hologram (Xpeak) (ISO standard 17901 -1: 2015 (E)):
  • ⁇ of the inscribed hologram in the layer structure according to the invention A-B'-C'-D + / '- 10 nm, more preferably + /' - 5 nm, more preferably + / '- 3 nm.
  • kit-of-parts containing at least one planar photopolymer B 'which contains a hologram, preferably a volume hologram, and a sealing layer comprising a curable layer C and a surface layer at least partially bonded to the curable layer C.
  • Substrate layer D characterized in that the curable layer C
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives, and
  • the photopolymer layer B ' is present on a substrate layer A, wherein the photopolymer layer B' is at least partially connected to the substrate layer A on one side.
  • the photopolymer layer B ' is present as a layer composite DCB', the photopolymer layer B 'being at least partially connected to the uncured layer C.
  • the layer composite DCB ' can be produced as described above.
  • the photopolymer layer B ' is present as a layer composite D-C'-B', the photopolymer layer B 'being at least partially bonded to the hardened layer C.
  • the layer composite D-C'-B ' can be prepared as described above.
  • the curable layer C further contains at least one thermoplastic mainly linear partially crystalline polyurethane resin.
  • the multifunctional acrylate of the curable layer C is an at least trifunctional acrylate.
  • the acrylate is selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, 2- [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxy] ethyl prop-2-enoate.
  • the acrylate is phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate
  • the layer C contains a UV absorber, preferably in an amount of from 0.01 to 10% by weight, more preferably in an amount of from 0.1 to 5% by weight, in each case based on the total weight of the layer C.
  • the substrate layer D is a thermoplastic transparent plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent amorphous plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent low-birefringence plastic layer, in a further preferred embodiment, the substrate layer D is an amorphous thermoplastic transparent low-birefringence plastic layer. In a preferred embodiment, the substrate layer D consists of polycarbonate, copolycarbonate, polyethylene terephthalate, cellulose triacetate, polyamide, mixtures or material composites thereof. In another preferred embodiment, the substrate layer D consists of polycarbonate, copolycarbonate, cellulose triacetate, polyethylene terephthalate, mixtures or composite materials thereof. In a preferred embodiment, the substrate layer D has a layer thickness of 5 ⁇ to 500 ⁇ , preferably 20 ⁇ to 150 ⁇ on.
  • the kit-of-parts according to the invention comprises at least one planar photopolymer B 'which contains a hologram, preferably a volume holo gramme, and a sealing layer comprising a curable layer C and a curable layer C at least partially connected, present in a planar substrate layer D, characterized in that the curable layer C
  • III optionally comprises auxiliaries and additives
  • hologram-containing photopolymer layer B ' is obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives, and
  • D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate, preferably polycarbonate more preferably polycarbonate having an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ , or wherein D is a thermoplastic transparent plastic layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , preferably ⁇ 45 ⁇ and> 20 ⁇ , more preferably a plastic layer of polyethylene terephthalate (PET) by Surface modification was reduced in their adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the kit-of-parts according to the invention comprises at least one surface-present photopolymer B ', which contains a hologram, preferably a volume hologram, and a sealing layer comprising a curable layer C and a surface present at least partially connected to the curable layer C.
  • Substrate layer D characterized in that the curable layer C
  • At least one multifunctional acrylate selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, 2- [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxyethyl prop-2-enoate,
  • III optionally comprises auxiliaries and additives
  • hologram-containing photopolymer layer B ' is obtainable from an unexposed photopolymer B comprising
  • V) optionally catalysts, radical stabilizers, solvents, additives and other auxiliaries and / or additives, and
  • D is a thermoplastic transparent plastic layer of polycarbonate or copolycarbonate, preferably polycarbonate more preferably polycarbonate having an average molecular weight M "of from 18,000 to 40,000, more preferably from 26,000 to 36,000 and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration, or
  • D is a thermoplastic transparent plastic layer of cellulose triacetate (CTA or TAC), in particular a plastic layer of cellulose triacetate having a layer thickness of ⁇ 200 ⁇ more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ , or wherein D is a thermoplastic transparent plastic layer of polyester, in particular a plastic layer of polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ m, more preferably ⁇ 100 ⁇ m and> 20 ⁇ m, preferably ⁇ 45 ⁇ m and> 20 ⁇ m, more preferably a plastic layer of polyethylene terephthalate (PET) which has been reduced by surface modification in their adhesion properties.
  • CTA or TAC thermoplastic transparent plastic layer of cellulose triacetate
  • PET polyethylene terephthalate
  • the substrate layer A is preferably a thermoplastic substrate layer / substrate film or another carrier such as glass, plastic, metal or wood.
  • Materials or composite materials of the thermoplastic substrate layer A are based on polycarbonate (PC), polyethylene terephthalate (PET), amorphous polyesters, polybutylene terephthalate, polyethylene, polypropylene, cellulose acetate, cellulose hydrate, cellulose nitrate, cycloolefin polymers, polystyrene, hydrogenated polystyrene, polyepoxides, polysulfone, thermoplastic polyurethane ( TPU), cellulose triacetate (CTA), polyamide (PA), polymethyl methacrylate (PMMA), polyvinyl chloride, polyvinyl acetate, polyvinyl butyral or poly dicyclopentadiene or mixtures thereof.
  • PC polycarbonate
  • PET polyethylene terephthalate
  • PET amorphous polyesters
  • polybutylene terephthalate polyethylene
  • PMMA and ( " TA) material composites can be film laminates or coextrudates
  • Preferred material composites are duplex and triplex films constructed according to one of the schemes A / B, A / B / A or A / B / C.
  • PC / PMMA, PC are particularly preferred / PA, PC PET, PET PC PET and PC / TPU
  • Substrate Layer A is transparent in the spectral range of 400-800 nm
  • the photopolymer layer B ' is formed by writing a hologram into the unexposed photopolymer layer B, followed by optically fixing the hologram, preferably by two-dimensional UV / VI S broad-band exposure of the photopolymer layer with the inscribed hologram with a light energy dose of 5-10 J / cm 2 generated.
  • residues of very complex monomers which were not involved in the local formation of the hologram, are polymerized through the entire photopolymer layer.
  • the dyes used as sensitizers are also photochemically destroyed.
  • the strong technological discoloration of the photopolymer layer B caused by dyes disappears completely.
  • the photopolymer layer B is bleached by the fixation and turns into a non-photoactive, dye-free, stable photopolymer layer B 'with a inscribed hologram.
  • one or more holograms may be imprinted at the same location or side by side. If one illuminates at the same point, different image contents can be imprinted. Likewise, different views of an object can be imprinted with slightly varying reconstruction angles, resulting in stereograms. It is also possible to record hidden holograms and micro texts. Likewise, in the case of transmission holograms, it is possible to record several light-conducting functions and / or light-guiding functions for different spectral regions.
  • the photopolymer layer B comprises crosslinked matrix polymers, in particular three-dimensionally crosslinked matrix polymers, the matrix polymers preferably being polyurethanes.
  • the photopolymer layer B comprises matrix polymers, writing monomers and photoinitiators.
  • matrix polymers it is possible to use amorphous thermoplastics such as, for example, polyacrylates, polymethyl methacrylates or copolymers of methyl methacrylate, methacrylic acid or other alkyl acrylates and alkyl methacrylates and also acrylic acid such as polybutyl acrylate, polyvinyl acetate and polyvinylbiryrate its partially hydrolyzed derivatives such as polyvinyl alcohols and copolymers with ethylene and / or or further (meth) acrylates, gelatin, cellulose esters and cellulose ethers such as methylcellulose, cellulose acetobutyrate, silicones such as polydimethylsilicone, polyurethanes, polybutadienes and polyisoprenes, and also polyethylene oxides, Epoxy resins, in particular aliphatic epoxy resins, polyamides, polycarbonates, and the systems cited in US 49943
  • Epoxy resins can be cationically crosslinked with themselves. Furthermore, acid / anhydrides, amines, hydroxyalkylamides and thiols can also be used as crosslinking agents. Silicones can be crosslinked both as one-component systems by condensation in the presence of water (and, if necessary, under broenstic acid catalysis) or as two-component systems by addition of silicic acid esters or organotin compounds. Likewise, hydrosilylation is possible in vinyl silane systems.
  • Unsaturated compounds e.g. Acryloyl functional polymers or unsaturated esters can be crosslinked with amines or thiols.
  • a cationic vinyl ether polymerization is also possible.
  • the matrix polymers are crosslinked, preferably crosslinked three-dimensionally and most preferably are three-dimensionally crosslinked polyurethanes.
  • Polyurethane matrix polymers are obtainable in particular by reacting at least one polyisocyanate component a) with at least one isocyanate-reactive component b).
  • the polyisocyanate component a) comprises at least one organic compound having at least two NCO groups. These organic compounds may in particular be monomeric di- and triisocyanates, polyisocyanates and / or NCO-functional prepolymers.
  • the polyisocyanate component a) may also contain or consist of mixtures of monomeric di- and triisocyanates, polyisocyanates and / or NCO-functional prepolymers.
  • monomeric di- and triisocyanates it is possible to use all the compounds or mixtures thereof which are well known to the person skilled in the art. These compounds may have aromatic, aliphatic, aliphatic or cycloaliphatic structures. In minor amounts, the monomeric di- and tri-isocyanates may also be monoisocyanates, i. comprise organic compounds with an NCO group.
  • Suitable monomeric di- and triisocyanates are 1, 4-butane diisocyanate, 1,5-pentane diisocyanate, 1,6-hexane diisocyanate (hexamethylene diisocyanate, HDI), 2,2,4-trimethylhexamethylene diisocyanate and / or 2,4,4 Trimethylhexamethylene diisocyanate (TMDI), isophorone diisocyanate (IPDI), 1,8-diisocyanato-4- (iso-cy anatomethyl) -o-ctane, bis (4,4'-isocyanatocyclohexyl) methane and / or bis (2, 4isocyanatocyclohexyl) methane and / or mixtures thereof of any isomer content, 1,4-cyclohexane diisocyanate, the isomeric bis (isocyanatomethyl) cyclohexanes, 2,4- and / or 2,6-diiso
  • Suitable polyisocyanates are compounds having urethane, urea, carbodiimide, acylurea, amide, isocyanurate, allophanate, biuret, oxadiazinetrione, uretdione and / or iminooxadiazinedione structures which are selected from the abovementioned di- or tri-meres Triisocyanates are available.
  • the polyisocyanates are particularly preferably oligomerized aliphatic and / or cycloaliphatic di- or triisocyanates, it being possible in particular to use the abovementioned aliphatic and / or cycloaliphatic di- or triisocyanates.
  • Suitable prepolymers contain urethane and / or urea groups and optionally further structures formed by modification of NCO groups as mentioned above.
  • Such prepolymers are obtainable, for example, by reacting the abovementioned monomeric diisocyanates and triisocyanates and / or polyisocyanates a1) with isocyanate-reactive compounds b1).
  • isocyanate-reactive compounds bl) it is possible to use alcohols, amino or mercapto compounds, preferably alcohols. These may in particular be polyols. Very particular preference is given to using as the isocyanate-reactive compound bl) polyester, polyether, polycarbonate, poly (meth) acrylate and / or polyurethane polyols.
  • Suitable polyester polyols are, for example, linear polyester diols or branched polyester polyols which can be obtained in a known manner by reacting aliphatic, cycloaliphatic or aromatic di- or polycarboxylic acids or their anhydrides with polyhydric alcohols having an OH functionality> 2.
  • suitable di- or polycarboxylic acids are polybasic carboxylic acids such as succinic, adipic, cork, sebacic, decanedicarboxylic, phthalic, terephthalic, isophthalic, tetrahydrophthalic or trimellitic acid, as well as acid anhydrides such as phthalic, trimellitic or succinic anhydride or their arbitrary mixtures among themselves.
  • the polyester polyols can also be based on natural raw materials such as castor oil. It is likewise possible for the polyesterpolyols to be based on homopolymers or copolymers of lactones, which preferably by addition of lactones or lactone mixtures such as butyrolactone, r-caprolactone and / or methyl-e-caprolactone to hydroxy-functional compounds such as polyhydric alcohols of an OH -Functionality> 2, for example, the type mentioned below can be obtained.
  • suitable alcohols are all polyhydric alcohols, such as, for example, the C 2 -Cn-diols, the isomeric cyclohexanediols, glycerol or any desired mixtures thereof.
  • Suitable polycarbonate polyols are obtainable in a manner known per se by reacting organic carbonates or phosgene with diols or diol mixtures.
  • 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 known per se in the context of the polyester segments. Polyester polyols can also be converted to polycarbonate polyols.
  • Suitable polyether polyols are optionally blockwise polyaddition products of cyclic ethers with OH- or NH-functional starter molecules.
  • Suitable cyclic ethers are, for example, styrene oxides, ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide, epichlorohydrin and any desired mixtures thereof.
  • the starter used may be the polyhydric alcohols of OH functionality> 2 mentioned in the context of the polyesterpolyols and also primary or secondary amines and amino alcohols.
  • Preferred polyether polyols are those of the aforementioned type based solely on propylene oxide or random or block copolymers based on propylene oxide with further 1-alkylene oxides. Particular preference is given to propylene oxide homopolymers and also random or block copolymers which contain oxyethylene, oxypropylene and / or oxybutylene units, the proportion of oxypropylene units, based on the total amount of all oxyethylene, oxypropylene and oxybutylene units, being at least 20% by weight at least 45% by weight.
  • Oxypropylene and oxybutylene here include all respective linear and branched C3 and CV isomers.
  • isocyanate-reactive compounds are also low molecular weight, i. with molecular weights ⁇ 500 g / mol, short chain, i. 2 to 20 carbon atoms containing aliphatic, araliphatic or cycloaliphatic di-, tri- or polyfunctional alcohols suitable.
  • these may include neopentyl glycol, 2-ethyl-2-butylpropanediol, trimethylpentanediol, positionally isomeric diethyloctanediols, cyclohexanediol, 1,4-cyclohexanedimethanol, 1,6-hexanediol, 1, 2 and 1, 4-cyclohexanediol, hydrogenated bisphenol A, 2,2-bis (4-hydroxycyclohexyl) propane or 2,2-dimethyl-3-hydroxypropionic acid, 2,2-dimethyl-3-hydroxypropyl ester.
  • triols examples are trimethylolethane, trimethylolpropane or glycerol.
  • Suitable higher-functional alcohols are di (trimethylolpropane), pentaerythritol, dipentaerythritol or sorbitol. It is particularly preferred if the polyol component is a di-functional polyether, polyester or a polyether-polyester block copolyester or a polyether-polyester block copolymer having primary OH functions.
  • isocyanate-reactive compounds bl) amines are ethylenediamine, propyl endiamin, diaminocyclohexane, 4,4'-Dicylohexyl- menthanediamine, isophoronediamine (IPDA), difunctional polyamines such as Jeffamine ®, amine terminated polymers, and in particular having number average molecular weights ⁇ 10,000 g / mol. Mixtures of the aforementioned amines can also be used.
  • isocyanate-reactive compounds bl) amino alcohols are also possible to use as isocyanate-reactive compounds bl) amino alcohols.
  • suitable amino alcohols are the isomeric aminoethanols, the isomeric aminopropanols the isomeric aminobutanols and the isomeric aminohexanols or any desired mixtures thereof.
  • All of the aforementioned isocyanate-reactive compounds B1) can be mixed with one another as desired.
  • the isocyanate-reactive compounds bl) have a number average molecular weight of> 200 and ⁇ 10,000 g / mol, more preferably> 500 and ⁇ 8,000 g / mol and very particularly preferably> 800 and ⁇ 5,000 g / mol.
  • the OH functionality of the polyols is preferably 1.5 to 6.0, particularly preferably 1.8 to 4.0.
  • the prepolymers of the polyisocyanate component a) may in particular have a residual content of free monomeric di- and triisocyanates ⁇ 1% by weight, more preferably ⁇ 0.5% by weight and most preferably ⁇ 0.3% by weight.
  • the polyisocyanate component a) may comprise completely or proportionally organic compound whose NCO groups have been completely or partially reacted with blocking agents known from coating technology.
  • blocking agents are alcohols, lactams, oximes, malonic esters, pyrazoles and amines, such as e.g. Butanoxime, diisopropylamine, diethyl malonate, acetoacetic ester, 3, 5-dimethylpyrazole, ⁇ -caprolactam, or mixtures thereof.
  • the polyisocyanate component a) comprises compounds having aliphatically bonded NCO groups, aliphatic NCO groups being understood to mean those groups which are bonded to a primary carbon atom.
  • the cyano-reactive component b) preferably comprises at least one organic compound which has on average at least 1.5 and preferably from 2 to 3 isocyanate-reactive groups.
  • hydroxy, amino or mercapto groups are preferably considered as isocyanate-reactive groups.
  • the isocyanate-reactive component may in particular comprise compounds which have a number average of at least 1.5 and preferably 2 to 3 isocyanate-reactive groups.
  • Suitable polyfunctional, isocyanate-reactive compounds of component b) are, for example, the compounds bl) described above.
  • Photoinitiators which are suitable according to the invention are usually compounds which can be activated by actinic radiation and which can initiate a polymerization of the writing monomers. In the photoinitiators, a distinction can be made between unimolecular (type I) and bimolecular (type II) initiators. Furthermore, depending on their chemical nature, they are distinguished in photoinitiators for radical, anionic, cationic or mixed type of polymerization. Type I photoinitiators (Norrish type I) for radical photopolymerization form free radicals upon irradiation by unimolecular bond cleavage.
  • type I photoinitiators are triazines, oximes, benzoin ethers, benzil ketals, bisimidazoles, aroylphosphine oxides, sulfonium and iodonium salts.
  • Radical polymerization type II photoinitiators consist of a dye as a sensitizer and a coinitiator and undergo a bimolecular reaction upon irradiation with dye-adapted light. First, the dye absorbs a photon and transfers energy to the coinitiator from an excited state. It releases the polymerization-inducing radicals by electron or proton transfer or direct hydrogen abstraction.
  • type II photoinitiators are preferably used.
  • Dye and coinitiator of the type II photoinitiators can either be mixed directly together with the other components of the photopolymer or else premixed with individual components.
  • the dye with the isocyanate-reactive component and the coinitiator with the isocyanate component can be premixed.
  • photoinitiator systems are described in principle in EP 0 223 587 A and preferably consist of a mixture of one or more dyes with ammonium alkylaryl borate (s).
  • Suitable dyes which form a type II photoinitiator together with an ammonium alkylaryl borate are the cationic dyes described in WO 2012062655 in combination with the anions just described there.
  • Suitable ammonium alkylaryl borates are, for example, (Cunningham et al., RadTech'98 North America UV / EB Conference Proceedings, Chicago, Apr.
  • photoinitiators it may be advantageous to use mixtures of these photoinitiators.
  • the type and concentration of photoinitiator must be adapted in a manner known to the person skilled in the art. Further details are described, for example, in P.K.T. Oldring (Ed.), Chemistry & Technology of UV & EB Formulations For Coatings, Inks & Paints, Vol. 3, 1991, SITA Technology, London, pp. 61-328.
  • the photoinitiator comprises a combination of dyes whose absorption spectra at least partially cover the spectral range from 400 to 800 nm with at least one co-initiator adapted to the dyes.
  • At least one suitable for a laser light color of blue, green and red photoinitiator is included in the photopolymer formulation.
  • the photopolymer formulation contains at least two laser light colors selected from blue, green and red each contain a suitable photoinitiator.
  • the photopolymer formulation in each case contains a suitable photoinitiator for each of the laser light colors blue, green and red.
  • the writing monomers comprise a mono- and / or a multi-functional (meth) acrylate writing monomer.
  • the random monomers may additionally comprise at least one mono- and / or one multifunctional urethane (meth) acrylate.
  • Suitable acrylate writing monomers are in particular compounds of the general formula (I)
  • n> l and n ⁇ 4 and R is a linear, branched, cyclic or heterocyclic unsubstituted or optionally also substituted by hetero atoms organic radical and / or R 42 is hydrogen, a linear, branched, cyclic or heterocyclic unsubstituted or optionally also is heteroatom-substituted organic radical.
  • R 42 is particularly preferably hydrogen or methyl and / or R 41 is a linear, branched, cyclic or heterocyclic unsubstituted or optionally heteroatom-substituted organic radical.
  • esters of acrylic acid or methacrylic acid are referred to.
  • examples of preferably usable acrylates and methacrylates are phenyl acrylate, phenyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxyethoxyethyl acrylate, phenoxyethoxyethyl methacrylate, phenylthioethyl acrylate, phenylthioethyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 1,4-bis (2-thionaphthyl) -2 Butyl acrylate, 1, 4-bis (2-thionaphthyl) - 2-butyl methacrylate, bisphenol A diacrylate, bisphenol A dimethacrylate, and their ethoxylated analogues, N-carbazolyl.
  • Urethane acrylates in the present context are understood as meaning compounds having at least one acrylic acid ester group and at least one urethane bond. Such compounds can be obtained, for example, by reacting a hydroxy-functional acrylate or methacrylate with an isocyanate-functional compound.
  • Suitable isocyanate-functional compounds are monoisocyanates and the monomeric diisocyanates, triisocyanates and / or polyisocyanates mentioned under a).
  • suitable monoisocyanates are phenyl isocyanate, the isomeric methylthiophenyl cyanates.
  • Di, tri or polyisocyanates are mentioned above and triphenylmethane-4,4 ', 4 "-triisocyanat and tris (p-isocyanatophenyl) thiophosphate or derivatives thereof with urethane, urea, carbodiimide, acylurea, isocyanurate, Allophanate, biuret, oxadiazinetrione, uretdione, iminooxadiazinedione and mixtures thereof, aromatic, di-, tri- or polyisocyanates being preferred.
  • Suitable hydroxy-functional acrylates or methacrylates for the preparation of urethane acrylates are compounds such as 2-hydroxyethyl (meth) acrylate, polyethylene oxide mono- (meth) acrylates, polypropylene oxide mono (meth) acrylates, polyalkylene oxide mono (meth) acrylates, poly (8- caprolactone) mono (meth) acrylates, such as Tone ® Ml 00 (Dow, Schwalbach, Germany), 2-hydroxy propyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-hydroxy-2,2-dimethylpropyl (meth) acrylate, hydroxypropyl (meth) acrylate, acrylic acid (2-hydroxy-3-phenoxypropyl ester), the hydroxy-functional mono-, di- or tetraacrylates of polyhydric alcohols such as trimethylolpropane, glycerol, pentaerythritol, dipentaerythritol,
  • hydroxyl-containing epoxy (meth) acrylates known per se having OH contents of from 20 to 300 mg KOH / g or hydroxyl-containing polyurethane (meth) acrylates having OH contents of from 20 to 300 mg KOH / g or acrylated polyacrylates having OH contents of 20 to 300 mg KOH / g and mixtures thereof and mixtures with hydroxyl-containing unsaturated polyesters and mixtures with polyester (meth) acrylates or mixtures of hydroxyl-containing unsaturated polyester with polyester (meth) acrylates.
  • urethane acrylates are obtainable from the reaction of tris (p-isocyanato-phenyl) thiophosphate and / or mM ethylthiophenylisocyanate with alcohol-functional acrylates such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and / or hydroxybutyl (meth ) - acrylate.
  • the lean monomer further unsaturated compounds such as ⁇ , ⁇ -unsaturated carboxylic acid derivatives such as maleinates, fumarates, maleimides, acrylamides, further vinyl ethers, propenyl ethers, allyl ethers and dicyclopentadienyl units containing compounds and olefinically unsaturated compounds such.
  • unsaturated compounds such as ⁇ , ⁇ -unsaturated carboxylic acid derivatives such as maleinates, fumarates, maleimides, acrylamides, further vinyl ethers, propenyl ethers, allyl ethers and dicyclopentadienyl units containing compounds and olefinically unsaturated compounds such.
  • Styrene, ⁇ -methylstyrene, vinyltoluene and / or olefins such as ⁇ , ⁇ -unsaturated carboxylic acid derivatives such as maleinates, fumarates, maleimides, acryl
  • the photopolymer formulation additionally contains monomeric urethanes as additives, it being possible for the urethanes in particular to be substituted by at least one fluorine atom.
  • the urethanes may preferably have the general formula (II)
  • R 32 and R 53 are linear, branched, cyclic or heterocyclic unsubstituted or optionally also substituted by hetero atoms organic radicals and / or R 52 , R 53 independently Are hydrogen, wherein preferably at least one of R 51 , R 52 , R 53 is substituted with at least one fluorine atom and more preferably R 51 is an organic radical having at least one fluorine atom.
  • R 52 is particularly preferably a linear, branched, cyclic or heterocyclic unsubstituted or optionally also substituted by heteroatoms such as fluorine organic radical.
  • Stabilizers 0 to 40 wt .-%, preferably 10 to 30 wt .-% of monomeric fluorourethanes and 0 to 5 wt .-%, preferably 0.1 to 5 wt .-% further additives, wherein the sum of all components 100 wt .-% is.
  • photopolymers containing from 20 to 70% by weight of matrix polymers, from 20 to 50% by weight of sulfur monomers, from 0.001 to 5% by weight of photoinitiators, from 0 to 2% by weight of catalysts, from 0.001 to 1% by weight.
  • % Radical stabilizers optionally 10 to 30 wt .-% fluorourethanes and optionally used from 0.1 to 5 wt .-% of other additives.
  • urethanization catalysts e.g. organic or inorganic derivatives of bimuth, tin, zinc or iron (see also the compounds mentioned in US 2012/062658).
  • Particularly preferred catalysts are butyltin tris (2-ethylhexanoate), iron (III) tris-acetylacetonate, bismuth (III) tris (2-ethylhexanoate), and stannous bis (2-ethylhexanoate).
  • hindered amines can also be used as catalysts.
  • N-alkyl-HALS, N-alkoxy-HALS and N-alkoxy-ethyl-HALS compounds as well as antioxidants and / or UV absorbers are used.
  • flow control agents and / or antistatic agents and / or thixotropic agents and / or thickeners and / or biocides can be used.
  • the layer C comprises at least one multifunctional acrylate, optionally at least one physically drying polymeric resin, at least one photoinitiator and, if appropriate, auxiliaries and additives.
  • the layer C preferably additionally comprises a UV absorber in an amount of 0.1 to 10% by weight.
  • the at least one multifunctional acrylate is preferably selected from the group consisting of phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate, phosphorus oxytris (oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl) trisacrylate , 2 - [[4- [bis [4- (2-prop-2-enoyloxyethoxycarbonylamino) phenyl] methyl] phenyl] carbamoyloxy] ethyl prop-2-enoate, preferably an at least trifunctional acrylate, more preferably phosphorothioyl tris (oxybenzene-4, 1 - diylcarbamoyloxyethane-2, 1-diyl) trisacrylate, phosphoroxytris (oxybenzene-4, 1-diylcarbam
  • the optionally used physically drying resins for layer C are thermoplastic mainly linear partially crystalline polyurethanes (see, for example, Günter Oertel (ed.): Kunststoff-Handbuch Bd., 7 Polyurethanes, 3rd edition, Carl Hanser Verlag, 1993).
  • the polyurethanes are preferably the
  • thermo-activating adhesives mainly linear, partially crystalline polyurethanes for the layer C are described in DE 3729068 A1, DE 3702394 A1 and US 20050112971 A1, the disclosure of which is hereby incorporated by reference.
  • the photoinitiators used are usually activatable by actinic radiation compounds that can trigger a polymerization of the corresponding groups.
  • Type I photoinitiators for radical photopolymerization form free radicals upon irradiation by unimolecular bond cleavage.
  • type I photoinitiators are triazines, such as. Tris (trichloromethyl) triazine, oximes, benzoin ethers, benzil ketals, alpha-alpha-dialkoxyacetophenone, phenylglyoxylic acid esters, bis-imidazoles, aroylphosphine oxides, e.g. 2,4,6-trimethylbenzoyldiphenylphosphine oxide, sulfonium and iodonium salts.
  • Radical polymerization type II photoinitiators undergo a bimolecular reaction upon irradiation, the excited state photoinitiator reacting with a second molecule, the coinitiator, and the polymerization initiating radicals by electron or proton transfer or direct hydrogen abstraction forms.
  • type II photoinitiators are quinones, such as. B. camphorquinone, aromatic keto compounds, such as. Benzophenones in combination with tertiary amines, alkylbenzophenones, halogenated benzophenones, 4,4'-bis (dimethylamino) benzophenone (Michler's ketone), anthrone, methyl-p- (dimethylamino) benzoate, thioxanthone, ketocoumarine, alpha-aminoalkylphenone, alpha - Hydroxyalkylphenon and cationic dyes, such as. As methylene blue, in combination with tertiary amines. For the UV and short-wave visible range, type I and type II photoinitiators are used; for the longer wavelength visible light range, predominantly type II photoinitiators are used.
  • aromatic keto compounds such as. Benzophenones in combination with tertiary amines, alkylbenzophen
  • 1-hydroxy-cyclohexyl-phenyl ketone for example Irgacure® 184 from BASF SE
  • 2-hydroxy-2-methyl-1-phenyl-1-propanone for example Irgacure® 1173 from BASF SE
  • 2-hydroxy - 1 - ⁇ 4 - [4 - (2-hydroxy-2-methylpropionyl) benzyl] phenyl ⁇ -2-methylpropan-1-one eg Irgacure® 127 from BASF SE
  • 2-hydroxy-1-one [4- (2-hydroxyethoxy) phenyl] -2-methyl-1-propanone eg Irgacure® 2959 from BASF SE
  • 2,4,6-trimethylbenzoyl-diphenylphosphine oxides e.g., Lucirin® TPO from BASF SE
  • 2,4,6-trimethylbenzoyl-diphenyl-phosphinate e.g., Lucirin® TPO-L from BASF SE
  • UV absorbers are benzotriazoles, cyanoacrylates, benzophenones, phenyltriazines, hydroxyphenyltrazines or oxalanilides.
  • Substrate layer D can contain chelating agents such as phenols or HALS amines.
  • the substrate layer D is preferably a thermoplastic substrate layer / substrate film.
  • Thermoplastic Substrate Resins or Composites are based on polycarbonate (PC), polyethylene terephthalate (PET), amorphous polyesters, polybutylene terephthalate, polyethylene, polypropylene, cellulose acetate, cellulose hydrate, cellulose nitrate, polystyrene, hydrogenated polystyrene, polyepoxides, Polysulfone (Ultrason® from the manufacturer BASF or Udel® from the manufacturer Solvay), thermoplastic polyurethane (TPU), cellulose eretriacetate (CTA), polyamide (PA), polymethyl methacrylate (PMMA), polyvinyl chloride, polyvinyl acetate, polyvinyl butyral or polycyclopentane entadiene or mixtures thereof, cycloolefin polymers and cycloolefm copolymers (COC, eg
  • PC. PET, PA. PMMA and CTA are based on PC. PET, PA. PMMA and CTA.
  • they are based on polycarbonate, polyethylene terephthalate, cellulose triacetate, polyamide, mixtures or composite materials thereof.
  • Composite materials may be film laminates or co-extrudates.
  • Preferred material composites are duplex and triplex films constructed according to one of the schemes A / B, A / B / A or AB / C.
  • Particularly preferred are PC PMMA, PC PA, PC PET, PET PC PET and PC / TPU.
  • substrate film D is transparent in the spectral range of 400-800 nm.
  • the substrate layer D is a thermoplastic transparent plastic layer.
  • the substrate layer D is a thermoplastic transparent amorphous plastic layer. In another preferred embodiment, the substrate layer D is a thermoplastic transparent low-birefringence plastic layer. In a further preferred embodiment, the substrate layer D is an amorphous thermoplastic transparent low-birefringence plastic layer.
  • the substrate layer D has a layer thickness of 5 ⁇ to 500 ⁇ , preferably 20 ⁇ to 150 ⁇ on.
  • the substrate layer D consists of polycarbonate, copolycarbonate, polyethylene terephthalate, cellulose triacetate, polyamide, mixtures or composite materials thereof. In another preferred embodiment, the substrate layer D consists of polycarbonate, copolycarbonate, cellulose triacetate, polyethylene terephthalate, mixtures or composite materials thereof.
  • the film D comprises polycarbonate or copolycarbonate.
  • Suitable polycarbonates for the production of the polycarbonate films according to the invention are all known polycarbonates. These are homopolycarbonates, copolycarbonates and thermoplastic polyestercarbonates.
  • the suitable polycarbonates preferably have an average molecular weight M w of from 18,000 to 40,000, more preferably from 26,000 to 36,000, and most preferably from 28,000 to 35,000, determined by measuring the relative solution viscosity in dichloromethane or by gel permeation chromatography and polycarbonate calibration.
  • the preparation of the polycarbonates is preferably carried out by the interfacial process or the melt transesterification process, which are variously described in the literature.
  • interfacial process see, for example, H. Schnell, Chemistry and Physics of Polycarbonates, Polymer Reviews, Vol. 9, Interscience Publishers, New York 1964, p. 33 et seq., Polymer Reviews, Vol. 10, "Condensation Polymers by Interfacial and Solution Method ", Paul W.
  • the polycarbonates can be obtained from reactions of bisphenol compounds with carbonic acid compounds, in particular phosgene or in the melt transesterification process of diphenyl carbonate or dimethyl carbonate. These are homopolycarbonates based on bisphenol-A and copolycarbonates based on the monomers bisphenol A and 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane are particularly preferred.
  • Other bisphenol compounds which can be used for the polycarbonate synthesis are disclosed inter alia in WO-A 2008037364, EP-A 1 582 549, WO-A 2002026862, WO-A 2005113639.
  • the polycarbonates may be linear or branched. It is also possible to use mixtures of branched and unbranched polycarbonates.
  • Suitable branching agents for polycarbonates are known from the literature and described for example in the patents US-B 4 185 009, DE-A 25 00 092, DE-A 42 40 313, DE-A 19 943 642, US-B 5 367 044 and US Pat in literature cited herein.
  • the polycarbonates used can also be intrinsically branched, in which case no branching agent is added during the polycarbonate production.
  • An example of intrinsic branching are so-called frieze structures, as disclosed for melt polycarbonates in EP-A 1 506 249.
  • chain terminators can be used in polycarbonate production.
  • chain terminators it is preferred to use phenols such as phenol, alkylphenols such as cresol and 4-tert-butylphenol, chlorophenol, bromophenol, cumylphenol or mixtures thereof.
  • the plastic composition (s) of the film may additionally contain additives such as UV absorbers, I R absorbers and other conventional processing aids, in particular mold release agents and flow agents, as well as the usual stabilizers, in particular heat stabilizers and antistatic agents, pigments, colorants and optical brighteners. In each layer different additives or concentrations of additives may be present.
  • additives such as UV absorbers, I R absorbers and other conventional processing aids, in particular mold release agents and flow agents, as well as the usual stabilizers, in particular heat stabilizers and antistatic agents, pigments, colorants and optical brighteners.
  • the substrate layer D is a highly transparent, amorphous and mechanically stable film substrates of cellulose triacetate (CTA or TAC), in particular those such as e.g. TAC with a layer thickness ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 65 ⁇ and> 20 ⁇ .
  • CTA or TAC cellulose triacetate
  • examples of these are Tacphan® 91 5 (50 ⁇ ) of the company LOFO High Tech Film GmbH, Weil am Rhein, Germany and TAC film ZRD60SL 60 ⁇ Fa. Fuji Film Europe GmbH, Dusseldorf, Germany.
  • the substrate layer D is a mechanically stable thermoplastic plastic substrates made of polyester, in particular those such as polyethylene terephthalate (PET) with a layer thickness of ⁇ 200 ⁇ , more preferably ⁇ 100 ⁇ and> 20 ⁇ , more preferably ⁇ 45 ⁇ and> 20 ⁇ , which were reduced by surface modification in their adhesion properties.
  • PET polyethylene terephthalate
  • inorganic slip additives can be added, such as kaolin, clay, bleaching earth, calcium carbonate, silica, alumina, titanium oxide, Cal ciumpho sphat which are added in up to 3%.
  • three-layer coextrudate films are also used in which only the outer layers contain such inorganic slip additives (eg Hostaphan RNK).
  • the invention likewise relates to the use of the layered structures according to the invention and the kit-of-parts according to the invention for protecting a photopolymer B 'containing a volume hologram, preferably wherein the photopolymer B' comprises three-dimensionally crosslinked matrix polymers, particularly preferably a three-dimensionally crosslinked polyurethane matrix.
  • the sealed holographic medium according to the invention contains a
  • Hologram-containing photopolymer layer having a layer thickness of 0.3 ⁇ to 500 ⁇ , preferably from 0.5 ⁇ to 200 ⁇ and more preferably from 1 ⁇ to 100 ⁇ .
  • the hologram may be a reflection, transmission, in-line, off-axis, full aperture transfer, white light transmission, denisy, off-axis reflection or edge-lit hologram, as well as a holographic stereogram and preferably a reflection, transmission or edge-lit hologram be. Preference is given to reflection holograms, denisy holograms, transmission holograms.
  • one or more holograms may be imprinted at the same location or side by side. If you illuminate at the same point, different image contents can be imprinted. Also, different views of an object can be imprinted with slightly varying reconstruction angles, resulting in stereograms. It is also possible to record hidden holograms and micro texts. Likewise, in the case of transmission holograms, it is possible to record several light-conducting functions and / or light-conducting functions for different spectral regions. Possible optical functions of the holograms correspond to the optical functions of light elements such as lenses, mirrors, deflection mirrors, filters, diffusers, directional diffusers, diffraction elements, light guides, waveguides, projection disks and / or masks.
  • light elements such as lenses, mirrors, deflection mirrors, filters, diffusers, directional diffusers, diffraction elements, light guides, waveguides, projection disks and / or masks.
  • holograms can be combined in such a hologram, for example so that the light is diffracted in a different direction depending on the incidence of light.
  • autostereoscopic or holographic electronic displays can be built, which allow a stereoscopic visual impression without further aids such as a polarizer or shutter glasses to experience the use in automotive head-up displays or head-mounted displays.
  • these optical elements exhibit specific frequency selectivity depending on how the holograms have been exposed and what dimensions the hologram has. This is especially important when using monochromatic light sources such as LED or laser light. So you need a hologram per complementary color (RGB) to direct light frequency-selective and at the same time to enable full-color displays. Therefore, several holograms are to be exposed to one another in the medium in certain display structures.
  • RGB complementary color
  • holographic images or representations such as for personal portraits, biometric representations in security documents, or generally of images or image structures for advertising, security labels, trademark protection, branding, labels, design elements, decorations, illustrations, trading cards , Images and the like, as well as images that can represent digital data, among others also be produced in combination with the products shown above.
  • Holographic images can have the impression of a three-dimensional image, but they can also represent image sequences, short films or a number of different objects, depending on which angle, with which (even moving) light source, etc., this is illuminated. Because of these diverse design possibilities, holograms, in particular volume holograms, represent an attractive technical solution for the above-mentioned application. It is also possible to use such holograms for storing digital data using a wide variety of exposure methods (shift, spatial or angular multiplexing) , The invention likewise provides an optical display comprising a sealed holographic medium according to the invention.
  • optical displays are based on liquid crystals, organic light-emitting diodes (OLED), LED display panels, microelectromechanical systems (MEMS) based on diffractive light selection, electrowetting displays (e-ink) and plasma screens.
  • Such visual displays can be autostereoscopic and / or holographic displays, transmissive and reflective projection screens or projection screens, displays with switchable restricted radiation behavior for privacy filters and bidirectional multiuser screens, virtual screens, head-up displays, head-mounted displays, light symbols, warning lamps, signal lamps , Headlights and display boards.
  • the invention also relates to autostereoscopic and / or holographic displays, projection screens, projection screens, displays with switchable restricted radiation behavior for privacy filters and bidirectional multiuser screens, virtual screens, head-up displays, head-mounted displays, light symbols, warning lamps, signal lamps, headlights and display panels comprising a holographic medium according to the invention.
  • Still further objects of the invention are a security document and a holographic optical element comprising a sealed holographic medium according to the invention.
  • a holographic medium according to the invention for the production of chip cards, identity documents, 3D images, product protection labels, lab, banknotes or holographic optical elements, in particular for optical displays, is also an object of the invention.
  • Solid-state hardness The specified solids contents were determined in accordance with DIN EN ISO 3251.
  • Fomrez® UL 28 urethanization catalyst commercial product of Momentive Performance
  • Polyisocyanate proportion of iminooxadiazinedione at least 30%, NCO content: 23.5%.
  • Dye 1 (3,7-bis (diethylamino) phenoxazine-5-ium bis (2-ethylhexyl) sulfosuccinic acid ester) was prepared as described in WO 2012062655.
  • Polyol 1 was prepared as described in WO2015091427.
  • Urethane acrylate 1 at the same time also MAc 1, (phosphorothioyltris (oxybenzene-4,1-diylcarbamoyloxy-ethane-2, 1-diyl) trisacrylate, [1072454-85-3]) was prepared as described in WO2015091427.
  • Urethane acrylate 2 (2- ( ⁇ [3- (methylsulfanyl) phenyl] carbamoyl ⁇ oxy) ethylprop-2-enoate, [1207339-61-4]) was prepared as described in WO2015091427.
  • Desmocoll 400/3 - Resin 1 A linear thermoplastic flexible polyurethane from Covestro
  • Desmocoll 530/3 - Resin 2 A linear thermoplastic flexible polyurethane from Covestro
  • Degacryl M547 - Resin 4 A linear thermoplastic, amorphous polymethyl methacrylate having a Mw of 500,000 from Evonik Industies, Marl, Germany
  • MAc 1 phosphorothioyl tris (oxybenzene-4,1-diylcarbamoyloxyethane-2, 1-diyl) trisacrylate, [1072454-85-3]) was prepared as described in WO2015091427.
  • Photoinitiators Esacure One - Initiator 1 [163702-01 -0] 01igo- [2-hydroxy-2-methyl-1- ((4- (1-methylvinyl) -phenyl) propanone] from Lamberti S.p.A., Albizzate, Italy.
  • Irgacure 4265 - Initiator 2 A blend of Irgacure® TPO (50% wt.%) And Irgacure®
  • EA Ethyl acetate
  • Methoxypropanol (MP-ol) 1-methoxy-2-propanol from Brenntag GmbH, Mülheim an der Ruhr, Germany
  • Kaneka PC - Di polycarbonate film from the company Kaneka Corp., Tokyo, Japan. Layer thickness 66 ⁇ .
  • ZRD60SL D3 Cellulose triacetate film Z-TAC "ZRD60SL from FujiFilm Europe
  • this solution was in a roll to roll coating system on a 36 ⁇ thick PET film, where by means of a doctor blade, the product was applied in a wet layer thickness of 19 ⁇ .
  • the coated film was dried and then protected with a 40 ⁇ m thick polyethylene film. Subsequently, this film was packed light-tight.
  • the coating compositions C-01 to C-04 as well as the non-inventive coating compositions C-N01 and C-N02 were applied in a roll to roll coating unit by means of a squeegee s on the film substrates D l, D2 and D3.
  • a drying temp erature of 85 ° C and a drying time of 5 minutes the coated film was dried and then protected with a 40 ⁇ thick polyethylene film.
  • the coating thickness was usually 15-16 ⁇ . Subsequently, this film was packed light-tight. Production of test holograra lara in composite film AB
  • Test holograms were prepared as follows: the photopolymer sheets with layer structure A-B were cut to the desired size in the dark and laminated by means of a rubber roller to a 50 mm x 70 mm (3 mm thick) glass plate.
  • the production of test holograms was carried out by a test apparatus which generates Denisyuk reflection holograms by means of green (532 nm) laser radiation.
  • the test apparatus consists of a laser source, an optical beam guidance system and a holder for the glass coupons.
  • the holder for the glass coupons is mounted at an angle of 13 ° relative to the beam axis.
  • the laser source generated the radiation, which was guided over a special optical beam path to about 5 cm expanded to the glass coupon, which was in optical contact with the mirror.
  • the holographed object was an approx. 2 cm x 2 cm large mirror, so that the reconstruction of the hologram reconstructed the wave front of the mirror. All examples were exposed to a green 532 nm laser (Newport ⁇ , ⁇ , CA, USA, stock number EXLSR-532-50-CDRH). By means of a shutter, the recording film was exposed for 2 seconds. This results in a film composite A-B * with a hologram in the layer B.
  • the samples were placed with the B side toward the lamp on the conveyor belt of a UV lamp and exposed twice with a bending speed of 2.5 m / min.
  • the UV emitter was an iron - doped H - lamp of the type Fusion UV type "D Bulb" no. 558434 KR 85 with 80 W / cm 2 total power density used.
  • the parameters corresponded to a dose of 2 ⁇ 2.5 J / cm 2 (measured with a light bug of the type I LT 490).
  • the holograms in layer B 'of the film composite A-B' were now measured spectroscopically and the quality of the holograms evaluated.
  • the diffractive reflection of such holograms can be analyzed in transmission due to the high diffraction efficiency of the volume hologram with visible light using a spectrometer (USB 2000, Ocean Optics, Dunedin, FL, USA) and appears in the transmission spectrum as a peak with reduced transmission T Rcd .
  • a spectrometer USB 2000, Ocean Optics, Dunedin, FL, USA
  • the quality of the hologram can be determined according to ISO standard 17901 -1: 2015 (E). The following parameters are considered, all results are shown in Table 3 in the section "Spectral quality of the holograms" column Summarized in 'AB'": (l) Maximum depth of the transmission peak, which corresponds to the highest
  • TR « serves as a measure of the reflection force (or visible" strength "or” quality ") of the hologram.
  • the films with the layer structure A-B ' were then provided with the sealing layer / adhesive film C-D in the process according to the invention.
  • the holograms were then re-examined according to their quality in the layer structure A-B'-C'-D and compared with the original values for the layer structure A-B ', see the values for ⁇ (Table 3).
  • the film composite with the layer structure A-B'-C'-D is produced by a lamination of the side B 'of the layer composite / the film AB' on the side C of the layer composite / the film CD. This was done by compressing the two films between the rubber rollers of a laminator. The temperature of the rolls was set at 30 ° C, 60 ° C or 90 ° C. The produced multilayer film was cooled to room temperature. Subsequently, the samples A-B'-CD were placed with the D side toward the lamp on the conveyor belt of a UV lamp and exposed twice at a line speed of 2.5 m / min.
  • the UV emitter was an iron-doped Hg lamp of the Fusion UV type "D Bulb" no.
  • the film composite AB '-C' -D is formed.
  • Table 2 shows that all the samples of the invention can be readily prepared by lamination and UV cure steps.
  • Non-inventive sample C-N02-D2 can not be produced.
  • T Rcd l 00-T pe ak (A-B'-cD) (1) for the samples according to the invention differ only minimally from the corresponding values for AB 'and only in isolated cases now reach almost 9%. A large loss of the hologram quality of 19% is recorded only for the non-inventive example C-N01-D2.
  • the spectral peak is not uniform in this case, indicating damage to the hologram.

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Abstract

L'invention concerne un moyen holographique scellé comprenant une structure stratifiée contenant une couche de photopolymère et une couche de scellement, un procédé de fabrication du moyen holographique scellé, une pièce d'un kit, une structure stratifiée destinée au scellement, ainsi que leur utilisation.
EP18721071.1A 2017-05-09 2018-05-08 Feuille plastique dotée d'une couche de colle durcissable aux uv et destinée à la protection d'un hologramme en composite de feuilles-photopolymère Withdrawn EP3622353A1 (fr)

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US20200241471A1 (en) 2020-07-30
CN110603495B (zh) 2022-03-11
KR20200005739A (ko) 2020-01-16

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