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DE102004053817A1 - Acrylic glass with photochromic properties - Google Patents

Acrylic glass with photochromic properties Download PDF

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Publication number
DE102004053817A1
DE102004053817A1 DE102004053817A DE102004053817A DE102004053817A1 DE 102004053817 A1 DE102004053817 A1 DE 102004053817A1 DE 102004053817 A DE102004053817 A DE 102004053817A DE 102004053817 A DE102004053817 A DE 102004053817A DE 102004053817 A1 DE102004053817 A1 DE 102004053817A1
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DE
Germany
Prior art keywords
methacrylate
intermediate layer
poymethyl
sandwiches
polymethyl methacrylate
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.)
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DE102004053817A
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German (de)
Inventor
Hans Lichtenstein
Günther Ittmann
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Roehm GmbH Darmstadt
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Roehm GmbH Darmstadt
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Application filed by Roehm GmbH Darmstadt filed Critical Roehm GmbH Darmstadt
Priority to DE102004053817A priority Critical patent/DE102004053817A1/en
Priority to CA002580765A priority patent/CA2580765A1/en
Priority to KR1020077010075A priority patent/KR20070074597A/en
Priority to EP05791361A priority patent/EP1807261A1/en
Priority to CNA2005800314417A priority patent/CN101022950A/en
Priority to PCT/EP2005/010556 priority patent/WO2006048089A1/en
Priority to AU2005300858A priority patent/AU2005300858A1/en
Priority to BRPI0517270-5A priority patent/BRPI0517270A/en
Priority to JP2007539479A priority patent/JP2008518809A/en
Publication of DE102004053817A1 publication Critical patent/DE102004053817A1/en
Priority to ZA200703580A priority patent/ZA200703580B/en
Withdrawn legal-status Critical Current

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    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B32B27/22—Layered products comprising a layer of synthetic resin characterised by the use of special additives using plasticisers
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
    • E04C2/00—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels
    • E04C2/54—Slab-like translucent 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
    • B32B2250/00—Layers arrangement
    • B32B2250/03—3 layers
    • 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
    • B32B2250/00—Layers arrangement
    • B32B2250/24—All layers being polymeric
    • B32B2250/246—All polymers belonging to those covered by groups B32B27/32 and B32B27/30
    • 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
    • B32B2250/00—Layers arrangement
    • B32B2250/40—Symmetrical or sandwich layers, e.g. ABA, ABCBA, ABCCBA
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/402—Coloured
    • B32B2307/4026—Coloured within the layer by addition of a colorant, e.g. pigments, dyes
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/42—Polarizing, birefringent, filtering
    • 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
    • B32B2419/00—Buildings or parts thereof

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  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Laminated Bodies (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Die Erfindung betrifft Polymethylmethacrylat mit phototropen Eigenschaften, Verfahren zur Herstellung und Verwendungen.The invention relates to polymethylmethacrylate having photochromic properties, to processes for preparation and to uses.

Description

Die Erfindung betrifft ein Acrylglas mit phototropen Eigenschaften, Verfahren zur Herstellung und Verwendungen.The Invention relates to an acrylic glass with photochromic properties, Process for production and uses.

Schon seit längerer Zeit gibt es Farbstoffe, die lichtabhängig den Farbton und die Intensität ändern. Die Verwendung dieser Farbstoffe in Kunststoffen ist bekannt. Die Farbstoffe können jedoch nicht in eine beliebige Kunststoffmatrix eingearbeitet werden. Um die Wirkung zu entfalten, muß dem Farbstoffmolekül soviel Beweglichkeit gelassen werden, dass dies durch Isomerie den Farbeffekt entfalten kann. In der Mehrzahl werden Polyurethane verwendet, da sie eine geeignete Matrix für die Farbstoffe bieten.Nice for a long time There are dyes that change the color and intensity depending on the light. The Use of these dyes in plastics is known. The dyes can but not incorporated into any plastic matrix. Around to develop the effect, must the dye molecule so much flexibility that this is due to isomerism Color effect can unfold. The majority use polyurethanes, because they are a suitable matrix for the dyes offer.

Polymethylmethacrylat ist durch seine Härte als Kunststoffmatrix für diese Farbstoffe nicht geeignet, da es den Farbstoffmolekülen nicht die notwendige Bewegungsfreiheit lässt. Durch die Zugabe größerer Mengen an Weichmachern oder weich machenden Comonomeren wird das System wirksam. Allerdings wird dabei das Material so weich, dass es den Anforderungen für die jeweiligen Anwendungen nicht mehr entspricht.polymethylmethacrylate is characterized by its hardness Plastic matrix for these dyes are not suitable because it does not affect the dye molecules the necessary freedom of movement leaves. By adding larger quantities plasticizers or softening comonomers become the system effective. However, the material is so soft that it is the Requirements for the respective applications no longer corresponds.

Aufgabe war es daher, ein Polymethylmethacrylat mit phototropen Eigenschaften herzustellen.task It was therefore a polymethyl methacrylate with photochromic properties manufacture.

Die Aufgabe wurde gelöst durch Poymethylmethacrylat-Sandwiches, enthaltend zwei Polymethylmethacrylat-Platten und eine Zwischenschicht, die phototrope Farbstoffe enthält.The Task has been solved by poymethyl methacrylate sandwiches containing two polymethyl methacrylate plates and an intermediate layer containing photochromic dyes.

Überraschend wurde gefunden, dass mit einem Sandwichaufbau, Polymethylmethacrylat (PMMA) mit phototropen Eigenschaften hergestellt werden kann. Hierbei liefern die beiden äußeren PMMA-Platten die mechanische Stabilität, die weiche Zwischenschicht ermöglicht die Einbringung phototroper Farbstoffe.Surprised was found to be using a sandwich construction, polymethylmethacrylate (PMMA) can be produced with photochromic properties. in this connection deliver the two outer PMMA plates the mechanical stability, the soft intermediate layer allows the incorporation of photochromic dyes.

Es wurde gefunden, dass die äußeren PMMA-Platten mit den bekannten Zusätzen modifiziert werden können. Vorzugsweise können Lichtschutzmittel eingearbeitet werden. Besonders geeignet sind Zusätze, die nur kurzwelliges UV-Licht filtern, wie z.B. Bisoxaniline oder Verbindungen aus der Gruppe der HALS (Hindered Amin Light Stabilizer).It it was found that the outer PMMA plates with the known additives can be modified. Preferably Light stabilizers are incorporated. Particularly suitable additives are only filter shortwave UV light, e.g. Bisoxanilines or compounds from the group of HALS (hindered amine light stabilizer).

Außerdem können die PMMA-Platten Farbstoffe enthalten, die UV-Licht durchlässig sind.In addition, the PMMA plates contain dyes that are permeable to ultraviolet light.

Die Zwischenschicht muß so weich sein, dass den Farbstoffmolekülen genug Beweglichkeit bleibt, durch Isomerie den Farbumschlag zu erzeugen.The Interlayer must be like that be soft enough to give the dye molecules enough mobility to produce the color change by isomerism.

Überraschend wurde gefunden, dass für die Zwischenschicht Polymethylmethacrylate mit Weichmachern und/oder Comonomeren geeignet sind. Als Weichmacher können alle handelsüblichen Zusätze, wie Adipate, Phthalate, Phosphate oder Zitrate verwendet werden. Besonders bevorzugt werden Di-n-Butyladipat und Diisobutylphthalat als Weichmacher zugegeben.Surprised was found that for the intermediate layer polymethyl methacrylates with plasticizers and / or Comonomers are suitable. As a plasticizer, all commercially available Accessories, like Adipates, phthalates, phosphates or citrates are used. Especially preferred are di-n-butyl adipate and diisobutyl phthalate added as a plasticizer.

Als Comonomere können viele PMMA-verträgliche Monomere verwendet werden. Verbindungen aus der Klasse der Acrylate oder höher alkylierten Methacrylate sind besonders geeignet.When Comonomers can many PMMA-compatible Monomers can be used. Compounds of the class of acrylates or higher Alkylated methacrylates are particularly suitable.

Es wurde gefunden, dass die Zwischenschicht auch vollständig aus Polyacrylaten oder höher alkylierten Polymethacrylaten bestehen kann. Es hat sich gezeigt, dass besonders Propyl-, Butyl- und längerkettige Methacrylate geeignet sind.It it was found that the interlayer is also completely off Polyacrylates or higher alkylated polymethacrylates can exist. It has shown, that especially propyl, butyl and longer chain methacrylates suitable are.

In die Zwischenschicht können alle bekannten phototropen Farbstoffe eingebracht werden. Bevorzugt werden Farbstoffe aus der Gruppe der Spiro-naphthoxazine und Naphthopyrane verwendet. Besonders bevorzugt sind photochrome Reversacol Farbstoffe der Fa. J. Robinson (Huddersfield, England), wie z.B. Gray 219, Gray 208, Gray 306, Gray 195, Brown 105, Flamme 29 B, Sea Green 5, Velvet Blue, Sunflower, Graphite und Palatinate Purple.In the intermediate layer can All known phototropic dyes are introduced. Prefers are dyes from the group of spiro-naphthoxazines and naphthopyrans used. Particularly preferred are photochromic Reversacol dyes J. Robinson (Huddersfield, England), e.g. Gray 219, Gray 208, Gray 306, Gray 195, Brown 105, Flame 29 B, Sea Green 5, Velvet Blue, Sunflower, Graphite and Palatinate Purple.

Diese Farbstoffe werden der Kunststoffmatrix in Abhängigkeit von der Schichtdicke zugegeben. Eine geringe Dicke erfordert eine hohe Konzentration. So werden beispielsweise bei einer Dicke von 3mm die Farbstoffe in Mengen von 0,001 % bis 0,3% zugegeben. Bei geringen Schichtdicken können bis zu 10% Farbstoffe zugegeben werden. Es wurde gefunden, dass gute phototrope Eigenschaften nachweisbar sind, wenn die Dicke der Zwischenschicht zwischen 0,01 und 5 mm liegt. Die besten Ergebnisse wurden bei Schichtdicken zwischen 0,1 und 3 mm erzielt. Es können auch Mischungen verschiedener Farbstoffe verwendet werden.These Dyes become the plastic matrix depending on the layer thickness added. A small thickness requires a high concentration. For example, at a thickness of 3mm, the dyes become in amounts of 0.001% to 0.3%. For small layer thicknesses can Up to 10% of dyes are added. It was found that good photochromic properties are detectable when the thickness of the Intermediate layer is between 0.01 and 5 mm. The best results were achieved at layer thicknesses between 0.1 and 3 mm. It can too Mixtures of different dyes are used.

Es wurde gefunden, dass die erfindungsgemäßen Sandwiches mit verschiedenen Verfahren hergestellt werden können. Besonders geeignet ist das Kammergussverfahren. Hierbei werden die Polymethylmethacrylat-Platten separat im Kammergussprozeß hergestellt. In Abhängigkeit von der Dicke der Platten werden Temperatur und Zeit der Temperung festgelegt. Es können die herkömmlichen Zusätze, wie z.B. UV-Filter, Initiatoren, Farbstoffe oder Stabilisatoren zugegeben werden. Anschließend wird die Zwischenschicht mit den entsprechenden Zusätzen, wie z.B. phototrope Farbstoffe und gegebenenfalls Weichmacher, zwischen die Polymethylmethacrylat-Platten gegossen. Über Quellprozesse wird der Verbund hergestellt. Die PMMA-Platten können mit Vernetzern versetzt werden, um die Quellung zu regulieren.It has been found that the sandwiches according to the invention can be prepared by various processes. Particularly suitable is the chamber casting method. Here, the polymethyl methacrylate plates are manufactured separately in the chamber casting process. Depending on the thickness of the plates, the temperature and time of tempering are determined. It can be added to the conventional additives, such as UV filters, initiators, dyes or stabilizers. Subsequently, the intermediate layer with the appropriate additives, such as photochromic dyes and optionally Plasticizer, poured between the polymethyl methacrylate plates. The composite is produced via source processes. The PMMA plates can be treated with crosslinkers to regulate the swelling.

Außerdem ist das Innen-Coextrusionsverfahren zur Herstellung der erfindungsgemäßen Sandwiches geeignet. In EP1270176 wird ein Verfahren zur Herstellung von mehrschichtigen Hohlkammerprofilplatten beschrieben. Hierbei wird eine obere und eine untere Schicht aus einer Kunststoffschmelze und einer im Inneren des Hohlkammerprofils liegenden Schicht aus einer Kunststoffschmelze auf dem Wege der Coextrusion der Kunststoffschmelze und unter Verwendung eines Extrusionswerkzeugs und anschließender Kalibrierung des erhaltenen Extrudates hergestellt. Mit einem angepassten Extrusionswerkzeug können nach diesem Verfahren die erfindungsgemäßen Sandwiches hergestellt werden.In addition, the internal coextrusion process is suitable for producing the sandwiches according to the invention. In EP1270176 a method for the production of multilayer hollow profile sheets is described. In this case, an upper and a lower layer of a plastic melt and a lying in the interior of the hollow chamber profile layer of a plastic melt by coextrusion of the plastic melt and using an extrusion die and subsequent calibration of the resulting extrudate is prepared. With an adapted extrusion tool, the sandwiches according to the invention can be produced by this process.

Teil der Erfindung sind somit auch das Kammergussverfahren und das Innen-Coextrusionsverfahren zur Herstellung der erfindungsgemäßen Sandwiches.part The invention thus also includes the chamber casting method and the internal coextrusion method for producing the sandwiches according to the invention.

Die Poymethylmethacrylat-Sandwiches mit phototropen Farbstoffen sind vielseitig verwendbar. Sie können beispielsweise für selbstabschattende Systeme im Baubereich, wie z.B. Gewächshäuser, Wintergärten, Verglasungen (z.B. Lichtkuppeln), Schaufenster verwendet werden.The Poymethylmethacrylat sandwiches with photochromic dyes are versatile. You can for example self-shading systems in the construction sector, e.g. Greenhouses, conservatories, glazings (e.g., domes), showcases.

Die im Folgenden gegebenen Beispiele werden zur besseren Veranschaulichung der vorliegenden Erfindung gegeben, sind jedoch nicht dazu geeignet, die Erfindung auf die hierin offenbarten Merkmale zu beschränken.The Examples given below are for better illustration of the present invention, but are not suitable to limit the invention to the features disclosed herein.

Beispiel 1example 1

Farbloses Acrylglas für Außenscheiben des SandwichsColorless Acrylic glass for outer panes of the sandwich

In 998 Teile präpolymeres Methylmethacrylat (Viskosität ca. 1000 cP) werden folgende Zusätze unter Rühren gelöst:
1 Teil 2,2'-Azobis-(2,4-dimethylvaleronitril)
1 Teil GlykoldimethacrylatIn 998 parts of prepolymeric methyl methacrylate (viscosity about 1000 cP), the following additives are dissolved with stirring:
1 part of 2,2'-azobis (2,4-dimethylvaleronitrile)
1 part glycol dimethacrylate

Optional können noch Lichtschutzmittel zugegeben werden, um die photochrome Innenschicht zu schützen.optional can light stabilizers may be added to the photochromic inner layer protect.

Geeignet sind dafür HALS-Produkte, wie Tinuvin 770 und UV-Absorber, die besonders im kurzwelligen UV-Bereich wirksam sind, z.B. Sanduvor VSU.Suitable are for it HALS products, such as Tinuvin 770 and UV absorbers, especially in the shortwave UV range, e.g. Sanduvor VSU.

Der Ansatz wird intensiv gerührt, in eine mit einer 3mm dicken Schnur distanzierten Silikatglaskammer im Format 400×500mm gefüllt und im Wasserbad 16h bei 45°C polymerisiert. Die Endpolymerisation erfolgt im Temperschrank 4h bei 115°C.Of the Approach is intensely stirred, into a silicate glass chamber which is distanced with a 3mm thick cord in the format 400 × 500mm filled and in a water bath for 16 h at 45 ° C polymerized. The final polymerization is carried out in a tempering 4h at 115 ° C.

Beispiel 2Example 2

Photochrome Innenschicht des Sandwichs:Photochromic inner layer of the sandwich:

In 9988 Teile Butylmethacrylat werden folgende Zusätze unter Rühren gelöst:
5 Teile 2,2'-Azobis-(isobutyronitril)
5 Teile 2,2'-Azobis-(2,4-dimethylvaleronitril)
1 Teil Reversacol Sunflower Bt 278/13 (photochrome Farbstoffe der Fa. James Robinson, England)
1 Teil Reversacol Palatinate Purple (photochrome Farbstoffe der Fa. James Robinson, England)In 9988 parts of butyl methacrylate, the following additives are dissolved with stirring:
5 parts of 2,2'-azobis (isobutyronitrile)
5 parts of 2,2'-azobis (2,4-dimethylvaleronitrile)
1 part Reversacol Sunflower Bt 278/13 (photochromic dyes from James Robinson, England)
1 part Reversacol Palatinate Purple (photochromic dyes from James Robinson, England)

Der Ansatz wird intensiv gerührt, in eine mit einer 3mm dicken Schnur distanzierten Kammer aus farblosem Acrylglas aus Versuch 1 gefüllt und im Wasserbad 22 h bei 50°C polymerisiert.Of the Approach is intensely stirred, in a chamber of colorless with a 3mm thick string distanced Acrylic glass from experiment 1 filled and in a water bath at 50 ° C for 22 h polymerized.

Es wird eine transparente, leicht gelbliche Platte mit der für Polymethacrylat typischen hohen mechanischen Festigkeit erhalten. Durch Belichtung mit Sonnenlicht wird die Platte je nach Lichtintensität nach ca. 30 Sekunden bis zu 2 Minuten farblich deutlich intensiver und nimmt eine graubraune bis braune Färbung an.It becomes a transparent, slightly yellowish plate with polymethacrylate typical high mechanical strength. By exposure with Sunlight, the plate, depending on the light intensity after approx. 30 seconds to 2 minutes in terms of color significantly more intense and takes a greyish brown to brown color at.

Claims (13)

Poymethylmethacrylat-Sandwiches, enthaltend zwei Polymethylmethacrylat-Platten und eine Zwischenschicht, die phototrope Farbstoffe enthält.Poymethyl methacrylate sandwiches containing two Polymethyl methacrylate sheets and an intermediate layer containing photochromic dyes. Poymethylmethacrylat-Sandwiches gemäß Anspruch 1, dadurch gekennzeichnet, dass die Zwischenschicht Polyacrylate oder alkylierte Polymethacrylate, bevorzugt Polybutylmethacrylate, enthält.Poymethylmethacrylat sandwiches according to claim 1, characterized in that the intermediate layer polyacrylates or alkylated polymethacrylates, preferably polybutyl methacrylates, contains. Poymethylmethacrylat-Sandwiches gemäß Anspruch 2, dadurch gekennzeichnet, dass die Zwischenschicht Comonomere enthält.Poymethylmethacrylat sandwiches according to claim 2, characterized in that the intermediate layer contains comonomers. Poymethylmethacrylat-Sandwich gemäß der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass die Zwischenschicht Weichmacher enthält.Poymethyl methacrylate sandwich according to claims 1 to 3, characterized the intermediate layer contains plasticizer. Poymethylmethacrylat-Sandwich gemäß der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass die Zwischenschicht Spiro-naphthoxazine oder Naphthopyrane enthält.Poymethyl methacrylate sandwich according to claims 1 to 4, characterized that the intermediate layer spiro-naphthoxazine or naphthopyrans contains. Poymethylmethacrylat-Sandwich gemäß der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass die Zwischenschicht eine Dicke von 0,01 bis 5 mm, bevorzugt von 0,1 bis 3 mm, hat.Poymethyl methacrylate sandwich according to claims 1 to 5, characterized the intermediate layer has a thickness of 0.01 to 5 mm, preferred from 0.1 to 3 mm. Poymethylmethacrylat-Sandwich gemäß Anspruch 6, dadurch gekennzeichnet, dass die Zwischenschicht phototrope Farbstoffe in Mengen zwischen 0,001 und 10% enthält.Poymethyl methacrylate sandwich according to claim 6, characterized that the intermediate layer contains photochromic dyes in quantities between Contains 0.001 and 10%. Poymethylmethacrylat-Sandwich gemäß Anspruch 1, dadurch gekennzeichnet, dass die Polymethylmethacrylat-Platten Lichtschutzmittel enthalten.Poymethyl methacrylate sandwich according to claim 1, characterized that the polymethyl methacrylate plates contain light stabilizers. Poymethylmethacrylat-Sandwich gemäß Anspruch 1, dadurch gekennzeichnet, dass die Polymethylmethacrylat-Platten Farbstoffe enthalten.Poymethyl methacrylate sandwich according to claim 1, characterized that the polymethyl methacrylate plates contain dyes. Poymethylmethacrylat-Sandwich gemäß Anspruch 1, dadurch gekennzeichnet, dass die Polymethylmethacrylat-Platten Comonomere, insbesondere Vernetzer, enthaltenPoymethyl methacrylate sandwich according to claim 1, characterized in that the polymethyl methacrylate plates Comonomers, in particular crosslinkers Verfahren zur Herstellung von Polymethylmethacrylat-Sandwiches gemäß Anspruch 1, dadurch gekennzeichnet, dass im Kammergußprozeß eine Zwischenschicht zwischen zwei Polymethacrylat-Platten gegossen und über einen Temperprozeß miteinander verbunden werden.Process for the preparation of polymethyl methacrylate sandwiches according to claim 1, characterized in that in the chamber casting process an intermediate layer between poured two polymethacrylate plates and a tempering process with each other get connected. Verfahren zur Herstellung von Polymethylmethacrylat-Sandwiches gemäß Anspruch 1, dadurch gekennzeichnet, dass durch Innen-Coextrusion zwei Polymethacrylat-Platten mit einer Zwischenschicht hergestellt werden.Process for the preparation of polymethyl methacrylate sandwiches according to claim 1, characterized in that by internal coextrusion two polymethacrylate plates be made with an intermediate layer. Verwendung von Polymethylmethacrylat-Sandwiches im Baubereich.Use of polymethyl methacrylate sandwiches in the construction sector.
DE102004053817A 2004-11-04 2004-11-04 Acrylic glass with photochromic properties Withdrawn DE102004053817A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE102004053817A DE102004053817A1 (en) 2004-11-04 2004-11-04 Acrylic glass with photochromic properties
PCT/EP2005/010556 WO2006048089A1 (en) 2004-11-04 2005-09-30 Acrylic glass having photochromic properties
KR1020077010075A KR20070074597A (en) 2004-11-04 2005-09-30 Acrylic glass with photochromic properties
EP05791361A EP1807261A1 (en) 2004-11-04 2005-09-30 Acrylic glass having photochromic properties
CNA2005800314417A CN101022950A (en) 2004-11-04 2005-09-30 Acrylic glass having photochromic properties
CA002580765A CA2580765A1 (en) 2004-11-04 2005-09-30 Acrylic glass having photochromic properties
AU2005300858A AU2005300858A1 (en) 2004-11-04 2005-09-30 Acrylic glass having photochromic properties
BRPI0517270-5A BRPI0517270A (en) 2004-11-04 2005-09-30 acrylic glass with photochromic properties
JP2007539479A JP2008518809A (en) 2004-11-04 2005-09-30 Acrylic glass with photoreversible discoloration characteristics
ZA200703580A ZA200703580B (en) 2004-11-04 2007-05-03 Acrylic glass having photochromic properties

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Application Number Priority Date Filing Date Title
DE102004053817A DE102004053817A1 (en) 2004-11-04 2004-11-04 Acrylic glass with photochromic properties

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DE102004053817A1 true DE102004053817A1 (en) 2006-05-11

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Publication number Priority date Publication date Assignee Title
US7704586B2 (en) 2005-03-09 2010-04-27 Degussa Ag Plastic molded bodies having two-dimensional and three-dimensional image structures produced through laser subsurface engraving
DE102007021199B4 (en) 2006-07-17 2016-02-11 Evonik Degussa Gmbh Compositions of organic polymer as matrix and inorganic particles as filler, process for their preparation and their use and moldings produced therewith
CN103481564B (en) * 2013-08-16 2016-04-13 武汉羿阳科技有限公司 A kind of fenestrated membrane of automatic adjustment light transmittance
CN110818936B (en) * 2019-11-14 2022-04-05 陕西理工大学 A kind of organic glass and its preparation method and application

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6424740A (en) * 1987-07-20 1989-01-26 Toyota Motor Corp Light-shield glass for windshield of automobile
JPH05187175A (en) * 1992-01-10 1993-07-27 Hashimoto Forming Ind Co Ltd Scattered light window and manufacturing method
EP1162482A2 (en) * 2000-06-09 2001-12-12 Mitsubishi Gas Chemical Company, Inc. Synthetic resin laminate having both polarization characteristic and photochromism characteristic
US6446402B1 (en) * 1998-10-15 2002-09-10 Pleotint, L.L.C. Thermochromic devices
EP1270176A1 (en) * 2001-06-22 2003-01-02 Röhm GmbH & Co. KG Exstrusion die for manufacturing sheets from thermoplastic material with internal hollow chambers having an inner coextruded layer
US6547390B1 (en) * 2000-09-11 2003-04-15 Exxene Corporation Top stabilized photochromic lens system
US20040131872A1 (en) * 2001-11-29 2004-07-08 Shaobin Fan Photochromic articles and methods for making them

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE7316334U (en) * 1973-04-30 1973-08-23 Jenaer Glaswerk Schott & Gen TRANSLUCENT PHOTOTROPIC COMPOSITE BODY
JPH06138577A (en) * 1992-09-08 1994-05-20 Mitsubishi Kasei Corp Photochromic laminate

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6424740A (en) * 1987-07-20 1989-01-26 Toyota Motor Corp Light-shield glass for windshield of automobile
JPH05187175A (en) * 1992-01-10 1993-07-27 Hashimoto Forming Ind Co Ltd Scattered light window and manufacturing method
US6446402B1 (en) * 1998-10-15 2002-09-10 Pleotint, L.L.C. Thermochromic devices
EP1162482A2 (en) * 2000-06-09 2001-12-12 Mitsubishi Gas Chemical Company, Inc. Synthetic resin laminate having both polarization characteristic and photochromism characteristic
US6547390B1 (en) * 2000-09-11 2003-04-15 Exxene Corporation Top stabilized photochromic lens system
EP1270176A1 (en) * 2001-06-22 2003-01-02 Röhm GmbH & Co. KG Exstrusion die for manufacturing sheets from thermoplastic material with internal hollow chambers having an inner coextruded layer
US20040131872A1 (en) * 2001-11-29 2004-07-08 Shaobin Fan Photochromic articles and methods for making them

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ZA200703580B (en) 2008-08-27
CA2580765A1 (en) 2006-05-11
BRPI0517270A (en) 2008-10-07
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KR20070074597A (en) 2007-07-12
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