DE102011117270A1 - Preparing an optical filter whose highly concentrated optical effective additives are used as a mixture, where a compound contains anthracene, thiophene, 2-methyl-but-2-enoic acid methyl ester, and 1H-benzotriazole - Google Patents

Preparing an optical filter whose highly concentrated optical effective additives are used as a mixture, where a compound contains anthracene, thiophene, 2-methyl-but-2-enoic acid methyl ester, and 1H-benzotriazole Download PDF

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DE102011117270A1
DE102011117270A1 DE102011117270A DE102011117270A DE102011117270A1 DE 102011117270 A1 DE102011117270 A1 DE 102011117270A1 DE 102011117270 A DE102011117270 A DE 102011117270A DE 102011117270 A DE102011117270 A DE 102011117270A DE 102011117270 A1 DE102011117270 A1 DE 102011117270A1
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Karin Rauch
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SE MA GES fur INNOVATIONEN MBH
Se Ma Gesellschaft fur Innovationen Mbh
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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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
    • B32B17/10036—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising two outer glass sheets
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10165—Functional features of the laminated safety glass or glazing
    • B32B17/10431—Specific parts for the modulation of light incorporated into the laminated safety glass or glazing
    • B32B17/1044—Invariable transmission
    • B32B17/10449—Wavelength selective transmission
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10678—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer comprising UV absorbers or stabilizers, e.g. antioxidants
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10788—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing ethylene vinylacetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D131/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Coating compositions based on derivatives of such polymers
    • C09D131/02—Homopolymers or copolymers of esters of monocarboxylic acids
    • C09D131/04—Homopolymers or copolymers of vinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/10—Homopolymers or copolymers of methacrylic acid esters
    • C09D133/12—Homopolymers or copolymers of methyl methacrylate
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Abstract

The method of preparing an optical filter whose highly concentrated optical effective additives are used as a mixture, is claimed, where a compound contains anthracene, thiophene, (Z)-2-methyl-but-2-enoic acid methyl ester, and 1H-benzotriazole. A component of a layer is processed on a fusion film and/or polyvinyl butyral, ethylene-vinyl acetate or another thermoplastic elastomer such as thermoplastic polyurethane or is processed by an additive of a polymer such as cellulose triacetates or polymethyl methacrylate to convert a thin polymer film. The method of preparing an optical filter whose highly concentrated optical effective additives are used as a mixture, is claimed, where a compound contains anthracene, thiophene, (Z)-2-methyl-but-2-enoic acid methyl ester, and 1H-benzotriazole. A component of a layer is processed on a fusion film and/or polyvinyl butyral, ethylene-vinyl acetate or another thermoplastic elastomer such as thermoplastic polyurethane or is processed by an additive of a polymer such as cellulose triacetates or polymethyl methacrylate to convert a thin polymer film, which is a part of a composite material, where the resulted filter has a layer. The optically effective additives contain a radical scavenger, a plasticizer, a near infrared absorber and a dye. A coating is processed to form the compound, and contains the radical scavenger. The compound is composed of glass or polymer disc. The optical filter: has a transmission of 25 nm that increases from 0-75%, and an absorption edge of 405-430 nm; and remains stable in a standardized accelerated UV-test over 4000 hours.

Description

Die vorliegende Erfindung betrifft ein UV-Filter, das zum Schutz empfindlicher Materialien als Folie oder als Verbund verschiedener Schichten eingesetzt werden kann.The present invention relates to a UV filter which can be used to protect sensitive materials as a film or as a composite of different layers.

Es besteht im Wesentlichen aus einem blau emittierenden Fluoreszenzfarbstoff und einem UV-Absorber, wobei eine grundlegende Voraussetzung das Vorliegen einer homogenen Mischung dieser beiden Bestandteile in einer Beschichtungslösung ist.It consists essentially of a blue-emitting fluorescent dye and a UV absorber, a basic prerequisite being the presence of a homogeneous mixture of these two constituents in a coating solution.

Diese schichtbildende Lösung kann als weitere Bestandteile ein Polymer wie PVB, CTA oder PMMA, einen Stabilisator wie Vebindung 53 und NIR-Absorber wie Ni(bdt)2-Komplexe enthalten.This layer-forming solution may contain, as further constituents, a polymer such as PVB, CTA or PMMA, a stabilizer such as compound 53 and NIR absorbers such as Ni (bdt) 2 complexes.

Es ist bereits Stand der Technik, diese Verbindungen einzeln oder in verschiedenen Gemischen Kunststoffen zuzusetzen, um die Alterungsbeständigkeit der Polymere zu erhöhen oder den UV-Schutz dieser Materialien zu nutzen. Die optischen Eigenschaften werden hierbei in der Weise realisiert, daß die kurzwellig absorbierenden Additive in den Kleber oder das Substrat schon bei der Herstellung eingearbeitet werden müssen, wie es z. b. in der Patentschrift US 20070160832 A1 dargestellt wird. Diese Vorgehensweise wurde vorher schon in EP 0635538 A2 auch zur Herstellung von PVB-Folien beschrieben, aber das allgemeine Konzept, durch die Kombination eines normalen UV-Absorbers mit einem lumineszenten Farbstoff Fasern zu schützen, ist bereits seit 1986 bekannt ( DE 3614377 C2 ).It is already state of the art to add these compounds to plastics individually or in different mixtures in order to increase the aging resistance of the polymers or to use the UV protection of these materials. The optical properties are in this case realized in such a way that the short-wave absorbing additives in the adhesive or the substrate must be incorporated during the preparation, as for example in the patent US 20070160832 A1 is pictured. This procedure was already in EP 0635538 A2 also been described for the production of PVB films, but the general concept of protecting fibers by the combination of a normal UV absorber with a luminescent dye has been known since 1986 ( DE 3614377 C2 ).

Unsere Problemstellung besonders dünne optische Filter herzustellen, erforderte es, die kurzwellig absorbierenden Additive in hohen Konzentrationen einzusetzen.Our problem to produce particularly thin optical filters, it was necessary to use the short-wavelength absorbing additives in high concentrations.

Versucht man aber, die handelsüblichen Substanzen 02, 08, 47 und sogar, die von uns produzierten eigentlich besonders leichtlöslichen UV-Absorber 23 und 27 in eine Polymermatrix einzubringen, scheitert dies an der unzureichenden Löslichkeit in den gebräuchlichen Lösungsmitteln.However, if one attempts to incorporate the commercially available substances 02, 08, 47 and even the UV-absorbers 23 and 27, which are actually produced particularly readily, into a polymer matrix, this fails due to the insufficient solubility in the conventional solvents.

Überraschend wurde dabei gefunden, daß dies dennoch gelingt, wenn man ein Gemisch der verschiedenen Additive einsetzt und daraus hochkonzentrierte Lösungen herstellt. Auf diese Weise unterdrücken die Bestandteile wechselseitig ihre Kristallisation und ermöglichen sogar die Beschichtung ohne den Zusatz weiterer Bindemittel oder Weichmacher. Man kann dies zur Modifizierung von PVB- oder EVA-Folien nutzen und gewinnt auf diesem Wege ein hohes Maß an Flexibilität, was insbesondere zur Herstellung kleinerer Mengen Schutzfolie unabdingbar ist. Es erübrigt sich, durch diese verbesserte Herstellungsmethode erst durch Extrusion eine spezielle Folie zu produzieren, sondern ermöglicht den Einsatz einer handelsüblichen Folie.Surprisingly, it has been found that this still succeeds when using a mixture of the various additives and produces highly concentrated solutions. In this way, the components mutually suppress their crystallization and even allow the coating without the addition of other binders or plasticizers. This can be used for the modification of PVB or EVA films and thus gains a high degree of flexibility, which is indispensable, in particular, for the production of relatively small amounts of protective film. It is unnecessary to produce a special film by extrusion through this improved production method, but allows the use of a commercially available film.

Eine weitere Anwendung ergab sich darin, daß die unterdrückte Kristallisation auch die Herstellung von Polymerfolien ermöglicht, die nur eine Schichtdicke von 20 bis 100 μm aufweisen, dabei aber einen UV-Schutz bis über 410 nm erzielen und dennoch für den Betrachter nicht als gelb gefärbt erscheinen. Diese Folien zeichnen sich durch eine beispiellos hohe Transparenz im sichtbaren Spektralgebiet aus, und sind deshalb für optische Filter, die maximalen UV-Schutz gewährleisten sollen, besonders interessant. Wenn man die Schichtdicke vergrößert, kann man extrem steile Absorptionskannten bis 430 nm realisieren.Another application was that the suppressed crystallization also allows the production of polymer films which have only a layer thickness of 20 to 100 microns, but achieve UV protection to over 410 nm and yet do not appear to the viewer as yellow colored , These films are characterized by an unprecedentedly high transparency in the visible spectral region, and are therefore of particular interest for optical filters which are intended to ensure maximum UV protection. If you increase the layer thickness, you can realize extremely steep Absorptionskannten to 430 nm.

Diese geringe Schichtdicke stellt auch einen entscheidenden Vorteil bei der Herstellung von Verbundmaterialien (Laminate) mit besonderer mechanischer Festigkeit dar. Man kann so eine dünne Folie in ein mehrschichtiges Sicherheitsglas einarbeiten und erhöht gleichzeitig die mechanische Stabilität und den UV-Schutz, wobei trotzdem geringe Schichtdicken und hervorragende optische Eigenschaften realisierbar sind. Besonders wichtig sind diese Aspekte bei der Herstellung gewölbter Sicherheitsgläser.This small layer thickness also represents a decisive advantage in the production of composite materials (laminates) with particular mechanical strength. It is thus possible to incorporate a thin film into a multi-layered safety glass and at the same time increases the mechanical stability and the UV protection, nevertheless low layer thicknesses and excellent optical properties can be realized. These aspects are particularly important in the production of curved safety glass.

Wir haben verschiedene Kombinationen gefunden, welche diese guten optischen Eigenschaften selbst im standardisierten akzelerierten UV-Test ( IEC 60904-9; 295 – 3.000 nm und 1000 W/m2 ) über 4000 h hinaus bewahren.We have found various combinations which show these good optical properties even in the standardized accelerated UV test ( IEC 60904-9; 295-3000 nm and 1000 W / m2 ) beyond 4000 h.

Zusammengefaßt ergeben sich folgende Vorteile gegenüber dem Stand der Technik:

  • 1. höhere Flexibilität durch das Beschichtungsverfahren
  • 2. sehr geringe Schichtdicken der optisch wirksamen Beschichtung
  • 3. höhere Steilheit der Absorptionskante gegenüber Vergleichsprodukten
  • 4. optimale Annäherung der Absorptionskante bis an die Sichtbarkeitsgrenze
  • 5. höhere Lichtstabilität als Vergleichsprodukte
    Figure 00020001
In summary, there are the following advantages over the prior art:
  • 1. higher flexibility through the coating process
  • 2. very low layer thicknesses of the optically active coating
  • 3. higher slope of the absorption edge compared to comparative products
  • 4. optimal approach of the absorption edge up to the visibility limit
  • 5. higher light stability than comparison products
    Figure 00020001

Die Erfindung bezieht sich auf den Einsatz von Materialien der allgemeinen Formel 1.The invention relates to the use of materials of general formula 1.

Typische Beispiele für Materialgemische nach der allgemeinen Formel 1 sind: Gemisch Komponente OB Komponente UA I 02 23 II 08 23 III 02 47 IV 08 47 V 02 27 VI 11 27 VII 19 27 Typical examples of material mixtures according to the general formula 1 are: mixture Component OB Component UA I 02 23 II 08 23 III 02 47 IV 08 47 V 02 27 VI 11 27 VII 19 27

Zur weiteren Erhöhung der Lichtstabilität können Additive vom Typ der Verbindung 53 verwendet werden. Diese hohe langanhaltende Stabilisierung wirkte sich auch auf NIR-Absorber wie Ni(bdt)2-Komplexe aus, die aufgrund der bekannten schnellen Photodegradation zunehmend durch das Aufsputtern dünner anorganischer Reflexionsschichten verdrängt werden, was für spezielle Anwendungen aber häufig unwirtschaftlich ist.To further increase the light stability, additives of the compound 53 type can be used. This high sustained stabilization also affected NIR absorbers such as Ni (bdt) 2 complexes, which are increasingly displaced by the sputtering of thin inorganic reflective layers due to the known rapid photodegradation, which is often uneconomical for specific applications.

Die folgenden Beispiele der eingesetzten Materialien dienen der Erläuterung der vorliegenden Erfindung, sollen diese jedoch in keiner Weise einschränken:

Figure 00030001
Tabelle 1 (Die Tabellen 1–3 definieren die Substituenten der in den Tabellen 4 aufgeführten Beispiele für die Komponenten OB und UA)
Figure 00030002
Tabelle 2 (Substituenten X, Y und Z) Substituent X Id-Nr. Substituent Y Id-Nr. Substituent Z ID-Nr. CH IDXYZ01 -CH=CH-CH= IDXYZ02 CH IDXYZ03 O IDXYZ04 o-Phenylen IDXYZ05 N IDXYZ06 OB IDXYZ07 - IDXYZ08 O IDXYZ09 C-OH IDXYZ10 -CMe=CH-Ctert-Bu= IDXYZ11 CH IDXYZ12 -Ctert-Bu=CH-Ctert-Bu= IDXYZ13 -Ctert-Octyl=CH-CH= IDXYZ14
Figure 00040001
Tabelle 3 (Substituenten B und Ar)
Figure 00040002
Tabelle 4/I (Id-Nr.-Verknüpfung) IDG01 X Y Z B Ar 02 IDXYZ01 IDXYZ02 IDXYZ03 - - Tabelle 4/II (Id-Nr.-Verknüpfung) IDG02 X Y Z B Ar 03 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr01 - 04 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr03 - 05 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr05 - 06 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr09 - Tabelle 4/III (Id-Nr.-Verknüpfung) IDG03 X Y Z B Ar 07 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr01 - 08 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr03 - 09 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr05 - 10 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr09 - Tabelle 4/IV (Id-Nr.-Verknüpfung) IDG04 X Y Z B Ar 11 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr01 - 12 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr03 - 13 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr05 - 14 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr09 - Tabelle 4/V (Id-Nr.-Verknüpfung) IDG05 X Y Z B Ar 15 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr01 - 16 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr03 - 17 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr05 - 18 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr09 - Tabelle 4/VI (Id-Nr.-Verknüpfung) IDG06 X Y Z B Ar 19 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr01 - 20 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr03 - 21 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr05 - 22 IDXYZ04 IDXYZ05 IDXYZ06 IDBAr09 - Tabelle 4/VII (Id-Nr.-Verknüpfung) IDG07 X Y Z B Ar 23 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr02 24 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr04 25 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr06 26 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr08 27 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr02 28 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr04 29 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr06 30 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr08 Tabelle 4/VIII (Id-Nr.-Verknüpfung) IDG08 X Y Z B Ar 31 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr02 32 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr04 33 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr06 34 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr08 35 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr02 36 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr04 37 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr06 38 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr08 Tabelle 4/IX (Id-Nr.-Verknüpfung) IDG09 X Y Z B Ar 39 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr02 40 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr04 41 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr06 42 IDXYZ07 - IDXYZ09 IDBAr05 IDBAr08 43 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr02 44 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr04 45 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr06 46 IDXYZ07 - IDXYZ09 IDBAr07 IDBAr08 Tabelle 4/X (Id-Nr.-Verknüpfung) IDG10 X Y Z B Ar 47 IDXYZ10 IDXYZ11 IDXYZ12 - - 48 IDXYZ10 IDXYZ13 IDXYZ12 - - 49 IDXYZ10 IDXYZ14 IDXYZ12 - - Tabelle 4/XI (Id-Nr.-Verknüpfung) IDG11 X Y Z B Ar 50 IDXYZ10 IDXYZ11 IDXYZ12 - - 51 IDXYZ10 IDXYZ13 IDXYZ12 - - 52 IDXYZ10 IDXYZ14 IDXYZ12 - - Tabelle 4/IX (Id-Nr.-Verknüpfung) IDG12 X Y Z B Ar 53 IDXYZ07 - IDXYZ09 IDBar11 IDBar10 The following examples of the materials used are illustrative of the present invention, but are not intended to limit it in any way:
Figure 00030001
Table 1 (Tables 1-3 define the substituents of the examples of components OB and UA listed in Tables 4)
Figure 00030002
Table 2 (Substituents X, Y and Z) Substituent X Id no. Substituent Y Id no. Substituent Z ID no. CH ID XYZ 01 -CH = CH-CH = ID XYZ 02 CH ID XYZ 03 O ID XYZ 04 o-phenylene ID XYZ 05 N ID XYZ 06 IF ID XYZ 07 - ID XYZ 08 O ID XYZ 09 C-OH ID XYZ 10 -CMe = CH-Ctert-Bu = ID XYZ 11 CH ID XYZ 12 -Ctert-Bu = CH-Ctert-Bu = ID XYZ 13 -Ctert-octyl = CH-CH = ID XYZ 14
Figure 00040001
Table 3 (Substituents B and Ar)
Figure 00040002
Table 4 / I (ID No. Link) ID G 01 X Y Z B Ar 02 ID XYZ 01 ID XYZ 02 ID XYZ 03 - - Table 4 / II (ID No. Link) ID G 02 X Y Z B Ar 03 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 01 - 04 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 03 - 05 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 05 - 06 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 09 - Table 4 / III (ID No. Link) ID G 03 X Y Z B Ar 07 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 01 - 08 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 03 - 09 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 05 - 10 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 09 - Table 4 / IV (ID No. Link) ID G 04 X Y Z B Ar 11 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 01 - 12 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 03 - 13 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 05 - 14 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 09 - Table 4 / V (ID No. Link) ID G 05 X Y Z B Ar 15 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 01 - 16 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 03 - 17 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 05 - 18 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 09 - Table 4 / VI (ID No. Link) ID G 06 X Y Z B Ar 19 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 01 - 20 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 03 - 21 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 05 - 22 ID XYZ 04 ID XYZ 05 ID XYZ 06 ID BAr 09 - Table 4 / VII (ID No. Link) ID G 07 X Y Z B Ar 23 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 02 24 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 04 25 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 06 26 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 08 27 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 02 28 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 04 29 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 06 30 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 08 Table 4 / VIII (ID No. Link) ID G 08 X Y Z B Ar 31 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 02 32 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 04 33 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 06 34 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 08 35 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 02 36 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 04 37 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 06 38 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 08 Table 4 / IX (ID No. Link) ID G 09 X Y Z B Ar 39 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 02 40 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 04 41 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 06 42 ID XYZ 07 - ID XYZ 09 ID BAr 05 ID BAr 08 43 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 02 44 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 04 45 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 06 46 ID XYZ 07 - ID XYZ 09 ID BAr 07 ID BAr 08 Table 4 / X (ID No. Link) ID G 10 X Y Z B Ar 47 ID XYZ 10 ID XYZ 11 ID XYZ 12 - - 48 ID XYZ 10 ID XYZ 13 ID XYZ 12 - - 49 ID XYZ 10 ID XYZ 14 ID XYZ 12 - - Table 4 / XI (ID No. Link) ID G 11 X Y Z B Ar 50 ID XYZ 10 ID XYZ 11 ID XYZ 12 - - 51 ID XYZ 10 ID XYZ 13 ID XYZ 12 - - 52 ID XYZ 10 ID XYZ 14 ID XYZ 12 - - Table 4 / IX (ID No. Link) ID G 12 X Y Z B Ar 53 ID XYZ 07 - ID XYZ 09 ID Bar 11 ID Bar 10

BeispieleExamples

Beispiel 1: (Substanzkombination 08/47)Example 1: (substance combination 08/47)

Lösung I:Solution I:

2,4 g der Substanz 08, 4 g der Verbindung 47 sowie 4 g 53 werden miteinander verrieben und in einem Gemisch aus 145 ml Methylenchlorid und 15 ml Methanol gelöst.2.4 g of substance 08, 4 g of compound 47 and 4 g of 53 are triturated together and dissolved in a mixture of 145 ml of methylene chloride and 15 ml of methanol.

Lösung II:Solution II:

Es wird eine Polymerlösung, bestehend aus 36 g Cellulosetriacetat, 3,6 g eines Weichmachers Triphenylphosphat und eines Lösungsmittelgemisches aus 26,4 g Methanol und 237,6 g Dichlormethan hergestellt.A polymer solution consisting of 36 g of cellulose triacetate, 3.6 g of a plasticizer triphenyl phosphate and a solvent mixture of 26.4 g of methanol and 237.6 g of dichloromethane is prepared.

Es werden 75,9 g von der Lösung I mit 303,6 g der Lösung II in einem Behälter gegeben und bei einer Temperatur von 5°–7°C unter ständigem Bewegen gleichmäßig vermischt und im Anschluss eine 100 μm starke CTA-Folie hergestellt, die bei 400 nm 0%, bei 405 nm 0,3%, bei 410 nm 0,6%, bei 415 nm 5,6% und bei 420 nm 30% Transmission und eine Dichte von 1,33 g/cm3 aufweist.There are added 75.9 g of the solution I with 303.6 g of the solution II in a container and uniformly mixed at a temperature of 5 ° -7 ° C with constant stirring and then made a 100 micron thick CTA film, 0% at 400 nm, 0.3% at 405 nm, 0.6% at 410 nm, 5.6% at 415 nm and 30% transmission at 420 nm and a density of 1.33 g / cm 3 .

Beispiel 2: (Substanzkombination 02/23)Example 2: (substance combination 02/23)

8,4 g der Verbindung 02, 12 g der Verbindung 23 und 12 g der Verbindung 53 werden miteinander vermengt und in einem Gemisch aus 360 ml Methylethylketon und 120 ml Tetrahydrofuran gelöst. Mit dieser Lösung werden ca. 10 m2 EVA-Folie beschichtet. Nach dem Trocknen und Laminieren zwischen Glas wird ein transparenter Verbund ohne Gelbtönung erhalten8.4 g of the compound O 2, 12 g of the compound 23 and 12 g of the compound 53 are mixed together and dissolved in a mixture of 360 ml of methyl ethyl ketone and 120 ml of tetrahydrofuran. About 10 m 2 of EVA film are coated with this solution. After drying and lamination between glass, a transparent composite is obtained without yellowing

Beispiel 3: (Substanzkombination 02/47) Example 3: (Substance combination 02/47)

7 g der Verbindung 02, 10 g der Verbindung 47 und 10 g der Verbindung 53 werden miteinander vermengt und in einem Gemisch aus 300 ml Methylethylketon und 100 ml Tetrahydrofuran gelöst. Mit dieser Lösung werden ca. 8 m2 PVP-Folie beschichtet. Nach dem Trocknen und Laminieren zwischen Glas wird ein transparenter Verbund ohne Gelbtönung erhalten ( )7 g of the compound O 2, 10 g of the compound 47 and 10 g of the compound 53 are mixed together and dissolved in a mixture of 300 ml of methyl ethyl ketone and 100 ml of tetrahydrofuran. Approx. 8 m 2 PVP film is coated with this solution. After drying and lamination between glass, a transparent composite without yellowing is obtained ( )

ZITATE ENTHALTEN IN DER BESCHREIBUNG QUOTES INCLUDE IN THE DESCRIPTION

Diese Liste der vom Anmelder aufgeführten Dokumente wurde automatisiert erzeugt und ist ausschließlich zur besseren Information des Lesers aufgenommen. Die Liste ist nicht Bestandteil der deutschen Patent- bzw. Gebrauchsmusteranmeldung. Das DPMA übernimmt keinerlei Haftung für etwaige Fehler oder Auslassungen.This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Zitierte PatentliteraturCited patent literature

  • US 20070160832 A1 [0004] US 20070160832 A1 [0004]
  • EP 0635538 A2 [0004] EP 0635538 A2 [0004]
  • DE 3614377 C2 [0004] DE 3614377 C2 [0004]

Zitierte Nicht-PatentliteraturCited non-patent literature

  • IEC 60904-9; 295 – 3.000 nm und 1000 W/m2 [0010] IEC 60904-9; 295-3000 nm and 1000 W / m2 [0010]

Claims (11)

Beansprucht wird ein Verfahren zur Herstellung optischer Filter deren optisch wirksame Additive als Gemisch eingesetzt werden, wobei mindestens jeweils eine Verbindung vom Typ 4/I bis 4/VI und gleichzeitig vom Typ 4/VII bis Typ 4/XI enthalten sein muß und diese Bestandteil einer Schicht auf einer Schmelzfolie wie Polyvinylbutyral, Ethylenvinylacetat oder einem anderen themoplastische Elastomer wie TPU ist oder durch Zusatz eines Polymers wie Cellulosetriacetat oder Polymethylmethacrylat selbst zu einer sehr dünnen Polymerfolie verarbeitet werden kann, die ihrerseits Bestandteil eines Verbundmaterials sein kann und der resultierende Filter letztlich eine Schicht enthält, die weiterhin dadurch gekennzeichnet ist, daß die optisch wirksamen Additive hochkonzentriert vorliegen, und sie gegebenenfalls einen Radikalfänger, einen Weichmacher, einen NIR-Absorber und einen Farbstoff enthalten kann.Claimed is a process for the preparation of optical filters whose optically active additives are used as a mixture, wherein at least one compound of type 4 / I to 4 / VI and at the same time of type 4 / VII to type 4 / XI must be included and this component of a Layer on a melt film such as polyvinyl butyral, ethylene vinyl acetate or other thermoplastic elastomer such as TPU or by adding a polymer such as cellulose triacetate or polymethyl methacrylate itself can be processed into a very thin polymer film, which in turn may be part of a composite material and the resulting filter ultimately contains a layer , which is further characterized in that the optically active additives are highly concentrated, and may optionally contain a radical scavenger, a plasticizer, an NIR absorber and a dye. Ein Verfahren nach Anspruch 1, wobei die Beschichtung auf Polyvinylbutyral oder Ethylenvinylacetat vorgenommen wird, daß zu einem Verbund verarbeitet wird, der aus zwei oder mehreren Glas- oder Polymerscheiben aufgebaut ist und die Beschichtung einen Radikalfänger enthält.A method according to claim 1, wherein the coating is carried out on polyvinyl butyral or ethylene vinyl acetate, which is processed into a composite composed of two or more glass or polymer discs and the coating contains a radical scavenger. Ein Verfahren nach Anspruch 2, wobei die optisch wirksamen Additive als Gemisch eingesetzt werden, wobei mindestens jeweils eine Verbindung vom Typ 4/I und 4/III und gleichzeitig vom Typ 4/VIII bis Typ 4/XI enthalten sein muß.A method according to claim 2, wherein the optically active additives are used as a mixture, wherein at least one compound of type 4 / I and 4 / III and at the same time of type 4 / VIII to type 4 / XI must be included. Ein Verfahren nach Anspruch 3, wobei die optisch wirksamen Additive als Gemisch eingesetzt werden, wobei mindestens jeweils eine Verbindung vom Typ 4/I und 4/III und gleichzeitig vom Typ 4/X bis Typ 4/XI enthalten sein muß.A method according to claim 3, wherein the optically active additives are used as a mixture, wherein at least one compound of type 4 / I and 4 / III and at the same time of the type 4 / X to type 4 / XI must be contained. Ein Verfahren nach Anspruch 4, wobei die optisch wirksamen Additive als Gemisch eingesetzt werden, wobei Verbindung 08 und gleichzeitig Verbindung 47 und 53 enthalten ist.A method according to claim 4, wherein the optically active additives are used as a mixture, wherein compound 08 and simultaneously compound 47 and 53 is included. Ein Verfahren nach Anspruch 1, wobei eine sehr dünne Polymerfolie erhalten wird, die ihrerseits Bestandteil eines Verbundmaterials sein kann und der resultierende Filter letztlich eine Schicht enthält, die weiterhin dadurch gekennzeichnet ist, daß sie einen Radikalfänger und einen Weichmacher enthält.A method according to claim 1, wherein a very thin polymer film is obtained, which in turn may be part of a composite material and the resulting filter ultimately comprises a layer further characterized by containing a radical scavenger and a plasticizer. Ein Verfahren nach Anspruch 6, wobei die optisch wirksamen Additive als Gemisch eingesetzt werden, wobei mindestens jeweils eine Verbindung vom Typ 4/I und 4/III und gleichzeitig vom Typ 4/VIII bis Typ 4/XI enthalten sein muß.A method according to claim 6, wherein the optically active additives are used as a mixture, wherein at least one compound of type 4 / I and 4 / III and at the same time of the type 4 / VIII to type 4 / XI must be contained. Ein Verfahren nach Anspruch 7, wobei das Basispolymer der Folie aus Celluloseacetat oder Polymethylmethacrylat besteht.A method according to claim 7 wherein the base polymer of the film is cellulose acetate or polymethylmethacrylate. Ein Verfahren nach Anspruch 8, wobei die optisch wirksamen Additive als Gemisch eingesetzt werden, wobei Verbindung 08 und gleichzeitig Verbindung 47, 53 und ein Weichmacher enthalten ist.A method according to claim 8, wherein the optically active additives are used as a mixture, wherein compound 08 and simultaneously compound 47, 53 and a plasticizer is included. Ein Verfahren nach Anspruch 1, daß einen optischen Filter liefert dessen Transmission über einen Bereich von 25 nm von 0% auf über 75% anwächst und im standardisierten akzelerierten UV-Test über 4000 h stabil bleibt.A method according to claim 1, which provides an optical filter whose transmission increases from 0% to over 75% over a range of 25 nm and remains stable for 4,000 hours in the standardized accelerated UV test. Ein Verfahren nach Anspruch 10, daß einen optischen Filter liefert dessen Absorptionskante zwischen 405 und 430 nm liegt.A method according to claim 10, which provides an optical filter whose absorption edge is between 405 and 430 nm.
DE102011117270A 2011-10-31 2011-10-31 Preparing an optical filter whose highly concentrated optical effective additives are used as a mixture, where a compound contains anthracene, thiophene, 2-methyl-but-2-enoic acid methyl ester, and 1H-benzotriazole Withdrawn DE102011117270A1 (en)

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DE3614377C2 (en) 1985-05-08 1994-05-19 Sandoz Ag Process for quenching fluorescence from optical brighteners
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US20070160832A1 (en) 2005-07-22 2007-07-12 General Binding Corporation Laminate film having optical brightener
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DE3614377C2 (en) 1985-05-08 1994-05-19 Sandoz Ag Process for quenching fluorescence from optical brighteners
EP0635538A2 (en) 1993-07-19 1995-01-25 Hoechst Aktiengesellschaft Polyvinyl butyral sheets with improved optical properties
US20070160832A1 (en) 2005-07-22 2007-07-12 General Binding Corporation Laminate film having optical brightener
EP1916097A2 (en) * 2006-10-24 2008-04-30 MGC Filsheet Co., Ltd. A non-glaring laminated body, a coated non-glaring laminated body, a non-glaring material, and a method for producing the non-glaring material

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