DE102005042097A1 - Flame-resistant epoxy resin is structured by a condensation at the oxiran rings to form phosphor-carbon compounds - Google Patents

Flame-resistant epoxy resin is structured by a condensation at the oxiran rings to form phosphor-carbon compounds Download PDF

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Publication number
DE102005042097A1
DE102005042097A1 DE200510042097 DE102005042097A DE102005042097A1 DE 102005042097 A1 DE102005042097 A1 DE 102005042097A1 DE 200510042097 DE200510042097 DE 200510042097 DE 102005042097 A DE102005042097 A DE 102005042097A DE 102005042097 A1 DE102005042097 A1 DE 102005042097A1
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Prior art keywords
epoxy resin
flame
dopo
phosphorus
cured
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DE200510042097
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German (de)
Inventor
Holger Dr. Keller
Berthold Dr. Just
Manfred Prof. Dr. Döring
Sebastian Seibold
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Schill and Seilacher Struktol AG
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Schill and Seilacher Struktol AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/14—Macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5033—Amines aromatic
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/18—Fireproof paints including high temperature resistant paints
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'

Abstract

The flame-resistant epoxy resin, in at least a partially cross-linked form, has structured units through direct condensation of 9.10-dihydro-9-oxa-phosphaphenanthrene-10-oxide (DOPO) at the oxiran rings of the epoxy resin to form phosphor-carbon compounds. There is a phosphor content of at least 1 wt.% with a glass-transition temperature of at least 110[deg]C. An added hardener is of diethylene toluoldiamine (DETDA).

Description

Die Erfindung betrifft ein flammfestes Epoxidharz in mindestens teilvernetzter Form, das Struktureinheiten aufweist, die durch direkte Kondensation von DOPO an endständige Oxiranringe des Epoxidharzes unter Bildung von Phosphor-Kohlenstoff-Bindungen erhältlich sind.The The invention relates to a flameproof epoxy resin in at least partially crosslinked Form that has structural units by direct condensation from DOPO to terminal Oxirane rings of the epoxy resin to form phosphorus-carbon bonds available are.

Solche flammfeste Epoxidharze sind beispielsweise aus EP 0 806 429 A2 bekannt.Such flame-retardant epoxy resins are for example made EP 0 806 429 A2 known.

DOPO, im früheren Schrifttum auch nur DOP genannt, ist 9,10-Dihydro-9-oxa-10-phosphaphenanthren-10-oxid, eine Verbindung, die sich leicht an endständige Oxiranringe von Epoxidharzen unter Bildung von Phosphor-Kohlenstoff-Einfachbindungen ankondensieren läßt.DOPO, in the earlier Also known as DOP, is 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, a compound that binds easily to terminal oxirane rings of epoxy resins to form phosphorus-carbon single bonds allowed to condense.

Die Flammschutzeigenschaften von flammfest ausgerüsteten brennbaren Materialien werden gemäß der weltweit akzeptieren Norm UL 94 (Underwriters Laboratoy) in die Klassen V-0, V-1 und V-2 eingeteilt (vergleiche Ullmann's Enzyklopädie der technischen Chemie, 6. Auflage, Band 14, Seite 57 (2003)). Die für die meisten praktischen Anwendungsfälle geforderte beste Klasse ist V-0.The Flame retardancy properties of flame-resistant combustible materials be according to the worldwide accept standard UL 94 (Underwriters Laboratoy) in the classes V-0, V-1 and V-2 (compare Ullmann's Encyclopedia of Industrial Chemistry, 6th edition, volume 14, page 57 (2003)). The required for most practical applications best class is V-0.

Die Flammfestigkeit eines entsprechend ausgerüsteten Polymers hängt bei Verwendung von DOPO als Flammschutzmittel direkt von der Phosphorkonzentration ab, die das ausgerüstete Harz aufweist. Je höher die Phosphorkonzentration ist, um so besser ist die Flammschutzwirkung. Mit der Erhöhung der Phosphorkonzentration eines Polymers sinkt jedoch gleichzeitig die Glasübergangstemperatur (Tg), wodurch die mechanischen Eigenschaften (Härte, Plastizität, Umformbarkeit) eines Polymers stark verändert werden. Bei flammfest ausgerüsteten Epoxidharzen wird grundsätzlich eine möglichst hohe Glasumwandlungstemperatur bei Flammschutzeigenschaften der Klasse V-0 und gleichzeitig möglichst geringer Phosphorkonzentration gefordert.The Flame resistance of a suitably equipped polymer depends Use of DOPO as a flame retardant directly from the phosphorus concentration that equipped that Resin. The higher the phosphorus concentration is, the better the flame retardancy. With the increase of Phosphorus concentration of a polymer, however, simultaneously decreases Glass transition temperature (Tg), whereby the mechanical properties (hardness, plasticity, formability) of a polymer changed greatly become. Equipped with flameproof Epoxy resins becomes basic one possible high glass transition temperature with flame retardant properties of Class V-0 and at the same time as possible low phosphorus concentration required.

Bisher war man der Auffassung, daß eine solche Eigenschaftskombination nur dann erreichbar ist, wenn die Flammfestmachung eines Epoxidharzes nach dem Masterbatch-Verfahren durchgeführt wird. Bei diesem Verfahren geht man von einem gewöhnlichen, nicht flammfest ausgerüsteten Epoxidharz aus und versetzt dieses gewöhnliche Harz mit einem Masterbatch aus einem hoch-modifizierten, flammfest ausgerüsteten Epoxidharz mit hohem Phosphorgehalt von beispielsweise 4 bis 7 Gew.-%. Da der Masterbatch beim Vermischen mit dem Basisharz wieder verdünnt wird, ergibt sich beim Endprodukt ein Phosphorgehalt von in der Regel 1 bis 3 Gew.-%.So far it was believed that a Such combination of properties can only be achieved if the Flameproofing of an epoxy resin according to the masterbatch process carried out becomes. This procedure is based on an ordinary, not flame retardant Epoxy resin and added to this ordinary resin with a masterbatch made of a highly modified, flame retardant epoxy resin with high Phosphorus content of, for example, 4 to 7 wt .-%. Because the masterbatch when diluted with the base resin is diluted again, results from the End product a phosphorus content of usually 1 to 3 wt .-%.

Der Erfindung liegt die Aufgabe zugrunde, die flammfesten Epoxidharze der eingangs genannten Gattung im Hinblick auf einen möglichst guten Kompromiß zwischen Phosphorgehalt, Glasübergangstemperatur und Flammschutzklasse weiter zu verbessern und ein möglichst einfach und zuverlässig durchführbares Verfahren zu ihrer Herstellung anzugeben.Of the Invention is based on the object, the flameproof epoxy resins of the type mentioned in terms of a possible good compromise between Phosphorus content, glass transition temperature and Flame protection class to further improve and as simple and reliable feasible Specify method for their preparation.

Diese Aufgabe wird erfindungsgemäß durch die Bereitstellung eines flammfesten Epoxidharzes mit den Merkmalen des Patentanspruchs 1 gelöst, also durch ein Harz, das gekennzeichnet ist durch einen Phosphorgehalt von mindestens 1 Gew.-% und durch eine Glasübergangstemperatur von mindestens 110°C.These Task is achieved by the provision of a flameproof epoxy resin having the features of claim 1, So by a resin that is characterized by a phosphorus content of at least 1% by weight and by a glass transition temperature of at least 110 ° C.

Vorzugsweise beträgt der Phosphorgehalt weniger als 2,0 Gew.-% und die Glasübergangstemperatur mindestens 145°C.Preferably is the phosphorus content is less than 2.0% by weight and the glass transition temperature is at least 145 ° C.

Das erfindungsgemäße Epoxidharz ist vorzugsweise mittels eines aminischen Härters gehärtet, wobei als Härter ein Poly(amin), vorzugsweise Diethylentoluoldiamin (DETDA), verwendet wird.The epoxy resin according to the invention is preferably cured by means of an amine hardener, wherein as a hardener Poly (amine), preferably diethylenetoluenediamine (DETDA) becomes.

Als besonders vorteilhaft haben sich DETDA-gehärtete Epoxidharze mit einem Phosphorgehalt von 1,0–1,5 Gew.-% und einer Glasübergangstemperatur von 150–180°C erwiesen, die allesamt der Flammschutzklasse V-0 gemäß der Norm UL 94 entsprechen.When DETDA-cured epoxy resins have a particularly advantageous with a Phosphorus content of 1.0-1.5 Wt .-% and a glass transition temperature from 150-180 ° C, all of which comply with the flame retardant class V-0 according to the UL 94 standard.

Das erfindungsgemäße Verfahren zur Herstellung flammfest ausgerüsteter Epoxidharze, bei dem ein Epoxidharz mit DOPO als reaktives Flammschutzmittel direkt umgesetzt und anschließend unter Zugabe eines Härters für Epoxidharze gehärtet wird, ist dadurch gekennzeichnet, daß DOPO in einer solchen Menge eingesetzt wird, daß die Phosphorkonzentration des ausgehärteten, flammfest ausgerüsteten Epoxidharzes mindestens 1 Gew.-% und die Glasübergangstemperatur (Tg) des Epoxidharzes mindestens 110°C betragen.The process according to the invention for producing flame-retardant epoxy resins, in which an epoxy resin is directly reacted with DOPO as a reactive flame retardant and then hardened with the addition of a hardener for epoxy resins, is characterized in that DOPO is used in such an amount that the phosphorus concentration of the cured, flame retardant epoxy resin min at least 1 wt .-% and the glass transition temperature (Tg) of the epoxy resin at least 110 ° C.

Vorzugsweise wird dabei DOPO in einer solchen Menge eingesetzt, daß die Phosphorkonzentration des Epoxidharzes weniger als 2,0 Gew.-% und die Glasübergangstemperatur mindestens 145°C betragen.Preferably DOPO is used in such an amount that the phosphorus concentration of the Epoxy resin less than 2.0 wt .-% and the glass transition temperature at least 145 ° C.

Als Epoxidharz wird vorzugsweise ein epoxidiertes Novolakharz verwendet, besonders bevorzugt ein Novolakharz, das Phenoxyglycidyl-Struktureinheiten aufweist.When Epoxy resin is preferably used an epoxidized novolak resin, particularly preferred is a novolak resin containing phenoxyglycidyl moieties having.

Als Härter wird vorzugsweise ein Polyamin) verwendet, besonders bevorzugt Diethylentoluoldiamin (DETDA).When Harder preferably a polyamine) is used, more preferably diethylenetoluenediamine (DETDA).

Vergleichsversuche, bei denen nach dem erfindungsgemäßen Verfahren hergestellte Epoxidharze (direktes Einkondensieren von DOPO) mit entsprechenden flammfest ausgerüsteten Epoxidharzen, die nach dem Masterbatch-Verfahren hergestellt wurden, verglichen wurden, sind in der folgenden Tabelle einander gegenübergestellt. In der Tabelle sind die Eigenschaften des Endprodukts, nämlich die Phosphorkonzentration, die Glasübergangstemperatur (Tg) und die Flammschutzklasse nach UL 94 angegeben:

Figure 00040001
Comparative experiments in which epoxy resins prepared by the process according to the invention (direct condensation of DOPO) were compared with corresponding flameproofed epoxy resins prepared by the masterbatch process are compared in the following table. The table shows the properties of the end product, namely the phosphorus concentration, the glass transition temperature (Tg) and the flame retardance class according to UL 94:
Figure 00040001

Als Härter wurde in den vorgenannten Beispielen jeweils DETDA verwendet. Alle Phosphorgehalte beziehen sich auf das Epoxidharz ohne Härter.When Harder DETDA was used in the above examples. All Phosphorus contents refer to the epoxy resin without hardener.

Aus den vorstehenden Ergebnissen ergibt sich für den Fachmann überraschenderweise, daß bei direktem Einkondensieren von DOPO schon bei einer um 50% geringeren Phosphorkonzentration die beste Flammschutzklasse V0 erreicht wird (verglichen mit dem Masterbatch-Verfahren), wobei aber gleichzeitig die Glasübergangstemperatur wesentlich höher ist (179°C bei 1% Phosphor – verglichen mit 119°C bei 2% Phosphor im Masterbatch-Verfahren).Out Surprisingly, the above results that at direct condensation of DOPO even at a 50% lower Phosphorus concentration the best flame protection class V0 is achieved (compared to the masterbatch method), but at the same time the glass transition temperature significantly higher is (179 ° C at 1% phosphorus - compared at 119 ° C at 2% phosphorus in the masterbatch process).

Das erfindungsgemäße Verfahren ist somit überraschend besser, weil bei gleichbleibenden Flammschutzeigenschaften wesentlich höhere Glasübergangstemperaturen erzielt werden können, obwohl nur die Hälfte der Phosphormenge zur Erreichung der V-0 Klasse erforderlich ist.The inventive method is thus surprising better, because with constant Flammschutzeigenschaften essential higher Glass transition temperatures can be achieved although only half the amount of phosphorus is required to reach the V-0 class.

Claims (11)

Flammfestes Epoxidharz in mindestens teilvernetzter Form, das Struktureinheiten aufweist, die durch direkte Kondensation von DOPO an endständige Oxiranringe des Epoxidharzes unter Bildung von Phosphor-Kohlenstoff-Bindungen erhältlich sind, gekennzeichnet durch einen Phosphorgehalt von mindestens 1 Gew.-% und eine Glasübergangstemperatur (Tg) von mindestens 110°C.Flameproof epoxy resin in at least partially crosslinked form, which has structural units which are characterized by di direct condensation of DOPO to terminal oxirane rings of the epoxy resin to form phosphorus-carbon bonds are available, characterized by a phosphorus content of at least 1 wt .-% and a glass transition temperature (Tg) of at least 110 ° C. Epoxidharz nach Anspruch 1, gekennzeichnet durch einen Phosphorgehalt von weniger als 2,0 Gew.-% und eine Tg von mindestens 145°C.Epoxy resin according to claim 1, characterized by a phosphorus content of less than 2.0% by weight and a Tg of at least 145 ° C. Epoxidharz nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß es mittels eines aminischen Härters gehärtet ist.Epoxy resin according to claim 1 or 2, characterized that it cured by means of an amine hardener. Epoxidharz nach Anspruch 3, dadurch gekennzeichnet, daß es mit Diethylentoluoldiamin (DETDA) gehärtet ist.Epoxy resin according to claim 3, characterized that it cured with diethylenetoluenediamine (DETDA). Epoxidharz nach Anspruch 4, dadurch gekennzeichnet, daß der Phosphorgehalt 1,0–1,5 Gew.-% und die Tg 150–180°C betragen.Epoxy resin according to claim 4, characterized that the Phosphorus content 1.0-1.5 Wt .-% and Tg 150-180 ° C amount. Epoxidharz nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß es der Flammschutzklasse V-0 gemäß der Norm UL 94 entspricht.Epoxy resin according to one of claims 1 to 5, characterized that it the flame retardant class V-0 according to the standard UL 94 corresponds. Verfahren zur Herstellung flammfest ausgerüsteter Epoxidharze, bei dem ein Epoxidharz mit DOPO als reaktivem Flammschutzmittel direkt umgesetzt und anschließend unter Zugabe eines Härters für Epoxidharze gehärtet wird, dadurch gekennzeichnet, daß DOPO in einer solchen Menge eingesetzt wird, daß die Phosphorkonzentration des ausgehärteten, flammfest ausgerüsteten Epoxidharzes mindestens 1 Gew.-% und die Glasübergangstemperatur (Tg) des Epoxidharzes mindestens 110°C betragen.Process for the preparation of flame-retardant epoxy resins, in which an epoxy resin with DOPO as a reactive flame retardant implemented directly and then with the addition of a hardener cured for epoxy resins, characterized in that DOPO is used in such an amount that the phosphorus concentration of the cured, equipped flame resistant Epoxy resin at least 1 wt .-% and the glass transition temperature (Tg) of the Epoxy resin at least 110 ° C be. Verfahren nach Anspruch 7, dadurch gekennzeichnet, daß DOPO in einer Menge eingesetzt wird, daß die Phosphorkonzentration des Epoxidharzes weniger als 2,0 Gew.-% und die Tg mindestens 145°C betragen.Method according to claim 7, characterized in that that DOPO is used in an amount such that the phosphorus concentration of the epoxy resin less than 2.0 wt .-% and the Tg at least 145 ° C. Verfahren nach Anspruch 7 oder 8, dadurch gekennzeichnet, daß als Epoxidharz ein epoxidiertes Novolakharz verwendet wird.Method according to claim 7 or 8, characterized that as Epoxy resin, an epoxidized novolak resin is used. Verfahren nach einem der Ansprüche 7 bis 9, dadurch gekennzeichnet, daß als Härter ein Polyamin) verwendet wird,Method according to one of claims 7 to 9, characterized that as Harder a polyamine) is used, Verfahren nach Anspruch 10, dadurch gekennzeichnet, daß als Härter Diethylentoluoldiamin (DETDA) verwendet wird.Method according to claim 10, characterized in that that as Harder Diethylentoluoldiamine (DETDA) is used.
DE200510042097 2005-09-05 2005-09-05 Flame-resistant epoxy resin is structured by a condensation at the oxiran rings to form phosphor-carbon compounds Ceased DE102005042097A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009013532A3 (en) * 2007-07-21 2009-03-19 Leighs Paints Coating compositions
WO2011015611A1 (en) * 2009-08-05 2011-02-10 Gurit (Uk) Ltd Fire-retardant composite materials
DE102011118490A1 (en) 2011-11-11 2013-05-16 Schill + Seilacher "Struktol" Gmbh Halogen-free flame-resistant epoxy resin composition useful for manufacturing moldings and/or composite materials including foils, comprises a hardener component for crosslinking the epoxy resin and a phosphorus-containing flame retardant

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009013532A3 (en) * 2007-07-21 2009-03-19 Leighs Paints Coating compositions
WO2011015611A1 (en) * 2009-08-05 2011-02-10 Gurit (Uk) Ltd Fire-retardant composite materials
US9909003B2 (en) 2009-08-05 2018-03-06 Gurit (Uk) Ltd. Fire-retardant composite materials
DE102011118490A1 (en) 2011-11-11 2013-05-16 Schill + Seilacher "Struktol" Gmbh Halogen-free flame-resistant epoxy resin composition useful for manufacturing moldings and/or composite materials including foils, comprises a hardener component for crosslinking the epoxy resin and a phosphorus-containing flame retardant

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