WO1993012170A1 - Resin composition, in particular for casting resin - Google Patents

Resin composition, in particular for casting resin Download PDF

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Publication number
WO1993012170A1
WO1993012170A1 PCT/EP1992/002912 EP9202912W WO9312170A1 WO 1993012170 A1 WO1993012170 A1 WO 1993012170A1 EP 9202912 W EP9202912 W EP 9202912W WO 9312170 A1 WO9312170 A1 WO 9312170A1
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WO
WIPO (PCT)
Prior art keywords
resin
resin composition
casting
isocyanate
metallic
Prior art date
Application number
PCT/EP1992/002912
Other languages
German (de)
French (fr)
Inventor
Hans Dammer
Original Assignee
Hans Dammer
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hans Dammer filed Critical Hans Dammer
Priority to JP5510629A priority Critical patent/JPH06505529A/en
Publication of WO1993012170A1 publication Critical patent/WO1993012170A1/en

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Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals

Definitions

  • the present invention relates to a resin composition, in particular a casting resin with a filler.
  • So-called epoxy isocyanate resins EPIC resins
  • EPIC resins are known from the prior art, which are produced by reaction of mixtures of epoxides
  • Q and isocyanates and optionally accelerators are obtained.
  • an epoxy isocyanate resin is known, for example, which is based on an isomeric mixture of diphenylmethane, 4'-diisocyanate and diphenylmethane-2,4'-diisocyanate as the isocyanate component and
  • These epoxy isocyanate resins are high temperature resistant thermosets and are used in combination with ceramic fillers as casting resins such. B. for the
  • the object of the present invention is the production of substances based on the abovementioned 25 epoxy isocyanate resins in conjunction with fillers which have novel properties and, on the basis of these properties, offer new application possibilities.
  • An object of the invention provides the solution to this problem
  • Resin composition based on the aforementioned epoxy isocyanate resin which is characterized by a proportion of a metallic filler.
  • the metallic filler can be in powder form or grained with a finer or coarser grain.
  • suitable metallic fillers ⁇ e are aluminum, copper, iron or steel. With these metallic fillers, casting resins are obtained which have the properties of the epoxy isocyanate resins mentioned at the outset, that is to say high Permanent temperature resistance, good pourability
  • inventive casting resins with metallic fillers are particularly well suited for the production of tools.
  • resin compositions of the invention are as
  • Particularly suitable materials that are subject to high mechanical and thermal stresses such as. B. as materials for
  • Constructions in the aerospace industry and also in the automotive industry »It is particularly advantageous for use as a construction material in aircraft construction as a property of the resin compositions according to the invention that they are in contrast to the metallic
  • Fillers copper, aluminum etc. are not themselves electrically conductive.
  • Another advantageous application is the use of the resin compositions according to the invention with metallic fillers for the production of bulletproof articles, for which these are particularly suitable owing to the great hardness.
  • a high temperature resistant mold casting resin is made from
  • Aluminum fine spray grit fine aluminum powder stirred in.
  • the freshly mixed EPIC resin has a comparatively low viscosity, so that the aluminum powder can be stirred in well and a suspension with uniform distribution of the aluminum particles is obtained.
  • the resin composition is allowed to vent a little before pouring.
  • the material hardens within about an hour at room temperature. The final strength is obtained by subsequent tempering, gradually bringing the material to a temperature of around 250 ° C and then tempering at this temperature for another four hours.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

A resin composition, in particular for a casting resin, contains an epoxide-isocyanate resin and a metallic filler. Granulated or finely powdered aluminium, copper, iron or steel, for example, are suitable as metallic fillers. These epoxide-isocyanate resins with metallic fillers have a particularly high thermal endurance limit, a good castability at the ambient temperature, are resistant to shrinkage during heating and are very hard after case hardening. These resin compositions are suitable in particular as tool manufacturing resins, among others.

Description

"Harzzusaminensetzung, insbesondere Gießharz" "Resin composition, especially cast resin"
Die vorliegende Erfindung betrifft eine Harzzusammensetzung, insbesondere ein Gießharz mit einem Füllstoff. Aus dem Stand der Technik bekannt sind sogenannte Epoxi-Isocyanat-Harze (EPIC-Harze) , die durch Reaktion von Mischungen aus EpoxidenThe present invention relates to a resin composition, in particular a casting resin with a filler. So-called epoxy isocyanate resins (EPIC resins) are known from the prior art, which are produced by reaction of mixtures of epoxides
,Q und Isocyanaten und gegebenenfalls Beschleunigern erhalten werden. Bekannt ist beispielsweise ein solches Epoxi-Isocyanat-Harz, bei dem ausgegangen wird aus einem isomeren Gemisch von Diphenylmethan- ,4'-Diisocyanat und Diphenylmethan-2,4'-Diisocyanat als Isocyanatkomponente und, Q and isocyanates and optionally accelerators are obtained. Such an epoxy isocyanate resin is known, for example, which is based on an isomeric mixture of diphenylmethane, 4'-diisocyanate and diphenylmethane-2,4'-diisocyanate as the isocyanate component and
,c einem aus Bisphenol A herstellbaren Produkt mit zwei, c a product that can be produced from bisphenol A with two
Epoxigruppen als Epoxiko ponente, wobei ein Amin als Härter zugesetzt wird. Diese Epoxi-Isocyanat-Harze sind hochtemperaturbeständige Duroplaste und werden in Kombination mit keramischen Füllstoffen als Gießharze z. B. für dieEpoxy groups as an epoxy component, with an amine being added as a hardener. These epoxy isocyanate resins are high temperature resistant thermosets and are used in combination with ceramic fillers as casting resins such. B. for the
20 Herstellung von Isolatoren für die Elektroindustrie verwendet.20 Manufacture of insulators used for the electrical industry.
Die Aufgabe der vorliegenden Erfindung ist die Herstellung von Substanzen auf Basis der vorgenannten 25 Epoxi-Isocyanat-Harze in Verbindung mit Füllstoffen, die neuartige Eigenschaften aufweisen und aufgrund dieser Eigenschaften neue Anwendungsmöglichkeiten bieten.The object of the present invention is the production of substances based on the abovementioned 25 epoxy isocyanate resins in conjunction with fillers which have novel properties and, on the basis of these properties, offer new application possibilities.
Die Lösung dieser Aufgabe liefert eine erfindungsgemäßeAn object of the invention provides the solution to this problem
30 Harzzusammensetzung auf Basis eines vorgenannten Epoxi-Isocyanat-Harzes, die durch einen Anteil an einem metallischen Füllstoff gekennzeichnet ist. Der metallische Füllstoff kann in Pulverform oder auch gekörnt mit feinerer oder gröberer Körnung vorliegen. Als metallische Füllstoffe αe kommen beispielsweise Aluminium, Kupfer, Eisen oder Stahl in Betracht. Mit diesen metallischen Füllstoffen werden Gießharze erhalten, die die Eigenschaften der eingangs genannten Epoxi-Isocyanat-Harze, also hohe Dauertemperaturbeständigkeit, gute Gießbarkeit bei30 Resin composition based on the aforementioned epoxy isocyanate resin, which is characterized by a proportion of a metallic filler. The metallic filler can be in powder form or grained with a finer or coarser grain. Examples of suitable metallic fillers αe are aluminum, copper, iron or steel. With these metallic fillers, casting resins are obtained which have the properties of the epoxy isocyanate resins mentioned at the outset, that is to say high Permanent temperature resistance, good pourability
Raumtemperatur, Schrumpffreiheit bei Erwärmen einerseits mit den Eigenschaften des metallischen Füllstoffs kombinieren.Combine room temperature, shrink-free when heated with the properties of the metallic filler.
Die erfindungsgernäßen Gießharze mit metallischen Füllstoffen eignen sich insbesondere gut zur Herstellung von Werkzeugen.The inventive casting resins with metallic fillers are particularly well suited for the production of tools.
Außerdem sind die erfindungsgemäßen Harzzusammensetzungen alsIn addition, the resin compositions of the invention are as
Werkstoffe besonders geeignet, die stark mechanisch und thermisch beansprucht werden, wie z. B. als Werkstoffe fürParticularly suitable materials that are subject to high mechanical and thermal stresses, such as. B. as materials for
Konstruktionen in der Luft- und Raumfahrtindustrie sowie auch im Automobilbau» Dabei ist für den Einsatz als Konstruktionsmaterial im Flugzeugbau als Eigenschaft der erfindungsgemäßen Harzzusammensetzungen besonders vorteilhaft, daß diese im Gegensatz zu den metallischenConstructions in the aerospace industry and also in the automotive industry »It is particularly advantageous for use as a construction material in aircraft construction as a property of the resin compositions according to the invention that they are in contrast to the metallic
Füllstoffen Kupfer, Aluminium etc. selbst nicht elektrisch leitend sind. Als weitere vorteilhafte Anwendung ist die Verwendung der erfindungsgernäßen Harzzusammensetzungen mit metallischen Füllstoffen zur Herstellung von schußfesten Artikeln vorgesehen, wofür diese sich aufgrund der großen Härte besonders eignen. Fillers copper, aluminum etc. are not themselves electrically conductive. Another advantageous application is the use of the resin compositions according to the invention with metallic fillers for the production of bulletproof articles, for which these are particularly suitable owing to the great hardness.
Nachfolgend wird die vorliegende Erfindung anhand von Ausführungsbeispielen näher beschrieben.The present invention is described in more detail below on the basis of exemplary embodiments.
Beispiel:Example:
Es wird ein hochtemperaturbeständiges Werkzeug-Gießharz hergestellt ausA high temperature resistant mold casting resin is made from
100 Masseteilen eines Isomerengemischs aus100 parts by weight of a mixture of isomers
Diphenylmethan-2-4'-Diisocyanat und Diphenylmethan-4-4'-Diisocyanat im Verhältnis 60 / 40Diphenylmethane 2-4'-diisocyanate and diphenylmethane 4-4'-diisocyanate in the ratio 60/40
5 Masseteilen Bisphenol-A-Diepoxid*5 parts by weight of bisphenol A diepoxide *
1 Masseteil Dimethylbenzylamin (Beschleuniger)1 part by weight of dimethylbenzylamine (accelerator)
* Hz Hz* Hz Hz
Figure imgf000005_0001
Figure imgf000005_0001
In dieses EPIC-Harz werden 150 Masseteile150 parts by mass are contained in this EPIC resin
Aluminiumfeinsprühgries (feines Aluminiumpulver) eingerührt, Das frisch angerührte EPIC-Harz hat eine vergleichsweise geringe Viskosität, so daß sich das Aluminiumpulver gut einrühren läßt und eine Suspension mit gleichmäßiger Verteilung der Aluminiumpartikel erhalten wird. Nach dem Einrühren läßt man die Harzzusammensetzung vor dem Gießen etwas entlüften. Nach dem Verguß härtet das Material bei Raumtemperatur innerhalb von etwa einer Stunde aus. Die endgültige Festigkeit erhält man durch anschließendes Tempern, wobei man das Material schrittweise auf eine Temperatur von etwa 250° C bringt und dann bei dieser Temperatur noch einmal vier Stunden tempert. Aluminum fine spray grit (fine aluminum powder) stirred in. The freshly mixed EPIC resin has a comparatively low viscosity, so that the aluminum powder can be stirred in well and a suspension with uniform distribution of the aluminum particles is obtained. After stirring, the resin composition is allowed to vent a little before pouring. After casting, the material hardens within about an hour at room temperature. The final strength is obtained by subsequent tempering, gradually bringing the material to a temperature of around 250 ° C and then tempering at this temperature for another four hours.

Claims

Patentansprüche Claims
1. Harzzusammensetzung, insbesondere Gießharz, enthaltend einen Füllstoff, dadurch gekennzeichnet, daß diese ein Epoxi-Isocyanat-Harz ist, das einen metallischen Füllstoff enthält.1. Resin composition, in particular cast resin, containing a filler, characterized in that it is an epoxy isocyanate resin which contains a metallic filler.
2. Harzzusammensetzung, insbesondere Gießharz, nach Anspruch 1, dadurch gekennzeichnet, daß der metallische Füllstoff in der Harzzusammensetzung in Pulverform vorliegt.2. Resin composition, in particular casting resin, according to claim 1, characterized in that the metallic filler in the resin composition is in powder form.
3. Harzzusammensetzung, insbesondere Gießharz, nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß der metallische Füllstoff in der Harzzusammensetzung in gekörnter Form vorliegt.3. Resin composition, in particular casting resin, according to claim 1 or 2, characterized in that the metallic filler is present in the resin composition in granular form.
4. Harzzusammensetzung, insbesondere Gießharz, nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß der metallische Füllstoff Aluminium, Kupfer, Eisen oder Stahl ist.4. Resin composition, in particular cast resin, according to one of claims 1 to 3, characterized in that the metallic filler is aluminum, copper, iron or steel.
5. Harzzusammensetzung, insbesondere Gießharz, nach einem . der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß diese ausgehend von einem Diisocyanat als Isoc anatkomponte herstellbar ist.5. Resin composition, especially cast resin, after a. of claims 1 to 4, characterized in that it can be prepared from a diisocyanate as an isocyanate component.
6. Harzzusammensetzung, insbesondere Gießharz, nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß diese als Isocyanatkomponente Diphenylmethan-4,4'-Diisocyanat und/oder Diphenylmethan-2,4'-Diisocyanat enthält.6. Resin composition, in particular casting resin, according to one of claims 1 to 5, characterized in that it contains diphenylmethane-4,4'-diisocyanate and / or diphenylmethane-2,4'-diisocyanate as the isocyanate component.
7. Harzzusammensetzung, insbesondere Gießharz, nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß diese ausgehend von einem Bisphenol A-Derivat als Epoxikomponente herstellbar ist. 7. Resin composition, in particular cast resin, according to one of claims 1 to 6, characterized in that it can be prepared starting from a bisphenol A derivative as an epoxy component.
8. Verwendung einer Harzzusammensetzung gemäß einem der Ansprüche 1 bis 7 zur Herstellung von Werkzeugen.8. Use of a resin composition according to any one of claims 1 to 7 for the manufacture of tools.
9. Verwendung einer Harzzusammensetzung gemäß einem der Ansprüche 1 bis 7 als Werkstoff im Flugzeug- oder Automobilbau.9. Use of a resin composition according to one of claims 1 to 7 as a material in aircraft or automobile construction.
10. Verwendung einer Harzzusammensetzung gemäß einem der Ansprüche 1 bis 7 zur Herstellung von schußfesten Artikeln, insbesondere Platten oder dergleichen. 10. Use of a resin composition according to any one of claims 1 to 7 for the manufacture of bulletproof articles, in particular sheets or the like.
PCT/EP1992/002912 1991-12-19 1992-12-15 Resin composition, in particular for casting resin WO1993012170A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5510629A JPH06505529A (en) 1991-12-19 1992-12-15 Resin compositions, especially casting resins

Applications Claiming Priority (2)

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DE19914141963 DE4141963C2 (en) 1991-12-19 1991-12-19 Resin composition, especially cast resin
DEP4141963.4 1991-12-19

Publications (1)

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JP (1) JPH06505529A (en)
AU (1) AU3256593A (en)
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WO (1) WO1993012170A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0743338A1 (en) * 1995-05-15 1996-11-20 Nippon Oil Company, Ltd. Composite having excellent dynamic characteristics, migration characteristics or both characteristics and process for producing the same
EP1101783A2 (en) * 1999-11-22 2001-05-23 Vantico AG Casting resin and process for the fabrication of resin molds
US6610230B2 (en) 2001-08-31 2003-08-26 National Research Council Of Canada Method of making mold using elongated metal elements
EP1927621A1 (en) * 2006-12-01 2008-06-04 Dow Gloval Technologies Inc. Metal filled polyurethane composition and moulds prepared therefrom

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4335115A1 (en) * 1993-10-15 1995-06-08 P I V Tschan Gmbh An elastic transmission element, improved mechanically for long life
DE102007035521A1 (en) * 2007-07-26 2009-01-29 Martin Miethner Device useful in shower device for regulating properties of flowing water, comprises housing having inlet and outlet for conducting the water through the housing, and water-impermeable mold body containing an active substance
EP2801585A1 (en) 2013-05-06 2014-11-12 Hüther Ulrich Compressed porous moulded part based on epoxide-isocyanate resin
DE202013012084U1 (en) 2013-05-06 2015-02-26 Ulrich Hüther Compacted porous body
EP2801463B1 (en) 2013-05-06 2016-03-30 Ulrich Hüther Casting resin
DE202015100825U1 (en) 2015-02-20 2015-03-02 Ulrich Hüther Compacted porous body

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US3018260A (en) * 1955-01-03 1962-01-23 Chem Dev Corp Room temperature curing molding and forming composition
FR1347301A (en) * 1962-03-15 1963-12-27 Boeing Co Improvements to molding compositions based on epoxy resin containing metal particles, to articles made using these compositions, and to processes for molding these compositions
US3767624A (en) * 1971-12-27 1973-10-23 Dow Chemical Co Oxazolidinone modified epoxy novolac resin
GB2109384A (en) * 1981-11-02 1983-06-02 Grace W R & Co Thermosetting urethane compositions based on an epoxy resin
EP0412891A2 (en) * 1989-08-07 1991-02-13 Nissan Motor Co., Ltd. Metal-powder filled epoxy resin mold and method of producing the same

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DE3323122A1 (en) * 1983-06-27 1985-05-23 Siemens AG, 1000 Berlin und 8000 München METHOD FOR PRODUCING REACTION RESIN MOLDINGS

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3018260A (en) * 1955-01-03 1962-01-23 Chem Dev Corp Room temperature curing molding and forming composition
FR1347301A (en) * 1962-03-15 1963-12-27 Boeing Co Improvements to molding compositions based on epoxy resin containing metal particles, to articles made using these compositions, and to processes for molding these compositions
US3767624A (en) * 1971-12-27 1973-10-23 Dow Chemical Co Oxazolidinone modified epoxy novolac resin
GB2109384A (en) * 1981-11-02 1983-06-02 Grace W R & Co Thermosetting urethane compositions based on an epoxy resin
EP0412891A2 (en) * 1989-08-07 1991-02-13 Nissan Motor Co., Ltd. Metal-powder filled epoxy resin mold and method of producing the same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0743338A1 (en) * 1995-05-15 1996-11-20 Nippon Oil Company, Ltd. Composite having excellent dynamic characteristics, migration characteristics or both characteristics and process for producing the same
EP1101783A2 (en) * 1999-11-22 2001-05-23 Vantico AG Casting resin and process for the fabrication of resin molds
EP1101783A3 (en) * 1999-11-22 2001-09-19 Vantico AG Casting resin and process for the fabrication of resin molds
US6602936B1 (en) 1999-11-22 2003-08-05 Vantico, Inc. Casting resin and process for the fabrication of resin molds
US6610230B2 (en) 2001-08-31 2003-08-26 National Research Council Of Canada Method of making mold using elongated metal elements
EP1927621A1 (en) * 2006-12-01 2008-06-04 Dow Gloval Technologies Inc. Metal filled polyurethane composition and moulds prepared therefrom
WO2008065090A1 (en) * 2006-12-01 2008-06-05 Dow Global Technologies Inc. Metal filled polyurethane composition and moulds prepared therefrom

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Publication number Publication date
DE4141963C2 (en) 1997-03-20
EP0572619A1 (en) 1993-12-08
JPH06505529A (en) 1994-06-23
AU3256593A (en) 1993-07-19
DE4141963A1 (en) 1993-06-24

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