DE1073200B - Process for accelerating the curing of basic derivatives of tertiary mono- or polyamines containing at least two epoxy groups - Google Patents
Process for accelerating the curing of basic derivatives of tertiary mono- or polyamines containing at least two epoxy groupsInfo
- Publication number
- DE1073200B DE1073200B DENDAT1073200D DE1073200DA DE1073200B DE 1073200 B DE1073200 B DE 1073200B DE NDAT1073200 D DENDAT1073200 D DE NDAT1073200D DE 1073200D A DE1073200D A DE 1073200DA DE 1073200 B DE1073200 B DE 1073200B
- Authority
- DE
- Germany
- Prior art keywords
- curing
- accelerating
- epoxy groups
- polyamines containing
- tertiary mono
- 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.)
- Pending
Links
- 125000003700 epoxy group Chemical group 0.000 title description 5
- 229920000768 polyamine Polymers 0.000 title description 5
- 238000000034 method Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 description 9
- 239000003990 capacitor Substances 0.000 description 8
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N Quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 6
- 229940093918 Quinoline gynecological antiinfectives Drugs 0.000 description 6
- 229940027991 antiseptics and disinfectants Quinoline derivatives Drugs 0.000 description 6
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 238000005266 casting Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3aS,7aR)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- QSMUFXXTSUEZJA-UHFFFAOYSA-N 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid Chemical compound O=C1N(CC=2C=CC=CC=2)C(C(=O)O)C(C(O)=O)N1CC1=CC=CC=C1 QSMUFXXTSUEZJA-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 210000001847 Jaw Anatomy 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- -1 jaws Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052904 quartz Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
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
- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
-
- 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
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Insulating Materials (AREA)
Description
Verfahren zum Beschleunigen der Aushärtung von basischen, mindestens zwei Epoxydgruppen aufweisenden Derivaten von tertiären Mono- oder Polyaminen Es ist bekannt, basische, mindestens zwei Epoxydgruppen aufweisende Derivate von tertiären Mono-oder Polyaminen durch Härten mit cyclischen Säureanhydriden in unlösliche Kunststoffe zu überführen. Method of accelerating the hardening of basic, at least two epoxy-containing derivatives of tertiary mono- or polyamines Es is known, basic, at least two epoxy groups containing derivatives of tertiary Mono- or polyamines by curing with cyclic acid anhydrides in insoluble plastics to convict.
Derartige Kombinationen finden als Gießharze, Backe, Klebstoffe und elektrische Isolierstoffe praktische Verwendung.Such combinations are found as casting resins, jaws, adhesives and electrical insulating materials practical use.
Die Härtungseigenschaften dieser Kombinationen entsprechen jedoch auf einigen Anwendungsgebieten nicht immer den gestellten Anforderungen hinsichtlich derAushärtungszeiten und der erforderlichen Härtungstemperaturen, zumal praktisch nur Hexahydrophthalsäureanhydrid angewendet werden kann. However, the curing properties of these combinations are the same in some areas of application not always the set requirements with regard to the curing times and the required curing temperatures, especially practical only hexahydrophthalic anhydride can be used.
Es wurde nun gefunden, daß sich die Aushärtung der genannten Hexahydrophthalsäureanhydrid als Härtungsmittel aufweisenden Kombinationen durch einen Zusatz von Chinolin und/oder Chinolinderivaten beschleunigen läßt, wobei gleichzeitig die Aushärtungseigenschaften der genannten Produkte und die Eigenschaften der ausgehärteten Produkte selbst, insbesondere deren elektrische Werte, verbessert werden. It has now been found that the curing of the hexahydrophthalic anhydride mentioned as hardening agent combinations by adding quinoline and / or Quinoline derivatives can accelerate, while at the same time the curing properties the named products and the properties of the cured products themselves, in particular their electrical values are improved.
Geeignete Derivate von tert. Mono- oder Polyaminen mit mindestens zwei Epoxydgruppen sind in der deutschen Auslegeschrift 1 ei9083 beschrieben. Suitable derivatives of tert. Mono- or polyamines with at least two epoxy groups are in of the German Auslegeschrift 1 ei9083.
Es seien beispielsweise die Verbindungen der folgenden Formeln angeführt: worin R einen Alkylrest und X null oder eine ganze Zahl bedeutet.For example, the compounds of the following formulas are given: where R is an alkyl radical and X is zero or an integer.
Als Härtungsmittel für diese Polyepoxyde hat sich insbesondere das cis-Hexahydrophthalsäureanhydrid als geeignet erwiesen. Als Beschleuniger kommen neben Chinolin alkyl-, aryl-, aralkyl-, alkoxy- und oxy-substituierte Chinolinderivate, insbesondere 2-Methylchinolin in Frage. Diese Beschleuniger werden vorzugsweise in Mengen von etwa 1 bis 5 Gewichts- prozent, bezogen auf Polyepoxydverbindungen, eingesetzt. The hardening agent for these polyepoxides has proven to be particularly good cis-hexahydrophthalic anhydride proved to be suitable. Come as an accelerator in addition to quinoline, alkyl-, aryl-, aralkyl-, alkoxy- and oxy-substituted quinoline derivatives, especially 2-methylquinoline in question. These accelerators are preferred in amounts of about 1 to 5 weight percent, based on polyepoxy compounds, used.
Die genannten Kombinationen aus Polyepoxyden, Hexahydrophthalsäureanhydrid und Chinolin, bzw. The mentioned combinations of polyepoxides, hexahydrophthalic anhydride and quinoline, resp.
Chinolinderivaten, eignen sich besonders als Imprägnier- und als Vergußmassen für die Herstellung von elektrischen Bauelementen, wie z. B. Kondensatoren oder Spulen. Durch den Zusatz der Beschleuniger wird die Aushärtungszeit der genannten Ansätze wesentlich herabgesetzt, ohne daß hierbei die Topfzeit der Mischungen verkürzt wird.Quinoline derivatives are particularly suitable as impregnation and casting compounds for the production of electrical components, such as B. capacitors or Wash. By adding the accelerator, the curing time becomes that of the above approaches significantly reduced without the pot life of the mixtures being shortened.
Beispiel 1 10 Teile eines tert.Aminogruppen enthaltenden basischen Polyepoxyds, wie es beispielsweise durch Umsetzen von 1 Mol Anilin und 2,2 Mol Epichlorhydrin erhalten wird, werden mit 12 Teilen Hexahydrophthalsäureanhydrid gemischt. Zu dieser Mischung werden 0,24 Teile 2-Methylchinolin gegeben. Die Mischung ist bei Raumtemperatur flüssig und gelbbraun gefärbt. Example 1 10 parts of a basic containing tertiary amino groups Polyepoxyds, as it is, for example, by reacting 1 mole of aniline and 2.2 moles of epichlorohydrin is obtained are mixed with 12 parts of hexahydrophthalic anhydride. To this 0.24 part of 2-methylquinoline is added to the mixture. The mixture is at room temperature liquid and yellow-brown in color.
Mit diesem Ansatz wird eine Imprägnierung von Papierwickelkondensatoren durchgeführt, wobei folgende Bedingungen eingehalten werden: Vakuum: 0,03 mm Hg; Temperatur beim Imprägnieren: 70 bis 900 C; Imprägnierdauer: 2 Stunden.This approach is used to impregnate paper wound capacitors carried out under the following conditions: vacuum: 0.03 mm Hg; Impregnation temperature: 70 to 900 C; Impregnation time: 2 hours.
Die Aushärtung der imprägnierten Kondensatoren erfordert 4 Stunden bei 1000 C. Die »Topfzeit« der obigen Mischung bei Raumtemperatur beträgt 2 bis 3 Tage.The impregnated capacitors take 4 hours to cure at 1000 C. The "pot life" of the above mixture at room temperature is 2 to 3 days.
Wird die Imprägnierung mit dem gleichen Ansatz, jedoch ohne Zusatz von 2-Methylchinolin durchgeführt, so betragen die Aushärtungszeiten 9 bis 16 Stunden bei 1000 C, während die »Topfzeit« der Ansätze die gleiche ist wie bei dem obigen Ansatz. If the impregnation is done with the same approach, but without an additive carried out by 2-methylquinoline, the curing times are 9 to 16 hours at 1000 C, while the "pot life" of the approaches is the same as the one above Approach.
Wenn die elektrischen Eigenschaften der Kondensatoren, die nach dem obigen Verfahren mit und ohne Zusatz imprägniert worden sind, miteinander verglichen werden, so ergeben sich folgende Werte: Der Verlauf der Verlustfaktorkurve in Abhängigkeit von der Temperatur ist bei den erfindungsgemäß behandelten Kondensatoren günstiger als bei den in bekannter Weise hergestellten Kondensatoren. Der Isolationswiderstand bei ersteren liegt höher. Die Isolationswerte für die unter Verwendung von 2-Methylchinolin hergestellten Kondensatoren betragen etwa 25000 MQ, während sie bei den ohne Zusatz von Methylchinolin hergestellten Kondensatoren bei etwa 3000 MQ liegen. Ferner beginnt die Ionisation erst bei höherer Spannungsbelastung (647 Volt gegenüber 475 Volt). Schließlich ist die Änderung der Kapazitätswerte geringer bei höheren Temperaturen und gleichmäßiger bei tieferen Temperaturen. If the electrical properties of the capacitors after the above methods have been impregnated with and without additives, compared with one another the following values result: The course of the loss factor curve as a function of the temperature is more favorable in the case of the capacitors treated according to the invention than with the capacitors manufactured in a known manner. The insulation resistance the former is higher. The isolation values for those using 2-methylquinoline manufactured capacitors amount to about 25000 MQ, while at the without addition Capacitors made from methylquinoline are around 3000 MQ. Further begins ionization only at higher voltage loads (647 volts versus 475 volts). Finally, the change in the capacitance values is less at higher temperatures and more evenly at lower temperatures.
Dieser Befund ist um so überraschender, als das 2-Methylchinolin wohl auch auf die Härtung von Glycidylpolyäthan auf Basis von Diphenolen eine beschleunigte Wirkung ausübt, hierbei jedoch nicht die erfindungsgemäßen Vorteile erzielt werden. Die beschleunigende Wirkung ist wesentlich geringer als bei den vorliegenden basischen Harzen. Außerdem besitzen die gehärteten Produkte keine besseren elektrischen Eigenschaften im Vergleich mit solchen, die ohne Zusatz des Beschleunigers hergestellt werden. This finding is all the more surprising as the 2-methylquinoline probably also an accelerated hardening of glycidyl polyethane based on diphenols Has an effect, but does not achieve the advantages of the invention. The accelerating effect is much less than that of the present basic ones Resins. In addition, the cured products do not have better electrical properties in comparison with those made without the addition of the accelerator.
Die erfindungsgemäß verwendeten Mischungen eignen sich auch als Vergußmassen für elektrische Bauteile, wobei es vorteilhaft ist diesen Massen Füllstoffe, wie z. B. Glas, Quarz, Rüß oder Kieselsäure-Aerogel, zuzusetzen. The mixtures used according to the invention are also suitable as casting compounds for electrical components, where it is advantageous to fillers such as these masses z. B. glass, quartz, soot or silica airgel to be added.
PATENTSPRUCH: Verfahren zum Beschleunigen der Aushärtung von basischen, mindestens zwei Epoxydgruppen aufweisenden Derivaten von tertiären Mono- oder Polyaminen durch Hexahydrophthalsäureanhydrid, dadurch gekennzeichnet, daß als Beschleunigungsmittel Chinolin und/oder Chinolinderivate verwendet werden. PATENT CLAIM: Process to accelerate the hardening of basic, derivatives of tertiary mono- or polyamines containing at least two epoxy groups by hexahydrophthalic anhydride, characterized in that as an accelerator Quinoline and / or quinoline derivatives can be used.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1073200B true DE1073200B (en) | 1960-01-14 |
Family
ID=597509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1073200D Pending DE1073200B (en) | Process for accelerating the curing of basic derivatives of tertiary mono- or polyamines containing at least two epoxy groups |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1073200B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1271992B (en) * | 1962-09-07 | 1968-07-04 | Siemens Ag | Process for the production of molded articles on the basis of epoxy compounds |
| WO1985005215A1 (en) * | 1984-05-09 | 1985-11-21 | Hughes Aircraft Company | Heat curable polyglycidyl aromatic amine encapsulants |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1019083B (en) * | 1956-01-28 | 1957-11-07 | Bayer Ag | Process for the production of plastics by hardening epoxy compounds |
-
0
- DE DENDAT1073200D patent/DE1073200B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1019083B (en) * | 1956-01-28 | 1957-11-07 | Bayer Ag | Process for the production of plastics by hardening epoxy compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1271992B (en) * | 1962-09-07 | 1968-07-04 | Siemens Ag | Process for the production of molded articles on the basis of epoxy compounds |
| WO1985005215A1 (en) * | 1984-05-09 | 1985-11-21 | Hughes Aircraft Company | Heat curable polyglycidyl aromatic amine encapsulants |
| JPS61502059A (en) * | 1984-05-09 | 1986-09-18 | ヒユ−ズ・エアクラフト・カンパニ− | How to enclose electrical parts |
| JPH0381243B2 (en) * | 1984-05-09 | 1991-12-27 | Hughes Aircraft Co |
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