DE1151933B - Process for the production of molded articles or coatings from boron-modified epoxy resins - Google Patents

Process for the production of molded articles or coatings from boron-modified epoxy resins

Info

Publication number
DE1151933B
DE1151933B DEL36542A DEL0036542A DE1151933B DE 1151933 B DE1151933 B DE 1151933B DE L36542 A DEL36542 A DE L36542A DE L0036542 A DEL0036542 A DE L0036542A DE 1151933 B DE1151933 B DE 1151933B
Authority
DE
Germany
Prior art keywords
epoxy resins
coatings
boron
production
modified epoxy
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
Application number
DEL36542A
Other languages
German (de)
Inventor
Dr-Ing Paul Nowak
Rer Nat Ernst Friedjof Webe Dr
Dipl-Ing Wolfram Busch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Licentia Patent Verwaltungs GmbH
Original Assignee
Licentia Patent Verwaltungs GmbH
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 Licentia Patent Verwaltungs GmbH filed Critical Licentia Patent Verwaltungs GmbH
Priority to DEL36542A priority Critical patent/DE1151933B/en
Priority claimed from GB3252661A external-priority patent/GB948202A/en
Publication of DE1151933B publication Critical patent/DE1151933B/en
Pending legal-status Critical Current

Links

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
    • C08G59/20—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
    • 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
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4078—Curing agents not provided for by the groups C08G59/42 - C08G59/66 boron containing compounds
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)

Description

INTERNAT. KL. C 08 gINTERNAT. KL. C 08 g

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

L 36542 IVc/39bL 36542 IVc / 39b

ANMELDETAG: 11. JULI 1960REGISTRATION DATE: JULY 11, 1960

BEKANNTMACHUNG DER ANMELDUNG UND AUSGABE DER AUSLEGESCHRIFT: 25. JULI 1963NOTICE THE REGISTRATION AND ISSUE OF THE EDITORIAL: JULY 25, 1963

Es ist bereits bekannt, Epoxyharze mit Titansäureestern zu modifizieren. Dabei sollen die freien Hydroxylgruppen im Harzmolekül esterartig gebunden werden. Ein Nachteil beim Umsetzen der Epoxyharze mit höherem Epoxydäquivalent als 300 mit Titansäureestern besteht darin, daß die beim Umsetzen erforderlichen hohen Temperaturen den katalytischen Effekt des Titans verstärken, so daß ein Teil der Epoxydgruppen untereinander reagiert und ein gelartiges Produkt entsteht.It is already known to modify epoxy resins with titanic acid esters. The free hydroxyl groups should are bonded like an ester in the resin molecule. A disadvantage of converting the epoxy resins with higher epoxy equivalent than 300 with titanic acid esters is that the reaction required high temperatures intensify the catalytic effect of the titanium, so that part of the Epoxy groups react with one another and a gel-like product is created.

Erfindungsgemäß wird dieser Nachteil vermieden und Formteile mit hoher Wärmebeständigkeit und guten elektrischen Eigenschaften erhalten. Die Formmassen eignen sich als Gieß- und Imprägniermassen sowie als Lacke.According to the invention, this disadvantage is avoided and molded parts with high heat resistance and obtained good electrical properties. The molding compounds are suitable as casting and impregnating compounds as well as lacquers.

Gegenstand der Erfindung ist somit ein Verfahren zum Herstellen von Formkörpern oder Überzügen durch Hitzehärten von Formmassen, die bormodifizierte Epoxyharze — erhalten durch Umsetzen von OH-gruppenhaltigen organischen Polymeren mit Trialkylboraten — sowie Dicarbonsäureanhydride enthalten. Das Verfahren ist dadurch gekennzeichnet, daß als OH-gruppenhaltige Polymere Epoxyharze auf Bisphenolbasis umgesetzt worden sind.The invention thus relates to a method for producing molded bodies or coatings by thermosetting molding compounds, the boron-modified epoxy resins - obtained by reacting Organic polymers containing OH groups with trialkyl borates and dicarboxylic acid anhydrides. The process is characterized in that the OH group-containing polymers are epoxy resins based on bisphenol have been implemented.

Das im Polymeren eingebaute Boratom wirkt nur bei höheren Temperaturen in dieser Formmasse als Beschleuniger. Durch eine Veresterung werden nahezu alle Hydroxylgruppen im Molekül gebunden, so daß diese Formmassen eine verhältnismäßig lange Gebrauchsdauer aufweisen, d. h., bei einer Lagerzeit bis etwa 15O0C tritt keine Reaktion ein. Durch weitere Temperaturerhöhung bis auf etwa 16O0C erfolgt dagegen rasche Härtung. Die Formmassen lassen sich bei 1400C im dünnflüssigen Zustand vergießen, ohne bei dieser Temperatur wahrnehmbar zu härten; die Massen können also bei dieser Temperatur über einen langen Zeitraum verarbeitet werden. Durch eine weitere Temperaturerhöhung auf mindestens 1600C erfolgt eine rasche Umsetzung.The boron atom built into the polymer only acts as an accelerator in this molding compound at higher temperatures. By esterification almost all hydroxyl groups are bonded in the molecule so that these molding compositions have a relatively long service life, ie, no reaction occurs at a storage time of up to about 15O 0 C. Rapid curing on the other hand is done by further increasing the temperature to about 16O 0 C. The molding compounds can be poured in the thin liquid state at 140 ° C. without noticeably hardening at this temperature; the masses can therefore be processed over a long period of time at this temperature. A further increase in temperature to at least 160 ° C. results in rapid conversion.

Polymere auf Bisphenol-A-Basis mit höherem Epoxydäquivalent und damit höherer Hydroxylzahl lassen sich mit Tributylborat leicht umestern. Die Umsetzung kann bei verhältnismäßig niedrigen Temperaturen erfolgen, bei denen praktisch mit keinem Verlust an Epoxydgruppen zu rechnen ist, selbst bei Umsetzung mit Epoxyharzen mit höherem Epoxydäquivalent, z. B. von 500. Die Herstellung der Ausgangsprodukte, auf die hier kein Schutz beansprucht wird, kann wie folgt erfolgen:Polymers based on bisphenol A with a higher epoxy equivalent and thus a higher hydroxyl number can easily be transesterified with tributyl borate. The reaction can take place at relatively low temperatures take place in which practically no loss of epoxy groups is to be expected, even with Implementation with epoxy resins with a higher epoxy equivalent, e.g. B. from 500. The production of the starting products, For which no protection is claimed here, can be done as follows:

1. 1000 Teile eines Epoxyharzes mit einem Epoxydäquivalent von 190 und einem Hydroxylgruppengehalt pro Mol von 0,2 werden mit 45 Teilen Verfahren zum Herstellen von Formkörpern oder Überzügen aus bormodifizierten1. 1000 parts of an epoxy resin with an epoxy equivalent of 190 and a hydroxyl group content per mole of 0.2, 45 parts are used to produce moldings or coatings from modified boron

EpoxyharzenEpoxy resins

Anmelder:Applicant:

Licentia Patent-Verwaltungs-G. m. b. H.,
Frankfurt/M., Theodor-Stern-Kai 1Licentia Patent-Verwaltungs-G. mb H.,
Frankfurt / M., Theodor-Stern-Kai 1

Dr.-Ing. Paul Nowak, Kassel,Dr.-Ing. Paul Nowak, Kassel,

Dr. rer. nat. Ernst Friedjof Weber, Neu Isenburg,Dr. rer. nat. Ernst Friedjof Weber, Neu Isenburg,

und Dipl.-Ing. Wolfram Busch, Wiesbaden,and Dipl.-Ing. Wolfram Busch, Wiesbaden,

sind als Erfinder genannt wordenhave been named as inventors

Tributylborat versetzt und das entstehende Butanol (etwa 180 g) im Vakuum bei 12O0C abgezogen. Es wird ein viskoses klares Produkt erhalten.Tributyl borate was added and the resulting butanol drawn off (approximately 180 g) under vacuum at 12O 0 C. A viscous clear product is obtained.

2. 1000 Teile eines Epoxyharzes mit einem Epoxydäquivalent von 500 und einem Hydroxylgruppengehalt pro Mol von 2 werden mit 450 Teilen Tributylborat vermischt und das entstehende Butanol bei 1200C im Vakuum entfernt. Es wird ein Produkt erhalten, das in der Wärme hochviskos ist, beim Abkühlen auf Raumtemperatur fest wird.2. 1000 parts of an epoxy resin with an epoxy equivalent of 500 and a hydroxyl group content per mole of 2 are mixed with 450 parts of tributyl borate and the butanol formed is removed at 120 ° C. in vacuo. A product is obtained which is highly viscous when heated and solidifies on cooling to room temperature.

Beispiel 1example 1

Teile eines nach 1 hergestellten Produktes werden mit 150 Teilen Hexahydrophthalsäureanhydrid in der Wärme vermischt und bei 1500C innerhalb Stunden zu einer festen harten Masse ausgehärtet.Parts of a product prepared according to 1 are mixed with 150 parts of hexahydrophthalic anhydride in the heat and hardened at 150 ° C. within hours to form a solid, hard mass.

Beispiel 2Example 2

Teile eines nach 2 hergestellten modifizierten Epoxyharzes werden mit 140 Teilen Dodecenylbernsteinsäureanhydrid in der Hitze vermischt und innerhalb 2 Stunden bei 16O0C zu einem festen harten Gießling gehärtet.Parts of a modified epoxy resin prepared according to 2 are mixed with 140 parts of dodecenyl succinic anhydride in the heat and cured within 2 hours at 16O 0 C for a fixed hard casting.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zum Herstellen von Formkörpern oder Überzügen durch Hitzehärten von Formmassen, die bormodifizierte Epoxyharze — erhalten durchProcess for the production of moldings or coatings by heat curing molding compounds, the boron modified epoxy resins - obtained through 309 648/292309 648/292 3 43 4 Umsetzen von OH-gruppenhaltigen organischen In Betracht gezogene Druckschriften:Implementation of OH-containing organic publications considered: Polymeren mit Trialkylboraten — sowie Di- Französische Patentschrift Nr. 1 198 633;Polymers with trialkyl borates - as well as French Patent No. 1,198,633; carbonsäureanhydride enthalten, dadurch gekenn- belgische Patentschrift Nr. 564 374. zeichnet, daß als OH-gruppenhaltige Polymerecontain carboxylic acid anhydrides, characterized by Belgian patent specification No. 564 374. It is characterized by the fact that polymers containing OH groups Epoxyharze auf Bisphenolbasis umgesetzt worden 5 I« Betracht gezogene ältere Patente:Bisphenol-based epoxy resins have been implemented 5 I «Older patents considered: sind. Deutsches Patent Nr. 1 107 935.are. German Patent No. 1 107 935. © 309 648/292 7.63© 309 648/292 7.63
DEL36542A 1960-07-11 1960-07-11 Process for the production of molded articles or coatings from boron-modified epoxy resins Pending DE1151933B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEL36542A DE1151933B (en) 1960-07-11 1960-07-11 Process for the production of molded articles or coatings from boron-modified epoxy resins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEL36542A DE1151933B (en) 1960-07-11 1960-07-11 Process for the production of molded articles or coatings from boron-modified epoxy resins
GB3252661A GB948202A (en) 1961-09-11 1961-09-11 Boron-modified epoxide resins

Publications (1)

Publication Number Publication Date
DE1151933B true DE1151933B (en) 1963-07-25

Family

ID=25985349

Family Applications (1)

Application Number Title Priority Date Filing Date
DEL36542A Pending DE1151933B (en) 1960-07-11 1960-07-11 Process for the production of molded articles or coatings from boron-modified epoxy resins

Country Status (1)

Country Link
DE (1) DE1151933B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5225777A (en) * 1992-02-04 1993-07-06 International Business Machines Corporation High density probe

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE564374A (en) * 1957-02-01 1958-07-30
FR1198633A (en) * 1957-02-01 1959-12-08 Shell Res Ltd New boron compounds and their preparation processes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE564374A (en) * 1957-02-01 1958-07-30
FR1198633A (en) * 1957-02-01 1959-12-08 Shell Res Ltd New boron compounds and their preparation processes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5225777A (en) * 1992-02-04 1993-07-06 International Business Machines Corporation High density probe

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