High-Temperature Thermosets Derived from the Diels-Alder Polymerization of Bisbenzocyclobutenes and Bimaleimides

Abstract

A number of compatible mixtures of 2,2-bis4-(N-4-benzocyclobutenyl phthalimide-4-phenyl hexafluoropropane (BCB) and 1,1'-(methylene di-4, 1- phenylene) bismaleimide (BMI) were prepared. Complete compatibility of the mixtures was evidence by a single initial t sub g. All mixtures showed relatively low initial t sub g's and characteristic polymerization exotherms of benzocyclobutene-based systems providing and excellent processing window. The cured sample of the mixtures, pure BCB and BMI were subjected to comparative isothermal gravimetric analysis (ITGA). After 200 hours at 650 F (343 C) in circulating air, the cured BMI exhibited similar thermo-oxidative stabilities to BCB. A model compound was synthesized from the intimate mixture of N-phenyl maleimide and N-benzocyclobutenyl phthalimide in 63% recrystallized yield. The ITGA results and isolation of the model Diels-Alder adduct render strong support to the conviction that Diels-Alder polymerization is the predominant curing process in the BCB/BMI system.

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Document Details

Document Type
Technical Report
Publication Date
Sep 01, 1987
Accession Number
ADA188800

Entities

People

  • Edward J. Soloski
  • Fred E. Arnold
  • Loon-Seng Tan

Organizations

  • Wright Laboratory

Tags

Communities of Interest

  • C4I
  • Energy and Power Technologies

DTIC Thesaurus Topics

  • Air Force
  • Alkenes
  • Alkynes
  • Anhydrides
  • Body Weight
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Gravimetric Analysis
  • High Temperature
  • Imides
  • Mass Spectroscopy
  • Materials
  • Materials Laboratories
  • Methylenes
  • Organic Chemistry
  • Thermosetting Plastics

Fields of Study

  • Chemistry

Readers

  • Polymer Science and Engineering.
  • Polymer Science and Technology