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Synthesis and characterization of a novel bisfuran/bismaleimide resin

Waters, John Francis
http://rave.ohiolink.edu/etdc/view?acc_num=case1057157311

Abstract Details

1993, Doctor of Philosophy, Case Western Reserve University, Chemistry.
The synthesis of a novel bisfuran/bismaleimide resin based upon 4,4′-bis(2-furfuryl)phenyl ether (BFPE) and 4,4′-bis(maleimido)diphenylmethane (BMI) is explored. The reactions occurring during the thermal cure the BFPE resin are explored via a model compound study utilizing 2-furfurylbenzene (FB) and N-phenylmaleimide (NPMI). The thermodynamics of the Diels-Alder reaction are reported, along with the charge transfer complex formation and the copolymerization properties. The Diels-Alder reaction occurs readily at room temperature, but easily reverses as low as 40°C, and returns nearly exclusively to starting materials by 60°C. The charge transfer complex between FB and NPMI was shown to occur, but not to play a significant role in the copolymerization process. The copolymerization reactivity ratios of FB and NPMI are reported, and show FB to react nearly exclusively with NPMI radicals during the polymerization process. The polymerization pathways of the resin itself are reported. An initial Diels-Alder reaction between the BFPE and BMI produce a linear polymer with molecular weights in the thousands. The subsequent thermal polymerization is postulated to occur mainly through a reverse Diels-Alder reaction followed by a radical copolymerization. The fo rmation of an aromatic polyimide structure yielding water does not occur to a significant extent. The mechanical properties of the BFPE/BMI resins and of the graphite fiber composites are reported along with two commercial bismaleimide resins: neat 4,4′-bis (maleimido)diphenylmethane (a generic version of Rhone Poulenc's first generation Kerimide resin) and Ciba Geigy's Matrimide TM 5292. Different stoichiometries of each resin were aged at 260°C and the weight loss data are reported. In the neat resin form, the BFPE and Matrimide show comparable rates of weight loss, but BFPE resin shows superior high temperature performance, both mechanically and thermal-oxidatively, when formulated into a composite. A commonly studied commercial polyimide, Kapton H film, was studied via 13C cross polarization/magic angle spinning (CP/MAS) to determine the potential of this technique in characterizing the behavior of absorbed water in insoluble, imide containing polymers. 13C spin lattice relaxation times (T1's) were measured for dry and moisture absorbed, and D2O films to determine the sites of bound water. 13C rotating frame relaxations and inversion recovery cross polarization (IRCP) measurements were performed to determine the effects of bound water on the motional parameters of the polymer itself.
William Ritchey (Advisor)
216 p.
Synthesis and characterization of a novel bisfuran/bismaleimide resin.

Recommended Citations

Citations

  • Waters, J. F. (1993). Synthesis and characterization of a novel bisfuran/bismaleimide resin [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1057157311

    APA Style (7th edition)

  • Waters, John. Synthesis and characterization of a novel bisfuran/bismaleimide resin. 1993. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1057157311.

    MLA Style (8th edition)

  • Waters, John. "Synthesis and characterization of a novel bisfuran/bismaleimide resin." Doctoral dissertation, Case Western Reserve University, 1993. http://rave.ohiolink.edu/etdc/view?acc_num=case1057157311

    Chicago Manual of Style (17th edition)

case1057157311
1,165
© 1993, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.