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Main Chain Type Benzoxazine Polymers for High Performance Applications

Chernykh, Andrey
http://rave.ohiolink.edu/etdc/view?acc_num=case1232733414

Abstract Details

2009, Doctor of Philosophy, Case Western Reserve University, Macromolecular Science and Engineering.
A new polymer with benzoxazine group in the main chain has been synthesized through the Mannich condensation of a difunctional phenol, formaldehyde and a diamine. Obtained polymer has weight average molecular weight of approximately 10,000 Da and a moderately broad polydispersity index. The new polymer is used to manufacturer self-supporting film of thermosetting resins. Aiming to obtain higher molecular weight, click chemistry approach has been applied to synthesize linear benzoxazine polymers. Three types of polymers have been prepared from dipropargyl- and novel diazide-functionalized benzoxazine monomers, showing a tremendous flexibility for applying click reaction to obtain various polymer architectures. The weight average molecular weight is estimated to be in the range from 50,000 to 100,000 Da which is significantly higher than the benzoxazine polymers which have been chain extended via Mannich reaction. Further developing approach of polycondensation of the monomers containing ozaxine rings, the oxidative coupling approach has been utilized in order to couple benzoxazines with terminal acetylene groups. A model benzoxazine compound containing diacetylene linkage exhibits unexpectedly low exothermic peak with the onset around 140°C, which is significantly lower than the temperature of conventional benzoxazine polymerization. The initial model studies have been made in order to understand this phenomenon and preliminary explanation is given. Extending this pathway to the difunctional propargyl- and ethynyl-functionalized benzoxazine monomers, a series of novel benzoxazine polymers containing diacetylene groups in the main chain have been synthesized. The weight average molecular weight of the polymers is achieved to be up to 50,000 Da. The effect of diacetylene moiety on the benzoxazine crosslinking behavior is even more pronounced for the obtained linear polymers showing exothermic peak with the onset at around 125°C and its maximum at 185°C. Upon crosslinking, polymers demonstrate outstanding thermal stability with char yield up to 72% and glass transition temperature above 350°C.
Hatsuo Ishida (Advisor)
David Schiraldi (Committee Member)
Gary Wnek (Committee Member)
Syed Qutubuddin (Committee Member)
Polymers
benzoxazine; main chain polymer

Recommended Citations

Citations

  • Chernykh, A. (2009). Main Chain Type Benzoxazine Polymers for High Performance Applications [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1232733414

    APA Style (7th edition)

  • Chernykh, Andrey. Main Chain Type Benzoxazine Polymers for High Performance Applications. 2009. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1232733414.

    MLA Style (8th edition)

  • Chernykh, Andrey. "Main Chain Type Benzoxazine Polymers for High Performance Applications." Doctoral dissertation, Case Western Reserve University, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=case1232733414

    Chicago Manual of Style (17th edition)

case1232733414
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© 2009, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.