Alkyne-containing phthalonitrile resins: Controlling mechanical properties by selective curing

Abstract

An alkyne-containing multiple aromatic ether-linked phthalonitrile has been synthesized and characterized. The oligomeric phthalonitrile monomer was prepared from the reaction of an excess amount of bisphenol A with 4,4 0 -dibromotolane in the presence of K 2 CO 3 in a N,N-dimethylformamide/toluene solvent mixture, followed by end-capping with 4-nitrophthalonitrile in a two-step, one-pot reaction. After being cured in the presence of bis(4-[4-aminophenoxy]phenyl)sulfone, the polymeric properties of the alkyne-and non-alkynecontaining oligomeric phthalonitrile resins were compared.Rheometric measurements and thermogravimetric analysis showed that the alkyne-containing oligomeric phthalonitrile resin had better mechanical properties than an analogous nonalkyne-containing resin cured under identical conditions and exhibited excellent thermal and oxidative properties. V C 2013

Synthesis of bisphenol A‐free oligomeric phthalonitrile resins with sulfone and sulfone‐ketone containing backbones

“…Polymers were reconstituted in a solution of 0.1% trifluoracetic acid in acetonitrile and infused via a TurboV electrospray ionization source (ESI) at a flow rate of 2 mL min 21 . Liquid connections between the on-board syringe pump and the ionization source were constructed of 100 mm i.d.…”

“…m-BAPS was added with stirring. The samples were cooled, placed in an oven, and heated to gelation under argon at 200 8C for 16 h (overnight), then heated to 375 8C for 8h (ramped at 3 8C min 21 ). Selected samples were postcured for an additional 2 h at 415 8C.…”

“…The PN resins are prepared through a two-step, one-pot nucleophilic displacement reaction between activated or unactivated dihaloaromatic compounds and an appropriate bisphenol, followed by end-capping with 4-nitrophthalonitrile. 10,[20][21][22][23] More recently, we have developed an improved synthesis of a sulfonyl-containing PN resin composition by reacting 4-(chlorophenyl) sulfone with an excess of bisphenol A followed by end-capping with 4-nitrophthalonitrile. 23 Although this PN resin had excellent properties, the inclusion of bisphenol A limited the thermal stability to 400 8C.…”

One component propargyl phthalonitrile novolac: Synthesis and characterization

“…Addition curable groups are much compatible and could aid the polymerization and amend the properties of phthalonitrile resins in terms of thermal and chemical stability [27]. In the previous paper, we had reported a thermosetting blend of propargyl ether resin and phthalonitrile resin.…”

The curing behavior and properties of phthalonitrile resins using ionic liquids as a new class of curing agents

“…In order to address this problem, considerable research efforts have been expended on the development for the curing agent. To date, lots of Lewis acids/bases curing agent, such as metallic salts, strong organic acids, strong organic acids/amine salts and active hydrogen-containing heterocyclic structures have been developed and used [8][9][10][11][12][13][14][15][16][17]. In addition to the traditional Lewis acids/bases, our laboratory also reported the cooperative curing effect between phthalonitrile and methyl tetrahydrophthalic anhydride end-capped imide compound (MODA) [18,19].…”