Synthesis, Characterization, and Cure of Propargyl-Functionalized Cyclopentadiene for Use in Carbon-Carbon Composites
Polymers and High Performance Materials
A new composite resin was synthesized by reaction of cyclopentadiene with propargyl bromide and base under phase transfer conditions to give a mixture of products with two to six propargyl functionalities per cyclopentadiene ring. DSC analysis of the propargylated cyclopentadiene resin (PCP) showed thermal cure with no added initiator over a broad temperature range with a peak at 250 degrees C. FT-IR analysis of the cured resin showed the generation of new unsaturated and saturated species through a hydrogen transfer ene-like reaction and polyaddition of the propargyl groups to give oligomers and/or cyclotrimers. X-ray analysis showed no long-range graphitic order, Neat PCP resin cured at 250 degrees C gave a room temperature flexural modulus of 2.9-3.0 GPa by DMA and showed no thermal transitions up to 300 degrees C while PCP/carbon fiber composites gave a room-temperature flexural modulus of 115-120 GPa and a flexural strength of approximately 950 MPa, TGA showed exceptional carbon yield at 1000 degrees C with 75% weight retention in both air and N-2, while composites with 40 wt % resin showed 90% carbon yield. Interlaminar shear strengths of carbonized samples were comparable to those of presently used materials.
Chemistry of Materials
Tregre, G. J.,
Mathias, L. J.
(1999). Synthesis, Characterization, and Cure of Propargyl-Functionalized Cyclopentadiene for Use in Carbon-Carbon Composites. Chemistry of Materials, 11(3), 698-703.
Available at: https://aquila.usm.edu/fac_pubs/4578