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The ring-opening metathesis polymerization reaction of dicyclopentadiene (DCPD) was carried out using Grubbs first generation catalyst. Fourier transform infrared (FTIR), dynamic-thermo mechanical analysis (DMA), and Raman spectroscopy were used to investigate the curing behavior of this polymer. The FTIR results showed that DCPD had not cured completely and the polymers were composed of linear and cross-linked polydicyclopentadiene (PDCPD). The DMA test showed that the polymer possesses the glass transition temperature of linear PDCPD and cross-linked PDCPD, which had also proved the FTIR result. Furthermore, in order to explain the strange phenomenon that the band at 3004 cm−1 should have been detected in infrared spectrum, the Raman spectrum of PDCPD was applied to analyze the bonding mechanism of =C–H bond in the process of polymerization. Moreover, the real-time FTIR result cure formula showed that the cure degree increases first then constants trend with cure time of increasing, the cure degree reached the maximum value (96.76%) at 60°C for 192 h.