Study of the Effects of the Structure of Phthalazinone’s Side-Group on the Properties of the Poly(phthalazinone ether ketone)s Resins

Abstract

The application of poly(phthalazinone ether ketone)s (PPEKs) resin containing phthalazinone moiety is limited, due to its poor thermoforming processability. To investigate the effects of the phthalazinone’s side-group on the thermal stability and processability of the resin, a series of PPEKs resins with different side-group (–H/–CH3/–Ph) were prepared by nucleophilic aromatic substitution polymerization. The properties of the obtained resins were investigated by differential scanning calorimetry analysis (DSC), thermogravimetric analysis (TGA), dynamic thermomechanical analysis (DMA), and rheogoniometer. The results show that the introduction of methyl or phenyl into the PPEKs resin, significantly reduced the melting viscosity of the resin, but resulted in a slight decrease in the thermal stability of it. This might be due to the presence of methyl or phenyl, which enhanced the free volume of the molecule and reduced the entanglement between the chains; the results of the computer simulation confirmed it. Moreover, the resin films displayed excellent tensile strength with the introduction of methyl or phenyl. In a word, a novel poly(phthalazinone ether ketone)s resin with thermal resistance, easy processing and excellent mechanical properties could be obtained by introducing appropriate bulk-rigid side-groups into the phthalazinone moiety.

Enhancing Tissue Adhesion and Osteoblastic Differentiation of MC3T3‐E1 Cells on Poly(aryl ether ketone) by Chemically Anchored Hydroxyapatite Nanocomposite Hydrogel Coating

“…It could be seen that the peak at δ = 8.6 ppm was assigned to the proton H f of the DHPZ moiety of the APPBAESKs molecule ( Figure 3 a). [ 39 ] And the characteristic peak intensity of H f was obviously getting smaller with the decrease of DHPZ moiety content. Similarly, the characteristic peaks of allyl protons of DABPA observed at δ = 3.3 ppm, δ = 5 ppm, and δ = 6.2 ppm were, respectively, assigned to the proton H de , H ab , H c of the allyl group as expected, indicating the successful polymerization.…”

Apatite Formation Induced by Chitosan/Gelatin Hydrogel Coating Anchored on Poly(aryl ether nitrile ketone) Substrates to Promote Osteoblastic Differentiation

“…PPENK‐d was synthesized following a similar procedure to that of the previous work. [ 3 ] Briefly, DHPZ (12.4 mmol, 2.9512 g), 2,6‐difluorobenzonitrile (DFBN; 12.4 mmol, 1.7236 g), ortho ‐diallyl bisphenol (DABPA; 12.4 mmol, 3.8192 g), bis(4‐fluorophenyl)‐methanone (DFK; 12.4 mmol, 2.604 g), potassium carbonate (K 2 CO 3 ; 34.72 mmol, 4.7983 g), sulfolane (10 mL), and toluene (10 mL) were added to a three‐necked flask that was equipped with a nitrogen inlet. The reaction system was heated for 4 h to 130–135 °C.…”

“…Moreover, it can barely perform the molding processing, although it can perform thermal processing. [ 3 ] Therefore, the development of new polyarylene ether materials with excellent solubility and good processibility has become one of the hotspots of recent research. To solve this challenge, our group previously developed 4‐(4‐hydroxyphenyl)‐phthlazin‐1(2 H )‐one (DHPZ) in 1993, after which our efforts had been focused on synthesizing a series of poly(phthalazinone ether nitrile ketones) (PPENKs) with good solubility and high thermal properties through the introduction of twisted, noncoplanar phthalazinonemoieties into poly(aryl ether nitrile ketone).…”

“…To solve this challenge, our group previously developed 4‐(4‐hydroxyphenyl)‐phthlazin‐1(2 H )‐one (DHPZ) in 1993, after which our efforts had been focused on synthesizing a series of poly(phthalazinone ether nitrile ketones) (PPENKs) with good solubility and high thermal properties through the introduction of twisted, noncoplanar phthalazinonemoieties into poly(aryl ether nitrile ketone). [ 3–5 ] PEEK and PPENK are biologically inert and require surface modification to improve their cytocompatibilities for utilization as a bone‐implant material. However, it is still challenging to impart polyarylene ethers with good biocompatibility.…”

Enhanced toughness and thermal properties of bismaleimide resin based on the synergistic effect of reactive amino‐terminal poly(phthalazinone ether nitrile sulfone) and bisallyl bearing diphenol group

“…Polymers containing phthalazinone moiety have good solubility and higher T g than those of PEI, PEEK and PES, due to the introduction of noncoplanar and heterocyclic moieties into the main chains 33,34 . We have reported the modified BMI/DABPA systems by thermoplastic poly(phthalazinone ether ketone) (PPEK) 35 or poly(phthalazinone ether nitrile ketone) (PPENK) 36 with moderately improved impact toughness.…”