Synthesis of N -substituted poly(benzimidazole ketone ketone)s containing pyridine rings

Sheng

High Performance Polymers

et al. 2020

4-(4-Diphenylphosphino)phenyl-2,6-bis(4-hydroxyphenyl)pyridine, as a new bisphenol monomer, was prepared from 4-(diphenylphosphino)benzaldehyde and 4-hydroxyacetophenone and used in the preparation of several aromatic poly(ether ketone)s (PEKs) containing 2,6-diphenylpyridyl units and diphenylphosphinophenyl pendant groups via a nucleophilic aromatic substitution polycondensation with difluorinated aromatic ketones. The polycondensation proceeded quantitatively in tetramethylene sulfone in the presence of anhydrous potassium carbonate and afforded the polymers with high molecular weights. The resulting PEKs are amorphous and exhibit high glass transition temperatures of 209–255°C and 5% weight loss temperatures of 536–554°C with char yields of 57–62% at 800°C in nitrogen. Their high char yields and good limited oxygen index values ranging from 39 to 43 indicated these polymers exhibited good thermal stability and flame-retardant property. All new PEKs were soluble in common organic solvents such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide, and chloroform and could form tough, flexible, and strong films with tensile strengths of 74.6–86.8 MPa, tensile moduli of 2.9–3.6 GPa, and elongations at break of 5–9%.

Section: Introductionmentioning

confidence: 99%

New poly(aryl ether ketone)s containing 2,6-diphenylpyridyl units and diphenylphosphinophenyl pendant groups

Sheng

High Performance Polymers

et al. 2020

High Performance Polymers

“…16–17 One of the commonly used methods is introducing flexibilizing groups or other bulky units in main or side chain to overcome the restricted polymer solubility. 17 –25 In addition, another such effort involves the substitution of the potentially reactive N–H site in benzimidazole by functional groups, thereby enabling a C–N coupling reaction with activated halides at the appropriate temperature. 17,18 In our previous studies, we synthesized a series of novel N -substituted PBIs which exhibited excellent solubility in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

“…17,18 In our previous studies, we synthesized a series of novel N -substituted PBIs which exhibited excellent solubility in organic solvents. 24,25 However, while improving solubility was achieved, thermal decomposition temperature lowered. In order to obtain high-performance polymer materials with both good processability and improved thermal stability, we first synthesize soluble linear PBI and then make it dissolved in N -methyl-2-pyrrolidone (NMP), and add metal ions into the solution to coordinate and cross-link to form certain shapes (films or blocks).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a metal-coordinated N-substituted polybenzimidazole pyridine sulfone and method for the nondestructive analysis of thermal stability

Yang

et al. 2018

N-substituted metal-coordinated cross-linking polybenzimidazole pyridine sulfone, as novel class of high-performance functional polymers, has been obtained by the coordination of N-substituted polybenzimidazole pyridine sulfone (Py-N-PBIS) ligand with varying content of metallic ion (Co2+, Ni2+, Zn2+). The structures of the polymers are characterized by means of fourier transform infrared spectroscopy (FT-IR) and 1H nuclear magnetic resonance (1H NMR) spectroscopy, the results show good agreement with the proposed structures. Thermogravimetric analysis measurements exhibit that the metal coordination polymers possess good thermal stability with high thermal decomposition temperature (thermally stable up to 405–510°C). More importantly, the thermal decomposition temperature of Py-N-PBIS-(Co2+, Ni2+, Zn2+) can be nondestructively detected by taking advantage of the fluorescence quenching effect of metal coordination to 2,6-Bis(2-benzimidazolyl)pyridine structure.

“…In particular, as one of the most significant heat-resistant engineering polymers, polybenzimidazole(PBI) is widely applied in various fields including films, fibrids, sizings, microporous resins, coatings, molding resins, as well as reinforced composites [11][12][13][14][15][16]. However, the poor solubility of PBI in common organic solvents give rise to processing difficulties and limit their applications [11,12].…”

Section: Introductionmentioning

confidence: 99%

A Metal Coordination Crosslinking Novel High Performance Thermoset

Yang

Chang

2018

MSF

N-substituted crosslinking polybenzimidazole pyridine sulfone, as novel high performance functional polymers, was prepared by the coordination of N-substituted polybenzimidazole pyridine sulfone (Py-N-PBIS) ligand with varying content of metallic ion (Co2+, Ni2+, Zn2+). The structures of the polymers were characterized by means of FT-IR and 1H NMR spectroscopy, and the results showed a good agreement with the proposed structures. TGA measurements exhibited that the crosslinking polymers possessed good thermal stability with high thermal decomposition temperatures (thermally stable up to 405-510 °C). Additionally, the thermal stability of the coordination polymers was improved constantly with the increasing of the content of Co2+, Ni2+ or Zn2+. The metal coordination crosslinking N-substituted polybenzimidazole pyridine sulfone could be considered as a novel high performance thermoset.